Sheena was broke, and she really didn’t feel like going back to waiting tables. She’d been there, done that, if you know what I mean. What brilliant, gorgeous, hilarious, and organized girl needed sore feet and ass grabbing for meager tips? But she needed help making ends meet while she was building up her freelance writing biz—no easy feat. Yet she wasn’t about to give up on all the freedom that could bring.
Since she loved sex and all things erotic, and had a lovely, dark, and open mind on her, she considered stripping. She considered being an escort. She considered massaging men and jacking them off at the end. After all, this was by far the easiest industry to enter: no experience needed, no questions asked. Just be thin and young and pretty and be willing to open all your holes to your customers, because the customer is always right. Oh, and be willing to pretend you’re his girlfriend too, should the need arise. Easy peasy. The feminist in her balked at it all, but the same part of her that was grossed out was also madly turned on, was the thing.
There were physical sensations… Things she felt in her gut, and between her legs, and in all the places where she was joined and could be torn apart. These feelings came alive when she thought of being paid solely to open her body. Of course, part of the coming alive was fear.
“Why don’t you just get a sugar daddy?” asked her friend, Hannah, smiling and twirling her silky blonde locks around her pinky finger as she sucked up the last of her vanilla milkshake. They were at Fatt’s, the local diner, having lunch. Hannah was one to talk. She had a trust fund. She had an inheritance. She was in fucking law school. She didn’t come from pure dysfunction. Ok, she knew that last one was overkill sob-story style, but it was kinda true. The girls were a complementary contrast: Hannah with her blonde curly hair and cashmere sweaters, and Sheena with her long, straight, black hair, plaid shirts, and ripped jeans.
“A sugar daddy.” Sheena grinned at her friend, draining the last of her iced mocha. It was hot outside, and she wanted to get back to the sun.
“What, like, on one of those disgusting sites, with one of those pathetic men?” she said.
“Pathetic, maybe, but loaded, Sheena, and ready to pay you to be their fucking arm candy.”
“Arm candy, huh? Ya think that’s all they’d want?” Sarcastic tone.
“Well you were thinking about sex work, yeah? This would be like that, except safer. You find one dude. Ideally one without any STIs, and that you’re relatively attracted to. And you work out your terms in advance. So you know what you’re getting from him, and he knows what he’s getting from you.”
Sheena raised her eyebrows theatrically at her friend.
“What? Sheena, it could even be hot. Who knows?” Hannah laughed.
“Have you done this before, Hannah?”
“Me? No. I’m a rich bitch, remember? I’m just well-informed,” she shrugged, and swept up the bill for both of them.
After lunch, the two girls parted ways and Sheena went to a café to finish writing a mind-numbing blog on sewage treatment that was due later that day. She thought to herself how nice it would be to focus her energies on her fantasy novel instead, to have the financial freedom to do something she could be proud of. Distracted from work, she found herself on seekingarrangement.com, making herself an account. She couldn’t believe how many men were apparently secret millionaires, and she was bothered by how much easier it seemed for men to make money in this world than women.
But my asset is my body, she thought wryly. My tits and ass. There were men her age, 28, who already had it made. And they were now looking to purchase a girlfriend. The thing that really struck her was how many of them were a) married, and b) looking for “real relationships” with “elegant, and smart women” as opposed to simple sex for cash. At least that’s how they chose to frame it, anyway. She thought simple sex for cash would be more honest, less gross. And maybe even hot.
Two weeks later, Sheena found herself getting ready to meet her first sugar daddy, Derek the venture capitalist. Divorced. Hannah had given him a thumbs up, so he couldn’t be that bad. He was 54 (the oldest guy she had ever gone out with), but handsome, in a Pretty Woman-era Richard Gere kinda way. Which was totally saying something, let’s not kid ourselves. This guy had it all: money, a shiny car, and a full head of luscious grey hair. And his face. She tried to think of herself as a potential Julia Roberts-type. Worthy of rescue.
