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Slipping a pillow under her ass -- Hardcore fucking sexstory
#1
Gabrielle couldn't stay mad at herself, she knew this was a world of "What ifs" and "Could have beens." Counting her money for the night and considering what had happened, she guessed there can't be many "What ifs" much bigger than this. She took a sip of her coffee and walked out of the coffee shop into the bitter cold. The cold, is what she should have remembered about the night, but then an odd fate took over.

It was snowing, nothing real heavy, but enough to cover the parked cars and the sidewalks in a light dust of fine powder. Normally that would have been a beautiful scene, but Gabrielle was wearing only a tiny skirt and a short faux fur jacket. Instead of properly covering the street, she would wait until a car slowed and then rush out from an tiny entranceway cut into the building. Her negotiations that night were pert and to the point. She lost a few customers, but she just couldn't keep standing out in the cold making small talk while some stiff tried to talk her into a discount.

It was well into the evening before she finally led a customer up the short set of stairs and opened the door to her room. He seemed to be a nice guy, very quiet, well dressed and pretty good looking. She figured he was married and was simply out looking for some spice. He wanted to do her in the ass, which she normally charged seventy-five for, but she wanted to get out of the cold, so she offered to do it for fifty.

After leading him into the room, she took off her clothes as he undressed and then led him over to the sink where she washed him off. Even though she would make him wear a condom, she still washed him off, just because that's what she did. The man didn't argue, actually he seemed to enjoy her handling him as she soaped up and then rinsed his erection.

She dried him off and led him back near the bed where she carefully rolled the condom up the length of his shaft. She then took her tube of lubricant, oiled him up real good and then squeezed a bit over her finger. Most dirt cowboys like watching her finger her anus, so she kneeled on the bed with her ass in the air and reached around, dipping her finger into her tight asshole. Glancing up as his face she saw him smile and knew he liked the short show.

"Okay baby, how do you want it, doggie style?"

"No, I want to see your face."

Moving onto her back she said, "All right, but just so you know, you can play with my tits, suck them if you want, but no kissing, understand?"

"Sure, I just want to look at you when I do it."

Smiling she scooted to the edge of the bed, slipping a pillow under her ass. "You stand up there like that and it will be real good," she whispered, taking his cock and pulling it toward her.

The man followed her lead, leaning to her slipping his cock between her ass cheeks. Feeling the slight resistance, he leaned his weight and then felt her slowly relax around him. He continued his slow push as she talked to him, "That's it baby, just keep it slow."

Feeling him stop at her sphincter, she closed her eyes relaxing herself and then reached to his hips, encouraging him to continue pushing. Once inside, he quickly withdrew and repeated his slow thrust. Moving faster now, Gabrielle clenched her muscles some, squeezing herself even tighter on his rod. In moments she heard him moan and with one hard thrust, he came.

She recoiled a bit, scooting back just a bit under his savage thrust, but then she stopped and squeezed her muscles a few more times. The man's contented look told her he was finished. During the short scene, he hadn't reached for her breasts or done anything but move himself in and out of her ass and as quick as he was, it turned out to be an easy fifty bucks.

Well, not so easy because the guy reached for his wallet and handed her a hundred dollar bill and then held his hand out looking for change. Just staring at him she said, "You got anything smaller? You're my first tonight and I don't have any change."

"That's all I have, hundreds."

"Shit! You wouldn't happen to want to give a tip would ya?"

"Not fifty dollars," he replied.

"Damn. Look, let's get dressed and we can go downstairs. One of my friends maybe can get me come change."

They quietly dressed and then headed down the short set of stairs into the hotel lobby. Spotting a friend she called out, "Shelby, you got some change?"

"For how much?"

"A hundred," Gabrielle replied.

"Let me see," Shelby said, sitting down on the couch and flopping a wad of cash on the table.

"Come over here baby, while we work this out."

The man sat down on the couch and said, "You know, maybe we won't need to go to all this trouble."

"You have some more money? Some smaller bills?"

"No, but I do have this," he said, holding up a small, scratch off lottery ticket. "I'm usually a pretty lucky guy. If you like, I can give you this."

"Yeah, right," she answered.

"I am very lucky and this has a top prize of a million dollars."

Shelby looked at her friend and said jokingly, "Damn girl, you with the million dollars and you'd be the most expensive piece of ass in modern history."

"You think Willie's gonna let me just take a fucking lottery ticket? Hell, he'll start counting while he breaks my fingers." Looking at her John she said, "You keep the ticket baby, I'll just take the cash."

"Okay," he nodded, sitting back as Shelby pulled out five twenty dollar bills and handed them to Gabrielle.

"You got two tens Shel?"

"That's okay, you can have a ten dollar tip," the man said.

"Ah, a big spender."

"I offered you a chance at a million, that's pretty big."

"Yeah, real big," Gabrielle said with a huff, standing up. She started walking to the door as the man laid the ticket on the table and began to rub it with a coin.

Shelby shouted out, "Hey Gabby, aren't you gonna even look?"

"Hell no, I'm not gonna waste my time," she said, stepping out into the snow.

Though the door she heard Shelby shout, "That's one Gabby, only two more."

She began moving down the outside steps, carefully placing each footstep in the light snow. At the bottom step she faintly heard, "There's two, only one more!"

She carefully stepped onto the sidewalk and headed toward the street corner. She still needed several more tricks to break even tonight.

Suddenly she heard Shelby scream loudly and Gabrielle turned and ran to the building, leaping up the steps and crashing into the building. Her John was slipping the lottery ticket into his wallet, but noticing her, he grabbed the two twenties he got in change from her and handed them to Gabrielle. He then stood up, whispered, "Thank you," and then walked out of the door.

Gabrielle slowly sat down on the couch next to a stunned Shelby. They looked at each other and then together stood up and ran out into the snow. They caught the taillights of the man's car as it turned a corner and drove away.

Shelby looked at Gabrielle and said, "The most expensive piece of ass in history... almost."

Gabrielle just shook her head.
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