From the time I was 16 until my ealry 20's, I was an avid crossdresser. Nothing made me hornier than wearing sexy lingerie and dressy women's clothing. I was young and very passable, actually way better looking as a female. Of course makeup when done properly does wonders. Although I considered myself bisexual at the time, I rarely, if ever had sex with girls. My first taste of cock was at age 13 and I was hooked. Of course I enjoyed as much sex with men as I could get which was frequent. There were some downtown venues that catered to the gay crowd and I was there a lot, since I had a fake ID. Not that they cared at all.

One night an older guy approached me in one of these bars and started chatting me up. He bought me a drink, flirted, complimented me, the standard pickup moves. He asks if I would like to go home with him. I was in a silly mood and said, "Yes, for 200". I was totally joking but he said ok without missing a beat. I was about to tell him I was joking, then thought what the Hell. It was a major turn on.

He lived in a nice condo not far from the bar and off we went. We got in his car and madeout hot and heavy for a few minutes, then arrived at his place a short time later. Once inside, he offers me a drink, and I excuse myself to go to the restroom. In the restroom, I primp a little and remove my jeans which underneath I was wearing thigh high stockings and sheer panties. I walk out in my high heels, stockings, panties and little half bra. I felt so damn sexy, my cock was throbbing. My date obviously enjoyed my look as well. He was all over me. We went straight to his bedroom and he fucked me like a whore for most of the night. If I'm going to act like a whore, I may as well get paid. :-)

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Anonymous

by Anonymous on Nov 6, 2016 at 7:29 AM

I'm 30, a 5'6" gay crossdressing guy. In drag I look extremely feminine, and freakishly like Katy Perry. In my early 20's, a friend of mine in the scene suggested I be an escort for $$$. As it was, I attracted str8 men like a magnet, and had many dates where I put out and was treated with expensive outings and gifts. So she hooked me up with this lawyer in his late 30's. He paid me $1300. for a night out (dinner, drinks, a hot club) with fucking and sucking all night. I did this a total of 21 times in 2 1/2 years, made over $30k, which paid off my credit cards, put a down payment on a new car, and paid for my last semester in college. I was also smart enough to give it up before I got into trouble.

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