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The Lap Dancer Ch. 01

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Cross-dresser gives his roommate a lap dance.
1.5k words
4.56
84.5k
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Part 1 of the 3 part series

Updated 10/26/2022
Created 04/09/2008
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"So, what should I wear to a Pimps and Whores party?" I asked Sarah. Sarah was my roommate Jim's girlfriend, and had just told us Jim and myself about the upcoming party.

"It's Pimps and Hos, and you dress up like pimp. Or a ho," Sarah said.

The day of the party arrived, and Jim and Sarah went to Sarah's house to get ready. I got dressed up like a pimp with some old and garish clothes that I had bought at the local used clothing store.

I arrived at the party, and was amazed at the costumes some of the people had. There were guys dressed up in some of the most outrageous 1970s pimp clothing, and most of the women were half naked. A girl walked by me wearing nothing but a thong and pasties on her breasts, her outfit topped off with a pair of high heels and fishnet stockings. Another girl wandered by with a dress so short I could tell that she wasn't wearing any underwear. It was a feast for the eyes, but unfortunately all the women were there with guys. As a single guy, it didn't look like I was going to get lucky tonight.

I saw Sarah and Jim across the room. They were dressed like a pimp and ho, but they put a twist on it. Sarah was dressed as the pimp, wearing a fake moustache and big floppy hat. Jim was dressed as the whore. It made sense, actually, as Jim is only five foot seven, and Sarah is almost six feet tall.

Jim was wearing a long, dark haired wig. He was wearing a ultra-short jean mini-skirt and a halter top. He had on thigh high black stockings and a pair of six inch heels.

I walked up towards them. As I got closer I could see the work that Jim and Sarah had done with Jim's makeup. He had blue eye shadow and lots of rouge, and his lips were painted bright red, making them look larger and fuller. "Dude, did you shape your eyebrows?" I asked. Jim just smiled and nodded.

The party had an open bar, and soon Jim, Sarah and I were getting quite drunk. After a few hours, Sarah started to get very drunk. Jim and Sarah approached me, with Jim holding Sarah up. "Dude, I think I'm going to take Sarah back to the apartment and get her into bed."

I wasn't having any luck finding any single women, and didn't know very many people, so I decided to go back as well to split the cab fare.

We arrived back at the apartment and Jim put Sarah to bed. I put on a pair of shorts and t-shirt and went back into the main room to watch some TV. Jim came out, still dressed in his ho outfit. His heels clacked as he walked across the floor to the kitchen. I was surprised how well he could walk in just high heels. Jim noticed me looking, and said, "these heels sure make my legs look sexy!"

I laughed, and replied, "Oh yeah, and your ass too." Jim wriggled his ass, and then laughed as he walked into the kitchen.

"Do you want a beer?" he called out. I said I did. Jim came out holding two bottles of beer, and handed one to me. "Anything on TV?" he asked.

"No, nothing."

"I'm going to put on some music," Jim said. I flipped off the TV as Jim walked over and turned on the stereo. A slow rock song came on.

"This is real stripper music," I said.

"Yeah, maybe I should give you a lap dance," Jim said, and then started shaking his ass in front of my face. He was laughing and joking around, and I started laughing as well. He moved his ass down until it was hovering over my lap. He exaggeratedly moved his ass around in circles. "Yeah, you like that baby?" He asked.

I laughed. I figured that Jim would move away soon, the joke done. But Jim continued to perform. He started bouncing up and down, his ass landing on my crotch. With the contact of Jim's ass on my groin, I started to feel my cock stir. I moved my hands up and put them on Jim's hips. Jim's exaggerated and joking movements suddenly slowed, and soon he was sensually moving his ass against my crotch. I moaned, and let my hands run up and down the side of Jim's legs.

Jim flipped his head back, exposing his neck. I moved my lips close to his neck, breathing against it. I heard Jim sigh as my hot breath hit his neck. I wanted to kiss his neck, but held off, still not sure if this was a joke or real.

Jim lifted his left hand over his shoulder, reached back and grabbed the back of my head. He stroked my hair. I let my hands wander from the outside of Jim's legs towards his inner thigh, and gently stroked up and down there. Jim continued to grind his ass against my groin, and my cock was soon rock hard. I pressed my hips up against Jim's ass.

Jim stood up, and for a moment I thought that Jim was going to walk away. Perhaps this was a joke that had just gone too far. But Jim didn't walk away. Instead he bent over and pulled up his denim skirt revealing his ass, barely covered with a black thong. He moved his ass slowly in circles, letting me get a good look. I moved my hands to the back of his legs and ran them up until they cupped his butt cheeks. Jim pressed himself back against my hands, and I squeezed his fleshy cheeks.

Jim spread his legs apart, allowing me to run my hand up between them. I felt his hard cock through the fabric of his thong, the material wet from pre-cum. I stroked his cock through the fabric of his underwear. Jim reached back with one of his hands, and started playing with my cock through my shorts.

I grabbed Jim's thong, and pulled it off him. It fell to the floor, and Jim stepped out of it. His bare ass was exposed. It was clean and hairless. I kissed one cheek and then the other. I ran my tongue over Jim's taint and flicked at his balls.

Jim turned around and sat down across from me on the coffee table. He started to stroke himself. I undid my shorts and took my cock out. Jim reached over and ran his hand over the head of my cock. It was wet with pre-cum. Jim mopped up the pre-cum with his fingers, and then put them in his mouth. Jim stood up, turned back around and sat on my lap again. He started to grind, my cock rubbing back and forth against his bare ass. I reached around Jim, and started to stroke his cock.

Jim continued to grind on my lap as I jerked him off. He again threw his head back, and this time I started to kiss and nibble on his neck. Jim again started to stroke my hair. His breathing started to get quicker, and his grinding became faster. Soon he was bouncing up and down on my lap, driving his cock through my fist. His body arched, and streams of cum shot out of his cock and onto his stomach. He relaxed, sitting back down on my lap and slowly grinding my still hard cock. As his breathing slowed, his grinding intensified.

"I want you to come on my ass," Jim said, and then lay out on his belly on the couch. I straddled his legs, and jerked myself off. Jim raised his ass in the air. I stroked furiously, looking at Jim's beautiful hairless butt. I quickly shot my load, my cum landing mostly on Jim's beautiful bubble ass. Jim reached back and massaged the cum into his skin. He ran his fingers through the crack of his ass, using some of my cum as a lubricant to allow him to put a finger in his asshole. He fingered himself for a few seconds, and then got up.

"That was awesome," Jim said. "I can't believe we just did that."

"Yeah. That was sure better than any lap dance I've ever gotten in a strip club."

Jim smiled at me as he pulled down his jean skirtk to cover himself. "You know, I was going to take these clothes back to Sarah's tomorrow, but now I'm thinking that perhaps I'll keep them here. For nights in the future when nothing is on TV. Would you like that?"

I nodded vigorously, "I would like that very much."

"Good. Maybe next time we can get even a little naughtier. At the end there, it sure felt good finger fucking myself. Maybe next time we can see what it feels like to get fucked by something bigger."

I couldn't wait.

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