The Charity Trap

Shelly

"It's time to decide, Shelly. Do we have a deal or don't we? It's your decision, but you need to choose."

The quintessential "soccer mom" hadn't imagined that anyone would see her in her underwear today. It was a good thing her mother taught her always to wear something presentable in case she was in a car accident. "You don't want the paramedics rolling their eyes at your shabby, faded panties," she warned. As always, Mom was right.

So there she stood in a nice, clean peach-colored bra and panties set, and nothing else. Her shoes, socks, jeans and top lay on the nearby black leather sofa. And now she had to decide whether to cross that very scary line and take off the rest.

Shelly was pretty damn hot in high school 15 years ago, and the years had been gentle. She was blessed with a face everyone would call "cute" for the rest of her life, and although she wasn't the same weight she was then, the few added pounds were more or less evenly distributed. Petite and fairly athletic, she drew the attention of many of the other dads when she and her husband attended their kids' games and other events. Rick didn't mind because Shelly had been, and always would be true blue. In fact, he liked how the other men desired her.

But still, there she was, half naked in front of a man she had only met 20 minutes ago. This was a lot different than her usual tightly scheduled day. Time to fish or cut bait, as Rick would say.

The invitation had come from a nonprofit she had never heard of. It included an access keycard and directions to the penthouse office. The nonprofit had electronically transferred $10,000 to her pet cause, the local no-kill animal shelter. That got her attention. It was a third of the budget for the complete remodel and expansion they had dreamed about for years. The only condition was that she would tell no one about the meeting.

It was kind of mysterious, like a secret agent movie -- kind of exciting. So she entered the lobby of a downtown skyscraper and took one of the main elevators to the 77th floor. She felt out of place among the executives, lawyers, venture capitalists and other folks who roamed the halls in buildings like this. Following instructions, when she arrived on 77 she found another small elevator to her left, her keycard opening those doors. One flight up and she exited into the penthouse office.

The decor was spare, in neutral shades, and with an amazing view with floor to ceiling glass. Just a fraction of the entire penthouse level, the office was less than a thousand square feet, with another room adjacent.

There behind his desk she recognized Derek Shannon, 33, entrepreneur, billionaire, and habitual wealth creator and accumulator. Some thought him almost handsome, others saw him as a bit of a primitive, as if he had come from an earlier time. Built like a heavyweight boxer, His $8,000 suit didn't really change that impression. His body looked hard and his face craggy. Some said he resembled a young version of that old character actor Jack Palance. He made an effort to appear welcoming that was only marginally effective.

"Good. Punctual. It shows respect. Come in and sit down."

Completely out of her element, Shelly timidly took a seat on the other side of the desk, and thanked Mr. Shannon for his generous donation. After that, she didn't know why she was here. Was she supposed to praise him for a time, and was that what he wanted? "We are so grateful, Mr. Shannon. It's so hard raising money for these poor helpless animals, and when your funds showed up in our account, why, most of us just cried, I have to tell you. You don't know what it means--"

"Oh, yes, of course, and you are very welcome. Glad to help the puppies and all that," interrupted Derek. "Now, why I asked you here. You might have heard of me as a person who makes deals, and I am. Every time I buy a cappuccino, it is a transaction, and both sides must comply with the terms. I know it sounds a bit, er, much, but that's how I see things. Do you get what I'm saying?"

""Well, of course, I guess so. That makes sense."

"Good. Now my $10,000 donation is a deal without any conditions, so that contract has been completed. Both parties are satisfied. Now I would like to propose another arrangement for you to consider.

"Open the envelope you see on the desk. It's a cashier's check to the shelter for the remaining $20,000 that you need."

"Oh my goodness, Mr. Shannon, I don't know what to say. This is so kind of you." Shelly's eyes moistened and she dabbed at them with her hand.

"Good. Here's the thing. This check has a small condition. Something you could do. Just a few minutes of your time. I know it will sound shocking and of course you can leave that check behind and our meeting will be over with no hard feelings. But the thing is that...well...I would like to see you naked for five minutes in exchange for that additional donation. No sex, no touching, just looking."

