Roommate Caught Me

Some years ago when I finally got out of college, I thought I had finally freed myself from the general awkwardness that I felt while I was there. Other than not being the most handsome or manly guy you would come across, I didn't really hit it off well with the people I was with in college. I had stayed in a student dorm where I bunked with four other guys who had mostly kept to themselves in the sense that they wouldn't really push me to do things but they were also very rowdy whenever they were in the room, I still remember thinking to myself that I only needed to wait a few more years and I wouldn't have to deal with this kind of stuff anymore. Well, maybe from the title or description of this story, you'll be able to tell that I haven't really gotten away from having a roommate even after college.

After graduating, I got lucky with an advertising firm in the city when they accepted me for the position I applied for (which a lot of my colleagues tried to apply for as well) and everything was well except for the fact that I lived several miles outside of the city which meant I had to either commute hundreds of miles just one way to get to work or I would need to find some lodging nearby. I wasn't as lucky with my job application as I was with my search for a place to stay at since I literally spent the free time that was given to me from the job I just applied for looking for a place to stay at.

I kept looking around the city, surfing through social media for offers, and even asking friends who lived nearby if they could recommend any places. It was the last day before I actually needed to work when i found a relatively nice looking apartment building that was about 10-15 mins away from where I would work by walking. I wouldn't really say it was in the city since it was located near a suburb area already but it was close enough to some bus stations and I could even walk it if I really wanted to. It also happened to be one of my fastest and easiest inquiries to the place where the landlord was very nice and hospitable, really taking the time to show me around and answer my questions. The only problem I had was that despite everything I said about the place and landlord before, I still couldn't afford a room to myself. The landlord told me to wait while he checked on some things in his office and when he came back to me he told me that he did have a room available that would be within my budget but the only thing about it was that I would have a roommate.

Now this would have been a deal breaker for me a few days back but now that I was on a deadline to find a place to stay in that was close enough to work, I realized that I had to make a compromise now or deal with more than a hundred miles of commute everyday. I took a deep breath and told him that I'll take the offer even if it meant that I would have a roommate. Besides, I already had four roommates in college and I'm sure having just one would be a whole lot easier, right?

It didn't dawn on me that I didn't even get to meet this guy before I took up the offer that I would be his roommate, even more surprising to me was that he didn't even hesitate to allow another person to share their room with them.

The room itself was pretty large for an apartment. It must've been at least double if not triple the size of the dorm room I had in college, plus it had two small bedrooms that could technically just fit a bed and a small wardrobe if you could fit it right. The common area of the apartment had just enough space for a sofa and a tv, a small round dining table with two chairs, and a small kitchen area finished the rest of the apartment tour off. The apartment also had it's own bathroom but we were going to have share it.

When I first got there, the land lord tried to introduce us but when the door to the apartment opened he just looked me from top to bottom then back up and just gave me a nod before heading back to his room closing the door behind him. This might've been rude for some people but I was all for it since I didn't have to interact anymore than I actually wanted to and I wouldn't be bothered while I moved. I made the most out of the tiny space that my bedroom had. The bed I bought was new sofa bed that I could fold back into a sofa whenever I wasn't using it and at the foot of that bed would be my work desk where I would use my laptop for work or other purposes. I had also brought over a small closet from my time in college that I managed to squeeze in between the wall and the sofa bed. After about half a day, I was finally done moving and fixing up my things. It was already nighttime by the time I finished, I was tired and I also had my first day of work the following day so I did what every other guy would do towards the end of the day and wanting to rest already: jerking off.

Just to give a little more background, the direction of my work table was facing in front of the door to my room since I could only squeeze it in what little space I had in this room so that means that whenever I would use my laptop or something i would have my back against the door. Now if you've been caught many times before especially by your parents or your friends, you would know that the position I was in wasn't ideal but it was my only choice.

