I looked into Tim’s room. There was just enough light shining through the window to outline my little sissy’s chest moving up and down. He was pretty much in the same position I left him, lying on his back with his arms tied up above him.

I walked over to the bed to look at my sissy. There was dried drool coming from his mouth and dried tears in the corners of his eyes.

I guess I should wake him up.

“Hey, wakey wakey!” I slapped him lightly on the face.

His eyes slowly opened. At first, he seemed to have no idea where he was or what happened to him. I stepped back a bit as thrashed about trying to get out of his restraints.

“What the fuck is going on?” He yelled at me, then remembered what had happened last night. His body went limp.

“Did you sleep well?” I asked jokingly.

It seemed like my little sissy didn’t want to look at me. I could see his face turning red.

“I need to use the bathroom,” he whispered.

“Sure thing,” I untied his arms.

He sat up, rotating his hands and rubbing his wrists, which now had red marks around them. I didn’t tie the ropes very tight, so he was probably trying to get out of them overnight.

“C-can you take this off, too?” He asked, shamefully pointing at the chastity cage that was restraining his little penis.

However, this chastity device was like a metal cage, with a hole at the end that allowed for easy use. It could also be cleaned while it was being worn, so I theoretically never had to take it off.

“Fortunately, there’s no need to take it off. The design is actually perfect for using the bathroom and cleaning, as well,” I smirked evilly.

He looked at me like he wanted to kill me. It was understandable.

“I can see you want to say something,” I noted. “I’ll let you say whatever you want and I won’t punish you.”

“Fuck you, you piece of shit!” He screamed. “Get this fucking thing off me!”

I chuckled at that. It was good to see there was still fight in him. It would only be more satisfying when I broke him.

“Well, I’ll take it off when I think you deserve it.” I waited there while he fumed. “Didn’t you say you have to go to the bathroom?”

With that, he left his room.

I called out after him, “You should hurry up, you don’t want to be late to your classes!”

I left his room as well. The sissy took about half an hour in the bathroom. As he got dressed, he demanded one more time that I take the cage off him, but I denied. I just told him to get back earlier today. I don’t think I had to worry about him telling anyone about what I had done to him. There’s no way his dignity would allow him to tell someone that he’d been taken like a bitch. I laughed at the thought.

“I have a surprise for you when you get back.”

=====

It was about 6 o’clock when Tim got back. It was still pretty late, but early for him.

I was in my room when I heard the apartment door open.

“Hey, Aaron, where the hell are you?” He shouted. “You said you would take this thing off me!”

He burst into my room, demanding that I take his chastity cage off.

“Alright, alright, just hold on a sec.”

I stood up and walked out of my room. Tim followed me. I sat down on the couch and opened up my phone. Tim stared at me as I just sat on the couch, ignoring him. His face was turning red, and I could very clearly see that he was starting to get mad. Strange, even though I had complete control over him, he was acting like he was the boss.

“What the fuck are you waiting for, Aaron!” He demanded. I smiled, hearing the desperation behind his anger.

At that moment, there was a knock on our door. Tim looked confused as I told him to get it.

Tim walked over to the door and opened it, revealing a girl on the other side. She wore yoga pants and a tight t-shirt that outlined her curvy figure. She had blond hair and slightly tanned skin. On her back was a small black backpack. This girl was actually shorter than Tim, which was surprising.

Tim looked at the pretty girl, baffled. I could see his face was now red not because of anger, but embarrassment.

Normally, Tim would’ve wasted no time hitting on this girl. I guess the chastity cage really didn’t put him in the mood.

“So, you’re Tim, right?” She asked. Tim responded with a very audible gulp and a quick head nod.

She then brushed past him into the apartment. I stood to greet her.

“Hey Aaron!” She greeted me.

“Hey Leah,” I responded.

Meanwhile, Tim closed the door and looked at me. I ignored Tim and spoke to Leah for a little bit, then pointed her to his room. She smirked at me and walked into his room, closing the door behind her.

“W-what just happened, Aaron?” Tim asked.

“You’ve never had sex with a girl before, right?”

Tim’s face flushed, but I could tell he was starting to get excited. After about a day of not getting any release, and then seeing a hot girl walk into his bedroom, I think I could predict what he was thinking.

“N-no…” he responded shyly.

“Well, today’s the day, my friend.” I gave him a rough slap on the back.

His face lit up. “Really? Hell yeah! Then let’s get this thing off me so I can get some!”

“Just hold on, kid,” I pushed him towards him room.

“W-wait, Aaron, you have to take this thing off of me first!”

“Don’t worry about it,” I reassured him and kept pushing him towards his room.

I opened the door. Leah was there, standing, naked. However, she had her back to us. Tim’s eyes practically bulged out of his head. I think it was safe to assume that this was the first time he’d ever even seen a naked girl in person. Now he was urgently whispering to me, demanding that I take his cage off. I could hear the strain in his voice.

“Tim, why don’t you get those annoying clothes off for me?” Leah asked. She was still facing the other way, only turning her head to look at us. This girl was so hot. It took all of my restraint not to move to her.

Tim looked at her, then looked at me. The poor kid was confused as hell. I just nodded and told him to do as told. Slowly, a shirt came off, then pants, followed by a very hesitant removal of his boxers.

When part of the metal cage started to peek out, Leah didn’t notice, or at least she pretended not to. This gave Tim some more confidence and he quickened his pace.

“Now get over here and lie down on the bed. Let’s have some fun,” Leah said with a smirk.

The poor kid didn’t know what was happening, but he just did as he was told. He climbed onto the bed and laid down. All the while, Leah kept his back to him.

“Close your eyes baby, I’ll make you feel good,” she crooned.

I walked around to the head of the bed. Leah turned around. I could barely hold in my laughter. Leah sure was a beautiful girl. She had perky breasts and a really curvy and sexy body. However, right over her crotch was a massive black strap-on. It looked like Leah was nearly about to laugh as well.

Tim, being the gullible idiot he was, kept his eyes closed. My sissy slut’s little cock was hardened on the inside of the cage, straining against the metal restraints.

“I’m all nice and lubed up for you, Tim,” Leah whispered. She stroked the lubricated strap-on with her hands. Well, she wasn’t lying!

She got onto the bed and kneeled in between Tim’s legs. Quickly, she grabbed his ankles and lifted them up over her shoulders. At the same time, I grabbed onto his wrists and held them down over his head.

Now, Tim decided to open his eyes to see what was happening. He lifted his head to see the big dildo at the entrance of his asshole. I couldn’t believe how gullible my sissy slave was.

“Oh, no, no, please, don’t do this!” He started screaming.

“Oh, you should be excited, Tim. It’s your first time having sex with a girl after all,” Leah’s seductive voice was full of cruelty.

My own cock was straining against the inside of my pants, but I wanted to let Leah have her fun.

“Do you remember, bitch, what you did to me?” Leah’s voice was full of hatred. It seemed that Tim didn’t know what she was talking about. That made sense, since he didn’t even recognize her. “It was at a party a few months ago. You were probably just following Aaron around like you always do. And I don’t know if you were high or drunk or whatever, but you started feeling me up.”

As she said that, she reached one of her hands down to the chastity cage. She rubbed his restrained cock, which was still hard. Then she cupped his balls in her hand. She started squeezing them lightly.

Tim winced from the slight discomfort. “Please, Leah, I’m so s-sorry, I-I really didn’t mean it…”

“It didn’t seem like it at the time, bitch,” Leah kept squeezing his small balls. “Because you actually pulled me into a bedroom and pushed me back, kinda like what I’m doing to you know.”

My little sissy didn’t try to get out anymore. He was just completely still, sweating and breathing hard due to the pain from Leah’s grip.

“L-look, Leah, p-please, s-stop it. I’m really s-sorry about what I did…” he whispered.

Leah ignored him. “It was a good thing Aaron came along when he did.” She looked at me and gave me a tired smile. “Or else you might’ve done something even worse.”

With that, Leah started to push the strap-on into Tim’s asshole. She still held onto his balls, but it seemed like she was loosening her grip. Tim’s face was red, and I could see his eyes watering up. I didn’t know if it was from humiliation or guilt, or both, but I didn’t feel bad for him after I heard Leah’s story. It was true that I stopped him from doing anything more to Leah, but I couldn’t imagine how many other girls he had also done this to, without anyone to stop him.

Once Leah was able to push the strap-on inside about halfway, she slammed the rest of it into Tim’s asshole with a grunt.

“Ahh!” Tim screamed. “Leah! I’m sorry! Please! Don’t do this!” These begs were followed by Tim’s and Leah’s heavy breathing.

“Look at you, bitch. You’re pathetic. You’re not a man, but you’re not a woman. You’re just a little sissy bitch.” Leah leaned in close to his and spit on him, causing him to flinch and shut his eyes.

Leah regained her posture and started pumping the strap-on into my sissy’s asshole. Despite everything that had just happened, his little cock was still as hard as it could get inside the cage. Leah pulled out, then slammed back in. Every time she thrust in, I watched her boobs shake up and down, while the flesh of Tim’s calves and ass jiggled.

I couldn’t take it anymore. My own cock was about to burst out of my pants. I motioned for Leah to move Tim a little bit, and turned him so that now his head was hanging over the edge of the bed. I was still holding his hands while Leah held his legs up. I held onto both of Tim’s wrists with one hand and used my free hand to remove my pants. Tim had his head hanging over the side of the bed, with his eyes closed.

Without warning, I shoved my freed cock onto his lips. At this point, I couldn’t see his facial reaction, but I could feel him thrashing his head around, underneath my cock.

“Open wide and take that cock like the sissy bitch you are!” Leah ordered. She started squeezing his balls again.

Tim did value his balls, so he did as she told.

“If Aaron feels any teeth, then I swear I will rip your balls off, bitch!” Leah yelled at him. I grinned. Leah was definitely enjoying this.

My cock was also very satisfied. My roommate’s warm and wet mouth surrounded my rock-hard member. I groaned in pleasure. I pushed my cock further, and my tip hit the back of his throat. That didn’t stop me, though. There was still about a quarter of my cock exposed to the cold air.

I thrust my hips forward. I nearly came just from that. The top of Tim’s throat clenched around my sensitive tip. I felt choking, but I didn’t care. I could feel some slight scratching on the top of my cock from Tim’s teeth. I warned him about that, and I could tell that Leah was tightening her grip. My little sissy learned that he could wrap his lips around his teeth to avoid any more trouble. I pulled my cock out of his mouth, but before he could finish taking a deep breath, I thrust it in again. Once again, there was more choking and groaning.

This was a real sight. Just a few days ago, Tim was a sexist, arrogant asshole of a roommate. Now, he was lying in his bed, being penetrated from his asshole and his mouth.

I started thrusting at the rate that Leah was, and we got into a rhythm. We both slammed in deep at the same time, then pulled out. We slammed in deep again, and pulled out. We repeated this process, while Tim was unable to do anything but lie there and take the punishment. As I was getting close to cumming, I saw a glob of pre-cum ooze out of Tim’s little cock and out of the cage, landing on his flat belly. Leah saw this, too, and started thrusting faster.

“Oh, fuck, I’m getting close…” I groaned. I pulled my cock out of my sissy’s mouth and started to jack off. Before Tim could react, I shot my load all over his face. My several thick ropes of cum covered his nose, eyes, cheeks, and lips. I could see that Tim did close his mouth, but I didn’t care. My goal was to humiliate the hell out of him, and that definitely worked.

Leah also pulled the strap-on out of Tim’s asshole. She let go of his legs, and they just dropped onto the bed. I pushed my sissy onto the bed so his head was no longer hanging off the side.

“P-please… I have to cum… just take this cage off of me so I can cum…” I loved hearing my sissy beg. But I didn’t plan on doing anything he asked of me.

“Pathetic,” Leah spat. She wasn’t angry anymore, but she that didn’t mean she was ready to let things go. Leah grabbed Tim by the throat. She slapped him on the face, which caused some of my cum to go flying. I found that rather amusing.

“I’m going to make sure that you never do something like that again. I heard your apology, but I don’t really feel like that was enough,” Leah’s hand was now covered in my cum, so she just smeared it on Tim’s belly, mixing it with the small puddle of Tim’s pre-cum that had formed. “I’m probably going to have to spend some more time with you to make sure that you really meant what you said.”

With that, Leah walked away from Tim and started to get dressed and pack her things away. She was pretty fierce.

My roommate lay on his bed, cock twitching in the cage. He didn’t try to get himself off this time, but I could tell he was debating it. He kept having to blink cum out of his eyes that dripped in, which I found funny. “Well, you really messed with the wrong girl, kid,” I scolded.

Leah left the room. I heard her open the door to our apartment. It slammed shut behind her, leaving me and my roommate together. I turned around for a moment, then looked back to see that Tim was staring at me. He immediately turned away, face reddening.

I put my clothes back on. Tim was lying on the bed, silently sobbing. I realized that night had already fallen. What a crazy 24 hours it had been.

This was going to be a lot of fun.

---

I looked into Tim’s room. There was just enough light shining through the window to outline my little sissy’s chest moving up and down. He was pretty much in the same position I left him, lying on his back with his arms tied up above him.

I walked over to the bed to look at my sissy. There was dried drool coming from his mouth and dried tears in the corners of his eyes.

I guess I should wake him up.

“Hey, wakey wakey!” I slapped him lightly on the face.

His eyes slowly opened. At first, he seemed to have no idea where he was or what happened to him. I stepped back a bit as thrashed about trying to get out of his restraints.

“What the fuck is going on?” He yelled at me, then remembered what had happened last night. His body went limp.

“Did you sleep well?” I asked jokingly.

It seemed like my little sissy didn’t want to look at me. I could see his face turning red.

“I need to use the bathroom,” he whispered.

“Sure thing,” I untied his arms.

He sat up, rotating his hands and rubbing his wrists, which now had red marks around them. I didn’t tie the ropes very tight, so he was probably trying to get out of them overnight.

“C-can you take this off, too?” He asked, shamefully pointing at the chastity cage that was restraining his little penis.

However, this chastity device was like a metal cage, with a hole at the end that allowed for easy use. It could also be cleaned while it was being worn, so I theoretically never had to take it off.

“Fortunately, there’s no need to take it off. The design is actually perfect for using the bathroom and cleaning, as well,” I smirked evilly.

He looked at me like he wanted to kill me. It was understandable.

“I can see you want to say something,” I noted. “I’ll let you say whatever you want and I won’t punish you.”

“Fuck you, you piece of shit!” He screamed. “Get this fucking thing off me!”

I chuckled at that. It was good to see there was still fight in him. It would only be more satisfying when I broke him.

“Well, I’ll take it off when I think you deserve it.” I waited there while he fumed. “Didn’t you say you have to go to the bathroom?”

With that, he left his room.

I called out after him, “You should hurry up, you don’t want to be late to your classes!”

I left his room as well. The sissy took about half an hour in the bathroom. As he got dressed, he demanded one more time that I take the cage off him, but I denied. I just told him to get back earlier today. I don’t think I had to worry about him telling anyone about what I had done to him. There’s no way his dignity would allow him to tell someone that he’d been taken like a bitch. I laughed at the thought.

“I have a surprise for you when you get back.”

=====

It was about 6 o’clock when Tim got back. It was still pretty late, but early for him.

I was in my room when I heard the apartment door open.

“Hey, Aaron, where the hell are you?” He shouted. “You said you would take this thing off me!”

He burst into my room, demanding that I take his chastity cage off.

“Alright, alright, just hold on a sec.”

I stood up and walked out of my room. Tim followed me. I sat down on the couch and opened up my phone. Tim stared at me as I just sat on the couch, ignoring him. His face was turning red, and I could very clearly see that he was starting to get mad. Strange, even though I had complete control over him, he was acting like he was the boss.

“What the fuck are you waiting for, Aaron!” He demanded. I smiled, hearing the desperation behind his anger.

At that moment, there was a knock on our door. Tim looked confused as I told him to get it.

Tim walked over to the door and opened it, revealing a girl on the other side. She wore yoga pants and a tight t-shirt that outlined her curvy figure. She had blond hair and slightly tanned skin. On her back was a small black backpack. This girl was actually shorter than Tim, which was surprising.