Shelly was silent for several moments as she processed what Derek had said. "I don't know what to say, Mr. Shannon. I...don't think this is right. I'm going to leave now."

"Perfectly OK, thank you for coming in, Shelly." Derek seemed even less appealing as his voice got a little lower and quieter. He looked her in the eye, deadly serious. "Just one word of warning. Say nothing about this to anyone ever. This is my only demand. The consequences would be devastating for you, the shelter, and your family. You know I am extremely wealthy, and my expertise and abilities in the cyber world has few equals. You can't imagine the havoc I can unleash if you seek to damage my reputation by gossiping about me. That's all I ask. Say nothing. Do you understand?"

"No, no, I won't tell anybody, ever. I promise. I didn't ask for any trouble. Please leave us alone."

His mood lightened. "Then we have no problem at all, Shelly. That's all I ask. I'm sorry if I upset you." Derek tried to form a friendly smile.

She turned toward the elevator, but then stopped and thought about how wonderful it would be to finish the remodel and expansion this year. She turned back at Derek. "How do I know you won't be recording this and putting me on the Internet?"

"That is a very intelligent question. It would be a massive risk for me. I could go to prison for that. And if I wanted to make videos with nude women I could produce a Hollywood-quality version for my private consumption or for the world at any time I wanted, with any number of world-class beauties. So no, for my own benefit and protection, there are no cameras or any recording going on here. After you leave, this will in essence never have happened. We will never speak again."

"Just five minutes? And no creepy poses?"

"Correct. Just you naked, not covering yourself. Nothing gynecological." Shelly blushed. She took the check and examined it. "OK. But you stay back there." Derek smiled and nodded. Negotiation complete.

*

And now we are back with Shelly in her underwear.

Reaching back, she unhooked her bra, releasing pretty and soft, natural breasts. Then she pulled down her panties, and took them both to the couch.

Derek started his phone timer, and proceeded to enjoy the view. "Good body. But you wax. I don't like that. It makes a woman look like a child. Creepy." Derek looked her over and assessed her as he would buying a boat or a startup tech firm. "Sorry." she said quietly, wondering why she even replied. The seconds crawled by. "I don't like it when a mature woman tries to look like a little girl. Turns me off. There's nothing wrong with pubic hair. Especially when it matches what's on your head, but I can't tell, can I?" Shelly didn't respond. Her chest and face was pink. This was taking forever.

"Let's see your bottom then." She turned around, feeling his eyes scanning her ass and thighs, judging her, invading her privacy. "Very pretty for your age. Now turn back around and face me, and clasp your hands behind your head." She hesitated. "I said nothing gynecological. Do it." Shelly stared at the ceiling as the pose made her breasts rise a little. "You take care of yourself. Your husband should appreciate you. I'm sure I would. Except for the bare pussy. Does he like it that way?" Shut the fuck up, she thought, but she remained silent.

After an eternity, Derek's phone dinged. "Time's up. We're all done, Shelly. You can get dressed. Best of luck to you and the shelter. I'm glad to help the, uh, animals."

She felt even more naked as she hurried to the couch and quickly pulled her panties on and fumbled with her bra as he watched. It was strange, she thought, as she left, knowing she could never tell anyone about this, not even her husband, believing Derek's threat was real. She would have to forget all about this as much as she could. She felt a little unfaithful, but she wasn't really. She hadn't changed at all since this happened, had she? She wasn't sure. Keep thinking about the shelter.

Derek

Derek smiled and relived what just happened as the elevator door closed. He loved how some women were so shy, even some who were probably quite experienced sexually. It was all about context and motivation. They just weren't prepared to be naked and displayed. It was powerful, and Derek liked to use power. It was his fetish, said one of his analysts. He got off on it mentally, and sometimes physically.

Derek wasn't exactly a people person.

For him is was about control and other people following through on their agreements and the deals they made. Shelly followed through. She did her part of the deal. People had learned over the years not to renege on any deal with Derek. He couldn't abide it. He wouldn't stand for it. That's how he got what he wanted. No one was ever forced. Everything was always a free choice. But once a choice was made, that deal would be concluded or jointly renegotiated to all parties' satisfaction.

