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Hitch-hiking Baby Doll: Part Three

My cross-dressing cross country trip continues with my trucker stud.
When it comes to getting men to want to fuck her, a girl has to put her ass to good work. I discovered this when I was eighteen and first started being a tranny hooker around the adult book store. I was wearing my first miniskirt with a thong panty underneath, walking down the street. My ass cheeks were hanging out of the bottom of the miniskirt and men were slowing down to look at me, blow me kisses and talk to me. It wasn't long until I was in their cars and making money sucking them off or letting them suck my dickie.

Tonight, in a hotel room with my handsome trucker stud who was driving me across the country in drag, I was ready to act like a sexy little tranny hooker for him and let him fuck me hard the way he wanted to so bad. Being a tranny hooker always made me more naughty with men, so it was time for me to be naughty with this one.

I came out of the bathroom into the hotel room wearing my sexy black stilettos, little black miniskirt, halter top and thong panty. My miniskirt had a little studded silver belt through the belt loops, making it seem even sexier. The swagger in my step let my trucker stud know right away I was ready to do him good. That's the trick of a hooker's walk, being sexy and self-confident turns men on.

"I love kissing your lips, but the little whore in me can't wait to kiss that big cock of yours, you big stud."

"You sure look good in that hot outfit, baby doll. You make a cute little whoreboy."

"I know," I said. "I've been fucking men for money ever since I was eighteen."

"You'll do good in L.A. dressed like that."

"I want to do good here, tonight, in this room you big stud."

"How much do you charge for blow jobs?"


"How much to fuck you in that hot ass?"

"One hundred."

"How much to spank that ass of yours while I fuck you."

"It's free for you, you big stud. Other men aren't even allowed to do it."

He got a big smile.

"Oh, nice, I'm going to enjoy this," he said.

"First you have to pay me, stud."

"Oh, right," he said.

He reached in the night stand drawer and pulled out a hundred and fifty dollars and I was no longer pretending to be his little whoreboy, I was definitely one to him. And he was glad to pay me so he could spank me hard and treat me like a whore. He had told me he wanted a wild fuck and he wanted to spank my ass and I figured doing it to me as a bad girl hooker would be fun for him. So what if it cost him a hundred and fifty dollars? I was determined to give him his money's worth.

He had just had his cock in me in me while I wore my little pink lace thong and baby doll teddy for him. Now, in my black miniskirt and black thong panty, I was ready for him to fuck the shit out of me like a cheap whore likes it from a man. I would call out "Fuck me, baby, fuck me hard," while he pounded his cock inside me and spanked my ass cheeks.

"You're being bad and going out and being a little hooker and not staying home and giving your Daddy pleasure, Missy," he said. "Come over here and let me spank that hot little ass of yours while you bend over in that miniskirt for me."

"Oh, Daddy, I like getting lots of cum from lots of men. I was only being a little whoreboy for you because I thought you like me being one."

"I only like you being a whoreboy with me, not with other men. Now, bend over and let me have at that hot ass of yours."

While he raised his hand, I bent over for him and raised my ass cheeks high in the air while he held up my miniskirt so he had full access to my ass.

"Oh, Daddy, don't hurt me," I said.

"This is for your own good. You have to stop being a whoreboy for other men and only be one for me."

"Oh, Daddy, I'll be your whoreboy any time you want."

"First, I'm going to spank you. Then you're going to suck on my cock like a good little whoreboy. Okay. Missy?"

"Okay, Daddy."

In one swoop his hand hit my ass cheek in a loud smack and I jumped forward. I looked at my trucker stud's big ten inch cock and saw it getting harder, all the sudden. Apparently, smacking my hot ass was turning him on, so I was glad to let him even though I'm not a masochist.

"There," he said. "Now, that will teach you to stop being a whore for so many men, little girl. Your Daddy wants you here sucking his cock, not out sucking on other men."

"I'll be glad to suck on your cock for you, Daddy," I said with a smile.

My ass cheek was bright red where he hit me and it was stinging and I was just glad it made his cock harder when he spanked me. Now, his cock was good and hard for me to suck like a dirty whore. Then I would let him fuck me as hard as he wanted as long as he wanted, letting him know how much I enjoyed it while he did. This was the art of being a tranny hooker, making your client think that whatever he did to you was your favorite thing to do.

"I love your big cock, you big stud," I said as I climbed on the bed next to him. "I bet you there's lots of other little whores out there who wish they were in bed with you, right now."

"Just come over here and suck it like a dirty little whore and I'll tell you when to stop," he replied.

Girls get really good at sucking cock with practice and whores get lots of practice, so a man always expects a good blow job when he pays a whore. Being the good little whore I was, I always wanted to please the men who paid me to blow them. A happy customer was sure to come back.

"When I come in your ass today, Missy," he said, "It's going to be the most cum you ever had in you. We've been fucking around for over an hour and I still haven't cum, yet."

"I loved cumming on your face. It made you my official CumDaddy," I said.

"I'm going to love cumming in your ass. But first, I want you to suck me like a good little slut."

"I love having you fuck me in the ass. Do you fuck other girls in the ass?"

"All the time," he said. "Most whores' cunts are so worn out, I can only get off if I fuck them in the ass."

I loved being fucked like a girl from the front, too. But from behind, he could be more aggressive and fuck me harder while our balls slapped together. That was how I wanted to be fucked by my trucker, at that moment, hard and aggressive like a stud. As a tranny hooker, I learned to imagine that every cock a man gave me he was giving it to me for my pleasure, so I learned to enjoy the moment with every client. This was entering my mind as I approached my trucker stud's big ten inch cock.

My theory was that every cock deserves to be sucked and, if you're getting paid to suck one, you should suck it really good. That's how I approached my job. In this case, I wanted my trucker stud to put his hands behind my head and force me to swallow his whole cock which was so big it barely fit in my mouth. Taking his cock in my hand, I looked up at him and licked my lips.

