Category: gonewildstories

[F] Boyfriend encouraged me to tease a guy at work

Recently my boyfriend and I opened a bit more sexually. It’s not a consistent thing, but sometimes he will want to hear about my past experiences, or about recent times when a guy was checking me out. He will love to hear every detail.

I recently told him about a guy who services some equipment around our office. He’s usually at our building once or twice a month, and I don’t always see him. He’s a younger guy and I enjoy our brief conversations when I do see him. I told my boyfriend about the previous two brief encounters I had with him. They weren’t anything extraordinary. Just how I noticed him checking out my cleavage and ass.

My boyfriend really loved hearing about this. And to be honest. I may have exaggerated a little bit to him because I loved how into he was. As we talked my boyfriend kept saying how I should tease him intentionally the next time he’s at work. I was a little skeptical because we were talking in the moment. It could be another month before I saw him, and my boyfriend may feel differently. Read more »

Caught Watching Porn Pt. VIII [MF] [Masturbation] [Anal]

[*Episodes I to V are over there*](https://www.reddit.com/r/dirty_boy69/comments/vifcax/caught_watching_porn/?utm_source=share&utm_medium=web2x&context=3)*,* [*Episodes VI and VII are over there*](https://www.reddit.com/r/dirty_boy69/comments/wvb0f6/caught_watching_porn_pt_ii/?utm_source=share&utm_medium=web2x&context=3)*. I advice you to read them first. Enjoy your read.*

Nothing out of the ordinary happened at our place for some time. It all changed on the day, the delivery arrived. The day our new sex toys showed up. They showed up on the Wednesday after I took pictures of my roommate fucking her friend. The delivery was already there, when I came back home from work.

After opening the door, after I came home, it didn’t took long, until my roommate was jumping around me. Total hyped. Telling me that our delivery had arrived. While doing so, she walked me into the living room. There, on the table, all the stuff we ordered was placed. Everything we ordered had arrived.

I thanked her for receiving the order, then I took my stuff and dumped it into my room. After stowing my new toys away – well, the landed on my desk – I went back into the kitchen, to prepare myself something to eat. I was in the kitchen for a minute or two, when my roommate began to jump around me again: “Do you want to play together tonight? Should we try out our new toys? Together?” Read more »

The BBW redhead in a black velvet dress [MF]

It was a snowy Friday night in January. My friends and I had plans to go out for drinks at a really nice local hotel. It was a popular spot and the place was lively as we entered and approached the bar to order drinks. We found a little spot to stand around and socialize while we were of course examining the potential prospects in the room.

While running my eyes across the room I noticed a redhead woman. I did a double-take after noticing the black dress that was hugging her figure. I couldn’t take my eyes away from how her black dress was hugging against her round ass. She was surrounded by a couple other women and a group of 5 or so mostly older men who all looked very professional.

Our night went on as my friends and I put back drinks and started socializing more with strangers. The redheaded woman was still in her group so I didn’t bother making my way over to her, though I could not stop glancing in her direction every few minutes. Read more »

[FM] I Was a Serial Cheater #3: He Was So Big

In my early and mid-20s I went through a size queen phase. When we went long distance, my BF (now husband) gave me a couple porn DVDs for when we wanted to have phone sex or I was lonely and wanted to pleasure myself.

One was specifically of Latinas getting fucked and one was of BBCs fucking white girls. The latter had me intrigued, especially after my experience with El from my previous post. I started watching more interracial porn and loved the contrast of the different skin tones and of course, was curious about the size and what a gigantic cock would feel like.

I tried a couple times to fuck myself with a thick cucumber but found it uncomfortable, but still wanted to know what a big cock felt like.

I love to dance and during an evening out with the girls at the club I was downing Long Island Iced Teas and definitely had 1 or 3 too many. I usually don’t dance with men at the club but was really enjoying the different strangers pulling up behind me to feel my ass grind on their dicks. It had been 6 months since I got any dick at this point. Read more »

[FM] My last night as a sugar baby, ever

This is exhilarating! I want to keep this up a little longer. Like I said on my last post, I worked as an escort and a sugar baby all through my late teens and twenties. A few years ago I got out of the biz, if you want to call it that, and now I make a living mostly from my investments. This is the story of my last night as a sugar baby.

Some people asked me to describe myself last time, so I will. I’m thirty six years old now and for a long time I struggled with not being so young anymore. But even though I weigh more than I did when I was a twentysomething, I still work hard to keep in shape. I’m curvier now than I was then, but thanks to the gym I make it work for me. My hair is long and chestnut brown, the same color as my eyes. My eyelashes are my best feature while I have clothes on. When I was a teenager I struggled to stay as skinny and small as the other girls, so I appreciated when bigger butts and tits came into vogue. After so many years dressing to impress I usually wear athleisure clothes unless I’m going out with friends or on dates. Read more »

I fucked my airbnb host [MF]

This happened two years ago when I went on my vacation.

