gonewildstories Archives — Page 4332 of 5640 — NSFW story

[FM] My first time with a stranger in a public restroom

It happened on Monday but I haven’t had time to write about it until now. A few readers from my previous posts asked me to go into more detail with my next post so here it is:

Monday morning I received a long story from a guy (based in the southern US) I’d been chatting with on Reddit about how he wanted to force impregnate me. It was a huge turn on, and especially so because I’d been horny all weekend. I was meant to meet someone on Sunday for an intimate encounter but he didn’t turn up. On Monday I really needed it badly.

Since my first post a couple weeks ago I’d received a lot of messages, about a third from guys who are in my city of Shanghai. So on Monday morning I asked one guy, an American fitness instructor, asking him if he was available to come to my building for sex. We’d chatted on and off for more than a week about what we liked. He had a great body judging from the photos he sent me and I knew his time was more flexible on account of his job. Read more »

[MF] Sexy Time with Kat

After I got my education, career, and finances in order, I started dating. A lot. Between 2001 and 2006 I had a *lot* of sex. To this day it’s astounding because I’m a pretty gawky guy and I like to keep to myself; plus I’m bookish on top of it all.

Kat (not her real name) and I had been out a few times. We’d been introduced by the matchmaking wife of a friend of mine, and between my aloofness and her recent divorce we were paired “just because”. I liked Kat, but what I’d known about her divorce was a lot to take in — in particular because I had never been engaged or married.

Our first few dates were fun and enjoyable. Kat was extremely tall (6′) and as I am extremely tall she would always wear these hot high-heeled shoes that she’d been saving up for “the tall man of her dreams”. I remain delighted by a woman in heels, and she was delighted to be able to wear them with a guy that she wouldn’t tower over.

Getting Lucky with My Housekeeper [MF]

So I live in a pretty wealthy family with both my parents working. Because we have a big house and both my parents are busy with work, we hired a housekeeper or maid to take care of things around the house. She comes M-F to cook, clean, do laundry, etc. We’ll call her Maria. My parents and I both, while busy with work, actually work at home. Therefore, we have grown close to her. She will come over for Thanksgiving, Christmas, etc. She’s basically a part of the family.

At the same time, I’ve been attracted to Maria for a while. She’s a bit older than me, probably being in her late 40s while I’m 28. However, she has a great body. Her best feature is her ass which I have started at for years now. She and I have grown close as well. We would message on WhatsApp and she has sent me plenty of dirty jokes that she has received from her friends. We’ve talked a bit about sex and she’s pretty open about it. However, she was married so I didn’t try too much. I may have tried flirting a bit but that’s about it. About a month ago though, I found out that she’s getting divorced. However, with the age difference and the fact that she works for us, I didn’t really think anything will come of it… until. Read more »

First Time Crossdressing For A Man [TM]

Hello everyone,

This is a crosspost r/gaystoriesgonewild. I’ve been a lurker here and have a few stories of my own that I could share but never have. I got a pretty good response on the above sub so I figured I would post here too! ? what follows is copied from the original post:

Now I know that the whole sissy fetish isn’t for everyone in this sub, or even really that accepted in the gay community at times. That being said, for me, the appeal to the sissy fetish is much more about the humiliation aspect of the kink than anything else. As this story will explain, I never knew how much I really enjoyed being so submissive.

What follows is entirely true, and I will never forget it:

A little about myself. I was 20 years old in college at the time. I was about 165 lbs and 5’9. I had always enjoyed dressing up from an early age. When I was much younger, I vividly remember stumbling upon transsexual porn and becoming instantly infatuated. I found myself wanting to dress up and wear sexy lingerie. When I finally moved out of my parent’s house at 18, all bets were off. I had roommates, but would almost instinctively close the doors to my room every night and slip into some sexy clothes and play with myself. I went to local sex shops and bought tons of outfits over time, dildos, heels, pink chastity, the whole gambit. Read more »

A delightful afternoon in Manila [MFF]

We’ve been very lucky with the people we met over the year. Recently we were in the Dominican Republic and met a hot girl there for a wild MFF (post will follow), and our last experience in Manila was no exception. My wife V (who is Filipina) and myself (Swiss) were spending a few days in Manila. It was supposed to be some vacation before flying to Singapore for work, but I ended up being busy with work anyway and so we took a nice suite in a hotel we like, and I got to working.

