Category: gonewildstories

Hooking up with a dad in the neighborhood [MF]

So a lot of you have been asking about the dad of my brothers best friend so I figured I’d spill the beans on that one. Up until now, my sugar daddy is the only guy who knows about of this but I’m feeling extra adventurous today so here we are lol.

The man in question lives on the same street I grew up on, is married with 2 bio kids who are older and 2 step kids who are younger (my brothers best friend is the oldest of the step kids). He’s a good bit older than his wife and was in his early 50’s when all of this started. He’s built REALLY well and has a silver fox thing going for him. If you can’t tell from my previous stories, I have a weakness for older guys and Daddy types and he oozed all of that in spades. He was always around with his step son being so close with my brother and our neighborhood always having lots of cook outs and block parties and stuff through the year. Read more »

Meeting [M]y first G[F] for the first time in years, part III

Firstly, thank you all for the feedback, I read all of it and considered it. Some of it was useful and constructive, some was critical but non judgemental, and some was harsh but fair.

So it’s been a while since posts and I’ve gone to write updates several times, but a lot has been happened since so I thought I’d save it for one post.

I’ll start by saying that, though I tried at first to cut my ex, things have since changed and we’re basically fucking whenever my wife is at work and sexting all other times. Read on if you want to know about how we got there….

After retrieving my wife’s underwear and putting them in the wash with some of my clothes to prevent her from noticing, I got a message from Kat.

K: So, how do I become worthy

T: You can’t, sorry. Not gonna happen again

K: I think I can, didn’t you see how willing I can be…

At this point, I decided to take a different tack to this approach, try to take the power back, even if it meant causing a little hurt. I also decided it was best to switch to a more discrete messaging service which unsurprisingly, she had. Read more »

I naively agreed to a threesome without realizing [FM]

This happened shortly after I started college and I began experimenting with sex and was figuring out having FWBs. When I started I was very worried that the people I slept with would get attached and think we were dating or something (myself included at least a little bit). So during this time period I tried to be overly clear that it was just sex, but I also still tended to hang out causally with the people after meetups: playing video games, getting food, watching a movie, etc.

This is what was happening after the first time I’d hooked up with anyone from my high school. I go to a instate college so there are a lot of people from my high school class that attend. I’d been nervous setting it up with him as I had some weird stuff in highschool where people had basically turned to have a competition to sleep with me and it did weird things to my reputation, but he was a guy I’d always been into so when he showed interest at a party we were both at we started texting again. So I set up a time to meet. We’ll call him John. Read more »

[FM] Got a text from my gf with an attachment

(24M/24F) Gf was on a girls trip a few weeks ago and I got a text from her one night saying they were playing truth or dare and she had been dared to do something and send a pic.

As I’m reading with all the excitement in the world, I get the attachment: it was her, in front of her friends, with her tits pulled out of her dress for everyone to see. The look on her face of the embarrassment and the look of her friends faces turned me on so much. She has amazing tits.

It absolutely sent me, we both have a huge voyeur side and was amazing to get the pic.

An Old Flame scratches an Old Itch

This all happened last month. If you don’t care about the background, head down to the XXX line for when the sex actually starts.

A little background on the key players (with names and jobs changed a little to keep things anonymous).

I’m Dan; my best quality is broad shoulders. I’m in my late thirties, I was a slow starter in dating, and hugely regret not having more fun in my twenties. I have an average length, girthy cock, which I shave when I remember (and it was shaved for this).

Maggie is my ex; she’s a private healthcare worker, and we dated about 10 years or so. She’s 20 years older than me, didn’t look it at the time, and somehow hasn’t aged since (she looks younger than me). She’s a fairly short redhead, has absolutely *huge* boobs (38DD), and looks like a cross between Darla Crane and Demi Dean.

NSFW reference pics, if you‘re interested:

[https://www.google.com/imgres?imgurl=http%3A%2F%2Fi.imgur.com%2Fh82iCFD.jpg&imgrefurl=https%3A%2F%2Fwww.reddit.com%2Fr%2FAgedBeauty%2Fcomments%2Fahn3j6%2Fdarla_crane%2F&tbnid=958Vr3wZG0uEYM&vet=12ahUKEwjCjdX3-IvzAhVHaBoKHSfKBDgQMygLegUIARCVAQ..i&docid=ZkFTykrSuFTGDM&w=800&h=1200&q=darla%20crane%20imgur&ved=2ahUKEwjCjdX3-IvzAhVHaBoKHSfKBDgQMygLegUIARCVAQ](https://www.google.com/imgres?imgurl=http%3A%2F%2Fi.imgur.com%2Fh82iCFD.jpg&imgrefurl=https%3A%2F%2Fwww.reddit.com%2Fr%2FAgedBeauty%2Fcomments%2Fahn3j6%2Fdarla_crane%2F&tbnid=958Vr3wZG0uEYM&vet=12ahUKEwjCjdX3-IvzAhVHaBoKHSfKBDgQMygLegUIARCVAQ..i&docid=ZkFTykrSuFTGDM&w=800&h=1200&q=darla%20crane%20imgur&ved=2ahUKEwjCjdX3-IvzAhVHaBoKHSfKBDgQMygLegUIARCVAQ)

