Jack met Cheryl in the most clichéd way possible. Their flight was delayed into Detroit, and they both missed their connection to Chicago. They met at the rental counter, where Cheryl was complaining to the Hertz lady about not being able to rent, but she was adamant about their policy: _no rentals under 25_. And..well, Cheryl was 22. No rental for you.
Jack, of course, had no problem getting a car. He was 42, for one, and Hertz Platinum, for another. He’d accrued something like a million airline miles over his lifetime.
“Uh, I heard you’re going to Chicago” he said. “I can drive you, I’m going there as well”.
The drive started easy enough. Introductions: Cheryl was 21, flying home from college, she would be graduating in a few months. Jack was an executive at an unnamed consulting firm in Chicago. He was pleasant and charming. She was sweet, although perhaps she spent a bit too much time on her phone, flipping from instagram to snapchat and typing out messages with a speed that Jack found, quite frankly, impressive. They got along.
Pretty soon though, the trip to Chicago turned into a comedy of errors. The light snow turned into a blizzard somewhere around Battle Creek. By Kalamazoo it was obvious that the conditions were far too dangerous to drive.
Cheryl called three hotels in town, all of them full (Jack _was_ impressed with her google skills, let’s be honest here). The car was running dangerously low on gas. They pulled into a motel, running on fumes and with 5 feet of visibility. They only had one room. Double beds, at least? Yeah, double beds.
“Is this ok with you?” asked Jack
Cheryl had been surprisingly chipper throughout this whole ordeal. “I mean, beats sleeping in the car!”
“At least they have a bar” said Jack. “Wait, are you old enough to drink?”
“Yeah, I’m old enough to drink”
“My treat then”
The steak was rubbery but he was famished. The fried fish was surprisingly good. They started with a beer and ended up with old fashioneds. Perhaps it was the alcohol, but they got along shockingly well for being…well, 20 years apart in age.
Despite Gen-Z’s reputation as self-obsessed narcissistic jerks, Cheryll was smart, sweet, and mischievous. She teased Jack in a way that nobody in his circle did anymore. He was smitten.
Jack, on the other hand, was educated and sophisitcated and intelligent and wordly and such a gentlemand and _so_ fucking handsome. She was crushing.
“…well, at least we don’t spend all our time on our phones” he said to her, when she had teased him by asking if he had increased the font size on his iphone. “Who _are_ you messaging anyway?”
Cheryl showed him. Instagram, snapchat, tinder, bumble.
“How many people are you messaging?” he asked
“Idk. a lot.”
“Show me”
Cheryl opened up bumble and flicked through, no exaggerating, dozens and dozens of open conversations.
“And how many of those guys do you actually meet up with?” He took a gulp of his old fashioned.
Cheryl, despite herself, blushed. “A few”
“I have so many questions…” he said (to himself? to her? to nobody?)
Maybe it was the fact that she was a lightweight and was 3 old fashioneds deep; maybe it was her personality, she had always been a troublemaker: “before you ask, the answer to any reasonable request is ‘yes'” she said.
Jack had noticed the sign with those exact words in the motel office. _goddamn. Not only was she flirty, she was also clever._
There is a moment during every date when a girl says to herself “yeah, I’m gonna kiss/suck/fuck this guy.” The truth is that for Cheryl that was about two old fashioneds ago, fuck maybe it had even been during the drive—but it had been an empty thought, because, no way would he ever make a move. That was part of the reason why she had even placed him in the “yeah, I’d fuck him” bucket.
***
When they got to the room two things happened:
1. They realized it was not two full sized beds, but rather one queen sized one
2. “of fucking course” said Jack, laughing
3. Cheryll lunged at him, and their clothes started coming off immediately.
Cheryl was… surprised with Jack’s body. Yeah, he was handsome, very handsome even, but she had always suspected he’d have some sort of dad bod under his slacks and button down. But no, he was…strong. Lean.
(Years later Cheryl would learn to recognize that as the body of a 40-something triathlete, a man who had gotten to a point in life where the only way to project _status_ was no longer money, but discipline and time. His hobbies projected “yes, of course I have a 10 thousand dollar bicycle, and yes, of course, I have the discipline to train for an iron man, but what you should _really_ be impressed by is the _time_ I have to spare”.)
His body was strong, but it was also… big. Wide. Cheryl had seen plenty of bare chests, plenty of six pack abs but… there was something fucking _manly_ about Jack’s wide, strong body, tanned, hairy, weathered. Ugh. Manly. Cheryl felt her kegels tighten as she ran her fingers down his chest, his belly button, his sides.
