tagTranssexuals & CrossdressersPimped Out in Vegas

Pimped Out in Vegas


I had flown out to Vegas for business and was staying at one of the hotels just off the strip, The Hilton. My business ended by 6pm every night, so I had some down time. The first night, I just stayed in and got used to the change in time zones.

The second night though, I decided to get a little dressed up. I had brought a couple pairs of panties and a bra with me in my suitcase. I had been secretly cross dressing for a few years, but nothing public. Occasionaly though, I would wear something out under my male clothes. That was the idea tonight. The panties were a black g-string and a white silk thong with purple flowers on it. The bra was a padded red one that clasped in the back. I also brought two balloons that I filled with water from the hotel sink, to nice c-cup sized breasts. I slipped on the black g-string and red bra, inserted my balloon breasts, and strutted around the room for a while, stopping occasionally at the bed to get into various poses (doggie style and on my back folded in half were especially favorites).

After about thirty minutes, I was pretty turned on and feeling adventuresome. Having not brought any makeup with me and not being in public before anyway, I knew that I couldn't leave the room with my bra on and breasts in. So I took out my breasts, slipped out of the bra straps, spun the bra around and unhooked it. I threw on some loose fitting jeans over my black g-string and a tight t-shirt and headed downstairs to get something to eat. The Hilton had a few shops, but I just settled for the Pizza Hut pizza combo meal and ate it in the little dining area they have. Afterwards, I grabbed my soda and headed over to the quarter slots to play a few pulls.

I sat down at a machine, put my soda off to the side and started playing. On my first pull, I hit a nice win and got a few more minutes worth of play. With about half my winnings left though, this fairly tall black guy sat down at the machine next to mine. There were sporadic people around, but no one on either side of the two of us.

"Hey there," he said.


"Winning?" he inquired.

"Got a little lucky on my first quarter," I replied.

The he turned to me and said, "that's cool. By the way, I like that sexy g-string you've got on."

I was a little stunned as I reach back behind me to feel that my t-shirt had risen up above the top of my jeans, so indeed my g-string was showing. I tried to play it cool. "My girlfriend likes me to have a reminder of her when I go away."

"Is that so?" he asked me with a sly grin on his mid-thirty year old face. "Tell you what, you buy me a drink and I won't start raising my voice and asking you why you're wearing women's underwear."

"Fine," I said, figuring one drink wasn't that bad a penance to pay for being caught with my fetish.

"Let's head over to the bar," he suggested.

We got up and went over to the bar inside the casino area and grabbed a couple of stools. I ordered a corona and Ray, as he introduced himself on the walk over, got a jack and coke. Ray didn't ask me my name while we were sitting there, but instead told me he was going to call me Karen. He said, "since you insisted on wearing girl clothing, you would get a girl name."

"Great," I answered sarcastcally.

"So, Karen, do you have any more of your girlfriend's clothes on?"

"Nah, just her panties," I said.

"What about in your room, did she give you anything else to remember her by?" he asked.

I hesitated a little, and Ray immediately knew that I did have more items upstairs. "Take me to your room, I want to see your whole slutty outfit she gave you to wear," he insisted.

I'm not sure why I agreed, but we finished our drinks and headed to the elevator for the Central Tower. We got on and moved to the back, then an older couple got in before the doors closed. They pushed the button for the 20th floor, and I asked for the 27th. As the elevator started to move, I felt Ray's hand on my ass, starting to caress me. I just stood there frozen, not knowing what to do as it would have been a little embarassing to make a scene in front of these conservative older folks. He moved his fingers in between my cheeks and rubbed my hole through my g-string and pants while I just stood there. I started to feel my cock growing a little as this taboo scene played out.

"Ding," 20th Floor and the old people exited. The doors closed and Ray spun me around, hand still on my ass, and pulled me against him. He reached down and put his other hand on my open cheek and asked, "Do you like being manhandled, slut?"

Before I could answer, he said "it feels like you do unless that's just a pencil in your pocket." I started to blush in shame and dropped my head so that he couldn't see the look in my eyes.

"Ding" 27th floor. Instead of letting me go, Ray pulled up on my ass cheeks, lifting me off the ground. He was about four inches taller than me, and about fifty pounds heavier, some muscle, some not. I was pretty lean, so it wasn't much of a task for him to get me off the ground. I looked over my shoulder and was relieved that there was no one waiting to get on the elevator.

