So I've been lurking here the last few days reading various parts of this thread trying to figure out what's going on and how to progress.
I'm playing version 0.8 and I'm on the Lisa GF path. After Kira started teaching anal at night, but before the anal sex in the kitchen, I was doing private punishments for Lisa when the handcuffs came up. After talking to Kira and doing the dominance scene with Kira and Lisa at night, I ordered the handcuffs and did the dominance scene at night with Lisa. Then, like the next day, Lisa's virginity came up in dialogue and in the Mentor question description. I talked to Kira about it, and she told me to talk to Lisa about it, so I did. Lisa brought up wanting romance, and said that we'd have to stop our sex games to pursue that but she'd be willing to think about it if I could prove I was a romantic boyfriend.
Then...I dunno what happened. At this point, Mentor says I'm at the end of the opportunity, but Schoolmate says I need to progress in Mentor to unlock any more of Schoolmate. I have no idea what to do.