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First Time

At this point in my life I have been dressing as a girl on and off for about 5 years. It wasn't just dressing I was into however, I have been fantasizing about a man using me as I tried to present myself. I was a virgin at 18 both with girls and with men, eventually the urge to change this was too strong so I went to craigslist. My heart was pounding as I typed out the post that many horny men would check out hoping to score some young boi pussy. "Virgin sissy" was the title and I knew i would get many responses cause who wouldn't want to take a sissies virginity haha A man answered my post with an interesting idea. I am very into bondage and rough sex so he wanted to play on the idea and make me his slut buy tying my hands behind my back and using my mouth before working my ass. It turned me on so much I had to respond. We set up a time for the next day at a hotel near by.
The drive there was nerve racking, I mean here I was a straight acting male going to a hotel and dress up as a young girl to get fucked. I had second thought not once, not twice but three times. First at the hotel entrance, than in the elevator and when I was staring at the mans room door. I was considering leaving when the door open.There in front of me was a 38 year old Caucasian man about 6 foot two, light facial hair, and a fit yet plump body. My heart was beating 5 times faster than normal. "I almost thought you weren't going to show up" said the man. I just smiled and walked in as he held the door for me. I walked into the bathroom to get ready. Opened up my backpack and got everything ready. I am completely shaven and smooth so I took a cute pink thong and slid that over my little clit and between my cheeks. Than slid on a pair of thigh highs with a garter belt to keep them up. Than i took a matching bra and slid that over my flat chest. Of course it took some time for make up but i than took a nice brown wig and pinned it to my head making sure it couldn't move. Looking at the mirror, I was happy with the result and opened the door to the waiting man.

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