Betting It All free porn video

The game blared on, and the Bills were losing again. Donnie sat there looking at the screen in satisfaction.

"Looks like you will be doing the dishes for a couple more days again, Keri. You gotta stop betting if you want to keep any of your free time." Donnie's younger brother laughed. Darrin was a good kid, barely turned 17 a month ago, but still, he was tolerable, Keri had decided. And he had even stopped trying to get a peek at her when she was showering, or in the hallway to her room before or after her daily rituals.

Keri was renting a room from Donnie while she attended the local college where she was working on her degree. Donnie owned the house outright, the result of some money he had inherited from a great uncle somewhere. He was a nice enough guy. At 26, he was the oldest of the three, by far. Keri came in at just 20.

Darrin rounded out the occupants of the house, having moved in with his older brother while their parents went through a nasty divorce. He had applied to get emancipated as an adult, but that had been shot down because he had no visible means to support himself. Then Donnie stepped in and offered to take him in while their parents engaged in their mutual bloodbath. He was more withdrawn because of what had been happening with his family, but in the four months since she had moved into the spare bedroom, he had slowly opened up to her. She was a real live girl, and the attraction of proximity he felt for her was in evidence almost from day one.

The bets were always the same. Since she didn't have any money as a starving college student, she bet her labor against Donnie's money, any of which went to her rent payments by mutual agreement. It was a situation which had worked out in her favor a few times, and she was happy to work for the rent.

Any extra money was needed to save up for a car, so she didn't have to take the local bus system to her classes. It was a forty-five minute bus ride, but by car it was less than fifteen. Plus, she would be able to run her own errands, such as any shopping she needed to do, or any trips that were outside the regular bus schedule. As it was, she had worked out an agreement with Donnie to coordinate her travel needs with Donnie, so that she could get done what she needed to accomplish, like medical appointments and the like.

Now she just nodded. "The Bills suck. I was really hoping this time that they might pull things together, but it wasn't in the cards. Maybe next week."

Darrin spoke up, one of the rare occasions for him. "Do you think the Cavaliers have a chance against the Lakers tonight?"

"Nope. Since Lebron 'took his talents to South Beach', the Cavs truly suck. Koby and his crew will totally kick their asses. It's almost a forgone conclusion. Even the Vegas odds makers seem to think it will be a major blow out."

Donnie thought about it for a moment, and an idea germinated in the back of his brain as he looked sideways at the girl renting his room. He had always been the perfect gentleman to her, and while she'd obviously had some fears when she moved in, those had subsided as they had gotten to know each other. Donnie was a gentleman on the outside, but inside, the thought of his renter's lean, athletic form had been the fodder for a couple of masturbation fantasies in the time since he had caught an illicit glimpse of her butt on her way back to her room one evening.

At the time he was certain she didn't know what he'd seen, as the towel had ridden up quite a ways on one side, exposing that entire cheek, most of the crack in the middle, and a small portion of the cheek on the other side. Later, she'd asked him if he had noticed, and he had nodded and apologized. She'd been mortified, but they'd gotten over it.

Keri, for her part, had been secretly thrilled by the unintended exposure, even while she'd been embarrassed by it more than any other event in her life. But Donnie was a good sort, and had never once made an illicit pass at her. He'd offered to take her out to dinner and a movie on a date, but she'd turned him down. Neither had steady relationships with anyone else, but she wanted to keep the relationship as professional as possible. It just seemed like a good idea to keep her situation as uncomplicated as possible.

Now she finished her soda and went for another in the kitchen, intent on drowning her sorrows from the loss of her favorite NFL team in a haze of sugar. She returned to the couch and popped the top, and Donnie decided to see if his roomie was up to a much greater challenge.

"I think you should put your ass where your mouth is on the Cavaliers tonight. What do you say?" It was the same phrase he'd used every other time before, so she knew what was going to happen next, or so she thought.

