I had the biggest crush on a woman that I had zero chance with. I’ll call her Samantha for the sake of this story. She was heart-stoppingly beautiful, insanely smart, incredibly ambitious, fit and sexy as hell, and — in the circles that I traveled in — a celebrity of the industry. From the first time I saw her I was in deep crush-from-a-distance and so were all of my industry peers. I interacted with her occasionally at conferences and she was usually pleasant if not overly cocky about her awesomeness. She had a glib tongue and a sardonic personality — which, honestly, made me like her even more.
Author: s0m3thingc1ever
We got stopped in a public park by someone trying to feed the ducks [MF]
I started talking to her online — she lived about 15 minutes from me — and she was really cute. Eighteen years old, thick thighs, round ass, great curves. She had dark hair, light eyes, and a really inviting smile. It was summer time and she had just graduated high school a few weeks before and was working at a car dealership in town as a summer job. She was the kind of girl that didn’t portray herself as innocent or hard to get and I found that incredibly appealing.
We exchanged phone numbers a day or two after we connected and got to talking one Friday while she was on a work break. Things turned sexual very quickly as she mentioned how horny she was and that she hadn’t had the chance to masturbate that morning before work like she normally did. I love when a woman shares details like that out of the blue and I chomped at the bait asking her “Well do you want me to help you out with that?”
I seduced a married woman [MF]
***This doesn’t end with anything sexually gratifying — I just think this was an interesting story worth sharing.***
As several of my other stories have mentioned I spent most of my time in my early 20s working in a restaurant/bar and studying martial arts. This was at the tail end of my time working in the restaurant business as I had finally gotten a “big boy” suit and tie job and was winding down this part of my lifestyle before I moved to the city and made more time to play.
It was early summer, a Friday or Saturday night, and it was beautiful outside. Business had been really good that night and I had a lot of cash in my pocket, nowhere to be, and free drinks coming to me as part of my shift. The other servers and bartenders I worked with that night who closed with me were my favorite ones so we were going to hang out and party until late.
The Au Pair [MF]
I think I met her on MySpace. Her pictures were beautiful. Blonde hair, blue eyes, incredible smile. As far as I was concerned I was shooting my shot to meet her with almost no chance of success — girls like her didn’t go for guys like me. I don’t know why, but she was into it. Her schedule was really complicated, she was from Budapest and was working as an au pair, or nanny, for a rich family that lived about 45 minutes from me. She almost never had free time so it took a while before we had the chance to meet one night.
Apparently, the family she worked for was on vacation and had left her behind to house sit and have the weekend off. She picked me to be her date that night and we met at a really cool bar down by her in the historic part of town. She was even more gorgeous in real life than she was in photos. She was fairly tall, 5’9”, very slender, and I could feel her energy the moment we locked eyes. I felt very privileged to be in her company and was looking forward to wherever the night took us.
Best Head Ever [MF]
I had been — technically — single for about a year. I had decided I didn’t want to do the “relationship thing” again unless it was with the right person and I was actively pursuing the wrong people. I discovered AdultFriendFinder — a very sus website for meeting people explicitly for sex. I made up some abominably bad user name, posted a few photos of myself in the buff, and got to messaging people. Surprisingly, it was actually a decent place to meet people as long as you were patient and deliberate. I definitely got cat-fished on there a bunch of times, but I also met five or six (or more?) people from that site over the years. More than that if you count the time when my FWB and I had a couples profile.
I digress, I was on AFF, and one of the first people I met in person was a girl named Beth. Beth only had two photos on the website, they were incredibly small and low resolution, but she looked cute if not a bit intense. Dark hair, big blue eyes, pretty face, but she didn’t smile. We exchanged email and I sent her a few more photos of me in the hope she would do the same, but she said she didn’t have more pics and that “cameras and i don’t agree with each other lol.”
We blamed it on the Thai food [MF]
I had been seeing a girl who was in the US Navy for a few weeks before she was set to deploy. It was almost exclusively a friend with benefits arrangement and it was a lot of fun. She was incredible in bed and fun to chat with during the down time. I normally worked random nights during the week and basically every weekend as I was a server and occasional bouncer. Additionally, I was training in martial arts regularly and the nights I wasn’t working I was getting my ass kicked by someone. She reached out to let me know that she was only going to be around for one more week before she shipped out so I took some time off to hang out with her.
Lots of fun with a Navy Girl [MF]
I met a lot — LOT — of people on MySpace when that was a thing. It didn’t have the explicit intent of being a dating site, but it worked out well for meeting people back in the day. I was not particularly good at risking embarrassment and asking someone out face-to-face, but I was incredibly good at doing it online. The low risk, high reward, instant messaging connection worked well for me. I have always enjoyed writing and banter and since many people are not good at that — or fast typers — I was an online “catch.”
My first “Hotwife” encounter [MF]
A small group of us had traveled to North Carolina for an advanced martial arts seminar. It was only going to be a two day trip, arrive — stay the night — train the next day — return home. Normally when our group traveled it was a lot more of us and we stayed for a long three or four day weekend. I was lucky to be able to go, it was almost all instructors and just three students. Me (23) a purple belt at the time, a close friend of mine and a brown belt — lets call him James (24) — and a red belt woman — lets call her Michelle (39).
I had been training with them for a little more than year and was having a blast. Michelle was one of my favorite people to partner with because she was a complete badass and had a super fun personality on and off the dojo floor. She was a bit of a flirt, but I knew she was married with kids and I think she just liked to play around; I was sure it wasn’t serious flirting.
People were watching us fuck in the car the whole time [MF]
Little did I know, but it was going to be our last night together for nearly five years. She had recently moved away to go to college across the country and we were trying things long-distance for a while. She was home for a long-weekend to celebrate her birthday and we were spending as much time together as we could before she went back. I was falling for her, big time, and each encounter we had was wrapping me up in her web more and more. She was beautiful, smart, exciting, wild, and very into me.
It was a Sunday and she spent the morning with her family. Her father was a pastor and they often hosted people at their house Sunday afternoon and into the evening for religious discussion and dinner. Surprisingly, she invited me over early and I joined in with the family. She was still her dangerous and rebellious self, but I was introduced to a different side of her that was very interesting that day. Really solidified my interest in a more-than-sexual way.
Almost caught fucking on a picnic table at a public park [MF]
I had the biggest crush on her. We had been dating — sort of — for a little while but it had been long-distance for the past two months. She was in town for her birthday, which had been the day before, and we had absolutely mind-blowing sex. It was a Saturday and she had spent the entire afternoon with her family and friends celebrating, but she had reserved the night for me. I got to her house around 8 to pick her up. I had been given explicit instructions NOT to come to the front door, but to call her instead so she could run out and meet me.
I don’t know if she was sneaking around or just didn’t want to waste time, but I saw her run around the side of her house toward my car, she jumped in, and she told me to drive. We didn’t have anywhere to go, or anything in specific in mind. We were just going to enjoy one another’s company and, hopefully, fuck a lot. She had an idea at one point and directed me to take a left here, a right there, drive ahead, then stop in the parking lot of a public park. We jumped out of the car into the chill of the evening and walked back to the swing set nearby. She sat down, grabbed the chains, tossed her hair as she leaned back confidently, then gave me a devilish grin. She was a succubus and I loved it.