Booty Shorts Sugar Daddy

This story was awarded second place in Literotica's 2024 Valentine's Day Contest. Congratulations to the other winners, Thanagar's Slingshot, and Smuttyandfun's Surprise Valentine. Thank you to all the other authors who participated and all the readers who voted.

This story was also an entry in Omenainen's 2024 Pink Orchid Event, featuring erotic tales of women characters having agency in their own lives. I encourage you to check it out anyway.

Despite the title, this is a romance like most of my stories. Just setting your expectations. Enjoy!

~~~ Los Angeles, California, August ~~~

"Hi, are you Monica?"

The butterflies in her stomach were shouting at her to say no, that this was all a mistake. But she could tell that the woman knew it was her and was just being polite. She shifted nervously in her chair.

"Yes, hi. I'm Monica. Hi." She mentally cursed how awkward she felt.

The woman set her designer handbag on the seat next to her then sat down while holding up a hand to catch the waitress's attention. Monica could see her bag was big enough to hold a MacBook Air, the corner of the laptop poking up out of it.

"It's nice to meet you in person," she said. "I've enjoyed chatting with you."

"Thanks. Um... I'm not sure what to call you."

"You can keep calling me Charlie, most people do. My real name is Charlene, but I only go by that when I'm doing business. I appreciate you understanding my need for anonymity, at least on the site."

"Of course, I--"

Monica was interrupted by the waitress's arrival. Charlie ordered a cappuccino, Monica declined a refill on her latte. She'd arrived early out of nervousness.

"So tell me a little more about yourself, Monica. You said you're in a creative field?"

"I'm an assistant set dresser."

"Ah! The film industry. Makes sense, Hollywood and all. Are you a native Angelino or did you move here for your career?"

"No, I grew up in Los Angeles. I went to UCLA for film and design."

"How do you like the work?"

"Oh, I love it! I mean, when I can get it. The show I was working on just wrapped its second season and hasn't been picked up for a third yet, so I'm between gigs."

"Anything I might have seen?"

Monica gave the name of the mid-tier dramedy she'd been working on and was unsurprised to see no hint of recognition on Charlie's face.

"I don't think I've heard of that, sorry."

"It's on Apple TV."

"Ah. Well, I don't have much time for binging TV shows, so you'll have to forgive me. Maybe if this works out, you can introduce me to it."

That idea gave Monica pause. Watching TV together wasn't something she'd thought would be a part of this arrangement.

"So... since you sort of brought it up, what exactly is your idea of what we're talking about here?"

Charlie was about to answer, but paused when the waitress dropped off her coffee. Charlie delicately blotted her lipstick with the paper napkin the waitress had set under her cup, then took a careful sip before setting down the cup and looking directly at Monica.

"You mean, you want to know what is exactly going to be involved with you fucking me for money?"

~~~

"This is nuts, Monica!" Monica's roommate yelled at her three weeks earlier.

"I don't think it's nuts. It seems like exactly what I want right now."

"Signing up to find some rich, old, fat dude who will keep you on the side and pay you cash for blowjobs and sex is what you want?!" Hailey gestured at Monica's laptop where a sugar daddy finder website was open in a browser tab, the page displaying a profile creation template.

"Okay, one, I get to decide who I hook up with. If anyone who approaches me is too old or fat for me, I just say no. And two, it's not like I'm thinking of turning tricks. I'm just looking to find some guy who wants no strings attached sex once in a while. Also one who happens to be wealthy and can shower me with gifts. Cash gifts, not to put too fine a point on it."

"And you're okay with being some married guy's side piece?"

"Hey, if he's stepping out on his wife, they probably shouldn't be together anyway."

"Yes, I'm well aware of your attitude towards marriage since Rod."

The year before, a month before Monica's wedding she'd come home early and found her fiancé, Rodney, in a compromising position. It still was an open question as to what had been the most shocking, that he'd been sucking a guy's dick, or that the strap-on he'd been getting railed in the ass with at the time was being worn by her sister.

The resulting drama explosion had meant she mostly hadn't talked to any of her family in over a year. Her sister, Marie, for obvious reasons. Her parents were divorced and were third generation Americans, so they weren't quite as socially conservative as Monica's grandparents, whose parents had immigrated from Korea.

