Tom was nervous, and had been for the last six hours. That morning he had been in his own bed, and now he was taking a taxi from the airport into an unfamiliar city. He was always nervous when he took these trips; he knew people might judge him for it if they knew what he was up to.
This wasn’t the kind of trip a man pushing 40 should be doing, and the woman he was about to meet was hardly the sort of company he should be looking for. But primal urges do silly things to people, and as he saw his dark brown hair start to turn gray and his tall lean body begin to soften, he decided to make a change.
He started taking chances.
He started thinking about living in the moment.
Which brought Tom to that hotel bar, sipping at a glass of bourbon while he kept his eyes peeled for the woman. They’d only spoken for a few hours online, but each of them had made clear what they expected.
Tom knew that the suit he was wearing would serve him well. It was always better to go with something classic than to try and dress like someone he wasn’t. He wasn’t prepared for seeing her stroll in, making eye contact with him almost immediately. The little red dress she was wearing hugged her body tightly enough that he could see her toned abdomen and the pert swell of her modest breasts, more than enough for him to enjoy.
*He could also see the two hard points of her nipples poking through.*
Her lips were painted dark purple but her cheeks were as red as her outfit, and her. Sandy blonde hair was done up as if she was dressed for something far more formal than what they’d agreed to. She was almost half his age, barely out of college and yet strutted with confidence that made her seem wiser than her years, ***or more experienced.***
*It was a good look for her.*
She sat down on the stool next to his and tilted her head over to the side with a little smirk.
“So you’re Tom?” she whispered.
“In the flesh. It’s good to meet you, Kate.”
One of the rules they had already agreed to was that neither of them mention their last names. They assured each other of their identities long before he had booked his flight, but there was no sense in prying.
“It’ll be even better to meet me upstairs for your next drink, don’t you think?”
She wasn’t wasting any time, which surprised Tom. He’d never been with someone so young, so we knew that there was going to be differences but he wasn’t expecting that. He gave a curt nod to the bartender, and poured the remainder of that amber liquid down his throat in one long sip, keeping his blue eyes fixed on the deep brown pools of hers.
She was the one to lead him to the elevators, but it was Tom that ran his fingertips along the bare expanse of Kate’s back exposed by the dress. It took all his willpower not to pull it off right there; she was the most beautiful woman that he’d ever seen, but he knew better than to admit it.
His heart was beating in his chest when the hotel room door shut firmly behind them. It was a good room, with an enormous bed and a bathroom bigger than some people’s studio apartment; for one night It was worth every penny.
“So, it’s 50 dollars an hour, and 200 for every hour past when we planned to be here…” he whispered, his voice trembling just a bit as he watched Kate kick off her pumps and stretch her lithe body before turning to face him. If he didn’t know better from the way she was looking at him, unable to keep her gaze on his for long, he might have suspected she was nervous.
“Yeah…and we said that every orgasm each of us has is another hundred. Oral was 75, 150 for my pussy….”
The two of them rattled off numbers and acts, a veritable à la carte of sin. Both of them felt hot, circling each other at the foot of the bed as they spoke, every once in a while removing some accessory.
Her purse ended up on the dresser.
His socks were haphazardly kicked off and his jacket was hung up by the door.
She kept her necklace on, a delicate gold chain with a few semi-precious stones and one tasteful pendant. It was tight around her neck, though not quite a choker. Tom didn’t ask her to keep it on, but loved that she did.
“You’re overdressed,” she finally admitted, her voice louder as she found her confidence. She went for his belt with one hand and his tie with the other, pulling on both as their lips crashed together.
“Fuck me Tom. We have all night but I’m tired of waiting.”
She punctuated her words with a bite to his lower lip. The older man winced but refused to back down, giving her a bite of his own, then another down her neck, and another on her shoulder….
With her greedy, skilled hands, his clothes disappeared quickly, while he used his fingers to hike up her dress and find a wet pussy already dripping down her thighs, without so much as a thong to protect her modesty. Tom growled at the discovery, and began pumping his fingers inside her while his thumb circled her clit. Kate hadn’t been prepared for it, collapsing backward onto the bed before leaning up on her elbows and looking at him with hunger.
“You’re a bad man, Tom. I could be your daughter…but by the end of the night you’re going to be my *Daddy*.”
Whatever games Kate was playing, Tom was happy to give in. He wasn’t merely a slave to his lust, but a willing and enthusiastic participant. They’d spent enough time talking to know that she wasn’t the type to draw out a first time. His large hands peeled off her dress in one fell swoop, and as he crawled over her body, he realized just how small she was compared to him. Almost a foot shorter, almost half his weight.
Tight, *toned*, **perfect**.
His fantasy woman, all his for one night until one of them was expended, *satisfied*.
With Kate still reeling from the ministrations of his fingers, Tom grabbed her legs and spread them wide, pulling her to the edge of the bed while kissing and biting his way up her thighs. He lapped up the potent nectar that had coated the skin around her entrance, then ran his tongue along Kate’s folds once, then again. Only then did he close his lips and begin to suck at her, teasing her clit at first, then attacking it. Tom knelt before this goddess and worshiped her body, soon bringing his left hand back to probe her cunt while his mouth focused on Kate’s hood.
Every moan of Kate’s made him push a little deeper, suck a little harder, lash his tongue a bit faster. Tom’s right hand found one of her nipples and his deft fingers pinched and rolled the hard, pink nub. His eyes, once fixated on Kate’s, closed just as hers rolled back into her head.
