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Short and Sweet First TS Encounter

My 1st TS encounter took place back in the early 80s. When people still picked up Hitchhikers and Transgenders were not as out in the open as they are now. It wasn’t a grand adventure or planned out and executed with precision. It was a complete accident and it could have gone differently if I weren’t such a Pervert and wanting all kinds of sexual experiences.

I finished a job late on Friday and was driving home. A few miles from home I see a good looking woman hitchhiking . She was going the wrong way but I figured I might get a blow job out of it if nothing else, so I swung around and picked her up. She was a very pretty, soft spoken Latina with a nice smile. She told me where she needed to go, and I asked what she could offer for the ride.

She wasn’t naive, she patted my crotch and I pulled into a loading dock behind a major department store that was closed. She unzipped me and began to do some wonderful work on my swelling cock. Like anyone of my ilk, I began exploring, rubbing her breasts, thighs, etc. then I moved toward her crotch and she swallowed me whole and grabbed my wrist and just stopped right there.

Smart ass me decides to push the topic and says, “What’s wrong? Got something there you don’t want me to see? Maybe something like what you have in your mouth now?” She let my cock out with a plop, moved her hand and sat up with a somewhat guarded expression. Understandable, Gay bashing was a big thing back then. I shook my head, took my keys from the ignition and motioned her to climb in the back of my pickup truck.

Once there I stripped down and told her to do he same. She was just as beautiful undressed as dressed. Her cock was about 5 inches soft, smooth and uncut. I began stroking it and she hissed as her cock jumped to life and was now an impressive 7 inch and the foreskin peeled itself back. I don’t know what happened to me, but I was down on it without thinking. After a few minutes it began to throb and she pushed me off.

I was still rock hard and she told me I could fuck her ass, if she could fuck mine to finish off.
I agreed and to my eternal shame of the moment I came hot and hard as soon as the head of my cock popped into her ass. But a deal was a deal so I laid back and let her go for it. I had been pegged by my girlfriend before and this wasn’t as big, so why not.

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