My brother's friend is a sissy fag

My older brother’s roommate was always dressing like a girl for fun. They invited me to move in with them when I got done with school. The room was cheap so I did. I never thought twice about him dressing up now and then, I didn't think he was gay, just a little weird. But things changed after I moved in.

Any time I was alone with him, he would walk into the room dressed up. He got pretty good at it over the years. Sometimes you couldn't tell if he wasn't really a girl. He was tall, 6 foot 1 or 2, about 175 lbs, in good shape, so the girl’s clothes fit him well. He always pulled his hair back and put on just a little make up, and lipstick. He must have used some falsies because he always had the bouncy full figure curves. He would dress like a school girl or a secretary, sometimes even just in hot sexy lingerie and a nightie. He would parade around for me then sit close and play with my leg while we watched TV. He knew it made me mad so he always did it. I was bigger than him but I didn't want to have to fight over something stupid like that.

One night, he dressed like a maid, long black nylons and a short black frilly skirt. The top was like a corset with lots of straps and lace on it. When he wouldn't stop fooling around with me, I grabbed his arms and tried to pin them back behind him. He seemed to let me. I held him there for what seemed like a really long time. He wasn't struggling to get free. Finally I let go and he asked why I didn't keep going, tie him up or something. I thought that might be a good idea, to keep him under control for a while. I said he better behave. He quickly leaned over and tried to kiss me right on the mouth while he grabbed my crotch. He whispered something about putting up or shutting up.

After dragging him into his room by his wrists, I found a couple pair of pantyhose on the floor and tied his arms together behind his back. I sat him onto his bed and tied his ankles spread out to each of the bed posts.

That should hold him for a while, I thought. But he started bitching at me about how poorly I'd tied him and telling me what a wimp I was. I warned him to shut up or I'd do more. But he kept talking shit. I found a pair of his pink panties in his drawer so I rolled them up and popped them into his mouth. He opened wide for them. He tried to keep talking so I pushed another pair in and used a scarf to hold them in tight.

After a half hour or so I felt bad so I went back into his room to untie him. He was lying back on the bed, legs still spread and tied tight. He was moaning a bit into the panty gag and wiggling a little, too.

He had a huge hard on poking out of the black silk panty!

He was trying to roll and wiggle and get off. I stood at the side of the bed, staring him, and told him he was a real shit. I untied the scarf and pulled out the gags. He asked if I liked what I did to him, and liked what he looked like all dressed up and bound tight. He said the feeling of my hands all over him while I was tying him up was a real turn on. He asked for me to move closer as he tried to push his face into my crotch. I pushed him back, feeling the silky smooth corset and the sexy lace on his outfit. I stepped back and told him to fuck off. He said that was just what he had in mind. He said I could feel him up like a drunk prom date, if I wanted to. He told me to close the door and turn off the light. I did.

I sat on the bed and took him up on his offer. I replaced the wet panties into his mouth and tied the scarf back on. I groped the corset, squeezing the rubber tits inside. I rubbed my hands all over the silky nylons and pulled on the many sexy straps holding everything together. I could do whatever I wanted. He was tied and gagged and helpless. I playrd with his sexy clothes wrapped around his warm, smooth body. I was getting horny. 

I helped him get free of the nylons. Once free he removed the gag from his mouth. He took one of the nylons and wrapped it around my wrist. Then the other. He told me he was going to tie me up the same way I had tied him. I didn't respond. I was frozen and confused. I had a hard on. What the fuck? He tied me up and told me to open my mouth. I did. He took off his black panties and gently pushed the soft silky undies into my mouth, holding them in and rolling them around in my mouth with his fingers.

He laid me back on the bed and started kissing my neck and my face. He removed the panties so he could kiss me. Spreading my lips wide with his tongue and pushing it into my mouth. I struggled, but not too much. Soon he was stroking my cock, surprised it was already hard. Then he gagged me with the panties again, tying them in with the scarf i'd used on him. He quickly slipped down between my legs and started sucking my cock. It felt great.

He moved all the way around so he was on top of me, straddling my chest and sucking my cock. When I looked up all I could see was his spread wide ass with his balls dangling down under it. The corset and nylons felt silky and smooth on my skin. He had one hand wrapped around my hard on and the other under my balls, squeezing them, and then sliding a finger up between my ass cheeks. I guessed he wanted to poke one in, and sooner or later he would get one into my ass hole. He sucked, and licked, squeezed and probed, and sucked... wow.

When I started to breathe faster, he stopped and moved his ass back closer to my face. Then closer. Then he spread out right over my face. He reached back, pulled off the scarf and let he panties pop out of my mouth. He opened his cheeks. He told me to open my mouth and stick my tongue inside. I was pinned down by him and tied tight, wrists and ankles. He had a firm grip on my cock. I obeyed, closing my eyes. He slowly dropped down on my face and my tongue touched his ass hole... I jerked and tried to squirm away. I couldn't. He pressed his ass around my face; I struggled as I was smothered. He let me breathe, then squatted again ordering me again to lick him. I felt the tip on my tongue tickle, then enter his ass hole. He instructed me to probe and wiggle it and push it in as far as I could. I obeyed. He continued to suck me as I tongued his ass.

Finally he got up and let me breathe. He turned back so his cock was right in my face. He ordered me to open and take it into my mouth. He held it there and pushed it in as I tried to resist. He straddled my face and pumped up and down forcing his long fat cock in and out of my mouth. I took his cock in my mouth and tried to slide it into my throat, as much as I could. He made this last for what seemed like hours. He would get ready to cum, then wait, and then start again. When he did cum I thought I was going to choke to death. My mouth was so full of his cum. I wouldn't swallow it, but couldn't spit it all out. He helped me roll over and untied me so I could go clean up and drink a beer. When I was done he told me he owed me a favor, and I could fuck him because he came first in my mouth. I was still hard and ready to get off. He was standing in the doorway still dressed in the sexy maids outfit. Nylons and corset, he looked pretty cute.

He put on a new pair of black silky panties. They had a hole in the back. Made for ass entry, he said. Tie me up again and fuck me like a bitch, he said. I roped him up with nylons and pantyhose, kneeling in front of the bedroom mirror. There was just enough light to see him there looking pretty and vulnerable. I gagged him with the panties again and knelt behind him. I grabbed a handful of hair and pulled his head back. I reached around and molested his silk clad body. He moaned with pleasure as I fondled and squeezed him all over. My hard on wasn't going to get any bigger, so I slipped in between his cheeks and easily entered his tight little ass. He was well lubed for the act, but he groaned and cried as I began to fuck him. Just before I unloaded in him I pushed him down on the floor and mounted him hard. I came deep in his little ass pussy.

He squealed like a girl as I finished deep inside him. I whispered in his ear that "I hope you liked that, you little bitch."