[MF] The One (And Only) Time I Cheated: Sleeping Between My Ex-Girlfriend And Her Friend

When I was 18-years-old, I landed my first legit girlfriend. I say “legit” because I had dated before, but never started a relationship. Tara was one year older than me at 19 and played tennis at a small college three hours outside our hometown. We had been friends for a year or two and then one day we were like, “Hm. Maybe we should fuck,” and that was the start of a beautifully dramatic relationship. Tara’s best features were her legs and ass. I suppose it was all the tennis. She had smaller than average tits and a pretty standard face. I DON’T KNOW IF THAT SOUNDS MEAN! It’s not meant to be. Obviously I was attracted to her.

Our one year relationship was a tumultuous one. It was long distance for the most part as she was in college and I was still at home. Admittedly, since I was just an 18-year-old little douche, I was a bit jealous. I thought about all the guys at her college. All the older dudes who were probably more experienced than me. My silly paranoia created a few fights, but I wasn’t the only one adding unnecessary stress to the relationship. Tara had some personality disorder. I’m not going to claim to know the specifics behind it, but her father was a high-functioning alcoholic and her mother was out of the picture. She, understandably, had some issues.

[MF] How A Post On The Nextdoor App Led To Me Fucking My Nerdy Downstairs Neighbor (PART SIX)

[PART ONE](https://www.reddit.com/r/gonewildstories/comments/ar0n5e/mf_how_a_post_on_the_nextdoor_app_led_to_me/)

[PART TWO](https://www.reddit.com/r/gonewildstories/comments/av44cl/mff_how_a_post_on_the_nextdoor_app_led_to_me/)

[PART THREE](https://www.reddit.com/r/gonewildstories/comments/avv157/mf_how_a_post_on_the_nextdoor_app_led_to_me/)

[PART FOUR](https://www.reddit.com/r/gonewildstories/comments/aytp71/mf_how_a_post_on_the_nextdoor_app_led_to_me/)

[PART FIVE](https://www.reddit.com/r/gonewildstories/comments/b0cwg7/mf_how_a_post_on_the_nextdoor_app_led_to_me/)

And we’re back. I had someone ask me why I feel obligated to continue to share these sex stories with Olivia, and honestly, it’s probably because it was you all who helped me realize I should talk to her again. Without you, I wouldn’t be having sex right now. I mean, not RIGHT NOW, but you get my point.

So earlier this week Olivia invited me to a small musical on Friday, and since I never have plans, I agreed to go with her. I also really enjoy musicals. Legit musicals, by the way. Not that La La Land bullshit…THAT WASN’T A MUSICAL, OKAY? IT WASN’T. I thought I would have to break out a tie (I only have two) for this event, but Olivia assured me it was pretty casual. Turns out, she volunteers at this theater across the city and they were putting on a special show for their volunteers and family to prepare for shows for the general audience.

[MF] How A Post On The Nextdoor App Led To Me Fucking My Nerdy Downstairs Neighbor (PART FIVE)

[PART ONE](https://www.reddit.com/r/gonewildstories/comments/ar0n5e/mf_how_a_post_on_the_nextdoor_app_led_to_me/)

[PART TWO](https://www.reddit.com/r/gonewildstories/comments/av44cl/mff_how_a_post_on_the_nextdoor_app_led_to_me/)

[PART THREE](https://www.reddit.com/r/gonewildstories/comments/avv157/mf_how_a_post_on_the_nextdoor_app_led_to_me/)

[PART FOUR](https://www.reddit.com/r/gonewildstories/comments/aytp71/mf_how_a_post_on_the_nextdoor_app_led_to_me/)

Honestly. It feels strange to have five parts to this story, lol. At this point it feels like I’m obligated to inform you all when I have sex with Olivia. Even if we’re still hooking up a year from now, I still feel like I’ll be here like, “PART 230!” I’m not sure when I should stop updating this particular story. I suppose when I get bored with it or the sex. I haven’t reached that point though, and after last night, I might not reach that point for a looong time.

