Betting It All

by Gilmore

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa, mt/Fa, Consensual, Reluctant, Heterosexual, Fiction, Oral Sex, Anal Sex, Masturbation, Spitting, Voyeurism, .

Desc: Erotica Sex Story: What happens when a beautiful but somewhat inexperienced poor college girl with a minor gambling addiction gets offered a wager with indecent stakes? This started out as a primer on how to have anal sex, but that just sounded dull and boring, so I put a story around it. It is as medically accurate as I can make it, based on personal experience and research. Hopefully people will read it and try it out for themselves, with enjoyable results. I know there are typos. I apologize in advance.

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 He was more withdrawn because of what had been happening with his family, but in the four months since she had moved into the spare bedroom, he had slowly opened up to her.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.

.... There is more of this story ...

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