Category: gonewildstories

Lost my virginity to an older woman [MF]

This just happened yesterday and I just need to tell someone, so hopefully you don’t mind and maybe you’ll even enjoy it.

As the title suggests, I lost my virginity yesterday afternoon to an older woman – I think she said she was 43. I’m a 22 year old guy from NJ, though that probably doesn’t matter. I have social anxiety and I’m generally pretty awkward around people so this really caught me as a surprise and I still have to remind myself it actually happened.

Anyway, onto the story..

There’s a small pizza shop about 20 minutes away from my house that my family orders from when we wanted to pickup a quick pizza. Previously, the cashiers at the pizza shop are college students that are home for the summer looking for a summer job. Since school has started back up (mid-August?), the cashier (Christine) has been the same woman each time my family has gone there. We went there a couple of times, enough for Christine to recognize us, our names and our order. Read more »

The strip club got her all excited.

I really enjoy reading this sub and figured I keep sharing a few of my stories.

I was talking to an 18 year old Dominican chick, short cute, she was not fat but she wasn’t skinny, she had huge DD boobs. One night I was out drinking and having a good time with a good friend of mine when she texts me to see what I was up that Friday night. My buddy told me to invite her and let’s all hang out, she quickly took an Uber and met us at the bar.

After hanging out at the bar for a while we get the crazy idea of going to a strip club ! Me and my buddy stop and get some cash out and she’s never been to one and we made it a great experience for her, she was pretty worked up and I couldn’t wait to get her home. After the club she drives me home, I was pretty drunk and tired from work. Read more »

It doesn’t get better than fucking older women.

Excuse the details, but I feel it all works together well. I’ve always wanted to tell this story. It’s long!

At the start of this year I ended up staring at the ceiling of a hospital with a health complication, it kept me there for the better part of the week. I had recently gone through a break-up with a long-term girlfriend and because I moved cities with this girlfriend I never put much effort into friendship / social circles. I didn’t feel like I needed to when with her.
We would typically hang out with one another visiting restaurants and cafes until one day she unexpectedly dumped me.
It was a real “oh shit” moment in my life, living in a city of 4 million people not knowing a single soul makes you panic just a little. Read more »

He showed me his true colours last night, and they’re incredible (F21/M)

Some of you might have read my last tale about getting four dicks in one night. The response was pretty exciting, and I definitely loved hearing how much you guys all loved it… So I’ve thrown off all the shame I was feeling before – I guess there’s really no better place for a slut than on r/gonewildstories!

I was out in this tiny late night bar last night. It was full of great people, and I ended up losing track of the guy friend I was with on the dance floor. As I stepped outside for a breath of fresh air, two arms enveloped me from behind. I turned with a smile expecting to see my friend Johnny, but instead it’s a guy that I slept with once or twice in the past.
We have a pleasant chat, but honestly, I’m more interested in scouring the patrons outside for my buddy.

That is, until he bends in close and says, “so, hey… Are you still single? Is this one of those nights where you… Y’know…”

I feel a little tingle of excitement run up my back. I hadn’t even been thinking about jumping back into bed with Richard, but now I was. Read more »

My first oral report

I’ve just started seeing this guy and I don’t know how else to say this, but I am absolutely in love with his cock. I want to spend all day on my knees worshipping him with my hands and mouth, making him cum and swallowing every last drop. It’s nice and thick and the perfect size, and so so smooth when he’s nice had hard.

I’ve only been with two guys before, my high school boyfriend for two years and then my boyfriend my freshman year but we broke up at the end of my freshman year and I just haven’t been with anyone since. I just started my junior year so I’ve been very lonely for a very long time. After the breakup I kind of stopped taking care of myself and gained a bit of weight but this summer I decided to put an end to that and really dedicated myself to the gym and so by mid August, my body was super tight and probably better than when I was in high school. Read more »

Sex with the ex

Bell and I were going through a bit of a messy break up which lasted a summer. We were both 18 and for all intents and purposes “first loves” She was a small hippy chick with big tits and a nice hairy bush – she was not conventionally attractive but was a demon in bed. We were going through a long break up where we were experimenting with other people and were both racked with jealousy and resentment about the relationship. She is the only girl I know that was able to come just from a few moments of a cock being inside her – I thought all girls were like this so you can imagine how annoying it was to find this was not in fact the case. However crazy in the bed also meant crazy in the head, she was manipulative and jealous towards the end with some violence thrown in! Read more »

Younger man, spontaneous sex (f/m)

I was on the prowl from the moment I got there. Exchanging looks with a few different potential suitors. I felt myself radiate my sexual appetite.

