Throwaway account of obvious reasons. I (38M) work for a tech company that is a largely remote workforce. Because of c-vid restrictions, the only time I ever see co-workers in person is at industry conferences, yearly team gatherings, and occasionally onsite customer meetings. There are two separate women (42F) (37F) who I will see 2-3 times a year at different events/meetings. For the several days we will spend the evenings together and have sex. As each of us all work in different departments in the organization, there hasn’t been an occasion where both of these women have been at the same overnight event together. That’s all about to change. Our company has decided to put together a three day all company event that all are required to attend. This event is happening next week and I have no idea what to do and need some serious advice. Both women as extremely excited to sleep with me each day of the event and I have yet to come up with an excuse or tell one of them about the other. I have thought about “being sick” to avoid this situation all together, but it’s extremely important to attend this event and get face time with my team and work colleagues. Both women are very open sexually so it had occurred to me that being honest might possibly lead to a three-some, or it could lead to two very pissed off co-workers, which is never a good thing. Reddit- what can I do? Just a side note, nobody is anyone’s boss or works on the same team. There is no power imbalance in any of this situations.

10 comments
  1. So, this is just a casual work convention fling? Personally, I’d just lay it out there. I’d go with something akin to I like you both and would enjoy spending time with each of you. I’m happy to split days or do stuff as a group. Fortune favors the bold.

  2. You don’t have expectations of exclusivity with either woman, so you SHOULD be able to tell them. Emphasis on “should”. People don’t always react how you might think when it comes to sex.

    Given that you feel you really need to go to the conference, you need to tell them sooner than later. Like today if you can and realize that there is a risk of this blowing up for you. You know these women best, so you’re the best predicter here of what to expect.

    Are both of these women single?

  3. I’ll enjoy employment and not getting up locally embarrassed so I’d be telling them I’ve got a newly started mono relationship so I can’t meet up. Easy done – makes you look good and starts no work jealousy

  4. You know you can just not meet up and have sex with them right if it’s that big of a deal? You don’t have to resort to skipping or lying to them for no reason. This whole post reads like high school just act like a grown up. don’t assume they’ll be open to anything. I promise all of y’all will live without sex this weekend

  5. You see each 2-3 times a year. There is no expectation of exclusivity. Guarantee they have other guys. The problem is that each will want you to themselves. They are not going to be happy to share your time. And a threesome is not going to happen put that out of your head.

    You need to be honest and pick one. The other may or may not get over it. Because no one likes to be second choice.

    Or tell them you are not going to sleep with either of them, because you cannot choose between them, and cannot hurt either by making her the second choice. And if they are not happy about it, then they need to talk it out.

  6. Are either of these two women in relationships with other people and are cheating with you the few times a year you see them?

  7. I’d be honest if I were you. You’re not exclusive with either and you don’t need to make it tense between them, just say that you’re in a similar situation with someone else and they’ll be there too, so you’d rather not cause any friction. You might find one or botb don’t care, but even if they do feel annoyed, you won’t have them both approaching you or anyone causing awkwardness in front of your other colleagues. And remember to use protection if you’re flitting between partners.

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