Category: gonewildstories

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 5

Having a cover story for meeting Squishy in real life wasn’t difficult. One of my hobbies is flipping collectibles on eBay, so my then-wife was used to me chasing down stuff I saw advertised on craigslist or going to thrift stores looking for treasure. So being gone for an afternoon wasn’t suspicious. And I made sure to always come home with a bunch of stuff, even if it was stuff I had found a few days earlier and left in the trunk. Now that I know she was banging the dude she’s currently married to I can see why she never seemed to resent the time I spent on my hobby. No biggie. I won’t demand a nobility of her that I myself did not possess.

Squishy and I arranged to meet one Saturday morning. By this time we had been sexting for about 3 months. I parked a block away and approached her door after she texted me to let me know that she was home from her jog. She had a big beautiful house with a large flower garden and peony bushes. She also had a porch swing, and I regret that in all our trysts we never spent any time on it. Read more »

The Redding House Saga: Room for Two [MFF]

[Part 1](https://www.reddit.com/r/gonewildstories/comments/grusxx/i_facefucked_my_20year_old_tenant_after_she/?utm_source=share&utm_medium=web2x)

[Part 2](https://www.reddit.com/r/gonewildstories/comments/gs6ei1/i_facefucked_my_20year_old_tenant_after_she/?utm_source=share&utm_medium=web2x)

[Part 3](https://www.reddit.com/r/gonewildstories/comments/gsumxt/i_facefucked_my_20year_old_tenant_after_she/?utm_source=share&utm_medium=web2x)

[Part 4](https://www.reddit.com/r/gonewildstories/comments/gtb474/the_redding_house_saga_an_unexpected_guest_mf/?utm_source=share&utm_medium=web2x)

[Part 5](https://www.reddit.com/r/gonewildstories/comments/gub9xt/the_redding_house_saga_an_unexpected_guest_part_2/?utm_source=share&utm_medium=web2x)

[Part 6](https://www.reddit.com/r/gonewildstories/comments/gwk095/the_redding_house_saga_an_unexpected_guest_part_3/)

Prior to my birthday present from Maddy… and I guess Sarah too… I had been involved in exactly two threesomes. Both were terrible experiences. It was incredibly stressful; tough to be in the moment when you’re worried about paying equal attention and making sure you’re not left out entirely. Overall, I’m definitely more of a one-on-one kind of guy… simple.

This night was the exception. My only regret is that I don’t have a picture of my face when Sarah walked out in the same tiny schoolgirl outfit that Maddy had made famous in my mind. My best guess is my face matched [Donald Glover’s](https://imgur.com/aVgTuQD) when he met LeVar Burton on Community.

“Holy shit” I managed to exhale.

Both women walked around either side of the coffee table, the sway of the skirt fabric accentuating the swing of their hips, their heels clicking in time with my now elevated heartbeat. They stopped in front of my feet, and in unison sat down on the table in front of me. In one fluid motion, they both crossed one leg over the other, perfectly in sync. Huh… did they practice this? 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 4

[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 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)

Squishy was unusual in the respect that she didn’t keep her address a secret. She lived in a historic neighborhood with really big houses that were over a century old. Her house was her absolute pride and joy, and she tweeted a lot about how she knew she was extremely fortunate to have been able to afford her house. I think she was able to afford it because of a combination of factors. I think she came from a family with a bit of affluence, first of all. (Some of her pictures as a little kid were of her on a horse doing show-jumping) Also, she previously worked for a very large financial institution, and her (ex?) husband did as well. I’m still not clear on that situation because her first husband didn’t seem completely out of her life, but at the same time, nothing about that house seemed to indicate any kind of male presence. When I knew her she was self-employed as a freelance writer and worked from home without any set hours. She tweeted a lot about gardening, jogging, and her renovation/interior decorating projects. 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 3

[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 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/user/Mrquick83/comments/h03ml7/my_m_memories_of_squishy_f_a_twitter_friend_who/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

As the weeks passed Squishy and I continued out back-and-forth. We didn’t write to each other every day. I would say I was more diligent about writing to her, but I noticed pretty quickly that she wasn’t one for long messages and she rarely expressed any interest in stuff like my job, hobbies, or deeper topics. I could see that she generally just initiated contact when she wanted to talk sexy or show off a new pic. Her Twitter DMs had read receipts turned on so I could see that she was reading my messages, but a lot of the time she just didn’t make it a priority to reply. I would say maybe 15% of my heart was annoyed by that, because it was just so different from how curious I was about her. But the other 85% of my heart had to acknowledge that it was better she was not trying to get into a deep relationship with me. It was also convenient because I didn’t want to be in a position where I was overly glued to my phone. My wife and I were in the final stages of our marriage on unrelated issues but I didn’t want the complication of having the situation with Squishy getting exposed. Read more »

[FM] Fucked my [21F] ex’s [22F] uncle [40s M] at her engagement party

This is not my usual, intimate kind of story.

People from my hometown tend to get married young. It has always baffled me, but maybe that’s because I just never really thought of myself as somebody who would get married. From the time of my high school graduation to my college graduation, over half of the girls from my high school had new last names and gilded left hands. One of them was my ex, Jillian.