Tim looked at the pretty girl, baffled. I could see his face was now red not because of anger, but embarrassment.

Normally, Tim would’ve wasted no time hitting on this girl. I guess the chastity cage really didn’t put him in the mood.

“So, you’re Tim, right?” She asked. Tim responded with a very audible gulp and a quick head nod.

She then brushed past him into the apartment. I stood to greet her.

“Hey Aaron!” She greeted me.

“Hey Leah,” I responded.

Meanwhile, Tim closed the door and looked at me. I ignored Tim and spoke to Leah for a little bit, then pointed her to his room. She smirked at me and walked into his room, closing the door behind her.

“W-what just happened, Aaron?” Tim asked.

“You’ve never had sex with a girl before, right?”

Tim’s face flushed, but I could tell he was starting to get excited. After about a day of not getting any release, and then seeing a hot girl walk into his bedroom, I think I could predict what he was thinking.

“N-no…” he responded shyly.

“Well, today’s the day, my friend.” I gave him a rough slap on the back.

His face lit up. “Really? Hell yeah! Then let’s get this thing off me so I can get some!”

“Just hold on, kid,” I pushed him towards him room.

“W-wait, Aaron, you have to take this thing off of me first!”

“Don’t worry about it,” I reassured him and kept pushing him towards his room.

I opened the door. Leah was there, standing, naked. However, she had her back to us. Tim’s eyes practically bulged out of his head. I think it was safe to assume that this was the first time he’d ever even seen a naked girl in person. Now he was urgently whispering to me, demanding that I take his cage off. I could hear the strain in his voice.

“Tim, why don’t you get those annoying clothes off for me?” Leah asked. She was still facing the other way, only turning her head to look at us. This girl was so hot. It took all of my restraint not to move to her.

Tim looked at her, then looked at me. The poor kid was confused as hell. I just nodded and told him to do as told. Slowly, a shirt came off, then pants, followed by a very hesitant removal of his boxers.

When part of the metal cage started to peek out, Leah didn’t notice, or at least she pretended not to. This gave Tim some more confidence and he quickened his pace.

“Now get over here and lie down on the bed. Let’s have some fun,” Leah said with a smirk.

The poor kid didn’t know what was happening, but he just did as he was told. He climbed onto the bed and laid down. All the while, Leah kept his back to him.

“Close your eyes baby, I’ll make you feel good,” she crooned.

I walked around to the head of the bed. Leah turned around. I could barely hold in my laughter. Leah sure was a beautiful girl. She had perky breasts and a really curvy and sexy body. However, right over her crotch was a massive black strap-on. It looked like Leah was nearly about to laugh as well.

Tim, being the gullible idiot he was, kept his eyes closed. My sissy slut’s little cock was hardened on the inside of the cage, straining against the metal restraints.

“I’m all nice and lubed up for you, Tim,” Leah whispered. She stroked the lubricated strap-on with her hands. Well, she wasn’t lying!

She got onto the bed and kneeled in between Tim’s legs. Quickly, she grabbed his ankles and lifted them up over her shoulders. At the same time, I grabbed onto his wrists and held them down over his head.

Now, Tim decided to open his eyes to see what was happening. He lifted his head to see the big dildo at the entrance of his asshole. I couldn’t believe how gullible my sissy slave was.

“Oh, no, no, please, don’t do this!” He started screaming.

“Oh, you should be excited, Tim. It’s your first time having sex with a girl after all,” Leah’s seductive voice was full of cruelty.

My own cock was straining against the inside of my pants, but I wanted to let Leah have her fun.

“Do you remember, bitch, what you did to me?” Leah’s voice was full of hatred. It seemed that Tim didn’t know what she was talking about. That made sense, since he didn’t even recognize her. “It was at a party a few months ago. You were probably just following Aaron around like you always do. And I don’t know if you were high or drunk or whatever, but you started feeling me up.”

As she said that, she reached one of her hands down to the chastity cage. She rubbed his restrained cock, which was still hard. Then she cupped his balls in her hand. She started squeezing them lightly.

Tim winced from the slight discomfort. “Please, Leah, I’m so s-sorry, I-I really didn’t mean it…”

“It didn’t seem like it at the time, bitch,” Leah kept squeezing his small balls. “Because you actually pulled me into a bedroom and pushed me back, kinda like what I’m doing to you know.”

My little sissy didn’t try to get out anymore. He was just completely still, sweating and breathing hard due to the pain from Leah’s grip.

“L-look, Leah, p-please, s-stop it. I’m really s-sorry about what I did…” he whispered.

Leah ignored him. “It was a good thing Aaron came along when he did.” She looked at me and gave me a tired smile. “Or else you might’ve done something even worse.”

With that, Leah started to push the strap-on into Tim’s asshole. She still held onto his balls, but it seemed like she was loosening her grip. Tim’s face was red, and I could see his eyes watering up. I didn’t know if it was from humiliation or guilt, or both, but I didn’t feel bad for him after I heard Leah’s story. It was true that I stopped him from doing anything more to Leah, but I couldn’t imagine how many other girls he had also done this to, without anyone to stop him.

Once Leah was able to push the strap-on inside about halfway, she slammed the rest of it into Tim’s asshole with a grunt.

“Ahh!” Tim screamed. “Leah! I’m sorry! Please! Don’t do this!” These begs were followed by Tim’s and Leah’s heavy breathing.

“Look at you, bitch. You’re pathetic. You’re not a man, but you’re not a woman. You’re just a little sissy bitch.” Leah leaned in close to his and spit on him, causing him to flinch and shut his eyes.

Leah regained her posture and started pumping the strap-on into my sissy’s asshole. Despite everything that had just happened, his little cock was still as hard as it could get inside the cage. Leah pulled out, then slammed back in. Every time she thrust in, I watched her boobs shake up and down, while the flesh of Tim’s calves and ass jiggled.

I couldn’t take it anymore. My own cock was about to burst out of my pants. I motioned for Leah to move Tim a little bit, and turned him so that now his head was hanging over the edge of the bed. I was still holding his hands while Leah held his legs up. I held onto both of Tim’s wrists with one hand and used my free hand to remove my pants. Tim had his head hanging over the side of the bed, with his eyes closed.

Without warning, I shoved my freed cock onto his lips. At this point, I couldn’t see his facial reaction, but I could feel him thrashing his head around, underneath my cock.

“Open wide and take that cock like the sissy bitch you are!” Leah ordered. She started squeezing his balls again.

Tim did value his balls, so he did as she told.

“If Aaron feels any teeth, then I swear I will rip your balls off, bitch!” Leah yelled at him. I grinned. Leah was definitely enjoying this.

My cock was also very satisfied. My roommate’s warm and wet mouth surrounded my rock-hard member. I groaned in pleasure. I pushed my cock further, and my tip hit the back of his throat. That didn’t stop me, though. There was still about a quarter of my cock exposed to the cold air.

I thrust my hips forward. I nearly came just from that. The top of Tim’s throat clenched around my sensitive tip. I felt choking, but I didn’t care. I could feel some slight scratching on the top of my cock from Tim’s teeth. I warned him about that, and I could tell that Leah was tightening her grip. My little sissy learned that he could wrap his lips around his teeth to avoid any more trouble. I pulled my cock out of his mouth, but before he could finish taking a deep breath, I thrust it in again. Once again, there was more choking and groaning.

This was a real sight. Just a few days ago, Tim was a sexist, arrogant asshole of a roommate. Now, he was lying in his bed, being penetrated from his asshole and his mouth.

I started thrusting at the rate that Leah was, and we got into a rhythm. We both slammed in deep at the same time, then pulled out. We slammed in deep again, and pulled out. We repeated this process, while Tim was unable to do anything but lie there and take the punishment. As I was getting close to cumming, I saw a glob of pre-cum ooze out of Tim’s little cock and out of the cage, landing on his flat belly. Leah saw this, too, and started thrusting faster.

“Oh, fuck, I’m getting close…” I groaned. I pulled my cock out of my sissy’s mouth and started to jack off. Before Tim could react, I shot my load all over his face. My several thick ropes of cum covered his nose, eyes, cheeks, and lips. I could see that Tim did close his mouth, but I didn’t care. My goal was to humiliate the hell out of him, and that definitely worked.

Leah also pulled the strap-on out of Tim’s asshole. She let go of his legs, and they just dropped onto the bed. I pushed my sissy onto the bed so his head was no longer hanging off the side.

“P-please… I have to cum… just take this cage off of me so I can cum…” I loved hearing my sissy beg. But I didn’t plan on doing anything he asked of me.

“Pathetic,” Leah spat. She wasn’t angry anymore, but she that didn’t mean she was ready to let things go. Leah grabbed Tim by the throat. She slapped him on the face, which caused some of my cum to go flying. I found that rather amusing.

“I’m going to make sure that you never do something like that again. I heard your apology, but I don’t really feel like that was enough,” Leah’s hand was now covered in my cum, so she just smeared it on Tim’s belly, mixing it with the small puddle of Tim’s pre-cum that had formed. “I’m probably going to have to spend some more time with you to make sure that you really meant what you said.”

With that, Leah walked away from Tim and started to get dressed and pack her things away. She was pretty fierce.

My roommate lay on his bed, cock twitching in the cage. He didn’t try to get himself off this time, but I could tell he was debating it. He kept having to blink cum out of his eyes that dripped in, which I found funny. “Well, you really messed with the wrong girl, kid,” I scolded.

Leah left the room. I heard her open the door to our apartment. It slammed shut behind her, leaving me and my roommate together. I turned around for a moment, then looked back to see that Tim was staring at me. He immediately turned away, face reddening.

I put my clothes back on. Tim was lying on the bed, silently sobbing. I realized that night had already fallen. What a crazy 24 hours it had been.

This was going to be a lot of fun.

---

I looked into Tim’s room. There was just enough light shining through the window to outline my little sissy’s chest moving up and down. He was pretty much in the same position I left him, lying on his back with his arms tied up above him.

I walked over to the bed to look at my sissy. There was dried drool coming from his mouth and dried tears in the corners of his eyes.

I guess I should wake him up.

“Hey, wakey wakey!” I slapped him lightly on the face.

His eyes slowly opened. At first, he seemed to have no idea where he was or what happened to him. I stepped back a bit as thrashed about trying to get out of his restraints.

“What the fuck is going on?” He yelled at me, then remembered what had happened last night. His body went limp.

“Did you sleep well?” I asked jokingly.

It seemed like my little sissy didn’t want to look at me. I could see his face turning red.

“I need to use the bathroom,” he whispered.

“Sure thing,” I untied his arms.

He sat up, rotating his hands and rubbing his wrists, which now had red marks around them. I didn’t tie the ropes very tight, so he was probably trying to get out of them overnight.

“C-can you take this off, too?” He asked, shamefully pointing at the chastity cage that was restraining his little penis.

However, this chastity device was like a metal cage, with a hole at the end that allowed for easy use. It could also be cleaned while it was being worn, so I theoretically never had to take it off.

“Fortunately, there’s no need to take it off. The design is actually perfect for using the bathroom and cleaning, as well,” I smirked evilly.

He looked at me like he wanted to kill me. It was understandable.

“I can see you want to say something,” I noted. “I’ll let you say whatever you want and I won’t punish you.”

“Fuck you, you piece of shit!” He screamed. “Get this fucking thing off me!”

I chuckled at that. It was good to see there was still fight in him. It would only be more satisfying when I broke him.

“Well, I’ll take it off when I think you deserve it.” I waited there while he fumed. “Didn’t you say you have to go to the bathroom?”

With that, he left his room.

I called out after him, “You should hurry up, you don’t want to be late to your classes!”

I left his room as well. The sissy took about half an hour in the bathroom. As he got dressed, he demanded one more time that I take the cage off him, but I denied. I just told him to get back earlier today. I don’t think I had to worry about him telling anyone about what I had done to him. There’s no way his dignity would allow him to tell someone that he’d been taken like a bitch. I laughed at the thought.

“I have a surprise for you when you get back.”

=====

It was about 6 o’clock when Tim got back. It was still pretty late, but early for him.

I was in my room when I heard the apartment door open.

“Hey, Aaron, where the hell are you?” He shouted. “You said you would take this thing off me!”

He burst into my room, demanding that I take his chastity cage off.

“Alright, alright, just hold on a sec.”

I stood up and walked out of my room. Tim followed me. I sat down on the couch and opened up my phone. Tim stared at me as I just sat on the couch, ignoring him. His face was turning red, and I could very clearly see that he was starting to get mad. Strange, even though I had complete control over him, he was acting like he was the boss.

“What the fuck are you waiting for, Aaron!” He demanded. I smiled, hearing the desperation behind his anger.

At that moment, there was a knock on our door. Tim looked confused as I told him to get it.

Tim walked over to the door and opened it, revealing a girl on the other side. She wore yoga pants and a tight t-shirt that outlined her curvy figure. She had blond hair and slightly tanned skin. On her back was a small black backpack. This girl was actually shorter than Tim, which was surprising.

Tim looked at the pretty girl, baffled. I could see his face was now red not because of anger, but embarrassment.

Normally, Tim would’ve wasted no time hitting on this girl. I guess the chastity cage really didn’t put him in the mood.

“So, you’re Tim, right?” She asked. Tim responded with a very audible gulp and a quick head nod.

She then brushed past him into the apartment. I stood to greet her.

“Hey Aaron!” She greeted me.

“Hey Leah,” I responded.

Meanwhile, Tim closed the door and looked at me. I ignored Tim and spoke to Leah for a little bit, then pointed her to his room. She smirked at me and walked into his room, closing the door behind her.

“W-what just happened, Aaron?” Tim asked.

“You’ve never had sex with a girl before, right?”

Tim’s face flushed, but I could tell he was starting to get excited. After about a day of not getting any release, and then seeing a hot girl walk into his bedroom, I think I could predict what he was thinking.

“N-no…” he responded shyly.

“Well, today’s the day, my friend.” I gave him a rough slap on the back.

His face lit up. “Really? Hell yeah! Then let’s get this thing off me so I can get some!”

“Just hold on, kid,” I pushed him towards him room.

“W-wait, Aaron, you have to take this thing off of me first!”

“Don’t worry about it,” I reassured him and kept pushing him towards his room.

I opened the door. Leah was there, standing, naked. However, she had her back to us. Tim’s eyes practically bulged out of his head. I think it was safe to assume that this was the first time he’d ever even seen a naked girl in person. Now he was urgently whispering to me, demanding that I take his cage off. I could hear the strain in his voice.

“Tim, why don’t you get those annoying clothes off for me?” Leah asked. She was still facing the other way, only turning her head to look at us. This girl was so hot. It took all of my restraint not to move to her.

Tim looked at her, then looked at me. The poor kid was confused as hell. I just nodded and told him to do as told. Slowly, a shirt came off, then pants, followed by a very hesitant removal of his boxers.

When part of the metal cage started to peek out, Leah didn’t notice, or at least she pretended not to. This gave Tim some more confidence and he quickened his pace.

“Now get over here and lie down on the bed. Let’s have some fun,” Leah said with a smirk.

The poor kid didn’t know what was happening, but he just did as he was told. He climbed onto the bed and laid down. All the while, Leah kept his back to him.

“Close your eyes baby, I’ll make you feel good,” she crooned.

I walked around to the head of the bed. Leah turned around. I could barely hold in my laughter. Leah sure was a beautiful girl. She had perky breasts and a really curvy and sexy body. However, right over her crotch was a massive black strap-on. It looked like Leah was nearly about to laugh as well.

Tim, being the gullible idiot he was, kept his eyes closed. My sissy slut’s little cock was hardened on the inside of the cage, straining against the metal restraints.

“I’m all nice and lubed up for you, Tim,” Leah whispered. She stroked the lubricated strap-on with her hands. Well, she wasn’t lying!

She got onto the bed and kneeled in between Tim’s legs. Quickly, she grabbed his ankles and lifted them up over her shoulders. At the same time, I grabbed onto his wrists and held them down over his head.

Now, Tim decided to open his eyes to see what was happening. He lifted his head to see the big dildo at the entrance of his asshole. I couldn’t believe how gullible my sissy slave was.

“Oh, no, no, please, don’t do this!” He started screaming.

