Sissy Apartment

I’d finally found a decent place in New York, a 2 bedroom place on the Upper West Side. It had a pretty good sized living room, a kitchen and a bedroom I could actually walk around in. I had been living in a hole in the wall for months now and it was good to finally find a place where I would have some room. I’d found the room on craiglist and I’d be rooming with a young gay guy. His name was Joe, he was a slim white guy, my age (24) and we got along pretty well.
It had been a week since I moved in and I had realized that Joe had quite the active sex life and that the wall between our rooms was rather thin. I’d be trying to go to sleep but it felt like I was practically next door, hearing Joe get fucked. I could hear him moaning and begging for more. “Fuck me! Give my that big black cock, I love it.” The wall was so thin I could hear the slapping of skin as the man increased his tempo, pounding away at Joe. “Yeah, take my cock you fucking sissy, I know your faggot ass loves it.”
After weeks of this I was starting to react in ways I didn’t expect. It had been a long time since I’d fucked a girl myself and I started looking forward to hearing the nightly sex session of my roommate Joe, or rather Jane, as he liked to be called. He’d began to be more open about who he was, dressing like a frilly girl all the time in the apartment. I began to look at him differently, he really did have a feminine figure. I’d catch myself looking at his ass when he bent over. And I think he noticed too, because he began to dress even sluttier, with short skirts and thongs. He also got louder at night, “Fuck my slutty ass. It feels so good, fuck this faggot, you’re cock is so big!’ Every night I looked forward to listening to him, or rather her, get fucked. I was blowing the largest loads of my life, and I’d never been hornier. One night, when I was especially horny listening to Jane ride what I imagined was a thick, black cock, I slipped a finger in my ass. I nearly came right then, and soon my whole finger was deep in my ass, then two, then three. I came harder than I ever had that night.
The next day, I visited a sex shop I’d seen downtown one time. I bought several dildos and lots of lube. I even bought one with balls and everything, with a suction cup as a base. That night I started with the smallest one, moaning as I heard Jane get fucked and imagining that a real cock was inside me as well. I stuck the big one in my mouth, imagining I was sucking on a cock too. I came harder than I ever had in my life that night. If Jane noticed the changes in my, she didn’t let on. She kept fucking away each night and I kept furiously masterbating with my ass every night as well. I was watching sissy porn, only concentrating on the cocks I saw, never the girls. I’d even started wearing butt plugs during the day, and riding the biggest dildo every night until I came.
Finally one night, everything changed. I didn’t hear any sounds coming from Jane’s room, but I was so horny I had to get off. I was so engrossed in riding the dildo that I didn’t hear Jane come in. “I knew from the first time I saw you that you were like me, a sissy fag.” At her words I spurted all over. I was so embarrassed, someone finally knew about my secret. “We need to get you fixed up, I’m gonna make sure that sissy slut inside you gets out” She began helping me to take the next steps. Soon, I’d shaved all the hair on my body, and I was wearing the sissiest underwear under my clothes during the day. Of course kept wearing the butt plugs as well. Jane taught me how to put on makeup, and I would dress in the gurliest clothes we could find.
Then the night I’d been dreaming of came. Jane brought her master in one night, and told me it was time that I became a true sissy. I immediately dropped to my knees and began slobbering all over his big black cock. I licked up and down, sucking on his shaft, his balls and gagging on his huge dick. He pulled his cock away from me and I moaned with disappointment, why would he take his cock away? He laid on his back and I realized he was making me take the final step. After this, I could never go back. I may have played with my ass before, but once I took his cock inside me, I’d be a sissy forever. I’d never fuck another woman, I’d just be a receptacle for cocks. I crouched over his cock, the tip pressing lightly against my tight hole. Did I really want to be a sissy? Always dressing up for me, sucking their cocks, getting fucked up the ass like a sissy faggot, having cum sprayed on my face. Was this what I really wanted? I came back to reality, his head was already inside me and I let myself go. “Yes!!!” I screamed, “Cock feels so good! It so big, fuck my sissy ass.” As I bounced up and down on his cock, Jane came up to me and whispered “You’re a true sissy faggot now, there’s no going back. We’re going to have so much fun.”