Category: gonewildstories

Layover [MF]

Dee and I had stayed in touch since we split up; mostly just chatting and the occasional flirting session. But distance had cooled the passion over time. What was the point of becoming invested emotionally and physically when we weren't the emotionally and physically just was not going to happen.

I traveled a bit, but she flew constantly with her work, although unfortunately nevere to my town. On this one occasion I flew cross country, connecting in Toronto (Dee's hometown) on my way to the east coast. The weather worked against me and my connection arrived late ensuring me a long wait until morning with some security guards and late night maintenance people to keep me company.

I texted Dee to see how she was doing these days.

"Hey kiddo. Stuck at YYZ. Entertain me?"

Her response was immediate. "How long?"

"3 hours. 5am flight."

She respnded with an image. Her in bed, possibly naked with her finger against her temple like she was thinking. "Dont move, I have an idea." She sent a series of images over the next 30 minutes. Read more »

Move to a new city, join the swing set. ([m/f], [m/f], [m/f], observed [m/f/m] and [f/f])

A little more than 24 hours ago, I made a life-changing decision and had the best night of my existence. Enough that I want to write about it and share it. And I already want and need more.

My vitals: straight male, mid-30's, mid-divorce. 5'9", about 250. If I were into men, I guess you could say I'd be a bear. I've had some experience with kink and non-monogamy, but since getting divorced and moving near a major northeastern city, I've decided I want to explore these more. I know I'm a dominant person who isn't all that big on physical monogamy, but in terms of actually playing, I haven't done much.

As it turns out, my ex-girlfriend from college, Carrie, had also gone on the same journey (divorce, sexual exploration). However, she joined a couple of swinging groups in her area (which was closer than I expected) and has blossomed big-time. A while ago, she mentioned that she was going to be dancing in a stripping contest at one of those groups. Back when we dated, Carrie wasn't exactly repressed, but she's gone headlong into kink, so I desperately wanted to see her in a new light. And have some fantastic sex, of course. Read more »

Casual reddit post turned into [f]ucking a co[m]plete stranger

This just happened to me this weekend. It was completely unexpected and one of the hotter things I've ever experienced. Two weeks ago I (24m) had posted on my local subreddit (/r/brisbane), asking what kind of sober events are on during the weekend. I got a few replies, one in particularly from a 22 year old (who we'll call Sarah) saying that she'd be interested in doing something as she was new to town. I didn't end up doing anything that night but we began casually messaging.

Two week after this we've sent a few messages per day to each other and I'm not thinking anything of it. Then the conversation turned a little dirty and we discussed the idea of fucking a total stranger. We both got turned on by the idea as by this stage neither of us had even seen what the other looked like. We decided that we would do it, and Sarah sent me her address.

On the drive over I was nervous, I really didn't know what I was getting myself into. Sarah had told me how to get to her door and had mentioned that she'd leave it unlocked. I rolling the dice big time, I had no idea what this girl looked like and here I was, committed to fuck her. Read more »

I Cheated on my Boyfriend at Work. [F/F]

I’ve changed some details about this because I could get in a lot of trouble if it came out. For that reason I might not answer too many questions. Well I won’t be too specific with my answers at least.

My name's Helen I’m a very normal person really. I’m outgoing and like normal stuff, and I have an outgoing boyfriend who likes normal stuff too. We both exercise a lot together and we’re both in good shape which is something important to both of us. But other than that we’re like any couple. Our sex life is fine too, and the only complaint I have is that he doesn’t go down on me nearly as much as I would like. But it’s not a big problem really. All in all we’re very happy, we live together, and are planning a future. So I never thought of myself as a cheater, which is why it’s so weird to me that I’m writing this. Part of me writing this is because I want to share something with a subreddit that I have enjoyed for a few months now (made an account for this!), and part of it is to get it all off my chest because it's been a weird few weeks. Read more »

Fulfilled one of [M]y [f]antasies last night! Thanks Tinder! [24m/21f]

Hey guys! Long time reader and fan here. I had an experience last night that was so good that I had to tell someone, and where better to tell it than here, where the details are appreciated? This is my first submission to gws, but I intend to record my back-catalog of stories as time goes on. I hope you enjoy!

To set the stage: It was Friday afternoon and I had just gotten home early for a weekend of well-earned rest. Normally, I hang out with my house mates and work around the house on weekends, but as I settled in, I noticed that both of my room mates were packing up to leave- one for the holidays and the other just for the weekend. I realized I could be in for a long, boring weekend, but I also recognized the opportunity that comes with having the house to myself. I wished them both a good weekend, sat down, and got to work on Tinder. With the holiday season upon us, I was getting matches considerably faster than normal and was engaged in several conversations when a new match appeared. I clicked on her profile, a cute 21-year-old girl from the edge of my search radius, read the blurb, and realized that I had just stumbled upon a golden opportunity – the chance to sleep with a pregnant girl. Some of you may be turned off by this, but I'll explain the appeal in the next paragraph, and those of you who are interested can read past the explanation, and if not, feel free to tune in for the next story! Read more »

Not Your Average School Day [F]

Im going to apologize right now for the formatting since I'm on my phone but I just couldn't resist making another post on here.