“Oh, you should be excited, Tim. It’s your first time having sex with a girl after all,” Leah’s seductive voice was full of cruelty.

My own cock was straining against the inside of my pants, but I wanted to let Leah have her fun.

“Do you remember, bitch, what you did to me?” Leah’s voice was full of hatred. It seemed that Tim didn’t know what she was talking about. That made sense, since he didn’t even recognize her. “It was at a party a few months ago. You were probably just following Aaron around like you always do. And I don’t know if you were high or drunk or whatever, but you started feeling me up.”

As she said that, she reached one of her hands down to the chastity cage. She rubbed his restrained cock, which was still hard. Then she cupped his balls in her hand. She started squeezing them lightly.

Tim winced from the slight discomfort. “Please, Leah, I’m so s-sorry, I-I really didn’t mean it…”

“It didn’t seem like it at the time, bitch,” Leah kept squeezing his small balls. “Because you actually pulled me into a bedroom and pushed me back, kinda like what I’m doing to you know.”

My little sissy didn’t try to get out anymore. He was just completely still, sweating and breathing hard due to the pain from Leah’s grip.

“L-look, Leah, p-please, s-stop it. I’m really s-sorry about what I did…” he whispered.

Leah ignored him. “It was a good thing Aaron came along when he did.” She looked at me and gave me a tired smile. “Or else you might’ve done something even worse.”

With that, Leah started to push the strap-on into Tim’s asshole. She still held onto his balls, but it seemed like she was loosening her grip. Tim’s face was red, and I could see his eyes watering up. I didn’t know if it was from humiliation or guilt, or both, but I didn’t feel bad for him after I heard Leah’s story. It was true that I stopped him from doing anything more to Leah, but I couldn’t imagine how many other girls he had also done this to, without anyone to stop him.

Once Leah was able to push the strap-on inside about halfway, she slammed the rest of it into Tim’s asshole with a grunt.

“Ahh!” Tim screamed. “Leah! I’m sorry! Please! Don’t do this!” These begs were followed by Tim’s and Leah’s heavy breathing.

“Look at you, bitch. You’re pathetic. You’re not a man, but you’re not a woman. You’re just a little sissy bitch.” Leah leaned in close to his and spit on him, causing him to flinch and shut his eyes.

Leah regained her posture and started pumping the strap-on into my sissy’s asshole. Despite everything that had just happened, his little cock was still as hard as it could get inside the cage. Leah pulled out, then slammed back in. Every time she thrust in, I watched her boobs shake up and down, while the flesh of Tim’s calves and ass jiggled.

I couldn’t take it anymore. My own cock was about to burst out of my pants. I motioned for Leah to move Tim a little bit, and turned him so that now his head was hanging over the edge of the bed. I was still holding his hands while Leah held his legs up. I held onto both of Tim’s wrists with one hand and used my free hand to remove my pants. Tim had his head hanging over the side of the bed, with his eyes closed.

Without warning, I shoved my freed cock onto his lips. At this point, I couldn’t see his facial reaction, but I could feel him thrashing his head around, underneath my cock.

“Open wide and take that cock like the sissy bitch you are!” Leah ordered. She started squeezing his balls again.

Tim did value his balls, so he did as she told.

“If Aaron feels any teeth, then I swear I will rip your balls off, bitch!” Leah yelled at him. I grinned. Leah was definitely enjoying this.

My cock was also very satisfied. My roommate’s warm and wet mouth surrounded my rock-hard member. I groaned in pleasure. I pushed my cock further, and my tip hit the back of his throat. That didn’t stop me, though. There was still about a quarter of my cock exposed to the cold air.

I thrust my hips forward. I nearly came just from that. The top of Tim’s throat clenched around my sensitive tip. I felt choking, but I didn’t care. I could feel some slight scratching on the top of my cock from Tim’s teeth. I warned him about that, and I could tell that Leah was tightening her grip. My little sissy learned that he could wrap his lips around his teeth to avoid any more trouble. I pulled my cock out of his mouth, but before he could finish taking a deep breath, I thrust it in again. Once again, there was more choking and groaning.

This was a real sight. Just a few days ago, Tim was a sexist, arrogant asshole of a roommate. Now, he was lying in his bed, being penetrated from his asshole and his mouth.

I started thrusting at the rate that Leah was, and we got into a rhythm. We both slammed in deep at the same time, then pulled out. We slammed in deep again, and pulled out. We repeated this process, while Tim was unable to do anything but lie there and take the punishment. As I was getting close to cumming, I saw a glob of pre-cum ooze out of Tim’s little cock and out of the cage, landing on his flat belly. Leah saw this, too, and started thrusting faster.

“Oh, fuck, I’m getting close…” I groaned. I pulled my cock out of my sissy’s mouth and started to jack off. Before Tim could react, I shot my load all over his face. My several thick ropes of cum covered his nose, eyes, cheeks, and lips. I could see that Tim did close his mouth, but I didn’t care. My goal was to humiliate the hell out of him, and that definitely worked.

Leah also pulled the strap-on out of Tim’s asshole. She let go of his legs, and they just dropped onto the bed. I pushed my sissy onto the bed so his head was no longer hanging off the side.

“P-please… I have to cum… just take this cage off of me so I can cum…” I loved hearing my sissy beg. But I didn’t plan on doing anything he asked of me.

“Pathetic,” Leah spat. She wasn’t angry anymore, but she that didn’t mean she was ready to let things go. Leah grabbed Tim by the throat. She slapped him on the face, which caused some of my cum to go flying. I found that rather amusing.

“I’m going to make sure that you never do something like that again. I heard your apology, but I don’t really feel like that was enough,” Leah’s hand was now covered in my cum, so she just smeared it on Tim’s belly, mixing it with the small puddle of Tim’s pre-cum that had formed. “I’m probably going to have to spend some more time with you to make sure that you really meant what you said.”

With that, Leah walked away from Tim and started to get dressed and pack her things away. She was pretty fierce.

My roommate lay on his bed, cock twitching in the cage. He didn’t try to get himself off this time, but I could tell he was debating it. He kept having to blink cum out of his eyes that dripped in, which I found funny. “Well, you really messed with the wrong girl, kid,” I scolded.

Leah left the room. I heard her open the door to our apartment. It slammed shut behind her, leaving me and my roommate together. I turned around for a moment, then looked back to see that Tim was staring at me. He immediately turned away, face reddening.

I put my clothes back on. Tim was lying on the bed, silently sobbing. I realized that night had already fallen. What a crazy 24 hours it had been.

This was going to be a lot of fun.

---

I looked into Tim’s room. There was just enough light shining through the window to outline my little sissy’s chest moving up and down. He was pretty much in the same position I left him, lying on his back with his arms tied up above him.

I walked over to the bed to look at my sissy. There was dried drool coming from his mouth and dried tears in the corners of his eyes.

I guess I should wake him up.

“Hey, wakey wakey!” I slapped him lightly on the face.

His eyes slowly opened. At first, he seemed to have no idea where he was or what happened to him. I stepped back a bit as thrashed about trying to get out of his restraints.

“What the fuck is going on?” He yelled at me, then remembered what had happened last night. His body went limp.

“Did you sleep well?” I asked jokingly.

It seemed like my little sissy didn’t want to look at me. I could see his face turning red.

“I need to use the bathroom,” he whispered.

“Sure thing,” I untied his arms.

He sat up, rotating his hands and rubbing his wrists, which now had red marks around them. I didn’t tie the ropes very tight, so he was probably trying to get out of them overnight.

“C-can you take this off, too?” He asked, shamefully pointing at the chastity cage that was restraining his little penis.

However, this chastity device was like a metal cage, with a hole at the end that allowed for easy use. It could also be cleaned while it was being worn, so I theoretically never had to take it off.

“Fortunately, there’s no need to take it off. The design is actually perfect for using the bathroom and cleaning, as well,” I smirked evilly.

He looked at me like he wanted to kill me. It was understandable.

“I can see you want to say something,” I noted. “I’ll let you say whatever you want and I won’t punish you.”

“Fuck you, you piece of shit!” He screamed. “Get this fucking thing off me!”

I chuckled at that. It was good to see there was still fight in him. It would only be more satisfying when I broke him.

“Well, I’ll take it off when I think you deserve it.” I waited there while he fumed. “Didn’t you say you have to go to the bathroom?”

With that, he left his room.

I called out after him, “You should hurry up, you don’t want to be late to your classes!”

I left his room as well. The sissy took about half an hour in the bathroom. As he got dressed, he demanded one more time that I take the cage off him, but I denied. I just told him to get back earlier today. I don’t think I had to worry about him telling anyone about what I had done to him. There’s no way his dignity would allow him to tell someone that he’d been taken like a bitch. I laughed at the thought.

“I have a surprise for you when you get back.”

=====

It was about 6 o’clock when Tim got back. It was still pretty late, but early for him.

I was in my room when I heard the apartment door open.

“Hey, Aaron, where the hell are you?” He shouted. “You said you would take this thing off me!”

He burst into my room, demanding that I take his chastity cage off.

“Alright, alright, just hold on a sec.”

I stood up and walked out of my room. Tim followed me. I sat down on the couch and opened up my phone. Tim stared at me as I just sat on the couch, ignoring him. His face was turning red, and I could very clearly see that he was starting to get mad. Strange, even though I had complete control over him, he was acting like he was the boss.

“What the fuck are you waiting for, Aaron!” He demanded. I smiled, hearing the desperation behind his anger.

At that moment, there was a knock on our door. Tim looked confused as I told him to get it.

Tim walked over to the door and opened it, revealing a girl on the other side. She wore yoga pants and a tight t-shirt that outlined her curvy figure. She had blond hair and slightly tanned skin. On her back was a small black backpack. This girl was actually shorter than Tim, which was surprising.

Tim looked at the pretty girl, baffled. I could see his face was now red not because of anger, but embarrassment.

Normally, Tim would’ve wasted no time hitting on this girl. I guess the chastity cage really didn’t put him in the mood.

“So, you’re Tim, right?” She asked. Tim responded with a very audible gulp and a quick head nod.

She then brushed past him into the apartment. I stood to greet her.

“Hey Aaron!” She greeted me.

“Hey Leah,” I responded.

Meanwhile, Tim closed the door and looked at me. I ignored Tim and spoke to Leah for a little bit, then pointed her to his room. She smirked at me and walked into his room, closing the door behind her.

“W-what just happened, Aaron?” Tim asked.

“You’ve never had sex with a girl before, right?”

Tim’s face flushed, but I could tell he was starting to get excited. After about a day of not getting any release, and then seeing a hot girl walk into his bedroom, I think I could predict what he was thinking.

“N-no…” he responded shyly.

“Well, today’s the day, my friend.” I gave him a rough slap on the back.

His face lit up. “Really? Hell yeah! Then let’s get this thing off me so I can get some!”

“Just hold on, kid,” I pushed him towards him room.

“W-wait, Aaron, you have to take this thing off of me first!”

“Don’t worry about it,” I reassured him and kept pushing him towards his room.

I opened the door. Leah was there, standing, naked. However, she had her back to us. Tim’s eyes practically bulged out of his head. I think it was safe to assume that this was the first time he’d ever even seen a naked girl in person. Now he was urgently whispering to me, demanding that I take his cage off. I could hear the strain in his voice.

“Tim, why don’t you get those annoying clothes off for me?” Leah asked. She was still facing the other way, only turning her head to look at us. This girl was so hot. It took all of my restraint not to move to her.

Tim looked at her, then looked at me. The poor kid was confused as hell. I just nodded and told him to do as told. Slowly, a shirt came off, then pants, followed by a very hesitant removal of his boxers.

When part of the metal cage started to peek out, Leah didn’t notice, or at least she pretended not to. This gave Tim some more confidence and he quickened his pace.

“Now get over here and lie down on the bed. Let’s have some fun,” Leah said with a smirk.

The poor kid didn’t know what was happening, but he just did as he was told. He climbed onto the bed and laid down. All the while, Leah kept his back to him.

“Close your eyes baby, I’ll make you feel good,” she crooned.

I walked around to the head of the bed. Leah turned around. I could barely hold in my laughter. Leah sure was a beautiful girl. She had perky breasts and a really curvy and sexy body. However, right over her crotch was a massive black strap-on. It looked like Leah was nearly about to laugh as well.

Tim, being the gullible idiot he was, kept his eyes closed. My sissy slut’s little cock was hardened on the inside of the cage, straining against the metal restraints.

“I’m all nice and lubed up for you, Tim,” Leah whispered. She stroked the lubricated strap-on with her hands. Well, she wasn’t lying!

She got onto the bed and kneeled in between Tim’s legs. Quickly, she grabbed his ankles and lifted them up over her shoulders. At the same time, I grabbed onto his wrists and held them down over his head.

Now, Tim decided to open his eyes to see what was happening. He lifted his head to see the big dildo at the entrance of his asshole. I couldn’t believe how gullible my sissy slave was.

“Oh, no, no, please, don’t do this!” He started screaming.

“Oh, you should be excited, Tim. It’s your first time having sex with a girl after all,” Leah’s seductive voice was full of cruelty.

My own cock was straining against the inside of my pants, but I wanted to let Leah have her fun.

“Do you remember, bitch, what you did to me?” Leah’s voice was full of hatred. It seemed that Tim didn’t know what she was talking about. That made sense, since he didn’t even recognize her. “It was at a party a few months ago. You were probably just following Aaron around like you always do. And I don’t know if you were high or drunk or whatever, but you started feeling me up.”

As she said that, she reached one of her hands down to the chastity cage. She rubbed his restrained cock, which was still hard. Then she cupped his balls in her hand. She started squeezing them lightly.

Tim winced from the slight discomfort. “Please, Leah, I’m so s-sorry, I-I really didn’t mean it…”

“It didn’t seem like it at the time, bitch,” Leah kept squeezing his small balls. “Because you actually pulled me into a bedroom and pushed me back, kinda like what I’m doing to you know.”

My little sissy didn’t try to get out anymore. He was just completely still, sweating and breathing hard due to the pain from Leah’s grip.

“L-look, Leah, p-please, s-stop it. I’m really s-sorry about what I did…” he whispered.

Leah ignored him. “It was a good thing Aaron came along when he did.” She looked at me and gave me a tired smile. “Or else you might’ve done something even worse.”

With that, Leah started to push the strap-on into Tim’s asshole. She still held onto his balls, but it seemed like she was loosening her grip. Tim’s face was red, and I could see his eyes watering up. I didn’t know if it was from humiliation or guilt, or both, but I didn’t feel bad for him after I heard Leah’s story. It was true that I stopped him from doing anything more to Leah, but I couldn’t imagine how many other girls he had also done this to, without anyone to stop him.

Once Leah was able to push the strap-on inside about halfway, she slammed the rest of it into Tim’s asshole with a grunt.

“Ahh!” Tim screamed. “Leah! I’m sorry! Please! Don’t do this!” These begs were followed by Tim’s and Leah’s heavy breathing.

“Look at you, bitch. You’re pathetic. You’re not a man, but you’re not a woman. You’re just a little sissy bitch.” Leah leaned in close to his and spit on him, causing him to flinch and shut his eyes.

Leah regained her posture and started pumping the strap-on into my sissy’s asshole. Despite everything that had just happened, his little cock was still as hard as it could get inside the cage. Leah pulled out, then slammed back in. Every time she thrust in, I watched her boobs shake up and down, while the flesh of Tim’s calves and ass jiggled.

I couldn’t take it anymore. My own cock was about to burst out of my pants. I motioned for Leah to move Tim a little bit, and turned him so that now his head was hanging over the edge of the bed. I was still holding his hands while Leah held his legs up. I held onto both of Tim’s wrists with one hand and used my free hand to remove my pants. Tim had his head hanging over the side of the bed, with his eyes closed.

Without warning, I shoved my freed cock onto his lips. At this point, I couldn’t see his facial reaction, but I could feel him thrashing his head around, underneath my cock.

“Open wide and take that cock like the sissy bitch you are!” Leah ordered. She started squeezing his balls again.

Tim did value his balls, so he did as she told.

“If Aaron feels any teeth, then I swear I will rip your balls off, bitch!” Leah yelled at him. I grinned. Leah was definitely enjoying this.

