Relatively early on in our relationship, my then-gf, now wife and I were indulging in my hotpast kink. Once while making out she wrapped her hand around my cock and I managed to whisper out the words 'tell me about the biggest cock you've ever had'

She couldn't remember his name but it was a guy she had a brief fling with in her mid-twenties. She had just moved to a new city and was looking for a boyfriend on OKCupid, Plentyoffish etc

She had already been with a decent amount of men during college and after (20ish) but when they hooked up after a few dates, he had by far the biggest cock she'd ever seen.

She described it as 5% painful and 95% amazing. They never settled down as exclusive partners but they would see each other every once in a while for a few months to hang out and fuck.