So this happened to me 9 years ago. I had been seeing this woman who had been in college across the state (we’d visit each other back and forth). My birthday is at the beginning of June, usually a month after finals are over and everybody heads home.
Well I bet her that she’d break first and would initiate sex before I did when she came back. She took me on it, asking what I wanted in return. I told her if I won, we try anal, to which she agreed. Her counter was if she won, I had to make time every day for a week to eat her pussy with no return gratification. I was cool with it. Rules were simple, no penetration of any kind, no orgasms, we weren’t allowed to masturbate, but we could tease each other.
She tried her hardest, nibbles on my ear, taking me for a walk down a new trail in town and giving me a lap dance on a bench with a scenic view. She purchased a set of butt plugs, deciding to practice in case I won, but also used it to tease me into breaking. She wouldn’t properly masturbate, only enough to get the plugs in. She’d leave one in during dates, run of to the bathroom to take a picture, and then send it to me.