Even when he was in preschool this was non-negotiable. One day he lent Tommy a quarter because the child had forgotten his money. Tommy promised to pay Derek back the next day, but the next day he forgot to bring the quarter. Right after class Derek took one of Tommy's shoes and said he would get it back when he got his quarter back. It seemed fair, since he knew the shoe was worth more than the quarter. Even as a small child he knew that one shoe was of no use to Tommy and that this would ensure he would be made whole.

What he got instead was a talking-to from the teacher, the shoe taken from him and returned to Tommy, and a conference with his parents and the principal the next day. First the principal spoke, then his parents explained why what he did was wrong. Then the principal talked some more, but Derek was simply waiting for them to stop talking and when they did he calmy asked for his quarter back. All three adults sighed, and the principal went to her purse and gave him a quarter. Derek wished her luck being paid back by Tommy, as he seemed unreliable.

In college a girl said she would sleep with him if he took her out to an expensive dinner and a concert. When the evening was done she said she was too tired and they could meet tomorrow night. But then she blocked his phone and ignored him when he tried to talk to her. He didn't get angry, but wrote her off as someone who didn't fulfil her end of the deal. A few weeks later he hacked into three credit bureaus and ruined her credit. Before that he emptied her bank account. He didn't take her money. It wasn't his. He just disappeared it.

Derek hadn't changed a whole lot since then, at least in terms of deals and agreements and getting what was his.

Kaylee

Two days after Shelly's short visit, Kaylee had an appointment. He hoped this visit would be much different than with Shelly. He had no other business after he was done with Kaylee and wanted an intense experience.

Kaylee: So adorable, so fresh, so young. At 21 she was a junior at the local university, and so painfully earnest it would break your heart. Walking purposefully toward the building entrance, keycard in hand, so excited at the invitation to meet the person who had funded a new food bank in her city. It would serve 200 people a day when it opened in a few months, and everything was paid for the first two years: Storefront, utilities, staff, insurance, stock -- everything. She had been working on this project since she was a senior in high school, and hadn't gotten far with the city or the county. They had pledges for less than 10% of the cost, until an angel flew in with bags of money. She was so looking forward to meeting her angel.

A new nonprofit, City Food Bank LLC, would administer the project, and it was all set. She couldn't believe her dream had come true.

Her parents from Brazil, with beautiful reddish-brown skin, Kaylee attracted the attention of almost every male at school, and several of the females too. Slim, pretty, with a winning smile, Kaylee enjoyed many friendships at college, but dated little. She wanted to save the world instead of party, and those who got to know her thought that she just might do it someday. She cared so much that she made others care too.

Stepping out of the small elevator and into Derek's "special office," Kaylee was bowled over by the penthouse view.

Derek was bowled over by Kaylee. Five foot four, perfectly groomed, with excellent posture and a lovely proportioned figure, Kaylee favored the preppy look she had adopted years before. Blue blazer over a crisp white blouse, tucked into a wool plaid skirt that was short enough to show off her gorgeous legs. Spotting Derek, she spun toward him which cause the skirt to swirl up, revealing a bit of thigh.

Oh, I do want to see where those legs meet, thought Derek, trying not to stare.

"Kaylee, so good of you to come."

The girl approached Derek as he rose to shake her hand. "Please have a seat."

"Thank you so much, Mr. Shannon. I just have to tell you how ecstatic I am at your incredibly generous gift to the community! We never expected this. You are just an angel to do this. I'm lost for words. I don't know what to say."

"Well, have a seat, Kaylee, and relax. I have a very interesting idea for you to consider, now that we've settled this business with the City Food Bank. Would you like to hear about what I am considering for four additional food banks for the area?"

"What? FOUR other food banks? Oh my goodness. I'm just overwhelmed. I don't know what to say."

"Well, look at the monitors on your right, and you can see the details. It's really five times what my foundation is already committed to do. The funding is in place, and all I have to do is approve them from my desk. I can do that today.

"But these will be different in just one way, depending on what happens right now."

The smile dimmed a tad, and then disappeared from Kaylee's face as Derek bluntly explained the conditions of his approval. He was again very clear about the dire consequences if she ever breathed a word about this offer to anyone. She believed him. His wealth and abilities were well established.