My cock was also very satisfied. My roommate’s warm and wet mouth surrounded my rock-hard member. I groaned in pleasure. I pushed my cock further, and my tip hit the back of his throat. That didn’t stop me, though. There was still about a quarter of my cock exposed to the cold air.

I thrust my hips forward. I nearly came just from that. The top of Tim’s throat clenched around my sensitive tip. I felt choking, but I didn’t care. I could feel some slight scratching on the top of my cock from Tim’s teeth. I warned him about that, and I could tell that Leah was tightening her grip. My little sissy learned that he could wrap his lips around his teeth to avoid any more trouble. I pulled my cock out of his mouth, but before he could finish taking a deep breath, I thrust it in again. Once again, there was more choking and groaning.

This was a real sight. Just a few days ago, Tim was a sexist, arrogant asshole of a roommate. Now, he was lying in his bed, being penetrated from his asshole and his mouth.

I started thrusting at the rate that Leah was, and we got into a rhythm. We both slammed in deep at the same time, then pulled out. We slammed in deep again, and pulled out. We repeated this process, while Tim was unable to do anything but lie there and take the punishment. As I was getting close to cumming, I saw a glob of pre-cum ooze out of Tim’s little cock and out of the cage, landing on his flat belly. Leah saw this, too, and started thrusting faster.

“Oh, fuck, I’m getting close…” I groaned. I pulled my cock out of my sissy’s mouth and started to jack off. Before Tim could react, I shot my load all over his face. My several thick ropes of cum covered his nose, eyes, cheeks, and lips. I could see that Tim did close his mouth, but I didn’t care. My goal was to humiliate the hell out of him, and that definitely worked.

Leah also pulled the strap-on out of Tim’s asshole. She let go of his legs, and they just dropped onto the bed. I pushed my sissy onto the bed so his head was no longer hanging off the side.

“P-please… I have to cum… just take this cage off of me so I can cum…” I loved hearing my sissy beg. But I didn’t plan on doing anything he asked of me.

“Pathetic,” Leah spat. She wasn’t angry anymore, but she that didn’t mean she was ready to let things go. Leah grabbed Tim by the throat. She slapped him on the face, which caused some of my cum to go flying. I found that rather amusing.

“I’m going to make sure that you never do something like that again. I heard your apology, but I don’t really feel like that was enough,” Leah’s hand was now covered in my cum, so she just smeared it on Tim’s belly, mixing it with the small puddle of Tim’s pre-cum that had formed. “I’m probably going to have to spend some more time with you to make sure that you really meant what you said.”

With that, Leah walked away from Tim and started to get dressed and pack her things away. She was pretty fierce.

My roommate lay on his bed, cock twitching in the cage. He didn’t try to get himself off this time, but I could tell he was debating it. He kept having to blink cum out of his eyes that dripped in, which I found funny. “Well, you really messed with the wrong girl, kid,” I scolded.

Leah left the room. I heard her open the door to our apartment. It slammed shut behind her, leaving me and my roommate together. I turned around for a moment, then looked back to see that Tim was staring at me. He immediately turned away, face reddening.

I put my clothes back on. Tim was lying on the bed, silently sobbing. I realized that night had already fallen. What a crazy 24 hours it had been.

This was going to be a lot of fun.

---

I looked into Tim’s room. There was just enough light shining through the window to outline my little sissy’s chest moving up and down. He was pretty much in the same position I left him, lying on his back with his arms tied up above him.

I walked over to the bed to look at my sissy. There was dried drool coming from his mouth and dried tears in the corners of his eyes.

I guess I should wake him up.

“Hey, wakey wakey!” I slapped him lightly on the face.

His eyes slowly opened. At first, he seemed to have no idea where he was or what happened to him. I stepped back a bit as thrashed about trying to get out of his restraints.

“What the fuck is going on?” He yelled at me, then remembered what had happened last night. His body went limp.

“Did you sleep well?” I asked jokingly.

It seemed like my little sissy didn’t want to look at me. I could see his face turning red.

“I need to use the bathroom,” he whispered.

“Sure thing,” I untied his arms.

He sat up, rotating his hands and rubbing his wrists, which now had red marks around them. I didn’t tie the ropes very tight, so he was probably trying to get out of them overnight.

“C-can you take this off, too?” He asked, shamefully pointing at the chastity cage that was restraining his little penis.

However, this chastity device was like a metal cage, with a hole at the end that allowed for easy use. It could also be cleaned while it was being worn, so I theoretically never had to take it off.

“Fortunately, there’s no need to take it off. The design is actually perfect for using the bathroom and cleaning, as well,” I smirked evilly.

He looked at me like he wanted to kill me. It was understandable.

“I can see you want to say something,” I noted. “I’ll let you say whatever you want and I won’t punish you.”

“Fuck you, you piece of shit!” He screamed. “Get this fucking thing off me!”

I chuckled at that. It was good to see there was still fight in him. It would only be more satisfying when I broke him.

“Well, I’ll take it off when I think you deserve it.” I waited there while he fumed. “Didn’t you say you have to go to the bathroom?”

With that, he left his room.

I called out after him, “You should hurry up, you don’t want to be late to your classes!”

I left his room as well. The sissy took about half an hour in the bathroom. As he got dressed, he demanded one more time that I take the cage off him, but I denied. I just told him to get back earlier today. I don’t think I had to worry about him telling anyone about what I had done to him. There’s no way his dignity would allow him to tell someone that he’d been taken like a bitch. I laughed at the thought.

“I have a surprise for you when you get back.”

=====

It was about 6 o’clock when Tim got back. It was still pretty late, but early for him.

I was in my room when I heard the apartment door open.

“Hey, Aaron, where the hell are you?” He shouted. “You said you would take this thing off me!”

He burst into my room, demanding that I take his chastity cage off.

“Alright, alright, just hold on a sec.”

I stood up and walked out of my room. Tim followed me. I sat down on the couch and opened up my phone. Tim stared at me as I just sat on the couch, ignoring him. His face was turning red, and I could very clearly see that he was starting to get mad. Strange, even though I had complete control over him, he was acting like he was the boss.

“What the fuck are you waiting for, Aaron!” He demanded. I smiled, hearing the desperation behind his anger.

At that moment, there was a knock on our door. Tim looked confused as I told him to get it.

Tim walked over to the door and opened it, revealing a girl on the other side. She wore yoga pants and a tight t-shirt that outlined her curvy figure. She had blond hair and slightly tanned skin. On her back was a small black backpack. This girl was actually shorter than Tim, which was surprising.

Tim looked at the pretty girl, baffled. I could see his face was now red not because of anger, but embarrassment.

Normally, Tim would’ve wasted no time hitting on this girl. I guess the chastity cage really didn’t put him in the mood.

“So, you’re Tim, right?” She asked. Tim responded with a very audible gulp and a quick head nod.

She then brushed past him into the apartment. I stood to greet her.

“Hey Aaron!” She greeted me.

“Hey Leah,” I responded.

Meanwhile, Tim closed the door and looked at me. I ignored Tim and spoke to Leah for a little bit, then pointed her to his room. She smirked at me and walked into his room, closing the door behind her.

“W-what just happened, Aaron?” Tim asked.

“You’ve never had sex with a girl before, right?”

Tim’s face flushed, but I could tell he was starting to get excited. After about a day of not getting any release, and then seeing a hot girl walk into his bedroom, I think I could predict what he was thinking.

“N-no…” he responded shyly.

“Well, today’s the day, my friend.” I gave him a rough slap on the back.

His face lit up. “Really? Hell yeah! Then let’s get this thing off me so I can get some!”

“Just hold on, kid,” I pushed him towards him room.

“W-wait, Aaron, you have to take this thing off of me first!”

“Don’t worry about it,” I reassured him and kept pushing him towards his room.

I opened the door. Leah was there, standing, naked. However, she had her back to us. Tim’s eyes practically bulged out of his head. I think it was safe to assume that this was the first time he’d ever even seen a naked girl in person. Now he was urgently whispering to me, demanding that I take his cage off. I could hear the strain in his voice.

“Tim, why don’t you get those annoying clothes off for me?” Leah asked. She was still facing the other way, only turning her head to look at us. This girl was so hot. It took all of my restraint not to move to her.

Tim looked at her, then looked at me. The poor kid was confused as hell. I just nodded and told him to do as told. Slowly, a shirt came off, then pants, followed by a very hesitant removal of his boxers.

When part of the metal cage started to peek out, Leah didn’t notice, or at least she pretended not to. This gave Tim some more confidence and he quickened his pace.

“Now get over here and lie down on the bed. Let’s have some fun,” Leah said with a smirk.

The poor kid didn’t know what was happening, but he just did as he was told. He climbed onto the bed and laid down. All the while, Leah kept his back to him.

“Close your eyes baby, I’ll make you feel good,” she crooned.

I walked around to the head of the bed. Leah turned around. I could barely hold in my laughter. Leah sure was a beautiful girl. She had perky breasts and a really curvy and sexy body. However, right over her crotch was a massive black strap-on. It looked like Leah was nearly about to laugh as well.

Tim, being the gullible idiot he was, kept his eyes closed. My sissy slut’s little cock was hardened on the inside of the cage, straining against the metal restraints.

“I’m all nice and lubed up for you, Tim,” Leah whispered. She stroked the lubricated strap-on with her hands. Well, she wasn’t lying!

She got onto the bed and kneeled in between Tim’s legs. Quickly, she grabbed his ankles and lifted them up over her shoulders. At the same time, I grabbed onto his wrists and held them down over his head.

Now, Tim decided to open his eyes to see what was happening. He lifted his head to see the big dildo at the entrance of his asshole. I couldn’t believe how gullible my sissy slave was.

“Oh, no, no, please, don’t do this!” He started screaming.

“Oh, you should be excited, Tim. It’s your first time having sex with a girl after all,” Leah’s seductive voice was full of cruelty.

My own cock was straining against the inside of my pants, but I wanted to let Leah have her fun.

“Do you remember, bitch, what you did to me?” Leah’s voice was full of hatred. It seemed that Tim didn’t know what she was talking about. That made sense, since he didn’t even recognize her. “It was at a party a few months ago. You were probably just following Aaron around like you always do. And I don’t know if you were high or drunk or whatever, but you started feeling me up.”

As she said that, she reached one of her hands down to the chastity cage. She rubbed his restrained cock, which was still hard. Then she cupped his balls in her hand. She started squeezing them lightly.

Tim winced from the slight discomfort. “Please, Leah, I’m so s-sorry, I-I really didn’t mean it…”

“It didn’t seem like it at the time, bitch,” Leah kept squeezing his small balls. “Because you actually pulled me into a bedroom and pushed me back, kinda like what I’m doing to you know.”

My little sissy didn’t try to get out anymore. He was just completely still, sweating and breathing hard due to the pain from Leah’s grip.

“L-look, Leah, p-please, s-stop it. I’m really s-sorry about what I did…” he whispered.

Leah ignored him. “It was a good thing Aaron came along when he did.” She looked at me and gave me a tired smile. “Or else you might’ve done something even worse.”

With that, Leah started to push the strap-on into Tim’s asshole. She still held onto his balls, but it seemed like she was loosening her grip. Tim’s face was red, and I could see his eyes watering up. I didn’t know if it was from humiliation or guilt, or both, but I didn’t feel bad for him after I heard Leah’s story. It was true that I stopped him from doing anything more to Leah, but I couldn’t imagine how many other girls he had also done this to, without anyone to stop him.

Once Leah was able to push the strap-on inside about halfway, she slammed the rest of it into Tim’s asshole with a grunt.

“Ahh!” Tim screamed. “Leah! I’m sorry! Please! Don’t do this!” These begs were followed by Tim’s and Leah’s heavy breathing.

“Look at you, bitch. You’re pathetic. You’re not a man, but you’re not a woman. You’re just a little sissy bitch.” Leah leaned in close to his and spit on him, causing him to flinch and shut his eyes.

Leah regained her posture and started pumping the strap-on into my sissy’s asshole. Despite everything that had just happened, his little cock was still as hard as it could get inside the cage. Leah pulled out, then slammed back in. Every time she thrust in, I watched her boobs shake up and down, while the flesh of Tim’s calves and ass jiggled.

I couldn’t take it anymore. My own cock was about to burst out of my pants. I motioned for Leah to move Tim a little bit, and turned him so that now his head was hanging over the edge of the bed. I was still holding his hands while Leah held his legs up. I held onto both of Tim’s wrists with one hand and used my free hand to remove my pants. Tim had his head hanging over the side of the bed, with his eyes closed.

Without warning, I shoved my freed cock onto his lips. At this point, I couldn’t see his facial reaction, but I could feel him thrashing his head around, underneath my cock.

“Open wide and take that cock like the sissy bitch you are!” Leah ordered. She started squeezing his balls again.

Tim did value his balls, so he did as she told.

“If Aaron feels any teeth, then I swear I will rip your balls off, bitch!” Leah yelled at him. I grinned. Leah was definitely enjoying this.

My cock was also very satisfied. My roommate’s warm and wet mouth surrounded my rock-hard member. I groaned in pleasure. I pushed my cock further, and my tip hit the back of his throat. That didn’t stop me, though. There was still about a quarter of my cock exposed to the cold air.

I thrust my hips forward. I nearly came just from that. The top of Tim’s throat clenched around my sensitive tip. I felt choking, but I didn’t care. I could feel some slight scratching on the top of my cock from Tim’s teeth. I warned him about that, and I could tell that Leah was tightening her grip. My little sissy learned that he could wrap his lips around his teeth to avoid any more trouble. I pulled my cock out of his mouth, but before he could finish taking a deep breath, I thrust it in again. Once again, there was more choking and groaning.

This was a real sight. Just a few days ago, Tim was a sexist, arrogant asshole of a roommate. Now, he was lying in his bed, being penetrated from his asshole and his mouth.

I started thrusting at the rate that Leah was, and we got into a rhythm. We both slammed in deep at the same time, then pulled out. We slammed in deep again, and pulled out. We repeated this process, while Tim was unable to do anything but lie there and take the punishment. As I was getting close to cumming, I saw a glob of pre-cum ooze out of Tim’s little cock and out of the cage, landing on his flat belly. Leah saw this, too, and started thrusting faster.

“Oh, fuck, I’m getting close…” I groaned. I pulled my cock out of my sissy’s mouth and started to jack off. Before Tim could react, I shot my load all over his face. My several thick ropes of cum covered his nose, eyes, cheeks, and lips. I could see that Tim did close his mouth, but I didn’t care. My goal was to humiliate the hell out of him, and that definitely worked.

Leah also pulled the strap-on out of Tim’s asshole. She let go of his legs, and they just dropped onto the bed. I pushed my sissy onto the bed so his head was no longer hanging off the side.

“P-please… I have to cum… just take this cage off of me so I can cum…” I loved hearing my sissy beg. But I didn’t plan on doing anything he asked of me.

“Pathetic,” Leah spat. She wasn’t angry anymore, but she that didn’t mean she was ready to let things go. Leah grabbed Tim by the throat. She slapped him on the face, which caused some of my cum to go flying. I found that rather amusing.

“I’m going to make sure that you never do something like that again. I heard your apology, but I don’t really feel like that was enough,” Leah’s hand was now covered in my cum, so she just smeared it on Tim’s belly, mixing it with the small puddle of Tim’s pre-cum that had formed. “I’m probably going to have to spend some more time with you to make sure that you really meant what you said.”

With that, Leah walked away from Tim and started to get dressed and pack her things away. She was pretty fierce.

My roommate lay on his bed, cock twitching in the cage. He didn’t try to get himself off this time, but I could tell he was debating it. He kept having to blink cum out of his eyes that dripped in, which I found funny. “Well, you really messed with the wrong girl, kid,” I scolded.

Leah left the room. I heard her open the door to our apartment. It slammed shut behind her, leaving me and my roommate together. I turned around for a moment, then looked back to see that Tim was staring at me. He immediately turned away, face reddening.

I put my clothes back on. Tim was lying on the bed, silently sobbing. I realized that night had already fallen. What a crazy 24 hours it had been.

This was going to be a lot of fun.

