Late Night Hookup
Copyright© 2023 by Samantha Burnett
Chapter 1
Erotica Sex Story: Chapter 1 - Charlotte wants to live out one of her kinky fantasies, and gets a little bit more than she bargained for.
Caution: This Erotica Sex Story contains strong sexual content, including Fa/Fa Consensual Reluctant Lesbian Fiction BDSM DomSub Humiliation Rough Sadistic Spanking Anal Sex Exhibitionism Oral Sex Foot Fetish Leg Fetish Prostitution
Charlotte was 25 years old, and wasn’t ready to settle. In fact, the more she realized that she grew up in a secure bubble of friends, family and relative wealth, the more she grew curious about what was outside the bubble. More and more she felt the urge to explore her inner desires, as they became clearer with age.
She grew up in a somewhat conservative, well off environment. Religion played a role, and although not a heavy one, there were certainly taboos when it came to sexuality. You didn’t talk about porn, clothing that was anywhere near promiscuous was frowned upon, and although being gay was tolerated for people on the outside, coming out of the closet was a pretty big deal.
Yet, Charlotte started having fantasies about lesbian sex more than once in her late teens. She never told anyone, but she came pretty hard to those fantasies once in a while since she became more sexually aware.
During her college years, her life was mostly occupied by studying, parties and boyfriends. The intimidatingly pretty, tall blonde was very popular by students and teachers alike, and finding a job after getting her degree proved not to be difficult at all. Her father had connections here and there, and soon enough, she became a junior executive at an accounting firm.
But despite her success, her mostly struggle free path to adolescence and her downtown spacious apartment just outside of the crowded areas, more and more often she experienced cravings for more intense things. Things that would be considered wrong on many levels by her friends and family. But still, they were there.
A few months ago, Charlotte was drinking cocktails with a friend of hers, and got into a pseudo philosophical discussion about how life is about taking chances, about failing and learning, and that all these chances shouldn’t be stopped by any limitations, taboos or feelings of guilt imposed upon you somewhere in life. And even though Charlotte didn’t remember all the details, and had a heavy hangover the next morning, bits and pieces of that conversation stuck with her. She wanted to take more chances.
Fast forward a month, and Charlotte found herself browsing kink websites more than she had done before, reading through specific ads on kink dating websites, even looking at some fetish porn, all the while growing more convinced that she should let go of her inhibitions to be able to actually live out her fantasies. Of course, no one had to know, as she formed her idea about what she wanted to experience and how.
She had planned everything. The online store where she’d buy her clothes, this app called ‘F4F’ that she would use, even the date on which she’d try and have a bit of an adventure. Picking a date would help her not to postpone or bail out eventually, she figured.
When she came home from work the week before, the packages she ordered the other day were dropped in front of her apartment door. All wrapped discreetly, but she knew exactly what was in them. She hurried to get the boxes inside, and her fingers trembled slightly as she opened them. There it was. The outfit that she was going to wear on her adventure night.
She closed the curtains before proceeding to undress herself as fast as she could, but slowed down as she put her feet into the thin, fine black stockings, not wanting to rip them. Putting on the small, black, sexy garter belt felt odd. She had imagined wearing it before, but actually wearing it make her feel sexy in a way she had never felt before. As if it somehow emphasized nudity. As if these clothes were an accessory rather than meant to be covering her. Clipping the straps from the belt to the stockings took some effort, but finally that part was in place too.
The very thin, small and low cut black thong followed, just barely covering the trimmed line between her legs. It was exposing even more skin than she had imagined. The bra, which she had worried about most in terms of quality, appeared to fit nicely, and as expected, showed a lot of cleavage. Of course, none of it was high quality. It was made to provoke, and she already started to feel aroused when looking down at what she was now wearing.
When she got the dress out of its box, she smiled slightly as she held it up. “Oh god,” she sighed in disbelief. It was that short. A slut dress.
She put it on, and indeed, it only reached just over her pretty, round butt, completely exposing her slim, beautiful legs, and the top of her sexy stockings, leaving a fair bit of naked white skin between the stockings and the hem of the dress.
