Cupid's Little Helper

This is an entry for "Pink Orchid 2023 for Women-Centric Erotica Challenge"

It is also for the "Valentine's Day Contest 2023 at Literotica"

[I have to admit, the Valentine's angle is a little tenuous, but what the heck? We really admire the effort Literotica and event organizers put into these specials and like to draw attention to them whenever we can.]

Caladenia had come to the hotel bar just as a warm-up, planning on moving on later to a nearby dance club to really get her groove on. But plans change, don't they?

As she'd prepared for tonight's outing, she'd been imagining the kind of guys she usually found at dance clubs. Young studs with hot bodies and graceful moves. In the shower she'd even thought tonight might be one of those two-for-one nights, where she'd take on two men and let their youthful energy make up for their lack of experience and finesse.

But now she'd spotted a man who looked like he might not only have some real experience, but still had the strength and energy to put it to real use on her.

She put him in his mid-thirties, her own age. He was mostly bald, but had embraced it with no shame, only extra virility. He'd come in wearing a nice sports coat, but now it was draped on the back of his chair. Underneath he wore a high-end polo that stretched nicely across a broad chest and shoulders. His biceps were well developed and his forearms were corded with sinew. His hands would certainly be strong. Strong hands to pick her up, to hold her down, to really take her the way she felt like being taken tonight.

He was seated at a two-person table, while she perched on a barstool. They'd had a little eye contact, but Caladenia realized she was checking him out harder than he was checking her. While that understandably tweaked her insecurity about advancing age, in the end it piqued her interest more. She knew she was still smoking hot and the fact that he was self-confident enough to know that he was too and so wasn't staring and drooling increased the chances that he would be confident and in control in bed.

Wait, yes, there it was, his eye had definitely travelled up her body from bared toes to thick, chestnut hair. The narrowed eyes and slight lift to the corner of his mouth showed that he liked what he saw. She was sure it wouldn't be long before he came to invite her to sit with him.

At least she was sure until another man walked up to the stud's table and bent over to kiss him before taking the other chair. Gay? Damn! What a shame.

Her position at the bar allowed her to watch them from the corner of her eye without being obvious. The new guy was younger, maybe 27, and he was fucking gorgeous. His face could easily be featured in ads selling cologne or clothes. He was well-dressed and clearly trim and fit. It was hard to judge while they were seated, but the pretty boy was probably the same height as the hard man, but clearly a good thirty pounds lighter.

It was also clear who was top and bottom in the relationship. The bald hunk probably dominated the younger man the way she'd hoped he would dominate her. Cala suddenly wondered if he'd be willing to dominate both of them.

Caladenia was always eager to expand her already wide range of experience and even wider range of fantasy, so she was instantly excited about adding something new to the latter and hopefully also the former.

She'd never seen live man-on-man sex and had never really gotten into the occasional gay porn scene she'd watched. But right now, the idea of watching her manly man take control of his more slender companion was making her pussy moist.

Her mind's eye had always been a fast, flexible cinema and now it was offering up an image of herself kneeling, naked, alongside the bald guy and guiding his large (of course it was large) prick into the other dude's tight little ass. That almost immediately morphed into her being alongside the slender guy, side-by-side, on hands and knees as he was. Her vision, of course, had the director's view and she was looking down as the bald guy moved that beautiful cock back and forth between their two assholes, both shiny with copious amounts of lube. His cock in one butt, a finger or two in the other, switching prick and digits back and forth, taking her like just another nancy-boy.

The idea was so exciting her pussy had gone from moist to damp and was well on its way to wet. She spun on her stool toward them and was just getting ready to walk over and offer her indecent proposal, when the maître d' of the adjoining restaurant came over to let them know their table was ready. Both of their asses looked fine as they walked away and Caladenia sat back disappointed on her stool and swallowed the saliva that had built up in her watering mouth.

"Um, is everything okay?"

Caladenia did a mental head shake. She realized she was staring off into the distance, but couldn't have said how long she'd been doing it. Somewhere in there a guy had sat down two stools away from her, around the corner of the bar.

"Hm, what?" she responded.

"I'm sorry, I don't mean to be nosy, but you look kind of sad or lost or...well, I just thought I'd check if you were okay, if you needed any help."

