Can You Squeeze Me In? Ch. 01

Short and to the point. This is my first submission so please leave gentle feedback. This isn't a bdsm story anyway :D Ladies, I'm especially interested in your thoughts. Should I have presented Courtney differently in any way? Her thoughts, motivations, desires?

Enjoy!

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INTRO

James was certainly a contradiction of a man, Courtney thought to herself in the dark. He had the kind of messed up childhood that you would think would result in an equally messed up adult. He was so quiet and meek around crowds. But there were certainly some things that made James throw off his Jekyll and become Hyde. Just then, a touch on her legs interrupted the darkness of the blindfold that had fueled the introspection of her current situation. How did she end up blindfolded and tied to the bed of a cheap hotel while her lover slowly kissed his way up her left leg, inch by inch?

Courtney could feel his soft hands and long fingers sliding up her leg ahead of his hungry mouth. James passed her knee and his pace slowed, kissing, rubbing, teasing her. Slowly moving up her leg, closer and closer to her exposed womanhood. He kissed the crease where her leg met her hips, inches from her most sensitive spots, his tongue darting out and making a beeline for her clit. She knew his game, now, so she wasn't too disappointed when he suddenly shifted over to her other leg, starting over at her foot.

Tonight was special, though, as it marked the one year anniversary of their affair together. Since they couldn't mark the occasion with the typical exchange of gifts, James apparently had a mind to give her one hell of a night. As he finally reached the top of her right leg, she heard a click followed by the unmistakable buzz of a vibrator. "This is for you," she barely heard him say before he put the gently buzzing tip against her opening. All she wanted to do was grab him by the hair and force his face into her while she humped him. But she couldn't, she was trapped, tied down. Subject to his- "Ohhhh" she moaned as James finally licked the top half of her labia and clit, slowly pushing the vibrator an inch, two inches into her. As the first of many orgasms began to swell, she remembered how they first met a year ago...

PART 1

... Courtney...

Courtney was a mess. And not the kind of mess she longed for, no, but an emotional mess. A physical mess. A sexual mess. Everything was a mess. She knew marriage and kids would be hard but she had hoped that her husband would be hard, too. The captain of her ship, rugged, persistent, and... well, hard. Hard for her, hot for her, pursuing her, helping her through the storm. Instead, they had both fallen off of the boat and seemed to be thrown farther and farther away from each other by the relentless waves of life.

It wasn't a single thing that did it for her. Even now, looking back, she couldn't place her finger on a particular moment. The idea sort of... snuck up on her. Sure, there were plenty of reasons. It had been too long without sex. Too long without feeling the burning desire of a man for her body. Too long without enjoying the time right after sex, simply holding one another close, the aftershocks of their respective climaxes still working through their bodies. Could women have midlife crises? Maybe that was it. Whatever it was, the Friday morning after Thanksgiving was the day she woke up and suddenly knew she was going to do it. She was going to have an affair.

Courtney was going to be discreet about it, of course. She didn't want to blow her family up, she had her kids to think about. After a bit of light reading in the dark corners of the web, she felt confident enough to sign up for the big one, the affair site that everyone knew about but never thought they would be on. Courtney left the house for her daily coffee, parked herself in a distant corner of the neighboring hardware store's parking lot, and started to make an account. She almost chickened out when it asked if she wanted to put a photo up. It was optional, but the idea of being discovered was unnerving. In the end, Courtney settled for a picture of her legs as she sat in the driver's seat of her car. And then she waited.

... James...

It had been thirteen years. Thirteen years of decline, of excuses, of pushing away. His wife simply didn't like sex. It had taken thirteen years to get to this point. He tried to understand, to get her to talk. And all he got were two verbal slaps in the face. One: sex was exciting before they got married because she felt like it was wrong. That was her conservative upbringing, he supposed, which certainly did make for fireworks during their dating years. And two: she actually said out loud that he should just have sex with another woman, and she wouldn't blame him for anything, because she sure wasn't doing it.

