A guy

"Well, I know you used to date a lot of guys. If you ever missed being able to sleep with someone new, I wouldn't mind you doing it from time to time. We'd just need to talk about it first," you reply. Even though you care deeply about Lily's happiness, it's still hard to say the words. "As for what sort, I don't know. What kind of guy would you find attractive?" you ask.

Lily purses her lips, thinking.

"Well, you know I think you're hot, babe. But I guess if I were to sleep with another guy, I'd want someone different from you. Not better, just different," she insists.

"I used to date mostly older guys, but never anyone much older. It could be fun to be with someone more experienced, confident and smooth. Like old enough to be my..." she trails off. "Older than me. Anyway," she adds hastily looking to change the subject.

"Or maybe I should go the other way. Now that I'm not the teenager you totally cradle-snatched, it might be fun to try dating someone young and full of energy. Someone who would always be horny and ready to fuck me. Someone I could teach a thing or to. Someone cute and boyish, I guess" she muses.

"You could watch, you know. Watch as I make out with another guy, as I suck his cock. Maybe I'd even let him fuck me. Your cock is too thick for me to take, but if he's smaller, it might be good to get properly fucked," she admits. "We could fuck all night long and let you watch. Is that what you had in mind?" she asks flirtatiously.

"Yeah, something like that," you say breathlessly. There's a long pause.

"Well, if you ever want something like that, let me know, okay?" she says with a playful wink.