"Wrap your legs around me slut," he said. I did as I was told, and also put one arm around his shoulders. I used the other hand to get my card key out of my back pocket, struggling a little as it was pinched between my ass and Ray's firm hold. I told him which way to go and which room. When we got to the door, he pressed me up against the wall and leaned into me. I could feel his hard cock against mine, as he used one of his hands to take the key from me and swipe it in the lock. The door clicked and he turned the handle and pushed the door open. He carried me in and sat me down on the dresser that was against the wall, across from the bed. Then he caught me off guard and leaned in and kissed me softly on the lips. I was like a deer in headlights, not knowing what to do. This was my first kiss by a guy and I was pretty taken aback. He just continued kissing me softly, then started to part my lips with his tongue. I opened my mouth and kissed his tongue back. I couldn't believe it, I was french kissing another man. And my cock was getting really hard now through my panties, I was so turned on.

Ray stopped kissing me and pulled away and said, "ok, show me what else you have." I hopped down off the dresser and went over to my bag and uncovered my red bra and balloon breasts. Ray told me to go into the bathroom and put the bra on, breasts in, and to leave all my male clothes off. I was so turned on that I did as instructed. I came back out as Ray set his cell phone on the dressing table next to the bed and turned around to see me in my red bra, black g-string, and 34c breasts.

"Come over here," he ordered. I did as commanded and he embraced me in the usual way, two hands on my ass and now a tongue in my mouth. He picked me up again, but this time instead of heading for the dresser, he took me over to the chair in the corner of the room by the window. He sat us down so I was sitting indian style in his lap, with his hands rubbing my ass, and his tongue darting in and out of my mouth.

"Baby, pull my cock out and stroke it," he ordered. Again, I was totally submissive to his every desire at this point and did as I was told, unzipping his jeans and reaching into the slit of his boxers. What I found confirmed my suspicions from when he pressed up against me in the hall. Ray had a nice big, black cock. It was about eight inches long, but not as wide as I thought it would be. With my right hand, I started to rub up and down the length of the shaft as he started kissing me again. We went on like this for a few more minutes when he stopped and said, "that feels really good slut, but now I want my cock in your mouth. On your knees bitch."

I backed up off him, dropped to my knees like the submissive slut I had become all of a sudden, and took his head into my mouth and started easing his cock in and out of my mouth. Ray just leaned back and relaxed as I began to suck my first dick. I licked circles around his head, then bobbed my head up and down on his pole, managing to get a little more than half into my throat before raising up off him.

"That's not bad slut, but I want to fuck your throat deep. Stand up, go over to the bed, and lay on your back with your head off the edge." I did as I was told and was laying on the bed, with my head basically upside down. I saw Ray come up in front of me and point his dick at my open, waiting mouth. I reached up with my hands to put them against his legs, as he reached down and behind my head for leverage. Ray started taking long deep strokes into my mouth. Each time, pressing deeper into my throat. After about five minutes, I had gotten used to him and relaxed enough so that his cock was going all the way down my throat and his balls were resting on my nose before he would pull out.

"That's a lot better my little cumdumpster. You've got a nice tight virgin throat and I'm enjoying fucking it." I had processed the fact that he called me his cumdumpster and I now knew I was going to be swallowing his load at some point. That point happened to come soon as he started picking up his thrusting speed, slamming his balls into my face faster. Then I heard him groan and felt his head started to grow before tasting a salty liquid as it poured into my mouth and down my throat. There was a lot of it and I tried to keep up, but some escaped and leaked down my cheek, toward my ear. Ray was leaning forward over me now as I kept his head in my mouth, circling it with my tongue, sucking every last drop of his cum like the good little cumdumpster I knew he wanted me to be.

Ray pulled out of my mouth and started rubbing his semi-erect cock across my lips. "You liked sucking that cock, didn't you slut?"

"Uh huh," I replied.

Suddenly, there was a knock at the door. "Good, because I'll have more of that for you during the course of this night," he said as he went over to the door and opened it up. In walked a talk black girl with a big shoulder bag. She walked over to the bed, set her bag down, and sat down as I sat up, a little confused. She leaned in and licked the rest of Ray's cum off my cheek, then kissed me, making sure my tongue went across his seed.

