Author: Jackalopper

The not-so-vanilla fucking of my ex-wife’s Best Friend after the divorce [MF]

Lynn is my ex-wife’s best friend who, for lack of better explanation, I got in the divorce. My ex and I didn’t have a particularly nasty break up or anything, she just treated people like Lynn, myself and the rest of our friends like shit. To recap [my last gonewildstory](https://www.reddit.com/r/gonewildstories/comments/jhehr0/i_got_my_exwifes_best_friend_in_the_divorce_mf/) from last week, I had a particularly rough week and Lynn and I ended up hooking up back at my place. We had various types of oral, vaginal and multiple orgasmic finger fuckings. We ended the evening with a hot round of anal were she ended up going home pleasantly sore, regretting nothing and wanting more.

Pretty much from the moment she woke up the next more, Lynn and I were sexting and making arrangements for the next time we would meet. It ended up being a few days later where we hooked up again. I got a killer bj and she got finger fucked into an orgasmic bliss (she was still too sore for actual fucking from days earlier. Even that was almost too much for her). That’s about the extent of our hookup evening. We watched some Netflix the rest of the night and cuddled until she had to go home. Read more »

I got my ex-wife’s Best Friend in the divorce – [MF]

I’ve been in the process of going through a divorce for some time now. My ex and I are attempting keeping it as civil as possible but it’s been a rough 2020 for me. I’ve had a lot of support through my brother and extended family which has helped me through the hard times. But, I haven’t been with anyone since my ex-wife.

Lynn is my wife’s best friend who basically chose to side with me instead of her due to circumstances that led up to the divorce. We had been casually communicating and calling each other over the phone, nothing too serious or sexual in nature. Maybe occasionally flirty but we had done that when my wife was around and it was all in good fund. She is a cute, 5″3′ thic girl of Thai decent, with a sordid past that my ex-wife described as “wild college days that extended into the rest of her 20s”. Read more »

[MF] How we almost got caught at the soccer game [public] [mild kink]

Read a story that made me remember about an experience a few years back.  Never really thought it was /r/gonewild material because of how that morning started.  That is, until now. My HS sweetheart and I have a complicated past (wrote about her before but not needed for this story). We aren’t compatible romantically but remain FWB when the urge arises.  It had been nearly every weekend for a while but life prevented us from seeing each other for well over month.  I had given up texting Julie earlier that week when I finally got a reply, “can’t make it, [Ex’s name] bailed again. Saturday is [her son] soccer game at [Regional park next county over].” I knew that Julie and her ex were having problems but 3 weeks of him bailing was not good. I could tell she was beyond stressed. I knew it wasn’t my business but my caveman brain actually processed beyond what was conveyed to me in text. I saw through her words.  She still wanted to meet but couldn’t because of Mom duties. Ok, just be a friend to her then.  Read more »

[MF] Office fling when we thought we were going to be fired [kink],[oral] Part 1

This story comes in multiple parts (the reason I’m posting this first one is because of what just happened recently).   
It starts during the early days of the 2008 Financial crisis. Understand, the feeling of uncertainty, not knowing if we will have a job the next day, co-workers getting pink slips in mass waves, we were all on edge during the early days. My company was in transition and consolidating multiple branches into a new location.  Most of the staff/processors who didn’t get let go were temporarily moved to our Headquarters across the county while our new location was in the final stages of being renovated.  Our branch was now a skeleton crew of essential only personal.  In fact, the first time I even met Avery was at the town hall meeting after the 2nd wave of layoffs.  Upon recollection, she was not one that left any impression with me other than she was rather plain-Jane looking. She did have an attractive hourglass figure going for her but rather shy with new people. Avery lost most of her friends in the layoffs and employee move the previous months. Again, that was just my first impression of her.  That all changed one fateful evening when I volunteered to drive her home because she had continuous car problems and her friend bailed on her.  During the ride to her place, I found out we had quite a bit in common.  TV shows, foodie stops, even hobbies we shared (obscure animation, not just Disney).
From that day forward, going into work was just a little bit better knowing we both became friends.  We both found excuses to visit each other at our cubicles throughout the day, even started taking lunches together.  Neither of us were dating at the time and given the atmosphere, neither of us were really looking.  At that time, I considered Avery just-a-friend because “Don’t shit where you eat” was a saying engrained in me from my childhood. Read more »

[FM] An evening over twelve years in the making [long, anal, kink, pics] part 2

Part 1 found here](https://redd.it/60b6jf)

Julie was bent over my bed, her wrists restraint securing her arms together behind her back. Her ankles were similarly bound while spreading her legs wide to the posts of my bed. I was gently playing with the butt plug that was still firmly lodged in place. Fingers expertly pulling it out with the greatest of ease and letting her own pressure suck it back in. The gasps and moans she let out were satisfying to both of us. I loved pleasing this woman. Her occasional protests of “…please… uhhh… fuck me” only renewed my constant state of arousal. I *needed* this night to last as long as I could. I used this slow teasing to rest my weary arms and hands from seemed like a marathon vibrator assault from earlier. I kept the momentum going so that I could build her desire into something more.

During the previous two weeks, our sexting divulged quite a bit of the *intimate habits* of Julie. This woman loved sex and self gratification was her preferred method of choice given her circumstances in recent years. I had a rough idea of how much she could take without making her pass out into pleasure coma. It wasn’t much of an idea mind you, but I could tell the secure woman that she was could take a bit sexual appeasement before succumbing to exhaustion. Read more »

[FM] An evening over twelve years in the making [long, rom, toys, anal, bond] part 2

[Part 1 found here](https://redd.it/60b6jf)

Julie was bent over my bed, her wrists restraint securing her arms together behind her back. Her ankles were similarly bound while spreading her legs wide to the posts of my bed. I was gently playing with the butt plug that was still firmly lodged in place. Fingers expertly pulling it out with the greatest of ease and letting her own pressure suck it back in. The gasps and moans she let out were satisfying to both of us. I loved pleasing this woman. Her occasional protests of “…please… uhhh… fuck me” only renewed my constant state of arousal. I *needed* this night to last as long as I could. I used this slow teasing to rest my weary arms and hands from seemed like a marathon vibrator assault from earlier. I kept the momentum going so that I could build her desire into something more.

During the previous two weeks, our sexting divulged quite a bit of the *intimate habits* of Julie. This woman loved sex and self gratification was her preferred method of choice given her circumstances in recent years. I had a rough idea of how much she could take without making her pass out into pleasure coma. It wasn’t much of an idea mind you, but I could tell the secure woman that she was could take a bit sexual appeasement before succumbing to exhaustion. Read more »

[FM] An evening over twelve years in the making [long, oral, bond] part 1

Skip down to the [——–section———-] if you wish to start with just the sexy stuff. The story builds up the passion and intensity for which we felt and why it was amazing for the both of us. It’s kinda worth it.

I’ve known Julie since our first class together in Jr High school. She was the drama club and choir geek while I was the chess club attending anime nerd. We didn’t actually date until the middle of our senior year of High school and even then it took us until the end of the entire semester for us to lose our virginity to each other. Once we graduated however, we attempt to make up for lost time by making love at every opportunity during that summer break of HS freedom. It was puppy love, it was innocent fun and the two of us thought we were made for each other. She had been accepted to a school on the opposite coast and I was staying local with Junior college. The countdown to her trip was slowly approaching so we stepped up our game a bit and tried doing new things. We introduced toys into our sexy time, braved some outdoor stuff at night, even took some tips from Alanis Morissette and went down on each other in a theater. I still can’t watch Lilo & Stitch without remembering her bobbing head going down on my dick in that nearly empty theater. Oh the memories. Read more »