Category: gonewildstories

[M]y Best [F]riend Part 3: Summer Vacation [Long]

Sorry, another long one. Sexy stuff separated out. Again, on mobile. Yada yada yada

Graduation had come and gone. Summer vacation had begun. Emmy was preparing to go to a state college an hour away to major in nursing. I was headed to a technical college to become a mechanic. That summer was kind of like a last hurrah before entering the real world, as it is for many high school graduates.

Our parents were well off, but they lived well below their means. For our graduation present, though, our parents planned a week long Mediterranean cruise. Vacations are still about the only thing they splurge on, and even then they like joint vacations where they split the cost. They aren’t stingy by any means but ended up making sure Emmy and I weren’t spoiled and that we knew the value of a dollar.

Emmy and I got a scare, though, when our parents announced that we’d have our own balcony room. For a brief moment, we shared a look of “do they know?” until they explained that somehow her grandparents managed to have their room transferred to us and that we were adults and they weren’t wanting to deal with us coming and going. They were pretty liberal in that sense. Read more »

Lost Bet with my Buddy’s Wife [MF]

One day I had some business to attend to in a city about three hours from where I lived. I knew a couple that lived there from college, Steve and Sam, who offered their place for me to sleep while I was in the city. They had a guest bedroom in their townhouse which certainly would be better than a hotel. Steve and Sam had been together for about four years and were recently married. I met them after they were already together and they were already completely obsessed with each other. It was cute and I always appreciated the relationship they had.

At the time this story takes place, everyone is about 25 years old (give or take a year or two) and I was single. I always had somewhat of a crush on Sam, she was an attractive girl. About 5’8” blonde with a bombshell body. She looked like a volleyball player with toned legs that led up to a round and tight ass. She had cute perky B or C cups that looked so fun to play with. Read more »

Wasted [m]y 20s just [f]ornicatin’

I have a few stories from my youth. I’ve enjoyed reading the stories posted here and can only lurk for so long before I gotta give back to the community. I’ll give you some set up and then sexy parts. I will be retelling these as accurately as I remember… there may be some gaps and there may be some unsexy parts. Just a heads up. Also fair warning, I used to think I was a writer.

Story #1 is about 15 years ago.

I worked with Claire at our part-time job; she was working while finishing her senior year of High school, and I was just working there while I wasted my 20s partying and hooking up.

WARNING this story includes cheating.

At the time, we were both in relationships with other people. This was not the first time we’d hooked up; we’d tried dating earlier in the year but it didn’t work out and we’d since set up a pretty beneficial friendship. In retrospect, she was crazy about me and I did not treat her as well as she deserved. Read more »

I [M] 20, fucked a 29 year old at work when I was 18…

It started at my first proper job. I woke up in the morning at 7am and got home for about 11pm. I was working my ass off but it was all worth it, seeing her ass in those tight trousers walk upstairs to the café she worked in. Lets call her Sara for the sake of Reddit. Whilst there I had talked to 2 other girls too, but none kept my interest the way she did.

Occasionally she’d come down and ask for me, and she’d give me a coffee just the way I liked it. She was 5’2, brunette, cute face with a perfect body. Her tight trousers and apron strapped around her waist gave it all away. Everyone knew. Occasionally at staff parties she would wear the tightest black dress she could find and linger around me in front of everyone else when she had a bit to drink. She had big brown eyes with a spanish accent to die for. Read more »

[MF] Office Kiss

Lu works down the hall from me, and I’d started fantasizing about her about five minutes after she joined our agency a few months ago.

The sleeveless blouses and tailored slacks she wore to work were just the start of her appeal. Her breasts looked full and heavy, and no other mother of three – including my wife – ever had a tighter looking ass. She had a tiny, barely noticeable scar at the corner of her lip that made her mouth look like it was begging to be kissed. She wore her dark hair pulled back in a ponytail, and sometimes a stray lock would fall across her forehead, and it was all you could do not to reach up and brush it back for her.

Lu had to cross my door to get to that of Cheryl, her team leader on a crucial pitch we were about to make.

After a while, I think she noticed that I always got up immediately, stood in my doorway and watched that lovely behind of hers as she moved briskly down the hall. Read more »

[28F] I fucked a stranger in a shared room, while my friend did the same in the bed beside me. [FM]

Aged nineteen I went on a – to not mince words about it – drunken fuck-fest of a holiday to Ayia Napa with some university friends. This is technically a continuation of [this](https://www.reddit.com/r/gonewildstories/comments/gmqqv4/i_28f_participated_in_a_blowjob_race_while_on/) post, but can be read in isolation and without the need for earlier context.

NIGHT THREE.