"Yeah? What's the wager this time? More dishes? Shoveling the snow? Laundry? Not much else left to do around here." She took a sip from her new drink, and looked over at him intently. She was a highly competitive person by nature, with a drive to succeed that had gotten her a partial academic scholarship to the local college. She just couldn't turn down a chance to bet, when there wasn't any of her money on the line. She simply didn't have any to bet, and every dime was precious.

"Hmmm. How about something completely different this time?" He said it as if it were no big deal, but inside his heart was pounding hard. Maybe he'd had way too much to drink to be contemplating this. But, in for a penny, in for a dollar, or whatever that phrase was.

"How different?" She seemed interested. That was a good sign.

"Well, how much do you need to fill your car fund?"

"Hah. Right. No way are you going to bet me two thousand dollars. There is nothing I can do around here worth that kind of money. Besides, it will just go towards two rent payments. I have to buy books soon, so I would only be able to put about thirteen hundred into the car fund."

"That still would make a huge dent in your car fund, right?"

"Yeah, but what's the wager? What would I be doing if I lost?" She was seriously thinking that she would do it, no matter what it was. She had not confided in Donnie, but her financial situation was getting really dire. Without a car to be able to find a job other than retail, she wasn't sure she would be able to continue in college. Retail didn't pay worth crap. It was almost a break-even point, given how little time she had to be able to work while still keeping up her studying, and how much mass transit cost.

"If the Lakers win, I pay you two thousand dollars. If the Cavs win, I watch you have anal sex with Darrin." He was surprised that it came out as level as it did. His voice broke twice after 'sex' and 'Darrin'.

Keri was certain that she hadn't heard that right. She was glad she wasn't. "What the fuck did you just say?"

Darrin stared at his older brother, a rock-hard erection suddenly in evidence in his sweat pants and a rushing sound in his ears. Keri was right. What the FUCK did Donnie just say? Had he heard that correctly? 'Oh my fucking God! Fuck Keri in her ass? YES, PLEASE! OH GOD, YES PLEASE!'

Donnie tried to speak once more, but it only came out as a squeak, followed by a slight cough. He cleared his throat, and tried again.

"If the Lakers win, I pay you two thousand dollars. If the Cavs win, I watch you have anal sex with my little brother, Darrin." He got it out that time.

"Are you out of your fucking mind? No way!" She said it with a little emphasis, but inside she was thinking furiously about it. She had no intention of having anal sex with anyone, let alone Darrin. He was cute, and a buff high-school athlete at that, but no one had ever been where the sun didn't shine with her. But, two thousand dollars was a lot of...

"Five thousand."

The blood drained from her face. That would pay off the rest of her rent through the end of her lease, and leave her some left over. She seriously considered it. The difference in her financial situation would be night and day. Then she thought about what she would have to do if she lost. She glanced over at Darrin, and did a double-take.

Darrin was staring at her open-mouthed, with a vacant look in his eyes that was almost frightening. Then she looked down and had to fight an almost impossible battle against smiling. He obviously liked the idea of the bet, with that huge boner sticking up in his sweats.

She turned away, looking out the window while she took another pull on her soda. Was she really thinking about doing this? No. No way. But ... five thousand ... no. No way in hell. She'd only had sex three times, in spite of having had a regular boyfriend all through high school. She'd given him oral sex a lot of times, keeping him happy. She'd even learned to tolerate swallowing. It was just practical after the first time she'd done it, when his semen had gotten all over her favorite Islanders jersey, and had basically wrecked it. It wasn't all that bad.

But allowing someone up her ass? No way.

"I've never done that before. I've heard it really hurts, and I have no interest in finding out if that's true."

Donnie smiled gently. "I can teach you how to do it so you will have a bare minimum of pain, if any, and you will really enjoy it. There is definitely a right way, and a wrong way. I guarantee you will have a good time, or I will pay you half the money anyways."

"No video or pictures. You can't tell anyone, and no bringing it up with me again. This would change nothing about our situation here." She couldn't believe she was negotiating on this. What was she thinking?

