Category: gonewildstories

[M]y [F]irst Time [Cheating] With Lily

If you want to skip to the action, go to the *****

My name’s David, and this story takes place nearly a decade ago when I was 21. For a brief period of time I was sleeping with my OG high school crush, Lily. Lily and I had always been close friends in high school, but owing to my own nerdy demeanor and bad timing with our other relationships we had never actually gotten together during our teens. Like a lot of guys, I didn’t find my confidence until University, when girls started noticing and hitting on me for the first time.

Lily was an absolutely bombshell. 5′ 9″ (somewhat shorter than my 5′ 11″) with alabaster skin in contrast to her crimson red hair and sharp green eyes. Her classic hourglass frame and plush D breasts made her the subject of many people’s attention – guys and girls alike. She was the most outgoing bisexual girl I ever had the pleasure of seeing romantically, and was simultaneously flirty but dismissive in a way that just made everyone around her crave more of her attention. Read more »

[MF] I slept with the hottest girl in the sorority part 2

I’m glad people seem to be liking these posts. Check my profile for previous parts. For people who are curious for a comparison of what Sarah looks like, look up “Rachel Riley” from the British show countdown. Idk how tall Rachel Riley is but Sarah was probably around 5’10 and she had a dancer’s ass so in my memory she’s got more…features.

Long post again so just skip down to FUN STUFF STARTS HERE if you don’t want the background.

Anyways, following our first night together Sarah and I exchanged numbers and flirted a little over text. We really got along. Our sense of humor really meshed well, and we used to play these rhetorical games with each other, gently poking fun at one another and trying to one up the other’s last comment.

One day while I was working on campus, she walked in just before I was leaving to go to class. She was going to the library, and while it was slightly out of the way I offered to walk her over as I had 15 minutes to make it to my class. Read more »

Quarantine Pool Day Leads to Unexpected Threesome with Wife and Sister-In-Law [MFF] (Part 3)

[Part 1 Here](https://www.reddit.com/r/gonewildstories/comments/h7ah0s/quarantine_pool_day_leads_to_unexpected_threesome/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

[Part 2 Here](https://www.reddit.com/r/gonewildstories/comments/h7aouw/quarantine_pool_day_leads_to_unexpected_threesome/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

There were no words or teasing this time. Sarah started kissing me like she had earlier in the pool. She pulled me closer to her by the hips, my cock finally springing back to full attention, ready for round two. My wife felt it and started pulling me on top of her.

I obliged, rolling us to the middle of the bed with me on top of her. Bella was still right next to us, watching through dreary eyes. My wife reached down and rubbed the tip of my cock up and down on her clit a few times. She was so turned on that my tip was coated and slick in no time.

Sarah guided me where she wanted it before pulling her hand away. I slid right in to her dripping wet pussy, her familiar lips gripping me as I entered. On the first pump I went halfway to get myself wet. The second pump went all the way into her, drawing loud moan from her and causing her to wrap her legs around me. Read more »

Quarantine Pool Day Leads to Unexpected Threesome with Wife and Sister-In-Law [MFF] (Part 2)

[Part 1 Here](https://www.reddit.com/r/gonewildstories/comments/h7ah0s/quarantine_pool_day_leads_to_unexpected_threesome/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

*Holy shit this is actually happening. Holy shit. Holy shit…* was repeating on loop in my head as we all got out of the pool and grabbed towels to wrap around ourselves.

Sarah took the lead, guiding Bella through the house to the master bedroom. She stopped at the linen closet, to my confusion at first. She ended up pulling down one of our big towels that we usually bring whenever we drive all the way out to the beach. We *were* all still wet after all.

When we got to the master suite, Sarah stopped and turned in front of the bathroom door. She handed the big towel to Bella to hold, and then casually dropped her thong to the floor from underneath the towel still wrapped around her. She gave me and Bella a wink and then took the big towel back.

Bella stayed frozen in place as my wife continued in and laid the big towel out across the bed. She turned and looked to me for direction, so I stepped around her into the doorway and followed my wife’s example. Looking at Bella the whole time, I undid my shorts underneath my towel, and then flipped them in onto the tile bathroom floor. Then I waited. Read more »

Quarantine Pool Day Leads to Unexpected Threesome with Wife and Sister-In-Law [MFF] (Part 1)

My wife Sarah (29) and I (29) have been together for almost a decade. We discussed threesomes when we were younger, but after a few years and eventual marriage I kinda assumed it wasn’t going to happen. That’s why, when what am I about to share happened, I was incredibly (but delightfully) surprised. (Names altered for privacy, and I’ll warn you this came out long enough to be broken up into multiple parts. I wanted to make sure to leave nothing out, for my own future recollection as well as everyone else’s enjoyment!)

The third subject of this story is our Sister-In-Law, Bella (22), married to my wife’s younger brother(who is kind of an asshole). They got married very young after having a baby, and now that the little one is a bit older and Bella can now legally drink, she has been catching up on all of the growing up one usually does in those formative years. Read more »

He fucked me raw part 2 [mf]

Part one [here](https://www.reddit.com/r/gonewildstories/comments/gtxd7v/the_time_i_let_him_fuck_me_raw_fm/?st=KBBHGTL1&sh=4b84bee1)

After my night of raw passion with Matt, we both got tested and I went back on the pill. We were lucky but know better than to risk it again. The chemistry between us got stronger and stronger, I’ve never had a guy have such an effect over me. We could be driving and talking and he’d innocently touch my leg or brush my arm and my body would start to get all warm and tingly with anticipation. The next couple of months we spent in a bubble of hanging out, passionate sex and late night booty calls. It was great and I was falling fast.

