[M4A] - Slow Transformation from Friend to Cocksucker

We've been friends for a while and hang out pretty regularly. But a night of drinking makes us a little too bold and reckless: we end up betting on something stupid with the loser giving the winner oral. The mood stays light until the bet comes up in my favor. The sudden, sobering reality of the situation settles in as a quiet tension builds. We break the silence at the same time: me telling you that you don't have to; you sheepishly saying you'll do it. We go back and forth for a while before compromising on you blowing me for just a few minutes and calling it a night. 

A few weeks go by before we chill again, and there's clearly an awkwardness that wasn't there before. After dancing around the issue for way too long, you bring up the bet. To both our surprise, you blurt out that you want a do-over bet because last time was a fluke. Outwardly, I'm reluctant and vocalize my worry that another round might do lasting damage to the friendship. Beneath that showing, I'm excited about the prospect of another round and already figuring out ways to stack the odds in my favor. You meet my reluctance with boldness and up the ante: winner gets oral to completion this time.

We'd go from there with the idea of you continuing to lose each successive bet but refusing to give it up out of pride. Since coming up with new bets each time is hard, we'd pick something we do regularly during hangouts. Eventually, we don't bet during one hangout but still do whatever activity we usually wager on. Once we're done, you just kneel and start sucking out of habit.

I'm open to other suggestions/scenarios that lead to the same end goal.

Stats: 30, 5'11, mixed race w tan skin, 7", bald and clean shaven; average build

Please also include your stats in your first message so we can both visualize better.