Settling Debts

"God damn it Jay! Where the fuck is my cash man!" Mitchell held Jay by the shoulders so the dining room chair balanced on two legs.

"Shit. Take it easy. It's been two days! Give me till the weekend and if I don't pay you, you can come back and do more of this muscle head shit to me."

Jay felt like he was about half the size of Mitchell. Jay was about 5'8" inches tall and about 140lbs. Mitchell though was at least six foot and two hundred pounds

He also worked out, while Jay was mostly into drinking and not exercising.

"How sweet of you to offer. Dumb ass this isn't fucking charity! Bums like you shouldn't be gambling away five grand in one night if you can't handle your shit. If you don't pay me back this weekend, there won't be any more of this mister nice guy shit," Mitchell said as he thrust the chair backwards and sent Jay tumbling. Mitchell turned and walked out of the apartment. Moments later, Jay's roommate walked in. And Jay had an idea.

Tiffany had gone from frightened little mouse to a courageous lion. They had started rooming together nearly two weeks ago. In those two weeks, Tiffany's attitude had changed so dramatically she laughed at her own past timidness.

But this attitude was understandable though. She had come from an all girls’ high school and had had the same set of friends all through junior high and high school. She had a couple relationships that never went very far, physically or emotionally. Those boys had been around simply for appearances and for social gatherings. Tiffany had always had the desire to fit in with the crowd and be non-confrontational. While this attitude had made her a bit of a pushover, it made her agreeable to the point that most people got along with her.

It was exactly this personality of hers that got her into the situation that she was in. Jay was her new roommate and this made her very uncomfortable at first. They meet through mutual friend and upon a basis of mutual need; she needed a place to live and he needed a roommate. The apartment was close to campus and was rather inexpensive compared to the size and comfort it had. Tiffany thought that the deal would be perfect. On top of all that, Jay was a great looking guy who was one of the nicest and endearing people she had ever met. Things really seemed to be going her way.

The way things seemed to Tiffany was actually the near opposite of reality. Jay was not a nice guy. His wealthy father was renting the plush apartment for him, so he really didn't need the money. What he wanted though, was an impressionable and gullible roommate that he could manipulate to cover his gambling, whoring, and drinking habits. His wealthy parents kept an eye on hi finances, so he had to come up with another way to indulge in his vices. Tiffany's personality and demeanor fit that profile to a 'T'.

Her looks though, were icing on the cake. She was truly delicious in Jay's mind. Tiffany was about five feet, seven inches tall. Her shoulder length blonde hair complimented her plump lips and bright blue eyes. And her body was absolutely delicious; a true hourglass figure at 120 pounds. Her breasts were ample and luscious at a ripe size of 32c. Along with her fabulous rack she had what was known as a 'ghetto ass'. It was hard not too stare at her.

With a roommate like this, Jay couldn't help himself. One night when they were both going to be in for the night, he approached her while she was sitting on the couch watching television. She was in a t-shirt and sweat pants and looked so irresistible. Jay smiled as he anticipated the rest of the evening and the problems of his that he would make disappear in an evening.

"Hey Tiff! How's it going?"

"Oh, same ol' stuff Jay. Just catching up with my television viewing and beer drinking," she said as she sipped some more of her favorite micro-brew.

"Mind if I hang with you tonight?"

"Jay, I practically insist that you stay!" she exclaimed. "We haven't ever been drunk together and it’s about time we were!"

"You know, nothing sounds better than an evening of drinking with you," he said with his most devilish smile. "But my buddy Mitch and I were supposed to hang out. Mind if we have some extra company?"

"Any friend of yours is a friend of mine. The more the merrier!"

It was apparent by her volume and tone of voice that she had been drinking quite a bit. The giggelish tone of voice that she used and the sly smile she wore as she handed Jay a beer directly indicated her state of mind. Jay was actually starting to think she desired to be made a fool of simply because of her annoying voice. Despite her drunken joyousness, her eyes looked distant.

"Are you all right Tiff?" he asked with all the faked concern he could muster.

