How I ended up having anal sex with a girl before PIV (Interracial, Virgins, Long) [m18/f18]

So some disclaimers: this is long and will take a while to get to the sexual stuff. I have changed some superficial details and names to protect identities but otherwise this is a completely true story of my first sexual experiences and how I ended up having anal sex with a girl before I’d had PIV sex. I am not a writer of any description and this is my first attempt at a story so be gentle. Also, be assured that there is no Loch Ness Monster. Look for the break if you want to skip to where things get sexual.

I left high school a virgin. Not just a virgin, but a never been kissed virgin. Girls wouldn’t just turn me down, they seemed to be a bit insulted that I thought I had a chance. I was short, pale, and geeky. I had acne, braces and was painfully shy. I went off to University aged 18 with my acne gone and braces removed. Regardless, I had built up a lot of insecurities about my attractiveness. Girls didn’t seem to be horrified by me anymore but I was still no girl’s fantasy. A solid 5 out of 10. But that was ok, I had long since made peace with the fact that I was no model. My confidence slowly grew from nothing to still almost non-existent but something. I went on a few casual dates and even kissed a couple of girls, but never got any further than that.

[MF] Late night hotel swimming pool – mindblowing oral

This is a bit long, and contains a lot of build up and context. I personally like that in my GWS stories, so I put it in when I’m telling mine, so if you prefer to go straight to the fucking this may not be the one for you. Names and other details inconsequential to the sexy times have been changed, obscured or omitted to protect the parties involved, but other than that, its all true.

My wife and I have a semi-open relationship. It’s not like we’re going around screwing other people all the time, but we’ve both agreed that we can fuck other people should the opportunity arise. This is the tale of such an opportunity.

A few months ago I was away for a work conference over several days. The conference was in a large hotel in the UK countryside. Like a large stately home, with huge grassy gardens and an antique furnished interior. A very beautiful and romantic location, and I was lucky enough to experience a very erotic couple of nights whilst there.

Old pictures of an ex [MF]

The other day I was on the computer and high and just checkin’ all my sites, and I noticed I had a visitor on OKCupid. It was an ex of mine who I hadn’t talked to in a pretty long time. The sex with her was great, but we didn’t really connect beyond that. I did remember something that comes up in my mind often: a time when she texted me pictures of her face as we were sexting. It always struck me as kind of weird. Your face? Why not her tits, which were huge? Anyway, I was stoned and looking at my ex’s profile, scrolling through her pictures and remembering her big pillowy lips have made me cum before.

I decided to check out my text history with her to see if I still had those pictures of, er, her face that she had texted to me. I found something even better: I was surprised to find out she actually *had* sent me some pictures of her tits in addition to her face. Looking at our history I was pretty turned on by the fact that she had been trying so hard to turn me on then. Her efforts had worked, just a year or two later than she’d expected them to! As I was looking at the pics and getting high, my phone buzzed with a text.

How to Discipline a Bitch

There was this guy at work… he was driving me crazy! We were working together on the same project and I was feeling like I couldn’t stand him anymore. He would always second guess my decisions, contradict my opinions, and that arrogant look on his face was the most annoying thing in the world. The fact that he looked like a lingerie model was not helping, either. Our project was bound to be a total failure, and I had been really stressed about it for several weeks.

Even my relationship with Sir was starting to feel the consequences of being around the gorgeous asshole all the time… Sir always makes sure to take the pressure off my shoulders whenever I need it the most, by giving me a well-deserved spanking and then choking me until I cry with His thick cock. But He noticed something serious was going on inside my kinky head this time, so after violently face-fucking me, He took me into His lap and asked me in a gentle voice:

“What’s wrong, little one? You don’t seem like yourself lately.”

“Well…Sir, I don’t want to upset You…”

“You won’t, I’m all ears!”

Rough sex with hot girl next door

I posted another story yesterday, which was my most outrageous experience, but this is the first “holy fuck we’re actually having sex” experience I’d had, so I decided to share it too! Really enjoying this subreddit btw, great stories from our users and great respect from readers!

First some backstory. So, obviously, the hot girl next door is one of the most common sex fantasies, and at first I was sure I’d never ever achieve it. My previous neighbours had a absolutely stunning daughter, who was around 8 years older than I was. At around 15/16 years old, I remember the view of her in her bikini sunbathing in her garden. She had massive, massive tits, and also a nice ass but at that age I only appreciate her fuckable tits. From my window, I had a great view of her incredibly sexy body, but she’d also have a good view of me, so instead I used to go to the 2nd floor room and masturbate over her there. How I wished I could cum all over her belly while she was sunbathing. Up close, she was even sexier, but alas by the time I came to age she was long gone. I had moved out, and she had gotten married (:(), had kids (instant MILF), and moved out too with the rest of her family. I wasn’t home enough to see my new neighbours, who immigrated from Romania, and apparently their household changed around 3 times until last summer.