Caladenia finally focused on the man. A definite step down from her young Yul Brynner. Probably 45 and probably quite handsome at 25, but he'd let himself go. Still, it was sweet of him to check on her, most people weren't that perceptive or that nice these days.

"Oh, no, I'm okay. But thanks for asking." She gave him a slight smile.

That brightened his visage, showing more clearly the handsome face buried under the growing jowls and double chin.

"At first I thought you were looking for somebody, that maybe your date had stood you up. But, of course, that would never happen."

A pick up line? she chuckled to herself. But she needed to reset herself emotionally, so she went fishing for the rest of the compliment.

"Really?" she said. "Why not? I mean, it happens to everybody sometime."

"To you?" the big man said. "Not likely. You are too fuc--, I mean, just too beautiful for someone to pass on a chance to be with you."

"Aren't you a sweetheart?" she said. "But let's face it, when a woman passes thirty she loses thirty percent of her attractiveness. From a ten to a seven just like that."

"What?" He seemed genuinely shocked at her statement. Of course, she had just made it up. But thinking about it in the back of her mind, she suspected there was some truth to it in a superficial, social media culture.

"No way!" he protested. "I can't imagine how you could have been more beautiful when you were younger." His eyes started darting around, looking for some kind of guidance in the mirror behind the bar to help him explain himself. He apparently found it, because he pointed at something on the bar's back counter.

Caladenia followed his finger and saw a small grouping of wine bottles, apparently the features of the week.

"It's like wine," he said. "The new wine may be fresh and fruity, with loads of promise, but it's the wine that's been years in the cask, years in the bottle that's most treasured. Because all its subtleties and nuances have finally matured into their richest flavours."

"Oh, my God," Cala half groaned. "Did you just come up with that or is it from a book?"

The man blushed. "Too much?"

"No," she said. "It was actually wonderful. I even think you're right. But I'm afraid that our culture doesn't judge women the same way it judges wine."

"And thus Modern Western Civilization follows the Roman Empire into decay and destruction," he intoned.

Caladenia laughed.

"Say, can I buy you a glass of wine?" the big man asked.

Caladenia thought the confidence in his voice was like the beauty in his face, a daily occurrence when he was young, but appearing only in flashes now. She decided to reward it.

"Why, yes, I think a fine, mature red would be lovely."

He waved the bartender over and while the young woman poured, Caladenia motioned the man to the stool beside her.

His name was Patrick and he was staying at the hotel while he attended a weekend seminar on something legal or financial or a cross between them. That part of a man's world seldom interested Cala. She was much more into what was going on in people's hearts and minds.

As they talked, Caladenia teased out the personal details. Details he certainly hadn't planned on sharing. But the brushing of her breast against his arm and the butterfly landings of her hand on his leg soon had him mesmerized and spilling some pretty personal beans.

As he dropped hints about an unsatisfying sex life at home and a wife who'd let herself go even more than he had, Caladenia found herself moving on from her earlier fantasy about a threesome with two bi-guys to one she'd lived out with great pleasure before. Hooker.

"So," Patrick said with some hesitation. "Like I said earlier, I have a room, actually a suite, here at the hotel. It's got a decent bar, would you like to come up for a nightcap?"

"A nightcap?" she said with a raised eyebrow. "Before we say goodnight or before you take me to bed?"

"Well...well..." he stammered.

"I know you said some sweet things earlier, when you could see I was feeling down. But do you really want to spend your free weekend with a middle-aged woman? We actually aren't just like wine, you know. If you're going to step out on your wife, wouldn't you prefer a tight, fresh college co-ed?" she said with a bit of challenge in her voice.

"Middle-aged? I'm middle-aged. You're still young and beautiful!" he declared sincerely.

"Hmm. I think you're just trying to score. Let me ask you, if I was a lady of the night, would you still think I was beautiful enough to pay for it?"

"A lady of the--, oh, a hoo--, I mean..."

"If," she repeated. "Hypothetically speaking."

"Well, honestly, I've never..." His voice trailed off again, completely lost.

