Kenny Wright
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Holly (short story)
🕑 Added 2024-08-09 13:00:15 +0000 UTC
Alright, In Too Deep 3 is still cooking, but it's coming along really well now. I'm writing the seventh chapter of it now, but it's looking like it'll be longer than the other two parts. I'm really hesitant to start publishing any of the chapters until I have it all written, though, because I so frequently go back and re-write stuff in earlier chapters as I adjust thing down the line.
But I didn't want to leave you all without something fun going into the weekend, so I figured I'd share a story I threw together a while back, with a familiar face. Enjoy!
“Sorry, sorry.” The guy beside Holly definitely was too big for these Economy seats. He was too wide, and his legs were too long. He shifted, his bulk pressing her further against her window spot with a final, “Sorry.”
Holly turned to look out the window of the airplane. Service vehicles zipped around, making preparations for their flight. Somewhere out at the terminal, her best friend, Dori, was making her way back to her car. Her final words still echoed in Holly’s ears, ‘If you sit next to a guy, I dare you to flirt with him.’
Glancing at her seatmate, she laughed to herself. Doubt Dori had this guy in mind when she made that dare.
“Excuse me,” she heard someone say to the guy from the aisle. “They were supposed to seat my girlfriend and me on the same row, and obviously didn't.”
That caught Holly’s attention. She looked over, just in time to meet this new guy’s eyes. My God, she thought, now there’s a guy I wouldn’t mind flirting with.
Taking his eyes off of her, this new man looked at her seat companion and said, “Would you mind switching seats with me?"
The seat companion glanced over at Holly, and that’s when she realized that this attractive man was talking about her, as in, she was the girlfriend. Heat sprang to her cheeks as the big guy shrugged. “No problem.”
With that, he squeezed himself out of the seat, nodded at the newcomer, and moved into the row right ahead of her. Her heart fluttered as this new guy slipped into the seat, and while he was tall and brawny, he still took up a whole lot less space. This was going to present just as many problems for her, though.
“Hey,” he said. He leaned close, keeping his voice low so that the guy wouldn’t hear, and said, “I’m AJ. Couldn’t help but notice you were feeling a little cramped.”
“Thanks for that,” she said, “although there’s one small problem with your setup.”
“Yeah?” AJ had dark eyes that matched his dark, closely shorn hair and bronzed skin. “What’s that?”
She held up her left hand, showing him the wedding band there, along with her large engagement diamond. “Married.”
He just smiled at that, and that smile sent a tingling thrill through her. He had nice, white teeth, perfectly straight. She liked a man with good hygiene. “Married women can still have boyfriends.”
“You sound like my friend, Dori.”
“I like this friend. She’s a smart one.”
“I can give you her number.” She used the line as an excuse to check him out more openly—tight, black t-shirt that stretched over his broad chest and shoulders, slim, designer jeans, a tattoo sleeve up his left arm and peeking out on the side of his neck. His ears were pierced. He was the prototypical bad boy, and he was yummy. “I’m sure she’d be thrilled.”
“Now is that any way to treat your boyfriend? Like some piece of meat to be traded around?”
Holly actually giggled. She hadn’t giggled in years. She wasn’t the giggling type, and it mildly annoyed her. “Sorry, didn’t mean to offend. But you… kind of also look like the type who likes being traded around?” She winced slowly as she said it, sinking down into her shoulders and hoping he wasn’t too upset.
AJ just laughed. “Okay, fair. I’d let you trade me to your friend, as long as you were also there.”
“Ha. You’re a lot, AJ.” Too much, even, although for whatever reason, Holly wasn’t completely annoyed by it. After being ignored by her husband, the attention was nice.
He laughed. “Okay, let’s talk less about me. What’s your deal? What do you do?”
“What do you think I do?”
As AJ checked her out, Holly sat up, straightening her back, squaring her shoulders, flicking a stray strand of her long, blond hair over her shoulder. She wore a tailored, white suit with a black blouse. Nothing too alluring, but she thought she looked good.
AJ seemed to approve. “I think you could do anything—”
“Another innuendo?” She arched a brow.
“What? Oh.” He seemed to realize how she’d interpreted that. “No, I didn’t mean it like that. That’s your own dirty mind doing the work there. No, I just meant that a woman like you seems capable of anything.”
Her view of him softened as she saw through a crack in his confident shell. Or maybe that was what she was supposed to see.
“Based on that nice suit, your hair and makeup, I think you’re heading to Dallas for a job interview. People don’t travel like this anymore.”
