Category: gonewildstories

AirBnB was our match maker [MF]

Mid last year I went on a 2 month holiday through the Americas. I had just finished up a pretty stressful job after being there for 4 years and had never been overseas in my adult life so I figured now was a perfect time to go somewhere and relax. However I barely met people due to my shy nature. That all changed in the last city I visited, literally in the last few days of the trip.

Most placed I went to I tried to stay in an AirBnb so I could save money on eating out and to do laundry when needed. The last city I visited was Los Angeles. The place I stayed in was a double story house that had been converted into 5 studio apartments. 3 days before I left to go home, I went outside to smoke a joint and noticed 2 girls checking into one of the downstairs apartments, we’ll call them A & V. They were both gorgeous, way more attractive than me (most people are more attractive than a guy with a dad bod). Both were slim with blonde hair, a bit shorter than me and they were both wearing jean shorts to show off their legs. A was more on the skinny side but still looked healthy, V was thicker in the bottom half but not fat. I said Hi to one of them as I walked past and she returned the favour, a minute later she followed me around the corner to introduce herself. Read more »

First Bi & Threesome [MMF]

So I’m married to a wonderful woman who has lost all her sex drive in the last few years. I love her but it’s frustrating. So I have, on the rare occasion, had a little secret playtime when I can.

Last year I messaged a couple from a posting on DoubleList for guy to join them. Has always been a fantasy of mine to do both MFM and FMF threesomes, but my wife is too conservative to try (this has been discussed).

Met this couple for drinks, they didn’t mind keeping my secret, and after I left, they sent me a message to join them the next morning before work. I have also secretly had an oral bi curiosity that I wanted to satisfy and that is how he already was.

Fast forward and we are naked in their bedroom, she invites me to satiate my curiosity. I walk over and stroke him for a little while I work up the courage, drop to my knees, open my mouth and slide his cock in. It was really hot and fun and enjoyed moving my mouth along his cock. It turned her on so much that she laid down and wrapped her lips around my cock. Read more »

[MF] Nice guy finished last. Passed on fucking young MILF

This one is absent or any actual sex, sorry, “MILF” might also be a tad of a stretch. Senior year of college my roommate and I had an apartment literally a block from the main street in town and all the bars. One weekend evening a sorority girl who had graduated came to visit and brought along her friend. Call the sorority girl C. I knew C a little bit and she was even closer with my roommate. Her friend was textbook butter face. No recollection of her name. Some of the details escape me but they ended up hanging out with me and my friends most of the night. I am average looking, overall a loser with girls but sometimes they do like my sense of humor. This girl certainly did and I could see her looking at me. I decided, yes she was fuckable and we started talking. I found out she had a kid back home, was not with the father yada yada. Everyone had had a lot to drink. At one point, the C comes over to me, she’s pretty lit also, and says smiling “don’t fuck my friend!” What are you supposed to say to that, so I basically said nothing. I don’t know if this was her being nosy, jealous, serious, joking or whatever. Read more »

I sucked my brother-in-laws big cock over the holidays. [FM]

Hi y’all,

This past Christmas I sucked my brother-in-laws big cock on New Years Eve. My little sister, who is literally little at 5’1” compared to me at 5’10”, married an old boyfriend of mine from way back in high school. It’s always been a bit weird that I dated him for a couple of months before we broke up, I cheated on him, and many years later he’s dating my sister who is 6 yrs younger than I am. They eventually got married and have had 3 kids.

I fondly remember from high school we fucked non-stop and he had an amazing 8” thick cock that at the time was the biggest cock I’d ever seen, sucked or fucked. I loved it. I always wonder how my little sister could handle it but it sounds like she does just fine. Read more »

Crazy night with a recent HS grad (Long) [MF]

Had the wildest night of my life this weekend and haven’t stopped enjoying it since.

I coach at a small high school and with that I get to know a lot of the local kids in the community. I respect the boundaries and know that there are firm lines you don’t cross, but have always been friendly with all the students I’ve come across. We travel quite a bit by bus and I am always hitting on and talking with the cheerleading coaches so I tend to get to know most cheerleaders too.

I came on a weekend trip back to my alma mater to relive the glory days to help a friend get over a divorce. We got a group together and figured we’d fire up the old flames and show him a good time while also not blowing all his money at a strip club.

