Sissy

I like it when someone takes over and tells me what to do. I also like men, not women. Shortly after I turned 18 I met a guy who was somewhat older than I. I lost my virginity to him, and hoped for a long beautiful relationship but it didn't last.

In college my roommate was straight, or so I thought, but liked telling me what to do. His girlfriend would leave her frilly undies and stockings. I started trying them on when no one was around. Since I am a smaller guy they fit. They made me feel like the woman I knew I was inside. One day they came back unexpectedly and caught me wearing her stuff. She almost blew a gasket! He just stood there staring with a smile on his lips. She ranted for a while then calmed down and started laughing. She told me to take off the stuff, I grabbed my robe and started to head to the bathroom. She got a vicious look on her face and blocked the door.

"Where do you think you are going sissy?"

That was the first time I had heard the term, I got what she meant though.

"I'm going to take this stuff off." I said a little embarrassed.

She moved toward me and said, "Take it off right here."

I couldn't believe what she said and hesitated a bit. She walked to me and poked me in the chest, but didn't say anything. I knew my roommate was watching and I didn't want to have problems with him, so I started stripping.

The way he looked at me I felt like a piece of meat, and to my chagrin I started getting hard. They both started laughing.

His girlfriend said, "Look, the sissy likes being watched."

I couldn't say so, but she was right, liked her telling me what to do and him watching.

Two days later he came in with a bag. He pulled out stockings, garter belt, bra and panties. He threw them at me and told me to put them on. I wasn't sure where this was going, but I did as he said. I pulled the panties on and found they were a thong. They covered my cock, but went up my butt crack.

When I had all that on he reached into the bag again and pulled out a very short plaid school girls skirt and a crop top. He just gestured for me to put them on. As I did I got hard, and not just a little hard, I was getting rock hard.

"I see you like being a sissy," he said as he pointed to my hard cock.

I hung my head and whispered, "yes I do."

Then he dropped his pants and underwear, I saw he was almost as hard as I was. He didn't have to tell me what to do, I dropped to my knees and put his cock in my mouth. I started playing with it like it was a popsicle. I licked it up and down, I put the whole thing in my mouth then I would just back out and keep the head in my mouth. I stuck the tip of my tongue in the piss hole and rolled my tongue around the head.

After a bit he pulled me up and pushed me onto the bed. He kept lube by the bed and grabbed it, he put lube on his fingers pushed my legs up and put lube into my ass and around the hole. Then he lubed up his cock and crawled between my legs. I felt the head of his cock pushing against my hole, I reached down and pulled my thong aside and guided his cock into me.

He was gentle at first, he let me get used to his size. Then when he buried his cock up to the balls he pulled out a bit. He waited a beat then started sliding in and out, slowly at first then faster.

He had put both arms on either side of me, I grabbed his biceps so I could take the pounding he was giving me. I was in heaven! All of the sudden he stopped and got off me and stood up. He pulled me into a sitting position, his cock was right at mouth level. I had never sucked a cock after it had been in my ass, but he grabbed me head and shoved his cock into my mouth.

At first I started to gag. I had a cock in my mouth that just a second ago had been buried to the balls in my ass. He started face fucking me so I didn't have a choice but to suck. After a few thrusts I started getting into it, I was a sissy and I enjoyed it, I also enjoyed someone else taking charge.

It didn't take long before he started saying "oh shit, oh shit."

He pulled out and stood me up and bent me over the desk. He grabbed some more lube and lubed his cock and shoved it in. This time he wasn't gentle about it, he just put the head at my hole and pushed. I wanted to jump out the window it hurt so much. He started pumping hard. My ass was already loose from the first fucking he gave me so it didn't take long for me to feel that deep pleasure I get before an orgasm. It seemed we timed our orgasms, he gave a few hard thrusts and I could feel him explode in me. At the same time I started blowing my load.

He filled my ass with so much cum it felt like an enema, I thought I was going let loose right then. Cum started dripping out of my ass and down my leg. He pulled me back and pushed me to my knees, I didn't need to be told twice, I wanted to make him feel not good, but great.

Throughout college I would dress up for him and he would use me as his fuck doll sissy when he couldn't find a woman to hook up with.