James was furious. He was upset, he felt betrayed, he felt unattractive and undesired. What was he supposed to do? This wasn't what he wanted. His wife was an absolute goddess. Even though she was petite at 5'2" she had legs to die for, an absolutely amazing ass that just begged to get pulled down onto his lap, and breasts that were the perfect size. She was smart. They shared many life goals together, especially having children. James wanted her, not some random woman off of the street. But... it had been thirteen years. And his wife was very clear: she was done with sex because they were done having kids. James, on the other hand, was very much not done with sex. Every time he looked at her, he wanted her.

He toyed with the thought of introducing her to something she would see as wrong, to try to punch through her layer of assumed asexuality. Would she consider polyamory? Maybe a full swap in the same room would be dirty enough for her... Or could he get another woman to seduce her? He had always suspected she was at least a little bit bi... Those thoughts ran through his mind for weeks, of his beautiful wife getting nailed by some guy while he plowed the guy's wife. Or of a completely scripted business meeting where his wife would have to entertain a female VIP from work who, in reality, was really just trying to get into his wife's panties... It was great in theory but James didn't know anyone he could propose that kind of debauchery to.

And so that left the hall pass his wife had given him. Eventually, his animal drive to fuck won out. One morning in early winter, he signed up for an account at a popular affair site, leaving basic details but nothing about his... problem. He was surprised to see so many accounts in his area but he suspected most were spam. Some were obvious and easy to avoid and others became clear after a few messages. About half way down, a profile caught his eye. Those are some sexy legs, James thought to himself...

... Courtney...

A few weeks after joining the affair site, Courtney had almost put it out of her mind. None of the messages she had received even dignified a response. If you wanted to call her a cum dumpster, you had to earn it, she thought to herself, rubbing her legs together. She wouldn't mind being a cum dumpster for the right man... Bzzt, bzzt. A new email, but the sound made her think of her vibrator. Opening up the email, she saw it was from the affair site.

James: you caught my eye - good catch! can I please have it back?

Courtney laughed out loud, and then looked around guiltily. Right, no one was home yet. She was feeling flirty so she logged on and started a chat with him.

Courtney: well, okay, but one organ for another

James: that's fair

James: I'd start by touching you with my skin, pulling you close

James: and listen to you breathing against my chest with my ears

James: and then I would whisper in your ear about how beautiful you look

James: and finally I'd kiss you slowly

Courtney: hopefully that wouldn't be "finally"

James: point

James: but eventually I'd run out of organs that are easy to do things with

Courtney: I can think of a few more

James: indeed, but what would you want with my hair?

Courtney: well, I might need something to hold on to

James: you win

Courtney: I like winning

James: I'd make sure you won every time

Courtney: is that a guarantee?

James: or your money back

By this point, Courtney was so engrossed in their wordplay that she hardly noticed the sound of a car door closing. She did notice the kitchen door opening, however, and quickly locked her phone. It took her a second longer to wipe the grin off of her face but she managed. Later, she thought, we'll pick that back up later...

... James...

Later that night, after reading and re-reading their exchange and looking more closely at her profile, James sent a few more messages.

James: so... you live in Cumming? that seems like an appropriately named city, given what we're looking for

It didn't take too long and a reply popped up:

Courtney: yeah, it's kind of an awkward name

James: so what do local politicians say? "Cumming is my first priority" - yeah, I bet it is!

Courtney: maybe I should run for a local office...

James and Courtney talked late into the night with their spouses asleep next to them, uncaring.

... Courtney...

Courtney woke up horny. That wasn't entirely a new thing. But she was also thinking about a particular man and wondering what it would be like to go to sleep with him, to fuck him, and to wake up with him. And then to fuck him again. Yeah, she was horny. She grabbed her phone and shot James a message.

Courtney: I get the feeling that you might be a guy with a big dick

James: yes, actually

Courtney: so, uh, can I see it

James: /pic/

James: it's really turning me on that you want to see it

... James...

James was blown away that anyone would ask for a dick pic. This had to be a dream. He was too used to a complete lack of interest in anything related to sex. Was this how other women acted? What in the world had he been missing out on? Throwing caution to the wind, he leaned in to what she seemed to be wanting and what he had been wanting to do, replying with a small scenario...

