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Bad Boy Billionaires #3 - The Vegas Shark(2)

By:Ryan Field


Harlan crossed to the bed and pulled the covers off him. Without going into a detailed explanation, he glanced down at Treston through his dark sunglasses and said, "I've got a couple of guys out front. I said I could hook them up with the best tranny sex they've ever had."

"I hate that word," Treston said. "You're supposed to say transgender, or at least cross-dresser. Tranny is offensive."

"Fuck that shit," Harlan said. When he said fuck it sounded like fock. "These dudes want hot tranny ass and I told them you'd take good care of them for the right price."

Treston sat up in bed. He removed the ear plugs and set his phone on the pillow. "Did you lose again? Were you playing cards? Is this why you need money? I'm starting to think you have a gambling problem, Harlan. Maybe we should talk about it." Treston spoke in a soft loving tone. He had been born and raised in Vegas and he'd seen more than his share of addicted gamblers. In most cases they were worse than alcoholics or drug addicts. They would stop at nothing to get their gambling fix.

The rowdy college guys in the living room started to laugh. Harlan spoke over their deep hollow voices and said, "We'll talk later. Right now I need you to get your hot little ass out of bed and give these dudes some great tranny ass."

Treston blinked. "But I'm not a transgender or a cross dresser. I don't even like drag shows all that much." Though he had soft delicate features for a man, and a perfectly smooth body he shaved daily because he stripped in public, he'd never been a sissy boy. He worked out in a small makeshift gym in the back of the strip club almost daily to maintain a tight, toned body, and he hadn't been shortchanged in the penis department either. One of the reasons why men went to see him strip was because he was all man, but with a few exaggerated curves in the right places. The only thing that really set him apart from straight men was that he had blond highlights added to his brown hair about once a month. He thought the bleached highlights made him stand out from the rest of the male strippers at the club-and even that was questionable, because so many straight men he knew were dying their hair nowadays.

"These dudes don't know that," Harlan said. "Go put on the pink thing you wore in those Halloween photos you showed me. The one with the blond wig and the pink high heels. Even I thought you looked hot in it and I'm not even into fucking trannys."

"I wore the showgirl costume as a joke for Halloween one year at the club," Treston said. "The only reason I showed you the photo was for a laugh. The costume's in the back of my closet and it took me a while to get ready that night." Treston hated bad drag, which is why he never did it. He loved it when drag was campy or lifelike, but when it wasn't there was nothing more insulting.

Harlan laughed. "Just put on the costume, the wig, and some lipstick and the high heels. You're pretty enough to pass if you wiggle your ass the right way. These dudes are so fucking wasted they'll never care. They're willing to pay a thousand bucks to take turns on you."




 

 

"Oh, Harlan, I don't know about this. Seriously," Treston said. A thousand dollars was a lot of money. Treston had done worse at the club for less money.

The guys in the living room grew louder. When they started to scream, "We want pussy," in their deep, slurred, young male voices, Harlan climbed onto the bed, put his arms around Treston, and said, "If I you do this for me, we can pay off that credit card bill and get a couple of wedding rings and make it official. You know how much I want you to be my husband."

In the short time Treston had known Harlan he'd allowed Harlan to use his only credit card with the fifteen-hundred-dollar credit limit. The last time Treston tried to use the card he found out Harlan had maxed it out. But he loved his man so much he was willing to do anything for him. "Are you serious about this? We'll get rings and get married if I do this for you?"

"Sure I am, bitch," Harlan said. He reached between Treston's legs and found one of his extremely sensitive spots. He rubbed it gently with his thick, rough fingers and said, "You give these guys the best tranny ass they've ever had and I'll marry you this week."

Chapter Two

Harlan had been right about the three college guys being drunk. By the time Treston had put on his sexy Vegas showgirl costume with the pink high heels and entered the living room, all three were slumped back on his old brown sofa with their heads tilted, their eyes glazed, and their mouths half open.

