Turning my Roommate into a Sissy Slut
Introduction:
This is a new type of story for me. I hope you all enjoy. Feel free to leave comments or suggestions!
The work is pretty tough, although I like it here better than my last school.
My name is Aaron Walker. I’m a junior in university now, but it’s my first year here. For my freshman and sophomore years, I attended a local community college near my town just to get in some of the simple course requirements for my major. I found that it was a lot cheaper than if I took those classes here.
But the easy stuff is over, and I’m a ‘real’ college student, now. But what doesn’t help is the fact that I was forced to live in a dorm room. It’s a rule here that first year students have to live on campus, so even though I’m a junior, I’m still technically a first-year. Which meant rooming with a freshman. Which I eventually found out meant that I would be spending most of my time with a snobby, rich kid, with only a 3-inch wall between our rooms. It’s not exactly the ideal situation.
Well, not yet, anyways.
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“Hey, Aaron!” Tim yelled before he was even through the door.
I sighed and grunted in response. This obnoxious asshole was the guy that I’d been living with since the start of the school year. It’s only been a month, but it sure felt like a lot longer. This guy’s habits were just terrible. He would spend days in the dorm, playing video games and eating my food. Then if he ever left the dorm, he would be gone the entire day and come back after midnight. I don’t even know where he goes after taking his classes. However, I could tell that he grew up with a silver spoon in his mouth. He never throws out the trash, washes the dishes, or does any sort of housework. For a the first month or so, I wondered who took care of his stuff, because I only clean my own stuff, and I’m sure as hell he didn’t clean his. I eventually found out that he paid for a cleaning service that came in every other day or so to clean his room and our shared living room, kitchen, and bathroom. The cleaning service only came during my school hours, which also explained why I occasionally saw some of my stuff missing.
I did try to confront him about it. I tried to tell him to stop getting the service to come, since they were taking my stuff, but he just scoffed at me. He thought I was joking. He then just asked, “So who’s going to clean up?” This kid was a real piece of work. Needless to say, I always made sure to keep my stuff in my room, as it was the only place the service didn’t clean.
Right now, I’m working on a report for my biology class, one of the mandatory classes for anyone attending this school. Well, I was working on it.
Tim dropped his designer sweatshirt on the laptop I had in front of me. The kid flopped himself down on the couch next to me.
I only call him a kid because it seems like he never even hit puberty. Either that, or he’s just very feminine. Tim is shorter than most people in the school, including the girls. He also has a pretty high pitched voice.
But one defining male feature that he has is that fact that he relentlessly hits on girls. He just tries and tries, but he never seems to get anywhere. And I only know this because he pretty much follows me around to any social event I go to. Now I’m not saying that this is primarily a male thing, it’s just that I haven’t been around enough women to see this kind of behavior.
I just ignored Tim and threw his sweatshirt back at him. I had to continue my work.
“What are you doing?” he asked, oblivious to the fact that I didn’t want him here.
“Homework. And I don’t want to be distracted right now.”
He looked closer at my screen. “Oh, that?” the kid scoffed, “I finished that like two weeks ago.”
I sighed. Probably the only thing going for this kid besides his rich family was his smarts. And as I said, the work I’m doing is for a mandatory class, so guess who else was also taking the class? Of course, the asshole sitting right next to me.
“Then can you do this for me?” I asked him, hoping that would discourage him.
Instead, he just looked at me and smirked. “Yeah, I can do it for you,” he started, “but what’ll I get out of it?”
I wanted to punch this guy so bad. Then, I looked down at him and thought of something. It was crazy, but I might get a laugh out of it. “I can get you laid.”
The smile disappeared. I had his attention now. He was trying not to show it, but I could tell that he was interested.
“So what, I get laid all the time, I don’t need your help with that,” Tim seemed like he was getting serious now. He got up from the couch and started walking away.
“Sure, kid, I bet you’re super successful with the ladies,” I called out after him. He flipped me off and went into his room, slamming the door behind.
