I am a forty one year old crossdresser. I have dressed up in private since I was in my early teens, and I can get to looking pretty good, given enough time to prepare. But until recently, I never tried to venture outside. Last week one of my fantasies came true.
I was driving down the interstate late in the afternoon, and I decided that I could dress in women’s clothes after it got dark and not worry about being recognized as a man. So I stopped at a gas station and put on some panties, pantyhose, a bra and a short spandex dress that I had with me in the car. Then I put my regular clothes on over them.
I got back in the car and continued down the interstate, and as it got darker I began getting more anxious. When I decided it was dark enough, I pulled onto an exit and drove down a back road a ways. I stopped the car and took off my pants and shirt, and then put on high heels, a wig and makeup. I had to use the rearview mirror for this, so I couldn’t really see how good or bad I looked.
As I drove back down the interstate I got more and more aroused. When I saw a rest stop ahead, I decided it was time to be brave and stop in. I parked away from the other cars, and after a few minutes of building up my nerve, I got out. I pretended to look for something on the backseat. With my short dress, I gave everyone quite a show when I bent over. There weren’t many people there, but I did get a few looks from the guys.
I stayed about ten minutes and then decided that I’d better get going. I got back on the interstate, and as I drove on, all I could think about was how great it felt to be in front of people like that. When I saw the next rest stop sign, on a sudden impulse, I decided to stop there and try it again.
When I pulled in, I once again parked away from the other cars, and I got out just like last time. But this time I walked around like I was waiting for someone. There were more people at this stop, and the guys kept looking at me as they walked from their cars to the building. There were also some guys who just sat in their cars and stared.
Each time I thought someone was coming toward me, I walked back to the car. As I got braver, I went to a lighted phone booth and pretended to make a phone call. Suddenly a truck with two men in it pulled in next to my car. A young man got out of the truck and made a beeline for the building, obviously needing some immediate relief.
I stood frozen, knowing there was no way I could get back to my car without the other guy seeing me and perhaps realizing that I was not a woman. So I stood there, trying to look as if I was waiting for someone. Suddenly the second man stepped out of the truck and stood leaning against the front of it. He kept glancing at me, until finally he started walking toward me.
I turned away and tried to ignore him, but he walked right up to me and asked if everything was okay. So here I was with my low voice, hairy arms and muscular body. How could I ever expect to fool anyone? I had no choice but to attempt to be as feminine as possible.
I spoke with as high a voice as l could and told the trucker l was fine and I was waiting for someone. He said it was kind of cold out to be dressed the way I was. I was shaking from excitement, and I was actually very hot by then. I don’t know if he saw me shaking and thought I was cold, but he offered me his jacket. I told him I was fine just like I was and didn’t need it.
Then he asked if I would like to sit in their truck and wait. I just looked at him and said he must be kidding. Then he said if I preferred, we could sit in my car. I said, how did I know that he didn’t have a weapon and want to kill me? He leaned up against a tree with his back to me and told me to frisk him.
I just stood there, but he kept telling me to. I finally walked over and patted his arms and down his back to his waist. I stopped and said okay, but he said I’d better check his legs. I felt his ankles and up his legs. As I moved up, I continued to get excited. Instead of patting, I slid my hand a little way up his thighs.
When I stopped, he turned his head and asked me, hadn’t I better check in front for that weapon? Now I was to the point where I wanted to continue, so I walked up to him he still had his back to me and put my arms around him. I felt his chest and slowly moved down to his waist. Then he took my hands and moved them to his crotch.
Sure enough, I found his weapon. I asked him what kind of gun that was, and he said if I would go to the car with him, he would be happy to show me. I just stood there, not knowing what to do. Suddenly he turned around and kissed me. I’d had men give me head before, but I had never kissed another man. I must admit it was unusually exciting.
Then he put his arm around me and we walked to my car. His friend had returned and was sitting in their truck watching the whole thing. We got in the car and he kissed me again, only this time he used his tongue. As we kissed, he ran his hand up my hose covered leg to my thigh. I reached down and pushed his hand back, but he took my hand and put it on his crotch.
I could tell his penis wasn’t real big, but it sure was hard. As I undid his pants and began to stroke him, he put his hand on the back of my head and gently pushed me down. I didn’t resist, though I did wonder if I was really ready for this to be my first time.
I guess I was.
I rubbed his dick across my lips and face, and then softly licked the pre come off the tip. Then I slid it between my lips. I found I could fit it all into my mouth without much trouble. He pulled his pants down, and I ran my hand up his thigh to his balls. I tried to do everything the way I had had it done to me so many times before by both women and men. I would pull it out of my mouth and lick the shaft and then run my tongue all around the head before putting it back in my mouth.
As I went up and down on him, he pushed his hips up to meet me. Soon I heard his moaning getting louder, and he told me he was about to come. I was so excited by then that there was no way I was going to stop. I pulled my mouth away a little and opened wide as I stroked him with my hand.
Suddenly the first shot of come hit the top of my mouth and dripped onto my tongue. He continued to fill my mouth as I slid my lips slowly back around his throbbing member. I had tasted my own come before, but eating your own come can’t compare with having someone else’s hot, salty, sticky juice in your mouth. I continued licking and sucking until he was finished and got soft. I sat there on the seat next to him and we kissed again.
Then he told me it was his friend’s turn. I was still very excited, and I was more than happy, maybe even eager, to help his friend. The guy I had already done signaled to the other one back in the truck. When the other guy got in the car, he just pulled his pants right down, exposing a penis that was slightly larger than the first guy’s.
I began working on him, and the first guy began feeling up my thighs. I pushed him away once or twice, but he was persistent. I finally had to stop and tell him to give it up or they could both get out and leave. I will always wonder how it would have felt to have him plug me from behind and come inside me while I took care of his friend, but I couldn’t let him know that l was really a man.
He finally stopped, and I continued working on his friend’s dick. It wasn’t long before he was ready to pop. I continued to lick and suck him until he shot a huge load in my mouth. I swallowed it all and licked him clean. Then I sat there between the two guys.
They kept trying to feel me up, but I kept stopping them. If they hadn’t figured it out already, I didn’t want them to find out now that a man had just given both of them head. We sat there for a few minutes, and then I kissed each of them good bye and drove away. I will never know if they actually knew that I was a man. But I will always remember my first night out of the closet.
R.T., Gainesville, Florida