He was standing there, tall and baby faced. Not my usual type, with being younger however he was easily entertained. I asked him if he wanted to go on adventure. He was quite enticed by the idea.

I had him follow me away from the crowd down a hill into a barn. It was dark and quiet. I was suspecting I’d have to take charge but to my surprise his hands were all over me. Kissing me really hard and giggling along with me due to shared pleasure. I placed my hands to check his size and his largeness made me want him immediately.

I pulled him into me as I gently laid back onto the dirt floor. I took my pants off of one leg and heard him unzipping his own. He came back near me putting his fingers inside me, moaning at my tight wet pussy. Repeatedly hitting my g-spot causing my back to arch forward and my moans becoming almost whimpers. Begging for him to get inside of me. Read more »

2nd hookup turns into (m)y (f)irst time doing anal

I had seen this guy once before but we hadn’t met up in over a month. This is how our text conversation went.

Me “wanna fuck?” Him “when?” Me “now”

He says he needs an hour to get home from school but he’ll meet me then. Hearing that was exactly what I wanted. I went to the mall to kill some time and then texted him that I was on my way there. He says yeah come now. I drive to his place and park and he then tells me “PS I’m not perfectly groomed right now.” Like that matters at this point, I’m horny and really want to fuck him.

Some description of this guy, 26 years old, has scruffy facial hair, a very hairy chest which I love, he’s fit, cut, and the thickest person I have been with so far (my sample size is only 4 though lol). He is the hottest guy I have slept with and the one I have had the best sex with so far.

Probably some of you have read my stories before, but for those of you who haven’t. Read more »

Fucked my girlfriend’s friend after threesome (mff)

So it was my girlfriend’s birthday a few weeks ago, and big surprise, she got pretty hammered. She’s about 5’8″, D cups, blonde and very pale. I’m 6’2″, also blonde, with a 7-8 inch cock that is a little bit less thick than a toilet paper roll.

We went out for dinner on Saturday, and her friend came along with us. She’s about the same size as my girlfriend, with slightly smaller breasts and black curly hair with an adorable doe face. She’s a classic slut, got pregnant in high school by her older drug dealer and now she’s a single mom. We are all in our early twenties.

Over the course of the night my girlfriend got progressively more smashed, and I kept seeing her whisper to her friend and then they would giggle and look at me. I’d talked about bringing in a third with my girlfriend but we hadn’t discussed it in a while. At one point we were at a bar after dinner and my girlfriend was showing her friend something on her phone… it was a picture of her sucking my cock and her friend looked really turned on and she started giving me the eyes. My girlfriend came up to me when her friend went to the bathroom and asked me if I wanted to fuck them tonight, of course I agreed. Read more »

Drinking with the daughter of my dad’s neighbor [Almost MFFF]

This is going back a few years. I was 26 at the time, 33 now (pics of me are in my Submitted). I’m probably going to skip over a lot of details here, so if you want more information feel free to ask. And of course this is not verbatim because it was a long time ago and my memory is shit.

I was house sitting for my parents when they were away for the summer. I would stop by on the weekends to water the plants, pick up the mail, mow the lawn, etc. I went over on a Friday afternoon and I was up on the patio that overlooks the neighbors yard, watering the plants, and I noticed the neighbors daughter and some of her friends on the trampoline next door. They were bouncing around and laughing. I was trying not to look but they were really cute. Especially the neighbors daughter. They were clearly drunk and I knew they were crazy because these are the same girls that, the summer before, flashed me from their balcony and then ran back inside giggling while I was mowing the lawn. It wasn’t long before they called out at me. *I knew this was coming* I thought to myself as I turned around and leaned over the railing. Read more »