Then finally, to finish the look she was after, she put on the heels that she bought to go with the outfit. She had made sure to order shoes that looked at least a bit classy still, although now, looking at the platform sole under the 5 inch heels, they didn’t seem as classy as they looked when she browsed the online lingerie catalog. In fact, they wouldn’t look unusual on a stripper at all.
When finally she stood up, and carefully, on the highest shoes she now owned, walked towards the mirror in her bedroom, she was shocked at her transformation. The outfit, and with it her whole appearance, looked much more slutty than she had thought. The dress shorter than it seemed in the pictures, the stockings having an even bigger ‘hooker’ effect than she had thought, and the heels, well, they just left no doubt about what she was dressed for.
But at the same time, she thought of the image of what she wanted to experience. Didn’t this fit right in? Didn’t this make her seem as if she really tried? Didn’t this make her look exactly like the women she saw in the pictures in all those kinky profiles online? Or even in some of the porn clips she had watched?
She imagined herself being dressed like that in someone’s home, and being watched wearing it. She turned in front of the mirror, and sure enough, her round, perfect ass was accentuated in a way that it never was before. She could hardly believe it was really her she was looking at in the mirror. She could easily pass as some kind of stripper or beyond, wearing this. Just like the people on that kink website, proudly posting selfies of them wearing fetish clothes. Not that that was something Charlotte would ever do.
Being caught up in her imagination, just for fun, she gave a small slap on her cheek, which, to her surprise, sounded almost as if it was a slap against her bare flesh, through the thin, cheap fabric of the dress. She did it again, while her body started to heat up immensely. Even now she was afraid the neighbors might hear. In her paranoid mind, they’d hear exactly what kind of a perverted thing she was doing here, and they’d know exactly how she was dressed. Of course they couldn’t hear that, she told herself.
She had to remind herself again that being able to let go of her inhibitions was one of her goals. Taking risks. To not be limited by what she was conditioned to think. It made complete sense.
Again she slapped herself on her butt, through the dress, imagining it was this specific woman from one of her fantasies doing it. An imaginary woman, still.
“Bad girl,” she whispered to herself, and imagined the imaginary woman saying it.
By then, she couldn’t help herself anymore, and reached down, easily lifted the slutty, very short dress, and shoved her fingers right into the tiny thong. Masturbating like this was not easy, on those crazy high shoes. But it had to happen, she didn’t care. She was too aroused. She stepped closer to the mirror, and supporting herself with one hand against the mirror, she started to masturbate furiously, keeping her legs straight, a position as if she was being spanked. Living out her fantasy without anything actually happening, with her face flushed.
She came hard, with her body heated up so hard that she was sweating, and her knees became weak while she came with a loud squirm. She felt a strange mix of embarrassment and adrenaline when she managed to walk to her bed, and took the high heels off. What was she doing? This wasn’t good girl Charlotte. Now she had a real secret. The secret of a very intense awareness that she loved this. Of course, she wouldn’t share what she just did with anyone. But more importantly, she would not talk about what she was going to do with anyone.
The days following, she tried not to think about what she was going to do too much, if only to not scare herself further up to a point where she wouldn’t go through with it. She wanted to do it. She was going to do it, period. But making the pondering stop was quite difficult.
Monday evening arrived. Outside, the rain drizzled down on the streets as she arrived home from work. It was a regular, gray night like many around that time of the year. But for Charlotte, it was going to be a very different night.
Determined to set her plan in motion, she took a shower after a light meal, and groomed herself more thoroughly than ever before. Her skin smooth everywhere, with the exception of her carefully trimmed pussy. Her long, blonde wavy hair done beautifully after dressing herself for the second time in that ridiculously sexy outfit she wore a few days ago. The tingles in her tummy already started to appear when she looked at herself in the bathroom mirror while brushing her hair, and she fought hard to get rid of all the doubts that were on her mind.
Taking her phone into the bathroom felt downright wrong. Assuming a sexy pose while facing the mirror and snapping a picture with her free hand running through her long blonde hair, and another one while she turned her back to the mirror and slightly pushing her ass out was something she had never imagined herself doing. She used to even judge girls who put pictures like that online. But she didn’t hesitate, even though her hands trembled as she then created the profile on the F4F app that she just installed.