As for Jack… he wasn’t _surprised_ about Cheryll’s body. He remembered what a 22 year old looked like. But he was, entirely, completely, totally, utterly… delighted? no, delighted is the wrong word. He held her thin, tight waist between his hands and felt a visceral pleasure. It’s sexist to compare women to food but that was the kind of experience he felt: like looking at a perfectly plated dish at a three michelin star restaurant. Like that sushi in Kyoto 3 years ago.
But no, it was more than that. Because it wasn’t just her body, her face, her skin without a single wrinkle, her green eyes, her dirty blonde hair: it was everything around them: the motel room, the alcohol on their breath, the blizzard outside, the fucking _context_. Life, he had learned, was about context. And contrast. And as he contrasted her strong lean legs to his dark hand he knew this night would be fucking memorable.
### She did everything to him.
She was obsessed with him, actually. Her hair draped over her head as she took his big, wide cock in her mouth. The men—who let’s face it, now seemed like boys—she had sucked before had always been…theatrical. Like, what was turning them on was her mouth yes, but also the fact that they were “getting a blowjob.” But Jake was different. He was letting her take the reins, letting her suck him, letting her pleasure him. _Service_ him. His moans were controlled, and deep, and real. There was zero acting. And she fucking loved that. She felt submissive but empowered, but most of all she felt like what was turning him on was _her_. Her self, her lips, her tongue. Not some idea of her, not fantasy about a one night stand. She felt so fucking present and _there_.
And when he fucked her… god, that was different too. He _placed_ her on her hands and knees, and got behind her, and…. enjoyed her. Every one of his movements was deliberate. He moved to explore her, to enjoy her, savoring her. Metaphorically rolling her around in his mouth with every thrust, feeling every flavor.
All he cared about was enjoying her. He didn’t care about cumming. He didn’t care about making her cum. Which is why she did. So fucking hard. It just happened to her, unexpectedly. Her orgasm crashed into her like a wave as he penetrated her from behind, as his strong fingers dug into her sides. She moaned, she screamed, she quivered as she came, and she felt his fingers tigthen and he moaned an almost imperceptible “oh my god” as he plowed into her. Each thrust slow but hard, his balls slapping into her, her ass ramming into his crotch, the sounds of skin smashing and slapping.
His demeanor changed after she came. He got a bit rougher. He grabbed her shoulder lenght blonde hair in his hand and yanked her hair back as he fucked her. His thrusts became slower and slower, until they happened almost one second apart, but got were they _hard_. Each thrust slammed the headboard into the wall. Each thrust pushed her entire body half an inch, her knees and palms rubbing against the sheets.
She took six or seven of those thrusts almost silently, exhaling sharply with each, but by the tenth she was moaning, and by the twelfth she was screaming out with every thrust:
_thrust_
OH
_thrust_
MY
_thrust_
GOD!
_thrust_
OH
_thrust_
MY
_thrust_
GOD!
### She let him do everything to her.
Jack manhandled her. He grabbed and squeezed and pushed and pulled and stretched her. She felt like meat between his hands. He grunted and moaned and exhaled. He flipped her over and fucked her. From behind, on top, from the side. His hands grabbed the insides of the thighs, her neck, her shoulders, her hair, her cheeks, her face. His fingers over her ears, her eyelids, the inside of her cheeks. He felt _heavy_. Strong. Manly.
They did so many things, she came so many times that you’d think they fucked all night, but it was, at best, an hour. Her body was coated in sweat and her orgasms had reduced her to a 22-year old mannequin, quivering, spent on the mattress. She was on her side, he was behind her, his big dick pushing into her from behind, his hand on her leg, when he finally pulled out of her and exploded, his cum landing on her ass and her hip bone, dripping down to her crotch.
***
They showered. They talked for a bit. It was incredible. They fell asleep.
***
The drive to Chicago was uneventful. They left early in the morning to beat traffic, and drove mostly in silence. It was like they didn’t want to acknowledge the night before, but not out of shame…out of a sence of, dare I say it, _holiness_. They both grinned the entire time there, and she gave him the gentles, sweetest kiss on the cheek when he dropped her off in front of her north side apartment.
“I loved meeting you” she said.
“Enjoy your life” he answered, and he meant it.
***
### Epliogue?
Jake walked between the glass offices on the top floor of Big Consulting Co. He wasn’t the CEO, but he was close, and he commanded the attention given to a leader that is utterly respected and admired. He smiled, holding his latte, thinking about something strategic, no doubt.
“Jack-o! ” said his colleague Mike as Jack walked into his office.
“Ready for the presentation later?”
“You got it Mike” said Jack, all confidence.
“By the way, I want you to meet my new intern. She just graduated from northwestern.”
“Oh, nice” said Jack. He never had interns. He thought they were a waste of time.
“Cheryl, come meet the legend!” said Mike into the conference room next door.
Source: reddit.com/r/eroticliterature/comments/tafuhy/missed_flight_leads_to_motel_sex_mf_age_gap
!updateme