The Hitchhiker


The Hitchhiker - October 7, 2010

I've sometimes passed guys hitchhiking and fantasized about picking them up and seeing if that would go somewhere, but I've always hesitated, really I'm more interested in transvestites like myself than men. On a recent rainy afternoon though, heading home from a trip, I was particularly horny. Driving slowly through a busy little town I saw a young guy hitching a ride. As it was raining hard and he looked cleancut I decided to pick him up, quickly deciding this guy would be "it".

He was cute, with a full crop of longish blonde hair parted in the middle, soft features, a small guy, quite thin, wearing clean but torn jeans. He looked shy. I gave him about 18 or 19 years of age. After asking where he was going, I told him I wasn't going very far but it might help. He said that would be great, he'd been waiting a while but it wasn't bad as it was warm but wet.

We talked a little about his school classes and I steered him towards the girls he knew, trying to arouse him. Shortly we arrived at my turn off point and I decided to pop the question - I told him if he would do me a favour I would drive him all the way to his destination, three hours further on. He stammered "Well what do you mean?" I kept it straight and simple "If you'll let me blow you, I'll drive you home. And don't worry, I don't expect anything in return, I just want to suck your cock". He didn't seem shocked, but didn't answer. I continued "You'll have fun, no strings attached, and you can see I am clean, healthy and in good shape". He paused still, probably weighing the time of day, the rain, and the blow job.

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   He finally muttered without looking at me "Well ok, but where would you do it?" I told him I often stopped to masturbate along this highway so I knew a few isolated side roads. He nodded. As we drove on I asked him if he'd mind me touching him, and he said no. I reached across the seat to touch his thigh, massaging it gently as my hand moved higher. He wasn't relaxed but didn't squirm at all, just watched as my hand reached his little bundle, I could feel his balls and cock through his jeans. It wasn't little for long, I could feel his cock stiffen and he laid his head back on the seat and closed his eyes.

I continued to massage his cock as I drove and he seemed to be enjoying it. After a few minutes, I turned off onto a dirt road I know well, driving far enough into the woods so the car wasn't visible from the highway. Stopping the car I leaned across the seat to put my cheek against his groin,then opened his crotch and extracted his cock, now rock hand. Hewas well endowed, at least eight inches and very very thick. He was also clean and clean-smelling, I liked that a lot. I was slow and gentle, and talked slowly and in a soft voice to him as I handled his beautiful cock and drew my mouth to it. It was already oozing pre-cum. I had to work my lips around the head before I could get the whole wonderful thing in my mouth. He didn't last long, in two minutes or so he blew a large load of tasty cum into my mouth.

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He groaned and his face contorted when he came, he was gorgeous. I think he expected me to remove my mouth and spit it out, but I took every drop and stayed on him until he was dry. Though temporarily satisfied, he didn't get soft immediately, so I kept playing with him, my arms reaching around his ass and pulling down his jeans, hugging him closely to me, my tongue moving softly and thoroughly to his balls and thighs. Within moments he was hard again, but this time I slowed down to stretch my pleasure and his as much as possible. I stayed away from the head, instead licking the sides of his cock and his balls. As I played I looked up at him, he was really a beautiful blonde boy. His lips were full and I wished I could kiss them. I reached up and ran a finger around their full form. "I couldn't kiss you could I?" "No, I don't think so" he answered, "I've never kissed a guy before"

A bit disappointed, I returned to sucking his cock, first licking a finger and reaching my hand into his pants and under his ass. As I sucked and slobbered, I played with his asshole, gradually slipping my finger into it. He squirmed a bit at this but didn't stop me. In a few minutes my finger entered and started massaging his prostate. He quickly came again, a bigger load than the first time, this boy was going to make a great man. I was full of his cum and wanted more but time was moving on. I licked his beautiful cock and my lips clean of his delicious cum and looked up at his eyes, which were a bit glazed by now.

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   "Have fun?" I asked. "Yeah that was real nice, that's the first time anyone's ever done that to me" he said. "You mean you've never been with a girl or a guy before?" "No sir, I haven't"

We both straightened up as I started the car and got back on the highway. We still had a few hours to go and we might make a couple more stops along the way - I was determined to get that big and powerful young cock inside me before we got there. But alas he avoided any further sexual talk and eventually we arrived at his home town. As I dropped him off at a corner he surprised me when he asked "If I ever go down that way again and need a drive, could I call you, would you mind?" "Mind", I said "of course not, it would be my pleasure, and yours too - You could even come have supper with me, I'll have a very special surprise for you next time, you'll love it!" I was hilariously happy - nest time we would meet I would be dressed as a woman and he would find that easier. It looked like I am the "woman" who might take this blonde beauty's virginity!