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Thanks for the newbie advice, all - her first tentative experience is scheduled for Friday! Further advice welcome.
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Hi all, about a month ago I made an advice seeking post and several of you gave very helpful advice. Thank you!

After trying out a few different avenues to find a possible partner (and dealing with a lot of flakes and pic collectors--you warned us!) the idea we (43F, 40M) landed on was to arrange an erotic massage. She absolutely loves the massages I give her even though I am relatively unskilled. We found a guy who is (claims to be, at least) experienced in the art both of massage and of being a third. He's younger (31) which is a turnon for her, and she's attracted to him based on pictures and a video call.

We've reserved a nice hotel room for Friday night. The plan is for the three of us to meet in the bar for a vibe check and to get comfortable and then go to the room when she's ready. He seems into her and has been super respectful. She is willing to go as far as oral with him if things go well but definitely does not want to have sex on this first foray, which he says he is okay with. And he actually respected her specific requests not to receive a dick pic or be pressured to send him nude pictures, which made him damn near unique among the guys she/we talked to. He also provided clean STD results from last week.

As I said she did a video call with him a couple days ago but who knows, there might be ways for people to fake even that. If he doesn't show up we'll still have a nice room to ourselves for the night and she'll get a massage and her brains fucked out by me. Not a bad worst-case scenario!

We settled the details with him on Sunday and she has been incredibly nervous and also incredibly horny ever since. He understands she might back out at any time, which she might and I fully support her either way.

Is there anything stupid we might be about to do that I should be warned about here? I feel we've done the best we can to arrange a safe and discreet opportunity for her to experiment with her sexuality and hopefully have fun. But we're utterly new at this.

Thanks again for being a great community. I'll post over the weekend and let you know how it went!

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4 months ago