"Looks like the bitch needs some more training," she said. "I'm here to help you honey. My name's Carla, and you can think of me as your new big sister."

Carla got up, and unzipped her bag. "Ok, honey, time to clean up." She handed me a bottle and said I was to go shower and rub the contents all over my body and it would take care of all my nasty body hair. I did as told and came out smooth, like a baby. Carla then came in and pulled out some breast forms for me and glued them on with the special glue that comes with them. She applied some makeup around the edges, so that it was harder to tell they were fake. Then she came in with a new outfit for me. She handed me my black g-string back and gave me a matching lace bra. I was now a 36B though, as she did not want me to be bigger than her. I put them both on and then added the black thigh high stockings she had for me. Then a nice black mini skirt and blue silk short sleeve button up shirt.

Carla gave me a brown wig and then she turned me around to work on my makeup. Ten minutes later and I looked like a younger middle-aged business woman ready for a night on the town. It was amazing how much different I looked. She handed me a pair of two inch heels, figuring this would only make me as tall as her, and help keep me balanced during the night. "Maybe tomorrow you can try the six inch thigh high boots," she joked. I practiced walking around, and also talking in a softer high pitched voice for a while. One and a half hours after sucking my first cock, Ray, Carla and I left my room for a night out.

We headed back to the elevator and then down to the lobby. Ray kept up his usual elevator etiquette, rubbing my ass while we descended. We strolled through the lobby and then back into the bar. Ray excused himself for a minute and left Carla and I alone to chat.

"So, how long will you be staying in Vegas?" she asked.

"Just a few more days," I answered.

"Oh, that's nice. That will give us lots of time to spend together at night," she noted.

The drinks Carla ordered arrived and Carla toasted to swallowing semen. We clinked our glasses and took a sip. We continued talking small talk for about ten more minutes and our drinks were getting low when the bartender came over and handed us two more drinks.

"Compliments of those gentlemen over there," and he pointed to a group of three guys sitting in business suits in a corner of the bar. Carla grabbed my hand and led us over to them. She introduced us as Carla and Karen and the guys pulled up two chairs for us. The guys introduced themselves as Bill, John, and Dave. Bill looked like he was about forty-two, your typical receeding hairline, slightly overweight businessman. John was a little older with some grey in his hair, but he was average height and in pretty good shape. Not too muscular, but lean like a runner. Dave was a petite man, with glasses and the shiny head from going bald. They asked us what we were doing in Vegas and Carla said, "just here for business."

"What business?" Dave asked.

"Well, if you must know," Carla said, "I'm a girl of the night and I'm just trying to break in this new girl. You can tell by her looks and outfit that she's innocent. In fact, she just sucked her first cock about two hours ago."

"Hey, congratulations!" Bill said and put up his hand in the international sign for asking for a high five. I played along and slapped his hand.

"How was it?" John asked.

"It was really nice," I said. "I was able to swallow all eight inches of it down my throat." All three started to give me little clapping, golf claps as they are called. I stood and bowed, but kept my head up and caught Dave from across the table staring right down my shirt. "Yeah," I continued, "and I really liked being on my back while having my mouth fucked." I couldn't believe I was standing in front of three guys I just met, telling them I liked sucking the cock of a strange man.

"Damn girl," said Bill, "you should be in sales because looking at you and listening to you talk, I'm sold. How much does a blowjob run these days?"

I just looked dumbfounded for a second because I honestly had no idea what to say when Carla piped up and said, "fifty."

Bill was mulling it over, then looked over to the other two and they all began to nod in agreement. "Ok, said John, but let's say we're having such a good time and want a little more. How much for that?" Carla didn't even miss a beat and answered, "a hundred."

"Ok, let's go," said Dave. And Carla and the guys got up and everyone finished their drinks. By this time, I had a really nice buzz going, as Carla snuck her arm inside mine so we were walking arm in arm like a couple of old friends. The guys led us to the East Tower elevator and pressed the button for the twenty fifth floor.

"Ding," and we all exited. They led us down the hall and into their room and Carla put her bag on the bedside table and sat down on the bed. I took a seat next to her on the bed.

"Ok, boys, what's your pleasure?" she asked.