Tom continued, and waited for the shudders of a well-earned climax, the cries of anguished ecstasy, and the feeling of Kate’s nails digging painfully into his scalp. In any other circumstances he would have recoiled, but Tom felt *honored* by her loss of control and raw need for him. He was rewarded with a flood of her juices, the smell and taste of her satisfaction fueling his own desire for more.
“Fuck me, Tom,” she moaned softly between labored gasps for breath, “there’s condoms in my purse.”
Tom remembered again that he had to use protection—if they didn’t, every rate would triple, and if he came inside her bare…that was an altogether higher price.
*The highest one.*
His fingers clumsily rolled the slick piece of latex over his throbbing member, and admired how he could see his veins still pulsing through that one last layer of separation between them. With only one stroke he knew he was ready, and pounced upon Kate, slapping her clit once before his primal instincts took over, and he plunged himself inside the young woman.
“Fuck yes, Tom, *harder*.”
Kate’s eyes locked onto his when he draped her legs over his shoulders and pinned her beneath his body, using his weight and strength to pound the small woman into the mattress. Tom felt his cock kiss her cervix when he bottomed out, and felt her muscles pull at his member when he’d draw back, as if trying to keep him in. Kate’s hands finally found his thighs to grip, but the woman was his to take as he pleased. Every hard thrust coaxed an enthusiastic consent to more.
Tom, caught in the moment with his senses dulled just enough by the condom felt her cum long before he felt his own climax, and watched Kate roll over, placing her angelic face down on the mattress while aiming her tight bubble butt skyward.
“***Harder,*** Tom. No one’s fucked me like this and I need *more* from you.”
With her hair wrapped around his balled fist, Tom did just that.
When Kate demanded he slap her ass, Tom did that too, leaving his mark on her by the time she came again. That time, he’d been close to orgasm, and the energy it had taken to dominate the voracious young woman had left him panting, slick with sweat, and staring at the ceiling to catch his breath. He didn’t even ask when Kate decided Tom had to feel her warm mouth sensuously blowing him, and her nails clawing his chest. With his right hand, Tom held her face down, then felt her teeth.
Tom froze as he realized she was pulling the condom off his cock, and the implication only made his ache for release grow. It didn’t matter what it cost; *Kate and Tom were going to fuck properly*.
Kate bobbed her head, forcing herself down again, gurgling and moaning around Tom’s cock as if she had a point to prove, only coming up for air when her cheeks turned crimson. Panting for air, she stroked Tom’s cock with both hands while a line of spit and precum dribbled down her chin.
Tom’s need to cum was agonizing, with only his willpower keeping him from erupting right then and there. Kate’s instincts clearly sensed it too, as she winked with a coy smirk and squeezed down on the base of his shaft.
“Not yet, big guy,” she insisted.
Kate straddled Tom’s hips and aimed that massive staff of his at her entrance. In spite of the soreness, her own arousal’s lubrication made her sink on Tom’s cock with ease.
Their hands met, fingers interlocked as she began to ride a man she barely knew for all she had. Her ass bounced off his thighs, her hips gyrated like a dancer’s, and Tom’s cock pulsed and dripped precum deep inside her.
“Mmm…you’re so fucking hard…such a good fuck….”
Tom couldn’t be sure if it was truth or roleplay as the young woman lost herself to the pleasure of using his cock, alternating between fast and slow, back and forth or up and down. Tom’s balls were drenched in their juices.
No man could last long experiencing *that*, and Kate sensed his throbs. She leaned down, placed her hands on his chest and ground her clit against his pelvis, rolling her hips.
“*It’s okay, Tom, fill me up, please.* ***I need your cum in me, Daddy. Won’t you?***”
Tom had never felt such intimacy as he flooded her womb, crying out her name before the young woman collapsed fully onto his chest.
Tom caressed the muscular back of the young woman with his calloused fingertips, while he gently kissed her cheek, waiting for her to recover. His cum steadily flowed from her pussy, and his shaft remained coated in the creamy mixture of their sin. He could hardly believe what they’d done, without knowing each other for more than a few hours.
*No one had ever done that before with him.*
But then, this wasn’t an ordinary night. Kate sat up, lifting herself fully off Tom’s half erect cock and began stroking it while looking into his eyes and biting her own lip.
“You’re doing so well, Tom. Now that you know what I can handle, how about you stop holding back, huh?”
**It would be a long night.**
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By the time Tom was awake, Kate had already showered. His palm print remained on her ass, as did red streaks down her back and thighs, and hickeys along her neck, thighs, and collar bone. For a minute, he wondered how a woman like her would ever put herself in some hotel room with a man like him. He felt lucky, honored, but also a bit sad to know that they’d never have met under a different circumstance. He’d never have had a chance.
Kate’s hair was damp, sticking to her pale skin still when she gestured for Tom to join her by the dresser.
______________________________________________________________________________
Tom counted out each bill one by one; more money than he’d ever seen at one time, and looked back at Kate.
“It’s all here, but you didn’t have to tip me,” he whispered, handing two hundred dollars back to the young woman and curling her fingers around the bills.
“Keep it as a deposit, for next time?” she insisted.
Tom blushed, then smiled as he pulled her close and stole one more kiss from her full, pouting lips. *He had a new favorite customer.*
Source: reddit.com/r/eroticliterature/comments/x8rnpf/a_simple_arrangement_40s_m_20s_foralrisky