I think it has been a gradual realisation rather than waking up one morning and finding out that I am a cuckold. It started with an image on the internet, this would have been when I was about 30. It was of a blindfolded women lying on her back with the huge dollop of cum on her mouth. A big black cock loomed over her, which was clearly the source of the cum. I found it on an amateur website and it instantly aroused me, which led to me masturbating. I came very quickly.
This set me on a path as I discovered more interracial porn, both amateur and professional. Slowly, my masturbatory habits changes from white-on-white porn to black-on-white until I was only masturbating to interracial. As I researched my fetish more, I discovered cuckolding. I found the combinatin of interracial and cuckolding a huge turn on. Soon it became the only porn that I viewed.
But still I wouldn't have described myself as a cuckold or as someone who had the potential to be cuckold. Then I started to analyse past relationships, wondering why they had failed, had my ex-girlfriends been unfaithful and a few times when a threesome might have happened if I had been more aware of wanting it to happen. Several girlfriends had talked about their ex-boyfriends being well-hung. These conversations felt unusual in that I hadn't raised the subject, and now I think it was their way of telling me that I'm small. I'd never really considered it before, having never seen another erection in real life. But measuring my penis, I realised that I am on the small side (I used to be a bit bigger, but now I'm 4.5in and slim).
It was then that I realised that I'm only suited for a cuckold relationship. I've had a more than a few relationships that haven't progressed beyond the first night of sex. And I realise that on some of these occasions, my penis size was a contributing factor. I doubt that any woman who would plan on remaining faithful to me would ever want to date me long term, particularly if they want the perfect package. A woman who is likely to cheat, is probably more likely to stick around, seeking other things from a relationship rather than a big dick.
This has been a 20-year journey of discovery and one day I hope that I will meet a woman who will cuckold me.