Before I’d even realised how hard I was falling we smashed into rocky ground. A close relative of his past away and he started to withdraw and push me away. I gave him his space but was so head over heels that I did allow some questionable behaviour to fly. A story for a different subreddit I’m sure. I know there is a correlation with a turbulent relationship and amazing sex but wow, the more we tried to end things the stronger we seemed to gravitate back to each other. Although our communication was terrible when it came to feelings it was incredibly open sexually. We started trying knew things including my first facial on his birthday and a failed attempt at anal, that somehow lead us to discover that he loves his ass being played with, which leads us to today’s story. Read more »

My Boss [F] and I [M] Part 3

Memorial Day at my bosses lake house Part 1

My Boss invited me to spend Memorial Day weekend at her lake house. Over the years, My Boss has mentioned numerous times about her lake house. It was about a 3 hour drive up north and is quite and secluded. She shares the lake home with her ex husband and as part of their divorce the two of them came upon an agreement to both share the lake home. It was her turn to have it, and I had nothing going on, so I accepted the invite.

We arrived at the lake house and she gave me a tour of her home and surrounding property. The place was exactly what she said it was, beautiful, secluded and quite. Read more »

[F]lashing in Thailand

After H and I were married a few years ago, we started saving up and went on our honeymoon in mid 2017. We had 3 weeks, half in Malaysia and half in Thailand. Given everyone was so conservative in Malaysia, we didn’t indulge H’s exhibitionist tendencies much, but Thailand was a different story.

Our first stop in Thailand was Phuket. Now I had packed a few of H’s sexier thong bikinis for Thailand. A bit of a description of my lovely wife, she’s petite but has curves in all the right places. She’s about 5’2”, an Australian/UK size 6 (American size 2). She’s got incredibly perky (C cup) boobs that are perfectly round, symmetrical and sit right up on her chest and are topped off with the most amazing dark, prominent and almost always hard nipples. They are a perfect handful. Every couple we have met has commented on her tits and both men and women can’t seem to get enough of them. As I said, she’s petite, but she has a slim wait but a big booty. I’m an ass man so I’ve got her doing squats and various other booty exercises. It’s worked as she’s gone from not having my of a booty to now struggling to fit into her pants. Skirts are often too short because of how round her booty has grown. Whenever I see her naked, I have to pinch myself and remind myself of how lucky I am to have married such an incredibly sexy woman. Read more »

Anniversary [F]lashing

It was our eight-year anniversary late 2019 and we decided to go out for dinner and drinks to the city. H looked incredible in a plunging bodysuit and a black miniskirt (see our previous story for a description of her body). The bodysuit was silver and when I say plunging, it literally plunged down to her waist. She wore a necklace that hung low in between both of her tits, drawing attention to how much on show they were. She wasn’t wearing a bra and about half of both boobs were out, not to mention her nipples were poking through the top. The miniskirt was worn high as to show off most of her legs. The skirt was already short but it was one that flared out, so it seemed even shorter given her big booty. It fell to maybe an inch below ass cheeks and depending on how she walked, her cheeks would peek out every so often.

We stopped off at a bar first and had a quick drink during happy hour. We didn’t get up to much mischief there, apart from giving the few people there a show of her skirt riding up and sticking her chest out as I snapped a few pictures of her with her wine. Read more »

My [M] memories of Squishy [F] – A twitter friend who liked aggressive sex, became a sexting partner and engaged me in multiple IRL trysts. PART 7

[Part 1](https://www.reddit.com/r/gonewildstories/comments/gzy5hc/my_m_memories_of_squishy_f_a_twitter_friend_who/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

[Part 2](https://www.reddit.com/r/gonewildstories/comments/h01pvo/my_m_memories_of_squishy_f_a_twitter_friend_who/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

[Part 3](https://www.reddit.com/r/gonewildstories/comments/h02yz4/my_m_memories_of_squishy_f_a_twitter_friend_who/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

[Part 4](https://www.reddit.com/r/gonewildstories/comments/h03cgv/my_m_memories_of_squishy_f_a_twitter_friend_who/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

[Part 5](https://www.reddit.com/r/gonewildstories/comments/h03sur/my_m_memories_of_squishy_f_a_twitter_friend_who/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

[Part 6](https://www.reddit.com/r/gonewildstories/comments/h0jbeo/my_m_memories_of_squishy_f_a_twitter_friend_who/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

Squishy and I couldn’t line up our schedules for a while so we went back to sexting a lot. She sent me a new nude pic about once a week and that always made me grin like crazy. I sometimes wondered why she wasn’t more conversational and it gave me a twinge of pain that she never really confided in me much, unless it was something to do with sex. One time she make an offhand comment that she thought she might be a porn addict. Addiction work is part of my role professionally so I was keen to explore that with her on a serious level, but she wasn’t interested. That gave me another twinge of pain, but I couldn’t help but admire her self-sufficiency. It was notable that she seemed to have no lack of friends in real life but most of her time was spent at home with her two dogs. We related to each other on that point: The two of us were definitely introverted, but neither of us was shy or withdrawn. If you’re into Myers-Briggs personality typing, I’d say she was an ISFP whereas I’m an INFP. Read more »