Turning My Roommate into a Sissy Slut Chapter 4
Introduction:
This is the fourth installment of this series. If you haven’t yet done so, please read the first three chapters. I think I’m going to end this series here, but let me know if I should continue. Feel free to leave any comments and feedback!
My roommate, Terri, was kneeling in front of me, naked and ready to serve. Just to think, only a few weeks ago, her name was Tim. Tim was an arrogant asshole that didn’t really have any idea of what the real world was like. Seeing as he was a sexist and a racist, as well as all the other negative terms I could use to describe someone, I decided to teach him a lesson.
Well, I’d say it turned out pretty well. Now, she was on her way to becoming my own little sissy slave.
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“Terri, do you remember what I told you?” I questioned.
“Y-yes, you told me that I always had to be back here by 3:00 pm on the weekdays…” her voice trailed off.
“And what time did you get back today?”
“U-um… I believe I got back a-at about…” her high-pitched voice trailed off once again, “3:20, master.”
I sighed deeply, so as to exaggerate my disappointment. Well, at least she remembered to call me ‘master’. I smiled at the thought of her seeing me as her owner. I looked down at her small cock, encased by the chastity cage I got for her. It rested in between her smooth thighs, which I’d commanded her to always keep shaven, which I was glad to see she’d been doing.
“I think I need to start punishing you for getting back so late everyday. You’ve been getting better, but you’re still breaking my rules.” I was hoping to play on her emotions a little bit. I was hoping that she was still hesitant about this whole thing so I could really break it into her. “You do want to be a good little sissy slut for me, right?”
She hesitated to answer, “I-I… y-yes, I want to be good… and I promise I won’t be late again, master. Please don’t punish me…”
I didn’t buy it. “Stand up,” I commanded.
She immediately rose to her feet. Looking down at her, she was almost a foot shorter than me, and her body looked just like a girl’s, despite being genetically male. If you didn’t see what I liked the call her little clitty, then you would assume she was a girl. I walked over to the couch and sat down, pulling Terri along with me. I roughly pulled her down so that she was bent over my knees, with her bare ass on my right and her head on my left. I placed her in the classic spanking position.
I told her, “From now on, I’m going to give you one spank for every minute you’re late. So start counting.”
“W-wait, master…” she started, but was cut off by my sharp smack on her right ass cheek. “Ah!”
“Start counting, slut!” I commanded.
“Please, it hurts, I promise I won’t be late again!” she begged.
“Good, I hope you can keep that promise.” I didn’t stop, though. I smacked her hard on the left cheek this time. “But if you don’t start counting, I’ll lose track and I’ll have to restart!”
I raised my right arm and brought it down on her right cheek once again.
“Three! That’s three!” She screamed.
I continued spanking her, alternating from side to side, until Terri managed to count to twenty in between screams and sobs. Watching her porcelain ass jiggling and slowly turning red was getting me turned on. I rubbed my hand over her smooth, round ass that looked just like a girl’s. At a certain angle it even looked like she had tits. I also told her to start growing out the hair on her head, so it was definitely believable. However, she was still able to hide it during her classes and still acted like the old Tim when in public. But that’s what I liked about it. It was our little secret.
After we finished, Terri got off of me and stood up, wincing. I stood up as well, and I could see that she had actually gotten hard from that.
“It seems your little clitty enjoyed that spanking,” I teased. I loved seeing the humiliation in her face when I called it her ‘clitty’. And since I’ve always kept it trapped in the chastity cage, she rarely got any release, making it so easy to turn her on.
“When was the last time you got to cum, Terri?” I asked.
“L-last Wednesday…” she responded, “That was the only time I got to cum with this cage on…”
“Would you like me to let you cum today, Terri?”
“Y-yes, master…” she whispered.
I chuckled. “Well, how do you suppose we go about that?” She hated this part. I’d only let her cum once with that cage on, and it was after I’d fucked her hard enough that she got stimulated enough to cum with the cage on.
“I want you to… f-fuck me… in the ass, master…” she whispered.
“You know, you really need to start talking louder, Terri. If you want something, then just say it!” I commanded.
“I want you to fuck me, master! Like how you did it the last time!”
“Mmm… no,” I responded. Despite being horny as hell, I had other plans for her. I ignored her pleas and complaints and resisted my own urges.
Instead, I commanded Terri to go to her room and look in her closet. When she came back, she was holding a slutty French maid outfit. I had to laugh aloud at that. Her face turned bright red in defiance.