They had worked out an “arrangement” that Sheena was quite happy about: no pretending, no hoping for love. No dinner or movies. Just a weekly “date” wherein they would be “intimate” for a couple of hours and he would pay her $300 a pop. He had requested that she paint her nails, so she had painted them red - her first run-in with nail polish in years. They had discussed her “limits,” and he was not to make her do any rimming. And no pee.
As she slipped into her one and only little black dress, she felt kinda filthy, but she also felt really powerful. It was an unsettling combination. Although she had never learned how to put on make-up, the finishing touch was red lipstick. Her black hair was woven elegantly into a side-braid that reached her nipple. She looked fabulous, and she knew it. Oh, and red velvet Mary-Janes on her feet. It fed into the whole daddy-daughter thing Derek seemed into, plus she didn’t own any heels. She felt a little like Dorothy from the Wizard of Oz.
She was going to his place. She didn’t exactly want to host him in her tiny studio apartment. It was too rough around the edges, just like her.
She rang his doorbell. It was a real house. Stone. There was a stone in her throat. She swallowed. She hadn’t wanted to meet at his house, but in the end, her intuition had told her it was fine. Plus she wanted even less to be seen with him in public. A lot of people knew her. May sound sketchy, but their discussion of his three teenage daughters had assuaged her concerns. She had also texted his address to Hannah, just in case.
As he opened the door, her breath caught in her throat. This can’t be right, she thought. He really was a beautiful man. Why then, was he paying for her? What was wrong with him that she couldn’t see? She smiled, said hello, and went inside.
“Sheena. Beautiful name,” he said, taking her coat. “It’s lovely to meet you. Now, I know you’re probably nervous. Just please, relax, make yourself at home. I am not a crazy. Would you like a drink? Or some water?” He smiled.
“I’ll have a drink,” she said, sitting on his spotless white couch and looking around without trying to appear too out of her element.
She was. Out of her element.
The place was huge, white, and immaculate. It was almost too predictable. But there were plants. Lots of plants. Signs of life.
“Wine or scotch?”
“Um, wine, please,” she smiled graciously. She noted that the wine was white, probably because red wine in a place this white would
be a disaster.
Handing her the glass, he sat down.
“So Sheena,” he said. “You’re a writer.”
“Yes, you could say that.”
But she didn’t feel like making small talk. She knew he didn’t either, the way he was subtly tracing her crossed legs with his gaze. She wanted to make a mess of his expensive white couch. She wanted to ride for her money. In spite of herself, and perhaps because of herself, Sheena found herself very calm now that she was there, now that she had laid eyes on him, now that he had commenced the small talk. It was reassuring. But he was a large, attractive man, and now she wanted his actions to speak for themselves.
As though reading her mind, he stopped talking, and pulled a wad of cash out of his pocket, placing it on the table, all the while looking at her. She suddenly realized she had become very wet. “Come here,” he said. She felt an excited rush of blood to her face, and obeyed, trying to hide it, and failing. She stood in front of him. He looked up at her.
“You know, I’m not some pathetic old guy who can’t get laid without paying for it, right, my dear?” Still sitting, he slid his hands under her dress to rest on her hips, fingertips on her ass. She was wearing a thong, her best one: a simple, black piece. He shivered as his hands made contact with her skin, and so did she. She felt her nipples get hard. Her pussy was warm and wanting, flowering for the wrongness of it all.
“Of course,” she said, seriously, looking into his eyes.
“I’m just a very busy man, is all. No time for love, no time for dating, no time for searching,” he said. “All I have time for is making money,” he continued sadly still gazing up at her, and running his fingers slowly around her ass to the back. “So money is what I have to offer. And I’m happy to help.”
Suddenly, he hiked her thong up into her ass, and held it there, tightly with one hand. She gasped, but didn’t move. The other hand came to her front, as he pushed the material to one side to expose her freshly waxed pussy. She really had done everything in her power to come off as young and fresh as possible. It was fun to feed into his fantasy. She had even gone one further and dabbed a tiny bit of lavender oil just below her navel.
