I slept with an inmate’s girlfriend whom I met in college. [MF]

Her name was Stephanie and we met one day on campus, when I approached her while I was waiting for my bus. She was sitting alone, working on some homework, and I couldn’t help but notice how cute she was. We immediately struck a nice conversation.
I’m a 6ft0 black guy and back then I was 19. She was 22, about 5ft3, blonde, a practically what you would call a BBW. Big boobs and big ass, but thin face, and thin torso. Sexy as fuck. I like my BBWs. Lol

We spoke and she told me she had gotten pregnant at 18, by this drugs dealer she met in high school, whom at that point had 6 years left on his sentence. She sounded sad but determined to live and see what else is out there. Her daughter was at a daycare, she was juggling school and jobs, his and her families were not really supportive, and, when we got more personal, she told me she hadn’t fucked in 3 years. I was taken aback cuz this girl was sexy, nice fucking teeth, nice smile, nice voice, beautiful eyes, if I were to rate her, she was easily a 8.

[Group] The Ball That Wasn’t

Hello everyone! I hope your lives of social distancing are going well, and I hope you have some time set aside to read, because the story I’m about to tell here won’t take just a couple of paragraphs. It’ll involve a little bit of set up just to let you know what happened.

This is a true story, something that I really did, but that I can scarcely believe. It happened not very long ago, just before all this pandemic madness made social contact much, much more difficult.

So I’m 30 years old, and I’m part a really close friend group of two guys and two girls, of which I’m one of the two girls. We’ve known each other for a very long time, though I’m a slightly more recent addition as the other three have known each other all the way through high school. The other woman in the friend group I’ll refer to as S. The two guys I’ll refer to as B and Tom. S & B are in a relationship, and have been for a very long time!

S also has a best friend I’ll refer to as K, who I’m also very close with, and who joins us to hang out occasionally, though not all the time.

The Story of [M]y [F]irst Internet Hookup

So this is the story of the sluttiest thing I’ve ever done.

I was 22 at the time. I was just out of a 5 year relationship with my first and only high school girlfriend, and i was truly single for the first time since becoming an adult. Our breakup was less than amicable, seeing as how we were both trying to end our first relationship and had no real idea how to go about it. Needless to say, it was a rough patch, and without going too much into detail, suffice to say I was in the mood for some exploration. This led me to OkCupid. And OkCupid led me to, for the purposes of anonymity, Toni.

Toni was an older woman. Well, at least it seemed that way to me at the time. As a 22 year old man, 9 years seemed like a huge gap. However, this just added to her allure. I had never been with someone who wasn’t my own age, and she seemed so confident and sure of herself. Little did i know that this night would be the start of a long and lustful fondness for older women. Toni was my first match on OkCupid, and she sent me my first message. Her agenda was summed up very succinctly in 4 words:

(M)y jealous (f)riend finally gets her way with my girl(f)riend [MFF]

(M)y jealous (f)riend finally got her way with my girl(f)riend (MFF)

This story takes place about 17 years ago. I had just graduated from high school and was going to a local community college for 2 years to save money and mature a little bit before going to live at the university where I ultimately got my degree.

Flash back to my senior year of high school. I had met Jackie a handful of times through mutual friends. She was the definition of alt girl in the early 2000s. Short and skinny pixie looking girl with hair that changed color and styles weekly. She had a few tattoos and piercings, which I was a big fan of. She was really short, had small perky tits, and a great round ass. She also lived for the party. She was always down to do something crazy.

After meeting Jackie a few times, she was just getting out of a relationship with a real piece of garbage dude. Her and I began hooking up and eventually started dating. I did well for myself back then, but couldn’t believe I was actually dating the cool, hot, alt chick that everyone loved to party with.

A MILF in the Night, re-written [mF]

*I wrote this story about 9 years ago, shortly after it happened. I reread it recently and felt that the writing isn’t flushed out well enough. This is a re-edit intended to make the writing better. If you are curious what horny 21 year old me wrote, the original story can be found on my profile. I will link it in the comments. Both versions, while based on a true story, have been embellished.*

During my college days I was a very determined person. I had lofty career goals and I was working hard towards them. Unfortunately, this meant that I didn’t have much time to spare, no time for leisure or for relationships. When I moved to college, my high school girlfriend, Abby, and I broke up because the long distance thing wasn’t working out. After Abby, I hit a dry spell.

During the spring semester of my freshman year I got a job in a hospital near school. Having no marketable skills, my job was to transport patients from and back to the emergency room. Most of my shifts were from 7 PM to 2 AM (I had classes in the morning). The ED was often busy. People ran and yelled down hallways and across rooms about things I didn’t even really understand. I tried my best not to get in the way, to be a fly on the wall, especially at the busy times. My goal was to try to learn something. The environment was fascinating.

