Category: gonewildstories

The time I (accidentally) kept a crossdresser in chastity for over 50 days [M27, T23]

This story took place in June, July and August 2015. It was between myself and a crossdresser I’ve been meeting for a few years. She’s called Kyla – and I might as well shout out to her as she’ll be reading this story. If you have any questions for her, post below and I’ll try my best to get an answer. Kyla is 23 in this story and crossdresses only part time, really as an outlet. We’ve had a few deep meaningful conversations over the years and I’ve learnt that Kyla would transition but for the good things she’s got going in her life. She lives as a male, has a good job, a good family and good prospects. She doesn’t want to rock the boat too much.

I don’t think I could really say I “live” in the UK. I’m usually travelling with work so only spend perhaps ten days per month in England, and sometimes that time is in London hotels as I stopover. I do have a nice house though that I enjoy returning to when I’ve got time. When I return home I also enjoy getting Kyla to come over for a good, lengthy, overnight session. She’ll come already dolled up, will bring an overnight bag and we’ll eat, fuck and sleep until the next morning. Read more »

A perfect trip visiting a friend. (m/f)

Like any other person living in the 21st century, I spend a fair amount of time online. A few years ago, I became friends with some absolutely wonderful people from all over the world, and of course one of those people just had to be a handsome little fucker who lived nearly 4,500 miles away from me. We spent quite a bit of time flirting, at first I tried to be coy and cute but eventually I just unzipped my Batman onesie and sent him a topless snapchat. That’s what every guy wants, right?

Thankfully Sam felt the same about me, and we spent a lot of time seeing each other’s naked bodies and talking about what we wanted to do with those bodies. Occasionally he’d start seeing someone, or I would, and we’d back off and just be friendly, but when we were both single again we could always just pick up where we left off. The cycle continued like that for a couple years until I decided I needed to actually touch him, feel him, taste him… I started saving my money and in just six months I had enough to visit him. I ate a lot of ramen in those six months. Read more »

College Orientation [M/F]

I’ve browsed this sub for a while and figured I would finally contribute some material. I’m graduating from college in May and was thinking about some of the times I have had over the course of my career and thought others might like to hear them. The first memory is about my time as an Orientation Leader at my school. It was an easy gig that paid decent money to essentially just walk kids around campus. Most of these sessions were just day sessions but there were always 2 overnight sessions. This mean kids would stay over on campus and have time to sort of feel out what it’s like to stay there. Luckily for us, we were really only responsible for the kids until 9pm then we could do whatever we wanted. This summer in particular, I had just recently broken up with my GF and she had given me a pretty dumb reason for the breakup so I was on the hunt. Read more »

Story I wrote for my wife.(m/f) nsfw

It had been a long day at work.  John’s legs were tired and the cold wind had cut right through him.  The only thing that was keeping him warm was the thought of his wife’s touch.  It had been a long 16 hour day on the pipeline.  But none of that mattered as it was time roll up the leads and head home.  He hurried to tidy up his tools.  If you had been watching John you would have known he had something on his mind that was making him rush.  Tools were half assed put away and his leads just piled up in a bunch instead of neatly rolled up.  He fired up his Cummins and drove as fast as he could, knowing that his Queen was hot and waiting on him

  Arriving at home he basically bust the door down with his excitement and lust for his wife. He walked in the bedroom to find his wife asleep. Her bare beautiful body on display for him as if she wanted him to find her this was so he would instantly want her.  She was wearing a black see through lace nighty with matching crotch less panties.   He couldn’t help but study her body from head to toe. Read more »

Going to a swingers club tonight!

I’m shaved bare and I have my outfit picked… a sheer black top around the middle with pink lacy halter straps to hold my breasts that you can clearly see my nipples through. My panties are lacy and black and I have some tall sexy pumps to wear.

My bf knows what a slut I am and how much I want him to fuck me in front of others, encourage me to eat pussy and be a toy for other men.

We’re meeting a couple there (from one of my previous stories) and will I’ll be writing up the story tomorrow.

Any requests or suggestions?

Coworker wants to [F]uck [M]e after work. How can I say no?

This girl is amazing. The best kind of coworker, the kind that grazes your dick with their hand as the walk by. The kind that responds with “you” when you ask them “what do you wanna do.” The kind that takes every opportunity to get you hard tease you or turn you on. She is super sexy and more than that she wants me bad.

We have been working together for a while now and we have been close ever since but the other night we had been texting back and forth. Flirting and talking dirty leads to her sending me pictures of her bare naked body, her using her vibrator. She asked me to step away from work so she can see my dick. I obliged. I think I stayed hard all day long. Work was coming to a close and I told her to come by the office after work. She wanted it as bad as me and she simply asked me what time. Read more »

Post-Prom Threesome [F18/M23/F18]

*Prologue*

This story is a solid ten years old. Its origin is from a girl I met on the now mostly defunct onlyundiesclub, basically a profile-based site where guys and girls posted pictures of themselves in their underwear with contact information. When it wasn’t widely known, it was a fucking goldmine.
Anywho, I met a girl we’ll call Katie from OUC. She was a bit on the heavy side, but with gigantic breasts. We’d hung out once before, some fooling around, mostly boobs and blowjobs. As time went on, we’d mostly chat on messengers and the phone. Kind of shifted to more of a friend thing.

*Story*

Katie calls me one afternoon to see if I’m up to anything. Having just graduated college and, due to lack of employment, moving back home to the suburbs left me with not often being up to much.

Katie: “A bunch of my friends are renting a beach house for after prom. I’m going to drive down there later, want to come?”

Me: “Yes.”

Kind of a no brainer, right?

She picks me up and we drive an hour and a half to her friends beach house. Read more »

Asian MILF’s Have The Best Throats (18M/33F)

Straightforwardly, I’m just gonna say, I never fucked someone else before. Until yesterday, I facefucked one of the most beautiful asian MILF in this entire neighborhood.

So, here’s how it started. My dad and mom left the States to somewhere in Asia because of work purposes. So, I was left in the house with only my older sister. Just this one fine morning, my sister had to go to an extra class for 3 hours. I told her to give her teacher an excuse to staying home because as a brother I kinda worried letting her walk by herself on the streets. “Come on, find something fun to do. i know you’ll have your fun when I’m gone. You love it when I’m gone.” She said as me and her always quarrel all the time. But she was damn right about the fun I had when she was gone. Read more »