Jillian got married at 22 to her college sweetheart, Mike. And although I didn’t admit it at the time, I was absolutely in love with her. We had started seeing each other during high school, our parents blissfully unaware of went on behind closed doors during sleepovers. What had originated as two girls having fun and exploring with each other turned into an addiction; we were absolutely obsessed with each other. From the ages of 14 to 18, I rarely went to bed without having spoken to her or held her at least once that day. We were each other’s first everything: our first kiss, our first love. But the small town atmosphere didn’t exactly lend itself to sexual orientations outside of one end of the Kinsey scale, so it was our little secret. 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 2

Hi there! This is part two of my recollections of the events of a few years ago, where an online acquaintance and I went from flirtation to engaging in all kinds of sexy stuff.

[Part 1 is here.](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)

After Squishy sent me that first series of nude photos I didn’t really think it would go further than that. I didnt really let my twitter friends see real-life pictures of me but I sent her one out of respect for the trust she put in me. It totally lit me on fire when after receiving the picture she replied:

“Whoa! You never said you were hot!”

Oh my God, it put me on cloud nine to get a response like that.

I told her she was pretty hot herself, and that she reminded me a lot of Emp, from the comic book “Empowered”. I sent her a few pictures of her comic-book counterpart [[This one here was one of them, I remember]](https://imgur.com/a/X19Fps9)and she said that Emp was a lot hotter than she was but she loved that I thought she looked like her. I told her that in the comic Emp has a boyfriend called Thugboy, and I always liked the scenes where he had his hands on her, which were always drawn exaggeratedly big. I asked if she wanted to see some examples that illustrated what I meant. Read more »

[MF] My first time with a stranger.

I had recently had a big breakup at my job and was feeling lonely and wanted something to do, so I signed up for a meetup of a local meetup group. The meetup was at a popular club, but there were a lot of other meetups happening all over town. I was planning to drink in the afternoon, go to the bar and get a few shots and then get a cab to my boyfriend’s place and sleep over.

I decided to go in the late afternoon and the meetup was going to be at the club from around 8. The club was already packed and I just wanted to go in, have a few drinks and leave around 11. It was hot outside and I was wearing a short skirt, so I was able to take it off with some difficulty. I didn’t get much attention from other people on my way in.

I was sitting in the corner, waiting for a cab when a guy came up to me and introduced himself as Ben. He was an older, balding man, but his wife looked much younger. She was very attractive, but he was talking to me more than I was paying attention to her. I was enjoying the conversation and the conversation was making me horny. I noticed they were getting very close, but I was still not ready to have sex with them yet. Read more »

My wi[f]e fucks her younger neighbour just before she met me.

My wi[f]e was a late bloomer but quickly made up for lost time. She explained it was sort of a pity fuck. He was a geeky short teenager. Very awkward around people. She got to talking to him one day when he came across to ask her parents about something. She had just got out of the shower and she had a dressing gown on. It fell open and he stood there staring at her boobs. She covered up but he just kept staring. My wife decided to be brave and open the gown up again. She said you could see his cock get hard through this pants. She placed his hand on her boob and told him to come back after he had showered, which he did. They moved into her bedroom and he was rock hard. She said he was average size and uncut. She guessed correctly he was a virgin so she took the lead. She started giving him a blowjob and after about a minute he blow in her mouth. She lay back on the bed and started to masturbate herself. Seeing the his cock hadn’t gone down she bent over doggy and got him close. She said she had to guide him in because he had no idea where her hole was. After a minute or so of pumping away he came again. She got a towel and let his cum dribble out of her. Still his cock was hard so this time she lay back and pulled him on top. This time he lasted for a couple of minutes before cumming. She said it was all over in about 10 minutes. After he left she masturbated with her favourite toy to bring her to orgasm.

Kinky couple [30M/29F] had first Bi [MMF] last night with random redditor [25M] (told from female perspective)

Let me preface this with a bit of a backstory. I have been with my partner for nearly 2 years, living together for 7 months. We have an excellent sex life, but I’ve been known to be insatiable at times. There’s literally never been a time that I was not down to fuck him. This led to me developing many fantasies over time just because I love and crave sex so much… having a threesome was consistently at the top of my list. Male or female, I really didnt care (though if I’m being honest, I really really wanted to be DP’d). I was always too embarrassed to ask my partner though so I just watched a lot of porn to keep me content. 

Imagine my surprise when I find out 2 months ago, that my partner is heteroflexible and enjoys giving blow jobs from time to time. Obviously, this opened my mind to a whole new realm of possibilities and kinks. I, now more than ever, needed to share another cock with him so after a few conversations, we agreed to start the search. He asked that I take the reigns and find a nice, clean guy for the two of us because since this would be my first ever threesome, he wanted to make sure the focus would be on me.  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 1

Ok, so this is a burner account because I’m going to discuss shit that my family, friends, and workmates don’t need to know about. I’ve decided to write a full account in order to stir my memories of the experience. I have broken this story into multiple parts. It begins with flirting, progresses very quickly to sexting, and eventually we engage in a lot of fucking, which I’ll give detailed accounts of.

I know you’re here for the sex, so I apologize for the fact that there will probably be a ton of unnecessary details in this story that aren’t very erotic. But I’m writing this for me, mostly, so ??‍♂️. Read more »