My Sissy Roommate
Introduction:
All characters who partake in sex are over the age of 18. I hope you enjoy!
I swear he’s always like this. So worried about everything. I don’t know how the kid has survived this long. Probably because I’m always here to calm him down.
It’s kind of funny, not many people can see Andrew and me as being friends. Him being a meek, petite, nerd who’s often confused as a girl and me a muscle-bound, jock who gets all the girls. We’re complete opposites from each other.
And yet, Andrew and I have always been best friends. We grew up next door to each other, I’m always the one getting him into trouble, and he’s the one who tries to think a way out of it. Of course, he used to get picked on a lot in high school, but not when I’m around.
He and I are like peanut butter and jelly. Oil and vinegar. Wine and cheese. Milk and cookies. What I’m saying is, we just work well together.
I couldn’t imagine going to college without him.
We arrive at a party at a classmate’s sorority, she begged me to come after class. The place is packed with girls everywhere. Definitely a lot more girls than guys.
Sarah’s eyes light up as she sees me. Her blonde hair neatly coming down to her shoulders. “You came!”
“I told you I would,” I laugh. “This is my roommate and best friend, Andrew. Andrew, this is Sarah, the girl in my math class.”
“It’s nice to meet you,” she says. “Do you guys want something to drink?”
“Yeah, sure,” I shrug.
We follow her through the house, into the kitchen, where a giant jug cooler is. She grabs two cups and hand them to us. “Normally we charge $5 per cup for guests, but you two can drink on me.”
“Aww, thanks. Such nice hospitality.” I give her my heart-stopping smile which turns her cheeks pink. I can admit she has really beautiful eyes. So green and verdant.
We fill our cups with jungle juice and follow Sarah out to the back porch.
“So, how long have you two been friends?” she asks.
“Since kindergarten,” I laugh.
“Wow, that’s so cool,” she says.
“Yeah, we grew up next door to each other,” he adds.
“It’s so rare to have remain best friends in college, more power to you,” she says.
“What about you? You still with your best friend?” I ask.
“Well, not really. We sort of broke up in high school,” she says.
“Ouch, what happened?” I ask.
“She fucked my now ex-boyfriend behind my back,” she says.
“Ouch, what a bitch,” I say.
“Truly backstabbing,” she says.
“Definitely not a true friend,” I add.
“Yeah, not like the two of you, I’m so jealous,” she says. “But, I do have some pretty cool friends in the sorority.”
“Nice, we’ve made some friends as well. So what made you join a sorority?” I ask.
“My roommate convinced me, speaking of her, here she is!” A girl with dark brown hair and matching eyes walks up. “Becca, this is the boy from my math class I was talking about! Arthur, meet my roommate, Becca.”
I hold out my hand and she shakes it as she stares into my eyes. “It’s nice to meet you, Becca.”
“You too! Sarah has been talking nonstop about you,” she says.
“Has she?” I ask, raising an eyebrow. “And what mean things has she said about me?”
“Oh trust me, it’s all good. And you definitely add up to her stories,” she says. “With all the good things she’s said about you, I was beginning to think you weren’t real.”
“Well, I hope not to disappoint,” I say, giving her my lady killer smile. “By the way, you should meet my roommate.”
“You mean there are two of you?” she asks.
“No, Andrew is far smarter than I am,” I laugh as I put my arm around him. He tenses up as her eyes fall upon him. Her expression changes from giddy anticipation to a look a girl would give to a puppy. Not exactly what I was hoping for.
“Aww, he’s adorable,” she says. “You know, you’d be so perfect for my social experiment.”
“Oh, Bec, don’t!” Sarah says.
“Aww, come on Sarah. You know he’d look so good.”
I raise an eyebrow as Becca grabs Andrew’s hand and pulls him behind her. “Come, you need to meet my partner, Kenzie.”
Sarah grabs my hand. “We should probably follow them.”
“What’s her social experiment?” I ask.
“Ehh, you’ll see,” she says.
I follow her into the house and I see Becca talking to another girl with red hair. They both look at Andrew with excitement before dragging him upstairs. Sarah and I follow after them.
We go into one of their rooms where Becca and the red-headed girl who must be Kenzie are holding girl clothing against Andrew’s frame. The look on his face says it all. Shock, embarrassment, humiliation and if I wasn’t mistaken, a little bit of excitement.
“Come on, you should definitely try these on for us,” Becca says.
“I was afraid this would happen,” Sarah says as she drags me into the room and shuts the door. “Come on guys, don’t do this.”
“Aww, come on Sarah. Don’t be a buzz kill. You know he’d look cute all femmed out.”
“Wait, you want to dress him up as a girl?” I ask.
Andrew looks equally mortified and giddy.