"All you big studs need a good little whore to suck it for you. So I'm glad to be your little whore, tonight. I want to suck it all the way down for you, big boy."

Some people think tranny boys want to be girls. With me, it was a matter of imitating them when I was with a man and doing everything for him I thought he would like a girl to do. This created a connection in me that made me feel just like a girl by having a man accept me in their clothes and let me do to him what girls do.

This whole sexual experince with my trucker stud had started when he said that he had a girl and guy riding with him and enjoyed getting blow jobs from both of them. Being the girlyboy I was, I was glad to be his sex buddy the whole trip and dress up for him all the way to California. We would make each other cum, morning, noon and night, for a whole week.
We had more sex in that week than some married couples have in years. And the reason was because my stud was so terrific and, like any slut girl, I just had to have as much of him as I could. I kept wearing different panties for him, sometimes ten different pairs a day, and turning him on, again and again. He loved me being his tranny hooker the most. He said I was the best paid cocksucker he ever had.

As I sucked on his cock like a happy little hooker, he swung my ass around and started plying with it under my miniskirt. The more I was with him, the more of an ass man he was getting to be. And I was proud of my hot ass men liked so much. So, I was glad my trucker liked my ass so much and I liked that it made his cock harder when I was sucking it if he played with my ass. If a man's big cock wasn't fully hard, it was harder to suck since it kind of flopped around in your mouth. So, I liked to keep my men fully pumped while I sucked it for them good.

To me, wearing panties and sucking on a man's cock came naturally and I could never understand about people worrying whether it was wrong. It felt good to me to be who I enjoyed being and whether it was right or wrong was other people's problem. All I needed was another pair of panties to wear and I would be whoever my trucker stud wanted me to be. He bought me over a fifty pairs that week and I wore every one of them for him and turned him on.

Counting all the times we did it without me changing panties, I made my trucker stud's cock cum several hundred times that week. It was excellent practice for becoming a tranny hooker in L.A. I loved having men give me money to wear panties and turn them on like a girl. My trucker stud had just paid me to suck on his big ten inch cock and I was going for it good for him.

I enjoy sucking on him and fucking him all day and night for a whole week on our trip. He stopped to do me in hotels every night and we only drove in the day. That's how much he wanted the week to last with me. I was very good at pleasing him, he told me, even better than the girl and guy together had pleased him the week before. I sucked on his cock even more than the guy did and the girl didn't swallow. I loved to swallow for a big handsome stud like my trucker.

When a man comes in a girl's mouth, she knows how much she's pleasing him by how much cum he shoots in her mouth. A guy who's really horny for her shoots lots and lots of cum, so I learned to gauge how much I pleased men by how much cum they shot between my lips. This stud definitely had the hots for me because he shot lots of big loads for me, in my mouth, in my ass, all over my face and tits. I really was a happy little cumcatcher for him all week.
I did lots of role playing for him, including beiing a Vegas showgirl in red panties with fluffy tassels and sequins on them. As a Vegas showgirl, I like to kick my legs up high and show a man my sexy thighs and what's between them. It doesn't take long for him to want me to sit on his lap so he can play with my tassels and get in my panties.

I also loved wearing my orange sherbert panties, seethrough panties that gave me a thousand sensations every time he licked me through them. Of course, I loved wearing lots of Barely There panties for him. Those are so soft and sexy he couldn't stop touching me through them. Being touched and licked through my panties by my big strong trucker all the way aross the country was a special treat for me.

I liked the way my trucker stud licked me like I had a pussy down there, taking my whole dick in his mouth and sucking on it like it was a clit. I loved him giving me mustache rides. Sitting on his chest and putting my dickie in his face was a lot of fun for this horny little girlyboy. He made me feel like a sweet girl. But now I wasn't his sweet girl, I was his tranny hooker slurping on his hard cock like a hungry little whore.

"I bet you're a good little whore for the boys when you're not with your Daddy," he said.

"I suck them all really good when they are paying me, Daddy."

"And you wear this sexy little miniskirt and show them your ass, too, don't you?"

"That's what makes them want me like a girl, Daddy."

"Well, I'm going to have to spank you for making them want you lke a girl. You're making me want you like a girl, too. This hot little ass of yours turns on lots of men, I bet."

"Yes, Daddy, lots of men see my ass and want me to suck them like I'm sucking you."

"Well, I'm going to have to spank this ass again to make you stop showing it off for other men like a little whore."

He rubbed my ass cheek with his hand, feeling the spot he planned to smack me. Then he pulled back and swung his hand hard into my ass cheek.

"Oh, Daddy, you're hurting me," I said.

"You're going to learn only to suck your Daddy like a little whore. And not to be sucking other men. Now, suck my cock for me and make it feel good."

"Yes, Daddy, I'll suck it good for you."

Even though my ass hurt from being spanked, it felt good to be sucking on my Daddy while he got my ass ready for his big hard cock. I was ready for him to give it to me rough like he wanted to. His cock was extra hard from being turned on when he spanked me, so I was going to enjoy having him fuck me for a good long time tonight.

"That's it, baby doll, suck that cock good for your Daddy. He loves your ass and wants to fuck you in it good. A few more smacks and he'll ready to put it in you."

Guys always think a girl who likes getting fucked from behind in the ass is kinky. And when it is a guy pretending to be a girl who likes being fucked from behind in her ass, it is even kinkier for them. I found that every guy who liked fucking girl's asses also enjoyed fucking mine since it is just as hot as any girl's ass. So, the kinky pleasure of getting ready to bend me over like a girl and fuck me hard was driving my trucker stud wild, right now, and he couldn't wait to put it in me.
This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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