"I can live with that. Do we have a bet? Either way, you win."

Keri thought about it. No, this was not happening.

"No way. I can't do that. I just can't." Darrin looked incredibly disappointed as he got up and left the room, the tent in his sweats leading the way even as he tried to walk with his back to her the entire time. He ran up to his room and closed the door, no doubt to rub one out, she thought to herself.

"That's fine. If you change your mind, we can still do the same wager on something else later."

A week went by, and the following Saturday found them once again on the couch, watching sports. Donnie was happy that his indecent proposal hadn't seemed to change the dynamic in the house. After he sobered up, he had been worried about how Keri would respond. She was a very nice girl, with an incredible 5' 2" build that was simply poetry in motion when she walked. Years of track, swimming, and weight lifting had sculpted the girl into a beauty that Playboy would have paid millions to photograph, if they'd known she was out there. It was a good idea, even if it had been blown down in flames.

He glanced over at her once more, and sighed internally. She had told him once that she was the product of a mother from India and a father from Egypt, which gave her a natural, gentle tan, and large, dark brown eyes, under lustrous black hair that fell straight down to her low back. She normally wore it with scrunchies to keep it under control, which, along with the solid white tee shirts and nice blue denim jeans she wore made her incredibly attractive. Her coloring was darker but similar to Darrin's, who was part Latino and part French, as was Donnie.

"What are you looking at?" She shot at Donnie in jest, a continuation of the verbal jousting they had been engaging in since a couple weeks after she had moved in. It was nice to find someone who shared her personality, she thought. Even that bet proposal had been something she had been compatible in a general sort of way. High stakes, high reward. The only problem was, the stakes were too high for her. There was no way she would let Darrin in her ass. It would hurt like hell. That wasn't her idea of fun.

Then she remembered his promise that he would teach her how to do it without pain, or he would pay her half anyways. She was so tempted to do it. The money would, either way, help her out in a major way. God, what a decision. She'd thought of little else when she was alone. That night, she'd taken a shower and rubbed herself to climax.

The sexual nature of the bet had been stimulating in and of itself. She'd even played with her ass a little bit while still in the shower, and it had been surprisingly pleasurable. That wasn't something she had ever considered before. It had always been a sensitive area, but she had never equated that sensitivity with any kind of sexual stimulation. Now, every time she took a shower, she rubbed that area at the same time she rubbed herself in front, even using soap to make it slippery once or twice, which had added a new level of sensation and stimulation to her climax.

Donnie had decided early on that Keri was a really nice girl, and he wanted to do what he could to help her out with her finances. That had been the driving force behind all the bets he had been making with her. This latest one, though, had been probably completely wrong. He had no idea why he'd ever thought she would go along with it. Afterwards, he had regretted bringing it up at all. It was stupid. He was such a pervert. Well, he knew he was. He just didn't want anyone else to know. That ship had sailed, however.

"Hey, Boston is travelling to Minnesota tonight. Do you think the Bruins will win?"

"I think they will kill Minnesota. The Wild just aren't that good right now, and they are on a five game losing streak at home, with no signs of it turning around. Their goal tending sucks, and they have too many out with injuries. They don't have a chance. The Bruins are going to the post season. The Wild couldn't stop a troop of Cub Scouts right now."

"Wanna place a wager on it?" The words came out in a perfectly normal tone of voice. He had forgotten the bet from last week. It was never going to happen.

"Sure. Whoever has more goals, including any shootout, wins. Tie means all bets are off." She turned to him with a half-smile on her face.

"That works. What stakes? Laundry? Dishes? Laundry and dishes on your side? A hundred bucks on mine?" He proposed it with his usual radio disk jockey's voice he reserved for moments like this.

She paused for a moment. Then she blurted it out before she could stop herself just as he was taking a pull of his beer.

"What about those stakes from last weekend?"