We had made plans to meet with Chelsea and spend the evening with her, but unfortunately I had to cancel because of work. Chelsea is really nice and easy going, and was so graceful in understanding the circumstances. She said however that if V wanted to spend time with her the next afternoon, that would be good. Since I was busy, I encouraged V to say yes and maybe go out for coffee and chit chat. Read more »

[MFF] Me & the Swinger Couple

This happened a number of years ago when I was 27 and on vacation in Thailand. I stayed in friendly guesthouse above a bar and befriended the locals expats which used it as a watering hole.

One night, and Irish couple comes in to the bar and the owner knows them from previous trips. Tony and Mary. Tony was a medium build guy with salt and pepper hair and a huge mustache, good humor about him and quite funny, early 50’s. His wife, Mary is in her mid 40s, shoulder length brown hair, brown eyes and think athletic build. Wearing a mini-skirt and button down blouse, half of which are undone revealing a set of huge, perky tits. Her and I make eye contact from across the room and I play it off, she clearly is with Tony. Later on in the evening, we strike up a conversation and she is quite funny and flirtatious.

She takes numerous opportunities to lean far forward when I light her cigarettes to show off her massive cleavage and looks up at me at one point to ensure I am staying straight at her knockers. She asked me if I liked her tits, to which I naturally reply in the affirmative and she notes that she had them lifted last year. Read more »

[F] One week later…

Over the weekend I decided to see if my flat mate had managed to avoid playing with himself for the week, in order to get the prize of a repeat performance. Once everybody else had gone out I knocked on his door, and entered his room. After some quizzing I was satisfied that he had held up to his end of then bargain, meaning I was going to live up to mine. However this time with a twist, as I decided to FaceTime my bf so he could watch me be a good little slut.

I dropped to my knees, and took my flat mate into my mouth, making sure to work every inch as best I could, after all I was putting on a show. Every time I felt him getting close, I’d stop, making him wait longer and longer for the release. After about 10 minutes though I knew he wouldn’t be able to hold back, I felt him swell in my mouth and the first couple of ropes shot to the back of my throat, he then pulled out of my mouth and shot what seemed like endless ropes of cum over my face. Once he was done I swallowed what was in my mouth like a good girl, then decided to get myself off in front of my flat mate, with my bf on FaceTime, with my face covered in cum.

[M]e teasing my [F] classmate until she literally begs for my cock (sort of) Part 2

So as continuation of the last part of my classmate sucking me off, I’ll just hide her behind the name Sena. I gave her a nickname because while I ask her permission if I could post this, she said yes as long as I give her a nickname because our friends doesn’t know we do these kinds of stuff together.

So this happened just yesterday, we’re playing some FighterZ on the PC. We were in a stalemate when she made a deal with me. Every time I beat her, she would remove one piece of clothing. So the stalemate continued until I was on my boxers (We were at my place so not wearing that much, she was wearing her favorite V-neck and skimpy shorts) and she was on her panties, She was literally playing without her bra so I can’t focus for shit. Read more »

[mf] using a family friend to get a gf

So this is about the first time I hooked up with my college gf Meg … spoiler no sex but got head and it’s pretty long will post more soon

I was a freshman in college and was visiting home fir my HS homecoming game…. my brother played on the team and I had a few friends in school still do I cane into town Thursday after class hit done around noon

A family friend was a volleyball coach for a rival school of ours so my brother and I went to go watch ( our school was playing theirs and his gf was on our team)

I notice a sexy looking player on the opposing team and asked her name from the coach after the game …. coach k laughs and tells me she’ll be no part of my shenanigans and to steer clear of Meg …. ( 5’2 tight ass athletic body and c/d cup breast) dark brown hair with red and black underneath and best part she just turned 18 a few days prior Read more »