Original and true story...
In my teens I was one of those skinny effeminate types that every class has. I knew I was different as far back as I remember and I definitely liked other boys starting about the 7th grade. I got a hard on in the showers after gym class and all the other guys made fun of me. My best friend was another boy like me, Nick. Nick and I used to stay over each others house on weekends and what started as `I will show you mine if you show me yours' rather quickly turned into lets suck each other off. By 16 or 17 we were buying (and shoplifting) girls clothes, shoes make-up. We would play dress-up together then have sex and it was great fun!
At 18 Nicki and I wanted to move away from our parents and move in together but of course neither of us had a job or any money. We hatched a plan to get all dressed up sexy and cruse the streets looking for paying customers. The first night we dressed in miniskirts and high heels with lots of make-up and really red lipstick. We smoked a bunch of pot and drank vodka from a flask I had in my purse and were pretty loaded in an attempt to bolster our confidence. In only a few minutes I huge Lincoln pulled up and down came the drivers' side window. I nice looking guy about 50 introduced himself and said he was looking for a good time. I told him I can suck the chrome off a trailer hitch and he asked me to get in. I sat next to him and rubbed his cock till we turned the corner and drove down a deserted side street. He parked and I unzipped his pants and I went down on him and sucked away. This was actually only the second dick I ever had in my life, having only had Niki before this. I felt his cock twitch and out shot a big load of cum that I swallowed completely. He drove me back to where he picked me up and I got out of the car. As he drove away Niki asked me how much I got and only then did I think of it.. I was so excited/ high/ nervous that I forgot to charge him! Oh well, chalk it up to experience I suppose. Niki was approached next and she got in the car with two younger guys and took off. Soon a big pick up pulled up and I got in the car with him. He knew I was a boy and wanted anal sex but I told him I only do blowjobs and the price was $75. He gave me the money and I sucked him off receiving load number two in my mouth. When he dropped me off he said he would pay double for anal and I told him to come back when he was ready. He drove around the block and pulled up in front of me and said he was ready! I laughed and climbed in for another round. I slipped off my panties and used my hand to get him hard again. I wet my fingers and straddled him and he slipped his cock in my ass. Actually felt pretty good after the initial pain and I could tell my cowboy was enjoying the hell out of fucking my ass. I felt it squirt in my ass and I didn't want him to stop so I kept fucking him till he got too soft and plopped out.
We he drove me back Niki had returned and was leaning over a Corvette talking to a guy. He said he was trying to get a party together and asked if we were interested. As long as it's a paying gig we both agreed. He took off to try and get it together and Niki and I hugged and caught up on our evening so far. I made $225 despite the freebee and Niki made $200 by giving blowjobs to the two guys she was with. Not bad, less than two hours, great sex, and months rent already. Niki was surprised I got fucked up the ass because I was never interested in it before when she wanted to do me, but I assured her its my new favorite thing to do and she can have it anytime she wants! Speaking of which, somewhere I lost my panties and my ass was leaking cum so I had to use my hankie to wipe my ass crack. We both laughed and decided that was it for tonight so we headed home.
Back at our place we changed into sexy nighties and made love before falling asleep in each others arms.
At 6:30 the alarm went off reminding us we were still in high school and needed to get ready for school. We dressed in our drab boy clothes and scrubbed the last traces of mascara and lipstick from our faces.
High school boys by day, wanton transvestite hooker whores by night! LOL
To be continued..