He coughed suddenly, and sprayed beer out of his mouth and nose onto the hardwood floors and down his clothing. He kept coughing, trying to clear his windpipe, even as he stood up and ran for the kitchen to get some paper towels and the kitchen garbage can from under the sink to clean up the mess.

Keri was shocked and mortified at herself. What the hell was she doing? Why did she say that? Then the pragmatic part of her spoke up, reminding her of just how broke she was. There was no way she was going to enjoy someone fucking her in her ass. It just wasn't in the cards. So at a minimum, she would walk away from the bet with at least two thousand five hundred dollars.

And if she was right, which seemed like a sure thing, she would get the whole thing. She needed the money badly. She was almost out of funds, literally down to her last fifty bucks, all of which was in her wallet in her purse right now. That had to last her another four weeks until her next student loan check came in. Something had to change in a big way. She really didn't have any choice.

Both were silent as she helped clean up the spilled beer, her focusing on the floor while he worked on the leather couch. It took some time to get it all up and clear the air of the smell of spilled beer.

"Wait here, I gotta go change. Be right back."

Keri thought for a while longer as she watched the game on in front of her, not really seeing or remembering what was happening. It was a college football game from two teams she didn't follow and didn't care about, but it was still football, her favorite sport.

Donnie changed while his mind raced. Would she go for it? The possibility that she might wavered in the front of his mind like a desert mirage to a man crossing the desert. He barely noticed what he had put on before he walked back out to the room, sitting back down next to her on the now-clean couch. His heart was pounding.

"Why did you make the bet about Darrin, and not yourself?"

"Darrin needs to have some real life experience soon, or that boy is going to wear his dick away to a stump."

Keri couldn't help the laughter that came out of her, fueled by the adrenaline rushing through her system. She got herself under control once more before she dared to speak up once more.

"You're just playing the kind older brother?"

"Not exactly. I would get to watch also; which, I am certain, will be a truly memorable event that I will not forget any time soon." He kept his eyes focused on the big TV screen in front of them while he said it, his almost samurai-like self-control keeping him from ogling her from where he sat.

Today she was wearing a tank top over a sports bra which easily contained her smaller b-cup breasts, and a pair of workout shorts that were easily up to the task of maintaining her dignity. She sat with her legs folded under her with her knees towards him, which made for an alluring sight. He had to keep from looking at her, because his cock threatened to stand and salute if he did. Those dark brown eyes were incredible, especially when he was as horny as a goat.

She thought about it while he tried to not hold his breath.

The letter from her bank had pretty much made it a moot point. She had to. She was overdrawn now, and owed them just under a hundred dollars including the check that had bounced and the fees they bolted on.

"Why the change of heart?"

She sighed. "I am out of money. My checking account is overdrawn. I can only hope that I win the bet, or that I don't enjoy it and get half of it."

Donnie's heart went out to her. He knew she was not doing well, but he had no idea she was that close to the edge. Her sophomore year was going well; she'd bragged about her 4.0 GPA to him a few days ago when he'd asked how studies were progressing. It would be a huge loss to her if she had to drop out.

"Tell you what. I will pay you the twenty five hundred no matter what, as your part of the bet if you lose."

That put Keri's mind into a whirlwind. That made this less like a bet, and more like prostitution. She wasn't sure how she felt about that. On the one hand, she had no other resources to fall back on. Her parents had made it abundantly clear she was on her own, and they had no resources to spare for her.

She knew that was true, because he had been out of work for years with a bad back, and between his disability payments and her mother's meager income from her unskilled retail job, they barely kept their head just above water. They had been forced to move to an apartment and sell their house, but like a lot of other people, they had been upside down from the Great Recession, and had only been able to gain a few thousand dollars after the closing and everyone had been paid before them. That was money they had been glad to give her, but they had explained that when it was gone, it was gone, and she was on her own.

She really had nowhere else to turn. She couldn't even afford to move back in with her parents, unless she abandoned all of her belongings here.

