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Bobby Pin

Hugh was in terrible mood. He had been in meetings all week with Asian East Financial. They were planning a stock merger that focused on the importing and exporting of soybeans. Even though it was field stock, not speculative like the projects with which he usually worked, as Chief Liaison Officer for mergers and acquisitions, Hugh was responsible for spearheading the deal and working out the details. Before Christmas, he had spent a solid month in Tokyo at AEF’s Soft Sales Division defining goals and targeting issues with Yoshi Toriyama and his procurement staff. That had been seven months ago and today, they had finally signed all the contracts.

It had been a long complicated process. It always was with international deals, but this one had been particularly difficult since it involved risk management for a product unfamiliar to Hugh. He pulled his Beemer into Leather and Lace. It was a little past six. He really should have gone straight home. Eloise was having one of her infamous July 4th parties and they were expecting a large crowd. He dreaded it. It was part of the reason he was in such a crappy place. He didn’t feel like dealing with his wife’s artsy fartsy friends, listening to them talk about Sean Penn’s artistic integrity or what makes crème boule classic and what doesn’t. Still, Eloise had put forth a lot of effort and money, HIS money, but he deserved a few shots of Buffalo Trace and if he was lucky, Holly Go would be dancing and he’d find some release in one of her sexy lap dances. She was worth the fifty she commanded. If she would let him suck her breasts, which she sometimes did when the bouncers weren’t looking, he’d tip her another fifty. The dark room of Leather and Lace was smoky and inviting. It matched his mood.

“What’ll it be Hugh?” asked Shotgun, the bartender. “You want your usual?”

“Yeah, make it a double, will ya?” said Hugh. “Is Holly working?”

“No, they’ve got a new girl, a real hottie. You might cum just looking at her body. You’ll definitely get a woody.”

“That good, huh?”

“Unbelievable! The rumor is she’s a CWAD.”

“What the fuck’s a CWAD?”

“You know, a chick with a dick.”

“Fuck. Are you serious? This place going homo?”

“No fucking way Man. She considers herself a chick and looking at her gorgeous tits you won’t be thinking otherwise. I’d fuck her if I had the chance, but she won’t even look at me. She likes ‘em rich, a hell of lot richer than me.”

“How do you fuck a chick with a dick?” Hugh took a big swig of his drink. The bourbon felt like liquid steam going down his throat.

“Up the ass Hugh! Something my girlfriend sure as fuck won’t do. Been begging her for months.”

“Not many women will do that. My wife let me once, but she said it hurt like a motherfucker and she wouldn’t ever do it again. She made me stop before I came. I’m not a fag or anything, but I loved how tight it felt on my cock. Nothing turns me on more than a woman’s beautiful ass.”

The conversation segued into boy talk, dirty sex talk, what they had done, what they wanted to do, what they would do if they weren’t stymied by uptight frigid wives and girlfriends. For a brief moment, Leather and Lace was transformed into a high school locker room after football practice.

“That’s her,” said Shotgun drying a beer mug.

Hugh didn’t hear him.

“Hugh, look. Here she comes. That’s Bobby Pin.”

“Hello. I’d like a vodka martini with a dash of cherry juice?” she said to Shotgun. It was not a request. It was clear this was a woman who was used to having people pay attention to her.

“Coming right up, ” said Shotgun. “You getting ready to start?”

“In about five minutes. Please make it top shelf vodka. That other stuff gives me a dreadful headache.”

“Grey Goose okay?”

Bobby Pin nodded to Shotgun and stared at Hugh.

“And who is this fine creature?” she asked extending her slender arm and turning her hand so Hugh could kiss it.

Hugh thought she was one of the most beautiful women he’d ever seen. He could hardly speak. He kissed her hand. She had a perfect hourglass figure, large breast and a gorgeous ass.

“Hugh Cullen, Bobby Pin, Bobby Pin, Hugh Cullen. Hugh is one of our regulars, Bobby, though we haven’t seen much of you lately Hugh.”

“I was in London and Tokyo. I had a big deal on the table. We wrapped up today.” said Hugh.

“What do you do Mr. Cullen?” asked Bobby.

Hugh told her a little about his job, enough for her to know that he had plenty of money. He could practically see Bobby Pin’s mind going ka-ching-ching. He didn’t care. Some women were worth a lot of money. She was obviously one of them. The bar was filled to capacity now. Hugh hadn’t noticed all the people coming in crowding the front of the stage.

“Well, Mr. Cullen. It was nice to meet you. I hope you’ll stay for my show and if you’re still here when I get through, perhaps we can have a drink together.”

She stood up to leave and gently squeezed Hugh’s arm.

“Shotgun, see if you can track down Calvin? I’m not about to go out there without some protection from those wolves up front.”

“I’ll get him, Bobby.”

