[FM] An Affair with a Married Man; The Best Sex of my Life (20f,42m)

About myself: I’m a 20 year old college athlete who makes top grades and spends a ton of time on Reddit. I started dating a guy over last summer my parents set me up with through church. (my family is very religious , I’m not but I hate to disappoint them so I go) He is good looking, nice and caring but something is missing. I said yes to dating him because my parents loved him. The hardest thing about dating him was he wanted to wait for marriage to have sex . Over that period of time I had become very good at putting on a mask and pretending to be happy while pushing down what I want.

This all took place during the past holiday break a few months ago now. My family consists of my mom , dad and older brother. A week into me being home we went out to eat with my Mom’s best friend and her Husband. They wanted to see me since I was back in town because they are like 2nd parents to me. I had banged up my knee earlier in the fall training so they asked me how it was feeling. I shared with them it had been hard because I haven’t been able to run since the injury. The husband (I will call him Mr.Thompson) felt bad for me and invited me to use their pool at anytime over the break to train. They have a lap pool they keep heated in the winter I used it in high school for workouts. I decided to take him up on his offer.

[MF] First day of spring break I end up hooking up with a guy 3x my age

A couple of my friends and I decided to take the little money we have and take a spring break trip down to Florida. We flew down early yesterday morning and went to the beach right after we checked in the hotel. It was spring break in Florida so of course I had to wear my thong bikini that showed a ton of booty. I started by tanning on my belly, you could occasionally hear guys commenting about my body but I was used to it. I flip over and tan laying on my back with sunglasses on. I guess people thought I was asleep because I got a lot of blatant stares, I enjoyed it. No guy really caught my eye just a lot of college guys my age staring.

Rented a car and had the hottest sex of the year [FM] (long)

Last week I was bored and felt like a little adventure. I texted my FWB to see if he wanted to meet up. As always, he was an enthusiastic yes. He’s a bit younger than me and I normally wouldn’t fuck someone so young but he’s hot and plays sports with a great body and very, very good in bed. This is all great but I wanted something more than a “your place or mine” fuck like we always do. The last time we met up he picked me up in a rented car (one of those city cars you can rent by the minute) to go back to his, and this gave me an idea.

The night before we were meant to meet I texted him “I’ve been fantasising all week about you picking me up in one of those cars and driving somewhere quiet”, he replied “I guess we have our plan then!”

I showered and dressed in some hot lingerie, suspenders and stockings, and put a cute dress and some thigh high boots over the top. He texted me to say he was on his way, I replied with a picture of my dress hitched up ever so slightly so you could see the tops of the stockings and the suspender garter. “Waiting patiently” I replied.

The Night She Sucked Me Dry [FM]

This happened a few years back, I think back on it here and there and figured I’d share here.

**Info**

Me: At the time in the story I was in my mid 20s, I’m 6’3″ built like an NFL lineman, I was a bit more fit back then. Dark hair, dark eye, short kept beard. My dick is above average on thickness and length. There is a pic on my profile if you’re curious.

Her: We’ll call her Rebecca, she was in her early 20s, around 5’8″, she was a little chubby, a few extra pounds on her but it worked for her and I liked it. She had jet black hair, dark brown eyes that were piercing and a huge set of tits. I believe they were E or F cups.

—–

I got home early from work, got changes as fast as I could and headed to Becca’s place, anything I had to do could wait until the next day. We’ve been talking on and off for nearly a year of varying types, from basic chatting to full blown sexting and picture/video sharing. We had met a few times before but just a run into each other type situation, have a quick chat and be on our way. This was finally the moment we both waited for, a day where we could just let loose and have some fun, plus it didn’t help she was teasing me before hand.

Sailing lesson [MF]

We had just gotten married. It almost didn’t happen. I’d gone to Fiji and sailed from there to Australia with an old British SAS guy whose autohelm was out.

Great stories there but I’d burned through my travel money and wanted a boat of my own. So I came back to Seattle and my ex was still there and one thing led to another and we got married.

She agreed to go with me and signed us up for sailing lessons. I wouldn’t have bothered but she wasn’t secure enough.

Every weekend we went up to Bellingham and chartered a yacht with instructor and did the ASA sailing course and coast guard navigation class on Wednesday nights.

Most of the sailing instructors had been men but on the last course it was a woman. She was young and pretty and knew less about sailing than either of us. My wife was pissed and also catty.

The wind picked up and we were supposed to learn how to heave to—point upwind and trim the sails so the headsail backfills and the main keeps you pointed straight upwind. This basically stops the boat so you don’t run up on shore or a reef during a storm.