“Maybe I’m the CEO of my law firm,” she said.
“You wouldn’t be sitting in Economy. But one day, you’ll be up there.” He nodded his head towards the front of the plane. “So you’re interviewing for a law firm.”
“That’s not fair. You cheated.” Cheated. As she said the word, an illicit thrill shivered up her spine. She quickly composed herself as she felt her eyes drift down to AJ’s broad shoulders and the cords of muscle in his neck. She met his eyes. “I gave it away.”
“Not my fault you volunteered it. It was my second guess, anyway, so I was close.”
“What was your first?”
“Model.”
“Oh, please.” It was a line, but it was working on her. She turned it back on him. “That’s actually my second guess for you.”
“Oh yeah?” They were smiling together. “And what’s your first guess?”
“Dancer at a male revue.” She couldn’t keep a straight face, though, and broke into a laugh. AJ laughed with her.
“Amazing,” he said. “It’s actually true.”
“Wait, really?” Her eyes went wide. She covered her mouth.
“No, not really. But I’m flattered you think I could do that. No, I’m just a boring old personal trainer.”
Yeah, she thought, that tracked. “Old? How old are you, anyway?”
“Thirty-one.”
Jesus. He was almost ten years younger than her. She felt like she was robbing the cradle… not that she was going to do anything here. This was just friendly flirting. This was just what she needed to boost her confidence, as Dori had suggested.
“Hmm… you’re not old, and something tells me that you’re not boring.” She tapped her lips with her index finger. “No, you’re definitely a dancer.”
“I’ll take it. I’ve been called worse.” As the pilot announced that they were cleared for takeoff, he added, “And I like the idea of you thinking of me in a banana hammock.”
She hadn’t until he’d said it, but couldn’t shake the image after. It was such an outrageous idea that it helped her not take this guy seriously, which meant she inevitably lowered her guard.
They chatted the whole flight about a wide range of subjects—none of which has to do with her marriage or husband. It was conspicuous enough that it had to be intentional. AJ was good, and was definitely making a play for her pants. He wasn’t pushy about it, and after the initial banter, he didn’t come on any stronger than most guys who hit on her.
Maybe that was why she kept thinking about Dori’s advice—‘You need to get laid, girl.’
Hank, her husband, wasn’t doing it for her. They rarely had sex anymore. They rarely had anything anymore. Some wives complained about their spouses turning into roommates, but Holly didn't even have that. When they got married, Hank had asked her to quit her job and move with him to pursue his career. Then he threw everything into that career. She barely saw him anymore, and when she did, he was tired and irritable.
AJ seemed to know something was up though. She wouldn’t be interviewing for a job in another city. He didn’t ask, though, probably knowing that details about the job could lead to a buzz-killer conversation about her marriage. She was thankful for it.
He only brought it up once, as they were landing. “You go straight from here to your interview? Or to your hotel?”
Just hearing this sexy man say the word ‘hotel’ almost made her want to blush. She’d spent a non-zero amount of time imagining how good his pecs looked beneath that tight t-shirt.
“Hotel first—briefly—then on to the interview.” She knew where his mind was. “Look, AJ, thank you for earlier…” She glanced at her original seat mate, a few rows ahead. “And thank you for the conversation. It’s helped this old lady pass the time—”
“Don’t worry about it. I was mostly trying to keep your mind off of the interview.”
Whether that was true or not, it had worked, Holly had to admit. “I’m sure.”
“But how about this,” he pressed. “I’ll be at this rooftop bar downtown, Starlight Lounge. Come meet me after your interview. I’ll buy you a drink in celebration.”
“Oh, no, I don’t think that would be a good idea.”
“And here I was thinking it was the best idea that I’ve had this flight, beyond switching with that guy.”
I’m married. That’s what she should have said, the words perched on the tip of her tongue. But she’d already told him that. He already knew, yet still he asked.
“You don’t have to decide now. You don’t even have to decide before we land and go our separate ways. I’ll be at Starlight. Come by if you want. Or don’t. Seriously, no pressure at all…
***
It was her first interview in a few years, and she had been nervous going in. All those feelings of insecurity and doubt didn’t help. The fact that she hadn’t told Hank that she was looking for work in another city added another layer of complexity. She was a mess getting on that plane.
Getting off, she was transformed, and AJ was almost completely responsible for that. As she stood before the mirror of her hotel room, freshening up her makeup, she saw herself as the hot stuff that she once was. High cheekbones and long, honey blond hair thanks to her Scandinavian mother, green eyes and a pale dusting of freckles thanks to her Irish father, she looked good and felt even better. She’d finished at the top of her class in law school. She’d been on track for partner before quitting. She had this, and later, she could have a guy named AJ, which probably wasn’t his real name but who cares. He was hot.
