The Sexual Awakening of Polly Pinnick, Pt 1 (FM, Cheating, Risky, Oral)

I lost my virginity to Nick when I was eighteen and for months I wondered what all the fuss was about.

He was my first proper boyfriend, the first one I’d brought home to meet my parents, and that first time in my empty home, with my parents out with my brother and sister, we had painful and awkward sex. It had been something he’d been pressuring me for months, and as time had passed I had gotten increasingly excited about the experience I was about to share. Friends had spoken of sex as this wonderful moment of bliss, of connection with the person you loved.

Instead I just remembered wondering whether that was it.

Reading stories online had told me that it was something that would get better, that lovers learned each others bodies as time went on. But while we kept doing things together, each time I didn’t ever feel myself get close to orgasm, and that awkwardness never seemed to pass even as time stretched on.

[MF] It’s cold outside so I’ll reminisce about summer

I was out on a date at a popular park with THE girl. No, not the one that becomes your happily ever after. I’m talking about the one that will forever make you horny as hell for her. It was a hot summer day with the sun out making everyone sweat. She is one of the hottest girls I’ve ever been with. About 5’2” and 125-130 lbs. Just so perfect, a flat tummy but with meaty thighs, a jiggly ass, and D cups that were soft and perky. Despite her amazing body, the best part about her was her face. She was very cute. Round face, thick lips, big smile, and mischievous eyes that would make me insta-hard anytime she wanted. She was always very horny and very spontaneous.

[FM] My first time with my favorite fuck buddy

I’ve recently reconnected with my first and favorite fuckbuddy after years of not talking. Since we’ve reconnected, I’ve been thinking about all our adventures, and I couldn’t think of a better place to share these adventures than on here!

I met him on myspace, like at the tail end of the myspace era. I was a freshman in highschool, but I looked pretty much the same as I do now — big boobs, curves, and hips. A friend of mine had recently added this guy I found very attractive and so I also did that. We started talking and realized that we had a connection. After talking, we both decided that we didn’t want a relationship, but we’d love to hook-up. He was older than me, I was a freshman in Highschool, and I believe he was a senior, or he had just graduated I can’t remember. He had a ton of girls going after him, so the fact that he wanted to have sex with me blew my mind.

Not erotic just me being an idiot

It all started last year at work the flirty comments, the checking her out without her noticing, nothing could happen as we both were with other people, but I would see her walk into work and my face would light up, I would learn everything I could about her whilst I could, staff don’t generally last too long at our place so I savoured every moment I could. 

Late on last year we both finally admitted that there was something between us but nothing was acted upon, though there was many a time that I wanted to take her in my arms and kiss her passionately, something I longed to do. But out of nowhere our shift pattern changed and we didn’t get to see each other, I spent that time wondering if she still had that little spark for me. 

ICYMI – Exploring the Mysteries of Belle +bonus backstory

*Story background*:

I met Belle on a cam site. Among other things, we chatted about my writing hobby. She asked if I could write a story for her. She gave me this prompt:

>We are in a theatre. I know the manager. We have sex there.

It was still summer when I started writing and I wanted to make more of a complete date, so I imagined the walk to the cafe in an unnamed European city to start. I wasn’t sure how it would end, but walking home from a cafe seemed appropriate. The entire duration covered in the seven scenes is 10-12 hours.

Belle always impressed as someone with an artist’s soul. I imagined her seeing every expression as art. You see it in her doodling on the place mat in the first scene.

Another online acquaintance happens to own a theatre. Her online persona is dominatrix. I asked if she would like me to write her in. She was the idea behind Lilith. Everything in the story was imagined as I let the characters come to life.

Published
Categorized as Erotica

Hidden Pleasures (Chapter 1) [FM] [FF] [mast] [oral]

This is the first in a series of stories. It was never meant to be more than a one off, but I enjoyed the writing process and wanted to expand the story further. Each story can be read separately, but like any series, I feel they should be read in the correct order to fully enjoy and understand the characters and what role they play.

Any comments are welcome and I hope you enjoy.