She pretty much memorized the profile text she made up over the previous days, and typed it right in. It didn’t leave much to doubt.
“Hey hey, submissive 25F here, blonde, blue eyes, 5’7, 121lb, 38B, looking for kinky stuff, if you’re the type who doesn’t ask but demands ... hit me up. :) Xx”
She slightly modified the pictures she just made on her phone to make sure her face was blurred out, and added them to the profile she just created. The app would then use her geographical data to match her with people around her, and the spinning wheel that was supposed to show that the app was busy searching and matching drove her crazy with adrenaline. The idea that her profile was out there, that her pictures were out there, was so very wild to conservatively raised Charlotte.
She imagined that it would at least take a little while before she would be noticed, but when she checked the profile views in the app about 30 minutes later, she saw that her profile had been seen 120 times already. The idea alone was insane. This whole thing made her feel so exposed. But she promised herself not to be paranoid about this, and told herself that if she would be recognized somehow, that other person would be as guilty as she was.
Her heart skipped a beat when she then saw a pop up message on her phone, from another user of the app called “DommeKath”.
“Mmm, looks good ... looking for hookup tonite?”
She read the message a few more times. Yes, that was exactly what she was looking for, actually. But she had to check this user out first, of course. She had to at least make sure they were on the same page.
DommeKath’s profile was pretty clear.
‘43 powerdomme, mainly into hookups, no endless texting, no drugs, prefer experienced subs. No wishlists.’
Her pictures were somewhat vague and emphasized some of her fetishes rather than her appearance, but it showed enough of her to get an idea. And Charlotte couldn’t help but being intrigued by what she saw. One picture that was taken from the bottom of the woman’s feet, up her stocking clad legs, as if taken from someone on the floor. The next one made Charlotte blush. A closeup of someone’s mouth, with two fingers pushed into it between her lips. She was the real deal. The last one was just her silhouette, photographed in the dark, or photoshopped. It looked mysterious.
She trembled with adrenaline while she then texted back.
“I am... :) Not experienced though, saw that’s what you’re looking for...”
It hardly took more than a few seconds before she received another popup message on her phone. She pressed it, and read the message.
“Ill make an exception for a pretty thing like you. Can train you if you want.”
Charlotte smiled slightly as she was just pondering about what to write back, while she received yet another message.
“Mmm ... obedient little slut?... ;)”
Charlotte blushed deeper than she already did. This woman pushed all the right buttons. So this was really how easy it was to get dates, or hookups, in that world.
“I could be ... heh :)”
For a second Charlotte wasn’t sure whether she should actually press ‘Send’ on that last message, but almost instantly after she did, she received a very clear invitation.
“7521 Grove St. only 3 miles from you, 10:30 good baby?”
Charlotte had noticed the distance indicator on every profile, based on where you were, and she was right. Oh god, this sounded so wrong. But so hot. And very precisely what she was looking for, too. And she wasn’t going to bail out. She had promised it to herself. She was going to do something different. Something that had been on her mind for a long time. And apparently, many people were doing it like this. Based on how quickly she even got so many views and a response, there must be quite a few people. And it sounded playful. ‘Baby’. It even sounded sexy. In this context, anyway.
“10:30 should work ... see you then? :)”
Charlotte waited for a few minutes to get an answer, but nothing came. Then, with a sigh of nervousness, she decided to bite the bullet. She was going to do it.
She stood up from the couch, and put on her knee length gray coat, making her look a lot more covered up compared to wearing just the outfit she was wearing beneath it. But then, pretty much anything would look conservative compared to what she was wearing underneath. She zipped and buttoned up her coat all the way, so the only part of the outfit that was really visible to the average passerby were the high heels and the stockings she was wearing, although it looked as if she could as well be wearing regular pantyhose. Charlotte had to tell herself that no one would know a few times to calm down while standing in front of the dressing mirror in her hallway before leaving the door.