The Professional Woman: Part Five [MF] [Busty] [Straight] [Interracial]

Things hadn’t gone to plan. I expected some delays, maybe a hiccup here and there, but I was wrong, dead wrong. Nothing had gone right from the start. The building needed more work than we expected. The first day that we tried to turn on a tap, three pipes burst through the walls resulting in flooding on both floors.

It took another three weeks to get some of the girls back on our roster. Then the electricity went out, the wiring in the walls needed to be redone. From there, things kept getting worse, the heating, the flooring. Nearly four months after I signed my name to the building, it looked worse than the day I bought it.

“Morning,” I said as I entered our makeshift office. I stepped over power cords that led all over the second floor from a gas generator.

“Uh-huh,” Ginger said as she sat on a stack of milk crates one of the contractors had found around the neighborhood.

“Still no luck on the license?” I said as I sat on the only working chair.

A FantASStic Gamble [MF][Anal]

I’m not sure if this is against any rules. I loved [u/filthhunter69](https://www.reddit.com/user/filthhunter69/) ‘s story below and wanted to expand on it. [https://www.reddit.com/r/eroticliterature/comments/gpjtkj/i_fucked_my_moms_best_friends_daughter_in_the_ass/](https://www.reddit.com/r/eroticliterature/comments/gpjtkj/i_fucked_my_moms_best_friends_daughter_in_the_ass/)

******

“Oh my. That was fantastic,” my mom sighed as she set her paperback novel on the table. We were sitting on the back deck of our home on a warm May afternoon. I had just graduated college and had no idea what I was going to do with my life. The job market wasn’t exactly hopping with opportunities as it is. And I’m a political science major, for fuck’s sake. I just choose to not think about the decisions I have to make until I have to.

My mom picked up her phone. I knew she was calling her friend Carol.

“Yes, I just finished it. It’s so good!” Her eyes brightened as she listened to Carol gush over the same trashy novel.

“Oh sure! She can come pick it up this afternoon. I may not be home but Jeremy will be here. I’m sure he’d love to see her. Okay. Bye.”

“That was Carol. Kathleen is going to come by this afternoon and pick up this book.”

[FM] Stripping games turn into a fun night of punishment

As I mentioned in my first story, my boyfriend Henry and I greatly enjoy fucking (with) each other. One of our favorite games to play is “strip anything.” Here’s how you play: you turn every tiny thing in your life into a competition and then you incorporate stripping.

I should warn you that Henry and I are incredibly competitive people – our casual neighborhood walks almost always turn into a race to get home before the other person, and our grocery runs inevitably devolve into a game to see who can find the best deals on produce. How do you turn these into stripping, you ask? Easy! You just eventually rip off your and your partner’s clothes. Our races home end in a competition to see who can get naked faster once we get there, and the other person has to go down on them until completion. Our grocery bargain hunting ends with the loser having to perform a strip tease and masturbate in front of the winner. We also sometimes play strip cooking, where we have to take an item of clothing off whenever we finish a step in a recipe. Preheat the oven? Off go your socks. Wash the veggies? Yeah, you take off that paint-stained high school theater sweatshirt, you dirty girl.

[M]y Best [F]riend Part 4: Changes [Long]

This one has a lot of backstory/build up, but I’m also not writing every time we had sex because it’s not r/StevenandEmmy and I don’t think it’s necessary. But this one is. Enjoy.

Fast forward to last year. Emmy was in her senior year of college, about to complete her degree in nursing and already had a job lined up at the hospital in her college town. I graduated from the technical school and began working on my ASE certification. I landed a job at a well known shop also in her college town which was great because I could spend time with Emmy and other high school friends who attended her university. Additionally, I ended up living with her grandmother, gramma, who was lonely as Emmy’s grappa died just before we started college.

Emmy and I were able to keep our relationship, even at a distance. We would FaceTime or have Skype sessions when we needed each other for relief, and the occasional sexy picture. Before anyone asks, I haven’t and won’t share them because I respect Emmy too much and I’m a selfish bastard.

