A Weekend with [M]y [f]antastic Older Woman

[Helen](https://www.reddit.com/r/gonewildstories/comments/6r8o55/alls_well_that_ends_well_mf_mff_update/) was pleased with the response [the last story](https://www.reddit.com/r/gonewildstories/comments/8on4m4/unplanned_unexpected_my_first_older_woman/?utm_content=title&utm_medium=user&utm_source=reddit&utm_name=frontpage) got, but disappointed with the story.
“Show, don’t tell!” she said “You left out most of an entire weekend!”. I was going to explain the importance of leaving the audience wanting more, but something happened that I want to write about later.

After that – I know…but I tease because I care – Helen sat thinking.
“If you’re not going to give people a blow by blow account you should tell them what happened the weekend after.”
“It was fucking,” I said. “More of the same, I’m afraid.”
“Gonewild Stories is full of that already and people don’t seem to be bored,” said Helen, “but is there anything you’d prefer to write about? And don’t put this bit in. It’s too meta.”

[FM]a sluts way home

A few years ago, I spent a weekend in the big city and went out with some friends. I had withdrawn a nice handful of cash for the occasion and thought it’d last me throughout the weekend but it didn’t go as planned. I was totally hammered and somehow I had moved from the inner city to the outer areas. I had my phone on me but my purse? It was long gone. I sat down on a bench and started to look for a cab. Just as I dialed up, my phone died. Great I thought, just my luck. I stayed on the bench for a good few minutes. It was facing a busy street with cars and people coming and going. I considered my options, taking into account that I was very drunk and very lost. I knew that some of my friends lived in the city but I didn’t know their exact addresses and I had wandered too far already. After what seemed 5-10 minutes, a car pulled up on the sidewalk.
“Parking not allowed” I thought, shaking my head and not really realizing it was me the driver was pulling up for. It was a younger man, perhaps a few years older than me. I was 23 and he looked 27-28? He called me over and I reluctantly got up.
“I must have driven by you three times perhaps?” he said. He was pretty good looking.
“Why?” I asked and leaned against the car to not lose balance. I noticed that the top of the car had a taxi sign, it wasn’t turned on though.
“I saw you coming down the street, you looked like you needed help” he said. I thought it was kind of him and told him I had lost my wallet and my phone had died. I was lost and didn’t know where to go.
“Hop on in” he said and assured me he’d get me back to the inner city. I told him I didn’t live in the city but 2 hours away to which he replied casually
“I’ll get you there” and I said thanks.
2 hours in a strangers car would scare most women, but I was drunk and I just wanted to get home.
**I however don’t recommend anyone to do what I did, because it’s stupid and risky and I was just lucky.**

[MF] The russian MILF’s daughter

I’ve told the story of how I met a beautiful mother-daughter pair of russians, and how I ended up [having sex with the mother](https://www.reddit.com/r/gonewildstories/comments/8r9nbo/mfrussian_milf_on_holidays/). Then, I told the story of [the morning after](https://www.reddit.com/r/gonewildstories/comments/8rq56j/mf_russian_milf_on_holidays_the_next_morning/). Some people asked me if I got to be with the daughter. Well, I did, so here’s how it went…

It was my day off, so I spent the rest of it with Jana and Olga. We went outside, visiting a bit, and we ended up in a nice beach not too far from the hotel. We teased each other a lot all this time. The girls asked me to rub sun screen on them, which I happily did, taking my sweet time when covering their asses. At some point, I went for a swim, leaving them tanning. When I came back, they were talking together in russian and giggling, and Olga gave me a discret dirty wink. We eventually went back to the hotel, washed ourselves and met for dinner. We then went for the show of the night, and the girls decided to wait at the bar for my friend. I went around a bit, talking with people, and met them again just before the end of the show.

Too good but is true [fmf][long]

I came home after this whole thing you will read and typed it up. Waiting until I was horny enough to share. I guess that’s now. So this was a month ago

My husband planned a guys night out with his friends out of town an hour. They were going to get hotel rooms. So i planned a girls night out in town. We were going to stay downtown at one of our friends. She lives down there in her apartment she owns and she wanted to plan the night for us.