Holly crushed the interview. She owned the room, and everyone on the panel was eating out of her hand by the time she snapped her folio shut.
“We’ll be in touch next week with next steps,” they’d said, but Holly knew she nailed it.
Honestly, she hadn’t thought this far ahead. She’d taken the interview as a lark, encouraged by Dori, who sensed her malaise. First it was just the thrill of putting her resume into the hat. Then the phone interview. Now this in-person one. She knew what it meant to take the job. She knew Hank wouldn’t approve.
As she stepped into the street and hailed a taxi, she was ready for the next step.
“Where to?” the cabbie asked.
But first, it was time to celebrate.
“Do you know where Starlight Lounge is?”
“Of course.”
“Take me there, please.”
***
Holly didn’t think that he’d still be there. The interview has been long, almost three hours. The sun was beginning to set the time she got out of the cab. Someone pointed her towards the elevators that led up to the lounge, which was indeed on the top floor.
Her stomach dropped as the elevator climbed rapidly through the floors. She knew why she was here. She knew what came next.
The doors opened to a wall of bass and breathy, female vocals. The lights were low, a bank of windows beyond showing an orange and purple skyscape. It turned everyone into silhouettes until her eyes adjusted. She hadn’t been in a place like this since she was single, when she’d go out in a tiny dress, looking for some fun, evening entertainment. She didn’t think she missed that feeling of anticipation. Now, her body hummed with the sensual lounge tunes.
The clientele was closer to her age now. Some seemed like they were just from work, still dressed in their suits. Others looked to be on dates. She didn’t feel terribly out of place in her pencil skirt and white blazer. This was a professional crowd.
She scanned the scene for AJ—a man who was only meeting her to hook up with her. The thrill of that was real. She half-hoped that he wasn’t there. It would save her. Mostly, though, she was looking for an excuse to do something naughty and secret.
Holly found him at the bar, sitting on a stool, talking to the bartender. He looked just as sexy here—same dark t-shirt that accentuated his musculature, same tough-guy hair and easy smile.
The bartender spotted her first as she floated over to them. He said something, nodding in her direction to AJ. Holly’s blood pressure spiked. She was quickly barreling past the point of no return.
AJ turned to her, and she nearly melted. God, he was so hot.
The bartender tapped the bar with his fist softly a couple times as AJ said something she barely couldn’t hear. AJ stood and offered her his seat, even though the ones beside him were empty. “Holly, glad you came.”
“I heard this was a great place to unwind.”
“Sure is,” the bartender said. “What’ll you have?”
“I’ll take a Chardonnay, please.”
“Coming right up.”
He moved down the bar, giving her and AJ space to reunite. “How did the interview go?”
“I crushed it.” Remembering how well it went sent a surge of adrenaline through her already soaring bloodstream. She felt entitled to being reckless tonight, and AJ with his shoulders and thick arms were exactly what she needed. “They say they need a week, but I’m pretty sure some wanted to give me the job on the spot.”
“Well, shit, that’s fucking awesome. Congrats!”
She was all smiles. “You’re just saying that because it means I’ll be in this city more.”
“That is a bonus that had crossed my mind.” He leaned in. “Not that I want to assume anything here with that ring on.”
Now it was okay to mention her marriage. She’d met up with him at a bar. They both were past all illusions. Feeling bold, she decided to make things crystal clear. Meeting his eyes with a coy smile, she held up her hands and plucked her rings off, slipping them into her purse. She trembled as she did it. The rush felt like a mini-orgasm.
“Problem solved.”
The bartender arrived with her glass of wine. “Thanks,” AJ said. He didn’t take his eyes off of Holly. “Why don’t you close us out.”
Holly tore her eyes from AJ’s to look at the bartender, who watched the two knowingly. She immediately went bright red.
“You got it, AJ.”
Holly took her glass of white and gulped down half the glass. The chill wine felt refreshing on her tongue. AJ picked up his own beer and finished it off. She was happy to see that his own hands shook a little, too, ready for what came next.
“So where are you staying?” he asked.
“At the W, just a few blocks away, actually.” She took a calming breath. “Want to walk me home?”
***
Keeping her shit together as they walked through the warm, evening air was hard enough. She loved being in the city. Felt so different from her life now. Felt exciting. The smells were different. There was electricity everywhere.
