Charitable Deal

Dressed in virginal white lingerie, Barbara felt very slutty. She was lying face down across an ottoman with her ass about to be violated- and she was being paid for it. She was excited but nervous as her ass had never had a cock before. Would it hurt or would she enjoy it? Her husband's finger was lubing her ass and another finger was teasing her pussy; that felt good.

Of course, five grand was a lot of money. Barbara could accept some pain for that much. Still, she hoped it wouldn't be too bad since she'd agreed to be fucked in the ass four more times for "only" One Thousand each. The $5,000 was extra for her virginity.

While nervous, she was getting aroused from her husband's attention. His lubed finger felt very sexy and the whole scene was erotic. She tensed as she became aware that Tim was putting lube on the dildo. They'd agreed on a silicon one about 5" long and 1" inch in diameter. It was to be a test and her final opportunity to back out. She felt it pushing against her anus and slipping inside. It stretched her and felt huge but wasn't too bad. The test had been passed and that made her both excited and afraid. Barbara reflected on the unusual arrangement they'd negotiated.

Tim and Barbara had made a lot of money the previous year in a large real estate sale. They'd decided to increase their charitable giving and had benefited several local groups. Barbara wanted to make a substantial gift to a home for unwed mothers but Tim had disagreed since he didn't like the woman in charge. Since they couldn't agree, the gift was tabled.

About a month later Tim had suggested a solution to their impasse. He'd said he'd pay Barbara for some special sex and she could use the money to support any charity she wanted. She had been offended by the idea. In fact, she'd been indignant that he could suggest such a thing. He'd said she had to lighten up and give his idea a minute's thought. He meant no disrespect; it was just a kinky idea that he thought might be hot for both of them. It was entirely up to her. A little later Barbara had calmed down and confessed that there was something sexy about the idea. They'd wound up in bed having wild sex- apparently both turned on by the thought Tim had expressed.

As they recovered from their respective orgasms Tim had brought the subject up again. He suggested a two month trial plan that could be extended if they agreed. He assured Barbara she wouldn't have to do anything she didn't agree to and that the arrangement would be their secret. He fleshed out his plan by saying as a first step he'd withdraw $5000 in cash from the bank and replenish it as needed. There was no budget; she could earn as much as she wanted to donate. When he was in the mood he'd make her an offer of a specific sum for a specific sex act or for a date that would include some agreed upon sexual aspects. For example, he might offer to pay her $X for a sexual act or he might pay her for wearing something sexy but then they'd have regular sex afterwards. She'd be free to agree or refuse or she could negotiate for a higher price or suggest limits on what she'd do for the price. If she was feeling horny or charitable- or both- she could initiate the offer by offering him a sexual experience she thought he'd like. In those cases she'd have to come up with the suggested pricing. In all cases he'd pay her in cash and she'd be required to make her donations in cash and to get a receipt for tax purposes. Barbara had refused. How could she give hundreds in cash to the nun at the unwed mother's home? Tim had insisted on the cash donations saying that the nun would never ask about the source of the cash. It would be their secret that she'd earned the cash "on her back" doing obscene things. Tim said that aspect was part of what made the whole plan arousing. If she just wrote a check it would spoil everything.

Barbara had finally agreed to Tim's terms- agreeing that making the donations using the cash she'd earned did tie the whole naughty plan together. This had emboldened him to suggest 10% of Barbara's earnings should be devoted to buying her some new lingerie and sex toys. You need some "tools of the trade", Tim had said. These items would only be used for their special sexual dates so they'd remain special. He'd offered to advance up to $1000 to buy her first wardrobe of sexy clothes and toys with 10% of her future earnings to be used to gradually retire her debt. Barbara had been shocked at the amount but warmed to the idea as she realized Tim was prepared to pay handsomely for her services. She hadn't thought about the quantity of money until then. It was arousing to think of yourself as a high priced call girl and gratifying to think of the good her donations could do.

A few days later Tim had given Barbara a suggested price list for a number of sex acts or sexual evenings. She'd been confused at the very first entry which said, "Blow job, $500." Barbara had said, "Why do you want to pay for a blow job? It's not often but from time to time you get those for free." Tim had then clarified that for $500 he'd expect a blow job whenever he wanted one and that it should be of "professional" quality. He'd said, for example, it might be offered by Barbara wearing some sexy lingerie and some dark red lipstick and acting in a sexy, seductive manner. It should reflect her best efforts and not just be a means to ejaculation. "As you suck my cock you should think of how great you can make it so I'll want another very soon; that's how you'll make the most money to help the poor women and children at the unwed mother's home." Barbara smiled at his self serving generosity.

Tim asked Barbara to review his list and accept or reject the acts listed and their respective prices. He also suggested that she add any sexual scenes or acts to the list that she might think Tim would enjoy along with a price. The list could be supplemented or amended as their experience evolved.

Barbara found the list largely predictable but with a few surprises that weren't literally sex acts. "Wear a corset of Tim's choice for the evening, $500" and "A riding crop on your ass for 30 minutes, $300" were surprises. "Maintain a shaved pussy for a month, $1000" seemed like easy money since Barbara had kept her pussy shaved until about a year ago. "An evening of bondage, $1000" was intriguing.

From Tim's initial list Barbara had rejected "anal sex, $1000." This prompted a discussion of Barbara's fear that it would be painful. Tim had assured her that he'd be gentle. Tim reminded Barbara of a "how to" video on anal sex he'd bought. That evening they had watched it together and both had been aroused. Barbara had still rejected Tim's proposal even at an increase to $2000. She'd said, "It's the first time that frightens me. After that I might even like it but the thought of your cock pushing into me the first time is pretty intimidating." This had led to the negotiated package deal of $5000 for the first time and four follow up sessions at $1000 each. She'd insisted on the dildo test before he fucked her as a final escape. Given that concession Barbara had caved in at the higher price. Nine thousand dollars for her charity was an offer she couldn't refuse.

Now it was happening for real. The test dildo had come and gone; it hadn't been bad which should be some comfort. Tim was telling her to relax. She could feel him kneeling between her spread thighs and getting ready to fuck her. Her mind raced as she glanced over to the end table with its stack of 50 hundred dollar bills. She couldn't back out and forfeit the money. His cock was at her opening. She could feel it pressing against her as she struggled to relax. A few seconds later it felt like he was going to rip her apart but that pain was soon replaced by an incredible fullness- not comfortable but also not painful. As Tim slid in all the way and then retreated for the first full stroke, Barbara's nerve endings were pleased. It felt surprisingly good- maybe even better than good. She was thrilled by her success. It felt good- physically and mentally. While he'd started slowly and gently, Tim had gradually begun thrusting into her- pushing forcefully and deep. She was being fucked- no euphemisms sufficed. She found she was pushing back against his thrusts- getting his cock in as deep as she could. Soon she realized she was incredibly excited by being fucked in the ass. It felt great and she'd just earned $5000 for the unwed mothers! An unexpected orgasm swept through her. Her body spasmed wildly but Tim's cock stayed buried in her. It felt huge but also seemed to be custom fitted for her ass. She loved it! The nun was going to get a large donation; maybe she'd delay the donation until the end of the month and shoot for $20,000. Barbara was looking forward to get fucked in the ass a lot!