“Don’t you think he’ll look so cute with this skirt on?” Kenzie asks holding up the skirt against his waist. Her eyes go wide as she brushes against his crotch. “Oh my god, do you have a boner?”
“No!” he stammers.
“Yes you do!” she says. “You’re enjoying this as much as we are!”
“I… I…” Andrew studders.
“Don’t be ashamed,” Becca says. “I think it’s so hot. You have to do it now. Just try on a few outfits. Please.”
Andrew’s eyes meet mine. He looks frozen. I’m not sure if he wants me to get him out of this situation or give him permission.
“Come on girls, just leave him alone. Look, Andrew. You don’t have to do this,” Sarah says.
“Oh come on, Sarah. Don’t act like you’re not into this. You were so into it when we were discussing it earlier,” Becca says.
“Yeah, it’s fun to talk about it, but to actually force someone to do it is another thing entirely,” she says.
“We’re not forcing him, we’re just persuading him,” Kenzie says.
“What do you think? You’re his best friend?” Becca says.
“It’s not up to me, it’s up to him,” I say.
Kenzie leans in a whispers something in his ears and his eyes light up.
“So, will you do it?” she asks.
“Okay, okay, okay!” he says.
“Wow, what did you say to him?” I ask.
She smiles. “Just offered him a blow job.”
“Kenzie!” Sarah stammers.
“Relax, it’s just a blow job,” she says.
“Not really,” I laugh. Andrew glares at me.
“What do you mean?” she asks.
“Andrew’s never been with a girl before. Not even for oral,” I laugh.
“Aww, he’s a virgin?” Becca asks.
Andrew looks as if he was just punched in the stomach.
“Sorry bud, it slipped,” I say, taking a sip.
“Now, let’s get those clothes off of you,” Kenzie says.
“You… You promise you guys won’t tell anyone?” Andrew asks.
“This won’t leave this room. We all promise we will tell no one,” Becca says, crossing her heart. “Now, let’s get these clothes off you.”
Both Becca and Kenzie attack Andrew and start stripping his clothes off. Once they get him naked, which by the way, he desperately tries to cover himself up with his hands, they start scouring through clothes.
Andrew is as red as a tomato. The weird thing is that I can’t stop staring. His ass is better than most women I’ve been with. So plush.
Andrew’s hazel eyes meet mine before he quickly looks away.
“Here, put these on,” Becca says as she hands him a pair of cute pink panties.
Andrew’s eyes go wide.
He looks at Becca and then back at the panties. Reluctantly, he takes them from her and slowly puts them on. They barely cover his bubble butt.
Fuck me. From the waist down, I would never be able to tell that he was a boy. At least from behind. His legs are as hairless as any girl’s I’ve come across. Am I seriously getting turned on by this?
Kenzie hands him a skirt. Again, he hesitates but eventually complies and puts it on.
Then, Becca, has him put on a pink sports bra and a white blouse.
Afterward, Kenzie brings him to the bed and puts a white pair of thigh high stockings on him.
“Okay, all that’s left is makeup and we’ve got to do something about your hair,” Becca says.
Becca grabs her makeup bag while Kenzie gets a pair of scissors, one of those hair bands. Andrew looks up at her with fear in his eyes. “Relax, I’m just going to trim it up a bit. It won’t look that much different.”
He closes eyes. “Whatever…”
She grabs a spray bottle and doses his hair and then goes to work trimming it. By the time she’s done, it looks vastly different. Adorable to say the least. His black bangs drift off to the one side and it’s slick and cute.
“Don’t open your eyes just yet,” Becca says as she starts layering on the makeup. It doesn’t take her long. “Okay, you’re good.”
Both Kenzie and Becca take a step back to admire their handy work.
I got to say, if I didn’t know any better I would’ve totally believed Andrew to be a girl. A cute one at that. I actually want to fuck him. Badly.
“Wow,’ Sarah says. I almost forgot she was in the room. “You two have outdone yourself. She looks amazing!”
“And you tried to talk us out of it,” Becca says.
“I was wrong. You’ve done a great job,” Sarah says.
“He’s so cute,” Kenzie says. “Now let’s see how well he does down at the party. I bet everyone will be convinced he’s a girl.”
“Wait a sec, you never mentioned anything about going out like this!” Andrew says.
“Relax. No one will be able to tell you’re a boy and no one will know who you are,” Becca says.
“Besides, every girl in this sorority will make sure you’re safe,” Sarah says. “As president of the fraternity. I will make sure no one hurts you or makes fun of you.”
“I didn’t know you were president,” I say.
She smiles at me.
“I don’t know…” he says, as his gaze falls to his feet.