“Tell him not to forget his taser, looks like he might need it.”

Hugh made a beeline to the john to call Eloise and tell her he would not be able to make their party.

“I’m sorry Sweetheart. There’s been a glitch. I’ll be here with Toriyama all night. No, no, no, enjoy yourself. I’ll sleep in my office and take a shower at Gold’s. I’ve got a change of clothes there in my locker. Okay. See you tomorrow.”

He didn’t know if anything was going to happen, but just thinking of the possibility made his cock feel like a pulsating brick.

“Hit me again Shotgun.”

Bobby Pin was up on stage now dancing seductively around a pole. Hugh thought again how astonishingly beautiful she was. She looked like a cross between Shania Twain and Angelina Jolie. He shook his head and looked at Shotgun.

“I don’t have any interest in her cock, but I tell you one thing, she’s got one of the most gorgeous asses I’ve ever seen. I wouldn’t mind having a piece of that.”

“Oh, you can Hugh. I saw how she was looking at you. It’ll cost you though.”

“And I’d pay it, I’d pay a fortune.”

Bobby Pin was singing Steam Heat. The men up front were going wild, screaming and throwing twenties on the stage. One tried to stick a bill down Bobby’s leather chaps. Calvin grabbed him back and screamed to the crowd, that they could look all they wanted to but there was no touching allowed.

“Do those guys know?” Hugh asked Shotgun. “Do they know she’s got a dick?”

“No Man, they don’t have a clue.”

Bobby had removed her see through top and was twirling her black lace bra on her fingers. A group of men in the front were jumping up, trying to catch it like it was a basketball. The music swelled. Bobby turned her back to the audience and ripped the seat off her leather chaps and shook her ass to the closing strains:

I've got ::cling cling:: fsssss steam heat.
I've got ::cling cling:: fsssss steam heat.
I've got ::cling cling:: fsssss steam heat.
But I need your love to keep away the cold.

Hugh’s cock was throbbing, looking at her round plush fuckable bottom. If he did get a chance to fuck her, he was going to ask her to let him do it with her wearing the chaps. Jesus, he could almost feel her fleshy cheeks in his hands, he imagined what her hole looked like. Another act named Stella Blue followed Bobby, but Hugh had no interest in her.

After about fifteen minutes, Bobby Pin pushed her way through the crowd towards Hugh. Men were groping at her. She smiled serenely and kept going. She had her sights on Hugh. He had figured that out from the way she looked at him and from her body language. She finally reached the bar.

“Great number,” said Shotgun reaching for the cherry juice to make her a martini.

“Thanks,” said Bobby looking at Hugh. “What did you think of my act Mr. Cullen?”

“I loved it. Unbelievable. You’re very sexy. Call me Hugh, will you?”

“No, I don’t think I will. I like the way Mr. Cullen sounds.”

“Okay, whatever rocks your world.”

“There are very few things that truly rock my world Mr. Cullen.”

She stretched out her long slender arm and placed her manicured hand on top of his.
Hugh was surprised at how soft and supple her hand felt. It was so easy to forget – so fucking impossible to believe that she was a man. Her fingernails were long and cherry red like the juice Shotgun was pouring in her martini glass.

“Me too. I don’t trust people who get turned on by everything. I’m rather selective myself.”

Bobby Pin squeezed Hugh’s hand and gently placed it on her rump. It felt exactly like he thought it would, round and firm but voluptuous as hell. Hugh was glad he was sitting down since his cock felt like a lightening bolt. Bobby Pin looked down at his lap.

“How about this Mr. Cullen. Is this something that would rock your world?”

Hugh pressed firmly on her ass cheek and dug his fingers into suede patch that snapped onto her chaps.

“You have no fucking idea.”

“Oh, I think I do Mr. Cullen. Is it something you’d like to explore?”

“I’d give anything to explore it.”

“That’s good, cause it won’t be cheap.”

“It doesn’t matter. I’ll pay whatever you want. I’ll give you whatever you want.”

“God, I love men like you, strong men who know what they want and how to get it. You know about me right?”

“I know. I don’t want anything to do with the front.”

“That’s fine Mr. Cullen. I kind of suspected that. I tell you what I’ll take care of your front side and you can take care of my backside.”

“Sounds good to me.”

“Okay, shall we go? I have a suite at Regal Oaks downtown. We can go there and have a drink in my room. I have to be back here by midnight. That gives us a couple of hours.”

Bobby Pin slid her key card and the door clicked open. It was a big room; it was actually two rooms, a bedroom and a foyer area with a couch and a refrigerator and a little bar area that appeared to be fully stocked with top notch liquor.

“What can I get you Mr. Cullen or would you prefer it to be bartender’s choice?”

“Bartender’s choice.”

