There is point when it is enough. When you have to stand on your own feet. When it is time for you to leave your family home and get a place on your own. It was a few years ago when I made this decision. But rents were already through the roof back then, so I needed a roommate to be able to afford anything. I came up with the great idea to ask a long time friend of mine, who was about twenty one years back then, to move in with me. Luckily it didn’t took much to persuade him to join in, because he had exactly the same problem like I had.
After some searching – it actually was nothing but a big pain in our backsides – we found an affordable, surprisingly big place for the two of us: A room for each one, a kitchen, a big living room and a bathroom. We immediately turned it into our man cave. Or better said, into our party hub. We did what you do when you move out from home when you are in your early twenties: Lots of drinking, mixed with loud music and fucking everywhere. Luckily our neighbors were forgiving. Or never home. Or just deaf. We never had any problems with them back then. And we still have no problem with them until this day.
Our party central was up and running for about a year. Then my roommate and me had a talk, came to the conclusion that it was enough and turned the place into a comfy, relaxing man cave. Into a real home for the two of us. We still had guests over from time to time, but if we wanted some real action, we went elsewhere. Only some casual hookups landed in our place.
It was around that time that my roommate began to change. He grew his hair out and more and more beauty products, mostly for women, showed up in the bathroom. Yes he began to wear makeup. He even painted his fingernails. And he always was freshly shaved. I wasn’t thinking much of it back then. Probably some goth emo phase, a little bit late with twenty two, but stranger things have been happening.
Otherwise we really got along with each other. We split all household chores. The place was clean, the fridge always filled and we never ever ran out of toilet paper. Besides that, we came closer in every other regard. We talked about next to everything. We just good best friends.
Time was passing by. Nothing out of the ordinary was happening. Until one day, I was on laundry duty, I discovered some female panties in the dirty laundry. I wasn’t shocked or anything, just curious about them. That’s why I asked my roommate about them. He told me that it was some trophy from a girl he fucked a few weeks ago. But his head turned red while he was talking with me. Like I had caught him doing something he was ashamed off. I didn’t bother to ask him any further. I just shrugged my shoulders. While smiling at him. Signaling him that it was perfectly fine thing to do.
Things got even stranger, or more interesting with time. One night, I couldn’t fall asleep, I was searching the fridge for some midnight snack, when I heard some female moaning coming out of my rooommate’s room. I didn’t hear someone coming home with him earlier, and no came to visit him later on, so I assumed that he was watching some porn. Jerking off his wiener to some girl pleasing herself. Probably not having the sound off, because he was thinking that I was asleep. I never ever mentioned it to him.
Beside that nightly incident I realized that my roommate kept on changing even more. His posture got more female, his voice changed and his body changed too. He lost weight, his ass got rounder. It was clear to me, that something was going on with him. But I didn’t found the guts to talk about it with him. But it shouldn’t take long until everything would change.
It was one ordinary Wednesday. Due the fact that there was nothing left to do, I was sent home from work earlier as usual. When I entered my place, I caught my roommate in a very intimate situation. He was sitting on the kitchen room floor. Riding a huge dildo. Wearing makeup. His long and beautiful hair framing his face. His body smooth and hairless. He was wearing nothing but a bra, some panties and a chastity cage to lock away his dick. In front of him, on the floor, a camera recording or streaming him fucking himself.
He didn’t realized that I was in the room with him. He was too far gone. He was fucking himself into oblivion. I just kept on standing in the kitchen door. Not really knowing what to do I just kept watching him toying himself with a huge ass dildo. Yes, it made me rock hard. My mouth was dripping saliva. I imagined him riding my rock hard dick. I had to touch my dick. I had to jerk off. The urge just was too big. And grew bigger with every second. My damn roommate, a damn hot sissy girl. I couldn’t believe my luck.
He finished before me. His whole body was trembling under a heavy orgasm. An orgasm from anal only, his dick still locked up in a his cage. Squirting out some sperm. Sperm that was immediately caught by one of my roommate’s hands and went straight into his mouth. Good girls clean up after themselves. Then he said goodbye to his audience. It was in that moment when I shot out my own load, directly on the floor in front of me.
My roommate just smiled at me and my rock hard dick. He seemed to be relieved that I had caught him. And he seemed to like that I liked what I just had witnessed. After the incidence we sat down in the living room and talked. Talked about what I had witnessed. Talked about him being a sissy. Talked about his transformation. Talked about his main income working as a cam girl. And we talked about the fact, that he wants to be referred to as a girl, as woman from now on. I listened, nodded and promised her my full support. And we also came to the conclusion, that is was better for now, not to tell our parents anything about what was going on.
After our talk things changed a lot. The only male clothes in our place, except from a few emergency sets, were mine. The bathroom was suddenly filled with female beauty products. And the living room turned into a streaming studio with professional lighting and lots of fancy camera gear. I helped my roommate as much as I could. I operated the camera, took stills of her, just listened to her when she was in need for an ear and I watched her shows. Jerked of while she was playing with herself. Constantly fantasizing of me joining in on her stream. Just replacing her dildo. Fucking the shit out of my damn hot roommate. Making her caged limp clitty squirting a fountain of cum. But it should take some time until my first time with my her.
Source: reddit.com/r/Erotica/comments/y5cqqk/my_roommate_the_sissy_m22f22_sissy_roommate_anal
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