Nah, pass. If he's worth it, you being naked can wait until YOU are ready. ?

I see nothing wrong with this, sounds like it was a blast

So he combines the sophistication and intelligence of chess, with the naughtiness and fun of ****. Actually seems like a pretty interesting time, might be a keeper lol.

Seems like you don't like the idea.. That's okay. Everyone has their own preferences. Maybe if he was your boyfriend, you'd feel more comfortable? If you don't get a good vibe from it, don't do it. I know I wouldn't be entirely comfortable sitting naked with a friend. But you know him best, so good luck!

how does that happen? "hey uh... So you wanna get naked and... Play some games???" *nude chess pursues*

So what's the problem?

That sounds fun. Keep an open mind, you might just find your new hobby.

Later that night OP will be crowning his bishop with her Maidenhead.

I see no problem here sounds kind of sexy

Assuming you are actually feeling ready for some sexy times with this guy, it sounds like fun! Not sure I could concentrate too well on the chess thou'!