We headed to her place and dropped off our stuff. There was three of us for dinner. We went out to a nice restaurant and got tipsy. We walked back to her place and and started getting ready. Of course, another bottle of wine. While nothing happened between us girls we were walking around in our panties putting on makeup and doing our hair. My friend with the place (Rachel) has nice big boobs. She is single and her 34 C cup are perfect by my thoughts. My husband always sneaks looks of them. Mine are small. Enough to grab, but not handfuls like hers. I’d be jealous if I didn’t have a better butt. Hers is ok, and she works out, but it is small. Our other friend (Katie) is slim with not many curve but she is super fit. Hits the gym regularly. Her boobs are slightly smaller than mine, but she is nicely toned.

I’m bisexual and had sex with my best friend [ff]

So my best friend knows I’m bisexual. It’s not something we talk about a lot but we both know it’s true. Well we ended up having a three way with this one really hot guy one night. It was so hot. I ate her pussy out so much and fingered her while I was getting pounded from the back. I even rode his dick while she sat on his face. The night was a lot of fun. I ended up having sex with that guy again just me and him. Well today he hit me up for sex. But my best friend has been really horny lately. I knew he would hit her up next and I was with her so I texted him back that I had plans already. Then HE TEXTED HER AND SHE TOLD ME. I encouraged her to have sex with him because the thought of that is so hot. Both of us fucking the same big cock. The guy thought neither of knew what was going on. But I knew. She didn’t though. So anyways. She’s on her way to fuck him now but he’s texting me like he’s gonna have a lonely night. I don’t know why this entire situation makes me so horny. I hope we have another three way. The guy just asked me to fuck him tomorrow night. And I’m going too

First Threesome Success! [MFM]

After a wild ight of partying and downing tequila like there’s no tomorrow, things started to get a little frisky downstairs. First I (M) witnessed my girlfriend (F) drunkenly make out with her friends (FFF) and feel up on each other. My best friend (M) was with me during all of this and we both agreed that it was INSANELY hot. One thing led to another and the idea of an orgy came up (MMFFFF) but this got shut down due to puking ensuing after shot # whatever…
Fast forward to Father’s Day morning, we are all in bed talking of having an actual orgy party, so when that happens I’ll fill you all in. ;) I leave to drive my friend home and we smoke and talk about last night when the mention of my girlfriend and I’s fantasy for a three-way. At first I wasn’t sure if I wanted it to be my best friend to be the one fucking my girlfriend. A little while later, he was talking about his fetishes and noticed how similar they were to my girlfriends. After hearing this I was interested in recruiting him because I am non-monagamistic, and though it sounded hot thinking of them fulfilling their fantasies, but more her than him. With this information, I tell him that her and I would talk about it and let him know.
I get to her house and tell her about the idea. She was *very* intrigued, but was worried about him being my best friend and the sex getting in the way. Also that if I didn’t like it, it would ruin the relationship, but I have fantasized about (MFM) threesomes prior to this so I was down for it. After convincing her that I was okay with it, we agreed to do it but she was still a little shaky on the idea of it. To make sure she wouldn’t back out of it, I suggested that we do it that day in a few hours. She said okay. I call my friend and sure enough we agree that at 4:30 was the time the fun would start.
We rush to my home to get lube, handcuffs, and a blindfold. She wore a very sexy piece of lingerie and we head over to his house. After a few shots, I tell him to go wait in the other room while I got her ready. After blindfolding and handcuffing her, I go grab my friend and the fun begins…
I start by eating her pussy and ass while my friend gets warmed up. She moans as my tongue goes back and forth between both holes and I start to finger her slowly. Her cum is dripping from her pussy because she was so wet in anticipation. A short while later, I’m primed and ready and switch spots with my friend. I flip her to where she’s on her back and start to throat fuck her while she is getting eaten out and fingered by my friend. She’s moaning and choking as my cock fills her throat and drool is dripping from my cock as I pull it out to hear her moaning.
My friend loved fingering her and when I looked down he had four fingers inside of her and her pelvis was grinding and gyrating from the pleasure. This continues for about 10 minutes and then I’m ready to plunge my cock deep into her. We switch positions and I uncuff her and take her blindfold off and she gets on her stomach. She sees his cock and starts to suck him dry. I can feel her other lips wrap around my cock and shudder from the feeling. I fucked her vigerously and ended up pushing her head forward so she would gag on his dick and come down on my cock in an alternating system of pleasure. After this I get up because I’m ready to bust and shoot long strings across her back.