Minutes later, with her bag over her shoulder, she was walking down the street to the subway station near her comfy, downtown apartment. She picked this night and time carefully, as she knew that on Monday evening around this time, the city would be relatively quiet. She was that paranoid about being seen by someone. Getting caught in her dirty little adventure.
She was actually glad about the gray weather, because it was even quieter on the streets because of it. But once she checked in for the subway, and sat down one seat away from an old woman, across a few young guys, her heart started to pound. Being dressed underneath her coat like this with people around her took her out of her adventurous, excited rush, and she really started to panic. She saw them staring literally at her shoes, at her stocking clad lower legs as she sat there. Or at least, she thought she did.
She had to calm herself down by telling herself that it really was nothing out of the ordinary. They didn’t know anything. They didn’t know she was dressed like a complete slut under that modest, gray coat. But she kept worrying. She worried about one of the garter straps detaching by accident, and her stocking would slip down. She worried about the buttons snapping from her coat somehow. She worried about being followed when she would get out after some eight stops, for which she kept a sharp eye on the display above the seats where the young guys were sitting. She avoided all eye contact.
Charlotte sighed with relief when then, two stops before the one where she had to get out, the guys left, but her heart sank as a whole group of guys entered. Visibly drunk, loud guys. Oh god no. Fortunately they stayed near the other entrance. She clenched her hands together, waiting desperately for her stop.
She stood up quickly to leave the subway when it was nearing the stop where she had to get off, and impatiently waited for the doors to open, as she finally heard one of them shout. She had been noticed.
“Hey pretty girl!” No response from Charlotte of course. “Hey! What a bitch...” she heard one of the guys mutter just as the door opened and she got out, her body tense with stress.
She gasped for air as she walked out of the subway station. Getting out dressed like this was a terrible idea. It had seemed like much more fun in her little fantasy.
But in the meantime, she was only a block away from where she had to be. Where this woman was waiting for her. DommeKath.
The neighborhood was certainly not the nicest one. It was very different from the area Charlotte lived. Somewhat poor, not the best reputation, lots of apartment buildings all looking alike. What used to be community housing was slowly being turned into nicer apartments and sold, but that was a very slow process, and the improvements were barely noticeable.
Charlotte felt watched by every person she made eye contact with. It felt as if she clearly stood out in this area. Passing by a supermarket, she swore she saw a woman with a shopping bag looking at her with some sort of disproval in her eyes. She felt slightly paranoid walking there, especially dressed like this. It even seemed as if she was wearing classier clothes than all the people there, at least at first sight. Maybe it was just the shoes, but she once again regretted her choice of wearing this outfit on her way over to the address.
She kept walking as fast as she could, on her very high shoes, which was a dangerous thing to do, but she just wanted to get it over with. Finally, she reached the apartment building on Grove St. Now, she was back in her little game. She pressed the button outside next to number 7521, and waited.
“Hello?” a crystal clear, somewhat low female voice then answered.
“Hi, it’s me,” Charlotte answered, not really knowing what else to say, while her heart was beating faster.
What did people say anyway on these kinky, anonymous dates? She figured this was how these things went. These anonymous, discrete meetings. It took a few nerve wrecking seconds before the buzzer for the door was heard, and she pushed against it to walk in.
She noticed that 7521 was on the second floor, and decided to just walk. She didn’t want to wait for the elevator. Her high heels knocked on the tiled stairs of the apartment building. The interior of the building looked so much cheaper, almost alien, compared to what Charlotte was used to. Tiled, old fashioned floors, red metal stair railings that needed a repaint, and dark gray carpet in the hallways to the apartment doors.
But that was not her focus. Her focus was number 7521, of which the door was slightly opened. She looked at it, as she felt herself becoming nervous, even though her excitement was slowly coming back.
Just as she wanted to peek inside to see whether she had to press the button for the doorbell on the outside despite it being open, the door opened wider.
