gonewildstories Archives — Page 3272 of 5640 — NSFW story

[M]y Sexual Chronicles – My [F]irst cheating MILF after my breakup

*Hi. So I’m attempting to write an entire timeline of all of my sexual partners. I know it’s an undertaking, so bare with me. I’m doing everything I can to remember everything in order and accurately without embellishing. Some stories may be boring! I am 6’0, always have been skinny, now athletic, dark hair, white but darker skinned, and horny.*

My displeasure and resentment of Sofia took some time to subside. At the time I worked in a facility that had individuals working in windowless offices by themselves for entire shifts. It was just the nature of the job. I frequently took on overtime and worked Saturdays and Sundays at any hour requested. There was a lady named Jane, and she had the same mindset as me, working as much as possible. I later learned that she was bored of her husband and kids and wanted to get out of the house. This is a story about the oblivious 19 year old who got fucked by the 50 year old married woman. Read more »

[MF] I Had a Summer Romance with an 18 Year Old Woman when I was 33

This story is true, and is a tribute to [this fantastic story](https://www.reddit.com/r/gonewildstories/comments/el4zrv/the_first_time_i_let_a_guy_cum_inside_fm/) about a woman and her first cum inside by a guy. Plus a couple of people messaged me to ask for more details. In no way do I intend to steal that author’s thunder… in particular because there was a *lot* of thunder in her writing. :-)

Update 2020-01-09 : Looks like they deleted the story. That’s a shame!

Note that names have been changed.

Between the time I was 28 and 33/34 I went through this phase where *all* of my relationships were sexual in nature. I was a late bloomer; what can I say? Even though I’d had relationships that involved sex, it was not until I was honest with myself about having sexual interests that were against the norm that I was able to relax and enjoy this part of myself.

Adult websites such as Adultfriendfinder and SwingLifeStyle as well as the craigslist “casual encounters” had come online a few years earlier, and brought a lot of bounty in terms of meeting couples for threesomes or for MILF hunting (there was a time in my life where MILFs and I *weren’t* the same age ;-) ). Read more »

Gentle[M}en pre[f]er Blondes

[m] Back in my college, sophomore year I dated Zara [f] a local chick who was nothing special. Permed shoulder length dirty blonde hair, 34B boobs, with a fair old landing strip. I met her at a bar that I used to bounce at. Her stepdad was a dirty cop who’d been thrown off the police force over some shady incidents. Nevertheless, my one-eyed monster gave in, and after clocking off for the night, I ended up at a club that she hinted she’d be at, and low and behold, there she was, ready and waiting for my arrival.

A few cold beers later, I was in the back of a cab heading home with her skirt half-way up her legs and my hand working its way up to her moist slit. She had a thong on, so I needed to navigate this for finger entry, while not giving the cab driver a free show. By now my cock was solid and moist, and she started to get a feel for it. Once we got dropped off, I took no hesitation in taking her upstairs, ripping off her clothes, and marveling at the spectacle of her taking my rock-solid wet cock into her mouth. Read more »

Traveling 4 hours for [M]aster to dominate me and [F] me senseless

Session #2 with Master

Finally I am able to make time to make the trip 4 hours south to see my master. We both run busy schedules so being fuck buddies with the distance makes it tricky. I drive straight down after I got off work. My pussy was throbbing with each mile I took to get to my destination. I edged myself on and off the entire drive. Just to the point where I wanted to cum but wouldn’t. I was saving every bit of me for him.