James: Imagine us waking up, snuggled close, my dick against the back of your legs. I'd start kissing your neck and running my hands down your side to your hips. You can feel me throbbing against you... You spread your legs a little and grab my dick, slowly jacking me off. I find your pussy and run my fingers up and down it with little circles at the top over your clit.

James: After a minute, you can't wait any longer. You line my dick up against your pussy. I slowly push the head inside you... You feel so good...

James: I keep rubbing your clit as I push in a little deeper, whispering in your ear about how good you feel on my fat dick.

Courtney: oooh, wow. I'm pretty sure I'm wet now. And your dick is huge

Courtney: I feel like I could totally fuck you. Damn.

James: Thanks! I want to fuck you, too.

Courtney: I wasn't expecting how hot it would make me

Courtney: the way you talk about it. Damn.

Courtney: /pic/

James was stunned for a second time when the picture of Courtney popped up, a full frontal, and not a stitch of clothing on.

Courtney: I've got to get ready for work but I wanted to leave you with something to think about

Courtney: I know I'll be thinking about what you wrote all day

Courtney: that and your huge dick

James: wow, you're beautiful. and you're welcome

He was sure he should compliment her more but his brain wasn't entirely working. Here was a beautiful, mature woman who was pursuing him sexually and complimenting his dick. That had never, ever happened before.

James and Courtney continued flirting throughout the day while they were both at work until James noticed something.

James: you know, every time I open this chat I get hard

James: what have you done to me?

Courtney: apparently everything right

James: I would say so!

... Courtney...

Courtney couldn't focus at work. She was half way through her shift and her panties were soaked. The constant flirting was really getting to her and when James said he got hard every time he opened the chat she about lost it. Knowing that fact touched something deep inside her, that at a very primal level James wanted her. His body wanted to fuck her body. And then he sent her this:

James: imagine if I showed up towards the end of your shift... do you think you could squeeze me in?

Courtney: there's a hotel near where I work

Courtney: maybe we could meet there after I get off

James: hey, not without me! but... really? sure! just tell me when and where

Courtney looked at what she wrote, a little surprised she had done it. But something deep down inside her needed this. A part of her had latched on to his interest and it was pulling it closer until she could shove it in her pussy... Fuck, she was so horny. She looked down at the chat and she had somehow typed out the nearest intersection and that she got off work at 4.

James: I'll have a room ready for us

Courtney almost came.

PART 2

James took the afternoon off and booked a room at the specified hotel. He drove over a little early and waited in the parking lot outside his truck in the cool afternoon air. It did nothing to chill the fire burning inside him. He had never felt this alive before. James was lost in horny thoughts when he looked up and there, a few cars over, was Courtney. She was staring at him with an expression somewhere between a deer in the headlights and a lion eyeing its next meal.

All of a sudden Courtney was in his arms. James had a chance to whisper how good it was to see her before the spell broke and her lips found his with force. James put one hand behind Courtney's neck, buried in her hair, while the other found the small of her back and pulled her closer. He could feel her heat, her desire, and it matched his.

Ten minutes later, they were still making out but hands were slipping under clothing and they were moaning loudly without a care in the world about who was around. James couldn't get enough and he knew he needed more, much more. Desperately, he broke the kiss and pulled her to into the hotel lobby towards the elevators. James was sure they must have looked a mess after making out for that long but neither of them cared. As the elevator doors closed, they resumed making out. "I can't get enough of you," James whispered in between kisses. Courtney shoved one of her hands all the way inside his jeans, wrapping it around his dick. As the elevator door opened, she kept it there, pulling him by his dick out of the elevator. She had to let go when she noticed housekeeping down the hall and then they practically ran to their room.

As soon as the door shut, James pulled Courtney's shirt up and off while she expertly undid his jeans. She fell to the floor on her knees along with his pants, his boxer briefs following a second later. Courtney was on a mission to suck that huge dick and nothing was going to stop her now. It sprang free in front of her face, already leaking precum steadily. She grabbed his dick with one hand, his balls with the other, and licked slowly from his balls to the head of his dick. It somehow got a little bit fatter which was impressive as it was already approaching 6 inches around.

