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?"