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Hidden Pleasures

Train Trip, Part 2: One Night in New York with Finance Exec [MF]

Not sure if Part 3 of this will get written or not, since that encounter is hard to make a good story out of, but wanted to get this one up:

After making it out of Chicago on time ([https://www.reddit.com/r/gonewildstories/comments/adhz2d/train_trip_part_1_one_day_in_chicago_with/](https://www.reddit.com/r/gonewildstories/comments/adhz2d/train_trip_part_1_one_day_in_chicago_with/)) my trip was feeling pretty worthwhile so far. I spent the evening making small talk with a Russian woman who worked in “massage”, then fell asleep for the night before hanging out in the lounge car the next morning. We were running hours late. I was told that at least in those days, every freight carrier had priority and we had to stop to let each one pass, so what should have been an early afternoon arrival with plenty of free time turned into sunset.

Still, I made it. On the way out of Penn Station to Maria’s place in Chelsea, I decided to stop for a bottle of wine as a gift. I wasn’t sure if that was the right move or not, but it’d been a year since we’d really talked, and it felt important to make an impression on an accomplished older woman. I texted her to let her know I was on my way, then rang the buzzer when I got there.

[FM] That time I found a job as a ‘maid with benefits’

This is my first post in this sub, so bear with me :) It happened a few years ago back when I would clean people’s homes for them. Normally I’d show up at a rough time for people, make sure their homes were nice and clean once or twice a week, then move on to the next house. Pretty common and dull.

One day I’m browsing for listings and there’s this one post that catches my eye. This guy is looking for someone to come and clean up twice a week, seems standard, but…paying higher than you’d expect. Then his criteria is different than normal. “Open-minded. Confident. Requires interview. Dress to impress.” Seems a little over the top for a cleaning gig but the money meant I couldn’t really ignore it, plus I was intrigued. So I met him for the interview at a cafe, in a very [dress to impress kind of outfit](https://i.imgur.com/xG84gJd.jpg). He was mid 50s, fairly handsome. Nothing crazy, but well kept. Turns out he was recently divorced and too busy with his own work to really look after the house. But he didn’t just want a regular maid. He wanted something to ‘enjoy’ while they worked. I had a feeling going into it, but he made several hints as to ‘putting on a show’ while I cleaned, as such. At no point did he directly state or request anything clear, I’m not sure if he was nervous about asking only to have some crazy feminist sue him or something. But I played along, feeling a little scandalous at the idea, and took the job.

Sunday Night Football [MMF] [exhibitionism]

My best friend from high school is still my best friend today. He’s married with three daughters. He was over at our house one Sunday night to watch the Sunday Night Football game (and escape the estrogen of two teenage daughters and a tween). That happened from time to time, and was not in and of itself an unusual occurrence. This was the Sunday heading in to Veteran’s Day on Monday. He and I were taking the holiday off, so the beer was flowing a little more freely than usual.

My wife wasn’t taking the holiday, so at halftime she excused herself and went on to bed.

My friend has had a crush on my wife since high school. They went out on one date back then, and she really wasn’t interested in pursuing anything more than that. But he still carries that torch to this day. His wife looked a lot like my wife in college, but the intervening years and three pregnancies have not been kind to her. They’re down to what could best be described as semi-annual sex with blowjobs on special occasions.

With my wife safely in bed and the bedroom door closed, the third quarter and fourth beers got underway.

Drunken Adventure with a lesbian couple [MFF]

When I was in my early 20’s I worked with a 19 year old woman. We would chat from time to time – nothing particularly deep or even personal, but I was definitely starting to crush on her. What I didn’t realize at first is that she was a lesbian, until one day my dense self noticed the lingering hand touches that she shared with her friend who visited our work from time to time.

Over the next few months I became really good friends with both of them. They lived together, fairly close to where we worked, and I would often find myself in their apartment having a few beers with them. We ended up being very open about our sexualities, but while we talked about what we had done, and who with, what we liked, it was always on a philosophical level. Except for the time when we had a “blow job contest” with long neck beer bottles. The lesbian and straight guy won that for some reason. I would sit apart from them, they were totally into each other, but just in a fully clothed PDA around friends kind of way. I knew the girlfriend, “L” for lesbian, had only ever been with other girls, but my friend, “B” for bisexual, had a streak of sleeping with men before having met L.