I figured that my roommate (whose name I haven't even gotten throughout this time) would already be asleep or busy doing his own thing in his room so I just shrugged it off and opened up my laptop. In my younger years, I would've gone to my go-to websites like Pornhub and all those different sites back then but in college I found that Reddit and Twitter/X was actually a more tailored search for me so ever since I found porn there, I haven't changed providers so to speak.

I opened up reddit to be greeted by the numerous pages and groups that I have slowly accumulated and become a part of. It started out like how every straight guy starts out with random girls filling my feed but I've had a guilty pleasure that I've weirdly enjoyed ever since I got into college and that was Trans Porn which eventually led to Sissy Porn. From thirst traps of girls filling my page, now I find my feed filled with femboys, girlcocks, and sissy captions. None of the people I'm close with know this side of me but I also can't deny how much I enjoy jacking off to these videos.

While I was scrolling through my feed, I passed by a sissy caption post that basically told me how great it was to be feminine, how I needed to submit to cock which was one of my favorite kinds of videos to watch on Reddit. It was actually a loop video that had a sissified pop song playing in the background so I put on my headphones and slowly started stroking my average sized dick.

On about the third or fourth loop, I was already repeating some of the words that I was reading from the captions like,

"Repeat after me: I am a sissy slut and I crave for cocks."

"Being feminine is what I've always been meant to be. Embrace it."

"My mind is consumed by the thought of cocks and cum. I am a sissy cumslut."

I hadn't even noticed how into it I was getting since I was already playing with one of my nipples without even noticing it and I just kept my eyes glued to the screen while the words repeated themselves in my mind. What I also failed to notice was that on the reflection of my laptop screen, there was a white light shining from the corner and when I looked closer at the reflection I realized it was the door to my room but it was open.

Fuck. Did I forget to lock the door before I started? Did my roommate just barge in on me jacking myself off and playing with my nipples while moaning sissy mantras? I suddenly froze in place and I subtly adjusted my laptop a little so I could have a better look at what was happening by my door. When the reflection on my screen drew in more of what was happening behind me, my jaw dropped from what I saw. My roommate was not only standing in my doorway but was furiously stroking his cock inside his very loose boxer briefs. I couldn't really see his actual penis but I could see the faint outline of the head as he stroked his cock to me.

I didn't really know if he was masturbating to me or to whatever I was watching but from the angle that he was looking at me from, he could probably see the flashing images of the girls in the video but he would need eagle eyes to even be able to read the captions being said there. So that must mean that he was either really held back that he would masturbate to small gifs of girls or he was in fact stroking his dick because I was stroking mine as well.

I hadn't even noticed that I was completely entranced by him jacking his cock off and add that with all the thoughts swirling inside my head already then top it off with a hypnotic sissy mantra repeated directly into my ear, I only caught myself with my mouth ajar when my drool made it's way to my chest which brought me back to reality only for a split second until the voice and the captions in the video said,

"That's it, cum for cock sissy. Pump, pump, pump and cum all over yourself, cum as you crave cock and it becomes the only thing in your mind."

That coupled with the reflection of my roommates cock stroking up and down inside his boxer briefs sent me over the edge. I rarely had that kind of orgasm that would have me shaking in my seat but that's exactly what happened. I was shaking uncontrollably as my cummies not only came out but squirted all over me while I bit my lip and moaned with each spurt. All that time I didn't take my eyes off my roommates cock as he also seemed to cum, a very thick wet spot forming at the tip of the head inside his briefs. None of us moved the first few moments after we just came but he slowly exited my room and shut the door without making a noise so as not make it obvious that he was there. I stared at the spot where I watched him stroke his cock before looking at the time and realized I only had a few hours left to sleep before I had to head for work. After I cleaned myself up, I went to bed and slowly drifted to sleep.