Though Harlan hadn't had much time to put on the costume, he'd done his best with bright red lipstick and big fake breasts and the three guys sat up at the same time and gaped at him for a moment. One didn't even seem to realize he'd licked his lip. The pink outfit had a fluffy showgirl dress that stopped just above his knees, but with a tight sequined corset that pushed the fake breasts forward and cinched his thin waist.

Harlan put his arm around Treston and said, "Didn't I tell you she was fucking hot, guys?" He reached down and pulled up the pink sequined dress and said, "Look at those fucking legs."

Although they were nice-looking young men, Treston noticed there was nothing to really set them apart from a million other young men in college walking up and down the Vegas strip all year long. They all wore the typical tourist outfits: long baggy shorts that hung on their slim hips, loose T-shirts with trite sayings, and well-worn sandals curled at the heel and the toe. They all had thick necks and hairy legs and Treston had a feeling they all played some kind of sport in school. They didn't have the studious look some college guys had. These three looked more like they belonged to a fraternity that cared more about football and beer than math and chemistry. 

While the guys sat there gaping at Treston, Harlan patted his ass and said, "Turn around, bend over a little, and lift up your dress for the guys, baby."

When Harlan said this, Treston noticed the guy with dark black hair in the middle bite his bottom lip. The guy next to him took a quick breath and made a fist. As Treston turned, bent over, and lifted the dress up above his waist, the room went so silent he swore he could hear them breathing. He was wearing a pink lace thong under the dress, the same one he'd worn the last time on Halloween. Harlan leaned over and whispered into his ear. "This is good, baby. You should see their faces right now. This is the fastest buck we'll ever make. By this time next week you'll be a married little fag, with rings and all." Then he reached around and slapped Treston's ass in front of the guys.

Treston looked up at him and smiled. He was still wearing the dark glasses and Treston wished he'd remove them so he could look into his eyes. He stood up slowly and the pink dress fell down to his knees. He set his palm on Harlan's chest and said, "I love you so much."

"Yeah, me, too," Harlan said. Then he slapped Treston on the ass again and pointed to the sofa. "Now be a good little fag, get the fuck over there, sit on their laps, and do what you do best with that ass."

When Treston reached the sofa, the guy with the dark black hair pulled down his zipper and pulled out his erection. He spread his dark hairy legs wider, grabbed it at the bottom of the shaft, and shook it a few times. Treston slowly went down to his knees in front of him. He crawled between his legs, reached up so he could run his hands up under his baggy shorts, and licked his bright red lips in an overly seductive way. They guy released his dick and reached for Treston's head. He grabbed both sides of the blond wig, pulled Treston's face between his legs, and bucked his hips forward. While the other two guys watched and Harlan stood in the background, Treston opened his mouth and took the guy into his mouth in such a gentle easy way the guy's legs shuddered for a second.

Although Treston felt awkward about dressing up as a woman because it wasn't something he liked doing, he couldn't deny he disliked being with these three strange young men in spite of the unusual circumstances that had led him there. Treston didn't need more than one man in his life to keep him happy, but he liked men and he'd always been good at knowing what they wanted most. These three young guys were awkward and not very experienced, but there was nothing crude or vulgar about them. Even though he could smell the alcohol each time they exhaled, none of them was a mean rowdy drunk. He had a feeling they all came from good middle-class homes, with moms who did their laundry, girlfriends who baked them cookies, and sisters who offered them advice on women.

They took turns, holding Treston's head gently and sliding in and out of his mouth as if they were afraid to really let go. They were well groomed and smelled like clean young men should smell. He secretly enjoyed pulling down their pants and removing their sandals. He'd always been attracted to men with hairy legs. He even smiled when one of them reached down to squeeze his fake breasts as if they were real.

As Treston could have predicted, the entire scene didn't last longer than an hour. After he pulled down their pants and removed their sandals, he took turns between their legs with his mouth and his hands, bringing them all to the edge relatively fast. At first he thought he would suck them all off and that would be the end of it. But the guy in the middle, with the darkest black hair and the thickest dick, grabbed the back of his neck and held his head still. He glanced down at him and said, "Get up now and sit on my lap." Then he waved a condom he must have pulled out of his shorts before Treston had pulled them off.