The guys all huddled up and then Dave, their spokesman, spoke up. "We all want to fuck Karen's pretty little mouth, but then I want to fuck too."

"Ok, then why don't you go first on Karen, Dave, then you can fuck me while she blows Bill and John at the same time. But first, that will be $250, three blowjobs for $50 each and one fuck at $100." The guys all pulled out there wallets and pooled the cash together while I just sat there in amazement that I was now a Las Vegas cock-sucking prostitute. The scary thing was that I was getting really hot again know I would get more cock in my mouth.

Dave gave Carla the money and then came up and stood right in front of me. I knew the drill and dropped to my knees, undid his pants, pulled them and his tighty whities down and took his cock into my mouth. I put a hand around the base and started circling his head to try and get him hard. That worked as he grew to a decent six inches, and a little skinnier than what I had in my mouth from Ray earlier. I started bobbing up and down, letting his cock slip almost all the way out of my mouth and then forward until I had my mouth against his pubes. They were ticklish against my nose, so I used my index fingers to keep them out of the way while I held his rod and sucked away. I looked up to see Dave with his hands on his hips, staring down at me, enjoying his cock going in and out of my mouth.

"Damn boys, this slut is pretty good at sucking cock. I can't believe today was only her first."

"She got a good first lesson," Carla chimed in as she started to take off her clothes and lay down length wise on the bed. She put out some condoms and told Dave to take his pick when he was ready. Bill and John sat in the office chair and lounge chair with their cocks out, stroking them to the show they were getting. After another few minutes, Dave pulled his cock out of my mouth, slapped me across the face with it a few times, then told me, "that was very good you little cock-sucking whore."

I just smiled and said, "thank you," and stood up and went over to the other two guys. Bill was in the office chair, and it was on wheels, so he wheeled it over next to the lounge chair that John was sitting in. As Bill was still getting positioned, I dropped down in front of John and took him into my mouth. When Bill was in position next to us, I reached over and started to stroke his cock. I tried to time it so that I would switch cocks every minute or so, and that way neither guy would feel neglected. John's cock was amazing. It was nine inches erect and very thick. I got him into my mouth, but had trouble getting him more than half way down. When I switched over to Bill, he was easier in a way. His cock was as long as John's, but much thinner. I was able to deep throat him, although he touched new depths in my throat, although not by much. During my third switch back to John, I peaked over to see Dave banging into Carla from behind. He had a firm grasp on her long black weave and was really laying into her. She sounded like she was enjoying herself as I heard, "yeah baby, that's it, pound my black pussy."

I watched her for another half a minute then went back at Bill. I picked up my pace and was really going to town on his cock when I heard John say, "if I add another hundred, can I nail this slut?"

"Oh my God Baby, well...it's a bad time of the month for her, oh God yes, so for an extra twenty-five, holy shit, you can take her virgin little ass," was her reply. I couldn't believe it either as I saw John get up, take out his wallet, drop the cash on the pile, then turn back toward me with a devlish little grin.

"Baby, there's some lube in my bag," Carla suggested. "And Baby, let the slut do all the work putting you in her. I want to know that she wants it. Just get behind her, lube up, and let her back up into you."

"You got it, but then I get to pound her how I want to," he insisted.

"Oh....yeah....no problem."

Dave was going like a jackhammer now, pounding Carla with long deep strokes. Well, as long as he could manage with his six inches. I had the market cornered on big cocks as I had nine inches in my mouth and about to get another nine in my tight little ass. I saw John standing next to Bill and as I turned my head, licked up and down Bill's cock, and then saw John move in behind me while I still knelt in front of Bill. John got down on his knees and I felt his legs fall inside mine, spreading me a little more. I took my head off Bill's cock for a second, but kept stroking him with my left hand. With my right, I reached back, grabbed John's huge rod and pointed it at my hole. I slid my g-string aside with my index finger, then started to back up onto his shaft. I felt my ass lips start to part slightly, then a little more. I felt John's whole head slip inside me as I went back to sucking Bill's cock. I left my skirt down over my ass, so John could see a little, but not much of where his cock had actually disappeared to. I felt John grab my hips and start to pull me back into him. I slid back on the carpet a little, moving away from Bill and almost letting his head slip out of my mouth.

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bydysfunctionaldreams© 6 comments/ 95115 views/ 28 favorites

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