I first realized mine was small during college when I was having an incredible night with my girlfriend. I had teased her all night, which led to a massage, which led to me eating her out, and finally, fucking her.

A few minutes into it, she started asking me to go deeper and then became visibly frustrated and almost yelled “DEEPER!” Finally, in an exasperated tone, she goes “go grab my dildo from the bottom drawer.” So I go get the dildo and it’s literally twice my size. She proceeded to fuck herself with it and shoved my face into her pussy, making me lick her clit while this huge dildo went in and out right in front of my eyes. I was too intimidated to say anything so I just kept eating her out until she came. And she came HARD.

I had heard the "size doesnt matter" phrase from other girls before but this experience just cemented the fact that it clearly matters. The orgasms are just different from what I can tell. I think this is what started my cuckold/hotwife kink.