gonewildstories Archives — Page 528 of 5640 — NSFW story

[MMF] Just be Careful; They’re Swingers: Part I

TL;DR I got involved in a cuckolding relationship for the first time. The wife and I would go on to date on the side.

It all started at a company Christmas party. Usually we were a buttoned down type of company: jeans, t-shirts, sweaters, Birkenstocks, you know, that kind of stuff. I was in my 20s when this took place, in my second professional job.

My colleague Jill (my bestie at the job, and confidant) told me that the company Christmas party was super formal, unlike the office, and she even took me out to help me buy a suit. The party itself was as advertised. Most of the people in the office were a LOT older than me, but the vast majority of them cleaned up well: suits, evening gowns, fancy dresses, shiny shoes, high heels, the works.

[M]y [F]irst Time

I was 41, and separated from my wife. I was behaving (mostly), and working on trying to save our marriage. I had my own place, and we had a pretty good arrangement. Things were looking up, to be honest; and, we had talked about getting back together.

One evening, while I was sitting in my living room, the bell rang. I went to the door, and was greeted by a former colleague who lived nearby.

“Are you divorced yet?”

“No.”

“Well, I brought you a bottle of wine. Invite me in for a glass?”

“Sure?”

Amanda was 50, blonde, petite, and in excellent shape. She had small breasts, a flat stomach, and awesome legs. What could go wrong?

She sat down in the living room while I opened the wine, and poured two glasses.

“You know,” she said, “we’ve never been available to each other. We still aren’t.”

Okay, that makes this all a lot easier.

We start talking, and we have another glass of wine.

And another.

The bottle she brought is empty, and she says she should get going. Read more »

Made Love to a Married Man … He Kept Our Underwear FFM [FM]

So Babs and I decided to go to this super fancy as fuck cocktail place downtown.

Babs is not leaving much to the imagination. She had a mini halter dress on. Sleeveless. Backless. Exposed belly. Exposed chest. Just two straps running up each side, covering her glorious tits, looping around at her neck.

I dressed more reserved. I had a mini dress on as well but it covered everything and was full sleeve. Just a small cut out at the back.

There was no real intention of picking someone up for sex. We just wanted to get drunk.

Anyways, we’re enjoying ourselves at the restaurant. This was going to be one expensive night looking at the price of each drink and the bites they had on menu.

Babs has been eyeing a table of men for a while. Particularly one guy. He looks older. Had to have been mid 30s. But he was pretty good looking.

“Go pick him up” she tells me

I just look at her

“You know … for a whore you’re so useless … ”

She doesn’t do anything

“Well aren’t you going?” I ask Read more »

My well planned work trip [mf]

This is a true story from my work trip to Austin a few months ago… also, if you’re going to judge or throw stones, don’t. I don’t judge you and would expect the same in return.

Back story –
I’m happily married 39/m, 6 feet tall, 270 ex-athlete gray hair and hazel eyes
She’s 5’6, 42, black hair, brown eyes, 38DD and perfect curvy ass

This is a long build up and if you want to skip to the sex, look for the ***

If you read my previous story you’ll see that I met her when I was separated from my wife and she was newly single. She and I are very close and would never, ever want to harm each others relationships but also cannot deny the chemistry we have for one another. Since the other story she has married and actually had another child… there was even a minute when I wondered if it might be mine 😬, but that’s a different story. Also, since last time I have moved states and only seen her maybe 3 times since leaving. We talk almost every day, but the actual seeing each other has drastically cut back. Read more »

(32)[F] – (22)[M] Intern at work – The Back Massage

These are the continuation of the events that happened more than a couple of months ago.

This picks up from where the previous part left off. You can read Part 31 [here](https://www.reddit.com/r/gonewildstories/comments/ymfpr4/32f_22m_intern_at_work_the_build_up/)

**Part 32 is below**

I stepped out into the backyard and found Eric sitting by the side of the pool with his feet in the water. He looked up when he saw me stepping outside.

