I'm a straight guy in my 30s dating a woman in her mid-20s. We've been together for a year, and I'm crazy about her. In love, even. She's gorgeous, sweet, kind, loving, and very sexual. She's perfect. In her late teens and early 20s, she had a wild sex life. She attended sex parties, had loads of NSA hookups, sexted with random guys she met online, etc. She revealed this to me slowly and carefully out of fear that I'd look down on her, but what she didn't know is that I have an intense cuckold interest. I've asked her, ad nauseam, for every detail she can recall about these encounters. The ones centering on "alpha jocks" with extremely large cocks are the ones I enjoy most. I'm a nerdy guy, definitely not muscular or athletic. I have intense fantasies of some alpha male taking her away from me, or catching her with a hot young soccer player or a good-looking musician — any guy at the top of the social pile. The idea of watching her have sex with one of them is exhilarating. But it's also gut-wrenching. I haven't told her how much I would like her to go through with an actual hookup. However, I'm certain this would not be well-received on her part; she's made it clear that she's not proud of her wild past. To complicate this, my interest in cuckolding does not come from a healthy place. I experienced a series of rejections in my late teens and early 20s, all of which involved being outclassed by better guys. The first girl I was ever in love with, who kept stringing me along, had sex with another guy while talking to me on the phone. She went into detail about how huge his penis was, how good it felt, and so forth, while I shook with envy and misery and excitement. It was a terrible, traumatizing experience, but now it rules my sexual fantasies. Is it OK to indulge an interest that likely stems from a traumatic experience? (Assuming she's willing.)
Harrowingly Upsetting Reckless Tendencies Mostly Excite
First things first, HURTME: Your girlfriend can't put this period of her life behind her — all those hung alpha jocks, all those NSA hookups — while she's with a man who demands to have every last detail recounted ad nauseam. So you might wanna check in with your gorgeous, sweet, kind, etc. girlfriend before she decides to put you behind her, too. It's possible she enjoys sharing her stories with you because your enjoyment makes her feel better about those experiences in retrospect; all those meaningless sexual encounters now mean something because they enhance the relationship she's in.
Checking in with her about how she's feeling will give you a better idea of how receptive she would be to cuckolding you. If sharing stories about her past makes her feel sexy (because the encounters were hot) and it feels meaningful (because the stories enhance your sexual connection), then your girlfriend might be open to the idea of coming home with a brand-new story to tell you.
Or she might not. Like I said, you need to check in with her.
As for you, HURTME, your erotic imagination seized on that experience — that cruel girl on the phone — and through a mysterious process that sex researchers don't quite understand, your mildly-to-wildly-traumatizing early sexual experience emerged in adulthood as a full-blown kink. There may be other boys out there who had the exact same experience — that girl could have had other victims — who don't have any interest in being cuckolded. The alchemy of kinks isn't fully understood.
There's only one way to find out if you would enjoy being cuckolded, HURTME, and that's to do it. But there are three questions (at least) that you need to ask yourself before you act: Have you built a firewall between your sense of your own sexual desirability and your kink, a kink that's about your eroticized fear of sexual inadequacy and not your actual sexual inadequacy? (You landed a gorgeous, sweet, kind, loving, and very sexual girlfriend—you're clearly more than adequate!) Are you sure you won't wind up in the fetal position on the floor after your girlfriend fucks some alpha stud? And if you do react badly, if being cuckolded in reality is painful, not sexy, can you process your feelings without lashing out at or slut-shaming your girlfriend?
A few sessions with a kink-positive shrink might help. Find one through the American Association of Sexuality Educators, Counselors and Therapists (aasect.org).