It was then that she saw her appearance. An Italian looking woman somewhere in her forties, smaller than herself, especially while Charlotte was wearing these shoes. Slightly full figured, although not chubby. She was dressed in quite a short, black skirt, was wearing modest, high heeled pumps, and the white blouse she was wearing was opened just a bit too far, allowing Charlotte to see a lot of cleavage, revealing a bit of her obviously full breasts. Her hair was black, curly, but what really drew Charlotte’s attention were her piercing eyes behind a pair of slightly tinted glasses. They looked somewhat aggressive, even.
“Hi,” Charlotte spoke quietly.
The woman didn’t say anything, but stepped aside quickly, to let her in. Of course, she wanted to be discreet about this too, Charlotte figured.
The light in the hallway of the apartment was bright, and not at all cozy. It was a bit cold, and the woman still hadn’t said a word to her, as she closed the door, and eyed up Charlotte so very obviously.
“You can hang your coat right there...” she then said calmly, without welcoming Charlotte at all, and pointing at the coat rack right behind Charlotte.
Charlotte tried to remain calm and casual, and just nodded, while her legs were trembling from nervousness. The woman had a commanding tone in her voice, even while saying something as simple as that.
“Sure,” she answered with a slight, polite smile, as she started to unbutton her coat, and turned as she took it off.
It took only a second before she could hear the woman’s heels on the floor behind her, quickly approaching her. And just when she slid the coat off her shoulders to take it off and hang it on the coat rack, she felt the woman’s hand on her lower back, but quickly sliding down, over her tightly wrapped butt, over her right cheek, caressing down until her fingers reached the naked skin of her thigh above her stockings, then firmly squeezed her cheek. Not at all gently, and Charlotte tried to adjust herself to the situation. She tried to hang up her coat while the woman was squeezing her cheek, making the very short dress crawl up, as she felt embarrassed about the very seductive, very sexy outfit she was wearing. It wasn’t just sexy, it was downright porn style sexy. Wouldn’t she think it was way too provocative? What if she thought her outfit was ridiculous?
The woman kept squeezing, and Charlotte, while blushing, tried to remain her posture, and just stood there letting the woman fondle her like that. She didn’t know whether that was what the woman intended she’d do, but somehow the woman’s touches felt so insistent that she didn’t feel like she should move. And indeed, the woman kept squeezing, and using her fingers to slowly let the already short dress crawl up more and more, inch by inch revealing the blonde’s perfect, round ass.
“Face me,” she then said simply. Commanding.
Charlotte turned, and blushed deeper, very aware of the fact that this woman was looking at her wearing that very slutty outfit. What would she think of her? That she was some kind of slut who did things like this all the time? Would the woman have certain expectations because of it? But Kath didn’t give her much time to think.
The woman looked up to Charlotte, into her eyes. A strict look. A controlling look. Charlotte could feel it. This woman was very, very controlling. The type you wouldn’t even dare to disagree with.
“Mm...” she only mumbled, as once again, she let her eyes roll over the very pretty, tall blonde in that very seductive outfit in front of her, all along her body.
Kath then took a step forward, and pushed against Charlotte’s shoulder, pinning her to the wall with one hand. Charlotte felt her body quiver, but feeling a very different senstation as Kath then simply reached down with her other hand, and pushed her hand right between her legs. Right under her short dress, which by now didn’t even cover her thong anymore. She squeezed. Gently at first, but slowly increasing pressure, rubbing Charlotte’s clit through the small black thong with the palm of her hand, her fingers under her, pressing against her lips, an almost taunting look on her face as she kept looking into Charlotte’s eyes. Charlotte gulped and closed her eyes, as the woman started to rub her through her panties. Slowly, but firmly. Her body heating up was a very clear sign that she enjoyed it, no matter the extreme tension she was experiencing. Charlotte was already on fire.
Kath let go of Charlotte’s shoulder, but instead used her now free hand to reach around Charlotte’s head, pulling her head towards hers. Charlotte couldn’t do anything but to move with her, and before she knew it, her lips were touching the woman’s lips, who opened her mouth right away, and started to wildly tongue kiss her, while still applying pressure to Charlotte’s pussy.
Charlotte felt herself getting turned on in a weird way, feeling a very unfamiliar mix of taboo and deep arousal. This was how she wanted to be treated. Dirty sex. No sweet romance. No nice words. No silly looks.
