The idea is honestly really interesting, but we'd have to see how far Jess is willing to have a sort of "cuck" fetish. I mean, maybe she's alright with the whole sharing idea, but it's not something she particularly enjoys, and that wouldn't be a bad thing. Let's see how
Remveer's approach will be. Still, what
JoeTheMC84 is very peculiar indeed, although I think that for a "first time", it's better between only the MC and the girl. Like the case you've mentioned with Seph, I think it's best if their first time together is brought with certain intimacy, it's quite a remarkable moment after all. And, while the idea with Jess sounds cool, I think it would taint a bit a moment of "deflowering", for a lack of a better word, so it's best if it happens once another relationship has been "settled."