Courtney decided to see how much of this sword she could swallow and popped the head in her mouth, giving it a few swirls with her tongue. As she looked up at him, she let her eyes roll back, all the while valiantly attempting to swallow his fat dick. She only made it a few inches but she held his dick as deeply in her mouth as she could manage and moved her tongue back and forth, massaging it with strong swirls. She wrapped her hands around the remainder of James' dick and started to jack him off. He buried his hands in her hair and helped her bob her head back and forth - no, he was fucking her face. Her eyes rolled back again as the thought buried itself in her mind. He wanted her. He needed her. She was his and he was hers. This is what she wanted, what she needed. She was a sexual creature and that part of her had withered for years. Now, with his dick in her mouth and his precum dripping down her throat like an elixir, that part of her was springing back to life.

Courtney popped her mouth off of his dick and stood up. It was time. Breathing heavily, she pushed her skin-tight pants off, taking her panties with them. He had pulled his shirt off somewhere during the blowjob and now they were both naked, staring at each other. James' dick was dripping precum and spit, pointed at her like a magnet. And, just like magnets, they found each other pulled relentlessly together until they met, arms wrapping around bare backs, her breasts mashed against his chest, his dick pressed against her belly.

James and Courtney moved slowly towards the bed, locked in another kiss. As the backs of her knees hit the mattress, her entire being focused on getting that huge dick inside her pussy. They fell backwards on to the bed, with James' face conveniently landing on her breasts. As he sucked her nipple into his mouth and alternated softly licking and gently biting it, one hand grabbed her other breast while the other found her exposed pussy. Covering it entirely with his large hand, he slowly dragged his hand upwards, playing with her pussy lips. As his fingertips finally made the slow journey from her perineum all the way to her clit, they suddenly flicked back and forth for a moment before his hand began to glide back down. James repeated this motion over and over, varying the speed and pressure, as Courtney felt her body give in to his touching. Her hips raised off of the bed, waving in the air. Her nipples got bigger and more sensitive. Her breathing got quicker and quicker, her vision clouded over, and she yelled incoherent noises of assent as her orgasm began to take hold of her body.

It was like an earthquake, a fault line that had built up tension over the course of years, suddenly giving way in the most wonderful way. Courtney's hips slammed back down to the bed, her legs snapped closed, she screamed wordlessly as the shockwaves ricocheted back and forth through her. James pressed his hand against her, moving it in large circles over her entire pussy, as her orgasm continued for ten, twenty, thirty seconds. Finally, her legs fell limply open and Courtney lay there with her eyes closed.

That was easily the best orgasm she had ever had, she thought to herself. But she knew that this was just the beginning, one of many. She opened her eyes, smiling, realizing she had ended her orgasm with her legs spreadeagled. And there was James, staring at her pussy, hungrily, his huge dick pulsing with his desire. For her. Both her smile and her legs spread a little wider.

INTERMISSION: motel 69

There in the dark of the cheap hotel, Courtney had already come twice on the combo of the vibrator and James' tongue. Her legs were in a familiar position and her smile was, if anything, bigger and more genuine. James pulled off the blindfold and restraints. She welcomed him into her arms, face to face. She welcomed him into her legs, wrapping them around his back. She welcomed his dick into her pussy, which was now familiar with his huge circumference spreading her open. They stayed like this, making out for a few minutes. Courtney's pussy was rhythmically pulsing on James' dick, attempting to milk the cum out of him now, right now. But today he wasn't in a hurry. Today was about her.

James rolled them over so they were on their sides, facing each other, Courtney's legs still wrapped around him. He loved this position as he could play with her pussy while slowly fucking her and she loved it, too. James began to slowly piston his dick in and out of her wet tunnel, enjoying the feeling of Courtney using her legs and pussy to try to keep him deep inside of her. Every time he pushed back into her, she let a little moan of approval slip out between their kissing. Sure enough, James' hand found her pussy lips and began to trace their outer edges as he continued to slowly fuck her. He kept his pace slow and steady, letting them each enjoy the little feelings that hurried motions sometimes missed: the feeling of his dick sliding almost completely out of her, leaving just the head lodged in her pussy; the feeling of his head popping back inside of her; his hands journeying down her legs to her knees before returning home to her pussy, where they belonged. Their passion built slowly but steadily, their eyes locked together, joining them just as much as they were joined physically.