Truck stop sissy prostitute
My wife turns me out to make money at the local truck stop.
When my wife Wanda finally felt that I was ready to earn money for her as a crossdressing hooker, she drove me to the local truck stop. It is a pretty big place on the interstate highway and at any given time it may have 10-20 trucks parked there. Some are there to eat the greasy food and some are just filling up their tanks. A few are parked out in the lot where they are sleeping before getting back on the road. Wanda had been preparing my "boi pussy" for weeks by making me wear a butt plug and pegging me with her strapon. She had purchased a variety of clothes for me to wear as well as three different wigs. She had gotten pretty good at applying makeup on my shaved male face, and unless you looked closely, I did look a lot like a female. I had been practicing my walk and also had pretty much perfected speaking is a higher pitched but soft voice. This night I was wearing a leather skit with black leather boots over sexy mesh stockings. Underneath my skirt I had on a garter belt, bikini panties, and a black bra. Wanda waited in the car as I approached the first trucker. He looked me up and down and said that he was sorry, but he had to hit the road. I was turned down twice more before I finally found the right guy. He was a big white man wearing a cowboy hat and I walked up to him just as he was getting out of his truck cab. He got right down to business, "How much." I told him 75 for a blow job or 100 for a fuck "which is what Wanda had told me to say." Without hesitation he said, "Let's go" and held open the door of his truck for me. I climbed up into the cab and scooted over to the passenger side. When he settled in under the steering wheel, he handed me a hundred dollar bill. I tucked the money into my bra and scooted across the seat and reached for his crotch. I unbuckled and unzipped his pants, and pulled out his cock. It was already half hard and was good-sized. As I bent over and began to suck and stroke him, he kept repeating "Good girl! Good girl." I could tell that he was enjoying my efforts because his hard dick was throbbing now and a bit of pre-cum was leaking out. "Let's climb in the back and fuck," he said. "Before we do, I said, there is something I need to tell you," I said. I wasn't sure how he was going to take the news about the cock between my legs. "You mean that you are a tranny?" he replied. "Yes." "Honey, that's why I said yes." Let's get in the back. We both crawled back into the bed behind the seats and he began to undress me. He unhooked my stockings and slipped off my panties. Then he took his hand and reached out and took my little dick and began to lick the head. I was astonished. It never occurred to me that he might want to do that. We sucked and stroked each other until my little clit was rock hard (not something that happened very often) and then he lubed up my boi pussy with something from a tube and began to slide his hard dick into me. It was heavenly. I was finally being fucked by a real man. Wanda had pegged me and fucked me with dildos for months, but the feel of a real man's cock inside me was just delightful. He pounded my ass, shifted positions, and pounded some more. My own dick was leaking cum and I knew that if I just reached down and stroked it I would spurt all over the place. Then I felt his hot cum spurting inside me. He was jerking his hips and moaning until he collapsed . "That was very good, darling. I'll be back through here next Sunday night. Would love to see you again." I was now officially a tranny prostitute. Before he left he kissed me on the cheek and patted my ass. "You were terrific!" he said. I headed off across the parking lot to find Wanda. I had a lot to tell her.
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Comments (14)
Paul: I look like a big biker type guy but im a nasty closet tiny limp dick sissy faggot. Im a nasty pig. I wear panties and a bra almost everyday. Even when i go to the doctor knowing im getting checked out. I put a ad online and sold my ass just like that. One night i had to do my makeup, wear a wig, panties and bra. I went to this black guys hous. He made me walk to the door just like how i was dressed, im not passable. He took me into the basement and handcuffed me down to a table. He started to face fuck me. About 20 min goes by, i heard someone come in the door. About 6 black guys came down the stairs. I knew i was in trouble. I was r@ped and held down there for 3 days. I was pimped out. I would have to say about 50 or 60 guys fucked me. When i finally left i could barley walk, couldnt close my legs. I was covered in cum, piss and spit. They did some nasty things to me. Becareful.
Reply↴ • uid:b9mh649cAhmed: I hate gays
Reply↴ • uid:7b6jlcjk0jSecrets: I would love to watch the two of them sucking one another and then the real deal. My panties are wet and would want to join them.
Reply↴ • uid:1eqibdaiyunkCuckoldtoilet: I was fucked hundreds of times when i was a tranny and dressed as a woman, especially when I was a tranny prosititute in Walkden in my mid-40s (see my stories). But from my teen years till today, I've always preferred to be fucked naked. Men are a lot more rough when you're naked.
Reply↴ • uid:1e9xs78ck7i1Longjon: When I was young I was dressed as a little girl and fucked by our neighbour and his friends I went home dripping with cum and always went back for more
Reply↴ • uid:1ckio0qct8puQ: Everybody needs their boi pussy fucked at least once
Reply↴ • uid:22lr6fskqlBeachboy: Hmm well okay I guess I just need to know what to do with the first one to let me try it in the back seat of his car and then maybe I will be able to put the little skirt on my sweet little virgin tight ass and let him make me a little bitch with cock in my mouth so beautiful to talk about it and it makes me feel better about the things I want to try and see what it feels like and how it tastes when I get the hang of this before I look for a man that is so big and the things that I want him to do with me hmm so sweet to do that with a strange first time
• uid:1dd7itf0vh02John Robert Maybury: I cannot understand why anyone would want a man dressed as a girl. If you want to fuck a boy, you should want someone who looks like a boy.
Reply↴ • uid:1qkwnvqd99an: I am bi myself. I fucked boys when I was in my teens, then girls. I love fucking pussy and ass from a woman, love BJs from them. I also like BJs from guys and they do have an ass to fuck. I now got the best of both worlds. My wife is thin, straight body at the waist, beautiful face, and pert little ass. She has zero tits, her chest is totally flat. With no makeup, short hair she can pass for a young boy. She had her bi days also in her past so she understands. She will dress in boys tee, jeans, tennis shoes, underwear and lay on her belly with that cute, smooth ass sticking up and I fuck her. She and I talk like I'm fucking another guy and she gets into it. Sometimes she wears a small cock that hooks around and up into her vagina and will turn around and fuck me with it. Not the same as a real cock, but on her it looks good.
• uid:1d5v08htb8mlHarrisonSword: In my case I prefer women but I also like sucking cock. With a convincing tranny you get the best of both worlds. A smooth, skinny twink with a pretty face is also acceptable even if not cross dressed. A hairy masculine male? Ugh!
• uid:1eca36ov4gsxMike: Paragraphs please
Reply↴ • uid:libmv5jwm5uJ: Why?
• uid:7b6jlcjoi9John: Why Mike?
• uid:t2pu7wqd9bJ: Hello Mike.
• uid:4bmz0tu0k09