[MF] Cabin trip part 2 [more cheating]

First part and backstory found here: [https://www.reddit.com/r/gonewildstories/comments/b1eu5x/meeting_up_with_old_friends_for_a_trip_to_the/](https://www.reddit.com/r/gonewildstories/comments/b1eu5x/meeting_up_with_old_friends_for_a_trip_to_the/)

I left you off when we were in a giggly mood after getting each other off under the blanket, and we decided that we should go to bed. I was sharing a room with my male friend in the hot tub, and Ann was sharing with the girl. Very practical, so we decided just to walk up to them and tell them that they could have the girls room, we would take the boys room. They had not seen us earlier, and not noticing us doing our thing, so naturally they were quite surprised when we walked up, trying to cover up and pretending not having done anything wrong. I just finished with a “good night, and have fun” when i took Ann to my room. We were both exhausted, so even if undressing her and spooning her naked did not make it possible for me to do noting else than go to sleep with my semi-hard dick pressing towards her ass.

More than bargained for [MF] Cheating

One day she messages me and tells me her house will be empty and she wants me to be there when she gets home from the bar.

Of course, I’m so into it so I head over when she texts me that they will be home soon. I’m completely naked and she messages me that she won’t be alone at the the last moment. I run to her room and wait in her bed. I hear voices. She comes to her room alone as I am naked in her bed.

She quickly pulls the covers and sucks me until hard (a matter of seconds) and then motions to follow her. She stops me in a room with a view of her family room. I can see two people in there from where she motions I sit.
She goes back to the family room with whom I recognize is her best friend (a hot slim woman in her mid-30’s at his point, married with no kids) and some young guys her friend is making out with. Mary goes in and takes charge by stripping naked and making each of them join her. Of course, the guy is quick to join. Her reluctant friend joins the nudity as well. I am stroking myslef in a room off to the side. My heart is racing.

I fucked a geek and I liked it [MF]

So this happened a few years ago now, but I’m feeling horny and bold enough to finally share it without having to anonymise any details.

I used to help out at a bookshop for a few hours a week just as a favour to my friend who owned it (hi Danny). It was quite a quirky place, a bit hipster and bohemian, staffed predominantly by socially-awkward oddballs. On the whole, they weren’t exactly the most attractive bunch – guys in their 30s who were prematurely bald (sorry Danny), girls in frumpy dungarees with grubby-looking dreadlocks – you get the picture.

And then there was Isla. She was a little bit younger than me at 23 – but she barely looked 20. I can only describe her as looking like a hot librarian, because she did. She wore glasses with small frames that she would alternate between sliding down her nose to read with and propping them up on her head, tangled in the long straight dark hair which reached down to the small of her back. She almost exclusively wore a stretchy, tight fitted polo-neck of some description and a high-waisted pencil skirt with a large belt wrapped high around her waist. She had tiny breasts but a cute ass, which was disproportionately curvy, relative to her small size. It was helped by her habit of wearing large-heeled boots which had the effect of changing her posture such that you could see her skirt protuding over her butt rather than hanging straight down.

How I [M] helped a friend[F] in need and it led to a weekly blowjob. [Long]

Hey everyone, this is a story from a few years ago when I was at University. It starts off with the same old, a friend from High school who was in a very different social circle reached out to me through the very much infant stage Facebook, we got chatting and it led to a great relationship, we used to talk about pretty much anything and everything.

She was blonde, tall at 5’8, not a skinny but slim body but she had awesome tits for her shape, full and always spilling out of low cut tops, sun dresses and the odd bikini or two at some of our once in a lifetime Scottish summers. I used to tell her that often, it became a running joke that she should get them out to accomplish her goals “she had a pretty face with one dimple on her left and looked better without too much makeup.

So it’s been about a year that we have been firm friends. I get a call out of the blue asking “can you come over, its important”

I [M] just had one of the hottest sexual experiences of my life with my FWB [F]

Im currently working in a different town from my hometown, about 300 km away. Naturally, over time, I grew bored and decided that now was the best time to try my Luck at Tinder. Finally, at just about a month left before my contract here runs out, I found somebody who was up for a short term FWB Situation.

After two successful Dates we agreed to hang out at her place on Saturday. I’ll spare you the Details of what we did until it came down to fucking, but lets just say some alcohol and alot of talking was involved.

I am honestly not that much of a looker, 5’6, slight chub, generous amounts of groomed chest hair, short dark blonde hair that has a propensity for curling up when sweaty or growing too long and blue-grey eyes. I would consider myself simply an average guy, but I have gotten compliments in the past for being a cushy cuddly guy, so I have that going for me.