Still, not being privy to most of the gory details, her mother had pushed her hard to "forgive and forget." Rodney was an up and coming movie producer after all, and would be able to let Monica stay home and raise a family, which was the most important thing in her mind, not getting hung up on Rod's "little peccadilloes". After a few of her mother's scolding sessions, she had finally blown up and told her the unvarnished truth. Things had been insufferably awkward between them after that.

Her dad had simply told her he'd never liked Rodney much, which pissed her off because he'd never said anything while they'd been together. In retrospect she would have appreciated the warning.

"I guess if I found out he had kids I'd be out."

"Glad to know there are some lines you won't cross."

"Do you want to squeeze another roommate into this place? Or move to the valley? Because I can't afford to live here much longer as it is."

Hailey was a special effects makeup artist. They were both still trying to claw back the losses they'd suffered after the Covid shutdown and the writer's and SAG-AFTRA strikes, and now their landlord had just raised the rent on their tiny two bedroom Hollywood apartment.

"No, but I settled for a second gig at Starbucks. You could try

that

instead of selling yourself."

"If my body, my choice means anything then it has to mean everything. Besides, I haven't gotten laid in forever. Maybe I'll get lucky and whatever rich sap I hook up with won't be half-bad in bed. Now, are you going to help me take some cheesecake photos or not?"

Hailey had grudgingly used Monica's phone to take several photos of her, starting with some bikini shots by their tiny apartment pool, then some underwear shots on her bed. She'd even posted one photo of herself in the nude, although she'd used a strategic pose so as to not actually show any of her important bits.

Monica's profile had garnered immediate interest, generating several emails in the first twenty-four hours. Her Korean ethnicity and jet black hair was a rare look on the site, as most of the profiles in the L.A. area were typical blonde California girls. She knew her body was a big part of the draw too, as she'd spent close to a decade playing field hockey, even starting for the UCLA club team. But she liked to think it wasn't the only plus she had going. She'd tried to make her profile as witty as possible and highlight her college degree and creative mind.

She'd met with two of her potential benefactors in person, but the first had clearly been almost sixty (his profile and photos he'd sent had suggested otherwise by close to two decades.) The second one had told her that his particular kink was coming on girl's faces and she'd have to be okay with that.

She was not, in fact, okay with that.

Then she'd gotten her first message from Charlie. They'd flirted for a while and Monica had liked the sense of humor which had come across in her DM's. After several messages back and forth, Charlie had sent her a photo.

That's when things had taken a turn.

The photo, an outdoor candid apparently taken at a party, showed a rather striking woman, maybe five years older than Monica, with blonde hair in a short, professional haircut that probably cost as much as Monica's car payment. She was in jeans and a very expensive white linen button down shirt.

She was laughing at something. Her face was striking, her full lipped smile displaying both intelligence, but also her eyes showed an unmistakable shrewdness. This was a formidable woman. She was also curvy in all the right places, eliciting a brief feeling of envy in Monica who, while athletic, didn't have much in the way of curves.

Monica had been taken aback that she'd been flirting with a woman for a week and hadn't realized it. She re-checked Charlie's profile and, sure enough, she hadn't noticed it'd said Charlie was "F seeking F". She'd then gone back and checked her own profile and realized when she'd set it to "open to anything" it meant she'd been advertising to both sexes on the site.

She'd blocked Charlie, then updated her profile, but after a day to think about it, she'd reconsidered. She'd experimented a bit in college, and had had a fling with a girl. She wasn't opposed to sex with women, but a lifetime of thinking about finding Mr. Right and starting a family had conditioned her to be looking for a man when seeking a relationship.

But she wasn't looking for a relationship, was she? Not that kind anyway. Not anymore.

