About two years ago my roommate left town. He was leaving the place we share for about five years. He had a job offer he couldn’t decline. So I had to look for a new person to share my apartment with, because back then I wasn’t able to afford it on my own. And I didn’t wanted to loose my home. Because it was affordable and I just loved living in it.
Many people showed up and took a tour through the place. Most of them weren’t down my alley. Of those who were some just didn’t want to move in with me. It just took some time to find the right new roommate. And luckily one day, he showed up.
He was about twenty two years old and something between him and twenty nine year old me just made click. He genuinely liked my place, he could stand me and so he asked me if he could move in. I told him that I needed some time to think about it, but about two hours later I sent him a simple message: “You can move in, if you like.”
Not even a minute later he sent me a confirmation: “Thanks, when can I dump my stuff into my new room?”
Yes, my new roommate was one who did tacks with heads. He wasn’t the manliest looking man out there, but he was one that wasn’t into wasting time. And someone that stood by his word.
But my old roommate was still living with me, so I told him that he had to wait three more weeks. A “No problem, I just transferred you the deposit” came back. We set up a date to sign some paperwork, to hand him over the keys and then I spent some relaxing three weeks in my place: Cleaning, renovating and hanging out with my old roomy.
Then the moving in day came. It was a Friday. He showed up with some friends and a rented van. They carried his stuff into his room and dumped some of it into our living room, the bathroom and into the kitchen. Once everything had found its was up into the apartment the friends left. He thanked them, they left and from now on he lived with me, in my place. My place that should turn into our place with time.
It took some time until all of his stuff found a place in the common rooms. His own room was ready within a couple of hours. I helped him reassembling his furniture and hanging up some pictures and similar stuff. Once we were done, he thanked me and signaled me to leave him alone. I respected his privacy and went into my room.
On the next day we took care of his kitchen stuff, his bathroom stuff and the stuff he dumped into our living room. And to my, to our surprise his things matched mine. It enhanced the assemble. Once we were done redecorating we got rid of the trash and ordered some pizza. Then we ate, talked with each other and got to know each other a little bit.
We found some common ground while hanging out. We had a couple of laughs. Then he addressed the household chores. A first time for me, because previously I always was the one that had to bring up the topic. But not this time. His doing, it made me like him even more. Then we split the household chores in equal parts and established a rotating system. After the hard work was done, we called it a day.
To my surprise the splitting of the household chores worked out perfect. Na arguing, everyone did his part on time without having to be told to do so, the place staid clean and tidy. Our arrangement just worked as planed.
Again, it was a first time for me. During our day to day life, we two got along. We were living next to each other. Not being in each other’s way or going on each other’s nerves. It being that way told me that I probably had chosen the right roommate. Despite his young age.
As time went by we got to know each other better and better. We figured out that we really got along with each other. So one day I found the courage to ask him about the female beauty and care products that showed up in our bathroom. At first he dodged the question. He did that to give him more time to think about a suitable answer.
Once he had one, he shared his wisdom with me. He told me that the female shampoo was better for his long hair than the male one. He told me that he used female skin care products because the worked better with his sensitive skin. And he told me that he needed the nail polish for some role he was playing in some amateur movie some friend of him was making.
While listening to him I already made up my opinion about it. An opinion I shared with my roommate as soon as he was finished explaining: “Do whatever you want. I don’t judge you. And well, stop making up things.”
His face froze. By the looks of it I had caught him red handed. I had no clue with what I had caught him, but well, I figured that I would find that out sooner or later. But for now, I let it be. I told him that it is okay. I told him that he didn’t need to worry about me. And I told him that his secrets were safe with me, as long as he stuck to our cleaning schedule. A relieved smile appeared on his face: “Thank you, I will.”
Then the conversation went elsewhere. We spent the rest of the evening together. Doing guys hanging out stuff while having a blast. Until it was late and time to brush our teeth and go to bed.
A couple of weeks later something strange happened. Late at night, at a time when I usually was asleep I went into the kitchen to grab me some midnight snack and a glass of water. While I was standing in the kitchen I heard some very intense female moaning coming out of my roommate’s room – you get into his room by going through our walk through kitchen. It made me curious: Was he screwing a woman?
After listening in for some time, after getting my stuff I went back into my room. I had my snacks, I had my water, then I fell asleep. On the next evening I ran into my roommate in the kitchen. I just had to ask him: “Have you had someone female and willing in your room yesterday night?”
To my surprise he blushed. Awkwardness all of a sudden was filling the room. He struggled to get a single damn word out of his mouth. I made one step back: “Been watching porn on full volume? No problem with me either.”
He nodded. He began to relax, his face lost it’s red taint: “Yeah, I was watching porn. Sometimes I just have to turn up the volume while doing so.”
I told him that it was fine with me. I also told him that I wasn’t hearing anything when I was outside of the kitchen. I also told him that the walls were thick and the ceilings too, so the neighbors for sure weren’t able to hear anything. A somewhat relieved expression appeared on my roommates face. Then we went our ways again.
