[M4F] Unexpected Relationship with My Tomboy Best Friend

NSFWRP/Conversation

We have been friends since childhood. I was there when you started forming your identity in elementary school, dressing like the boys and spending your time playing with us instead of sitting with the girls. We stayed linked at the hip throughout middle school and I was super supportive when you came out as Queer later in life.

It was doubly important because your family wasn't the best at handling these subjects. I opened my house to you and made sure my family made you feel welcome when you spent whole days there trying to avoid the awkwardness of your family situation.

Nothing changes afterwards, we go to the same collage and am still basically inseparable despite some difference in interests and activities. I was popular but I loved our friendship and you (not romantically yet) to let anything get in between us. It didn't matter what group I was in, be it the football team or the jocks, you always had a place with me and no one dared question your presence. You also never seemed out of place, you fit in with the boys.

But, maybe that dynamic is why I never noticed that you were in love with me. I guess on some level I thought queer meant lesbian, and it's probably true for you with one exception; me. I mean, we were basically soulmates in every way. And while you might not think men in general are IT, I've never really been part of that. Our relationship transcended that.

The problem is that I'm oblivious to your feelings like I said. I carry on obliviously making you fall in love with me while you yearn and crave me, until one emotional night you make a move.


Hey friends! So that's my story, an unlikely and unexpected love story between a tomboy and her best friend. No one expects this to happen, not even him, maybe also not even she, maybe she's always just ignored those feelings until one drunken night they explode.

I don't like angst so when she makes her move I don't want him to reject her. He never thought of her that way but he loves her enough and is, ultimately, a guy, so he'll go to bed with her. I want their first night together to be mind blowing. He can be a sexual god or not, the sex could just be fantastic because she loves him so much and he's good enough to eat her out a bit before fucking her. Whatever strikes your fancy, I'm open minded.

After that the drama will come from them transitioning into being this strange couple. I'm thinking we can even introduce cheating in there. Maybe he was in a relationship at the time, maybe her too. Their families would not expect it. His family is open minded but they never saw their son being with a girl like her. He's the perfect guy everyone expects him to be with a feminine gentle girl so this doesn't fit anyone's ideas about either of them.

This is the kink list I use, but none of these kinks have to apply in this story.

Kinks; domination in bed, different sexual positions, love, passion, kneeling blowjobs, oral, orgasm control (making you beg for it), I like it if one or both people like the sex and need it as a part of their daily life as a stress reliever or anything ,Cumming in and on you and dealing with it (not just ignore the cum on your ass and never mention it again), taboos, secret affairs, forbidden love, risk of getting caught, moaning, aftercare, staying inside the woman during sleep.

Limits: abuse, bad treatment, bad hygiene, vomit, face fucking, pornographic acting.

Posted Mar 10, 2026, 11:19 AM UTC

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