Pregnancy Risk Edging Game [m/f]

This is a game I played once with a FWB I was seeing for a while several years ago. With most FWB situations, it’s wham bam and you leave. At most you spend the night and get out first thing in the morning or something. But we became good friends over this time. We had a ton in common. We just weren’t in the position or desire of a relationship.

It was one of the most intense sexual times of my life and I’d kill to attempt to repeat it one day with the right person. Who knows..maybe her?

The woman I was messing with and I had come out to each other in having this fetish and we both pretty much admitted that it wasn’t merely a desire to get pregnant that turned us on. While I found the natural changes a woman’s body made to be beautiful, the crux of it all was a lifetime of anxiety in attempts to avoid pregnancy.

My First Time with a Customer, Part 2: He rented a car, I gave him my body…now with coffee and hot showers!) (Jen & Rob) (M/F)

**[Part 1 is over here!](https://redd.it/4s8exm)**

Welcome back to my week of crazy erotic adventure! I have to start off by saying a HUGE thank you to everyone who read my first part and left nice comments about enjoying the story and liking my writing, especially those who encouraged me to continue. I’ve never written a story like this, so I never in a million years expected that post to get such an enthusiastic response. Your feedback and encouragement made me really excited about writing more and sharing with you all… as I still can’t believe the situation I’m in with this sexy man, and posting here and talking about it with you all somehow makes it more real. I really hope you enjoy this one too!

With that, onward to ~~Saturday!~~ Friday Night Part 2, and THEN Saturday (morning)!

*****
**Friday Night**

So Rob and I spent Friday night together at his hotel. After we finished the first time (previous post), we laid together and talked and cuddled a lot. I kept thinking about everything (I do that) and wondering how much to tell him about how new this all was to me. I’m kind of dense because he already knew. It was obvious. I’d told him myself! But I kept feeling like I had to play the part of this sexy, worldly woman who is no stranger to casual affairs with strangers. I’m not… not very bright sometimes.

SECOND UPDATE: Fucked the work experience girl yet again [M35/F18]

[ORIGINAL POST](https://www.reddit.com/r/gonewildstories/comments/4q9m5z/fucked_the_work_experience_girl_last_weekend/)

*tldr: After striking up a friendship with the work experience girl (Laura), I gave her my number (at great risk) during her last day at the office. Turns out that she also had a crush on me, and incidentally was a horny sex freak. That weekend we had sex all night in a budget hotel room.*

—–

[FIRST UPDATE](https://www.reddit.com/r/gonewildstories/comments/4rc828/update_fucked_the_work_experience_girl_again_last/)

*tldr: We went on a dinner date. I didn’t enjoy it much due to anxiety from the perceived judgement of being seen with such a young girl. Despite that, we ended the night by having intense sex in the back seat of my car. She revealed that she was heavily into the “daddy” kink, and also told me that she loved me during sex.*

—–

 

I didn’t plan on doing an update until at least early next week, but the last few days have been CRAZY so I had to get this written down straight away, both to help me to process and because so many people have requested updates. I’m not sure if there’s any etiquette with how often I should be posting, but I figure if you guys get bored of hearing about my drama then you’ll stop upvoting and commenting.

Months of patience, waiting, and hoping, and I [21M] finally put it in her [19F] (LONG)

Good morning readers of /r/gonewildstories! I never thought I’d have a story that was worth posting here to share with you guys. Luckily for us, that has changed. Screw the names, screw the long backstory, let’s get right into it.

So question for you, men of /r/gonewildstories. Have you ever had a history with a girl, and wanted her so badly for so long, your hope of ever fucking her brains out was thinning away? Night after night, week after week imagining yourself with them…touching her, feeling her soft skin, her hair between your fingers, the warmth of her body in your palms? Flooding your field of view with her bright face and eyes as you swap DNA, running your hands up her shirt until you feel the two golden hills? The temperature continues to rise until she whispers in your ear “I need you inside me.” And then you cum in your hand, aaaaand it’s over. Well, not today. I finally, finally got the real deal (and I want more).

Unexpected Coworker (M/F)

I had recently taken to working out at the company gym. I was able to beat traffic, it was free and most of all, it was part of my making changes. I had amicably ended things with my fiancee. I was offered a job in another state that was far too good to pass up. She had reasons why should couldn’t leave. That was the end of that. Few people took advantage of the gym and despite thousands of people working for the company, there were never more than a dozen people working out in the morning.

Sheryl was the girlfriend of a co-worker, Rob. She was there every singe day and while we were certainly were friendly before, we became even more so and often ate breakfast together, another company perk for our division. Everyone knew I was going to take the new job, but they didn’t know I wouldn’t be taking Paula, my now ex. Cheryl was one of the first people at work that I told of the break and she correctly guessed that it was the reason for my change in routine. She was permanently upbeat, a touch nerdy and genuine.