Going on a second date tonight. My second dates almost always end in sex (like many, but not all, of my first dates) and this time I'm determined to do something a little different. I want him to mess me up a bit.

I don't want to go overboard because I don't want to freak him out but I'd like to get a bit beyond the usual lick off chocolate/whipped cream. All I've been able to come up with for tamness is to have him pour those substances into my panties and then go from there (of course he will clean it off!). Any more creative ideas for a way to ease him into it?

This isn't someone I see myself with much of a future with, so utmost care is not crucial. But I do want to see where this goes.

Unless he seems like someone who gets freaked out easily, you could probably go further with him. Most guys are willing to be pretty adventurous as long as you also reciprocate and give him something he would also enjoy (eg. sex). Just make it clear that this really turns you.

Of course, it might be harder to convince him to let you tie him up and mess him first. But he'll likely be open to messing you up (and then letting you return the favor).

I used to be nervous about telling dates about my kinks. But now I find it exhilarating to be more open about what turns me on.

Have fun!

You might be able to pull it off if it is a small mess like that, but I like to play it safe until I've had one (more of less) vanilla session to gauge their kinky sensor.