tagTranssexuals & CrossdressersPimped Out in Vegas Ch. 02

Pimped Out in Vegas Ch. 02


Carla and I got off the elevator and went back towards the bar of the hotel we were in, the Hilton. I could feel myself walking a little differently, more feminine. Of course, I was dressed the part with my two inch heels, black stockings, mini skirt, g-string, lace bra, and blue silk shirt. On top of my outfit, I had already sucked four cocks and had my ass widened by a nice nine inch rod. I definately felt more like a woman than a man at this point.

Once we got to the hotel bar, we spotted Ray, the guy who caught me wearing my panties and who had taken me to my room, fucked my mouth, and then had Carla dress me up so slutty. Ray was talking to a tall thin guy wearing a cowboy hat, jeans, and button up shirt.

"Hello ladies," Ray said.

"Hi," Carla replied. "Who's your friend?" she asked.

"This is Jimbo. I was just telling him about Karen, our new slut in training here."

"Wow," Jimbo piped up, "I can't believe this girl's actually a dude."

I began to blush because in our last interlude with the three businessmen, I was able to maintain the illusion that I was a woman. But now, this tall middle-aged man knew I was a man in women's clothing.

"So, slut," he went on, "you like cock now, huh?"

"Uh huh," I replied, honestly.

He turned to Ray and nodded and I saw them shake hands. A closer look revealed a wad of cash now in Ray's big paw. Jimbo got up, put an arm around my waist and started to lead me back towards the elevators. I couldn't believe I was heading back into action. In the span of two hours, I had had more cock than some girls get in years. Now, I was going back up to a hotel room to have the fifth cock of the night inside my holes.

"Anything he wants, slut," Ray instructed as we starting walking away.

I played along with Jimbo's lead and put my arm around his waist as well. We looked like a married couple strolling up to our room, his arm around my shoulders, mine around his waist. He was only an inch taller than me with my heels on. We got to the elevator bank and while waiting Jimbo leaned over and kissed me on the lips. I kissed him back, but just innocently as there were people around waiting for the elevator also.

Ding. About six of us filed into the elevator and four floors were selected. Jimbo must have gotten the full story from Ray because he immediately moved his hand down to my ass while we stood in the back of the car. Jimbo's floor was the first selected and we moved off the elevator. He moved his hand back to mine and began to lead me down the hall. It was only a few doors down and he keyed us in.

Inside the room, Jimbo kicked off his boots while I stood there and awaited instructions like the slave he had just purchased. He adjusted himself on the bed so he was propped against all the pillows, sitting up, then put his hands behind his head, and then said, "strip for me, but leave your stockings on."

I set down my purse that had my makeup in it, then started to unbutton my shirt.

"Stop," Jimbo commanded. "Do it sexier, dance for me." He reached over and surveyed the radio then came across a hiphop station with the new FloRida song, low. I started to dance around, swinging my hips for him. I moved my hands up across my fake tits while swaying around, then turned and bent all the way over from the hips so that my black miniskirt came up enough to give Jimbo a nice view of my g-string covered ass.

"That's nice, slut," he said.

I stood back up, came over to the end of the bed and got up on it, on my knees. I started to unbutton my shirt again, then swung around so my back was to him. I started to lift up and down while on my knees, like I was riding an invisible shaft and finished unbuttoning my silky shirt. I slowly pulled one shoulder off and peered over at Jimbo's smiling face. Then I did the other and peered over that shoulder. I let the shirt fall off and then kept simulating riding a cock while I felt up my front until I had one hand on my fake right tit and the other high in the air above me.

At this point, I felt an arm wrap around my waist and Jimbo pulled me back to the pillows as he moved around so he was on top of me and I was on my back. He positioned himself between my legs and then grabbed one to wrap around his waist. I took the initiative and wrapped the other one around too as he leaned down and this time invaded my mouth with his tongue. We french kissed for about five minutes and I wrapped my arms around his neck while he started to feel one of my fake breasts.

I was starting to get really hot and Jimbo rolled us over so I was on top now. I slid down a little and started to kiss his neck, then began to unbutton his shirt. I kissed his upper chest, then spent a minute or so sucking his little nipples. Then I moved down further and unbuckled his pants and unzipped them. In one motion I slid his pants and underwear down to his knees. He lifted up, then back down so I could remove his pants over his feet. I stripped him down to reveal a nice fat eight inch cock.

I immediately went back up and took him into my mouth, keeping my head up to look into Jimbo's eyes while I sucked his cock. I knew I had always liked this when my former girlfriends had done it to me. I did my usual licking of circles, then proceeded to take Jimbo in and out of my hungry mouth.

"I'm a cowboy," he started, "be my cowgirl."