Her mercenary instincts took over, and she'd resumed flirting. They'd quickly set up a face-to-face meeting the next Friday at four o'clock at a trendy coffee place in Hancock Park, halfway between Hollywood and downtown where Charlie was working.

~~~

"You're pretty direct, aren't you?" Monica asked.

"I don't have time in my life for beating around the bush," Charlie said, "And given that you're looking for this kind of relationship, I figured you'd appreciate some directness." Her smile offered a challenge.

Monica accepted.

"I do appreciate that, in fact. I'll be direct too. What are you offering and what do you want in return?"

Charlie took another sip of her cappuccino, clearly sizing Monica up. Monica could see her reach a decision.

"I live in New York, but I travel to L.A. for business every month. When I'm here, I'd like you to be available to hang out."

"Hang out?" Monica said, the skepticism dripping off the words.

Charlie laughed. "I'm a busy woman, Monica, I don't have time for relationships. Besides, in my position most women who want to date me aren't looking for a relationship, they're looking to either climb up my social ladder, or for money. I appreciate that you're being up-front about the latter, and that you clearly want no strings or complications."

"Okay," Monica nodded.

"So, while I do expect this... ah, arrangement... would involve me getting to have my way with you, I would also like to do some social things together. Most of the people I'm here to see for business are either employees or people wanting my business and I'd like to spend time with someone who's none of those. I'm almost never here longer than a week, but I usually spend a weekend each time. My timetable can be flexible around your commitments. It could be dinner on a weeknight, or an outing on the weekend. You can show me parts of L.A. I don't know."

Monica thought about it. She'd imagined any sugar daddy she hooked up with would simply want her to come to a hotel, service him and then get out.

"You do realize you're describing the plot of Pretty Woman, right?"

Charlie laughed and Monica couldn't help finding it charming.

"Yes, but I'm not Richard Gere, you aren't a street-walking hooker and we won't be falling in love at the end of the movie. This will simply be you helping me out with some companionship and me helping you out with money, something I have more of than I'll ever be able to spend. Once or twice a month while I'm here."

"Okay. Here's some more directness. What do I get? And what are your conditions?"

"My conditions are that I require discretion. You can talk to your friends about the situation if you like, as long as you don't use my name or anything you find out about my identity, my company, things like that."

"Fair."

"We can both end it at any time for any reason. Also, I'm the only one that you enter into this kind of agreement with, as long as our agreement is in place. You can have all the personal relationships you want. I don't need to know and won't interfere, but no other sugar daddies."

"Shouldn't that be 'sugar mommy'?"

"That just sounds wrong, but you do

not

have to call me daddy. Unless you want to."

Monica giggled.

"That's what I get. Here's what you get. As long as you spare me some of your time a couple times a month and maintain discretion, I'll give you five thousand dollars, in cash, every month. And I'll pick up the tab for any activities we do together."

Monica barely managed to hold back a gasp. That was far more than she'd hoped when she'd embarked on this adventure. She tried to play it cool.

"That's acceptable, I suppose."

Charlie's knowing smile told Monica that her delight in the number had been perfectly transparent to Charlie.

"So what do you think? Should we give it a try?"

Monica sipped her latte, ostensibly to give herself time to think. But it was time she didn't need. This deal exceeded her wildest dreams. Five grand was three times her half of the rent. If she did it for a year it would literally double her monthly income. And she'd only have to give herself up to this beautiful, rich woman once or twice a month?

"Yes, please."

It was Charlie's turn to giggle.

"Now there's one bit of unpleasantness," she reached into her bag and pulled out a document, unfolded it and slid it across the table to Monica, "This is a non-disclosure agreement."

"You want me to sign an NDA?" Monica was quite familiar with them, having had to sign several while involved in various film and TV projects.

"For my protection. I realize that what we're doing is... let's say quasi-legal and this is probably not enforceable. But I will tell you that the language is tight enough that if you sell or give away any information about our arrangement to the tabloids or write a book about me or

anything

like that, I can sue you. Even if I don't win I can drag it out for years and the legal fees would be astronomically ruinous. Probably more than you'd make in five years at your set dressing job."

Monica gulped, flipping through the pages and scanning the dense legalese. She knew she had no way of understanding most of it, but she believed Charlie could use it to make her regret being indiscrete.