Olivia surprised me last night by showing up at my door close to midnight. I was asleep. I’m usually asleep by 11 pm and wake up around 6:00 in the morning. I work from home, so it’s not like I NEED to be up by six, but I feel like it leads to a more productive day. You have more time to get shit done. More time to write sex stories on Reddit, ya’ feel?

[MF] How A Post On The Nextdoor App Led To Me Fucking My Nerdy Downstairs Neighbor (PART FOUR)

[PART ONE](https://www.reddit.com/r/gonewildstories/comments/ar0n5e/mf_how_a_post_on_the_nextdoor_app_led_to_me/)

[PART TWO](https://www.reddit.com/r/gonewildstories/comments/av44cl/mff_how_a_post_on_the_nextdoor_app_led_to_me/)

[PART THREE](https://www.reddit.com/r/gonewildstories/comments/avv157/mf_how_a_post_on_the_nextdoor_app_led_to_me/)

It’s been a little over a week since the last update with Olivia, and I’d like to tell you that this past week was filled with wild sex every single day, but unfortunately life gets in the way sometimes. Olivia is always busy and travels often for work (which is why she’s looking for a new job), so it can be difficult to connect sometimes. In the past 7 (8?) days, we’ve only been able to get together once, and sadly she had started her period.

She invited me down to her place to watch a few episodes of ‘Russian Doll’ on Netflix. I had already watched the series, but it was pretty good, so I didn’t mind watching it again with her. It was around 8 or 9 at night and she was dressed in a pair of pajama pants and a t-shirt that appeared to be over 100 years old. It had holes in it and was basically hanging off her shoulder for dear life. I made some smartass comment about it, and then she battled back with, “What about you? King of sweatpants over here,” she had a point. For some reason I think I’m Drake. I can’t get away with wearing sweatpants all the time.

[MF] My Mom’s Friend Was A Massage Therapist (PART TWO)

[PART ONE](https://www.reddit.com/r/gonewildstories/comments/axbnzq/mf_all_stories_have_a_happy_ending_my_moms_friend/)

After getting a nice release (and life advice) from Christine, I truly did change my life. It was like her stroking my dick made me hungry for success. Or maybe not even success. Just hungry for something more than I was getting. I put together a 6-month plan. I would work my ass off, save my money, and then move to the West Coast to chase my dreams.

And I did it…kinda. The 6-month plan turned into 10 months, but you can’t win ’em all. I was just happy that I finally did something with my life. I was motivated like never before, and as silly as it fucking sounds, it was all because of Christine. My mom wanted to have a going away dinner for me a few weeks before I was scheduled to leave, so I knew I would have the chance to thank Christine then. In the past nine months, I had only talked to her a handful of times because I was busy working most of the time.

[MF] All Stories Have A Happy Ending (My Mom’s Friend Was A Massage Therapist)

“You know, you’re not supposed to say ‘masseuse’ anymore.”

“Really? Why?”

“It’s associated with sex work.”

“Oh…”

When I was 20-years-old, I had probably the hottest sexual experience of my life. I was still living around my hometown at the time. Honestly, I was a bit of a loser. I knew I wanted to go out and chase my dreams, but for some reason I couldn’t find the motivation to do it. I was stuck and it felt like I was never going to get out. I spent a lot of time at home during this time. My mom was the type of person who never wanted to make anyone feel bad, which is very sweet of her, but also not the best parenting technique. She was telling me all the things I wanted to hear instead of telling me what I needed to hear, which was, “GROW THE FUCK UP! STOP TALKING ABOUT THINGS AND ACTUALLY DO THEM!”

