Parking Area 2 Miles

Prior to writing this next installment in my awesome sex life as a bisexual crossdresser, I thought I had already written about all of my worth while, true life experiences, but I had actually forgotten about this one.

It happened in, I believe, 2008, during the end of the summer. I was driving my truck. I am a truck driver by trade. Three hours and a coffee after leaving my pickup point for my load, I needed to piss. Ahead was a parking area, according to the signs along the highway. "Parking Area 2 MiIes". I needed a stretch too, so it seemed about time for a rest break. "Parking Area 1 MiIe".

I pulled into the area for "Trucks, Trailers and Buses". It was dark, but still relatively early, and I was the only vehicle in the truck parking area. This would prove to be excellent timing. Now, if you've read and are familiar with my stories and my background, you know that my stories are totally true, and accurate to the best of my recollection. I may begin writing about my fantasies and 'solo' happenings in the near future, and when I do, I will be sure to properly categorize them as fiction, fantasy or solo. This story you're reading now is another true story that happened to me simply by the dumb luck of being in the right place at the right time.

I had my pick of spots, and chose the one right in front of the bathrooms, so I wouldn't have to walk that far. In the back of my truck, in the sleeper, is where I have all my stuff for the few days at a time I'm on the road. I was lucky in that I wasn't a long - haul driver who was gone for weeks at a time. But I WAS lucky, as it would turn out, to have a sleeper truck. In the midst of my stuff, of course, was my bag of women's clothes and shoes. I never leave home without my bag of goodies! And condoms too, of course.

I get out and lock the truck. I'm walking into the building, enjoying the peace and quiet, and the cool evening air. It was about 7pm and the temp was about 55. Had to be September. Still summer but not for much longer. In the building I continue, do my business and head out. But this exit stage left wouldn't be like any before, or unfortunately, since. Waiting outside was a large man, probably about 50 or so years old. He struck up a conversation with me, asking how I liked driving truck and telling me how he used to drive too, but was now in the business of driving an escort vehicle for oversize loads. Less stress, he cited.

I wasn't in a great hurry, actually ahead of schedule, and he seemed nice enough, probably just wanted someone to talk to for a few minutes. So talk we did. He told me some stories about what he used to do when he stopped at truck stops, rest areas, and other public places where a truck could fit. He didn't come right out and say it, but reading between the lines I knew what he WAS saying...that he liked screwing around with men! He then looked at me and asked me, "What are you looking for?". I answered his question WITH a question, and asked him "What are YOU looking for?". "I...like to...I like to suck cock", his head kind of tipped down and his shoulders seemed to hunch forward, in a shameful admission.

I then surprised myself, without hesitation, saying "Well, I like getting fucked in the ass". This kind of surprised him, lifted his spirits a bit, and he smiled and asked if I'd like to go back inside and he would gladly fuck me. Well, I told him it was too risky to do it in a public john, and that I had a truck with a sleeper that would be safer and more private...and that I was a crossdresser and had my stuff in the truck. I asked him if he was OK with me dressing up in women's clothes. He was totally cool with it. Holy shit, I couldn't believe this was actually happening! This was the first time ever, and so far the ONLY time, where I hooked up without soliciting for it with an ad in the paper. Every other one of my experiences have been planned.

I told him to give me a few minutes to change into my female attire. He agreed and told me he prowled this rest area with a friend, and asked if I wouldn't mind if he got in on the action as well! Of course you know my response! TWO fucks for the proverbial price of one? He'll yeah! This couldn't get much better now, could it. I went back to my truck and stripped the clothes that I wear only because society SAYS I, as a man, SHOULD wear, and replaced them with the clothes I WANT to wear, always! I pulled on a pair of black, sheer opaque footless tights over my black panties (wear panties 24/7), black velvet miniskirt with matching 3/4 sleeve sheer top, and finished off the outfit with a pair of 4" black 'ballroom dance' shoes, with the strap, closed heel and toe with open sides.

He knocked on my truck door just as I buckled the last strap on my shoe. I let him in and he said how much he liked what he saw. Then he broke some bad news, his friend didn't want anything to do with a man in drag. Damn shame! But certainly not a total loss. He sat in the drivers seat and didn't waste much time, which was fine with me. He lifted the front of my skirt and pulled down the front of my tights and panties, and took my cock, which was nice and hard, in his warm mouth. I've NEVER cum from a blowie, from any woman or man, but I came close this night! I almost fucking came in his mouth! I would have had he not sensed it and stopped. I was never that close ever before, so I didn't even immediately recognize what almost transpired.

We then moved into the sleeper part of the truck, and onto the bed. I pulled down the back of my tights and panties and got on all fours. He put on a condom and entered my ass, oh how awesome a feeling that is, I never tire of it, that initial pain, as my asshole stretches to accommodate a lover, being the woman I wish I was, pleasing any man who will let me. After a few minutes, he pulled out and rolled me on my back. He grabbed my ankles, which is a HUGE turn on for me, lifted my legs over his head, and without missing a beat (or more importantly, without missing my hole!) he re-entered me like a porn star pro! My ankles behind his neck, his cock pounded my ass relentlessly, and I wouldn't have wanted it any other way! When he finally came, he drained of all color, actually worrying me for a second (I really didn't need to explain why there was a big guy on top of me, dead of a heart attack lol), but all was OK. I love how a cumming cock feels when it pulsates against the ring of my anus!

He left shortly thereafter. I didn't bother changing out of my outfit. I hit the road, still wearing the clothes I just got fucked in.