He let out a low moan as he inhaled her, pulling her closer by her hips. His head fully hidden under her dress now, he ran his tongue up and down her slit: slowly, relishing the moment. Sheena let her head fall back and her eyes fall shut. She breathed deeply. And then he was pulling her dress off. She lifted her arms to let him.
“You’re stunning,” he said, standing to toss her dress on a chair and taking her in hungrily with his eyes.
“Thank you, sir,” she responded.
He had requested via email that she call him sir. Hearing her utter the word made him instantly hard. Watching her stand there somewhat shyly in her pushed-aside thong, lace black bra, and red Mary-Janes was simply too erotic. She was right there with him. She felt what he felt. He stepped up to her, and pushing her braid aside, began kissing her neck, gently, deep breathing as he did, until she could practically feel him pulsing from within her. It was warm. It was very warm.
He stood back, and started removing his belt. “Remove your bra, please,” he said softly. She complied. “And your thong.” She slowly slipped out of her thong, tossing it to the side. She was only wearing her red little-girl shoes now, and nothing else. She could feel his eyes glued to her soft, sweet-smelling, bare pussy, and her innocent braid.
“On your knees.” He said it all very softly.
Sheena kneeled in front of him, on the white carpet. He had dropped his pants and was hard, half an inch from her mouth.
“You’ve been a bad little girl,” he said softly, caressing her jaw with his hands, cradling her face gently.
“I’m sorry, daddy,” she said. “I didn’t mean to.”
“I can’t very well let you strut around town looking the way that you do, turning all those boys’ heads... You belong to me, sweetheart. No more showing off for other boys. It’s partially my fault, I guess, since I haven’t really shown you yet how it is you belong to me. But I think you’re old enough now to learn. I’m going to teach you how to open your throat for daddy. You will learn to please me or there will be consequences.”
“Yes sir,” she said, a hot, wet core forming inside her.
“Open your mouth.”
She opened her mouth, and he slid his cock inside, holding the back of her neck with his two hands. And then he fucked her throat: deep, and loud. She was talented at giving head, at deepthroating. She’d always been incredibly turned on when guys treated her mouth like a pussy.
He didn’t take any of his clothes off; it was like he wasn’t staying long. Just long enough to fuck her face and get back to his scotch.
Sheena maintained steady eye contact with her new sugar daddy as he was slapping the back of her throat, as she half-choked about a half a dozen times. Her eyes watered and her mouth stretched, and yet still, she looked at him. And then he was losing control, losing the clean lines of his apartment, and he was cumming all over her face. Predictable.
Once she had returned from washing her face, he said: “Can I make you cum?”
Surprised, but still extremely aroused, she said “Sure.”
She sat on the couch. Pants fully done up again, still fully clothed, he crouched in front of her, and pushed her legs wide apart. He sucked on her clit, thrust his tongue inside of her and out again, running from her outer labia all the way out to her thighs. She cried out. Her eyes resting on the wad of cash still on the table, she had never been this kind of truly dirty turned-on before. Dirty as cash. Her pussy was throbbing for release.
And then he slid three fingers inside her. Reaching slightly upward to tickle her g-spot while still licking and kissing her clit, he thrust into her firmly but not too deep. Sheena moaned with a kind of starved delight and mere minutes in, she clenched hard around his fingers, pulling them further into her. And then she was gushing all over his white couch, and squirting, a clear arc, across the room, and onto his immaculate carpet.
Splayed out, red shoes in the air, gasping, catching her breath as her swollen, exposed pussy tried to regain composure, she realized she had forgotten to warn him that she sometimes… did that.
“That has never happened before,” she lied. “Oh my god.”
“That’s alright,” he laughed. Getting over the initial surprise, he seemed quite pleased with himself. “The cleaners will take care of it.”
“The cleaners,” She smiled.
On her way out, cash in wallet, he kissed her, full and deep on the lips, and she felt that maybe, just maybe, there was something real in it.
“See you next week,” he said.
“Yes, next week.”