In my teen years I believed I had a small penis or average at best. I'm part Asian so I always get the small penis jokes from my friends. This is how my life was. And then I was fooling around with this girl once. We were making out on the couch and I got an erection. But I was wearing sweat pants and no underwear so the boner came through full force. She put her forearm by my thigh and glanced the shaft of my penis. She looked at me with her mouth open and said, "No wonder you don't care about people making fun of you. You're huge!" This was a nice confidence boost to the old ego. We didn't have sex anyways, but I knew she was curious.
A few days later we went out for a hike. Somewhere along the trail she pulled me to a secluded spot and we started making out. I could tell she wanted to have sex but we still didn't do it. In hindsight, this unwitting cock block of myself did me a huge favor. I think she was getting pissed that we weren't having sex. We get done with the hike and I drop her off at her car. It was the early evening. She keeps hinting that she wants to come back to my house and I tell if she wants to that's cool and if not that's cool too. She leaves. I get home like 10 minutes later and she says she's coming over.
She gets in the house, walks into the family room and we just go at it. She was a tiny Italian girl. Her tits weren't huge but in her petite frame they fit just right. A nice handful. She was wearing shorts and a tang top with tennis shoes in the hike. Everything came off except for the tennis shoes. This was the best part. I had roommates at the time so I took her up to my bedroom and we had the most incredible sex. Sex is better if there's a whole lot of pent up tension between two people. We had plenty of this between us.
I remember putting her feet on my shoulders and just going in. It was fantastic. I wish I was a stronger man with more tolerance but I will admit climaxing rather quickly. It sucked. I stopped and she said do you wanna do it doggy style and I admitted I already came. I felt terrible, so I fingered her and ate her out.
The next day I found out she told all her girlfriends--we had mutual friends--how "big" I was and how the sex was amazing. This peaked their curiosity and was a great help in the future.
This girl did a lot for my confidence. Ever since then I've been okay with the size of my penis. This girl had been with plenty of dudes, so I knew she had seen a wide range of penis sizes. That and the guys in porn are the "outliers" when it comes to penis size. In closing I think you work with what you have and get good at using your fingers and tongue.