i never play Ian as a cuck since that is not a kink i have. i prefer to be the one fucking the girls and taking them from other guys. especially if those guys are in any way unlikeable or just plain assholes. so i put Axel and Jeremy in that category pretty early on. so Lena and Allison were the 2 girls i had Ian with on most of my playthroughs. i did do a run where i took Cindy away from Wade, and she became really annoying after so i deleted that save and just had Ian trying to help Wade keep her, but of course, she eventually seems to be on the verge of dumping Wade for Axel, so fuck her. she is too selfish to stay with a guy that is a lazy dude like Wade is.
i never really was into Cherry either so never bothered with her. if a path comes up where Lena and Ian bring Holly into their relationship, since my main save is them in an open but loving relationship, that would be ideal. also, of course i like the idea of Ivy and Minerva having threesomes with Lena and Ian. and of course, Allison too. would be interesting to have Ian get Lena to have a heart to heart with Cherry and that result in a threesome. since Ian is not the controlling asshole that Axel is, that could work out well since Lena and Cherry have already done stuff together. would be even better to have Ian stroll into the club with Lena and Cherry on his arms and cuck Axel making him watch the three of them making out etc. yeah, i hate Axel lol.