How do you seduce a friend into becoming a friend with benefits?

That's the task before me. I'm not super close with Liz. But we hang in some of the same social circles. Such that I often end up spending Thanksgiving and Christmas Eve with her. Every couple of months we end up going out for dinner with a bunch of other friends. Sometimes I even housesit for her when she's on vacation. We've known each other for about 4-5 years. And for all that time I've wanted to fuck her.

There were two times when Liz and I kissed. The first time I walked her to her car and just kind of moved in for the kill. Not a big deal. The second time, she offered to give me a ride home and we kissed in the car for a minute or two before I got out. So it's not like there has been no interest. But nothing more came of it.

Until this last Christmas. I woke up Christmas morning after having spend the previous evening with her and a bunch of other friends. I texted her from bed. I said that we should totally be having sex, she and I, because we're both single and we're attracted to each other. Besides which, neither of us want a partner. We're quite fine doing our own thing. That's where the FWB part comes in. It fits us rather well. She said I made her day, whatever that meant.

So I let it ride for a few more months. Then a few weeks ago she called me up. She was going through some personal shit. We talked for a long time. And I brought it up again. I was quite explicit. I told her that I wanted to tug off her clothes and go down on her and get her off really good. And more. She agreed that we should do it.

And now I'm to the point where I'm offering to bring over a bottle of wine so we can watch the sunset in her backyard this coming Friday night. She hasn't said yes. Or no. So we'll see. And in truth, I'm not sure I would press her to really do it on Friday. But make out a little and maybe give her cute little butt a squeeze? Yeah, I would shoot for that.

Wish me luck, everyone!