Category: gonewildstories

The night I got incredibly lucky and lost my virginity [MF]

When it comes to my early sex life, I like to think I got by on sheer, dumb luck. I was an awkward kid in high school into early adulthood, not bad to look at, and pretty funny, but also weird, shy, and not very fashionable. So imagine my surprise when I lucked up and got myself a smoking-hot girlfriend my junior year, whom I’ll call Carina. She was 5’2”, medium-brown complexion, lithe figure, nice tits, and later, a tattoo on her lower back.

Long story short, I fell for her hard. When we broke up, I went to pieces. I was a mess. I spent that summer out of the country with relatives and came back with my head on straight and ready to move on. After I graduated, I got my first job at a department store and was getting ready to start college on a scholarship. All in all, things were looking up.

Then one day, I got a phone call. It was Carina, looking to reconnect. She extended an open invite to hang out at her place, anytime. Literally anytime. In my naïveté, I thought nothing of it other than she was trying to be friendly. Yes, I was once that clueless. Read more »

mischievous checkout chick [MF]

I should set the background of this story. I was working for a supermarket chain at the time that i couldnt stand being at, so i didnt really care about what I was doing day to day. Im a younger guy, what do younger guys tend to do? Anything sexual.

So there was this cute girl that would work the checkout most mornings during the week, 4 years younger than me, legal by a few months. I would always catch her staring at me. So i thought fuck it, il flirt in the mornings a little bit and lay some ground work. It didnt take very long for some teasing to happen and some not so safe for work things started to happen.

Now, we worked in quite a small local supermarket. Open some weird hours, not a lot of staff on. So we would try to catch each other up stairs in the offices with nobody around to catch us out (as id previously been caught having sexual relations with a staff member at a different store i worked at, being the reason i got moved to the one where all these proceedings went down) Read more »

I love giving my boyfriend road head… this time, we almost got caught [MF]

Hey y’all, this is a separate account from my main one for obvious reasons. I wanted to be able to post some of my crazy sex stories since me and my boyfriend are pretty adventurous to say the least. I have a bunch of these so let me know if you guys enjoyed this one and want to hear more.

My boyfriend (22) and I (20) have been together for about 5 months now officially, but we liked each other and we’re best friends for a long time before that. There had been so much sexual tension that when we finally fucked it was phenomenal and we haven’t been able to stop since then. We have sex or do sexual things almost every single day and it has not slowed down since we first started dating.

I have a very high sex drive and he definitely keeps up. Usually, he teases me for a few days before letting me cum, that way I’ll be desperate for a while and when he finally does give me an orgasm it’s one of those super intense ones where I’m flailing and screaming and can barely walk afterwards. Read more »

Unexpected [MFM] from a Craigslist hookup many years ago

This origins of this encounter go back a while and I don’t really want to bore you with the details (at least not this early on). Put simply, I had been broken up with and I had a lot of demands that I wanted met for my own personal gratification before I could commit to another relationship. This is the story of one such instance.

I had swapped emails with what I assumed (correctly) was a woman on the now defunct Craig’s List personals. She was looking for a guy. I could tell by the word choices that she was a real person. She used the word groovy once… that pretty much sealed the deal for me. We met, had quality sex and when I was cleaning up, I noticed she had some other condoms in the bathroom trashcan. When I came out of the shower, I asked how many others had accepted her invitation. She said it had been “worth her efforts.”

“Why not call one of them, see if they’re not too busy,” I said. I had wanted a threesome, but instead of with two women, I wanted it a woman and another man. There were certain things that two men can do that two women simply cannot. Read more »

[FM] I travelled for 2 hours to get fucked in a park at 10 a.m.

Originally posted this elsewhere but it got removed, so I’m hoping GWS is a better home for it.

Here’s a story about [a guy called J](https://www.reddit.com/user/deeprixx) (25M) and what is probably the most effort I’ve put in for nothing but abuse in return. Side note: I’m exploring masochism, I got hit really hard and J is kinky/mean, if that’s not your thing you may not enjoy this. I may well post more because god knows I have a few stories.