“I say, why not? You’ve already gone this far. Besides, you look sexy as hell,” I add.
He looks up at me wide-eyed. “You think so?”
“Yeah, definitely.” I nod my head.
“Okay, okay. I’ll do it,” he says.
“Yes!” the three girls say in unison.
The girls grab Andrew and drag him downstairs before he even has a chance to breathe. I follow them downstairs. I’m still amazed at how they transformed him. Although, they did have a good base to build off. I can’t get his ass out of my head. Such a perfect bubble butt.
Becca and Kenzie flaunt the poor kid around the house, introducing him to just about everyone. He looks so flustered. His face is as red as a stop sign.
“So, what do you think?” Sarah asks.
“I just can’t believe it’s really him. He looks so different,” I say.
“Kenzie and Becca could make just about anyone look like a Victoria Secrets model. Although, they’ve really outdone themselves with your roommate,” she says.
“I can’t believe how natural he is. Sure, he’s a bit flustered, but I think deep down he really enjoys it. Like, the clothing just brought out the inner girl that was there all along,” I say.
“Yeah, that and the fact that he’s definitely gay,” she says.
I look at her with a raised eyebrow. “How do you figure?”
“The way he looks at you and acts around you, it should be obvious. He has serious deep feelings for you,” Sarah says.
“I don’t know. We’ve been friends since Kindergarten. Don’t you think I would’ve known?” I ask.
“Hmmm, maybe. But look at him. Look how that guy is flirting with him. He’s so flustered,” she says.
I glance over to see real douchey looking guy hitting on Andrew. He looks like he’s the type of guy to have two different girlfriends. A total tool.
And yet, Andrew is eating it all up. He looks like a natural girl. He can’t possibly be into this guy, can he?
Holy shit! The guy just swooped in and started kissing him! I can’t let this continue.
“I’ll catch you later, Sarah.” I head over as they break apart. I grabbed Andrew’s arm. “You ready to go?” I ask.
“Aww, you really want to go right now?” he asks.
“Yeah, let’s get out of here,” I say.
“Huh… How about I just meet up with you later,” he says.
“Are you serious? You’re going to risk everything for that guy?” I ask.
His eyes go wide. “You saw me?”
“Of course. Now let’s go before he realizes you’re not who you say you are.” I grab her hand and she reluctantly follows me.
The entire way back to the dorms we walk in silence.
Finally, in the elevator, he speaks up.
“You’re not mad at me, are you?”
“Why would I be mad?” I ask.
“I don’t know, you just seemed like you were,” he says.
“No, I’m not mad at all.”
“Okay… Cool. You’re not going to tell anyone back home about this, are you?” he asks.
“Of course not. You’re my best friend,” I say.
“I think I’m gay,” he says.
“Yeah, I kind of figured that,” I say.
“Really?” he asks.
“You did just kiss a guy,” I say.
“Do you really think he would’ve hurt me if he found out?”
I nod. She looks down away. I mean he… It’s so confusing.
The elevator stops at our floor and we make our way back to our room.
I unlock the door and as soon as he shuts the door, something takes over me. Something so primal. I pin her up against the door. Her eyes go wide as I press my lips against hers.
At first, she just stands there. Then she starts to kiss me back. I brush the hair from her face as our lips part.
As her eyes meet mine, I can see she’s wanted this for a long time.
“Don’t stop,” she breathes. Once again, I’m kissing her as my hand slides down from her face. I slide my fingers across her flat chest and slowly make my way down south. I reach to find my way down to her skirt. Slowly, my fingers work their way up under the fabric, touching the silky white thigh highs before I meet her bare skin.
I don’t stop there. I slide up until I find the panties covering her ass.
She shimmers at my touch. I can’t hold myself any longer. I hike her legs up around my waist as she wraps her arms around my shoulders. I carry her to my bed.
I climb onto the bed with her in my arms. We kiss as my fingers dig underneath the fabric of her shirt, slowly sliding it up. Our lips part as I tear off her shirt.
She looks up at me with those hazel eyes. I place my hand against the soft skin of her face and lean down touching my lips against hers. She slides her hands against the skin of my back, pulling me closer. My tongue pushes past her lips as my other hand runs across her chest, sliding under her sports bra and groping her nipple. I slide off of her and roll her onto her stomach.
I tear my clothes off before straddling her thighs. I lift up her skirt to reveal that panty-clad ass. So perfect. I grab each cheek. Her ass is so pillowy. Squeezing it, I kneed it and spread her cheeks apart. I grab ahold of the hem and slowly pull her panties down to reveal such a plush ass.
Scooting down, I spread open her cheeks and slide my tongue up and down, making her shutter. I meet her butthole with the tip of my tongue and dive in. She squirms and wiggles her butt. I give it a playful slap causing her to gasp out.