---

I looked into Tim’s room. There was just enough light shining through the window to outline my little sissy’s chest moving up and down. He was pretty much in the same position I left him, lying on his back with his arms tied up above him.

I walked over to the bed to look at my sissy. There was dried drool coming from his mouth and dried tears in the corners of his eyes.

I guess I should wake him up.

“Hey, wakey wakey!” I slapped him lightly on the face.

His eyes slowly opened. At first, he seemed to have no idea where he was or what happened to him. I stepped back a bit as thrashed about trying to get out of his restraints.

“What the fuck is going on?” He yelled at me, then remembered what had happened last night. His body went limp.

“Did you sleep well?” I asked jokingly.

It seemed like my little sissy didn’t want to look at me. I could see his face turning red.

“I need to use the bathroom,” he whispered.

“Sure thing,” I untied his arms.

He sat up, rotating his hands and rubbing his wrists, which now had red marks around them. I didn’t tie the ropes very tight, so he was probably trying to get out of them overnight.

“C-can you take this off, too?” He asked, shamefully pointing at the chastity cage that was restraining his little penis.

However, this chastity device was like a metal cage, with a hole at the end that allowed for easy use. It could also be cleaned while it was being worn, so I theoretically never had to take it off.

“Fortunately, there’s no need to take it off. The design is actually perfect for using the bathroom and cleaning, as well,” I smirked evilly.

He looked at me like he wanted to kill me. It was understandable.

“I can see you want to say something,” I noted. “I’ll let you say whatever you want and I won’t punish you.”

“Fuck you, you piece of shit!” He screamed. “Get this fucking thing off me!”

I chuckled at that. It was good to see there was still fight in him. It would only be more satisfying when I broke him.

“Well, I’ll take it off when I think you deserve it.” I waited there while he fumed. “Didn’t you say you have to go to the bathroom?”

With that, he left his room.

I called out after him, “You should hurry up, you don’t want to be late to your classes!”

I left his room as well. The sissy took about half an hour in the bathroom. As he got dressed, he demanded one more time that I take the cage off him, but I denied. I just told him to get back earlier today. I don’t think I had to worry about him telling anyone about what I had done to him. There’s no way his dignity would allow him to tell someone that he’d been taken like a bitch. I laughed at the thought.

“I have a surprise for you when you get back.”

=====

It was about 6 o’clock when Tim got back. It was still pretty late, but early for him.

I was in my room when I heard the apartment door open.

“Hey, Aaron, where the hell are you?” He shouted. “You said you would take this thing off me!”

He burst into my room, demanding that I take his chastity cage off.

“Alright, alright, just hold on a sec.”

I stood up and walked out of my room. Tim followed me. I sat down on the couch and opened up my phone. Tim stared at me as I just sat on the couch, ignoring him. His face was turning red, and I could very clearly see that he was starting to get mad. Strange, even though I had complete control over him, he was acting like he was the boss.

“What the fuck are you waiting for, Aaron!” He demanded. I smiled, hearing the desperation behind his anger.

At that moment, there was a knock on our door. Tim looked confused as I told him to get it.

Tim walked over to the door and opened it, revealing a girl on the other side. She wore yoga pants and a tight t-shirt that outlined her curvy figure. She had blond hair and slightly tanned skin. On her back was a small black backpack. This girl was actually shorter than Tim, which was surprising.

Tim looked at the pretty girl, baffled. I could see his face was now red not because of anger, but embarrassment.

Normally, Tim would’ve wasted no time hitting on this girl. I guess the chastity cage really didn’t put him in the mood.

“So, you’re Tim, right?” She asked. Tim responded with a very audible gulp and a quick head nod.

She then brushed past him into the apartment. I stood to greet her.

“Hey Aaron!” She greeted me.

“Hey Leah,” I responded.

Meanwhile, Tim closed the door and looked at me. I ignored Tim and spoke to Leah for a little bit, then pointed her to his room. She smirked at me and walked into his room, closing the door behind her.

“W-what just happened, Aaron?” Tim asked.

“You’ve never had sex with a girl before, right?”

Tim’s face flushed, but I could tell he was starting to get excited. After about a day of not getting any release, and then seeing a hot girl walk into his bedroom, I think I could predict what he was thinking.

“N-no…” he responded shyly.

“Well, today’s the day, my friend.” I gave him a rough slap on the back.

His face lit up. “Really? Hell yeah! Then let’s get this thing off me so I can get some!”

“Just hold on, kid,” I pushed him towards him room.

“W-wait, Aaron, you have to take this thing off of me first!”

“Don’t worry about it,” I reassured him and kept pushing him towards his room.

I opened the door. Leah was there, standing, naked. However, she had her back to us. Tim’s eyes practically bulged out of his head. I think it was safe to assume that this was the first time he’d ever even seen a naked girl in person. Now he was urgently whispering to me, demanding that I take his cage off. I could hear the strain in his voice.

“Tim, why don’t you get those annoying clothes off for me?” Leah asked. She was still facing the other way, only turning her head to look at us. This girl was so hot. It took all of my restraint not to move to her.

Tim looked at her, then looked at me. The poor kid was confused as hell. I just nodded and told him to do as told. Slowly, a shirt came off, then pants, followed by a very hesitant removal of his boxers.

When part of the metal cage started to peek out, Leah didn’t notice, or at least she pretended not to. This gave Tim some more confidence and he quickened his pace.

“Now get over here and lie down on the bed. Let’s have some fun,” Leah said with a smirk.

The poor kid didn’t know what was happening, but he just did as he was told. He climbed onto the bed and laid down. All the while, Leah kept his back to him.

“Close your eyes baby, I’ll make you feel good,” she crooned.

I walked around to the head of the bed. Leah turned around. I could barely hold in my laughter. Leah sure was a beautiful girl. She had perky breasts and a really curvy and sexy body. However, right over her crotch was a massive black strap-on. It looked like Leah was nearly about to laugh as well.

Tim, being the gullible idiot he was, kept his eyes closed. My sissy slut’s little cock was hardened on the inside of the cage, straining against the metal restraints.

“I’m all nice and lubed up for you, Tim,” Leah whispered. She stroked the lubricated strap-on with her hands. Well, she wasn’t lying!

She got onto the bed and kneeled in between Tim’s legs. Quickly, she grabbed his ankles and lifted them up over her shoulders. At the same time, I grabbed onto his wrists and held them down over his head.

Now, Tim decided to open his eyes to see what was happening. He lifted his head to see the big dildo at the entrance of his asshole. I couldn’t believe how gullible my sissy slave was.

“Oh, no, no, please, don’t do this!” He started screaming.

“Oh, you should be excited, Tim. It’s your first time having sex with a girl after all,” Leah’s seductive voice was full of cruelty.

My own cock was straining against the inside of my pants, but I wanted to let Leah have her fun.

“Do you remember, bitch, what you did to me?” Leah’s voice was full of hatred. It seemed that Tim didn’t know what she was talking about. That made sense, since he didn’t even recognize her. “It was at a party a few months ago. You were probably just following Aaron around like you always do. And I don’t know if you were high or drunk or whatever, but you started feeling me up.”

As she said that, she reached one of her hands down to the chastity cage. She rubbed his restrained cock, which was still hard. Then she cupped his balls in her hand. She started squeezing them lightly.

Tim winced from the slight discomfort. “Please, Leah, I’m so s-sorry, I-I really didn’t mean it…”

“It didn’t seem like it at the time, bitch,” Leah kept squeezing his small balls. “Because you actually pulled me into a bedroom and pushed me back, kinda like what I’m doing to you know.”

My little sissy didn’t try to get out anymore. He was just completely still, sweating and breathing hard due to the pain from Leah’s grip.

“L-look, Leah, p-please, s-stop it. I’m really s-sorry about what I did…” he whispered.

Leah ignored him. “It was a good thing Aaron came along when he did.” She looked at me and gave me a tired smile. “Or else you might’ve done something even worse.”

With that, Leah started to push the strap-on into Tim’s asshole. She still held onto his balls, but it seemed like she was loosening her grip. Tim’s face was red, and I could see his eyes watering up. I didn’t know if it was from humiliation or guilt, or both, but I didn’t feel bad for him after I heard Leah’s story. It was true that I stopped him from doing anything more to Leah, but I couldn’t imagine how many other girls he had also done this to, without anyone to stop him.

Once Leah was able to push the strap-on inside about halfway, she slammed the rest of it into Tim’s asshole with a grunt.

“Ahh!” Tim screamed. “Leah! I’m sorry! Please! Don’t do this!” These begs were followed by Tim’s and Leah’s heavy breathing.

“Look at you, bitch. You’re pathetic. You’re not a man, but you’re not a woman. You’re just a little sissy bitch.” Leah leaned in close to his and spit on him, causing him to flinch and shut his eyes.

Leah regained her posture and started pumping the strap-on into my sissy’s asshole. Despite everything that had just happened, his little cock was still as hard as it could get inside the cage. Leah pulled out, then slammed back in. Every time she thrust in, I watched her boobs shake up and down, while the flesh of Tim’s calves and ass jiggled.

I couldn’t take it anymore. My own cock was about to burst out of my pants. I motioned for Leah to move Tim a little bit, and turned him so that now his head was hanging over the edge of the bed. I was still holding his hands while Leah held his legs up. I held onto both of Tim’s wrists with one hand and used my free hand to remove my pants. Tim had his head hanging over the side of the bed, with his eyes closed.

Without warning, I shoved my freed cock onto his lips. At this point, I couldn’t see his facial reaction, but I could feel him thrashing his head around, underneath my cock.

“Open wide and take that cock like the sissy bitch you are!” Leah ordered. She started squeezing his balls again.

Tim did value his balls, so he did as she told.

“If Aaron feels any teeth, then I swear I will rip your balls off, bitch!” Leah yelled at him. I grinned. Leah was definitely enjoying this.

My cock was also very satisfied. My roommate’s warm and wet mouth surrounded my rock-hard member. I groaned in pleasure. I pushed my cock further, and my tip hit the back of his throat. That didn’t stop me, though. There was still about a quarter of my cock exposed to the cold air.

I thrust my hips forward. I nearly came just from that. The top of Tim’s throat clenched around my sensitive tip. I felt choking, but I didn’t care. I could feel some slight scratching on the top of my cock from Tim’s teeth. I warned him about that, and I could tell that Leah was tightening her grip. My little sissy learned that he could wrap his lips around his teeth to avoid any more trouble. I pulled my cock out of his mouth, but before he could finish taking a deep breath, I thrust it in again. Once again, there was more choking and groaning.

This was a real sight. Just a few days ago, Tim was a sexist, arrogant asshole of a roommate. Now, he was lying in his bed, being penetrated from his asshole and his mouth.

I started thrusting at the rate that Leah was, and we got into a rhythm. We both slammed in deep at the same time, then pulled out. We slammed in deep again, and pulled out. We repeated this process, while Tim was unable to do anything but lie there and take the punishment. As I was getting close to cumming, I saw a glob of pre-cum ooze out of Tim’s little cock and out of the cage, landing on his flat belly. Leah saw this, too, and started thrusting faster.

“Oh, fuck, I’m getting close…” I groaned. I pulled my cock out of my sissy’s mouth and started to jack off. Before Tim could react, I shot my load all over his face. My several thick ropes of cum covered his nose, eyes, cheeks, and lips. I could see that Tim did close his mouth, but I didn’t care. My goal was to humiliate the hell out of him, and that definitely worked.

Leah also pulled the strap-on out of Tim’s asshole. She let go of his legs, and they just dropped onto the bed. I pushed my sissy onto the bed so his head was no longer hanging off the side.

“P-please… I have to cum… just take this cage off of me so I can cum…” I loved hearing my sissy beg. But I didn’t plan on doing anything he asked of me.

“Pathetic,” Leah spat. She wasn’t angry anymore, but she that didn’t mean she was ready to let things go. Leah grabbed Tim by the throat. She slapped him on the face, which caused some of my cum to go flying. I found that rather amusing.

“I’m going to make sure that you never do something like that again. I heard your apology, but I don’t really feel like that was enough,” Leah’s hand was now covered in my cum, so she just smeared it on Tim’s belly, mixing it with the small puddle of Tim’s pre-cum that had formed. “I’m probably going to have to spend some more time with you to make sure that you really meant what you said.”

With that, Leah walked away from Tim and started to get dressed and pack her things away. She was pretty fierce.

My roommate lay on his bed, cock twitching in the cage. He didn’t try to get himself off this time, but I could tell he was debating it. He kept having to blink cum out of his eyes that dripped in, which I found funny. “Well, you really messed with the wrong girl, kid,” I scolded.

Leah left the room. I heard her open the door to our apartment. It slammed shut behind her, leaving me and my roommate together. I turned around for a moment, then looked back to see that Tim was staring at me. He immediately turned away, face reddening.

I put my clothes back on. Tim was lying on the bed, silently sobbing. I realized that night had already fallen. What a crazy 24 hours it had been.

This was going to be a lot of fun.

---

I looked into Tim’s room. There was just enough light shining through the window to outline my little sissy’s chest moving up and down. He was pretty much in the same position I left him, lying on his back with his arms tied up above him.

I walked over to the bed to look at my sissy. There was dried drool coming from his mouth and dried tears in the corners of his eyes.

I guess I should wake him up.

“Hey, wakey wakey!” I slapped him lightly on the face.

His eyes slowly opened. At first, he seemed to have no idea where he was or what happened to him. I stepped back a bit as thrashed about trying to get out of his restraints.

“What the fuck is going on?” He yelled at me, then remembered what had happened last night. His body went limp.

“Did you sleep well?” I asked jokingly.

It seemed like my little sissy didn’t want to look at me. I could see his face turning red.

“I need to use the bathroom,” he whispered.

“Sure thing,” I untied his arms.

He sat up, rotating his hands and rubbing his wrists, which now had red marks around them. I didn’t tie the ropes very tight, so he was probably trying to get out of them overnight.

“C-can you take this off, too?” He asked, shamefully pointing at the chastity cage that was restraining his little penis.

However, this chastity device was like a metal cage, with a hole at the end that allowed for easy use. It could also be cleaned while it was being worn, so I theoretically never had to take it off.

“Fortunately, there’s no need to take it off. The design is actually perfect for using the bathroom and cleaning, as well,” I smirked evilly.

He looked at me like he wanted to kill me. It was understandable.

“I can see you want to say something,” I noted. “I’ll let you say whatever you want and I won’t punish you.”

“Fuck you, you piece of shit!” He screamed. “Get this fucking thing off me!”

I chuckled at that. It was good to see there was still fight in him. It would only be more satisfying when I broke him.

“Well, I’ll take it off when I think you deserve it.” I waited there while he fumed. “Didn’t you say you have to go to the bathroom?”

With that, he left his room.

I called out after him, “You should hurry up, you don’t want to be late to your classes!”

I left his room as well. The sissy took about half an hour in the bathroom. As he got dressed, he demanded one more time that I take the cage off him, but I denied. I just told him to get back earlier today. I don’t think I had to worry about him telling anyone about what I had done to him. There’s no way his dignity would allow him to tell someone that he’d been taken like a bitch. I laughed at the thought.

“I have a surprise for you when you get back.”

=====

It was about 6 o’clock when Tim got back. It was still pretty late, but early for him.

I was in my room when I heard the apartment door open.

“Hey, Aaron, where the hell are you?” He shouted. “You said you would take this thing off me!”

He burst into my room, demanding that I take his chastity cage off.

“Alright, alright, just hold on a sec.”

I stood up and walked out of my room. Tim followed me. I sat down on the couch and opened up my phone. Tim stared at me as I just sat on the couch, ignoring him. His face was turning red, and I could very clearly see that he was starting to get mad. Strange, even though I had complete control over him, he was acting like he was the boss.

“What the fuck are you waiting for, Aaron!” He demanded. I smiled, hearing the desperation behind his anger.

At that moment, there was a knock on our door. Tim looked confused as I told him to get it.

Tim walked over to the door and opened it, revealing a girl on the other side. She wore yoga pants and a tight t-shirt that outlined her curvy figure. She had blond hair and slightly tanned skin. On her back was a small black backpack. This girl was actually shorter than Tim, which was surprising.