"So I can approve these immediately if we agree. Of course, there's no reason for me to deceive you on this. This amount of money is a rounding error in accounting with some of my companies. You can be absolutely certain that there will be five food banks operating fully if you comply. One thousand poor people a day fed."

Kaylee had lost her joyfulness, and eyes down, quietly asked, "What exactly do I have to do?"

"Whatever I want, for the next hour or two. Any sexual act, including restraints and even some pain if I choose. Nothing too extreme. Maybe your bottom would be a bit sore or your nipples might hurt until tomorrow. Or not. Depends on what I feel like. Your body will be mine to do with as I like. Do you have anyone you're seeing, who might notice any marks or wear and tear?"

"No one right now."

"Well, good. Then what do you say? You are free to leave and no hard feelings. Everything promised will be delivered and we'll feed those poor people as you wanted. Or you can strip and show me what I think will be a terribly beautiful body."

A tear ran down the girl's cheek. "I can't refuse. That's 800 more people every day who won't go hungry. I can't live with myself if I don't. So yes, go ahead. I'll do what you want."

He took the computer mouse and clicked four times, creating funding and organization for four more food banks instantly. He showed her on the screen, but reassured her, "You can be completely confident about this. You know my reputation for finishing deals and keeping my end of the bargain, and also because this is pocket change for me. I really don't care about the money. I would have funded nine more. Oh, I probably should have said that."

Her head spinning, the bronze beauty rose and began to undress. For her it was as if she saw herself from the outside, watching her body comply. She tried to remove herself from the embarrassment and surrender. But she could still feel it deep inside.

"Leave your panties on. There's not much to them, though, is there?"

A light, lacy bra had supported her pretty little brown breasts, and it was on the couch with the rest of her things. Standing there with just a tiny G-string, Kaylee felt Derek's eyes all over her body. Derek rose from his chair and took Kaylee by the arm and led her over to the couch. Sitting, his face was about at her thighs. He looked up, and she met his gaze, and then he pulled her G-string down her legs. She tried to remember to breathe.

"Quite furry there, aren't we?" He petted her between her legs as if he were caressing a kitten. "Well, how natural. Step out of those and spread your legs." Kaylee obeyed, and he stroked the insides of her thighs. They were incredibly smooth and soft. He slipped his hand up her slit, and she tensed up. "Easy, girl. We have a long way to go. Relax. I'm going to experience all of you. Just think of 1,000 people being fed each day instead of 200. This is what you're doing now."

Gently, he guided her over his knee, her lovely brown ass in full view. He spread her bottom cheeks to see her rosebud, just to startle her, which it did. "Oh that is so cute. Are you sensitive there?" Brushing his fingertips past her anus, she made a little noise. He so loved it when he could get them to vocalize unintentionally.

"Now, have you been good today? No? Oh dear."

Kaylee's spanking began with just light smacks, more for the sound than the impact. Instinctively, Kaylee put her hand back to protect her ass, but Derek grabbed her wrist and chided her, "No, no, dear. You agreed to be spanked, remember?"

Silence.

(smack!)

"Yes, yes, I did!"

"Then do what you're told. Spread your legs open."

She complied, and accepted stinging slaps to the insides of her thighs, and then back to her now pink bottom. It looked very sexy with her beautiful brown skin.

"Are you going to follow instructions now?"

(Quietly) "Yes."

"Good." Derek's fingertips glided gently over Kaylee's butt and legs, teasing her between her cheeks, sliding by her not-bare sex. He knew what he was doing, and in spite of her distress, she was getting wet.

"Bend your right leg." This opened the girl for Derek's fingers, which probed her vagina, now moist and slippery. "That's a good girl. You're getting all wet for me so my cock can slip right up into you. You know I'm going to fuck you, don't you, Kaylee?"

"Yes."

"And you're going to suck my cock?"

"Yes."

"Very good. Because if you just do what you promised, we'll be fine. And you might enjoy it. Your body obviously likes what I'm doing. Now get up and face me."

Kaylee stood up, and tried to comfort her butt as she stood naked in front of Derek. It was warm from the punishment. She had never felt so exposed. She was scared, angry, excited, aroused, confused."