I laughed and turned back to my work. If I knew anything, it was that rich kids want everything they don’t have. And I’m pretty sure that Tim has never had sex before, despite the act that he always puts on. Well, I’d just have to see if my plan would work.
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A couple of days passed by, and Tim didn’t seem to bother me as much. I guess the kid was really taking into thought what I’d offered him. I was sitting in the living room of the dorm when Tim came in, holding a little cardboard box.
“What’s this?” Tim asked. “It’s addressed to you.”
I was really impressed. He’s even started respecting me a little bit. Before, he probably would’ve opened the package before he even came inside, but now, he actually asked me first.
“Well, I’m going to a party tonight, and I ordered that for it,” I responded. I could tell that he was getting curious.
“So… what is it?”
“Open it and see.”
Tim ripped the box open and pulled out another, smaller, discrete black box. There were no words, images, or branding on it. I got up and walked over to him, then took the box. I purposely held it high enough that he couldn’t see inside, then flipped the top open, took out a small rod and put it in my pocket.
The kid was getting more curious, so I brought the box back down so he could see inside it.
It was a small, metallic chastity cage. Tim looked at it, surprised. “Isn’t this one of those cock cages? What kind of party are you going to?”
“Well, I’m obviously getting laid at the party.”
“So why are you going to wear this?” he was definitely confused, which was what I was going for. He took the box to look at the chastity cage.
“Didn’t you know that these help improve your stamina?” I was just hoping that my bullshitting would convince him. “Well, I’ll be taking that, I’m gonna need it.” I took the box back from him.
“Wait!” he reached out and grabbed my arm. “Can I use that tonight?”
“Well, I only have this one, and I was planning on using it.” I pretended to think about it.
“I-I’ll do that report for you, it’s not due yet, right?” Boom. There it is.
I waited almost a minute, just pretending to think about lending him a chastity cage. It pretty much took all my willpower not to laugh.
“Alright, fine. Do you know how to use it?” He shook his head no. So he shyly turned around as I instructed him on how to put it on.
“Ok, it’s on. Now what?”
“All you have left to do is close the latch on top of it.” I heard a click.
My plan worked!
“Can we go to the party now?”
“Relax, kid, the party’s in a few hours. Besides, you have to keep the cage on for a few hours for it to work. You can do my report while we wait.”
I could see that Tim was starting to get unsure. But to my surprise, he stuck with it. I guess the kid really wanted to get laid. I smirked as he sat down in front of my laptop, took a few minutes to adjust to the cage, then started working. While he did that, I planned out what I could do next.
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“Ok, I’m done, Aaron.”
I got up and read over the report. It wasn’t bad. This obnoxious kid could probably actually get things done if he just had the motivation. And that thought gave me a pretty good idea.
Tim was fidgeting with the cage on his cock. “Can I take this off now and go to the party?”
“What party?” I asked with a grin.
“W-what do you mean, ‘what party’? The whole reason I put this thing on was for that. And I can’t get it off!”
“You know, for such a smart kid, you’re pretty gullible,” I was relishing in the fact that I finally had this asshole in my control.
“Wait, what the hell, Aaron?” his voice was getting higher and higher as his face turned bright red. If I didn’t know any better, it would’ve sounded like this kid was a girl.
“You remember that little rod that I pulled out before? That was the key to the chastity cage that you’re wearing right now.”
“Then unlock it!”
“I could… but I really don’t want to. You see, I’ve had to deal with your shit for so long, you know that?” I started raising my voice as well. Then I took a deep breath and calmed down. “Sure, I’ll take it off. But I want you to do something for me first. Take your clothes off.”
“I’m not fucking doing anything until you take this fucking cage off me!”
“Well how am I going to take it off if I can’t see it?”
Tim looked at me for a second, exasperated. Then he sighed and did as I told. He stripped naked and walked up to me. I could see his cock was soft inside the cage.