It's February last year after finding out that I had gotten into college. Unlike a lot of seniors I actually showed up to school but didn't feel like actually putting in much effort really. I needed spice up my Wednesday somehow to help with my senioritis but couldn't seem to find anything. That was until I got my brilliant idea. After a bit of thinking I walked into my closet and snatched my buttplug out of its hiding place and popped it in. I pulled my panties and jeans on over it before grabbing my things and heading for my car.

I arrived at school on time and tried to keep my cool with my ass stuffed as I walked from class to class and sat through notes and lectures. I had managed to hold it off even though I felt it building up for a while, but at lunch it was too much. I set my things down in the teachers room that I usually stayed in during lunch and headed for the bathroom. Read more »

Couple [m/f] gets drunk and has sex. With pictures!

Not the wildest thing ever, but it was our best night in a while. Hope the pictures help.

My (attractive female) partner of about 5 years had nice night out recently. We got some free tickets to an event about an hour away so we decided to make a fun night of it. It started when she was getting ready at the house and she put on her sexy underwear. We don't get to go out as often as we used to, so it was a treat and got me exited from that moment on. We drove to our destination, had dinner and drinks, and were feeling pretty frisky by the time the check came. I knew I didn't want to just go to the event now and drive back home afterwards so I booked us a room nearby for the night while still at dinner. We then went to the event where the I'd occasionally mention to her how I intended to fuck her later. After the event we stopped by a bar on our walk to the hotel and refueled our giddy buzz and hit on each other. We then ventured on to our hotel. Read more »

I’m back: Threesome with a girl from a previous story and one of my friends from college [m/f/m]

Some of you might remember me. I posted under a different ironman name up until recently. I deleted my account, because it got hacked. Some of the stories I posted over the last couple of years are gone forever from reddit, so I figured I would come back and start posting some old ones to make sure they aren't lost. I will post new stories as well when I have a chance. (New stories will come I promise). Here is an old one. Hope you enjoy:

Like I've said in previous posts. I figured it would be fun to go back to my promiscuous (man-whore) days and recall some of the stories from back then. I'm generally considered a really good-looking guy (used to model, 6’3”, dark hair, blue eyes, swimmers build, workout regularly), so that enabled me to have quite a fun sex life. These stories are 100% true and not embellished in any way. I think that a straight honest story even if not as exciting at times is a bigger turn on, so that is what I will continue to try to give. Read more »

[M/F] – The Tales of My Girlfriend: A Crazy Four Years (Another Story)

As some of you may already know, I posted about a week ago on this sub detailing everything about my slutty girlfriend, Lexy, and some of her stories. If you didn't catch it, please check out my last post. Today I have another story I want to share with all of you. This story isn't very long, but she still gets very embarrassed by it. It takes place around sophomore year of college…

Lexy and some of her friends went out on a Friday night to a small house party. It was no more then 4-5 guys, and the rest were friends of Lexy. It was a pretty typical thing for them to go to a lot of these house parties sophomore year, as they weren't of legal drinking age yet. As the night went on Lexy and her friend Jessica started taking shots with some of the guys at the party. The guys kept telling them that they were too weak to hang with them, but both Jessica and Lexy managed to keep up. Lexy was wearing a black shirt with big slits up both sides. It sort of looked like a tank top if the arm holes went from hip to shoulder. The shirt was tight fitting though, so it covered up her boobs pretty well. But, she wasn't wearing a bra that night, because it would be very noticeable on both sides of the open shirt. One of the guys noticed this and loudly asked if she was wearing anything under her shirt, to which she eagerly replied she wasn't. He then dared her to drink 3 more shots in a row, and if she couldn't do it she had to flash her boobs. Read more »

Late night ass play [m/f]

I should preface this by saying my fiancee has previously said she's okay with me waking her up to sex and that when she doesn't want it, even when she's sleeping, she usually shrugs me off and I stop.

Last night my fiancee and I were in bed. She was asleep and I was in that weird state of groggy tiredness where you can't quite sleep but you're barely awake.

At some point she rolls over, puts her hand on my cheek and gives me a deep, slow kiss. She rolls back over and dozes off while my mind is suddenly very awake. I roll onto my side and reach a hand over to place on her hip and gently start stroking the area. Slowly, i slide my hand to her ass and start stroking and gently squeezing it. It fits perfectly into my hand and just feels so sexy.

She's leaning on her front slightly with her legs parted and I start to run my hand up and down her ass, letting my thumb trace from the top of her ass cheeks down the center and lightly grazing over her pussy. She slowly starts to stir at this, sighing and squirming a little. Read more »