I give her little starfish a good tongue bath. Fuck she taste so good. And her ass feels so good in my hands. I love squeezing it.
I can’t take it anymore. I want her so bad, I have to fuck her. She’s mine after tonight.
I spit on her as and on my cock, getting both nice and wet.
I scoot up and smack my ass between her cheeks. She looks back at me, so nervous. I lean down and kiss those lips of hers.
“Arthur? I… I’m a little…”
“Don’t worry, I’ll take it nice and slow at first. But Andrew?”
“Yes?”
“After tonight, you’re mine,’ I start to press my cock between her cheeks. She grits her teeth and grips the bed. Fuck her ass is so tight.
I slowly push and wiggle my cock until it finally pops inside her. “Urgh…” She groans out. “It hurts!”
“Shhh…” I bring my hand over and brush the hair away from her face as tears roll down her cheeks.
I kiss them away. “Don’t worry, I’m going to take it nice and slow.
Little by little, I inch my cock farther into her tight little bum. Every time she groans and squirms, I let up and allow her ass to adjust. She brings her hands back and spreads apart those asscheeks.
My cock sinks a little further inside her. She bites into the pillow. I pull a little bit of my dick out and watch as it dugs on her ass. Slowly I push my cock deeper than before. She gasps for air. Fuck, it’s just so tight. It’s like sticking my cock into an ant hole.
Ever so slowly, I start working my cock in and out. Fuck, it’s so hot watching my dick dug on that butt. Practically brings her hips with me. She whimpers with each thrust.
The more I push into her, the more of my dick she can take. Finally, I plunge all 8 inches inside her as my hips touch her ass cheeks. I can feel my balls rest on top of hers.
I lay down on top over her and wrap my arms around her. I move my hips back and forth slowly at first.
Hearing her start to moan is music to my ears. I start thrusting a little harder. She cries out and grits her teeth.
Fuck it feels so good to be inside her. I’m lost in the moment. It’s hard to even think let alone remember that it’s Andrew underneath me, taking my cock. Does this make me gay, to be fucking another man? No! Andrew isn’t man, not anymore. Not dressed like that. Not with an ass like that. Andrew’s my girl from now on.
I’m not going to let her go.
“You’re my girl from now on,” I whisper in her ear as I slam into her. Hearing her moan only makes me want to fuck her harder. And I do, thrusting harder and harder into her. She cries out, moans and groans with each thrust. I wrap my arms around her neck and she grabs onto them as I let loose on her ass, pounding my dick deep inside her.
Her moans are such a sweet melody. Her ass grips my dick so tightly.
She clamps down hard around my cock. “Urgh, I’m cumming!” she shouts out.
I don’t let up and I pound the cum out of her. But I can’t last much longer.
I hilt my dick all the way inside her as the tension in my balls becomes too much.
“Urgh, fuck!” I scream out as I erupt inside her tight little ass. She moans as I fill her but up with a thick load of cum.
Slowly, I continuing thrusting inside her as my dick squirts load after load inside her.
I collapse on top of her as my cock goes flaccid in her tight bum.
We’re both desperately trying to catch our breath.
I kiss the back of her neck before I pull out of her ass. A rope of thick cum keeps us connected before it breaks off and lands on her ass. A glob of my thick seed squirts out of her gaping butthole.
I give it a soft slap before rolling onto my back.
She takes a couple of minutes to recoup before looking up to me with a glazed over look.
“Did you really mean what you said?” she asks.
“What part?”
“That I’m yours?”
I reach over and pull her into my arms. “Andrew, seeing you all dolled made me realize how much I really like you. I mean, It’s confusing. I’m not gay or anything. But to me, just now, you weren’t a boy, you were the most beautiful girl I’ve ever seen.”
“So you didn’t really mean any of it?” he asks.
“I don’t know, this is all confusing. Aren’t you just as confused as I am?” I ask.
“Yeah. At least when it comes to dressing up as a girl. I always believed I was a man, but now… I’m not sure. I liked being dressed in girls’ clothing. I enjoyed getting hit on by guys. I kind of knew I was gay. I never told anyone because I remember how people treated the few kids who came out at our school. And if I”m being honest, I’ve always had a crush on you.”
“Wow… Really?”
“Yeah, I think you’re the hottest guy ever. And you’ve always been so nice to me. I felt like we had this connection,” he says.
“We do. I just didn’t think it was this kind of connection.”
“So now what?” he asks.
“Like I know…”
“Do you still want me?” he asks, his eyes look so sad as if he’s expecting me to say no.
“I mean, I’m not gay or anything, but if I’m being honest, I do. But I want you as a girl,” I admit.
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