She looked at him for a second and then at the floor. Something was definitely wrong and Jay smiled as she revealed more and more vulnerability. She slumped over in the couch, putting her head in Jay's lap. With her bent over, he could see the empty case of brew that was down on the floor.

"Oh, Jay! It's just that my life seems to be in a rut. Work and school. School and work. The same old guys and the same old dates. Don't mind me, I am just whining for some excitement." Tiffany slumped into the couch and stared at the television with even less life in her eyes.

"Well, I have always believed that you should take control of your own luck. You need to make your own. If you're in a rut, it's because you haven't done anything exciting for yourself."

She sat there contemplating what Jay had said, as if it were some ancient Eastern philosophy. She seemed to nod to herself in agreement and promptly swallowed the rest of her beer.

"Jay your right. I need to start living my life the way I wan to. No more of this day in day out bullshit! I am going to live a life that makes me happy and will keep me full of memories in old age. And first thing I am going to do is take a vacation away from work and school."

"Well I am going to Vegas this weekend. You know your welcome to join me," Jay said as he secretly steered the evening’s activities.

"That would be so great Jay!” she said as she hoped up onto the couch.

Her plump tits bounced in a way that Jay knew she wasn't wearing a bra. He could almost make out nipples.

"But, Jay I have never been before and I don't know how to gamble."

"Oh, don't worry about it. I'll teach you a few things so you don't get suckered into anything. Wait one second, and I'll grab a deck of cards.

Jay went and pulled out a deck of cards as they both sat down at the living room table. Tiffany sat down on the table and pulled out her purse.

"Jay, I think playing for money will be fun. I want to get the stakes into my head and be able to play without being nervous."

"Are you sure that's what you want to do?"

"Definitely."

Jay and Tiffany played about a dozen or so games of blackjack and were about halfway through their second case of beer. Jay got up to call Mitchell and let him know that he could come by for his payment tonight. Jay told him he would have the cash and maybe a girl lined up to cover the rest of the cash. Mitchell being the type of scum he was, said she better be good or else he would be taking it out on him. Jay, not wanting to get his ass beat, that one way or the other, Mitchell would leave with the five thousand dollars of satisfaction that he was owed.

Soon Tiffany was falling over herself barely able to do the addition necessary to play the game. But Jay had been dealing form the bottom of the deck to her favor, and she was up about five hundred dollars. She started betting bigger hands.

"Damn, lady. Think you got a bank in your pocket? Maybe we ought to cool it down a bit?"

"Fuck you," she said half playfully. "Don't quit now that you’re behind a bit. Here, I'll give you a chance to win some back," and with that she put down her whole stash on the next hand.

She was dealt an Ace and a four.

"Fuck yea, I am going to double down. Hit on both."

"Actually, you bet your whole stack. You can't double since you don't have any more cash,” Jay explained, as he held in his excitement.

"Fuck you know I am good for it."

"Tiffany, you can't do that in Vegas so you can't do that here."

"Well then lend me the money. If we are in Vegas and I get a hand like this, you would lend me the cash right? So just spot me, she said and flashed him a smile. Now that she was being playful and trying to play in his flirtatious side, she deserved to be manipulated back, if only in jay's mind.

"Ok, sure I would lend it to you. But what do I get?"

"I'd pay you back!"

"Oh no. Deals don't work that way. I need something real, some collateral."

"Like what?"

"Like your clothes."

"You want me to strip? Ok, mister, you want to play hardball fine by me. I just hope seeing me in my underwear is worth a grand, cause that’s what this is costing you."

"We'll see," Jay said. He dealt the cards. The first was a seven, taking her to thirteen. After another hit, she busted on a Jack. The next hand received an Ace and a then three, and finally a Queen. Courtesy of Jay's quick hands.

"You loose."

"Okay, well, now I am broke and without clothes. What do you want to do now? Want to play another hand or two," she suggested as she open another bottle of beer. Jay was starting to get a hard on from looking at her fine body, in her near see through panties and bra.

"We can't play another hand until I get my cash that you owe me."

"What? I stripped and handed you my clothes, I don't owe you shit."