“I…I…” she stuttered. It seemed Terri didn’t even know what to say. But I could tell she didn’t want to put the outfit on. Not without a little bit of a push, at least.
“Well, then I guess I won’t fuck you in the ass like you wanted me to,” I shrugged my shoulders. “You’re naked anyways, you might as well put it on.”
Her face turned red while she stood there, fuming. After a few moments, she put the outfit on. She walked up to me and stated her demand once again.
“Please, master, let me cum!” She begged.
I pushed her down to her knees. “You’ll have to do what I tell you first.” I quickly unzipped my jeans and dropped them down my legs. I released my hard cock from my boxers, and it sprung out in front of Terri’s face.
She’d gotten used to this already. If she wanted to be pleased, then she would have to please me first.
As I’d done many times before, I pushed my throbbing member into Terri’s waiting mouth. I closed my eyes and groaned as her warm lips took my cock in. In one stroke, Terri pushed my cock as far into her mouth as she could. Her nose was almost touching my pubic hairs above my cock. After the few weeks that she’d been doing this, she learned that the quickest way to get me to cum was to suck in her cheeks and wrap her tight throat around the tip of the cock.
And she’d gotten really good at it. I rested my hands on the back of her head and let her pleasure me. I loved hearing her gag every time she buried my cock as deep into her throat as she could. She also used her tongue, flicking it back and forth along the bottom of my cock. I started thrusting with my hips in an attempt to get my cock even deeper into her. Terri’s eyes started to tear up as I got rougher with her. Her gags became louder and more frequent, and her face turned red. Spit flew out of her mouth every time I thrust into her throat. As I felt the familiar tingling in my balls, I pulled out of her mouth and gripped my cock in my hand, rapidly jacking myself off.
I launched several ropes of cum onto Terri’s face. Each spurt caused Terri to flinch and move her head back, but she stayed right where she was. After her face was dripping with my cum, she opened one eye. She took my cock with one hand and guided it to her mouth so she could milk out the rest of the cum in my cock. She wrapped her lips around my tip and lightly squeezed my cock. I never even had to tell her to do that, she just learned to do it herself. It seemed my little sissy slut was getting used to her role. I pulled my softening member out of her mouth. I could see Terri’s excitement, even though she tried to conceal it. Her disappointment was even more visible when I pulled my pants back up.
“Master, I thought you were going to let me cum,” she complained, remaining on her knees.
“Oh don’t worry, Terri, I plan on doing just that. But I’m going to need a few minutes before that, so I think I’m going to teach you something new today,” I responded.
“W-what are you teaching me, Master?” She looked curious and slightly afraid.
“Don’t worry, it’s nothing bad,” I assured her. “At least, I don’t think it’s a very big deal. I just want you to learn how to clean up around here.” I emphasized those last four words. As Tim, she never cleaned up after herself and even hired a maid at one point. So, with the sexy French maid outfit I bought her, I figured it was the perfect time to teach her some basic housework.
“I… I never cleaned anything before…” Terri admitted. Well, I already knew that.
“Then I think it’s time for you to learn some basic homemaking skills, Terri.” I patted her on the head, then told her to stand up. “I’ll give you your reward if you do a good job.”
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I spent the next hour or so watching Terri figure out how to sweep the floors, make our beds, and even clean furniture. To be honest, a lot of the things were pointless. It was mostly to see her try and reach high shelves to dust books or random decorations.
Besides, it wasn’t too boring for me. I’d bought a remote-controlled vibrating buttplug that I made Terri wear. For the most part, I had it on the lowest vibration setting, but whenever she slacked off, I turned it higher. It wasn’t long before I saw precum dripping from Terri’s chastity cage.
The last thing I made Terri do was wash the dishes. She stood in the kitchen, wearing her now slightly dusty maid outfit and large, yellow rubber gloves learning how to wash dishes. She was tiptoeing to reach into the sink, which gave me a great view of her ass, which was exposed under the short skirt of the maid outfit. She seemed to be learning quickly and working hard, but I still decided to raise the speed of the vibration in her buttplug anyways. I felt my cock stirring as I watched Terri try to work with the distraction. Within a minute of having the vibrator on the highest setting, I saw another line of clear precum dripping from Terri’s cage. It seemed she was getting the hang of washing dishes, and I couldn’t hold back any longer. I decided to give Terri her reward a little early.
I turned the vibrator off, which was a welcome surprise for Terri, who seemed to regain a little bit of her strength. I quietly took my jeans and boxers off. I admired Terri’s ass for a little bit, then walked up behind her. I quickly pulled the buttplug out and rested my hard cock between her ass cheeks. She stopped washing the dishes and seemed to tense up.