When they got to the hotel, she wondered if everyone knew what was going on. Did they see the hot blonde in the business suit with an equally attractive—but definitely not professional looking—man at her side, and know they were about to fuck? Did they know that she was about to cheat?
With a thrill, she hoped that they did. So much so that she threaded her hand into his as they moved towards the elevators, and squeezed. So much so that when the doors to the elevator closed, she pulled him close and kissed him.
She’d imagined kissing other men since she got married, and over the years, as things deteriorated, those thoughts had turned into fantasies. This kiss was better than anything in her wildest imagination, though—to feel a strange and new man’s lips on hers, to feel his tongue push into her mouth, to feel his hands on her body. She didn’t want it to end, but inevitably the doors opened.
“This way,” she pulled him towards her room, ready for more. Needing more. Glancing back at AJ, she had to laugh. It was like she was a kid again, getting a new toy and so fucking eager to play with it. This fucking stud was all hers.
They were kissing once again as they entered the room, the urgency still there, the desperation even stronger. She kept waiting to wake up, or the fire alarm to go off, or her husband to call and ask her what the hell was she doing.
None of that happened, and next thing she knew, she was helping AJ pull his t-shirt off and gasping at how ripped he was. She didn’t think men like this actually existed outside of internet porn. She could see his tattoo more clearly now—a dragon on his left shoulder that extended down into a sleeve of scales and swirls. She didn’t normally go in for tattoos, but he was sexy as hell.
She kissed his chest, just to see that he was every bit as chiseled as her eyes made it seem. She needed more.
“Take it out,” she said from her knees, clawing at his jeans.
AJ didn’t need any more encouragement. The sound of his belt clasp clinking was so deliciously wrong. She was short of breath as she grabbed his jeans and yanked them down. His cock caught on his boxer-briefs, already hard, already thick, before springing free. He was fucking huge, his skin the same olive complexion as the rest of his body, cock completely shaved.
“Fuuuck,” he groaned as she wrapped her hand around the base and sucked him into her mouth. She knew how this looked to him—blond professional, still fully dressed in her interview suit, on her knees, servicing him. She made sure that her hair wasn’t obstructing the view, relaxed her throat, and took him as deep as she could manage.
She choked a little as he entered her throat. She suppressed her gag reflex, pulled back to get some more air, and went right back in. It felt empowering and naughty all at once. She hadn’t choked on a dick since long before Hank, who wasn’t even as close to AJ’s size. Oh, how she’d missed this.
“Damn, Baby,” he huffed. “Fucking day-um!” He rocked his head back, staring up at the ceiling. It only encouraged her to blow him faster, harder, deeper. She knew she was good, but she was rusty. With AJ, she was inspired.
With spit drooling down her chin and both hands pumping along that thick shaft, she knew he was close. All it took was to dip his hand lower, to find those shaved balls, to tug.
His come filled her mouth, hot, viscous, salty. She drank it all down, swallowing it the way that she used to, the way that a guy like AJ would want her to. To her surprise, her body quaked as she did, like an orgasm, only not—a precursor to what was to come.
AJ didn’t go fully soft, but he wasn’t ready to go right away. Instead, he lifted her to her feet and kissed her hard, not seeming to mind that taste of himself there. “You’re wearing way too many clothes.”
He popped open the buttons of her black blouse as she shrugged out of the jacket. Beneath, she wore a black bra—lacy, delicate, expensive. She liked to wear sexy things beneath her clothing. She liked having that secret, especially when she was in a room full of professionals.
AJ could now be just another one of those secrets.
Her skirt followed with a quick zip down her hip. She enjoyed the way his eyes lit up when he discovered her garter belt and thong, all of which matched the bra. Her nude colored stockings were topped with a wide band of lace.
“Fuck, Babe,” he groaned. A second later, he was all over her again, kissing her neck, exploring her soft skin with his big hands. How did even those feel powerful? When he picked her up by the ass, she felt like a feather. He set her on the edge of the hotel room’s desk and popped open her bra.
She had perky, small breasts that sat firm and high on her chest, with long, puckered nipples that AJ feasted on. She ran her fingers over his head, marveling at how soft his shortly cropped hair was, at how different that felt from her husband’s own, thinning scalp. Her fingernails dug into him in her need. AJ hissed at the pain, pulling back and staring up at her.
“Feisty,” he groaned.
“You bring it out in me.”
“I like it.” He swooped in again, nippling at the corner of her jaw as his hands pinched her left nipple. He squeezed, drawing out her own hiss. “Tell me what you really want.”