"No, you owe me five hundred dollars. Your clothes were collateral, not cash. Besides, I didn't get all your clothes; I just got this shirt and these sweats. I spotted you and now you owe me fair and square"

"Well, I’m broke. You want me to take off the rest of my clothes?" She asked as she reached back, half smiling, to unstrap her bra.

"Well, I do want you to take off your clothes since you still owe them to me. But I think we can find a way for you to repay me," he said and walked over to her. He grabbed her hand and led her into the bedroom. They sat down on his bed, and he removed his shirt. "Go ahead and finish now."

With that, she peeled off her shirt, exposing her bare breasts to Jay. He had sneaked some peeks of her as she walked around the apartment in loose clothes or her robe, but he never would have imagined how nice her tits really were. Shaped perfectly, they had a texture that was as smooth as a fresh coat of paint on a new car.

Placing her hands on her hips she demanded Jay's pants. "Come on. Off with these!"

Jay decided there was no point wasting anymore time. He unbuttoned his pants, pulled off his shirt, and lowered his bowers to the floor. He lifted Tiffany up and set her down in front of him. He grabbed her panties and slid them down to her knees.

" Jay, I don't know if we should do this."

"Don't worry. It'll be okay," he said as he gave her his most reassuring smile. Jay reached forward and began to spread her legs. When she no objections, he spread her smooth pale legs open and over his shoulders

Her cute little pussy was shaved bare. It was smooth and looked like it had never been touched before. Jay could only imagine about how tight her little box would be when he pushed his dick into her.

Jay knew he had passed the point of no return. The smile that was deep inside his brain never made its presence know, lest he alert Tiffany to the satisfaction he was getting just from knowing she was about to be conquered and would soon be sold.

Jay reached forward and guided his cock into her pussy. She had a timid look to her face, but the alcohol combined with Jay's charisma made her smile. She reached up and grabbed his ass as he pushed into her. Her pussy was so wet that the only resistance came from the tightness of her cunt. Jay's cock only got harder when he looked down at her huge tits that were now heaving with beads of sweat all over them. The alcohol and the intense fucking were taking its toll on Tiffany. Pulling her legs even farther apart, Jay thrust his prick deeper into her and began rocking her whole body as he pumped her.

He would have taken his time but her knew that Mitch would be at his apartment soon, and he needed everything to be right for when he got here.

After about five minutes off pumping and squeezing, they both let out a burst of air and pleasure. He came deep inside her and when he pulled his dick out even more dripped down onto her throbbing, wet lips. She let out a deep breath and just laid still. He had taken a lot of both of them, but Tiffany had drank way more and was much smaller than him. It looked like she passed out. Jay had time to wipe himself out and thrown on a robe when the doorbell rang. Mitch was at the door and he wanted to answer it with his cash in hand.

"Hey Mitch, thanks for coming by on such short notice. I got your cash right here," Jay said and realized he was still short on breath.

"Hey your still a grand short. You better not be trying to fuck me," Mitch threatened and stepped closer to Jay.

"No I ain't trying to fuck you. I know I am still short, but you said I had all weekend. I still have two days and I just wanted to give this to you now. I can have the cash for you this Sunday, if you want"

"Of course I want it!"

"Okay, okay, let me finish. I can have the cash for you, or you can get your money tonight in another way," Jay said as he motioned toward the doorway.

"What the hell are you talking about?"

"There's this bitch in that room. You can fuck or something and we'll call it even. She's hot as hell man and ready to fuck."

"You better not be lying to me," and Mitchell turned around and walked into Jay's room. He shut the door and Jay sat alone on the couch.

It had only been about five minutes before Mitchell was yelling for Jay. He had been sitting there, thinking about how clever he was for his night's work. He had made five hundred off Tiffany, fucked her and cleared his debt with Mitchell. Just as he thought things were looking up, Mitchell called again. He was probably going to complain or threaten him with his macho gorilla shit or something, maybe ask to come by again sometime. Jay could never tell if Mitchell was going to thank him or punch him. The door to his room opened with Mitchell standing there completely naked.