[https://www.google.com/imgres?imgurl=https%3A%2F%2Fpbs.twimg.com%2Fmedia%2FCvJvCG1WYAA1VZx.jpg&imgrefurl=https%3A%2F%2Ftwitter.com%2Fdemideanmilf&tbnid=_70qgxVjOKH5_M&vet=12ahUKEwj0-8q3-YvzAhUIBRoKHXaKB2sQMygJegUIARCNAQ..i&docid=sH6_Jzq4uSCNwM&w=400&h=522&q=demi%20dean%20xxx&ved=2ahUKEwj0-8q3-YvzAhUIBRoKHXaKB2sQMygJegUIARCNAQ](https://www.google.com/imgres?imgurl=https%3A%2F%2Fpbs.twimg.com%2Fmedia%2FCvJvCG1WYAA1VZx.jpg&imgrefurl=https%3A%2F%2Ftwitter.com%2Fdemideanmilf&tbnid=_70qgxVjOKH5_M&vet=12ahUKEwj0-8q3-YvzAhUIBRoKHXaKB2sQMygJegUIARCNAQ..i&docid=sH6_Jzq4uSCNwM&w=400&h=522&q=demi%20dean%20xxx&ved=2ahUKEwj0-8q3-YvzAhUIBRoKHXaKB2sQMygJegUIARCNAQ) Read more »

I [f] had a threesome with two [m]ale co-workers

I work at a techie startup that is predominantly male. New policy has me going into the office twice a week.

More recently, the company had its first happy hour in a while. We went to a local bar and it was a professional enough setting until everyone left except me and 2 co-workers – let’s call them Marc and Jon. We were all pretty drunk and decided to go dancing at a nearby club (we’ve all been vaccinated and wore our masks).

Marc and Jon don’t work directly on my team but I’ve worked with them a bit and have always been super friendly. I’m a petite girl with perky breasts that are a perfect handful and a little round ass. This night I was wearing a form fitting cropped t-shirt that hugged my curves and a pair of soft wide leg pants – it was a simple work appropriate yet comfortable outfit that I felt confident in. Read more »

Breaking our only Student House Rule [MF] (p.1)

I think it’s quite fair to say that even after all the meetings we had had and all decisions we had taken, we both, and I think by extinction the whole house, knew that this was inevitable. There simply was too much alcohol, carelessness and attraction to keep us from gravitating towards each other. Now, a few years later, I’m able to look back through the fog of time, unearth some of these scenes and examine them within the context in which they are supposed to be looked at (and not only through that sleep deprived head of those days, which I carried upon my neck as a crown). But I’ll start at the beginning, that is; a suitable beginning. My birth, nor my first day to school, nor my first orgasm are all of little importance to this story. I’ll start after dinner. With the sun sinking through the trees and the wind whispering with fallen leaves across the asphalt. Autumn had arrived, 2019. Read more »

Experimenting and swapping [GROUP] [MMFF]

I’m not going to say what it was the Mona suggested, you can just read about it as it happened here, though I will give fair warning for anyone not into it, there’s a bit of same sex action, including a tiny bit of same sex male on male, though not much.

Skip to the ————— if you just want to read the sex section, the rest is a long lead up.

It was two weeks later, on a Friday, we needed John to come back home, and then they needed to find a weekend for their kid to stay at one of their parents. I was driving home from work, running late, when Jenna called me and told me to go straight there.

“I don’t have a change of clothes though,” I said.

“Don’t worry, I don’t think you’ll be needing clothes tonight.”

I got there about an hour or so later. I had been drenched in sweat for the majority of the day. They had been hanging out in their kitchen area, chatting. I saw the ashtray already had a few butts in it, and a half empty bottle of wine next to an empty one. Read more »

[F]ucking [M]y Boss in His Girlfriend’s Apartment: Part 2 – The Next Morning

PART 1 FOR CONTEXT: https://www.reddit.com/r/gonewildstories/comments/pr5z5o/fucking_my_boss_in_his_girlfriends_apartment/?utm_medium=android_app&utm_source=share

The next morning, I wake up to an empty bed. I’m hungover & feeling guilty that I’m laying in another woman’s bed, fucking her boyfriend, who I work for. I remember just staring at ceiling thinking “wow I fucked up..” After a couple minutes, I’m like where tf is B? I hop out of bed, put on last nights clothes and plan on quietly sneaking out. Hoping to avoid any awkwardness.

I walk out of the bedroom and see him drinking coffee at the kitchen counter with an “oh I fucked up” expression on his face. He snaps out of it & says good morning, and offers me a cup of coffee. I accept and we start talking.. He quickly apologizes for putting me in a weird situation, and explains that last night he was just drunk and lonely and that none of this should ever happen again. I agreed with him, we both just had a lapse in judgment and it wouldn’t happen again. Read more »

[MMF] My wife [27F] and I [28M] had a MMF threesome with a fellow Redditor [27M] the other night

Backstory: My wife (mandy) had been chatting with a redditor I had found to help me explore being bisesexual lately. After talking with him on kik and meeting up at a restaurant my wife and I decided we wanted to do a little more next time we met up with him. The following time we met up I ended up being really tired and retired early. I found out the next morning that she had blown our friend after I went to sleep and told her that I was pretty jealous. So this story takes place the next time we met up with him. Names are changed for privacy’s sake:

Me: Me 28m 6’1 ~215lbs dark long hair and eyes 6.5″ cut

Mandy: my wife 5’4 curvy huge ass and tits

Jack: about 6 feet and a nice 7 inch cut Read more »