"We'll put a hypothetical on that side of the equation as well," she said in friendly tone, like they were talking about ethical decisions far less momentous. "If I was that kind of woman and you were that kind of man, would you still find me beautiful enough to hire me or would you slide off that stool and look for someone else?" Then she added, with just a touch of cruelty, "Or head up to your lonely room and lonely bed and stroke yourself wishing I was with you?"

Her hand had gone to his knee at the beginning of her play and had crawled up his thigh as she spoke. As the words, 'stroke yourself', passed her lips, her hand was doing just that and she was pleased with the level of stiffness she'd already brought out in him.

"Speaking hypothetically," he mumbled.

She released her grip on his member. "It's all hypothetical," she purred. Then she squeezed him tightly. "Until it becomes real."

The words rushed out of him. "Yes. If I was going to pay, you're definitely beautiful enough to pay for."

As her hand had gotten closer to his crotch, her face, her whole body had also drawn closer to him and now she was almost whispering in his ear.

"You know why else I'm worth paying for? I'm not only beautiful, I'm nasty." Her hand was fully in his crotch now and his breaths were fast and shallow. "I'm more beautiful than your wife, but more importantly, I'm much nastier."

"My wi--"

"Shh, you don't have to say it, you don't have to say anything. Married life can be great, very rewarding, but it can also be very long and monotonous. It's just not reasonable to expect a human to only eat vanilla, even if it is his favourite flavour. A little helping of mint pistachio now and then is not really a sin after all, it's just a way of keeping all of your life more vibrant. And if you're going to allow yourself a little mint pistachio on a lonely night are you going to buy the supermarket brand or splurge on some Haagen Daaz?"

The rhythmic pulsing of her hand on his cock and her voice in his ear had Patrick half hypnotized.

"How much does Haagen Daaz cost these days?"

"Well now, that depends doesn't it?"

She pulled her head back a bit and he looked questioningly into her eyes.

"On how much you want to eat," she said. "How long you want to savour it and what extras you'd like to add." His raised eyebrows indicated another question. "You know, maybe sprinkles or chopped nuts." She leaned back into his ear. "Or maybe you're the kind of man who likes to spray his own whipped cream all over his scoops of ice cream?" She pressed her breasts more tightly into the side of his arm.

"Or maybe," Her hand pushed deeper into his crotch, going under him as far as she could and pressing an extended finger up against his taint. "You're a very adventurous man who really likes to root around in his bowl of delights."

Patrick was hooked, although he mentally stopped using the word hooker and replaced it with High End Escort to help him justify what he was doing. Hell, if Caladenia had agreed to go upstairs with him for free, it would have been only the second time he'd successfully scored in the two years since he'd strayed into unfaithfulness. And the first woman had been a sloppy drunk, who was barely conscious by the time he'd finished. He wasn't out looking for a new wife after all, so why not make the whole thing easier, with a much better outcome?

After they'd negotiated a price, the woman did something that reassured him he'd made the right choice in going with a professional.

"Baby," Cala cooed as she pulled a small object out of her purse and put it on the bar in front of Patrick. "I want you to get every dollar's worth. And just as importantly, I want you to give me every dollar's worth, because I really like my work."

She pressed a catch on the small object and its lid popped up. Patrick saw that it was a decorative pillbox and inside he saw blue pills.

"But, I don't need--" he began.

"I know you don't," she soothed. "For the first time. But I don't want to wait an hour for the second time. And when I get going, I'll definitely want a third time. Don't you want to give me a third time?"

Christ! The first time was going to be right there at the bar in his pants if she kept looking, touching and talking like that. Patrick pinched a pill out of the box, popped it into his mouth, and washed it down with a gulp of his wine.

The first-time-John put both of their bar tabs on his room, including a generous tip for the staff, and led the beautiful woman out of the bar on his arm. Of course, some things can't be put on a room tab or charge card, so they stopped for cash at a universal ATM in the lobby before heading on to the elevators.

The doors hadn't finished closing before Caladenia was pressing herself up against him and had both hands in his crotch, opening his fly and fishing out a cock that was half-swollen and dripping pre-cum.

The half-swollen state was upgraded to fully hard within seconds and by the time they passed the third floor, she'd maneuvered them so that her back and head were against the wall and he was thrusting into her hungry, talented mouth.