"What's up Mitch?" Jay asked trying to act as if it was normal to see his roommate passed out and naked on his bed and his bookie's thug standing naked in his doorway.

"Well, that bitch is hot, but fucking that drunk and passed out slut was not worth a grand. That was maybe five hundred dollars worth of sex. "

"Okay Mitch, that's cool. If you want, I can get you the other five hundred tomorrow or you could come by another night and fuck her again. Maybe she'll be awake. Huh? How about that?"

"Nah, I have a better idea," Mitch said as he grabbed Jay by the arm and flung him onto the bed. His robe flew open and he landed on his back, completely exposed. Mitchell stepped up between Jay's legs and pulled them apart. "Lace your fingers behind your head. Do it now."

"Fuck you Mitch!"

Mitchell brought his knee forward and pressed it against Jay's nut sack. Mitch applied enough pressure to separate them and squeeze his balls against his dick and pelvis.

"Jay, I could just tie you up you skinny ass twerp and fuck you with a tire iron or you can lace you god damn fingers now!"

Jay quickly pulled his hands behind his head and laced his fingers. Mitchell immediately pulled his knee back and eased off on pulling apart jay's legs. For a second Jay thought he was going to loose his nuts to Mitchell's knee and get his legs torn off. Jay breathed a short sigh of relief.

His relief was both premature and without reason,

"That's better you little slut. Now don't you dare move a muscle."

Mitchell smiled as he pulled Jay's legs even farther apart than they were before. Mitchell took his dick and pressed it into Jay's asshole. Jay let out a yelp as he felt himself being stretched and violated. He could feel the head of Mitch's dick thrusting deep inside him. After a few more pumps, Mitchell slid his dick deeper in Jay. Mitch also grabbed Jay's cock and began stroking it. Jay immediately, though unwillingly, became hard as Mitch pumped both his dick and his asshole. Mitchell squeezed and slapped Jay's thighs as he fucked Jay's asshole with more and more glee.

Mitchell began humping more slowly as he started jerking jay off much more quickly. Jay's dick began to hurt as Mitchell pumped faster and faster. He knew that when came he would love it. So much tension had been built in him since Mitchell started ass fucking him.

Mitchell pushed his dick all the way into Jay. His pubic hair tickled a bit against Jay's ass and his balls were lifted up against Mitch's stomach. Mitch stopped thrusting and only applied his weight against Jay. Jay felt like his body was going to break in half. His legs were bent back so far that his knees were against his shoulders. After another minute or so of this pressure and Mitchell stroking his dick, he had an explosive orgasm. Jay’s cum shot up across his own chest and stomach. His dick hurt because Mitchell continued pumping his cock with his hand.

Just as quickly as he came, Mitchell pulled out of his asshole and climbed above Jay. He leaned forward and showed his cock so deep in Jay's mouth that he nearly gagged. After a few thrusts down Jay's throat, Mitch pulled out his dick but held Jay's mouth open. He sprayed cum into Jay's mouth, onto his neck and onto his face. Mitchell stood straight up over Jay, took a breath then knelt down next to Jay. He leaned forward and planted a kiss on Jay's mouth. With His left hand he reached down and smeared Jay's own cum all over his hand. Then Mitch rubbed Jay's sperm into his face mixing it with his own. Then Mitch promptly slapped jay's face hard. He face would be pink and red in a minute.

"Thanks you little slut. Your girl was nice, but you were better. Come and see me again if you ever need cash to cover your dumbass gambling debts. At least now I know how I can collect from you."

Mitch slapped Jay again in the face, then walked over to his clothes on the floor. He picked them up and walked out the room.

Jay was laying still, sore as hell, and after a moment he heard his front door close. His asshole was sore, his dick was sore, and he was covered from the top of his forehead to his balls in cum. He could feel it drying across his body. He felt exhilarated and disgusted simultaneously. He just looked over at Tiffany, who was still passed out. Mitch had apparently cum on her face as some of it was still glistening. He wondered which one of them felt worse.

*****

I had a bunch of fun writing this and I am considering a sequel. I'd love feedback on the direction to take it to or about anything else at all. Thanks!