My 3rd girlfriend when I was 17. On our first date she pulled me on top of her wanting fucked (she was known to be a guaranteed fuck). After we were finished she asked me if she felt big to me and I lied and said no (she was very loose). She said I felt small to her, then pulled up the sheet and looked and saw I was actually small and said "Well now I know why!" and laughed. She apologized and I told her I wasn't upset because I was fully aware how small it was.
We dated for 8 months and she loved making fun of it. She would do things like call it my "Wittle wee wee" or tell me to take off my pants because she wanted to suck my little dick. When we fucked she would sometimes tell me "Do it harder...I can almost feel it!"
She even rigged a strip poker game with me, her, and her best friend so that I would end up naked and her best friend could see how small it was. As my penalty for losing I had to jerk off while they watched, talked about how tiny it was and giggled the entire time.
I also ate my first creampie with her (my cum) and she told a bunch of our friends.
I should have married her lol