1. Becoming Kitty


    Date: 9/22/2015, Categories: First Time, Gay Male, Shemales, Author: CumLovingKitty, Rating: 100, Source: xHamster

    I guess I should start with that I've loved to wear panties. In school, I would sneak into my mom's room and put on her panties. While I was straight, at least so I thought, my fascination with panties never stopped. In college, after my parents died in a car accident. I had my first gay experiences, including my first crossdressing experience for Halloween my high school. After my parents passed away and since I was an only c***d, I basically came out and began to openly experiment with my sexuality with both men and women. However, my true passion was dressing as a woman and having sex. I was somewhat of a natural at school and graduated Bachelor of Science by the time I was 21 and Master of Science when I was 23. My parents had left me, as an only c***d, a rather large trust fund. Although I loved studying, I hated my boring life. I would spend weekends having mindless sex, sometimes with guys and other times with girls. Standing at 5'6&#034 with a narrow, almost feminine frame, both guys and girls were attracted to me. While I was 23, I looked younger. In fact, this all started during one of those weekends when I invited a guy I had met back to my place. Of course, the clothes came off and it wasn't long before he was fucking my ass from behind. Since I had kept my body shaved, starting in college and continuing after, he started calling me a sissy fag as he fucked me. He told me I would be a better girl than a guy. I had one of the best orgasms of my life as pounded ...
    me and called me those names. As he fucked me, all I could think about was how much fun I had dressing a woman in college. Once he left, the thought of dressing as a girl in panties consumed me and I found myself wearing women's panties all the time. I also found crossdressing porn in the Internet. I was hooked and a month later, I had purchased makeup, wigs, heels, dresses, skirts, blouses, lingerie, fake nails and stockings. Of course, money was not an object. I started dressing regularly as a girl when I was at home and I had a couple more sexual encounters with guys. I was becoming obsessed with cock. In fact, I was paying more attention to the guys in porn scenes than the girls. I wanted to get fucked again as a girl. I posted an ad on Local hookup site saying I was a new CD and wanted to find a guy that would treat me like a lady and fuck me like a slut. I got numerous responses, but the guy that caught my attention was a middle-aged married man who said he hardly had sex anymore with his wife and being with a CD was a fantasy of his. We agreed he'd come over to my place the next day, which was a Saturday. Since he was to be over around 2 in the afternoon, I started getting ready around 9 in the morning. I started with an enema and then a bubble bath. While in the bath, I made sure to shave every inch of my body and put in my medium butt plug. Once out of the bath, I covered myself liberally with lotion and then I slid on a pair of panties, yoga pants and tank top. My ...
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