I knew what he wanted, so I got up, turned around and straddled his mid-section. I felt Jimbo tuck the bottom of my miniskirt up into the waist so he could watch his cock disappear into me. I slid my g-string aside for the second time on this night, and guided his saliva-soaked cock inside me. Thank God I had already been fucked earlier because my ass was still pretty loose and Jimbo eased in without much effort. I looked down as I lowered myself onto him and was content when I had slowly gotten him all the way in to the hilt. I then looked up, and noticed I could see myself very clearly in the mirror opposite the bed as I was riding my cowboy.

I brought myself up so two-thirds of Jimbo's cock was out of me, then slowly lowered back down. Then again, and again, and again. I could hear Jimbo mumbling, "that's nice, slut," as I continued my grinding down on him. I started to pick up the pace and really slam my hips back into him, burying his fat cock into my ass. He felt so good and stretched me out more than the businessmen had earlier. I got so horny I started talking dirty to him.

"Oh Baby, your cock is so big inside me. I love it," I said. "Fuck me, Jimbo, fuck me with your fat cock."

Jimbo must have liked that too because he leaned up and wrapped an arm around my waist for the second time. He swung me around so I was on my stomach and started to really pound me from on top. I could feel him pulling so far out that his head was at the edge of my ass, then slam back into me with long deep strokes. He did this for a minute, then started to really jackhammer my ass with faster, smaller thrusts. At this I started talking loudly again.

"Oh yes. Oh God. Fuck me. Pound me hard," I kept saying.

Jimbo just got into it more, laying into me with various rhythms, some faster, some longer and slower. We got to a point where he pulled out then rolled me over and grabbed my legs again. He put his cock back inside my sloppily fucked hole, then wrapped my legs around his waist and fucked me missionary with those long, deep strokes again. He leaned down and started to kiss me again, darting his tongue in and out of my mouth. I felt my feet really pressing into his back on every down thrust, encouraging him to drive his cock deeper and deeper inside me. I reached down and put all my long nailed fingers right on his ass, rested my head on his shoulder while he kissed my neck, and pulled him in further.

At this, he started jackhammering me again. My breathing had really picked up and I was a sweaty mess, as was he. He had both arms wrapped around me, with hands under my armpits and wrapped up to hold my shoulders. He was still kissing my neck and then I felt him surge and explode inside me. His cum pooling deep inside me as he collapsed on top of me. I just held him deep with my hands and legs as he continued to spasm and drain his load in me. We stayed that way for a minute and then he pulled out of my ass and went right into the bathroom to shower.

"Get out, slut," he said to me coldly.

I got off the bed, got dressed, and walked back to the elevators. Jimbo's cum had started to leak out of my ass and started to run down the inside of my leg. I got down to the lobby, then went over to my tower to go get cleaned up in my room. I got to my door, then realized that Ray had my key. He never gave it back. Now the cum was staining my stockings and visible below my skirt. I knocked, hoping he had come upstairs, and to my relief he had.

"Jimbo all satisfied slut?" he asked.

"I think so," I replied.

"Good," he said, "because now I want my turn on that pretty little ass of yours."

With that, he picked me up again and carried me over to the bed. He immediately stuck his tongue back in my mouth and then layed us both down on the bed, length-wise. He moved us up so our heads were by the pillows, then reached down, unzipped his pants, pulled out his cock and pointed his head at my sopping wet asshole.

"Dumb slut," he said. "From now on, insist your Johns use protection." The he guided himself inside me easily. I knew this drill well as I just got fucked this way by Jimbo and Ray wasted no time pounding into my well-greased hole. A few minutes in, he adjusted my legs so that my ankles were over his shoulders and then leaned over the top of me so I was bent in half. This was one of my fantasies and I really started to kiss him passionately. He kept pounding my now elevated asshole and I started to moan like a little school girl as we kept kissing. Ray was merciless, hammering away like a man who had other things to do. I reached down again and put my hands on his muscular ass to help pull him deeper. The minutes went on and on. I could feel Ray's breathing get heavier and mine as well. He also started jackhammering my ass and I told him I was close to cumming. He pounded and pounded and I finally gave in and came right in my g-string. A second later, Ray filled my ass with a second load of cum. He didn't stay in me long though and pulled out and went into the bathroom to clean up.

I just lay on the bed in my girl clothes, spent. I had cum in my panties, two loads in my ass, and had swallowed two loads earlier in the night. Ray was right when he had called me a cumdumpster earlier during my training session. I felt like a slut. Heck, I was a slut. A whore too, as I had fucked for money.

Ray came out of the bathroom and told me to get some rest. Carla was going to come get me tomorrow at the same time. He told me not to bother switching hotels, he knew everyone in town and that I was one of his whores as long as I was here.

I just lay there, legs still spread, cum dripping out of me. By the way I was on display for him, believe me, I knew it.

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