so essentially my mom’s best friend is this woman she’s grown up with. we’re very close family friends, and she even has a son around my (M18) age. and she also had a daughter (F27) who was older than me and her brother so we didn’t talk much but I knew her. she had babysat me a couple times when she was a teen and I was a kid. but flash forward to our trip to tahoe that we do every couple years. i hadnt seen the girl in a few years, not since I was 16 and she was 25. but she was the sexiest woman ive ever seen. she was just so gorgeous. i couldn’t keep my eyes off of her. so we’re all renting a cabin and me and her have been talking and hanging out. long story short, we ended up hooking up on the bunk. i was a virgin before that, so that was my first time and it was amazing and she was just so gorgeous. but now im in a touch situation because I’m not sure if we should tell our families about it and pursue a relationship. idk if that’s necessary or not but it’s felt very awkward this whole trip.

8 comments
  1. I don’t know how old she is but you said she has a daughter (F27) and you are (M18)

    Your age gape is quite big. no need to pursue a relationship or notify the family about an upcoming wedding.

    I assume she was helping you loose your virginity (congratulations) and if she wants more and you still need pussy go for it as a FWB only.

  2. Tell nobody. It was a secret fling, nothing else. Don’t talk about it anymore, just enjoy the memories.

  3. Not every event in your life needs a press briefing to your family. I’d say you’re free to keep this one in your private reserve. IF you start up a relationship, cool, I wouldn’t suggest stressing out about that until it seems like it might actually become a possibility.

    If you and she both loved it and also think it should happen again, then you can go from there. But it’s possible she liked it but doesn’t see it becoming a regular thing.

    What does SHE want? I suggest having that chat. If you only see each other “every couple years” it’s probably unrealistic that you’d really strike something up.

    I’d suggest letting her know how gorgeous she was and thank her for awesome memories that will last a lifetime. No need to sweat everything else. It’s a good skill to be able to keep things discrete when the situation calls for it.

  4. Don’t tell people about it until after you’ve decided it is a relationship they should know about— like you’ve dated for a while after you get back from your trip and it is going well.

    If you do end up dating they’ll probably figure it out anyway.

  5. Take it for what it was – A gift she gave you. There will be no relationship. Albeit 9 years isn’t an unheard of age gap for a relationship, I don’t think this 27 year old woman intends to enter a relationship with an 18 year, right of highschool, kid who has a lot to accomplish before he’s suitable dating material for a mature woman. Focus on you and your future. Let this be your own memory and no one else needs to know.

  6. Most likely she just wanted to fuck Nd doesnt want a relationship.

    Clear up your head.

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