It was my last full day at the airbnb and the sun was out so i decided to sun bathe naked since it was a nice day and wanted to even out my tan.

I ofcourse forget to put the do not disturb sign on my door and she came in with towels and other stuff into my room.

I saw her staring at me through the sliding glass door and I immediately get turned on. She doesn’t realize yet that I know she’s staring so I start to play with my cock.

Once I’m hard I look directly at her and smile, she starts to blush and smile. She was a bit flustered and embarrassed so I get a towel and wrap myself with it.

I apologize to her and tell her I forgot to put the sign on the door, she giggles and says it’s ok no harm done. Read more »

[F]22 Did I help this man cheat on his wife and broken a marriage?

First off, older men…can’t get enough of them. I am so surprised to find that many of them on Tinder and Bumble. You’d think you’d have settled with a wife by then. Apparently not.

I met a gentlemen who 44 years old on Bumble. We flirted and sexted for a while and when things were starting to heat we decided to book a hotel room and do the deed. He booked a really expensive hotel for the night, took me out to dinner in a very fancy restaurant and it made me feel really good. Things were starting to heat up a lot in the car when we were making out. He slipped his fingers under my dress and I was soaking. I sucked his dick in the sloppiest way a thirsty whore could.

When we reached the hotel room, we wasted no time. We undressed each other and were ravaging each inch of naked skin we could find. We were also very very very drunk.His dick transported me into another world. A world filled with so many orgasms I lost count. Older men are too experienced. They know how to please a woman. I squirted so many times. Like the good little whore I am, I let him fill me. He took it so deep inside I think I felt it in my gut. The fluid started oozing out of my vagina. It was easily the best sex I have had. Read more »

[MF] My Wife’s BBC Hookup: Update #1

It’s been an interesting couple days with my wife since she sent me the video from the previous post.

She’s been acting shy and a little stand-offish. Feeling a a bit guilty and she may have crossed a line.

We sat and had a discussion and I reassured her she can talk to me about anything; that the past is the past and I find her sexual history nothing but arousing.

She asked if I’d be willing to go tit for tat and let her ask questions too, another time. I said “of course.”

I poured her a cocktail and we sat across from each other at our kitchen table while we sipped and smoked a joint.

My Q’s and her A’s:

Q: Was that a new video or one you’d saved?
A: Saved

Q: Where did you save it?
A: Google drive

Q: Are there more videos
A: Yes

Q: Of just him or different guys
A: Different guys

Q: Why did you save them
A: Just fun memories and every once in a while she’ll touch herself to them. Read more »

One Last Hurrah [MF]

This story dates back to a few years ago. I 31M had been peaking in what many would call a hoe phase, being a fuck boy or whatever other term you would like to use. I had gotten out of a year plus long relationship that ended when we realized it just wasn’t a long term fit and I decided to explore the open market.

I did exactly what I’m assuming most men do (correct me if I’m wrong) and did two things right away:
1. reached out to a former ‘sure thing’
2. Fired up the dating apps

Although I had great success with number 2 this story is about item 1, Holly.

Holly and I had hooked up a bunch prior to my relationship and although she willingly and repeatedly reached out to me while she was coupled up I didn’t stray from my partner. Once my relationship ended, and she heard I was back on the market, she reached out the next day and two days later was back in my bed. Holly would best be described as the poster girl for r/petitegonewild with a slim frame, toned stomach and proportional breasts and bottom. She had long, dark brown hair and a mischievous smile. The sex, as always, was great. We picked up where we left off over a year before with her squirting time and time again into my hand and screaming out for daddy to fill her with cum and get her pregnant. This girl really did something to me. Read more »

I slept with my best friend’s lesbian step sister at his wedding [MF]

I was 27 when this happened (so, 10 years ago). I flew out to San Diego for my high school best friend’s wedding. We’re from NY, but he went to grad school out there, met his now wife, and stayed. I’m pretty sure I was the only one from our high school friend group who went, there were a few other college/grad school friends, but it was mostly family other than that. Oh, also my high school principal, who happened to also be best friends with my friend’s father, but that’s not important, just funny.

The only other person from my high school who was there was Lizzie (name changed). She was 2 years younger than us in school, and she happened to ride the same bus as me. I think my friend introduced us when she was starting her freshman year because their parents were dating, and eventually got married. Lizzie and I would talk a lot on the bus, especially since we were both very active with after school activities (she was a cheerleader… yes, really, I’m not making that up haha), so we’d both end up on the late bus together a lot. We never really hung out outside of school, other than the few times I went to my friend’s dad’s house to hang out. Even then, we’d usually just say hi, and then we’d kind of go do our own things. But on the bus rides, we were actually pretty close and would talk about a lot of different things. Read more »