Obviously you should.

[Even if he didn't participate, he could be entertained by Dirk going all in. Maybe he was even relax and have a drink of alcohol.]

You aren't difficult to sell if it's dramatic.

[He snorted at the virgin comment.]

I think you enjoy popping my cherry in as many situations as possible. [He wasn't familiar with term, but it seemed amusing.] Are you... suggesting we go multiple evenings?