“I didn’t tell you to stop, sissy,” I whispered into her ear from behind. “I just decided that you’ve been doing a good job and I’ll give you your reward while you’re still working.”
I put the vibrator in front of Terri and stuck it in her mouth, which made her gag a little.
I grabbed Terri’s ass cheeks and started massaging them and feeling them relax. Once she seemed to be comfortable again, I placed the tip of my cock and her asshole and thrust into her.
“Ohh!” She moaned through the plug in her mouth. She stopped working, but quickly resumed her scrubbing.
I wrapped my hands around Terri’s flat stomach and pulled her hips into me, causing her to tiptoe more to bring her ass up to the height of my cock. She was almost off the ground, just balancing on the kitchen counter.
I slowly pulled my cock out, savoring the feeling of the muscles in Terri’s ass clenching around my hard cock. I thrust back into her ass, aiming downwards. Even if she looked like a girl, she still had a prostate. It seemed I was really making her hot. She was breathing hard through her nose and her jaw was clenched tightly around the buttplug in her mouth. But through all that, she was still washing the dishes. There were only 2 or 3 plates left in the sink, but she’d been working on the same plate since I started fucking her. I chuckled at that.
“Terri, it looks like you’re about to break that plate,” I taunted her.
She shakily put the plate on the rack and started on the next one as I slowly pulled my cock out of her and rammed it in hard again and again.
Surprisingly, she managed to finish washing everything. She removed her gloves and washed her hands as I fucked her harder and harder. After she dried her hands on a paper towel, she gripped the kitchen counter hard.
“You’ve done a good job, Terri,” I whispered and pulled the buttplug out of her mouth, placing it on the counter.
“T-thank you, Master,” she panted.
I picked up the pace. I fucked her faster while continuing to aim at her prostate. To my surprise, Terri started to bounce back against me. Every time I fucked her before this, Terri didn’t move at all. Now, she took it upon herself to fuck me and try to make herself cum. The cage around her little clitty jangled as I rammed my cock in and out of her. I reached my hand around to grab her neck, choking her lightly while pulling her whole body close to me.
Our thrusts synced up, with Terri moaning every time I rammed deep inside her. I didn’t know how long it was, but the only sound in the room for a while was the sound of flesh slapping flesh. The air was filled with the smell of lust and desire.
“Don’t you love being my sissy?” I asked her.
“Yes, Master!” She screamed as she bounced on my cock.
“Tell me, don’t just answer my question!” I wanted her to say it herself.
“I love being your sissy! I wanna be your sissy slave forever!” She screamed it loudly in between pants and moans.
After saying that, Terri immediately tensed up, regretting what she said. But she was too horny to care. She continued to thrust into me, seemingly forgetting what she had just said a moment earlier.
“Oh, fuck, Master,” Terri moaned, “I’m gonna cum!”
As she said that, I felt the muscles in her ass convulse. Fuck, I was going to cum, too.
Terri was fucking me even faster than before. She angled herself so that my cock perfectly hit her prostate every time. Eventually, she slammed her ass into my cock and held it there and she screamed in pleasure.
“Oh fuck!” She squealed. Just like the first time I let her cum in the cage, she shot a little spurt of cum, followed by a few more, then a small but steady flow, dripping down her little clitty and onto the floor.
Her asshole clenched around my cock enough that it brought me to my climax as well. Even though I came just over an hour ago, I released multiple thick ropes of cum into Terri’s battered asshole.
“Mmm, that was fucking amazing. Don’t you like being a good sissy?” I asked quietly.
“Y-yes, Master,” she whimpered.
We stayed liked that for a little while. My cock slowly shrunk out of her asshole and I pulled away.
We were both breathing heavily, though Terri was much more tired than I was. It seemed she had a moment of clarity after she came down from her high. She grimaced in horror at what she had just said and done. However, the expression on her face slowly disappeared as she turned around. She was unable to look at me, though. I put my finger under her chin and tilted it upwards so that I was looking into her eyes.
“You’ve been a very good sissy, Terri,” I assured her.
“T-thank you, Master,” she responded.
“I’ll keep in mind what you said, Terri. About you being my sissy slave forever,” I smirked. Her face turned bright red and she darted her eyes away. She opened her mouth to say something, but no words came out.
I had finally accomplished my goal. I’ve turned my roommate into a mindless sissy slut.