But it was still, underneath, her getting paid to have sex. And not just any sex, but anal sex. Ugh. Did she really want to do this? Hell no. Did she need the money bad enough to do it anyways? Fuck. She did. The five thousand would make this a one-time thing. The twenty five hundred would mean she could finish out the year, get a car, and get a job that paid more than the retail crap she was getting right now. Was it worth it? Probably not. The cost to her inside would most likely something she would have trouble living with for a long time.

Then again, some of her classmates were rumored to have started stripping or working as escorts to make ends meet, in the hopes that no one found out what they were doing. This would at least keep it quiet, if she worded it right.

"If I do this, there has to be some stipulations that, if broken, result in penalties."

Donnie almost swallowed his tongue, before speaking up. "What kind of details are we talking about?"

"If anyone outside the three of us ever find out about any of this, even if I win all of it, I get an additional five thousand dollars. I don't want anyone else ever knowing anything about this, even if it is someone I will never meet. If Darrin or you ever even ask me for this again, or any other sex of any kind, including just asking to see me naked once more, I get a thousand. If this changes our situation here enough that I have to move out, I get a refund of all the rent money I have paid since I moved in, along with my deposit. And this agreement can be changed only if I agree to it in advance." She cleared her throat, and said one more thing. "And you have to tell me everything about why you are doing this, and why you picked your younger brother, and not yourself, as the person who would benefit from this."

"That is a lot of money for penalties if someone screws up."

"True, but it is mostly for risks under your control. It is mainly to prevent screw-ups. I won't have this come back to haunt me. I am planning on being an elementary school teacher. This getting out would destroy any and every chance of me ever working in that field ever again."

Donnie thought about it. She was seriously going to do this, he thought. It was such a rush. His physical senses were threatening to overwhelm him as his mind whirled onwards, trying to process this impossible situation.

"I will gladly tell you why I am doing this. It is because I want to help Darrin out, definitely. But it is also a bucket list item. I want to see a young, incredibly beautiful girl have anal sex for the first time while I ... well, you know." He blushed as he tried to say it, but he couldn't get the words out. His voyeuristic fantasies were something in which he had never been able to indulge in the past. This would be one for the ages.

"You think I am beautiful?"

"Keri, you are easily the most beautiful girl I have ever personally met, and probably will be for the rest of my life, no matter how long I live. You check all my boxes in what I consider to be the perfect girl. You are athletic and in great shape, you are smart, driven, you love all the same sports I do, you take good care of yourself, you absolutely adore children and will make an incredible mother someday, and your personality is a perfect match for me. I would marry you in a microsecond if I thought I was even close to in the same league as you, and you cared about me even one tiny fraction of how I feel about you."

Donnie clapped a hand over his mouth, shocked that so much of what he kept hidden inside had come out all at the same time.

Keri, for her part, simply looked at Donnie as if he had stood up and suddenly announced that he was going to have his space ship swing by and pick him up for his next mission. He thought all of that about her? The confusion inside only reached a higher level now. While she was definitely going to go through with the bet before, now she was totally unsure. He had feelings for her? How the hell had she missed that?

Then she realized that she had simply overlooked all the signs. The bets, some of which seemed set up for him to lose, the grace period on her rent, his forgiving her inability to pay for her share of the utilities from time to time; it all made sense if it was driven by some sense of how he felt about her personally.

But none of that solved her financial situation. She needed the money bad enough that she had considered getting a job at a strip club herself. It had been there in the back of her mind since Rochelle had confided in her some weeks ago. It went against everything she believed in, but she didn't have many options. She could always move back to her home state and work there, and hope that it didn't follow her back. None of this she spoke out loud.

"Well, that is a topic for another day," she said, and Donnie exhaled, suddenly realizing that he'd been holding his breath since his big revelation. He must have had more to drink than he realized.

"I want to also state that no one can have been drinking or doing any drugs when we do this if I lose. Everyone has to be sober when it is done, or the bet is off."

Donnie nodded. "That has to happen. This is not something that can be done when anyone is under the influence." Then he continued after a few breaths.