"That's the stick. Here's my carrot." Charlie reached into her bag again and set a thick envelope on the table.

Monica stared at it.

"This is five thousand dollars, in cash, free and clear, just for saying yes. Call it a signing bonus. We can start when I come to town next month." She pulled out a second envelope and set it next to the first. "This is another five thousand if you happen to be free this weekend. Or at least until Sunday morning, I'm flying to Hong Kong Sunday afternoon."

The pause before she answered was barely perceptible.

"Do you have a pen? "

The rest of the evening was a blur. She'd texted Hailey to let her know she wouldn't be coming home, then fended off the inevitable avalanche of enquiring return texts. All Hailey had known was that Monica was going to meet up with someone from the site, not that it was a woman. She certainly hadn't expected her to be gone for the entire weekend. Neither had Monica, for that matter.

Charlie had a car and driver waiting, who picked them up outside the coffee shop and took them to one of L.A.'s trendiest new sushi restaurants. Monica had heard of it, but never in a million years would have been able to afford it,

if

she could have gotten a table, which she certainly wouldn't have been able to.

The restaurant was phenomenal, partly due to the food, partly due to Monica spotting several A-list actors and directors. She'd been around enough celebrities due to her career to play it cool and fend off the urge to approach anyone for autographs or selfies. But mainly the meal was great because of Charlie. She was funny, and smart. They spent most of their dining experience making up crazy backstories for each celebrity they saw and laughing loudly.

Afterwards they went to a fancy martini bar, again one that Monica's pocketbook would never have allowed her to frequent.

Two drinks were all Monica allowed herself, as she didn't want to get sloppy and turn off her future meal ticket.

When the car finally pulled up to Charlie's hotel, the butterflies started doing a tango in Monica's stomach.

This is it. I'm going into this hotel, where rooms are probably a thousand dollars a night, and I'm going to have sex with this woman. For all intents and purposes a complete stranger. And I'm doing it for money.

So why do I suddenly have the feeling like it's going to be the hottest thing I've ever done?

No surprise, Charlie's suite was on the upper floors. L.A. was spread out beyond the floor to ceiling windows like a carpet of fireflies, the view only slightly adulterated by Charlie turning on a few soft lights.

"Can I get you anything? Water? There's a bottle of wine in the mini-bar, a sauvignon blanc I really love. The concierge makes sure it's stocked every visit for me."

Monica was suddenly very self conscious. "Um, this may sound strange, but can I use your shower? And maybe borrow your razor if that's not too forward? I didn't think I'd... when I left my house to meet you this afternoon, I didn't think I'd be here tonight."

Charlie smiled warmly, clearly not offended by Monica's presumptuousness.

"Of course. It's off the bedroom. My toiletries kit is on the counter and there are plenty of towels. Take your time."

The bathroom was bigger than Monica's bedroom and she did take her time, luxuriating in the spray from multiple shower heads. She carefully shaved her legs and everything else. She assumed she'd be doing most of the work, but in case Charlie decided to reciprocate she didn't want to appear unkempt. She took the time to blow dry her hair, standing at the sink, wrapped in a towel. Although, staring at her reflection in the mirror, a corner of her mind realized she was stalling because of nervousness.

"Are you really doing this?" she asked herself.

This is what you told Hailey you wanted. No strings sex, with someone who would be generous with their wallet.

"I'd been thinking it would be some guy."

If it were some guy, it'd probably be some older, out of shape dude, cheating on his wife. Someone who'd want me to suck his dick then, if i were lucky, I'd get the three-pump chump treatment. Charlie is... beautiful. And she's funny. And brilliant!

"Fuck it, let's do this," she told mirror Monica.

Summoning her courage, she unwrapped the towel and tossed it on the bathroom counter.

Time to grab the bull by the horns.

Charlie was in the living room leaning against the window and staring out at L.A., a thoughtful look on her face, a glass of white wine cradled to her chest. She'd turned out the lights to better enjoy the view. Monica's breath caught in her throat. Charlie heard it and turned towards her.

Charlie had taken time to freshen up herself, and was wearing only a short cream colored peignoir that ended at the top of her thighs. The thin spaghetti straps were taut as they struggled to hold back Charlie's ample chest.

"You are so beautiful."

Monica had been thinking the exact same thing, and at first was unsure if she'd said it aloud or Charlie had when she'd taken in the sight of Monica's completely nude form.