I originally posted about this a few weeks ago, but I got spooked and deleted it so here’s a summary and an update:
My boss at my job of 7 years is, at this point, a friend — I’ve had dinner with his family many times, attended BBQ’s at this house, etc. In that time I’ve seen his daughter evolve from an awkward teen to a drop-dead gorgeous 19-year old bombshell. I wouldn’t say she and I are close exactly but she’s always been very warm and friendly towards me and in the past few years she’s added a playfully flirtatious edge (all above-board and nothing scandalous). She has my cell # from a time last year when we coordinated a surprise birthday party for her father, but she’s never privately communicated until recently.
So flash-forward to fall 2020. I’m aware through my boss that she’s doing college remotely from home, but we haven’t been in touch. And then one day, out of the blue she sends me a video of her posing in a bikini on her bedroom floor. She pretends it’s by accident and we had a friendly laugh over it but it obviously was meant for me because now she sends one every few days — usually “trying on” some ridiculously sexy outfit or overflowing out of a tiny bikini, and always with a friendly note like “hey there :)” or “how have you been?” and so on. We always chat back and forth for a bit, and I make sure to compliment her and express approval without being too overt. So clearly the ball is in my court to make more of this. And I am very, very tempted. But the combination of my job, my family, and maybe just a lack of courage on my part has kept me from trying to arrange a private meet-up.
So, I am not sure what’s next for this. But if nothing else, simply receiving these videos is an incredible treat.
Source: reddit.com/r/gonewildstories/comments/jof9d2/mf_my_37m_bosss_daughter_19f_keeps_sending_me
Thanks for sharing. Keep us updated. Does she look similar to any particular celebrity?
Dude, if u r single go for it. But if u r married don’t
Do not attempt. You may loose your job , friend, reputation. She serme like a teenager looking for adventure without thinking the consequences
Risking losing your job and family over some sex that will lead to nothing most likely is such a bad move.
I said don’t ever eat and shit at same place. She 19 and she might used it against you if you ever fuck her and if your married. Your life over if she tell your wife. You should know that teen isn’t always the most mature and rational adult. It’s a trap. If you wanna screw a teen, pick one who don’t know you. It’s your own funeral
Hit it. Asap
Age difference is wack. Just because it’s legal doesn’t mean it’s right.
I never say this, but this might be one of those rare occasions that the wanking is better than the actual experience, unless you aren’t a person who feels guilt.
I’m sure the sense of danger makes it even more tempting, but beyond the professional consequences, if your boss is really your friend then don’t do it
If I were you, I’d stick with r/gonewilde/ . Follow up after she turns 21 or you change jobs.
Dude, I was in a similar situation (not daughter, it was the boss’s niece I had met at a Christmas party). My situation was a little different though because she did not live with the boss or interact with him nearly as much as I would assume your boss and his daughter interact. Also, I was not married, but I had a gf at the time. I did actually end up giving in after the snaps she sent got more and more explicit and even though we saw each other every few weeks for a few months, it eventually ended when she moved cities and I eventually committed more fully to a new relationship. Tbh, it was worth it because she was fine af and no one found out about it. I’m still working for my boss (partner at a firm) btw.
Edit: any chance I can see how this chick looks?
Play it cool. Have an exit strategy if your boss ever finds out (or is told)