By the third day we’d all just about acclimatised to the new day/night cycle. A few of us were managing to wake early enough in the mid-afternoon to actually see the sun, but the near constant hangover-haze prevented us from doing anything more exciting than sitting and hopping to find ourselves catching a lovely bronze glow, rather than the pasty-to-near-pale-blue of our natural skin tone. (Well, mine. One of my friends looked near permanently radiant. Bitch.)

We’d agreed to have a somewhat quieter third evening. There’d still be plenty of drinking, dancing and potential for some debauchery, but it was to be much more low-key than our previous night, in that we weren’t going to spend hours killing karaoke, nor were we intending to find ourselves in a decidedly seedy bar failing to win any dubious ‘competitions’. Read more »

The Time [M]y GF’s [F]riend Caught us Fucking and Stayed to Play

Like many new couples, the early days/weeks/months of our relationship was very hot and very sexual. We fucked every day, sometimes many times per day, pretty much any free time we had together was spent all over each other. We talked about fantasies that we each had, we talked about past experiences with other partners, and even things we still wanted to do. She told me about a hot college experience she had with a MF couple and I told her about some of my past experiences, how I had shared my ex with a friend of mine, and how I had been the extra guy in a few MFM threesomes. She was pretty shocked that I had been okay sharing my ex with another guy. She was more surprised that I was more than “okay” but that I loved it and fantasized about her like that. Over the next few months we would talk about it every now and then, or I’d make a “joke” about my friend and I having our way with her or how I wanted us to be watched when we were fucking. She’d smile and laugh at the “joke,” but she knew that I was serious, and it was starting to turn her on thinking of it. Our 4th floor condo had a huge sunroom and she’d often walk around the condo topless or naked because we were high enough up that people on the ground floor couldn’t see in. It was a really small one-bedroom condo, so space was very limited. I made the sunroom a walk-in closet for her, so she’d be in there working out, doing yoga, changing clothes, etc. However, if someone was in the sunroom, they could definitely be seen by people on the ground or in the adjacent building, especially if they knew where to look. I loved seeing her laying out naked in the sunroom, knowing that she was slightly on display and that some lucky people could look in and see her. One night we came in late from a night of drinking, I led her into the sunroom and removed her clothes. I put her naked body up against the windows, so that her tits were pushed up against the window, exposing her to anyone that happened to look up and I fucked her up against that window, not knowing who could see, but excited knowing that someone could. The next morning, I looked over to the sunroom and could see the smudges on the windows, leftover evidence that her tits had been smashed against the window as she was getting pounded against it. I asked her not to clean off the window yet, just so I could remember the night for a while. Read more »

A Late Bloomer And A Christian: My First Sexual Experience At 22 Was Quite Different Than I Expected [MF]

Welp, here goes nothing. We were both of age when this happened, and names are changed to protect the not-so-innocent ;) If you want a good story, read the whole thing. If you only want the sexy bits (been there, I get it), skip to *SEXY STUFF*

Background:

I’m a Christian. I know, not a sentence you’d expect this kind of story to start off with (for those who aren’t familiar, sex outside of marriage in most Christian circles is considered a BIG no-no). I love Jesus but don’t go around judging people if they do something I disagree with. But I grew up very conservative, and while some of my views have shifted (IE: I believe you can look at nude photos and be respectful of the subject’s personhood. I enjoy commenting on Gonewild photos and telling the posters they’re beautiful), I still believe that sex outside of marriage is wrong. Butttt I still went there. More on that in a bit. Read more »

I [M] ended up fucking my new roommate [F] after hanging out at the Strip Club. And Damn did I regret it.

I used to live in a five bedroom apartment in a big city. We had a rotating company of roommates, many who I found through Facebook connections and your occasional Craigslist hit. It was co-ed but everyone range between 23-33. It was a diverse group of people and while it may seem crowded, we actually all barely saw each other half worked in the service industry, while the other half worked on their residency in the nearby hospital. We were all friendly but there was an unspoken rule of “try not to fuck your roommate, physically, financially, emotionally etc.” I was the only one on the lease so everyone pretty much paid me so I was responsible for also vetting prospects. A roommate was leaving to work in a lab two hours away so I had to fill the spot. There were some great prospects but I posted a search on FB and someone had recommended a friend of a friend named Sarah. Coincidently, I’d work on a project in which Sarah was assistant number two to the principle talent and we had some brief interactions. She’s the quintessential “Chill girl” her hobbies included smoking weed, knitting and listening to music. Physically, I’d say she’s 5’6 tan skin, small b cup breasts and a gorgeous robust bootie. Her celebrity doppleganer would most aptly be 75% Aubrey Plaza. Read more »