When I woke up the next morning, I thought to myself that everything that happened yesterday felt like a dream but when I looked at the door to my room I remembered every detail of what happened last night and I felt a slight tingle spread through my body. As I made my way out of the room, my roommate's door was open and he was nowhere to be found so he must have an early schedule and already left. I fixed myself up and went on with my day which went by a breeze despite it being my first day at my new job. It's not that it was all I could think about but there were these random moments throughout the day that made me think about my roommate stroking his hard cock inside his briefs and cumming at almost the same moment as I did.

After getting of work and making my way back to my apartment, all I could think about was getting on my laptop again and hoping that my roommate would come for another visit tonight. I got home and found my roommate already in casual clothes like he spent most of the afternoon here while I was at work. There was definitely an awkward air between us which made us just nod to each other and wanting to get myself out of the awkward feeling, I just made my way back to my room. We drifted in and out of our zones where I would be either in my room while he's outside and vice versa.

After the awkward night we had between each other, I resigned myself to the idea that whatever happened last night was a fluke of a moment and it probably won't ever happen again but boy was I wrong. We kind of felt each other out when it was already late at night, like I was sure he wasn't asleep and I'm pretty sure he was also wondering if I was asleep already. So I went to my door and opened it slightly ajar as a sign that he was welcome to come in if he wanted to. I made my way to my laptop and I assumed my position once again like last night and I started playing some sissy porn captions.

I had only started stroking for a good while when I saw the light shone at the corner of my laptop which meant the door to my room opened and I was greeted by the sight of my roommate already half naked below the waist. This caught me of guard and my mouth opened in awe to see his cock in all it's glory without the briefs blocking the view. He must've been a good 7-8 inches from my angle and he was just right when it came to his girth. He stood by the doorway and after a good while of making sure I was transfixed on what I was watching, he started stroking his cock once again. Instead of watching the captions in front of me, I just listened to the music or voices that came along with the video as I watched him slowly stroke his cock.

"Cock. Cock. Cock. That's all you can think about now sissy slut."

"Want it. Need it. Crave it. Desire it. You want to be a cocksucker."

"A sissy slut like you can only think about COCKS."

These words not only came from the video but were not seemingly echoing inside my mind as I continued to stare at my roommate's cock, stroking up and down and at times even pooling a small drop of pre-cum on the head that would drip down with each stroke. I hadn't even noticed it but my mouth was already open as my thoughts slowly drifted to imagining myself kneeling down in front of him, sticking my tongue out as he stroked his cock in front of my face. I also started playing with one of my nipples as I watched him from the reflection of my screen, slightly squirming from the different pleasures I was feeling right now: masturbating to another man's reflection with my mouth agape and my nipples sensitive.

I only closed my eyes for a moment and when I opened them again, it seemed he was a lot closer to the screen than last time as the light from the hallway now shone behind him instead of directly on him when he was still by the doorway. He must've stepped closer without me noticing. Was he trying to get a better look of what I was watching or was he trying to get a better look at me? I didn't want him to be spooked so I didn't react to him getting closer to me and instead I started stroking faster and I squirmed a lot more obviously. His stroking behind me started getting faster and his cock was getting slick as well which helped me hear him behind me better. My senses were slowly getting overwhelmed as I stared at his penis that was now seemingly right behind my shoulder and the sound of the slick strokes that got faster and closer to me.

I was already almost over the edge from everything that was going on when I suddenly heard him hold back a groan under his breath and a warm sensation hitting me behind my shoulder, on my shoulder and some even hit me on my jawline. He not only came again like last night, but he came on me. Granted it was behind me and not really on my face or anything but the feeling of even just helping another man cum sent me over the edge and I started orgasming myself. My moans turned from deep manly gutturals to slightly girly moans with each spurt that came out of me. I hadn't even noticed him moving out of my room as I was too distracted and consumed by my own orgasm, only catching on when my door clicked shut and I was once again alone. There was a tinge of post nut clarity but it was also sidelined each time I would replay what just happened. His cum was starting to feel dry on my shoulder and jawline so I scooped some of it up and despite the pnc hitting me a bit, I shrugged it off and stuck my finger in my mouth as I tasted my hard earned sweet reward. I cleaned myself and the room up like a robot before crashing into my bed.