Hugh sat down on the sofa. His cock was aching. He’d had a steady hard-on for almost two hours, a hard-on that grew whenever he looked at Bobby Pin’s chaps and the shiny silver snaps that kept her ass patch in place. He couldn’t wait to rip that off.

“We’ll handle the financial details later. There’s something about you I trust and there’s definitely one thing about you I like,” said Bobby Pin as she cupped Hugh’s throbbing cock in her hand.

She had made him a double scotch with a dash of seltzer and few drops of ginger. It felt like fire in his throat and the ginger tickled the back of his tongue. He imagined she had done this on purpose.

“Ever done this Mr. Cullen?”

“No, I haven’t.”

“Never done it with a woman either?”

“Not really. My wife won’t go there. I tried once with a prostitute in Bangkok, but to be honest she turned me off. She wasn’t that appealing.”

“Do you find me appealing?”

“I wouldn’t be here if I didn’t.”

“Well, I don’t think you need an instruction manual. The only thing you need to know is you’ll, well we’ll both be needing this,” she said holding up a tube of Anal Eze. “Just make sure your cock and my ass have plenty of it. It’s probably best to start with your hands, just pretend like you’re finger painting and this is your paint.”

Listening to her talk about it in such a matter of fact way made Hugh wild with desire. His cock needed relief; his hard-on was painful. He downed his drink and grabbed Bobby Pin roughly by the hand and laid her across his lap. She did not resist. Hugh thought she was probably an expert at this. He massaged her ass through the patch. The suede on Bobby’s bare ass made his feel chafed, almost as if he was being spanked. Slowly, at least with the first few, Hugh unsnapped her patch, and then he got more excited and ripped it off with one violent tug. Jesus fucking Christ, her ass was beautiful, creamy and plump. Her skin felt tender. He had no urge to whip her though he could understand how easy it would be to get off on that. He spread her cheeks apart. She was completely hairless and her hole looked too tiny to take his huge cock, it wasn’t much bigger than his thumb. He picked up the Anal Eze and opened the tube and squirted it into her hole until it overflowed and ran down her crack. His hands were covered in the gooey gel, so he began to finger her hole, slowly at first with just one finger, then two and then three and then he bent his knuckles to open her up more.

“You might be a virgin, but you know what you’re doing,” said Bobby Pin.

Hugh thought she looked like the best erotic fantasy he’d ever imagined, in her leather chaps open at the ass. He thought he had fingered her enough. He was going to take her now and fuck her as hard as he wanted. He guessed she would stop him if it was too much.

“Lay over the end of the arm of the sofa. I want that fine ass propped up in the air where I can get to it.”

Bobby Pin did as he ordered.

“Don’t you want me to suck you Mr. Cullen? Most men want that. I’m very good at it.”

“No, I don’t want that right now. Maybe later. Get it up there,” said Hugh eyeing a bench by the bar. It looked like a picnic table bench but it was covered in black vinyl like a weight machine.

“Wait a minute,” said Hugh getting up and going over to the bar. He brought the bench back with him. “Lay on this and wrap your legs and arms around it like a tree.”

He could really get to her now. He squished some more lube into her hole and greased up his cock, which by now was like a steel pole. He put the head on the rim of her ass. Fuck, she felt good, soft and pliable, but firm. Using both hands, he spread her ass apart so he could watch his cock enter her hole. It took a little effort because he was so turned on and his cock was so engorged. It was like sticking his dick into a sucking cantaloupe. The more he pounded her, the more her ass closed up around him and gripped his cock. He braced himself by holding on to the sides of the bench and started fucking her. He fucked her hard and fast like an animal. With every thrust, he thought he was going to explode a sea of cum into her asshole. He slowed to a steady rhythm to make it last a little longer, but it was no use. Finally, he let himself go and pounded his cock into her like a jackhammer. Bobby Pin was moaning softly, clenching the carpet with her fists, but she was taking it. Hugh thought she was taking it like, well like a man. When he came, it was like a geyser of cock juice. Hugh imagined it filling her up and spilling over and out of her like a frothy beer.

After he had caught his breath, Hugh went to the bathroom and came back with a warm cloth. He tenderly cleaned her up and then led her back to the couch where he held her in his arms.

“So how much do you charge for your time.”

“Per hour or per day?”

“I’d like to know your per day charge plus any per diems you usually add to it.”

“I charge a thousand per day. I don’t do per diems.”

“No shopping extravaganzas for you huh?”

“No, it’s just that if someone wants me for the day, they usually keep me with them as an escort and then later for the sex part. Why what did you have in mind Mr. Cullen?”

“I was just thinking about some Japanese gardens I saw in Tokyo.”

“I’ve never been there. Always wanted to, just never had the opportunity,” said Bobby.

Hugh put his hand under her ass.

“Got a passport?” he asked.

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