I couldn’t really helped but get turned on. I wouldn’t consider myself gay, but I was getting turned on by the power trip. I was really in control of this little piece of shit. Besides, the kid has a pretty big ass and he even has some small tits. And either he always shaves or just naturally has less pubic hair. There was a small patch of light-colored hair over his small penis. The rest of his body, besides his eyebrows and head, was practically hairless. This kid really got the short end of the stick when it came to hormones. If it wasn’t for the little cock he had, I would think that he just looks like a young girl.
I just couldn’t help myself. I stood up and spun him around. I grabbed both of his wrists and held them behind his back with one hand.
“H-hey, Aaron, what the fuck are you doing?!”
“I’m teaching you a fucking lesson, bitch,” I growled. My cock was already getting a little hard, but having this dominance over someone really made me horny.
I practically ripped my belt off and dropped my pants and boxers. Tim tried to get away from my grip, but I held him tight.
“H-hold on, Aaron, what are you doing?” Tim was almost screaming, “Stop it, come on, man!”
I ignored him. This little piece of shit is my bitch now.
I spit onto my cock and his little puckered asshole. I poked my now rock-hard cock onto the tight hole.
“Please, Aaron, stop!” he was scared out of his mind. But I wouldn’t stop. I knew he deserved this. Tim struggled to get his wrists free, but I held onto him tight.
I rested the bottom of my cock along the crack of his ass. I slid my cock up and down his crack, getting myself harder while Tim got more and more scared. The kid was begging me to stop. It almost seemed like he was crying.
I wouldn’t have done this if it were someone else, but this kid needed to be taught a lesson.
“You better stop screaming, you don’t want the neighbors to know how much of a worthless little bitch you are, right?” I muttered into his ear. “Don’t worry, I won’t hurt you… much.”
I started to push into his ass. Holy fuck he was tight. At some point he decided to stop fighting it and just started taking deep breaths, trying to accommodate my large cock inside his asshole. When I managed to get the head of my cock into his little hole, he started moaning.
“Oh fuck, Aaron, it’s too big, I can’t…fuck, fuck, fuck…” he just trailed off, muttering.
“You think this is big? Just wait, bitch.”
I kept pushing further into his ass. I was able to get my cock about halfway in when I couldn’t push any deeper. So I started pulling out. I grabbed his ass cheeks as the skin around her hole pulled outwards with my cock. This was so fucking hot. When my cock was almost all the way out, I started pushing back in. This time it was a little easier, but his hole was still very tight. I was able to get a little deeper, and now my little bitch was starting to get used to it. I pulled out again, then thrust back in. This time, I pushed hard. It elicited a very high-pitched yelp, but that was really it. He was getting used to this pretty quickly. I relished the moment when I felt his body relax and almost go limp, as if he was accepting the situation.
After a few more hard thrusts, I was able to start fucking him. I started slowly, driving my rock-hard member as deep as I could, then slowly pulling it back out. As he got more used to it, I was able to start moving faster. I don’t know if it was the body’s natural reaction or if he was actually getting turned on by this, but it felt like his asshole started to lubricate itself. He was still tight as hell, though, and I was getting close to cumming. I reached over and grabbed my new slut’s small tits. I twisted and pulled on his nipples as I increased my speed. This felt so fucking good. I could feel my orgasm coming. Every time I slammed against him, I felt my member reach further and further inside the defiled hole.
Soon the room was filled with the sounds of slapping flesh, followed by high-pitched moans.
“Oh, oh fuck… fuck me…” my little slut was moaning like a bitch in heat.
Since he was still getting used to his first ever ass-fuck, the muscles in his tight asshole clenched around my cock and massaged it. This pushed me over the edge. I couldn’t hold back anymore.
I thrust hard into his asshole and kept my cock inside. I grabbed him by the chest and pulled him close to me. My cock twitched as I shot load after load of my cum into my little slut’s asshole. I wanted to stay like this forever.