The next few days passed by like clockwork where I would go to work, get back home and put up my laptop on just waiting for my roommate to come in as scheduled. We would jack off together with him always finishing right behind me, sometimes his cum would fly past me unto my desk and sometimes his cum would just drool out as it slowly crept down my back; each time I would put up sissy porn to watch only to finish watching him stroke and cum all over behind me. But one night, he decided to take it to the next level for the both of us.

There we were in our usual positions in my room but now instead of just staring at my screen, I acknowledged him coming into the room by turning my head to the side before returning my focus on the screen. The sissy porn about roommates hummed as I watched his reflection:

"Your roommate walked in on you watching sissy porn, and now he's going to make you into the sissy slut you really are."

"It's not gay if you're just helping your roommate cum, that's what buds do right?"

"You want that cock. You want to feel it on your hands, in your mouth, and especially your sissy boipussy."

It felt like a tailor-made video for the exact situation I was in. My focus made me cross-eyed on my roommate's cock as he stroked harder and seemingly closer and closer to me. Before I knew it, I felt a hand on my shoulder which made me jolt in surprise but his grip on my shoulder was firm like he was telling me to relax and let him do the work from here on out. The slick strokes of his cock got closer and closer to me when I finally felt it on my shoulder. His hard throbbing cock, the weight of it all, on my shoulder as he held his cock while sliding it on my skin. I could see from the reflection how he held his cock at the base and how he fucked his hand like a fleshlight with the half not held sliding on my shoulder and hitting my neck. I couldn't help but moan under my breath with what I was watching and he was liking it too since he was also holding back moans while stroking on me.

Not much time passed while we did this but after a while he must've gotten bored and a little but more daring because he suddenly stopped jacking off on my shoulder and started pointing it at my face. It was like he was waiting for me turn my head and inside my mind I really wanted to but I was also scared by the sudden build-up of everything happening all at once. He didn't let my hesitation stop him though, he started stroking again but from the reflection of the screen I could see that he was also directly aiming his dick at my cheek. His wet strokes were now right beside my ear as it echoed in my head, the wetness making my mouth water as well and the sissy inside me screaming at me to just turn my head and get that delectable cock finally into my mouth but I still hesitated.

He suddenly shifted his position behind me where I could felt him get closer to me until his leg was now touching my back and his cock grazed the side of my chin in the process. He adjusted a bit until he was in a comfortable position almost like he placed his crotch on my shoulder for support, and here I thought things wouldn't get wilder. I could still see from the reflection of the screen that he was stroking his dick to stay hard while he did all the adjustments he did but when he was finally finished, he put his right hand on my face like he was carefully holding my chin and jaw with his palm not touching my face. Then I felt it. I felt his cock slide from right below my ear into his hand until the head popped out the other side, the side of the head of his cock grazing the side of my lips. My mouth automatically opened, either from shock or sissy thirst, with a moan escaping it the first time he stroked his penis with my face.

I couldn't believe what was happening, from the time I first caught him masturbating in my doorway to the first time he came on me and now he was using my face as a sort of fleshlight and here I was moaning as he stroked his cock with my sissy face. He must've taken my non-resistance as a sign that I was enjoying it or at the very least consenting to it so he picked up his pace and started really sliding his already wet cock on my cheek.

It didn't take long for him to really get into it because he changed the position of his hand so now the palm of his hand was not staring back at me and with this change, his dick was now sliding directly over my lips. I mean if I just opened up my mouth while he did this it'd be like in the porn videos where the girl would suck and lick on the side of the dick before enveloping her mouth on that oh so tasty head that's leaking precum. It didn't take long for me either to make that thought into reality but I just made it seem like I was just moaning on his dick, except I would also stick my tongue out whenever the head would pass in then and out of view.