But little did she know, this was only the beginning of how dirty this was going to be. Kath ended the kiss as abruptly as she started it, but not letting go of Charlotte’s head.
“Good sluts don’t wear panties, take them off.”
She said it in a low voice, while having Charlotte’s head in that same controlling grip. Just when Charlotte thought she couldn’t possibly blush any deeper, she felt her face get even warmer. It wasn’t a question. It was very clearly a demand. And she agreed to go with all this by coming here.
Giving the woman a meek smile, while she could feel her warm breath on her face, she reached down. Was she going to take off her panties, just like that? Here in this house, after having been here for just a few minutes? But it didn’t seem as if it was a time for arguing.
Charlotte then reached down, and while feeling a deep arousal and embarrassment at the same time, she hooked her thumbs behind the small black thong she was wearing, all the while bent forward a bit, uncomfortably, as the woman was still pulling her down slightly, with Charlotte being about a head taller than the Italian lady.
She felt strangely exposed, as she felt her pussy suddenly unprotected, pulling the thin, skimpy black thong down along her thighs, to her ankles. She carefully stepped out of them, the woman still holding her in this grip, as if she was forced to do it. As if she wanted to let Charlotte feel the control she had over her.
The woman said nothing, but instead reached for Charlotte’s face with her other hand, and pushing her fingers against her lips. Charlotte was too overwhelmed to protest, or to even realize what she was doing, and with a strange, humiliated feeling, she opened her mouth. That turned out to be exactly what the woman expected, as she didn’t hesitate for a second, and pushed two fingers into the naive, inexperienced, unsuspecting, beautiful blonde’s mouth.
“Lick.”
It made Charlotte shiver. She felt like such a slut. She felt so humiliated, being belittled like that. She hadn’t expected it would be as intense, as serious even, as this. This wasn’t soft or playful. This was downright dirty, commanding domination. She had never blushed this deep, as she started to lick this much older woman’s fingers, swirling her tongue around them, actually trying.
“That’s right ... that’s a good slut...” the shorter Italian woman mumbled approvingly, still having her hand around Charlotte’s neck, pushing her face down, while using her other hand to push her fingers into Charlotte’s mouth.
Charlotte couldn’t believe she was actually receiving a compliment for what she was doing. A twisted, humiliating compliment. This was already much kinkier than she expected, licking the fingers of some woman she had never met before.
Finally, after maybe even a minute, the woman withdrew her fingers from Charlotte’s mouth, and let go off her neck. Charlotte thankfully stood up straight again, while the woman now curiously looked between her legs, at Charlotte’s neatly trimmed blonde pussy.
The woman stepped closer to Charlotte, while her hand reached down between her thighs once again. Softly, but with very determined moves, she fondled the inside of Charlotte’s thighs, dangerously close to her now nude pussy, while pressing against her shoulder, to pin her against the wall again, just like she did before. She ran her fingers softly, teasingly along Charlotte’s outer lips. Charlotte had never felt this vulnerable, this naked before.
“You need a lesson so you don’t forget to not wear panties next time...”
It wasn’t a question at all. It was a definite thing, even though Charlotte didn’t know what it meant. But the way the woman emphasized her nakedness, her exposed pussy, by caressing it, turned Charlotte on even more. Her body felt warm, and her face felt warm. The woman could probably even see how she was turned on.
“Turn around, stick out your ass,” the woman then simply said.
It sounded so bold. Crude. So this was how sluts are treated, Charlotte thought, while feeling that strange weakness in her knees again that she felt when standing in front of the mirror a weak ago, while wearing that same outfit, although she was wearing panties still back then. Not now, in front of that stranger.
Charlotte couldn’t believe she was giving in to such embarrassing commands, but she was doing it. The woman hardly seemed impressed by her doing so, as if it was the only way. Charlotte nervously arched her back a bit, in a shy attempt to actually stick out her bare, round butt peeking out from under the dress now at her waist.
Charlotte then felt a firm slap against her bare ass, as she almost jumped.
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