Tim looked at the pretty girl, baffled. I could see his face was now red not because of anger, but embarrassment.

Normally, Tim would’ve wasted no time hitting on this girl. I guess the chastity cage really didn’t put him in the mood.

“So, you’re Tim, right?” She asked. Tim responded with a very audible gulp and a quick head nod.

She then brushed past him into the apartment. I stood to greet her.

“Hey Aaron!” She greeted me.

“Hey Leah,” I responded.

Meanwhile, Tim closed the door and looked at me. I ignored Tim and spoke to Leah for a little bit, then pointed her to his room. She smirked at me and walked into his room, closing the door behind her.

“W-what just happened, Aaron?” Tim asked.

“You’ve never had sex with a girl before, right?”

Tim’s face flushed, but I could tell he was starting to get excited. After about a day of not getting any release, and then seeing a hot girl walk into his bedroom, I think I could predict what he was thinking.

“N-no…” he responded shyly.

“Well, today’s the day, my friend.” I gave him a rough slap on the back.

His face lit up. “Really? Hell yeah! Then let’s get this thing off me so I can get some!”

“Just hold on, kid,” I pushed him towards him room.

“W-wait, Aaron, you have to take this thing off of me first!”

“Don’t worry about it,” I reassured him and kept pushing him towards his room.

I opened the door. Leah was there, standing, naked. However, she had her back to us. Tim’s eyes practically bulged out of his head. I think it was safe to assume that this was the first time he’d ever even seen a naked girl in person. Now he was urgently whispering to me, demanding that I take his cage off. I could hear the strain in his voice.

“Tim, why don’t you get those annoying clothes off for me?” Leah asked. She was still facing the other way, only turning her head to look at us. This girl was so hot. It took all of my restraint not to move to her.

Tim looked at her, then looked at me. The poor kid was confused as hell. I just nodded and told him to do as told. Slowly, a shirt came off, then pants, followed by a very hesitant removal of his boxers.

When part of the metal cage started to peek out, Leah didn’t notice, or at least she pretended not to. This gave Tim some more confidence and he quickened his pace.

“Now get over here and lie down on the bed. Let’s have some fun,” Leah said with a smirk.

The poor kid didn’t know what was happening, but he just did as he was told. He climbed onto the bed and laid down. All the while, Leah kept his back to him.

“Close your eyes baby, I’ll make you feel good,” she crooned.

I walked around to the head of the bed. Leah turned around. I could barely hold in my laughter. Leah sure was a beautiful girl. She had perky breasts and a really curvy and sexy body. However, right over her crotch was a massive black strap-on. It looked like Leah was nearly about to laugh as well.

Tim, being the gullible idiot he was, kept his eyes closed. My sissy slut’s little cock was hardened on the inside of the cage, straining against the metal restraints.

“I’m all nice and lubed up for you, Tim,” Leah whispered. She stroked the lubricated strap-on with her hands. Well, she wasn’t lying!

She got onto the bed and kneeled in between Tim’s legs. Quickly, she grabbed his ankles and lifted them up over her shoulders. At the same time, I grabbed onto his wrists and held them down over his head.

Now, Tim decided to open his eyes to see what was happening. He lifted his head to see the big dildo at the entrance of his asshole. I couldn’t believe how gullible my sissy slave was.

“Oh, no, no, please, don’t do this!” He started screaming.

“Oh, you should be excited, Tim. It’s your first time having sex with a girl after all,” Leah’s seductive voice was full of cruelty.

My own cock was straining against the inside of my pants, but I wanted to let Leah have her fun.

“Do you remember, bitch, what you did to me?” Leah’s voice was full of hatred. It seemed that Tim didn’t know what she was talking about. That made sense, since he didn’t even recognize her. “It was at a party a few months ago. You were probably just following Aaron around like you always do. And I don’t know if you were high or drunk or whatever, but you started feeling me up.”

As she said that, she reached one of her hands down to the chastity cage. She rubbed his restrained cock, which was still hard. Then she cupped his balls in her hand. She started squeezing them lightly.

Tim winced from the slight discomfort. “Please, Leah, I’m so s-sorry, I-I really didn’t mean it…”

“It didn’t seem like it at the time, bitch,” Leah kept squeezing his small balls. “Because you actually pulled me into a bedroom and pushed me back, kinda like what I’m doing to you know.”

My little sissy didn’t try to get out anymore. He was just completely still, sweating and breathing hard due to the pain from Leah’s grip.

“L-look, Leah, p-please, s-stop it. I’m really s-sorry about what I did…” he whispered.

Leah ignored him. “It was a good thing Aaron came along when he did.” She looked at me and gave me a tired smile. “Or else you might’ve done something even worse.”

With that, Leah started to push the strap-on into Tim’s asshole. She still held onto his balls, but it seemed like she was loosening her grip. Tim’s face was red, and I could see his eyes watering up. I didn’t know if it was from humiliation or guilt, or both, but I didn’t feel bad for him after I heard Leah’s story. It was true that I stopped him from doing anything more to Leah, but I couldn’t imagine how many other girls he had also done this to, without anyone to stop him.

Once Leah was able to push the strap-on inside about halfway, she slammed the rest of it into Tim’s asshole with a grunt.

“Ahh!” Tim screamed. “Leah! I’m sorry! Please! Don’t do this!” These begs were followed by Tim’s and Leah’s heavy breathing.

“Look at you, bitch. You’re pathetic. You’re not a man, but you’re not a woman. You’re just a little sissy bitch.” Leah leaned in close to his and spit on him, causing him to flinch and shut his eyes.

Leah regained her posture and started pumping the strap-on into my sissy’s asshole. Despite everything that had just happened, his little cock was still as hard as it could get inside the cage. Leah pulled out, then slammed back in. Every time she thrust in, I watched her boobs shake up and down, while the flesh of Tim’s calves and ass jiggled.

I couldn’t take it anymore. My own cock was about to burst out of my pants. I motioned for Leah to move Tim a little bit, and turned him so that now his head was hanging over the edge of the bed. I was still holding his hands while Leah held his legs up. I held onto both of Tim’s wrists with one hand and used my free hand to remove my pants. Tim had his head hanging over the side of the bed, with his eyes closed.

Without warning, I shoved my freed cock onto his lips. At this point, I couldn’t see his facial reaction, but I could feel him thrashing his head around, underneath my cock.

“Open wide and take that cock like the sissy bitch you are!” Leah ordered. She started squeezing his balls again.

Tim did value his balls, so he did as she told.

“If Aaron feels any teeth, then I swear I will rip your balls off, bitch!” Leah yelled at him. I grinned. Leah was definitely enjoying this.

My cock was also very satisfied. My roommate’s warm and wet mouth surrounded my rock-hard member. I groaned in pleasure. I pushed my cock further, and my tip hit the back of his throat. That didn’t stop me, though. There was still about a quarter of my cock exposed to the cold air.

I thrust my hips forward. I nearly came just from that. The top of Tim’s throat clenched around my sensitive tip. I felt choking, but I didn’t care. I could feel some slight scratching on the top of my cock from Tim’s teeth. I warned him about that, and I could tell that Leah was tightening her grip. My little sissy learned that he could wrap his lips around his teeth to avoid any more trouble. I pulled my cock out of his mouth, but before he could finish taking a deep breath, I thrust it in again. Once again, there was more choking and groaning.

This was a real sight. Just a few days ago, Tim was a sexist, arrogant asshole of a roommate. Now, he was lying in his bed, being penetrated from his asshole and his mouth.

I started thrusting at the rate that Leah was, and we got into a rhythm. We both slammed in deep at the same time, then pulled out. We slammed in deep again, and pulled out. We repeated this process, while Tim was unable to do anything but lie there and take the punishment. As I was getting close to cumming, I saw a glob of pre-cum ooze out of Tim’s little cock and out of the cage, landing on his flat belly. Leah saw this, too, and started thrusting faster.

“Oh, fuck, I’m getting close…” I groaned. I pulled my cock out of my sissy’s mouth and started to jack off. Before Tim could react, I shot my load all over his face. My several thick ropes of cum covered his nose, eyes, cheeks, and lips. I could see that Tim did close his mouth, but I didn’t care. My goal was to humiliate the hell out of him, and that definitely worked.

Leah also pulled the strap-on out of Tim’s asshole. She let go of his legs, and they just dropped onto the bed. I pushed my sissy onto the bed so his head was no longer hanging off the side.

“P-please… I have to cum… just take this cage off of me so I can cum…” I loved hearing my sissy beg. But I didn’t plan on doing anything he asked of me.

“Pathetic,” Leah spat. She wasn’t angry anymore, but she that didn’t mean she was ready to let things go. Leah grabbed Tim by the throat. She slapped him on the face, which caused some of my cum to go flying. I found that rather amusing.

“I’m going to make sure that you never do something like that again. I heard your apology, but I don’t really feel like that was enough,” Leah’s hand was now covered in my cum, so she just smeared it on Tim’s belly, mixing it with the small puddle of Tim’s pre-cum that had formed. “I’m probably going to have to spend some more time with you to make sure that you really meant what you said.”

With that, Leah walked away from Tim and started to get dressed and pack her things away. She was pretty fierce.

My roommate lay on his bed, cock twitching in the cage. He didn’t try to get himself off this time, but I could tell he was debating it. He kept having to blink cum out of his eyes that dripped in, which I found funny. “Well, you really messed with the wrong girl, kid,” I scolded.

Leah left the room. I heard her open the door to our apartment. It slammed shut behind her, leaving me and my roommate together. I turned around for a moment, then looked back to see that Tim was staring at me. He immediately turned away, face reddening.

I put my clothes back on. Tim was lying on the bed, silently sobbing. I realized that night had already fallen. What a crazy 24 hours it had been.

This was going to be a lot of fun.

---

I looked into Tim’s room. There was just enough light shining through the window to outline my little sissy’s chest moving up and down. He was pretty much in the same position I left him, lying on his back with his arms tied up above him.

I walked over to the bed to look at my sissy. There was dried drool coming from his mouth and dried tears in the corners of his eyes.

I guess I should wake him up.

“Hey, wakey wakey!” I slapped him lightly on the face.

His eyes slowly opened. At first, he seemed to have no idea where he was or what happened to him. I stepped back a bit as thrashed about trying to get out of his restraints.

“What the fuck is going on?” He yelled at me, then remembered what had happened last night. His body went limp.

“Did you sleep well?” I asked jokingly.

It seemed like my little sissy didn’t want to look at me. I could see his face turning red.

“I need to use the bathroom,” he whispered.

“Sure thing,” I untied his arms.

He sat up, rotating his hands and rubbing his wrists, which now had red marks around them. I didn’t tie the ropes very tight, so he was probably trying to get out of them overnight.

“C-can you take this off, too?” He asked, shamefully pointing at the chastity cage that was restraining his little penis.

However, this chastity device was like a metal cage, with a hole at the end that allowed for easy use. It could also be cleaned while it was being worn, so I theoretically never had to take it off.

“Fortunately, there’s no need to take it off. The design is actually perfect for using the bathroom and cleaning, as well,” I smirked evilly.

He looked at me like he wanted to kill me. It was understandable.

“I can see you want to say something,” I noted. “I’ll let you say whatever you want and I won’t punish you.”

“Fuck you, you piece of shit!” He screamed. “Get this fucking thing off me!”

I chuckled at that. It was good to see there was still fight in him. It would only be more satisfying when I broke him.

“Well, I’ll take it off when I think you deserve it.” I waited there while he fumed. “Didn’t you say you have to go to the bathroom?”

With that, he left his room.

I called out after him, “You should hurry up, you don’t want to be late to your classes!”

I left his room as well. The sissy took about half an hour in the bathroom. As he got dressed, he demanded one more time that I take the cage off him, but I denied. I just told him to get back earlier today. I don’t think I had to worry about him telling anyone about what I had done to him. There’s no way his dignity would allow him to tell someone that he’d been taken like a bitch. I laughed at the thought.

“I have a surprise for you when you get back.”

=====

It was about 6 o’clock when Tim got back. It was still pretty late, but early for him.

I was in my room when I heard the apartment door open.

“Hey, Aaron, where the hell are you?” He shouted. “You said you would take this thing off me!”

He burst into my room, demanding that I take his chastity cage off.

“Alright, alright, just hold on a sec.”

I stood up and walked out of my room. Tim followed me. I sat down on the couch and opened up my phone. Tim stared at me as I just sat on the couch, ignoring him. His face was turning red, and I could very clearly see that he was starting to get mad. Strange, even though I had complete control over him, he was acting like he was the boss.

“What the fuck are you waiting for, Aaron!” He demanded. I smiled, hearing the desperation behind his anger.

At that moment, there was a knock on our door. Tim looked confused as I told him to get it.

Tim walked over to the door and opened it, revealing a girl on the other side. She wore yoga pants and a tight t-shirt that outlined her curvy figure. She had blond hair and slightly tanned skin. On her back was a small black backpack. This girl was actually shorter than Tim, which was surprising.

Tim looked at the pretty girl, baffled. I could see his face was now red not because of anger, but embarrassment.

Normally, Tim would’ve wasted no time hitting on this girl. I guess the chastity cage really didn’t put him in the mood.

“So, you’re Tim, right?” She asked. Tim responded with a very audible gulp and a quick head nod.

She then brushed past him into the apartment. I stood to greet her.

“Hey Aaron!” She greeted me.

“Hey Leah,” I responded.

Meanwhile, Tim closed the door and looked at me. I ignored Tim and spoke to Leah for a little bit, then pointed her to his room. She smirked at me and walked into his room, closing the door behind her.

“W-what just happened, Aaron?” Tim asked.

“You’ve never had sex with a girl before, right?”

Tim’s face flushed, but I could tell he was starting to get excited. After about a day of not getting any release, and then seeing a hot girl walk into his bedroom, I think I could predict what he was thinking.

“N-no…” he responded shyly.

“Well, today’s the day, my friend.” I gave him a rough slap on the back.

His face lit up. “Really? Hell yeah! Then let’s get this thing off me so I can get some!”

“Just hold on, kid,” I pushed him towards him room.

“W-wait, Aaron, you have to take this thing off of me first!”

“Don’t worry about it,” I reassured him and kept pushing him towards his room.

I opened the door. Leah was there, standing, naked. However, she had her back to us. Tim’s eyes practically bulged out of his head. I think it was safe to assume that this was the first time he’d ever even seen a naked girl in person. Now he was urgently whispering to me, demanding that I take his cage off. I could hear the strain in his voice.

“Tim, why don’t you get those annoying clothes off for me?” Leah asked. She was still facing the other way, only turning her head to look at us. This girl was so hot. It took all of my restraint not to move to her.

Tim looked at her, then looked at me. The poor kid was confused as hell. I just nodded and told him to do as told. Slowly, a shirt came off, then pants, followed by a very hesitant removal of his boxers.

When part of the metal cage started to peek out, Leah didn’t notice, or at least she pretended not to. This gave Tim some more confidence and he quickened his pace.

“Now get over here and lie down on the bed. Let’s have some fun,” Leah said with a smirk.

The poor kid didn’t know what was happening, but he just did as he was told. He climbed onto the bed and laid down. All the while, Leah kept his back to him.

“Close your eyes baby, I’ll make you feel good,” she crooned.

I walked around to the head of the bed. Leah turned around. I could barely hold in my laughter. Leah sure was a beautiful girl. She had perky breasts and a really curvy and sexy body. However, right over her crotch was a massive black strap-on. It looked like Leah was nearly about to laugh as well.

Tim, being the gullible idiot he was, kept his eyes closed. My sissy slut’s little cock was hardened on the inside of the cage, straining against the metal restraints.

“I’m all nice and lubed up for you, Tim,” Leah whispered. She stroked the lubricated strap-on with her hands. Well, she wasn’t lying!

She got onto the bed and kneeled in between Tim’s legs. Quickly, she grabbed his ankles and lifted them up over her shoulders. At the same time, I grabbed onto his wrists and held them down over his head.

Now, Tim decided to open his eyes to see what was happening. He lifted his head to see the big dildo at the entrance of his asshole. I couldn’t believe how gullible my sissy slave was.

“Oh, no, no, please, don’t do this!” He started screaming.

