I initiated having a fwb a week ago. Part of it depends on if you want a friend's with benefits (a friend) vs. A fuck buddy (an acquaintence). I have known her for about 2 months. I knew she found me attractive and that she isn't interested in a relationship currently. We were texting and asked if she wanted to come over to watch the office in 2 days. I steered the conversation to sexual topics which we had talked about a bit in the past so that wasn't that odd. Said I would have drinks and she warned me she can get a bit annoying when she is drunk. I asked if she meant she would get handsy. She laughed and said a little, I joked about her groping me and feeling me up. Said it would only be fair if I can get handsy with her too (turns out she had meant handsy such as poking, honestly thought she meant like groping). Next day I warned her that I hadn't been with someone casually like that before. She was surprised, didn't at all realize I had meant sex. Are you sure? Texted back that's what I thought she had meant. Do you want to?

She did, we set some ground rules such as we both just wanted it to be casual and a secret. So I did use some escalation on sexual topics to get it there and deception with 'accidentally' thinking she was talking about sex. Time and consent wise I didn't want there to be any concern which is why I brought it up like that in text instead of trying to escalate it at my place.