"So the bet is, if the Bruins win, I pay you five thousand dollars."

"All payments have to be in cash," she injected.

"Agreed. Cash. If the Wild win, I teach you how to have anal sex with Darrin, but he has to be moving inside you for at least a minute before he finishes inside you at the end. If he finishes too quickly, or he isn't inside you when he climaxes, the terms will have to be met again."

She winced internally at that, but didn't want to back out. "Continue."

"If the game ends in a tie, which happens rarely, the bet is off, and no one owes anyone anything. If anyone talks outside the three of us, you get a penalty payment of five thousand dollars. If Darrin or I bring it up again, or ask for anything sexual in the future, you get a penalty payment of one thousand dollars. If the situation here gets unworkable, and you have to move, I refund all rent payments you've already made, along with your deposit. And finally, you have to approve any changes to this agreement in advance of those changes taking effect. Is that everything?"

"I think that the bet has to be settled up as soon as possible. All money has to be paid to me no later than Monday so I can get it into the bank before close of business at 3pm."

"And if you lose, you have to pay up your end tomorrow during the day, no later than 2pm."

"I am fine with that. I mean, not really, but I'd rather get it over with." She shuddered inside, but steeled her nerves.

"Ok. Neither side can back out, or they forfeit their bet, and pay in full. Once we shake on it, it happens."

"Ok. That works." She spoke up again. "What about why you are doing this? Anything you want to add?"

"I think I said everything. Do you have any questions about that?"

"Yeah." She paused. "Have you ever seen me naked?"

"I saw part of your butt once, when your towel wasn't covering you properly. That's it."

She nodded in remembrance of that event.

"Have you masturbated to fantasies about me?"

"Do you really want to know?" He looked worried. She was a good tenant, and this could trigger the move-out clause before the bet even gets started.

"Yeah, I think I do."

"Ok, yes."

"How many times?"

"A few. I don't know the exact number. Not many. I try to limit my fantasies to anyone other than you. It's not a good idea otherwise." Rather than making her feel repulsed by learning that he had fantasied about her, the knowledge sent a frisson of arousal through her, which further clouded her judgement.

"I want to add something," she said suddenly.

"What is that?" He tried to hide his trepidation at the possibility that this might not happen.

"If I lose, this will not be me being submissive. I expect to still be treated with respect, before, during and after. No slapping, hitting, or any of that shit people talk about happening in pornos or whatever."

"I would never allow that. If he starts anything that might look like he is going there, I will personally pound the shit out of him. He has to act like an adult and learn to respect women if he is to have any hope of a normal relationship when he gets married." He sounded emphatic and entirely sincere.

She paused for a moment then nodded.

"Ok, that is everything. I agree. Make sure you tell Darrin about what happens if he talks."

Donnie reached over and held out his hand, and she shook on it.

The hockey game that evening started out easily enough in the beginning, making it look like she was going to win. The Bruins took an early 2-0 lead into the first intermission, and both teams added a goal in the second, making the score 3-1 in favor of Boston, who had been dominating the Wild throughout the first two periods.

The start of the third period seemed to be destined to continue the same way, but with one minor change. The Wild switched out their main goalie for a young new goalie the wild had just signed that hadn't had a lot of ice time.

The period slowly ground onwards, with both Keri and Donnie watching in complete focus, their hearts pounding as the high stakes of the bet wore on them both. Donnie was suddenly wondering why the hell he had bet so much money. He hoped he wasn't going back to his old days of the mild gambling addiction he had fought off, but it was too late for that. Neither side would back out. Neither could be the first to quit, because it was the same as losing.

A tripping penalty by a Bruins forward put the Wild on a power play, and only twenty-four seconds into the penalty, a massive slap shot from the point by a Wild defenseman moved at high speed across the ice, only to be tipped in by the forward waiting at the opposite side of the net from the shooter. The score on the screen was updated to 3-2, with Boston still in the lead.