gonewildstories Archives — Page 503 of 5640 — NSFW story

My Year as a Sugar Baby Pt. 1: The Massage [MF]

I’ve always been turned on by age play. Whether a man is much older than me, or much younger (legal of course), the sex based on their respective life experience adds an extra layer of taboo that drives me wild.

In my 20s, I worked as a waitress or bartender. There was no shortage of older men that’d shoot their shot at a young, thick, big titted latina like me when I served them drinks. I knew how to work the bar and flirt to maximize my tips, but I’d never gone home with anyone or dated a customer.

That was until I met Damon. A software salesman in his mid-50s, I noted that Damon was a couple years older than my Dad. He had beautiful green eyes and thick, full lips surrounded by a well kempt silverfox beard. His head was shaved and he had a natural tan from his long jogs outdoors. His slim runners build looked trim in his suit, and his deep voice would make my knees weak when he’d address me. Read more »

helped my autistic friend lose his virginity [FM]

i’ve known this guy (M) from quite some time now and while he may seem weird to others he’s actually really sweet but he just needs some time to get used to new people. for the most while, i thought he was asexual because he said he doesn’t want to date …etc even tho i’ve tried to push him to do it before. Back in april, one day we were at lunch break and he told me he wants to start dating so i said i’ll help him. That same day, at night, he came to my room to ask questions, it was like a Q&A lol about girls in general. It then got a little sexual and i gave him many sexual tips including foreplay, eating a girl out….etc

i helped him with making a tinder account and after a couple of days he got a match! She was very beautiful and because M was kinda nervous to meet her, i was there when they first met so he’d be more comfy. a couple of dates later, they came from a date to our dorm and ran to M’s room, i don’t think they saw me sitting in the couch lol but i knew what they were going to do. next morning M came up to me and hugged me saying ”Thank you”. i think that was the first time he ever showed emotions lol but it was really nice :)

[F]23 I sucked off my sex-starved friend (26M) and let him fuck me hard

Last week I posted that I was going to let my friend (26M) fuck me after he hasn’t had sex in a year. He’s a doctor and spends his day saving lives so I decided to give him a night of pleasure, with the permission of my long-distance boyfriend.

On Saturday night I got ready while I was skyping my boyfriend. I wore a tiny red dress and black court high heels. I did my make up, including red lipstick and wore the jewellery my boyfriend had bought me over the years (gold watch, bracelet, necklace and ring). I had already got my nails earlier – colored red at the request of my friend.

I let my boyfriend jerk off looking at me getting ready for another man. He was bummed another guy was going to enjoy me that night, but I told him when we next met I would give the best sex of his life. I told him I would call him tomorrow but between now and then my phone would be off and I would be 100% focused on my friend. Read more »

Adventures in Ass Worship [MF]: Part 1

Back in the Summer of 2017, my then-girlfriend (who I will call “L”) and I took a road trip from NYC to Tennessee to watch a total solar eclipse of the sun. We left in the afternoon and planned to stop somewhere in Virginia to get a hotel, and finish the last leg of the trip in the morning. We spotted some signs for hotels and pulled off the highway onto a State Route. Unbeknownst to us, our trip coincided with both the Little League World Series, and a NASCAR race, so there was no occupancy in any of the hotels. We found a small roadside motel in the middle of nowhere, but the door to the office was locked and had a phone number to call. It was shady as fuck but since it was nearly 1AM, this was our last chance. There was a 7-Eleven across the road, so I went in and asked what the deal with the motel was. They said that if we stayed there, we’d get bed bugs. With that, our fate was sealed, and we decided to drive through the night… Read more »

I still squirm when I hear the words pencil skirt [MMF]

She truly was the bossy bitch from hell in her grey pinstriped pencil skirt and those black shiny heels that you heard clicking in the corridor.

‘Imagine that tight skirt lifted up, turning her skinny ass red and all’ had said Tom smirking that fateful day. He was such a perv. Always trying to distract me from my spreadsheets. It was amazing I ever met a deadline when he was on with me.

