Brianne Rides Again Pt. 02

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Crossdresser gets more than she bargained for.
1.2k words
4.57
51.6k
18

Part 2 of the 2 part series

Updated 10/24/2022
Created 08/06/2007
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Part II: The Rest Stop

As I debated on whether or not to go home or continue the night as a cross dresser on the hunt for a good fucking, I couldn't help but let the lust get the better of me. I once again climbed out of my car and walked along the long line of semi's parked in a row. I walked by them all and not a one of them made any sort of sign like they were interested. I couldn't tell if they were asleep in their cabs or just not interested. I went ahead and walked over to a picnic table, which actually happened to be the same one I got fucked on a month earlier. I lit up a cigarette and sat there with my legs crossed enjoying the night air. A few moments later I heard a truck door close and I saw a dark figure walking toward me. As he approached I couldn't really see his face, but he asked me how much. I couldn't believe my ears, I had never charged anyone for sex before, but it seemed like a good idea if he was asking.

I went ahead and made it sound like I knew what I was talking about and said twenty for a blowjob and fifty for a piece of ass. I really didn't know if that was a good price or not, but I thought it sounded good. Just then he slipped me a twenty and I put it in my purse. I felt obligated to give him the best head I could now, since he gave me money. I had never felt like this before, but it was actually kind of exciting. I knew there was a trail in the wood line we could go that was secluded enough, so I got up and we started walking back there together.

As soon as we got back far enough I immediately dropped to my knees, unzipped his fly and began sucking him the best I knew how. I did everything I knew would feel good and about five minutes later he was splattering my face with cum. He zipped himself up and thanked me as he began walking back up the trail. I sat there on my knees, just thinking to myself, "Wow, did I just become a prostitute?" I cleaned my face up and reapply my lipstick, which is a must after blowing two cocks.

As I emerged from the wood line I noticed the guy I just got done servicing over by the picnic table I was sitting at. He was not alone, there was now a group of about five or six men. I didn't know what was going on, but now I was really scared, but I thought maybe it was the cops ready to bust me for prostitution. Then I noticed that it wasn't cops, but more truckers, and my last customer was giving them the prices I told him. I didn't know what to think, should I really go through with this if these guys are interested?

I noticed that they had all spotted me and they were waving me over, so I slowly walked up tocking my high heeled boots on the sidewalk as I swayed my hips and ass. I couldn't believe it, these guys were pulling out money, and it wasn't twenties. They wanted more than just a blowjob. And from the way they were talking they didn't want it individually. One guy gathered up all the money which came up to a few hundred dollars and they handed it to me. A lump formed in my already cum coated throat, and that knot in the pit of my stomach increase, but so did the feeling of lust that flowed threw my body. I looked at the group of horny men in front of me and said, "Let's party boys."

Before I knew it their hands were all over my body and I felt my skirt loosen and fall to the ground. They guided me to the table that I had ended up on a month ago, and now I was on it again with not one, but six hardened cocks ready to plow me with everything they had. They laid me on my back on the edge of the table pulling out there members and shoving them at me left and right. I was so overwhelmed by the cock that I immediately just started sucking and jerking them the best that I could. I felt one of them taking my thong off and spread my legs apart. I could see a line forming behind the man between my legs. All I could do was service the two at my head while the first guy began to enter me. I sharp pain shot out as he pushed into me, but there was nothing I could do except let out a scream that they took as pleasure. He kept going, deeper and deeper into me until I felt his balls slap me in the ass. He pulled out and rammed it home again, I felt my whole body shift as he fucked me. The pain soon turned to pleasure and my moans reflected it as I sucked the two dicks shoved in my face. He must have been deprived of sex because he lasted about 5 minutes before blowing his load deep in my ass. I could feel it dripping and running down me.

He pulled his cock out and the next guy stepped up, this time putting my legs on his shoulders holding them with his hands thrusting his huge member into me. He was definitely filling me up as he pumped me like a jackhammer. I could barely hold on to the cocks at my face trying to give them a decent blow. He was a big man and had total control of me. He knew how to fuck and he was doing it hard and fast. Instead of blowing his load in my ass he pulled me off the table onto the seat, shoving his cock into my face. He grabbed my head and said, "Suck it bitch." I took it into my mouth and sucked it like a little whore running my hand up and down his shaft as I gave him head. He rammed it unexpectedly to the back of my throat holding the back of my head. In shock, I tried to pull away, but his massive arms gripped me tight as he grunted a huge load into me. I tried to swallow what didn't go straight down my throat, but most of it ran out onto my chin.

After he moved out of the way the next customer had me turn around with my knees on the bench and lay across the table. He fucked me doggy style as did the last three who were awaiting there turn. Each of them planted there seed inside me, and by the end of it, my beat up hole was so loose and wide that all the cum just ran out. My buns felt wet and slippery as I lay there, bent across the table. I could hear flies being zipped as I began to get up. They all, without saying a word, walked away smiling, leaving me there, covered in cum, to pick up my clothes. I figured it was just as well, I mean, they did pay for it.

For a few days after that encounter I was sore as ever, but thoroughly satisfied. I didn't know if I'd ever do that again, but it was fun at the time. I was truly turning into a hooker, and I loved every minute of it.

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AnonymousAnonymousover 10 years ago
great story

I wish I would be fucked by a group of truckers while I'm dressed in my sexy clothes. I have had a 3-some twice -- sucking one cock while the other guy fucked me deep & hard, and then they switched positions. I truly felt like a slut -- AND I LOVED IT !!! Please tell more stories like this one. It really turned me on.

pammycakes13pammycakes13over 11 years ago

fabulous!....you could write longer stories....!!!.........you are GOOD!

AnonymousAnonymousover 15 years ago
Voyeur

I saw a similar thing happen, 4 truckers one after the other fucking a women at a truck stop.She would suck them first, then they would move around, lift her legs up and fuck her while she lay on the table.I was watching, pumping my cock, when i heard a voice, why dont you have a go. Another trucker, said after they had finished, she was all mine.He went over ,pulled his cock out and fucked her, then when he was finished he turned and beckoned me over.He told me to let her suck me first, so i positioned my cock at her mouth and she took it and sucked me until i was rock hard.I pulled out, went around got between her legs, lifted them and then i saw the cock.They had been fucking a tranny, something i had not done.I looked around, go on give it to her, my cock was rock hard so i positioned my cock at her hole and pushed forward.My cock slid into her well used hole easily.I grabbed her legs and started to fuck, cheered on by the truckers, i really gave it to her, pushing up into her hole hard and fast,she groaning,as her cock got hard, i fucked her harder until i heard her scream and her stiff cock sprayed cumm up into the air.This made me shoot my load up into her well used channel pounding into her as i did so.The truckers cheered as i pulled out, my cock emptied.It was great and they told me to come over anytime.I have.

AnonymousAnonymousover 16 years ago
Damn, that's hot!

Too risky for for reality, but purrrfect for fantasy/fiction. This writer's stories are hot, short, but hot.

Dana23Dana23over 16 years ago
Wow!

Great story! I wish truckers were so ready for crossdressers to take care of them:)~

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