I get to the room. Shower up. Make sure I’m good and ready for him. Make up is good. Hair is pulled back. And then I hear him pull into the parking lot of the hotel. Instantly my pussy is wet again. My heart pounds a bit in my chest with excitement. I need to feel him in my mouth. I need to worship that beautiful cock. Read more »

Helping a friend move on from her ex and get back at him a little [FF] [FM]

I was 27 and had been dating my now husband, Ryan, for a little over a year. We clicked so well, our relationship really blossomed quickly. One night, I got a call from my friend Vanessa. I couldn’t understand anything she was saying. All I heard was crying. I told her to just come over and we’ll try and work out whatever was wrong. When she arrived, her face was a mess. She’d been crying for awhile. We sat on the couch and I asked her what happened. She told me that her boyfriend had broken up with her, despite proposing to her just a few months ago. His reason was that he found someone else and was sure *she* was the one. Their apartment was also under his name. So he had requested that she move out soon. She was devastated. She lost her fiance and is about to have nowhere to stay. I felt bad for her, so I suggested she stay with us. Ryan had an office room that he didn’t use too often. I initially wanted to talk to him about it and get his input before making a decision like this, but I wanted to really help a friend. Vanessa smiled and after thinking about it for a bit, she agreed to move in for a few days. She got herself cleaned up and opted to go back to her place to start packing for a few days worth of clothes. After she left, I went into the bedroom and spoke to Ryan about what happened. I confessed that I invited Vanessa to stay with us for a few days and he was supportive of the idea. I was relieved. Part of me worried he’d be upset that I made a decision without talking with him first. Read more »

Fun in the library with the professor [MFM]

A little context first….
We were doing a little role play sexting and I was a professor and she was a student asking for extra help. Being a professional I asked her to meet in a library. But we accidentally met in a private study room were I was meeting with a colleague.

Her:

Well if we’re in the library, maybe I could just bring a couple questions and my textbook. Maybe wear something that catches your eyes, a tight tank top without a bra so my hard nipples poke through. You both catch quick glances as you explain things to me. Maybe your gaze lingers on my perky nipples a little longer. Imagining what they might feel like in your mouth.

I’ll catch him looking at my tight little skirt that rides up a bit when I sit down. Just long enough to cover my bare pussy underneath. Maybe I brush against his leg with mine. Draw him in with my innocent eyes. My perfect lips as he imagines what they might feel like wrapped around his hard cock. Read more »

[M]y [F]irst foray into cheating, with my then housemate at med school. Part #1

Back at medical school, in my first year, my girlfriend and I shared a room in a house with about 4 others – for anonymity let’s call them A, D, L and S. My girlfriend I’ll refer to as G from now on. A, D and L don’t really feature much here as they were oblivious bystanders; the feature of this story is S.

S is younger than I am by around 3 years – at the time I was 25 and she was 22. She is a bigger woman, very curvy but in a way that suits her just right. She carries a huge rack; I never asked the size but they must have been close to watermelons. I had fantasised over these for many months. [Here’s a pic](https://i.imgur.com/dtTWg15.jpg) with a blurred face to give you an idea.

We had all lived together for about 9 months by the onset of this story, working hard and playing hard like the old adage of medical school. S was (and I believe still is) in an open relationship but myself, not so much. I was living with my girlfriend of about half a decade. Whilst G was a good looker, we had a strange distant sort of relationship. It’s hard to explain. Read more »

A life-changing high school blowjob [MF]

Disclaimer: some details have been changed for anonymity’s sake, but the plot and events are all true.

In high school, I was a quiet kid. I was generally well-liked and good looking but never had enough confidence to talk to girls. I hung out in the outskirts of friend groups. My only contact with girls was when I’d get set up for awkward dance pairings with girls on the outskirts of their friend groups. But there was one thing I had in my figurative back pocket and literal front pocket: a big ol’ cock. (Look at my past posts if you want a visual)

I went to a large private high school, so there wasn’t just one “it girl” but a dozen of them. Absolute knockouts. Volleyball players with asses that made my friends and I drool. Girls that went on to model and became trophy wives. But there was one who I’d crushed on for years: Jules. She was a model student who ended up at an Ivy League school and is now a lawyer. Speech and Debate, Newspaper, and star of the soccer team. A blonde, 5’6” spitfire with perky B cups and an ass sculpted from years of soccer and vanity. She was the type who worked hard, took no shit, and got what she wanted. And speaking of wanted, she also had a vicious rumor following her: she liked big cock. Read more »