At the first bar we went to, I am sitting at the bar talking when I hear a girl freak out next to me. I turn and see Taylor, one of the girls from the cheer squad who graduated the summer prior. I let out an actual, “Holy shit!” Read more »

I [m] slept with a married women

It all started when I got a message on my pornhub account. Didn’t think anything of it so I opened it up and saw a message from a couple that had also added me. They liked what I had posted and wanted to have some fun together. I agreed ( was nervous) and me and the lady in question just kept talking on Snapchat for ages. After a while me and her started talking through FaceTime and that’s when we randomly started getting off watching each other. The fun that was meant to happen went out of the window and she asked me to meet her in London for one night before she went to a work conference meeting. I was up for it , we had like three drinks and went to the hotel and had sex. It was fun as drunk as we was as we kept on drinking after going to the pub. Cut it short I told her husband what happened and she hasn’t had it easy since. Hadn’t spoke as much as we do but recently told me she’s leaving him but she’s actually sleeping with someone else now. Felt guilty at first as it’s someone’s wife but now I’m more pissed off because I’m not having fun with her. She’s good looking too. My luck ran out lol. Milf is such a funny word to describe a mature woman in her 50’s but seriously she didn’t look her age.

[Mf] How my repressed Catholic girlfriend flashed the UPS guy

This is another older story I wrote a while ago but couldn’t post it for… reasons, and I’ll leave it at that. This story takes place over a long period of time. A [Caught] and [Humiliation] story starting from back when my wife and I were in the early days of dating.

***

Back when I was first dating my sexually repressed Catholic girlfriend Chelsea, my place was the ideal meeting spot for our date nights. She often parked her car around the block, sometimes walking up to a half a mile or more just to hide any notion of where she was going or coming from. She even concocted alibi’s and fake reasons for visiting the neighborhood in case anyone asked or recognized her vehicle. The area was well-to-do so the idea of someone potentially knowing her CEO Father or mother wouldn’t be out of the realm of possibilities. Read more »

My [F] 50 first part of my confession

This is my first attempt at writing this story so I hope you all enjoy it.

I’ve been married to the most amazing guy for something pushing 30 years now, he’s given me two wonderful children that have now flown the nest, looked after me in every way and provided everything I could ever wish for. A nice house, a new car every couple of years and holidays all over Europe. Even after all this time I think he’s still the most attractive person in the room.

Our sex life is good, nothing out of the ordinary, but loving and fulfilling. Although after this long a time it takes work to keep it fresh. Occasionally we watch porn together to get us in the mood, nothing too extreme but I can’t say I don’t enjoy watching it together.

After watching something one night that involved a threesome and consuming more than my fair share of white wine my husband asked me if I’d ever thought about having one. Once I’d stopped myself from spitting the wine all over the duvet and stopped laughing I admitted that the thought had crossed my mind, but it was only that…..a thought. Read more »

A sexy, curated orgy to cap off the Year of Orgies! [MF] [MFF] [Group] (Part 2)

[Part 1 Here!](https://www.reddit.com/r/gonewildstories/comments/enhp6f/a_sexy_curated_orgy_to_cap_off_the_year_of_orgies/)

Brief background: Kaylee and I were at a super fun and sexy orgy/play party a couple of weeks ago. In Part 1 I recounted the beginning of the party and my lengthy encounter with the exotic Anna. In this part, I play with the blonde bartender, Maria, and Kaylee and I have a fantastic threesome with our unicorn friend, Stacy as a DP went on beside us on the bed.

***

I came out of the washroom and took some of my stuff to the smaller private bedroom. Since I’d seen the host wife, Scarlet, outside, I figured it was clear for me to go put it with the rest of my things. I cracked the door and peeked inside. No one was having sex, only the bartender unicorn, Maria, on her phone in a lacy and sexy black lingerie set.

“Oh, hi!” she said.

“Do you mind if I put my stuff away?” I asked. “The rest of our things are here.”

“Not at all,” she said with a smile. We’d known each other for a little over a year, and had fucked at a previous party. Read more »

Sex Games. Our Greek adventures Part V [Group]

Link to part IV: https://www.reddit.com/r/gonewildstories/comments/emdvi1/oiled_up_fun_group_our_greek_adventures_part_iv/?utm_medium=android_app&utm_source=share

It had been our last day on the island, on the next one, the four of us were no longer sharing a room, but rather, each couple had their own. It was actually nice, though somewhat sad, to be apart from them, even though they were literally right next door.

We both had a kitchen, but Mona and John had a nice big balcony, whereas Jen and I had just a small one, enough to go have a drink on for the two of us, but not for us four. As such, John’s and Mona’s was the place to hang out. They never even bothered locking the door, we were doing pop ins regularly. Nudity itself had become a complete non issue between the four of us. Once our burns died down, we frequented secluded beaches where it would only be the four of us, and we would let it all out. A couple times we went to legitimate nude beaches too. The sexual tension with that was gone, for all of us. Read more »