The next somewhat strange thing happened about a week later. I made a discovery in the washing machine in our bathroom. When dumping in my dirty underwear and my even dirtier socks I found a nice set of woman’s panties inside the machine. It took them out, I took a closer look at them and in exactly the moment I had them in my hands my roommate came around the corner.
When he saw what I had in my hands, he got an anxiety attack. He froze, he blushed and he nearly collapsed. He clearly didn’t wanted me to find those. I tried to calm him down, I tried to make him feel better: “A souvenir from the past? I got some of those too in a drawer in my room.”
My roommate took a few deep breaths in and out. It took him some time to get his shit together again. Then he finally opened his mouth. He spoke with a very insecure voice: “Yes, it is. From a woman I fucked a year ago. It must have slipped into my laundry.”
His reaction, the insecurity in his voice, something smelled fishy. But I decided to let it be. I decided to not dug into the topic any deeper. I just handed him the panties and then I watched him walking off towards his room. I never ever mentioned the incident again, neither did he.
Time moved on. Things were going the usual ways in our apartment. I meanwhile had found a full time job, my roommate was still hanging out at university. I worked regular office hours, so he knew when to expect me back home. He basically hat the place for himself during the day from the moment I became a full member of the work force. My roommate got used to the fact that he can do whatever he wants for the time I was at work.
One day, it must have been four months after I found the panties in the washing machine, I found out what my roommate was up to during the day. My boss told us to go home shortly after noon. He told us that we did well and that we deserved a reward. So I grabbed my stuff, jumped onto my bike and rode back home
Once I arrived at home I opened the door and went inside. At first I put down my stuff, then I went to the bathroom and then I went over into the living room. While still listening to some nice tunes on my blue tooth headphones.
But as soon as I entered the living room I froze. My roommate was in it. He was wearing some lingerie, he had his hair open and he had put a lot of make up on his face. To make things even worse he was bouncing up and down a huge dildo while there was some porn on the TV. It took me more than a few moments to process what I was seeing.
One of the first things I did was taking my headphones off. And there it was again, the female moaning. Nope, it didn’t came out of the TV. It was my roommate. Enjoying himself while riding his more than decent sized toy.
I must admit, watching the toy going in and out of his butt, watching his limp dick, his balls bouncing up and down with every thrust he gave himself, it had something. It made me rock hard. I just had to stay, I had to watch, it was dragging me in.
Luckily my roommate was already gone to far. He was elsewhere. He had already lost track of his surrounding. His moaning was filling the room. His eyes were running in circles while his face gave out random expressions. All that mattered for him in his state of mind was the plastic dick sliding in and out of his tight fuck hole. And damn it, him being that way, him fucking himself, it was nothing but hot to watch.
Without even thinking, out of pure instinct I began to touch myself. I began to jerk off my rock hard dick while still being covered by my pants and my boxers. I just had to do it. And fuck, it felt good.
After some time watching my roommate fucking himself, after some time polishing my own rock hard dick while leaning against the door frame there was only one thought, one fantasy left inside my horny brain: I want him to bounce up and down on my rock hard dick. I wanted to fuck him up his ass. I want to make him moan out like a woman.
Meanwhile sweat was running down my roommates body. He still was at it. He had some stamina. He kept the pace. He took the toy balls deep. He took it hard. I meanwhile had to suppress my moaning. I was working myself towards an orgasm too. One stroke followed the other.
While my roommate gave himself one thrust after the other. He was close to an orgasm too. His body was tightening. His hands were looking for something to hold on to. They found his own tights. He squeeze his own tights while he kept on riding his toy. And damn it, how I wished it would be mine while he would be riding me cowgirl.
And then, boom, my roommate came from fucking himself up the ass. His balls unloaded themselves through his limp dick. His moaning stopped and then he collapsed onto the floor.
I came a few seconds after him. I creamed my boxers while watching him creaming our living room floor. My body was shaking when my balls dumped their sticky load inside my underwear.
It took us both some time to be ourselves again. As soon as I was back in my body again I wanted nothing but to turn around and leave. While hoping that my roommate wouldn’t even realize that I had watched him, that I had jerked off to him. But he regained faster than I did. He saw me standing in the door frame. He saw the bulge between my legs. He just stared at me. And I just stared at him.
We kept on looking at each other for what felt like an eternity. Then your eyes met, then we both panicked. I excused myself, I told him that I was sorry to interrupt him then I ran off into my room. I heard him excusing himself for fucking himself in the middle of the living room and then he probably grabbed his stuff and ran off into his room.
We both had no clue, no idea what to do next. We got out of each others way for about two days. We successfully avoided each other, luckily the layout of our flat makes that a relatively easy thing to do. But we both also no knew that this was no solution for our problem. We needed to talk, and it was me who made the first step.
Source: reddit.com/r/eroticliterature/comments/111jrq0/my_roommate_the_sissy_m29f22_sissy_toys