Pushing boundaries. [MF]

So, I’m not kinky, but I like trying new things and pushing personal boundaries. I recently started dating a kinky guy to help with this boundary pushing.

I arrived to his place and he stripped me down and blindfolded me. He put a collar around my neck and four small, cold, wet(?) ovals on my inner thighs. Soon I felt a few small electric shocks on my thighs. The ovals were some sort of conductor. Then he got out his hitachi vibrator. He massaged my breasts and nipples before moving down. He moved the vibrator near my clit without touching for the longest time. My lust built and built as he brought the vibrator closer and farther over and over.

“I ordered food,” he said “I’d like you to answer the door naked.”

“Fuck,” I breathed “no.”

He smiled. “But you’re my little slut today” he teased “you need to do what I say. If you don’t I might have to punish you.”

I gritted my teeth and raised and my squirmed my hips. He still had the vibrator on me. “Train me like a dog. You wouldn’t beet a dog. How would you teach a dog?”

Corrupted by an Older Man [FM]

Disclaimer: This is my true story about how I went wild online with one guy. I haven’t really gone wild IRL with my physical body. Not yet, at least. So sorry if this seems lame. It certainly doesn’t seem to be as wild as others’ stories here. Everyone in the story was +18 at the time. I am currently 23.

I was 18 and he was 49. Although I have mixed feelings about what I did, I have no regrets. I’m more happy than not that we did what we did. We met online in my first year of college. At the time we met, I hadn’t yet had sex. I grew up in a nice middle class neighborhood, private school, etc. I had kissed some boys but that was it. My environment before college was structured and full of rules and expectations, and I didn’t feel the need to rebel against them. I more or less had what I wanted. With the freedom of college and my very own laptop, I decided to do some exploring online.

[MT] Fucked by a trans woman in Italy

Two years ago I were out traveling in Europe by train. I went all over and when I came to Milano in Italy I decided I would try to find someone to have sex with. The reason for this was because I have not had sex or jerked off for 2 weeks, I was horny like hell. Anyway, I have never had sex with a man before but I fought I wanted to try it. So I made a grindr profile and started looking. I did not really find it that interesting but I saw a girl there on the start page. She was sort of beautiful, maybe not 100% passable as a woman but I found it really attractive! Sended her a message, she responded quickly. We talked some and what we wanted to do. So she told me to meet her up at her home.

She did not live in Milano so I took a train to where she was. When I got there she was wearing an attractive dress, she had quite a lot of makeup, pretty big boobs, long black hair and big lips, had not seen her cock yet. When I steeped through the door she greeted me with a wet kiss, her tongue was all over my mouth and from nowhere she grabbed my right butt cheek. I reached for her ass as a return and gently squeezed it. My cock were now as hard as it could be.

The Time I made her watch. [MF] [Cheat] [Cuckquean]

I was an asshole back in college, I still am but I was also one back then as well. So here is how I broke up with my then girlfriend Amanda. Amanda and I had been dating going on a year and a half before things started to go stale. School was getting pretty tough for me and since she was an hour away it made things just that much more lame.

Amanda lived with her best friend Denise. Denise was a short blonde who dyed her hair black with a cute bang cut. She was probably 100 lbs wet and had little to no curves to her. She did have a sexy face though, one that radiated desire when you looked in to her eyes. She was quite the opposite to Amanda who was average height with curves to die for. She had a perfect hour glass shape and a cute face. Side note: these girls liked to party. Both of them were definitely not the girls you brought home to meet the family but at the same time Amanda was sweet and we hit it off well.