Amy’s Adventures

Amy liked working in the city. It seemed to be an escape from the sometimes dreariness of being a mother in the suburbs. Seeing the different faces, and the hustle and bustle a big city provided gave her something to look forward to. Amy had married her college sweetheart, bought a house in the suburbs, and had two children who were her entire world. The spark in her marriage had disappeared for the most part, and her husband spent more time gaming than paying attention to her or her needs. This led her back to the workforce, in a demanding job that she quite enjoyed as a respite from the mundane. Sure, she was an accountant in a mid-size law firm, which doesn’t seem to be the most exciting of professions, but interacting outside the closed circle of mothers groups, as she had done for the last few years was a welcome change. She had a small office in one corner of the building, and while the rest of the building was awash with floor to ceiling glass windows, her office was only filled with artificial light.
It was not uncommon for her to work late, especially at the end of a billing quarter. She had realised early on that law firms were exactly what people thought them to be. Turning over large sums of money, charging for the most inane tasks, usually performed by interns or juniors. It was also true that most of the partners were middle aged men, who usually hired young attractive staff, in the hope that their drive to climb the ladder to success would be enough to entice them into become willing play things for their bosses. Amy didn’t worry about that too much, she was a good ten years older than most of the interns, and whilst her body still looked slim and toned for a married mother of two, she felt she would be one of the least desirable in the office.
Amy also had a secret. She had always had a high sex drive. Although she grew up in a conservative household, she had discovered her body and the joys it could be bring fairly early. Late in high school she discovered boys and how they could bring different pleasures to her. By the time she was in college, Amy had become quite liberal with getting her needs met. In fact, prior to meeting Tony she had been intimate with several of his friends, which on one occasion included a lot of liquor and being shared amongst a couple of them. Those days were well behind her, but the desires that drove her back then, had subsided when motherhood took over, but now were back as the children grew older. Tony had lost interest, preferring to watch “cheerleader” porn for his quick fix, before dozing off into a snoring slumber. Too lazy to delete his browser history, or maybe he just didn’t care.
So working late agreed with her, because it gave her something she couldn’t get anywhere else. It gave her the opportunity to be alone with her thoughts, or her memories, or her fantasies. It allowed her to escape in silence to places where she could meet the needs of her desires, even if only inside her head. Pleasuring herself in comfort was not possible at home. She very rarely showered alone, nor did she get much time where there wasn’t another body present. She would sometimes sneak into the bathroom and quickly bring herself to orgasm but that didn’t allow her much time to enjoy the moment she was desiring. The proximity of her office allowed her to use this alone time to savour such a pleasure. She would always do a sweep of the office to confirm she was alone, and she knew the cleaners always came after midnight.
It was after 8pm now and she was confident that she was alone. She had just messaged Tony to let him know she would be home around 10. She always dressed a particular way on these days. In some ways it made her feel sexy, but mainly it was for convenience and access. Although she liked the idea of it being risky, she certainly hadn’t wanted to get caught. She wore red heels, with a black a line skirt. Under the skirt she wore black lace panties. She felt black looked best against her white skin. She wore a white blouse, whilst not sheer, certainly allowed her lacey white bra to show through, her nipples making a small yet noticeable bulge in the cup. She wanted to be noticed on those days so that by the time she was ready to entertain herself, her body had been warming up at the ogling she had been receiving. Today she felt she had got more attention than usual, and on more than one occasion caught the men in the office staring at her, particularly her perky nipples. She had been mulling this all day, and this time couldn’t have come soon enough.
She did a final wander through the office to ensure there was nobody around. She drifted past the offices of the partners, those with views of the city, it seemed that every had somewhat of a view except for herself. The path she walked was well travelled, it took her to the bathroom if she ever ran into anyone, and her return would take her past the ones she missed on the way over. It was so quiet she could hear the sound her heels made every time they pressed into the carpet. She reached her turnaround point at the corner of the floor. The largest office belonged to the managing partner Terry. An average looking man but seemed well built. It was hard to say if he worked out or it was just his natural physique. He invoked fear in most of the staff, especially the younger ones but he and Amy always seemed cordial. Maybe because she was older or maybe because the company’s financial secrets that she was privy to. His office overlooked the entire city. The view was even more amazing at night. He had a large mahogany desk, with a maroon leather chair. There was a matching lounge on the other side of the room that sat behind a coffee table. She walked back to her office ready to enjoy what shed been longing for all day.
Amy got to her office and realised how dreary it looked compared to the any of the others. She thought that she deserved a treat that she wouldn’t normally be afforded and would add to the excitement of her adventure. She would use Terrys office and turn his chair to face the city as she did. She would embrace the exhibitionist in her, and truth be told that even with all the planning that went into these days, she usually came within the first ten minutes or so.
She walked back down the hallway and into the open office. She admired the view for a moment before she sat herself down into his chair. It was more comfortable than she imagined. She felt a sense of power behind that desk, but a sense of excitement was starting to bubble between her legs and she knew she needed to attend to that sooner rather than later. She hiked her skirt up to her waist and slid her hand into her panties, her fingers gliding over her hairless mound. She ran a finger over her clit, and she could already feel it pulsing. She made her way a little further down and slide a finger inside herself. She let out a little gasp, even surprising herself with how wet she was. She spun the chair towards the glass window and spread her legs a little wider. She knew it was unlikely, but she was further aroused by the fact that somebody might be watching her and pleasuring themselves at the same. Her eyes closed and her head hung over the side of the chair as another finger joined the first with ease. She pushed them in and out of herself moaning with every deep probe.
She opened her eyes to admire the view briefly, maybe even catch some ogling eyes in a neighbouring building. Her vision darting across the glass quickly. Her eyes caught a shadowy figure. Was it her imagination? She looked again and realised that there was a silhouette reflecting off the glass. Her heart sank, and the pleasure drained from her body. She was in shock, but she didn’t have a choice. She had to turn around and face whoever had seen her. She didn’t know what she could or would say that would make this ok. She had removed her hand and slide her skirt down before spinning the chair around.