“I want…” Her stomach squirmed. But she wasn’t going to stop now. Curling her fingers around his cock, she said, “I want you to fuck me.”
“Take off your panties.”
His order was thrilling. Hooking her thumbs into the sides of her thong, she lifted her butt off the desk as she peeled them down, thankful that she’d put them on over the garter belt—just as she always did, just in case.
Meanwhile, AJ had produced a condom. He ripped it open, the smell of spermicide almost an aphrodisiac to her single days. She spread her legs for him, giving him a clear view of her bald mound.
“Very sexy,” AJ said, running her thumb along her smooth gash. “I like it when the present is just as exciting as the wrapping.”
She watched him roll the condom on, knowing that the last opportunity to stop this was now. She’d gone right up to the line. What she’d done was bad, but she could still fool herself into claiming that she hadn’t cheated. Once she felt that monster inside her, she wouldn’t even have that.
AJ knew it, too, giving her that final out. Rubbing his sheathed dick along her clit, teasing her with the fat crown of his dick, he said, “You really want this?”
She didn’t hesitate. She grabbed him by the back of the neck, pulled him close and kissed him hard. “Do it. Fuck my married pussy.”
It wasn’t something she’d ever thought she’d say. AJ didn’t seem to expect it, either, his nostrils flaring, his brows going up. Then the grin came. Then, the pressure between her legs as he lined up.
She felt a bead of sweat roll off of her temple. She felt her teeth sink into her lower lip. She gave him a sharp, short nod.
“Oh, fuck!” He felt huge, entering her, stretching her, splitting her open. Huge in a good way. Huge in a really fucking good way! “Jesus, you’re big!”
AJ grunted. “And you feel a fuckin’ velvet vice!”
Holly clutched the edge of the desk, holding on until her knuckles turned white. She had to force herself to keep breathing. Stars danced behind her eyelids. “Uhhh, fuck!”
It wasn’t just that this man had a big dick. That would have been satisfying enough. It was that he knew what he was doing, every movement, every thrust, designed to drive pleasure through her core. She was coming before she realized what it was, clenching her teeth and fighting for air through her flaring nostrils.
He wasn’t done. They were so far from done. She clung to him as he picked her up and moved her to the bed. She felt delirious, her pussy throbbing around all those thick inches of pure manliness.
He fucked her for the next hour, a feat that Holly wouldn’t have thought possible. No man had that kind of stamina, and she was pretty sure she’d be too sore to last. But fuck, it passed in the blink of an eye—and half a dozen orgasms. It wasn’t just how hot this guy was, or how good he was with his cock.
‘You need to get laid, girl,” Dori had said. ‘You need some hot, illicit sex.’
This certainly fit the bill.
“You’re going to ruin me for all other men,” she laughed later on, as they lay in bed. She had a craving for a cigarette for the first time in a decade.
“I hope so.” He looked good naked, lying on his side. He even had tone in his hips.
Holly was going to fuck him again, and not just tonight. Her marriage would hang on for a little longer, but they were on borrowed time now—had been for years. She thought she’d be sad about the realization, or annoyed that Dori had been right all along. Instead, she felt free.
She reached for his cock, which had never gone fully soft, much to her amazement.
“I think I’m ready to be ruined again.”
AJ rolled onto his back, dick in hand. “Climb on board.”
She giggled and did as instructed.
Comments
D375
It's good to see AJ again!
Tim Ross
Not a sexy story, nor an erotic story. Just a sad story with some sex. You can do so much better.
@hebridesdrifter
As per usual, well crafted and well presented, but an aberration. Not a hotwife story, not even a cheating one, really, but a woman emerging from her chrysalis to take flight in a new landscape. I’m not an AJ fan, and, for me, the match just never got lit on this one.
Andrew Mellein
Good to see AJ back and up to his old tricks.
Donkatsu
Wait until she tells hubby: "Honey, I'm going to Dallas for a while to take a temporary gig with this law firm. While I'm there I will fill up my spare time training for a triathlon, so I won't be getting into any trouble."
Andrew Mellein
I love natural platinum blondes. Maybe that's why I gravitated toward Irina in "In Too Deep" (LOL!)
Chris K
Nice 👌
Kevin Goodman
Holly's hot
Rich
Put your hands in the air people, AJ is in the house!! Damn. I do miss the big lug. Got some re-reading to do.
quizkid
"All it took was to dip his hand lower, to find those shaved balls, to tug". Her, maybe?