“Oh, you should be excited, Tim. It’s your first time having sex with a girl after all,” Leah’s seductive voice was full of cruelty.

My own cock was straining against the inside of my pants, but I wanted to let Leah have her fun.

“Do you remember, bitch, what you did to me?” Leah’s voice was full of hatred. It seemed that Tim didn’t know what she was talking about. That made sense, since he didn’t even recognize her. “It was at a party a few months ago. You were probably just following Aaron around like you always do. And I don’t know if you were high or drunk or whatever, but you started feeling me up.”

As she said that, she reached one of her hands down to the chastity cage. She rubbed his restrained cock, which was still hard. Then she cupped his balls in her hand. She started squeezing them lightly.

Tim winced from the slight discomfort. “Please, Leah, I’m so s-sorry, I-I really didn’t mean it…”

“It didn’t seem like it at the time, bitch,” Leah kept squeezing his small balls. “Because you actually pulled me into a bedroom and pushed me back, kinda like what I’m doing to you know.”

My little sissy didn’t try to get out anymore. He was just completely still, sweating and breathing hard due to the pain from Leah’s grip.

“L-look, Leah, p-please, s-stop it. I’m really s-sorry about what I did…” he whispered.

Leah ignored him. “It was a good thing Aaron came along when he did.” She looked at me and gave me a tired smile. “Or else you might’ve done something even worse.”

With that, Leah started to push the strap-on into Tim’s asshole. She still held onto his balls, but it seemed like she was loosening her grip. Tim’s face was red, and I could see his eyes watering up. I didn’t know if it was from humiliation or guilt, or both, but I didn’t feel bad for him after I heard Leah’s story. It was true that I stopped him from doing anything more to Leah, but I couldn’t imagine how many other girls he had also done this to, without anyone to stop him.

Once Leah was able to push the strap-on inside about halfway, she slammed the rest of it into Tim’s asshole with a grunt.

“Ahh!” Tim screamed. “Leah! I’m sorry! Please! Don’t do this!” These begs were followed by Tim’s and Leah’s heavy breathing.

“Look at you, bitch. You’re pathetic. You’re not a man, but you’re not a woman. You’re just a little sissy bitch.” Leah leaned in close to his and spit on him, causing him to flinch and shut his eyes.

Leah regained her posture and started pumping the strap-on into my sissy’s asshole. Despite everything that had just happened, his little cock was still as hard as it could get inside the cage. Leah pulled out, then slammed back in. Every time she thrust in, I watched her boobs shake up and down, while the flesh of Tim’s calves and ass jiggled.

I couldn’t take it anymore. My own cock was about to burst out of my pants. I motioned for Leah to move Tim a little bit, and turned him so that now his head was hanging over the edge of the bed. I was still holding his hands while Leah held his legs up. I held onto both of Tim’s wrists with one hand and used my free hand to remove my pants. Tim had his head hanging over the side of the bed, with his eyes closed.

Without warning, I shoved my freed cock onto his lips. At this point, I couldn’t see his facial reaction, but I could feel him thrashing his head around, underneath my cock.

“Open wide and take that cock like the sissy bitch you are!” Leah ordered. She started squeezing his balls again.

Tim did value his balls, so he did as she told.

“If Aaron feels any teeth, then I swear I will rip your balls off, bitch!” Leah yelled at him. I grinned. Leah was definitely enjoying this.

My cock was also very satisfied. My roommate’s warm and wet mouth surrounded my rock-hard member. I groaned in pleasure. I pushed my cock further, and my tip hit the back of his throat. That didn’t stop me, though. There was still about a quarter of my cock exposed to the cold air.

I thrust my hips forward. I nearly came just from that. The top of Tim’s throat clenched around my sensitive tip. I felt choking, but I didn’t care. I could feel some slight scratching on the top of my cock from Tim’s teeth. I warned him about that, and I could tell that Leah was tightening her grip. My little sissy learned that he could wrap his lips around his teeth to avoid any more trouble. I pulled my cock out of his mouth, but before he could finish taking a deep breath, I thrust it in again. Once again, there was more choking and groaning.

This was a real sight. Just a few days ago, Tim was a sexist, arrogant asshole of a roommate. Now, he was lying in his bed, being penetrated from his asshole and his mouth.

I started thrusting at the rate that Leah was, and we got into a rhythm. We both slammed in deep at the same time, then pulled out. We slammed in deep again, and pulled out. We repeated this process, while Tim was unable to do anything but lie there and take the punishment. As I was getting close to cumming, I saw a glob of pre-cum ooze out of Tim’s little cock and out of the cage, landing on his flat belly. Leah saw this, too, and started thrusting faster.

“Oh, fuck, I’m getting close…” I groaned. I pulled my cock out of my sissy’s mouth and started to jack off. Before Tim could react, I shot my load all over his face. My several thick ropes of cum covered his nose, eyes, cheeks, and lips. I could see that Tim did close his mouth, but I didn’t care. My goal was to humiliate the hell out of him, and that definitely worked.

Leah also pulled the strap-on out of Tim’s asshole. She let go of his legs, and they just dropped onto the bed. I pushed my sissy onto the bed so his head was no longer hanging off the side.

“P-please… I have to cum… just take this cage off of me so I can cum…” I loved hearing my sissy beg. But I didn’t plan on doing anything he asked of me.

“Pathetic,” Leah spat. She wasn’t angry anymore, but she that didn’t mean she was ready to let things go. Leah grabbed Tim by the throat. She slapped him on the face, which caused some of my cum to go flying. I found that rather amusing.

“I’m going to make sure that you never do something like that again. I heard your apology, but I don’t really feel like that was enough,” Leah’s hand was now covered in my cum, so she just smeared it on Tim’s belly, mixing it with the small puddle of Tim’s pre-cum that had formed. “I’m probably going to have to spend some more time with you to make sure that you really meant what you said.”

With that, Leah walked away from Tim and started to get dressed and pack her things away. She was pretty fierce.

My roommate lay on his bed, cock twitching in the cage. He didn’t try to get himself off this time, but I could tell he was debating it. He kept having to blink cum out of his eyes that dripped in, which I found funny. “Well, you really messed with the wrong girl, kid,” I scolded.

Leah left the room. I heard her open the door to our apartment. It slammed shut behind her, leaving me and my roommate together. I turned around for a moment, then looked back to see that Tim was staring at me. He immediately turned away, face reddening.

I put my clothes back on. Tim was lying on the bed, silently sobbing. I realized that night had already fallen. What a crazy 24 hours it had been.

This was going to be a lot of fun.

---

I looked into Tim’s room. There was just enough light shining through the window to outline my little sissy’s chest moving up and down. He was pretty much in the same position I left him, lying on his back with his arms tied up above him.

I walked over to the bed to look at my sissy. There was dried drool coming from his mouth and dried tears in the corners of his eyes.

I guess I should wake him up.

“Hey, wakey wakey!” I slapped him lightly on the face.

His eyes slowly opened. At first, he seemed to have no idea where he was or what happened to him. I stepped back a bit as thrashed about trying to get out of his restraints.

“What the fuck is going on?” He yelled at me, then remembered what had happened last night. His body went limp.

“Did you sleep well?” I asked jokingly.

It seemed like my little sissy didn’t want to look at me. I could see his face turning red.

“I need to use the bathroom,” he whispered.

“Sure thing,” I untied his arms.

He sat up, rotating his hands and rubbing his wrists, which now had red marks around them. I didn’t tie the ropes very tight, so he was probably trying to get out of them overnight.

“C-can you take this off, too?” He asked, shamefully pointing at the chastity cage that was restraining his little penis.

However, this chastity device was like a metal cage, with a hole at the end that allowed for easy use. It could also be cleaned while it was being worn, so I theoretically never had to take it off.

“Fortunately, there’s no need to take it off. The design is actually perfect for using the bathroom and cleaning, as well,” I smirked evilly.

He looked at me like he wanted to kill me. It was understandable.

“I can see you want to say something,” I noted. “I’ll let you say whatever you want and I won’t punish you.”

“Fuck you, you piece of shit!” He screamed. “Get this fucking thing off me!”

I chuckled at that. It was good to see there was still fight in him. It would only be more satisfying when I broke him.

“Well, I’ll take it off when I think you deserve it.” I waited there while he fumed. “Didn’t you say you have to go to the bathroom?”

With that, he left his room.

I called out after him, “You should hurry up, you don’t want to be late to your classes!”

I left his room as well. The sissy took about half an hour in the bathroom. As he got dressed, he demanded one more time that I take the cage off him, but I denied. I just told him to get back earlier today. I don’t think I had to worry about him telling anyone about what I had done to him. There’s no way his dignity would allow him to tell someone that he’d been taken like a bitch. I laughed at the thought.

“I have a surprise for you when you get back.”

=====

It was about 6 o’clock when Tim got back. It was still pretty late, but early for him.

I was in my room when I heard the apartment door open.

“Hey, Aaron, where the hell are you?” He shouted. “You said you would take this thing off me!”

He burst into my room, demanding that I take his chastity cage off.

“Alright, alright, just hold on a sec.”

I stood up and walked out of my room. Tim followed me. I sat down on the couch and opened up my phone. Tim stared at me as I just sat on the couch, ignoring him. His face was turning red, and I could very clearly see that he was starting to get mad. Strange, even though I had complete control over him, he was acting like he was the boss.

“What the fuck are you waiting for, Aaron!” He demanded. I smiled, hearing the desperation behind his anger.

At that moment, there was a knock on our door. Tim looked confused as I told him to get it.

Tim walked over to the door and opened it, revealing a girl on the other side. She wore yoga pants and a tight t-shirt that outlined her curvy figure. She had blond hair and slightly tanned skin. On her back was a small black backpack. This girl was actually shorter than Tim, which was surprising.

Tim looked at the pretty girl, baffled. I could see his face was now red not because of anger, but embarrassment.

Normally, Tim would’ve wasted no time hitting on this girl. I guess the chastity cage really didn’t put him in the mood.

“So, you’re Tim, right?” She asked. Tim responded with a very audible gulp and a quick head nod.

She then brushed past him into the apartment. I stood to greet her.

“Hey Aaron!” She greeted me.

“Hey Leah,” I responded.

Meanwhile, Tim closed the door and looked at me. I ignored Tim and spoke to Leah for a little bit, then pointed her to his room. She smirked at me and walked into his room, closing the door behind her.

“W-what just happened, Aaron?” Tim asked.

“You’ve never had sex with a girl before, right?”

Tim’s face flushed, but I could tell he was starting to get excited. After about a day of not getting any release, and then seeing a hot girl walk into his bedroom, I think I could predict what he was thinking.

“N-no…” he responded shyly.

“Well, today’s the day, my friend.” I gave him a rough slap on the back.

His face lit up. “Really? Hell yeah! Then let’s get this thing off me so I can get some!”

“Just hold on, kid,” I pushed him towards him room.

“W-wait, Aaron, you have to take this thing off of me first!”

“Don’t worry about it,” I reassured him and kept pushing him towards his room.

I opened the door. Leah was there, standing, naked. However, she had her back to us. Tim’s eyes practically bulged out of his head. I think it was safe to assume that this was the first time he’d ever even seen a naked girl in person. Now he was urgently whispering to me, demanding that I take his cage off. I could hear the strain in his voice.

“Tim, why don’t you get those annoying clothes off for me?” Leah asked. She was still facing the other way, only turning her head to look at us. This girl was so hot. It took all of my restraint not to move to her.

Tim looked at her, then looked at me. The poor kid was confused as hell. I just nodded and told him to do as told. Slowly, a shirt came off, then pants, followed by a very hesitant removal of his boxers.

When part of the metal cage started to peek out, Leah didn’t notice, or at least she pretended not to. This gave Tim some more confidence and he quickened his pace.

“Now get over here and lie down on the bed. Let’s have some fun,” Leah said with a smirk.

The poor kid didn’t know what was happening, but he just did as he was told. He climbed onto the bed and laid down. All the while, Leah kept his back to him.

“Close your eyes baby, I’ll make you feel good,” she crooned.

I walked around to the head of the bed. Leah turned around. I could barely hold in my laughter. Leah sure was a beautiful girl. She had perky breasts and a really curvy and sexy body. However, right over her crotch was a massive black strap-on. It looked like Leah was nearly about to laugh as well.

Tim, being the gullible idiot he was, kept his eyes closed. My sissy slut’s little cock was hardened on the inside of the cage, straining against the metal restraints.

“I’m all nice and lubed up for you, Tim,” Leah whispered. She stroked the lubricated strap-on with her hands. Well, she wasn’t lying!

She got onto the bed and kneeled in between Tim’s legs. Quickly, she grabbed his ankles and lifted them up over her shoulders. At the same time, I grabbed onto his wrists and held them down over his head.

Now, Tim decided to open his eyes to see what was happening. He lifted his head to see the big dildo at the entrance of his asshole. I couldn’t believe how gullible my sissy slave was.

“Oh, no, no, please, don’t do this!” He started screaming.

“Oh, you should be excited, Tim. It’s your first time having sex with a girl after all,” Leah’s seductive voice was full of cruelty.

My own cock was straining against the inside of my pants, but I wanted to let Leah have her fun.

“Do you remember, bitch, what you did to me?” Leah’s voice was full of hatred. It seemed that Tim didn’t know what she was talking about. That made sense, since he didn’t even recognize her. “It was at a party a few months ago. You were probably just following Aaron around like you always do. And I don’t know if you were high or drunk or whatever, but you started feeling me up.”

As she said that, she reached one of her hands down to the chastity cage. She rubbed his restrained cock, which was still hard. Then she cupped his balls in her hand. She started squeezing them lightly.

Tim winced from the slight discomfort. “Please, Leah, I’m so s-sorry, I-I really didn’t mean it…”

“It didn’t seem like it at the time, bitch,” Leah kept squeezing his small balls. “Because you actually pulled me into a bedroom and pushed me back, kinda like what I’m doing to you know.”

My little sissy didn’t try to get out anymore. He was just completely still, sweating and breathing hard due to the pain from Leah’s grip.

“L-look, Leah, p-please, s-stop it. I’m really s-sorry about what I did…” he whispered.

Leah ignored him. “It was a good thing Aaron came along when he did.” She looked at me and gave me a tired smile. “Or else you might’ve done something even worse.”

With that, Leah started to push the strap-on into Tim’s asshole. She still held onto his balls, but it seemed like she was loosening her grip. Tim’s face was red, and I could see his eyes watering up. I didn’t know if it was from humiliation or guilt, or both, but I didn’t feel bad for him after I heard Leah’s story. It was true that I stopped him from doing anything more to Leah, but I couldn’t imagine how many other girls he had also done this to, without anyone to stop him.

Once Leah was able to push the strap-on inside about halfway, she slammed the rest of it into Tim’s asshole with a grunt.

“Ahh!” Tim screamed. “Leah! I’m sorry! Please! Don’t do this!” These begs were followed by Tim’s and Leah’s heavy breathing.

“Look at you, bitch. You’re pathetic. You’re not a man, but you’re not a woman. You’re just a little sissy bitch.” Leah leaned in close to his and spit on him, causing him to flinch and shut his eyes.

Leah regained her posture and started pumping the strap-on into my sissy’s asshole. Despite everything that had just happened, his little cock was still as hard as it could get inside the cage. Leah pulled out, then slammed back in. Every time she thrust in, I watched her boobs shake up and down, while the flesh of Tim’s calves and ass jiggled.

I couldn’t take it anymore. My own cock was about to burst out of my pants. I motioned for Leah to move Tim a little bit, and turned him so that now his head was hanging over the edge of the bed. I was still holding his hands while Leah held his legs up. I held onto both of Tim’s wrists with one hand and used my free hand to remove my pants. Tim had his head hanging over the side of the bed, with his eyes closed.

Without warning, I shoved my freed cock onto his lips. At this point, I couldn’t see his facial reaction, but I could feel him thrashing his head around, underneath my cock.

“Open wide and take that cock like the sissy bitch you are!” Leah ordered. She started squeezing his balls again.

Tim did value his balls, so he did as she told.

“If Aaron feels any teeth, then I swear I will rip your balls off, bitch!” Leah yelled at him. I grinned. Leah was definitely enjoying this.

