[TheYesList] Kenna James (Proposing Anal / 06.22.2026)

Mila (Kenna James) tells her boyfriend Bryce (Damon Dice) that she wants to talk to him about something. Mila seems so serious that at first Bryce is worried she wants to break up with him, but she assures him that's not what this is about - she's actually interested in trying anal sex. Bryce is surprised, but open to the idea. They're happy and satisfied that they were truthful and transparent about the topic, and think it bodes well for their relationship and the quality of their intimacy. After making various preparations, the day they've chosen for their first anal sex session arrives. Mila shows Bryce the lube and various anal sex toys she got for the occasion, and with that it's time to begin. They have exploratory anal sex, with a bit of fumbling since they're new to this, but Bryce keeps checking in with Mila to make sure she's comfortable and that they're both having a good time.