When I got over my high, I pulled my cock out of his ass and wiped the remaining cum on his ass cheeks. I realized that he was playing with his own cock. Because of the cage, he couldn’t really do much besides shaking it as fast as he could, but I could tell that he was just getting himself more frustrated. He probably couldn’t cum just from the stimulation he was providing himself, but he looked like he was getting close.
I decided that I wasn’t done with him yet, so I grabbed both of his hands and held them behind his back.
“No! Fuck! Aaron, please, let me cum! Just take the fucking cage off or something! You got what you wanted!”
This was a real sight. I almost laughed aloud. My roommate, the most arrogant and selfish person I knew, had been degraded down to a defiled slut trying to get himself off.
Well, at this point, I don’t think I can even refer to him as ‘him’. My roommate is now my bitch, and while he isn’t exactly a woman, he’s definitely not a man anymore.
I laughed at that thought. My own little sissy slut.
“You’re right, bitch, I did get what I wanted. But now I want more.”
“W-what do you mean, man? Just let me go, I won’t tell anyone about this. I-I swear!” My sissy was still acting like he had all the power.
“Oh, I’m not worried about you telling anyone about this. You should be the one worried about me telling someone else, though.”
“I-I… just let me go!” He stammered.
I could see that his little cock was as big as it could get, straining against the inside of the cage. It was twitching like crazy.
“Relax, bitch. I’ll let you cum when I let you. So you better listen to everything I say or I may never take that thing off of you.”
That sure did it. He got quiet. The only thing I could hear was his deep breaths. “I’ll do anything if you take it off…” he whispered.
“Oh I know you will. Now keep your hands behind your back and stay in that position.” I removed my own hands.
I could tell how difficult it was for him, but he stayed in the same position, bent over the back of the couch, as his cock twitched wildly underneath him. I could now see the thin line of pre-cum dripping from the tip of his little cock. I quickly got my phone from my room and took a few pictures. I used one hand to pull one of his ass cheeks to the side, causing him to moan in pain. I reveales his new gaping hole to the camera and watched my cum slowly drip out of it. I definitely took a bunch of pictures of that. It was so hot to see his hole contract every time his cock twitched.
I told him to close his eyes and stand up.
“W-why… what are you going to do, Aaron?”
I slapped him hard on one of his ass cheeks. “Stop asking questions and do what I tell you to.”
He stood up, still facing away from me. I turned him around, to see that he had, in fact, closed his eyes.
He just sniffled as I got more pictures of him. I made sure to get his face in it. However, I didn’t want him to know I was taking pictures. I wanted to have fun teaching my new sissy, without him worrying about blackmail. It would be much more fun. But I would still keep the pictures just in case.
I walked back to my room and put my phone away, then returned to the living room, where Tim was still standing, eyes closed tight. “Alright, bitch, I think I’ve punished you enough for now.”
He sighed a sigh of relief and opened his eyes. “Finally, man, now get this thing off me, please!”
“This doesn’t mean that I’m taking that cage off of you, yet. I still have much more to teach you.”
His face twisted up. “No, no, please! I can’t take this anymore!” It was true, his cock was still straining against the inside of the cage.
“If you say anything else tonight, I’ll flush the key down the toilet.” That got her to shut up for good. “Now let’s go to bed.”
I pulled her along silently to her room and pushed her onto her bed. When she laid down, she moved her hands to her restrained cock once again. I grabbed her hands and held them above her head.
“Don’t move.” I laughed internally as he grimaced in frustration.
I went to my room and pulled the shoelaces out of some of my old shoes. I went back over to my slut and tied his hands to the two posts on either side of the headboard. My sissy slut just sobbed silently.
I left his legs untied. I wanted to give him some hope that he might be able to do something to free himself. Well, even if he was somehow able to get free, he wouldn’t get far without the key. I was surprised to see that his cock was still hard in the cage, but it looked like he was calming down.
I slapped him in the face. It was very satisfying, to say the least. I left the room, turning the lights off on the way out. Before I closed the door, I looked into the dark room.
“We’ll talk more tomorrow, sissy.”