My cock was also very satisfied. My roommate’s warm and wet mouth surrounded my rock-hard member. I groaned in pleasure. I pushed my cock further, and my tip hit the back of his throat. That didn’t stop me, though. There was still about a quarter of my cock exposed to the cold air.

I thrust my hips forward. I nearly came just from that. The top of Tim’s throat clenched around my sensitive tip. I felt choking, but I didn’t care. I could feel some slight scratching on the top of my cock from Tim’s teeth. I warned him about that, and I could tell that Leah was tightening her grip. My little sissy learned that he could wrap his lips around his teeth to avoid any more trouble. I pulled my cock out of his mouth, but before he could finish taking a deep breath, I thrust it in again. Once again, there was more choking and groaning.

This was a real sight. Just a few days ago, Tim was a sexist, arrogant asshole of a roommate. Now, he was lying in his bed, being penetrated from his asshole and his mouth.

I started thrusting at the rate that Leah was, and we got into a rhythm. We both slammed in deep at the same time, then pulled out. We slammed in deep again, and pulled out. We repeated this process, while Tim was unable to do anything but lie there and take the punishment. As I was getting close to cumming, I saw a glob of pre-cum ooze out of Tim’s little cock and out of the cage, landing on his flat belly. Leah saw this, too, and started thrusting faster.

“Oh, fuck, I’m getting close…” I groaned. I pulled my cock out of my sissy’s mouth and started to jack off. Before Tim could react, I shot my load all over his face. My several thick ropes of cum covered his nose, eyes, cheeks, and lips. I could see that Tim did close his mouth, but I didn’t care. My goal was to humiliate the hell out of him, and that definitely worked.

Leah also pulled the strap-on out of Tim’s asshole. She let go of his legs, and they just dropped onto the bed. I pushed my sissy onto the bed so his head was no longer hanging off the side.

“P-please… I have to cum… just take this cage off of me so I can cum…” I loved hearing my sissy beg. But I didn’t plan on doing anything he asked of me.

“Pathetic,” Leah spat. She wasn’t angry anymore, but she that didn’t mean she was ready to let things go. Leah grabbed Tim by the throat. She slapped him on the face, which caused some of my cum to go flying. I found that rather amusing.

“I’m going to make sure that you never do something like that again. I heard your apology, but I don’t really feel like that was enough,” Leah’s hand was now covered in my cum, so she just smeared it on Tim’s belly, mixing it with the small puddle of Tim’s pre-cum that had formed. “I’m probably going to have to spend some more time with you to make sure that you really meant what you said.”

With that, Leah walked away from Tim and started to get dressed and pack her things away. She was pretty fierce.

My roommate lay on his bed, cock twitching in the cage. He didn’t try to get himself off this time, but I could tell he was debating it. He kept having to blink cum out of his eyes that dripped in, which I found funny. “Well, you really messed with the wrong girl, kid,” I scolded.

Leah left the room. I heard her open the door to our apartment. It slammed shut behind her, leaving me and my roommate together. I turned around for a moment, then looked back to see that Tim was staring at me. He immediately turned away, face reddening.

I put my clothes back on. Tim was lying on the bed, silently sobbing. I realized that night had already fallen. What a crazy 24 hours it had been.

This was going to be a lot of fun.

---

I looked into Tim’s room. There was just enough light shining through the window to outline my little sissy’s chest moving up and down. He was pretty much in the same position I left him, lying on his back with his arms tied up above him.

I walked over to the bed to look at my sissy. There was dried drool coming from his mouth and dried tears in the corners of his eyes.

I guess I should wake him up.

“Hey, wakey wakey!” I slapped him lightly on the face.

His eyes slowly opened. At first, he seemed to have no idea where he was or what happened to him. I stepped back a bit as thrashed about trying to get out of his restraints.

“What the fuck is going on?” He yelled at me, then remembered what had happened last night. His body went limp.

“Did you sleep well?” I asked jokingly.

It seemed like my little sissy didn’t want to look at me. I could see his face turning red.

“I need to use the bathroom,” he whispered.

“Sure thing,” I untied his arms.

He sat up, rotating his hands and rubbing his wrists, which now had red marks around them. I didn’t tie the ropes very tight, so he was probably trying to get out of them overnight.

“C-can you take this off, too?” He asked, shamefully pointing at the chastity cage that was restraining his little penis.

However, this chastity device was like a metal cage, with a hole at the end that allowed for easy use. It could also be cleaned while it was being worn, so I theoretically never had to take it off.

“Fortunately, there’s no need to take it off. The design is actually perfect for using the bathroom and cleaning, as well,” I smirked evilly.

He looked at me like he wanted to kill me. It was understandable.

“I can see you want to say something,” I noted. “I’ll let you say whatever you want and I won’t punish you.”

“Fuck you, you piece of shit!” He screamed. “Get this fucking thing off me!”

I chuckled at that. It was good to see there was still fight in him. It would only be more satisfying when I broke him.

“Well, I’ll take it off when I think you deserve it.” I waited there while he fumed. “Didn’t you say you have to go to the bathroom?”

With that, he left his room.

I called out after him, “You should hurry up, you don’t want to be late to your classes!”

I left his room as well. The sissy took about half an hour in the bathroom. As he got dressed, he demanded one more time that I take the cage off him, but I denied. I just told him to get back earlier today. I don’t think I had to worry about him telling anyone about what I had done to him. There’s no way his dignity would allow him to tell someone that he’d been taken like a bitch. I laughed at the thought.

“I have a surprise for you when you get back.”

=====

It was about 6 o’clock when Tim got back. It was still pretty late, but early for him.

I was in my room when I heard the apartment door open.

“Hey, Aaron, where the hell are you?” He shouted. “You said you would take this thing off me!”

He burst into my room, demanding that I take his chastity cage off.

“Alright, alright, just hold on a sec.”

I stood up and walked out of my room. Tim followed me. I sat down on the couch and opened up my phone. Tim stared at me as I just sat on the couch, ignoring him. His face was turning red, and I could very clearly see that he was starting to get mad. Strange, even though I had complete control over him, he was acting like he was the boss.

“What the fuck are you waiting for, Aaron!” He demanded. I smiled, hearing the desperation behind his anger.

At that moment, there was a knock on our door. Tim looked confused as I told him to get it.

Tim walked over to the door and opened it, revealing a girl on the other side. She wore yoga pants and a tight t-shirt that outlined her curvy figure. She had blond hair and slightly tanned skin. On her back was a small black backpack. This girl was actually shorter than Tim, which was surprising.

Tim looked at the pretty girl, baffled. I could see his face was now red not because of anger, but embarrassment.

Normally, Tim would’ve wasted no time hitting on this girl. I guess the chastity cage really didn’t put him in the mood.

“So, you’re Tim, right?” She asked. Tim responded with a very audible gulp and a quick head nod.

She then brushed past him into the apartment. I stood to greet her.

“Hey Aaron!” She greeted me.

“Hey Leah,” I responded.

Meanwhile, Tim closed the door and looked at me. I ignored Tim and spoke to Leah for a little bit, then pointed her to his room. She smirked at me and walked into his room, closing the door behind her.

“W-what just happened, Aaron?” Tim asked.

“You’ve never had sex with a girl before, right?”

Tim’s face flushed, but I could tell he was starting to get excited. After about a day of not getting any release, and then seeing a hot girl walk into his bedroom, I think I could predict what he was thinking.

“N-no…” he responded shyly.

“Well, today’s the day, my friend.” I gave him a rough slap on the back.

His face lit up. “Really? Hell yeah! Then let’s get this thing off me so I can get some!”

“Just hold on, kid,” I pushed him towards him room.

“W-wait, Aaron, you have to take this thing off of me first!”

“Don’t worry about it,” I reassured him and kept pushing him towards his room.

I opened the door. Leah was there, standing, naked. However, she had her back to us. Tim’s eyes practically bulged out of his head. I think it was safe to assume that this was the first time he’d ever even seen a naked girl in person. Now he was urgently whispering to me, demanding that I take his cage off. I could hear the strain in his voice.

“Tim, why don’t you get those annoying clothes off for me?” Leah asked. She was still facing the other way, only turning her head to look at us. This girl was so hot. It took all of my restraint not to move to her.

Tim looked at her, then looked at me. The poor kid was confused as hell. I just nodded and told him to do as told. Slowly, a shirt came off, then pants, followed by a very hesitant removal of his boxers.

When part of the metal cage started to peek out, Leah didn’t notice, or at least she pretended not to. This gave Tim some more confidence and he quickened his pace.

“Now get over here and lie down on the bed. Let’s have some fun,” Leah said with a smirk.

The poor kid didn’t know what was happening, but he just did as he was told. He climbed onto the bed and laid down. All the while, Leah kept his back to him.

“Close your eyes baby, I’ll make you feel good,” she crooned.

I walked around to the head of the bed. Leah turned around. I could barely hold in my laughter. Leah sure was a beautiful girl. She had perky breasts and a really curvy and sexy body. However, right over her crotch was a massive black strap-on. It looked like Leah was nearly about to laugh as well.

Tim, being the gullible idiot he was, kept his eyes closed. My sissy slut’s little cock was hardened on the inside of the cage, straining against the metal restraints.

“I’m all nice and lubed up for you, Tim,” Leah whispered. She stroked the lubricated strap-on with her hands. Well, she wasn’t lying!

She got onto the bed and kneeled in between Tim’s legs. Quickly, she grabbed his ankles and lifted them up over her shoulders. At the same time, I grabbed onto his wrists and held them down over his head.

Now, Tim decided to open his eyes to see what was happening. He lifted his head to see the big dildo at the entrance of his asshole. I couldn’t believe how gullible my sissy slave was.

“Oh, no, no, please, don’t do this!” He started screaming.

“Oh, you should be excited, Tim. It’s your first time having sex with a girl after all,” Leah’s seductive voice was full of cruelty.

My own cock was straining against the inside of my pants, but I wanted to let Leah have her fun.

“Do you remember, bitch, what you did to me?” Leah’s voice was full of hatred. It seemed that Tim didn’t know what she was talking about. That made sense, since he didn’t even recognize her. “It was at a party a few months ago. You were probably just following Aaron around like you always do. And I don’t know if you were high or drunk or whatever, but you started feeling me up.”

As she said that, she reached one of her hands down to the chastity cage. She rubbed his restrained cock, which was still hard. Then she cupped his balls in her hand. She started squeezing them lightly.

Tim winced from the slight discomfort. “Please, Leah, I’m so s-sorry, I-I really didn’t mean it…”

“It didn’t seem like it at the time, bitch,” Leah kept squeezing his small balls. “Because you actually pulled me into a bedroom and pushed me back, kinda like what I’m doing to you know.”

My little sissy didn’t try to get out anymore. He was just completely still, sweating and breathing hard due to the pain from Leah’s grip.

“L-look, Leah, p-please, s-stop it. I’m really s-sorry about what I did…” he whispered.

Leah ignored him. “It was a good thing Aaron came along when he did.” She looked at me and gave me a tired smile. “Or else you might’ve done something even worse.”

With that, Leah started to push the strap-on into Tim’s asshole. She still held onto his balls, but it seemed like she was loosening her grip. Tim’s face was red, and I could see his eyes watering up. I didn’t know if it was from humiliation or guilt, or both, but I didn’t feel bad for him after I heard Leah’s story. It was true that I stopped him from doing anything more to Leah, but I couldn’t imagine how many other girls he had also done this to, without anyone to stop him.

Once Leah was able to push the strap-on inside about halfway, she slammed the rest of it into Tim’s asshole with a grunt.

“Ahh!” Tim screamed. “Leah! I’m sorry! Please! Don’t do this!” These begs were followed by Tim’s and Leah’s heavy breathing.

“Look at you, bitch. You’re pathetic. You’re not a man, but you’re not a woman. You’re just a little sissy bitch.” Leah leaned in close to his and spit on him, causing him to flinch and shut his eyes.

Leah regained her posture and started pumping the strap-on into my sissy’s asshole. Despite everything that had just happened, his little cock was still as hard as it could get inside the cage. Leah pulled out, then slammed back in. Every time she thrust in, I watched her boobs shake up and down, while the flesh of Tim’s calves and ass jiggled.

I couldn’t take it anymore. My own cock was about to burst out of my pants. I motioned for Leah to move Tim a little bit, and turned him so that now his head was hanging over the edge of the bed. I was still holding his hands while Leah held his legs up. I held onto both of Tim’s wrists with one hand and used my free hand to remove my pants. Tim had his head hanging over the side of the bed, with his eyes closed.

Without warning, I shoved my freed cock onto his lips. At this point, I couldn’t see his facial reaction, but I could feel him thrashing his head around, underneath my cock.

“Open wide and take that cock like the sissy bitch you are!” Leah ordered. She started squeezing his balls again.

Tim did value his balls, so he did as she told.

“If Aaron feels any teeth, then I swear I will rip your balls off, bitch!” Leah yelled at him. I grinned. Leah was definitely enjoying this.

My cock was also very satisfied. My roommate’s warm and wet mouth surrounded my rock-hard member. I groaned in pleasure. I pushed my cock further, and my tip hit the back of his throat. That didn’t stop me, though. There was still about a quarter of my cock exposed to the cold air.

I thrust my hips forward. I nearly came just from that. The top of Tim’s throat clenched around my sensitive tip. I felt choking, but I didn’t care. I could feel some slight scratching on the top of my cock from Tim’s teeth. I warned him about that, and I could tell that Leah was tightening her grip. My little sissy learned that he could wrap his lips around his teeth to avoid any more trouble. I pulled my cock out of his mouth, but before he could finish taking a deep breath, I thrust it in again. Once again, there was more choking and groaning.

This was a real sight. Just a few days ago, Tim was a sexist, arrogant asshole of a roommate. Now, he was lying in his bed, being penetrated from his asshole and his mouth.

I started thrusting at the rate that Leah was, and we got into a rhythm. We both slammed in deep at the same time, then pulled out. We slammed in deep again, and pulled out. We repeated this process, while Tim was unable to do anything but lie there and take the punishment. As I was getting close to cumming, I saw a glob of pre-cum ooze out of Tim’s little cock and out of the cage, landing on his flat belly. Leah saw this, too, and started thrusting faster.

“Oh, fuck, I’m getting close…” I groaned. I pulled my cock out of my sissy’s mouth and started to jack off. Before Tim could react, I shot my load all over his face. My several thick ropes of cum covered his nose, eyes, cheeks, and lips. I could see that Tim did close his mouth, but I didn’t care. My goal was to humiliate the hell out of him, and that definitely worked.

Leah also pulled the strap-on out of Tim’s asshole. She let go of his legs, and they just dropped onto the bed. I pushed my sissy onto the bed so his head was no longer hanging off the side.

“P-please… I have to cum… just take this cage off of me so I can cum…” I loved hearing my sissy beg. But I didn’t plan on doing anything he asked of me.

“Pathetic,” Leah spat. She wasn’t angry anymore, but she that didn’t mean she was ready to let things go. Leah grabbed Tim by the throat. She slapped him on the face, which caused some of my cum to go flying. I found that rather amusing.

“I’m going to make sure that you never do something like that again. I heard your apology, but I don’t really feel like that was enough,” Leah’s hand was now covered in my cum, so she just smeared it on Tim’s belly, mixing it with the small puddle of Tim’s pre-cum that had formed. “I’m probably going to have to spend some more time with you to make sure that you really meant what you said.”

With that, Leah walked away from Tim and started to get dressed and pack her things away. She was pretty fierce.

My roommate lay on his bed, cock twitching in the cage. He didn’t try to get himself off this time, but I could tell he was debating it. He kept having to blink cum out of his eyes that dripped in, which I found funny. “Well, you really messed with the wrong girl, kid,” I scolded.

Leah left the room. I heard her open the door to our apartment. It slammed shut behind her, leaving me and my roommate together. I turned around for a moment, then looked back to see that Tim was staring at me. He immediately turned away, face reddening.

I put my clothes back on. Tim was lying on the bed, silently sobbing. I realized that night had already fallen. What a crazy 24 hours it had been.

This was going to be a lot of fun.

---