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Family Drama

Woman Hooks Up With Best Friend on Ski Trip, Now What?

📅 December 29, 2025 👁️ 34 views ⏱️ 4 min read
A woman’s innocent spooning session with her best friend of 6 years escalated into oral sex after a night of drinking on their ski trip. Now she can’t stop thinking about it and wants more, but he’s spiraling with shame and regret about crossing that line.

The Original Post

I went on a ski trip with some hometown friends, been friends for around 6 years now and we are all very very close, i consider them family. we crashed at airbnb afterwards, everyone was drunk, same old same old.

We were all joking about teabagging (if you dont know what that is look it up) but my best friend didnt know what it was even though we game together and he does it on the bodies all the time😭 but we both like to take jokes a little too far.. so we started fucking around with our other friends and got them thinking that he was going to teabag me that night just to see what it feels like!

we shared a bedroom which is normal, its never turned into anything other than us maybe leaning on each other a little bit. but he started getting heated about some family stuff in his life and we started talking about some very deep parental stuff.

we were looking up at the ceiling and his arm was around me, it felt wholesome because we both just started opening up about why we are the way we are and it was pretty amazing for those 60 minutes.

then he wanted to take shots.

we took maybe 3, he grabbed a beer, and we were back in bed.

its 6am at this point and i suggest we just go to sleep. then he mentions spooning! so im like..

“sure!” (cause who doesnt like a good spoon!)

so he starts to spoon me, then asks

“are your tits actually big or??”

mind you, i lost a LOT of weight the past 2 years and they’ve noticeably gone down a few cup sizes so i was said,

“i mean, theyre not as big as they used to be which sucks, but i like em.” (perfect C’s cant complain)…

he grabbed my boob..

then he brings up teabagging again. he sits on top of me and i start hysterically laughing cause wtf is going on. then he just whips it out. and its just STARING AT ME. I AM LOOKING AT MY BEST FRIENDS D\*CK WTF

he said, “im not squatting on you but wtf would this feel like”

“WELL LETS FIND OUT SHALL WE??”

it turned into me sucking his dick for 20 minutes straight.

I actually enjoyed it way more than I ever have, i was very, very, VERY shockingly into it. when we woke up he wasn’t soooo happy?? he had a weird shame spiral because we’re close friends and was freaked about what it meant and how its going to change our relationship even though WE SHOOK ON IT, WE SHOOK ON IT!! TO NOT TO MAKE IT WEIRD MULTIPLE TIMES (which it wont be im rly good at not making that type of thing weird ESPECIALLY with him) but wow.

this was some monica and chandler go to london type shit.

I’m not looking for a relationship necessarily, i dont even know what i want out of this. but it really shook something in me and i want more?? i just keep replaying it nonstop and i dont know what to do. im going to see him today and tell him i liked it obviously but i hope he doesnt get freaked out, (i kind of want him to want it too i would love to see where this can go)😭

What Reddit Said

Reddit’s response was surprisingly lighthearted and supportive. Most commenters found the story entertaining rather than concerning. However, they were divided on whether this was the start of something beautiful or a friendship about to implode.

The top comment humorously noted the gender confusion from the story’s beginning. Meanwhile, other users shared their own experiences with friends-to-lovers situations. Some warned about the risks, while others encouraged OP to pursue her feelings.

The Verdict

The consensus: when you’ve hooked up with best friend, honesty is the only path forward. Reddit largely supported OP telling him how she feels, despite the risks. This represents a classic relationship dilemma where friendship and romance collide, requiring careful navigation to avoid losing both.


Original post from r/TrueOffMyChest (1,087 upvotes, 83 comments)