"Never. I used to feel intense frustration and anger that I can never satisfy a woman in bed. Like all tiny dick men eventually accepted my place. May I please massage your feet while we await your lover, mistress?"
"When I finally worked up the courage to ask a girl in my high school I went safe and asked out a younger nerdy kind of homely looking girl. I figured she would not realize I have a tiny penis because she probably didn't get asked out by a lot of guys. It was going really well and we started to make out in my car. She unzipped my pants and as soon as she felt my tiny little hard 3 in nub she froze. She look down in shock and said "omg your cock is so fucking tiny!" My little cock came instantly and she screams and wipes off the meager drops of semen on my shirt. She was angry and disgusted and I drove her home in shame not saying a word. When I dropped her off at her house I was almost crying and I asked her not to tell anyone. She smirked and said yes sure. The next day half the school knew that a tiny little cock and I premied in my pants"