[MF] How A Post On The Nextdoor App Led To Me Fucking My Nerdy Downstairs Neighbor (PART THREE)

[PART ONE](https://www.reddit.com/r/gonewildstories/comments/ar0n5e/mf_how_a_post_on_the_nextdoor_app_led_to_me/)

[PART TWO](https://www.reddit.com/r/gonewildstories/comments/av44cl/mff_how_a_post_on_the_nextdoor_app_led_to_me/)

Two days ago I posted the second part of my story about fucking the nerdy downstairs neighbor. I thought it was going to be the last story in the series, but you all made me realize I needed to have a heart-to-heart conversation with Olivia. Yes, it’s true. She was the who initiated the impromptu threesome, and she should have been prepared for any potential consequences. That being said, sometimes you can’t control your feelings. We all have insecurities and obviously Olivia experienced a few of them that day.

So, thanks to your advice, I decided to reach out to her yesterday. I texted her asking if she had time to talk. She replied with a simple “yes” and I said I’d be right down. I knocked on her door, she answered wearing a professional-looking dress.

“You look nice,” I said as I walked in her place.

“Thanks. I had an interview earlier.”

“How did it go?”

“Good? I think. I don’t know. It’s hard to tell sometimes.”

[MFF] How A Post On The Nextdoor App Led To Me Fucking My Nerdy Downstairs Neighbor (PART TWO)

[PART ONE](https://www.reddit.com/r/gonewildstories/comments/ar0n5e/mf_how_a_post_on_the_nextdoor_app_led_to_me/)

After the surprise fuck session with Olivia, we developed an interesting relationship. We never became “official” or anything, but it kinda felt like an actual relationship for a month or two. We would hang out at least three or four times a week, we had lots of sex, we talked to each other about our families, we went on dates, etc. But at the same time, we never locked each other up. In fact, we never even talked about it. It was the first time in my life that I had a legit friend with benefits.

Olivia and I were a sexual match. She enjoyed passionate (slightly hardcore) fucking. She was enthusiastic, vocal and was completely comfortable with her body. Sometimes you hook up with someone and you just don’t match. She goes left, you go right, and then you both go out the door. So finding someone like Olivia felt like finding a pot of gold at the end of a rainbow. I didn’t want to do anything to fuck it up…but I FUCKING DID, and this is the story of how I did it.

[MF] How I Ended Up Fucking My Improv Instructor Inside The Class Theater

My natural response to almost anything is, “no” or at least it was at one point. In my late teens and early twenties, I was a pretty shy guy. I was anxious all the time and had trouble getting out of my own head, which seems to be a common problem for people. I’m not trying to claim I was special or damaged. The only reason I’m telling you all this is to make you understand how terrifying it was for me to join an improv class. I’ve always wanted to either try improv or stand-up, but my anxiety would never let that happen. Just the thought of it would make me feel physically ill.

But here lately, I’ve been making a conscious effort to try new things, to step out of my comfort zone and live life. This is probably because I’m in my mid-20s now and feel life slipping away.

Wow. Okay, this is starting to sound depressing. You came here to read a hot sex story! DON’T FEEL BAD FOR ME! I’M GOOD, AND I’M GETTING BETTER…I PROMISE! LAUGH, SMILE, FLOWERS, CAKE, LOVE…ALL THAT GOOD STUFF.

[MF] How A Post On The Nextdoor App Led To Me Fucking My Nerdy Downstairs Neighbor

I’ve never really had success on traditional “hook up/dating” apps. Granted, I didn’t invest the correct amount of time in, but I didn’t find myself connecting with anyone. It all felt so forced and unnatural, almost as if you were expected to put on a performance for everyone. This was basically just a long way of saying I gave up on those apps a long time ago.

That being said, when I moved to a new city and found myself in an area I didn’t know at all, I decided to download the Nextdoor app. I think a friend suggested I should download it to see what was going on in my ‘hood. Most of the posts were about lost dogs, wild coyotes terrorizing the neighborhood, people offering cleaning services and the odd person sharing videos from their Nest cameras showing thieves stealing packages off their front porch.

It was a good way to pass the time before bed. It wasn’t until a month or two after downloading that I made my first post. I was walking down the sidewalk one afternoon when I saw a necklace on the ground. Finding random shit on the ground is not unusual on my street, but this necklace was clean. It looked like someone had been taking care of it, so I picked it up, took a photo of it and posted it to the Nextdoor app.