She stopped him around the eighth or ninth, just long enough to say, "I wish your wife was here to see how well you fuck a stranger's pretty mouth. I want to kiss her with my mouth full of your cum."

Then she was on him again and would have gotten that mouthful of cum if the ride had lasted even two floors more. However, the bell had dinged, the car had stopped, and the doors had slid open on the tenth.

Patrick tried to pull back and hide his Johnson away when he heard the bell, but Caladenia closed her lips tightly around the crown of his head and held him in place. She cast her eyes to the side as the doors opened, hoping against hope that someone would be there to witness her wantonness. Unfortunately, the hallway was empty, but the thrill of possible discovery still sent a fresh wave through her puss.

'Exhibitionist slut!' she declared to herself.

'Fuckin' Ay', herself replied.

She didn't let her client put his prick away even after the elevator stopped. Instead, she grabbed it as she stood and pulled him out of the car by it.

"Which way?" she asked.

"Left," he groaned. "Room 1010".

As soon as they staggered through the door, she was on her knees again, picking up where she'd left off in the lift.

"Fuck my mouth some more," she moaned. "Show your wife you know how to treat a woman."

In about a minute, certainly no more than two, Patrick gave in to Caladenia's abilities and urging and sent the results of his most powerful orgasm in years straight into her eager, gulping throat. When he pulled out, she grabbed his shaft and rubbed the sticky head all over her face.

To give credit to Patrick, he returned the oral favour just as enthusiastically and gave her two orgasms before bringing his cock back into play. And to give him even more credit, that was only about a half hour after his first load, so the second erection was still mostly him rather than Daddy's little helper, at least at its start.

As Cala lay back on the King-Sized bed and let the tremors of her back-to-back orgasms shake through her, she felt her cunny with her hand. The lips were puffy and her clit was still energized and stiff. Then she felt something else stiff as Patrick got up on his knees and rubbed his reborn cock against her blood-swollen labia.

She took her time with that second stiffie, really playing it out and giving Patrick plenty of sprinkles and chopped nuts in the way of multiple positions and dirty talk she knew he wasn't getting at home. Cowgirl, both standard and reverse. Doggy style up on hands and knees and then flat on the mattress. Missionary, but with her legs spread up and back so her knees touched her shoulders. Encouraging him to move her as he would, to take his pleasure as he would, as she honestly told him how much she enjoyed being his fuck toy.

Then, lots of having him go back and forth between her cunt and her mouth during which she told him again that she wished his wife was there so that each could taste the other's pussy juice on his beautiful cock. She'd determined that Patrick was unsure about his cheating; he wasn't happy at home, but he hadn't become a total asshole yet. In cases like this she liked to build it into a positive, shared experience, at least in the man's mind. That way, his insecurity didn't get in the way of Cala taking her illicit pleasure now, and his guilt didn't screw up his relationship with his wife later.

He finished that session partway between mouth and pussy, yanking off his rubber and spraying his second load all over her small round breasts with their extended nipples. She wiped one breast with her fingers, bringing them to her mouth to suck clean. Then she pulled his head in to lick the other breast clean. She had no doubt he'd be trying to get his wife to try something similar in the near future and she honestly wished him good luck with it.

They took a break after the impromptu bukkake. He ordered a cheese and fruit plate and bottle of champagne from room service and they showered while waiting for it to arrive. Then they sat propped up against the headboard, with the sheet to their waists, and chatted while enjoying the snacks.

"So, Caladenia, that's a pretty unique name, where's it from?"

"It's from the Caladenia Latifolia, the Pink Fairy Orchid. My mother was on a work vacation in Australia in her gap year and spent a few months at an orchid nursery. I got the distinct impression she was bent over a bed of Pink Fairies when my father pollinated her. When they handed me to her in hospital, all pink and throwing my arms out wide, Caladenia it was."

Patrick laughed while he took the cheese tray and moved it to a nightstand. Then, quite casually, showing more of the confidence and bravado of his youth, he slid the bedsheet down off their lower bodies, positioned himself between her legs, and gently but firmly spread them. Bemused, Cala bent her knees to help him see more clearly between her legs.