1. Crossdresser First Sissgasm at the Adult Bookstore


    Date: 5/1/2016, Categories: Anal, First Time, Gay Male, Author: iam2daveyboy, Rating: 100, Source: xHamster

    I was never really sure about my sexual orientation. So this weekend I dress up as a woman to visit an adult bookstore in order to lose my homosexual virginity and become a submissive gay slut. My own penis is locked in a chastity device as a gang of black men uses my body for their pleasure and make me understand what I really am … I was determined. This weekend it would happen. I would loose my gay virginity and complete manhood. The hard way. Tonight would change everything. Until now I've never had sex with a man and I didn't consider myself as homosexual either. But I was always fascinated to anal sex. The thought of &#034Why would someone let herself/himself get fucked in the ass, when there's no actual pleasure of possibility to orgasm in it?&#034 Also the thought of giving up your body for someone else's pleasure was something that always turned me on. And since I've never could get an erection whenever I tried to have sex with a woman, I decided that I should do other things to compensate. Maybe becoming a gay sissy would be the answer? All I knew was that it really made me horny thinking about it ... As I laid on the bed in the small hotel room I trembled a bit nervous. Was I ready for this? I stopped thinking and got up. Time to prepare myself. So I got into the shower and removed all my body hair. After giving myself an enema I worked a large black butt plug into my ass. It would be better to stretch out a little. Then I attached my fake DD breast forms onto my ...
    chest with a huge amount of extra strong adhesive. That took a while, but after the sticky fluid dried I stood up and my tits stayed in place. They wouldn't come off now without using some special chemical. Next I applied some body lotion on my body, so my skin got very soft. I put on black fishnet stockings, a short black top and matching black panties with the words «Fuck my ass» written on my ass. The sluttiest outfit that came to my mind. Then I put on my long black wig and applied some makeup which included heavy mascara, dark eye shadow and a bit of lip gloss. Almost done. As I looked into the mirror, I didn't saw one masculine thing. I was a slutty looking sissy. But that wasn't enough. There was one thing left to do to be completely feminized. Thinking about it gave me a very strong erection and almost like hypnotized I started stroking my member. But then I stopped and proceeded to do what had to be done. I went to the minibar and took some ice and put it on my penis and testicles. I had to get rid of this erection. As my genitalia shrunk I quickly put the CB3000 chastity cage on it and locked it up. This clear plastic device made it impossible to get erect and touch myself. I put it on because I knew exactly that as soon as I would have an orgasm, I wouldn't want to be fucked anymore. So before I could get second thoughts I went to the toilet and flushed the key down. Now it was done. No more erections or possibility of pleasure through my sissified peenie. My ass ...
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