I've been crossdressing since I was 20 years old.One of my favorite things to do is get all dressed up in women's clothes and drive around on the open road.
Several years ago I was mad at my ex wife for doing some stupid shit with our checking account and we were split up for some well needed cooling off time.The more I got to thinking about her stupidity the more I got to smoking some pot and drinking a few mixed drinks to get the crap off my mind.I got pretty stoned and decided to get dolled up.My legs and body hair already smooth shaven and toenails painted a bright red,I decided to put on some lingerie that my wife bought for me,a black lace cami with matching garter belt,thong panties and silky sheer black stockings.I got feeling pretty sexy and slipped into some 5 inch open toe thin strap high heels,that really got me going and I reached for my favorite wig and put it on as well,one thing for sure my ex wife had good taste when it came to dressing me up.Now I put on a skimpy mini-skirt and thin nylon blouse,before I knew it I had applied make-up the best I could(I never was real good with the make-up),I thought I looked good enough to pass as a woman myself and back then probably could.
I was feeling so sexy and decided to go for a drive,I love driving around dressed up like a woman.I headed for Memphis just to feel the night air against my feminine feeling body.I stopped at a station near the Interstate and filled up with gas and got some smokes,the clerk looked at me strange but smiled as she took my money and I pranced out to my car getting several looks on the way,that got me really hot and now I wanted some dick.I was not on a mission to be with a man,if I was my steady boyfriend would have been happy to let me suck and fuck him but I was already heading to Memphis and it wouldn't be long and I`d be there and I knew where a really good gay bar was and might get lucky there.
I stopped at a rest stop just about twenty minutes out from Memphis to smoke a joint.I pulled towards the back and parked where there were no other cars around.I stepped out of the car and walked about 200 feet to a picnic table under a canopy,although the area was well lit,there was just enough darkness that even if someone saw me they would not have known I was a man dressed like a woman.I sat down lit my joint and just admired how good them stockings and high heels looked on me.I was so caught up in myself that I never noticed this man walk up.He spoke in a soft well mannered voice saying,"damn I thought you were a woman but I see you are just a sexy wanna be girl".I was embarrassed because I did not see him coming and now what do I say or do?
Before I could say a lot he sat down and asked if that was weed I was smoking and I said yes,he asked if he could hit it and I simply said yes,I mean I am in an uncomfortable position right then.He sat next to me and we finished the joint off and he started telling me how nice I looked and asked me to stand up and show him how I looked walking in my heels.I did and sat back down by him and he gently felt my legs and just the feel of his masculine hands rubbing against my nylon covered legs was enough to drive me nuts,I responded by rubbing his leg until I reached the bulge in his pants.I could feel his cock as it got hard and we started kissing and rubbing each other and I could tell he was well hung as I rubbed his stiff cock through his jeans.He had my cock hard as well and only the band around my panties was able to keep my cock from being exposed to the world.
He suggested that we go to his semi parked clear across the other side of the rest area and right out front where all the other trucks and cars were parked. At that point I just wanted some dick so bad I just said let`s do it.We both got into my car and I drove around to where his truck was but I had to park about 100 feet from where his rig was parked and walk the rest of the way.I was so horny that I didn't even give it a second thought.All I wanted was for this man to fuck my brains out and I knew that he was going to do just that.
I felt like a real woman for that 100 foot walk across the well lit pavement to where his rig was.He opened the passenger side door and helped me up in the truck so I wouldn't slip in my high heels.He made his way around the other side and when he got in the truck he eased over towards me and kissed me some more and my hand immediately went for his crotch only this time I was undoing his belt and pants to expose a massive 9 inch cut fat cock.I was stroking him gently and he asked me did I like his cock? I said I love your cock,he then eased my hand away and slid to the back cabin of his rig and reached up to get me by the hand and guide me back to him on the very comfortable bed he had in there.
When I got up on the bed beside him I finished undressing him and he was undressing me as well.I was completely naked before I knew it and now I had him naked as well.I was so impressed with his manly look and massive cock I just had to stare for a minute.We were stroking each others cocks so gently and rubbing our naked bodies together kissing like we were in love.Just feeling him stroking my cock and how good it felt to have him there with me with his tongue working in and out of my mouth and his hard cock in my hand I eased my way to kissing him all over his neck and chest,sucking his nipples as I worked my way down to his massive cock.I kissed his cock gently from the head all the way down to his balls.I sucked his balls as I stroked his cock and eased my way around for him to be able to suck my cock as well.
We were now sucking each others cocks pretty intently when I felt him start to thrust,I knew he was fixing to cum and so was I.He stopped sucking my dick for just a second to say,"I`m fixing to cum",I said me too but please go ahead and cum when he was ready.That said we resumed sucking each other when he exploded and I could barely swallow his cum fast enough to not lose a drop of his juices.He moaned so intently as he was sucking my cock really fast and I exploded in his mouth and when he had finally drained me he eased around and kissed me giving me my cum as well.Now we were both pretty sweaty,kissing and rubbing again and I could feel him getting hard again,I looked him in his eyes and said I wanted him to fuck me so bad and he said that he would love to do that because he never has fucked a guy before.It was`nt long and his massive cock was rock hard as he laid on his back I straddled him and eased his cock up my waiting ass,he was a bit larger than I had been used to but once I felt him get so far in I began to work my ass up and down the shaft of his cock and it was only a few minutes and I had all of his wonderful cock inside of me and I was riding him like a bucking bronco.I actually shot my load across his chest just feeling his cock inside of me.It was another 15 minutes of pure pleasure before he told me he was cumming and we both were thrusting so hard you could feel his body slapping my ass cheeks as he fucked me and he shot his load deep inside of me and I shot another load across his chest.
I could`nt take it no more I pulled off his cock and started licking my cum off his chest and eased down to suck his cock clean.All I could do is sit up light a cigarette and get my stockings and panties on.I was so satisfied and I knew he was too,I just looked at him and said thank you for a well needed fucking.I finished getting dressed and we kissed for a few more minutes and exchanged phone numbers before I made my way back to my car.All that I was thinking as I left his truck was,"I`m just a crossdresser wanting some dick on the road."
Needless to say I never made it to Memphis that night,but I was so satisfied having a man to make me feel so complete.