*Eric – “There you are, Pallavi. You were gone for so long that I thought you had ghosted me in your own house.”*

*Me (Smiling) – “Sorry, babe. It took a while to find that bottle of massage oil.”*

I handed him the bottle of massage oil. It had a suggestive picture of a woman who was about to pop a couple of cherries into her mouth, which I guess were meant to resemble the balls.

*Eric (Smiling) – “Edible massage oil eh?”*

*Me (Giggling) – “That is all I could find in my house, babe.”*

*Eric (Winking) – “I suppose it is good thing that I like cherry flavor, Pallavi.”* Read more »

[MF] Bar Handjob [Public]

I was bored one night, so I went to a local drinking establishment. There was live music, drink specials, and it was College Night. I was in my mid 20s at the time, bit fluffy, and kind of shy. I was sitting at the bar enjoying my drink, and a very attractive redhead slid up next to me, proclaiming to the bartender it was her 21st birthday. Me being me, I offered to buy her a birthday drink. She says she wants a “breakfast shot” which I’d never heard of. Orange juice and butterscotch. Tastes like pancakes and maple syrup. I tried one with her, and it was damn tasty! She told me her name was Brooke, we exchanged some pleasantries, and she went to sit with her friends. Read more »

My Account Manager and the Thong [MF] [F]

I think I owe it to Vicky to share another story about her, because notwithstanding the origin of our relationship, she became a favorite FWB of my past. She was a LOT of fun because I was experiencing her, in real-time, discover and explore her newfound sexuality. It was incredibly erotic, and I feel lucky that she shared some of it with me.

For Victoria, sex went from repressed and nearly non-existent to nearly all-consuming in an instant.

After my three-day fuck-fest with her, the following Wednesday we had a scheduled year-end meeting with her account team to plan out implementations for the following year. Victoria was leading part of the session. No one other than me and my boss knew that I had provided my one month notice prior to the meeting (he was trying to counter-offer). So, my level of “give-a-shit-ness” had declined greatly, which is (I think) part of the story.

The previous night I sent Victoria a very short text.

*I dare you to present commando tomorrow.*

The next day in the boardroom her team showed up and as usual, Victoria was dressed in her prim, professional outfit. A structured business suit with mid-calf hemline and sensible 2-inch heel pumps. Read more »

[M]y first time with a married MILF twice my age. [MF]

Sorry this story got kind of long!

Enjoy…

When I was younger, about 24 years old I went to a Journey concert with some friends. When I got to my seat, I noticed that the woman sitting next to me was an absolute smoke show! She was definitely way older then me, as were her friends but she was absolutely gorgeous. I struck up a conversation and as the show went on she was drinking and flirting with me more and more. I’m not gonna lie, I definitely noticed she has a ring on her finger but we were having fun and it seemed innocent. By the end of the show she had her head on my shoulder and her huge tits pressed against my arm. She was drunk and I wasn’t about to take advantage of her, so at the end of the night I got her number and we went our separate ways.

How a nude pic from a [F]riend led to the hottest UNDERWATER Blowjob ever. (PART 2) [MF]

So, if you haven’t read Part 1, you should start [[HERE](https://www.reddit.com/r/gonewildstories/comments/yoy71p/how_a_nude_pic_from_a_friend_led_to_the_hottest/)]

I’m gonna pick up right where we left off.

After hanging out, talking and making out a little bit in the hot tub, me and (let’s just call her “L”) decided to go inside and get something to drink. I had never “house-sat” before so it seemed really odd to me to just walk into someone else’s house when they were not there and raid the fridge, but L was perfectly comfortable.

So here we are, standing in the kitchen of this big ass house, in our bathing suits, soaking wet, drinking smirnoff ice out of someone else’s fridge.I was just polishing mine off when I see L walking away down a dark hallway… I figured she was going to the bathroom or something until I noticed her dropping the straps of her bathing suit off of her shoulders. Just then, she looks back at me and bites her lip before disappearing into some random room. I RAN to follow her. My dick immediately started to get hard again. Read more »