I don’t know if this counts as a “gone wild” story, but thinking back, it’s definitely weird.
My wife and I have a group of “couple friends” that we hang out with frequently. One of the couples – let’s call them “Dave” and “Becky”. We’re all good friends, but I have a special connection with Becky. I really like Dave too as a friend so I’ve always felt guilty about it.
Now it’s not that Becky is insanely hot or anything, she’s pretty, but – she’s a lot of fun to hang out with, she laughs at my jokes, she flirts with me when we banter, etc etc. We don’t really obviously flirt in front of other people when we’re hanging out, but sometimes she’ll brush me while passing by me at a party, grab me from the side, etc.
I always wanted to fuck her, but obviously the fact that we’re both married is a hurdle. For us at least. I don’t want to cheat and neither does she.
I wanted to check if our “connection” was just in my head or not so I decided to randomly text her at times – sharing memes, jokes, or just initiating casual conversation from my side. She would always respond and we would get into long conversations that were deep and I guess “flirtatious” (she said she found me kinda attractive, but nothing explicit), but she would never initiate conversations on her own. So I thought it was in my head. I know it would stupid of me to push my own boundaries and that it was wrong.
However, last month, a bunch of us just decided to get a cabin for a weekend near some hiking trails in the state that I live in. There’s a small town, so the plan was to hike during the day, go out in the evening and chill / play board games at night.
There were six of us – 3 couples. My ankle got a little fucked up right before the trip, so I decided I’ll stay at the cabin while the others hiked. I had planned to catch up on work. Right before everybody leaves, Becky said she wasn’t feeling great either. She jokingly said she’ll stay behind to give me company / annoy me. I honestly didn’t think much of it, and as there hasn’t been a history of anything like this in our group no one gave it a second thought.
The four hikers (my wife, Dave, and the other couple) left, and I was alone with Becky. It was like 3-4 hours till everyone was back so it was gonna be a long time with just us. I was honestly a little excited to be able to talk to her alone, I actually didn’t think it would go anywhere. We chatted for a bit, and I said I really needed to catch up on work so I pulled out my laptop and started working at the kitchen breakfast bar.
She was watching TV outside for a bit but she turned it off and came over to me. I had a crick in my neck so I just rubbed my own neck for a second. She asked me if my neck hurt I said a little. Without any prompting she started massaging my neck and shoulders. I told her that felt good, like REALLY good. She laughed. I decided to push my luck and said it might actually be feeling “a little too good if you know what I mean”. She laughed and called me a perv. She massaged me for a bit and squeezed my love handles and butt and went back over to the couch.
I sat next to her on the couch. She started the British Baking show. I told her I’d seen it and in jest tried to change it to something else with the remote. She (again in jest) grabbed my forearm with the remote, then I grabbed arm. We wrestled for a bit and she grabbed my bicep and I instinctively put my free arm around her waist and pulled her towards me.
She leaned in for a kiss but I pulled away (yea, I know right?). She ended up kissing my neck.
She let out an audible “oh” in disappointment. I told her she shouldn’t be disappointed, and I had been feeling like there was something between us for a little while, but I didn’t know she returned my feelings. It was just so unexpected for me to see her returned feelings. Also, I really didn’t want to cheat on my wife.
She said she always felt very connected and attracted to me but she also didn’t want to cheat on her husband. We had just got caught up in the moment.
So we awkwardly started watching TV again. I kept racking my brain for how I could do something with her and it won’t be a bad thing. I decided to do something weird and I turned off the TV. She looked at me curiously. I told her that I was willing to explore what we have a little more with some ground rules so we can be morally in the clear. She asked what I meant.
I told her I wanted to kiss her but that wasn’t okay. Maybe I would just touch her.
She said she’d like that and that she’d touch me too. We then made the weirdest ground rules in history: no kissing / mouth stuff and no touching bare genitals with skin or hands.
You would think we wouldn’t be able to do much, and sure enough we held hands for like the first minute. But then we started stroking each other, her my back and me her stomach.
She then sat on my lap, fully clothed and started moving back and forth. I was wearing indoor shorts so I could really feel it. I got rock hard and tried to kiss her but she said we made rules for a reason.
She took her top off and said I should be able to fondle her breasts as those weren’t genitals. So there I was, fondling her breasts and as I got close to sucking them she batted me away saying mouth was unfortunately against my rules.
She told me to take my pants off. I said that would be violating the rules. She said “there’s nothing against me seeing it, and I’m clothed down there”. At this point she was wearing just a skirt and underwear. I took my pants off and she sat back on my rock hard dick. I told her this was definitely a violation and she said no, because she wasn’t touching my dick and she was fully clothed. She kept riding me blowing into my ear telling me how she wanted me to moan. I told her I was going to cum and she said we never said that was against the rules. I hadn’t cum for a while so I finished inside her skirt on her underwear.
I told her this was definitely a violation of our rules in spirit and she smiled and said maybe I should have been clearer. I was worried about potential pregnancy (low chance through underwear but still) and she said not to worry she had an IUD and her underwear was on.
She gave me a peck on the cheek and said it was her turn. She took her underwear off and told me to put my pants on. She rode my leg and pleasured herself until we collapsed in a heap. I was hard again, and this time she jerked me off with her skirt wrapped around me dick to “stay within the rules”.
I felt really guilty obviously, but it also didn’t feel like cheating. I told her I needed some time to think about what was going on and she said she had fun, and as long as we stay within the rules and keep our sessions limited it should be okay. I told her I was thinking this was a one time thing and she just said “yea we’ll see about that”.
The rest of the weekend passed by without a hitch. People didn’t hike the next day so we didn’t do stuff in the cabin, but while we were driving back (we had rented a full size SUV and we were sitting in the back) she rubbed her to completion from outside my pants.
I had no idea what to do. I definitely knew I’d constructed this fake “out”, and my wife would definitely be furious if I told her. At the same time it feels like harmless fun. Honestly I don’t have a bad marriage and my wife and I connect on other things and our sex life is good too. It just feels like a different kind of thing with Becky.
So over the last month, we’ve had 2 more “within the rules sessions”. I don’t want to get caught with her so things only happened in situations where everyone else was either gone for a while or not gonna show up (e.g. golf on a golf course where we split up, movie theater bathroom).
I feel terrible and great at the same time. She’s suggested she can blow me through a plastic bag next time and I can wear gloves and finger her. I can’t have that happen, how’s that different from blowing me through a condom? She’s definitely trying to push the boundaries. I dunno maybe I’ll just go through with it.