‘Oh I’d give her a good taste of her own medicine’ I replied giggling nervously. ‘Go over the knee just perfectly.’ The truth, of course was I wouldn’t. I couldn’t. I didn’t have it in me. I was just another boy caught up in office chatter, wanting to impress Tom. To make him think I was one of the lads too.

It was that fatal sentence though. When I said out-loud ‘the stuck up bitch, how has she been promoted over me she’s only 27?’

Maybe I would have got away with that if I hadn’t added.

‘Bet she’s got filthy slutty knickers the stuck up cow’ I said squirming a little as I imagined what our new boss was wearing under that tight fitting pencil skirt. Read more »

[MF] I Met a Hotwife from Reddit Pt. 2

After Jess and I met for the first time, I couldn’t wait to see her again. It would be a couple of weeks though with both of our obligations, but finally we found a day where we could get together for a couple of hours. The anticipation leading up to the second meeting was amazing though. We’d flirt throughout the days and she sent me some videos and pics to work me up.

Anyway, the day finally comes. I wake up, eat a little lunch and make sure my place is clean. I also set out some massage oil and lube and eagerly await for Jess to arrive. There’s a knock on my door, my heart is pounding, my cock is getting hard, and then I open it and there she is again.

Jess is extremely sexy and after we hug and get my dog to settle down…(quick sidebar guys…get a dog. easily the best wingmen you’ll ever have), we head back to the bedroom. Read more »

[MF] Wife ran to work with my cum still in her mouth

My wife wore a short tight black skirt that hugged her shapely hips. Beneath it she had sheer black stockings, the tops of which peeked out if even a millimeter of her skirt rode up as she walked. Her top half was dressed a little more conservatively with a crisp white shirt beneath a grey jacket that buttoned just below her breasts. Her outfit was completed with a pair of black high-heels that made a tippy-tap sounds as she walked.

She noticed the way I was looking at her as she collected her things on her way out the door to work. Smiling at me, she told me she’d seen that look before and thought she might be able to help me out. Read more »

The time I stuck my dick in crazy Part 4 [MF] red flags, red flags everywhere

I have a little time this morning, so I figured I would write up about the time Melissa gave me a HJ in the sauna at a crowded pool….

As I said before, I was in a dark place at this point in my life, drinking daily, dabbling (okay more than dabbling) in drugs far harsher than the weed I was also smoking. Yet somehow, continued to go to the gym on a semi regular basis. Sure I would make myself presentable and be the best guy I could around my kids when I had them. But all in all, I was a fuck show….. Melissa was keeping me on just enough of the edge that I wasn’t fucking anything that moved (that came out later in the relationship).

I was still on nights, so I would be sleeping by 9am, and up at 2-3, crack a beer, make some eggs, protein shake, and then head out to the gym, which was located in the community center, so there was a pool and sauna attached to it. Read more »

How I (22m) gave my fwb (21f) her best orgasm in a while [MF]

I’ve been in an fwb type thing with this girl for about 2-3 months now. We don’t see each other too often (maybe every 2-3 weeks), but when we do we cant keep our hands off each other. We usually put on a show when she comes over. Every time, not 10 minutes in, we start kissing each other, she puts her hand on my chest, my fingers start lightly brushing her nipples, then my hands are over her ass.

Nia is one of the most beautiful women i’ve ever been around. It feels like a privilege to even be able to be in the same room with her, let alone get to fuck her. It’s not just her physical looks, although she certainly would make your head turn if you saw her passing by. She has tender brown eyes, nice soft tits, and a beautiful ass. Shes athletic and physically fit, I love feeling her muscles around her body. The way she really pulls you in though, is how she carries herself. Her aura is so unique. Every atom in her body radiates Black Queen energy. Beyond her natural beauty, she has a mastery of the tools available to her. She’s an artist, so her makeup is always so creative and interesting. Her clothes and outfits are always on point. Looking at her feels like looking at art. Read more »