I responded to J’s ad on my local r4r sub looking for girls who got turned on at the idea of torture. Yeah, I knew what I was getting into. We met up for a casual drink so I could check he wasn’t catfishing me or a creep (he was actually weirdly shy, it was kind of sweet). We got along, and basically established next time we saw each other I’d be getting abused. Read more »

Tales of A [MF]

We met in March, all professional and polite.

She climbed into my bed in June, when we worked together in Spain. A late night after a festival, sharing a room in a hostel in a back street of San Sebastian. She said she needed a hug, but it soon became more. Caresses turned to kisses, to tongues exploring, to fucking until the city was quiet and our early morning start seemed dangerously close. Half a day later she was gone, on to Paris and beyond, while I went South then back to London.

In October we found each other in Croatia, in a beachside hotel out of season. An afternoon of billowing curtains, lapping waves, tenderness and slow, languid lovemaking. A walk on the beach, a restaurant and falling asleep in each others’ arms. 2 days later she was gone again.

I saw her again in London, she’d met someone else.

Sex All Over Savannah [MF]

So I’ve decided I’m going to write out some of my stories of my “glory day” as a way of remembering and confidence boosting.

This story will be about one of the adventures I had with my FWB at the time. We will call her Rae. So Rae was a college junior (22), fun sized at 5’0 and curvy/thick. She had amazing 32DD natural breasts and an ass to match. Her brown eyes and brown hair gave her a natural submissive look, but her attitude and charm radiated pure sex. Unbeknownst to me, she was actually a Cam-Girl when I met her. I had just gotten out of college after the Army, and still bartended because bartending downtown Savannah is an addicting, profitable profession (tourism money mixed with drunken college girl attention…most guys wouldn’t be able to say no either). I’m 5’9 and my dad bod was just starting to show up at that time. I have blonde (some would say red) hair and dark blue eyes. My beard was at its biggest at the time. I think that’s a solid description. Read more »

[MF] She asked me if I would fuck her friend and cheer her up.. [public][breakup]

I was friends with these 2 sisters for a while when I was younger. I always wanted to have sex with the younger prettier one but I eventually ended up having a fair amount of sex with the older not as pretty one. They were both super cool and looks honestly don’t mean a lot to me so that was fine. This story is about the older one and a friend of hers that just needed to get fucked.

It was summer time. Before I had ever did anything more than kiss this girl. She had a friend who was recently out of a crappy relationship and just needed a brain break and to feel good and sexy. So naturally she thought of me. She texted me and explained the situation and asked if I would be down with hooking up with her friend. I, of course, said I would love to. Now you may think it’s just because obviously I’m getting to fuck, so yea I’m down, but it genuinely meant more to me that A.) This girl thought of me when her friend said she needed to feel sexy and wanted and B.) I get the opportunity to cheer someone up and make them feel awesome. It was more about making her feel good than me. Read more »

Spontaneous meeting and fuck in the parking garage [MF]

It started out as a pretty standard night. Went out with some friends, had a few drinks, but I didn’t manage to meet anyone special. Since most of my friends had significant others or fwb, they decided to call it a night. Being single, and new to the city, I was a little dissapointed, but walked slowly toward my car.

As I waited at a crosswalk for the light to turn a girl in black leggings, a shortish skirt, and a tight tank top strolled up. I drank all of her in as I gave her the obligatory 1/4 second top to bottom glance, and noticed her doing the same to me. To my delight, I felt her glance linger just a little longer that usual.

In my tipsy state, I took this as an invitation to start a conversation and said “hey there” or something like that. She responded with a cheery “hi!”. Read more »

Going to the limit with an anal toy 28[M]

I learned early on that I had a thing for anal play when I was young and accidentally slipped a soapy finger up my own ass in the shower. I was shocked that it happened and more shocked that I enjoyed the way it felt. I was even more surprised, years later, at how much I enjoyed it when a friend I’d been experimenting with asked me if he could fuck me. After a disastrous first try, we did it again and I couldn’t believe how much I loved it (no details on that here, as we were in high school–hee hee).

So a few years ago, I decided to indulge my own love of anal penetration privately and set out to buy a butt plug to play with on my own. Admittedly, I got greedy with my first purchase and bought one that was way too big. At it’s base, it was probably six inches wide. The first time I lubed it up and started to slide it inside me, I could tell I’d been overly ambitious. Read more »