All this time I was just watching my reflection on the screen: my eyes looked drowsy and submissive, aside from the hand blocking most of my face I could clearly see my openly drooling mouth with his cock coming in and out of view while my tongue would flick and lick at his penis whenever it can. I was still stroking my own penis and I was also playing with my nipples. I looked like a lost but still slightly sensible sissy who's just yearning for her reward.

I didn't really know how long we would last just doing this with one side of me just wishing that he took further control and just shoved his dick inside my mouth. There didn't seem to be any sign that he was willing to go that far but then the audio from the sissy porn I was watching suddenly chimed in. It was a pmv of different sissies getting fucked in all kinds of position and the audio played:

"You like that sissy? You like being put in your place and being used like the sissy slut you are?"

"The best thing about sissies is that you get to use their both their holes with no risk!"

"He's going to cum all over you sissy and you are going to swallow every last bit of it to show daddy how grateful you are for your cummy reward."

I don't know if he was watching what I was watching as well but after a few hard and fast strokes across my face, he suddenly tensed up and held his cock saying, "Fuck, I'm about to cum."

This was it, it was now or never. I timed his strokes and when he pulled away from my face that's when I turned my head slightly so when he stroked back to my face his head entered my parted my mouth and for the first time I looked at my roommate. His eyes were closed tight with his head leant back while he continuously and furiously jacked off on my face and when I turned my mouth towards his dick his scrunched eyes loosened up and he moaned (or groaned whichever) hard. His head entered and exited my mouth for a few more strokes before he finally went over the edge.

I looked at the head of his penis going in and out of my mouth before he exploded all over me. After the last stroke, his dick throbbed and I could imagine the amount of cum that was coursing it's way through his penis for it to throb like that. The head swelled up into a deep purple before a familiar and long awaited white fluid came out. To say that it came out is an understatement though because I was blasted with thick spurts of semen.

The first spurt hit my upper lip which were followed by two more spurts that coated the area where my mustache would be and started drooling oh so slowly down my cheeks. He pulled his dick away before stroking it back with his hand and this time he aimed for my mouth before shooting more of his load into me. I closed my mouth around the head of his cock as I felt it throb with each spurt that unloaded inside me. Each spurt forced a moan out of me which probably sent him even further since now I was also moaning on his cock while he served me his delicious cum. He tried stroking his cock again but my mouth held him firmly in place until I felt him starting to soften up inside my mouth and then I let go. I hadn't even noticed it but I also came during that rewarding session and it was a pretty strong orgasm since some of my cum made it all the way to my neck not unless he also came that much that it made it there.

We were both panting from the experience and with no words exchanged, he tapped my on my shoulder a few times like to say that I did a good job and he fixed himself up before heading out of my room and closing the door behind him. I just sat there in front of my screen with sissy porn still playing but all I could look at was my reflection on the screen. My mouth was covered in saliva and semen while my cheek was smeared with what can only be my saliva and the precum that came from his dick while stroking on my face. Recalling what just happened in my mind and I found myself having a dry orgasm, my body trembling and shaking as I felt like I was cumming but there wasn't anything coming out.

After that I closed my laptop but still, my body tingled from what just happened and in all honesty I also felt my ass pussy ache. I don't know if it was from sitting down for so long, or if it's just jealous from getting fucked and filled like my mouth pussy was a while ago. I should probably ask my roommate for some help with this as well.

End.

Author's Note: Thanks so much for reading through one of my stories again. It's been a while since I got to writing again with a really busy schedule during the middle of the year but now I have some more stories already lined up including a probable (depending on the reception of this story) sequel for this story. I wasn't really sure if this was a story more apt for Crossdressing/Trans (sissy themes) or Gay Male category but I ultimately decided to go with Gay Male since it was more focused on the two guys. Please do feel free to comment on my stories as I love these little interactions I have with my readers!