Free Shemale Stories - College Cutie

Free Shemale Stories - College Cutie

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College Cutie

It was my first year at college and I was 300 miles from home. It was great! Here I was 18 years old and on my own, no parents, no annoying siblings and no rules. Oh, and did I mention I had two women as roommates? Yeah, and they were cuties, but not my type. Now their boyfriends, on the other hand, were something to look at. Both of them had big, jock type boyfriends, one of them quite handsome and the other a little plain except for his rippling muscles. 

I guess at that age I would have to say I was some what messed up sexually. I found both men and women attractive, although I had never dated a man and women didn't seem to quite do it for me.

I was your average 18 year old basically. I liked going to movies, hanging out with my friends and dressing in women's lingerie. Ok so maybe that's not so average but for me it seemed quite normal. I had been dressing up in my mother's silky nighties and dresses since I was about 13 years old and found it fun. I guess I could say it turned me on. It still does turn me on, only difference now is that I do full make up with it.

My roommates at the time didn't suspect a thing. To them I was just one of the guys. They had no idea that I wore their clothing when they weren't home. And even tried out their make up, put on their shoes and pretending I was them. I'd talk to myself in mirrors and even pretend I was having sex with one of their boyfriends. I almost got caught on a few occasions, but managed to avoid being found out by the skin of my teeth. That is until one night when I fell asleep in one of my roommates bed with her nightie on.
Both the girls had gone away for the weekend, so I had the place all to myself. That Saturday night I went full out, I put on a nightie, did my hair and make up and even shaved my legs, arm pits and face. I pretended to talk on the phone and talk about my life as if I were my roommate. I ate snacks and watched the girl's favorite TV shows, then to end the night I crawled into her bed and pretended her boyfriend was with me, touching me and kissing me. I guess it was during all that that I fell asleep.
Next thing I knew someone was crawling into bed with me. I almost shit my panties to find it was my roommate's boyfriend. He was kissing me and rubbing my legs. I had no idea what to do, I just laid there acting like I was still sleeping. Then he put his hand down my panties and I immediately jumped back from him. In the same moment he jumped out of bed and flicked on the light.
"What the hell do you think you are doing? Why are you in Lisa's bed, with Lisa's nightie on and make up? What are you, some sort of freak!?" He yelled harshly at me almost making me cry.
I had no idea what to say, I sat there listening to him go on for some time about how messed up I was. He kept going on and on about how he was going to tell Lisa and our other roommate about what I was doing. They would have surely kicked me out if they were to find out what I was doing with their clothes. I couldn't hold back the tears any longer thinking that was it, I was going to be ruined and humiliated.
"Please, I beg you, don't tell anyone about this. I was just foolin' around. That's all, nothing major", I pleaded.
"Ok, I won't tell anyone about what you did. I'll keep your secret but you have to do something for me", he slowly said as a smirk came across his face.
"ANYTHING! I'll do anything you want!"
"", the words seemed to echo in my head.
I couldn't believe it. I stood there in complete shock for about two minutes before saying I'd do it. What else could I do? And it's not like I didn't want to do it. I found the idea of sucking him off appealing. My own penis became erect as I watched him remove his from his pants.
He ended up being one of the best lovers I had ever had. We continued seeing each other, behind closed doors of course, for three years. Even when he broke off with Lisa and went out with other women. He would bring over his girlfriend's clothes for me to wear and even call me by their names. Being a cross dresser has its ups and downs and I have to say that was definitely an up point.


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