This is another story about how I set up my own humiliation in my ignorance. My first major girlfriend Kaylie was a curly haired Irish Pawg. Our relationship sexually was defined by exploration.

One of those explorations involved using a hollowed out strap on. At this time I was pretty confident in my penis size and what I could do with it.

I think I had some subconscious awareness that it was smaller then other guys but I was in denial and years away from embracing my own humiliation. "The toys we are using are made to be big because their sex toys and the guys in porn don't exist in real life." type delusions.

For whatever reason I decided I would try out the strap on. I put my penis in and well, I swam inside the thing. It was only two inches bigger then me but it was much thicker. As soon as I started thrusting into her I saw her lip quiver and her eyes light up in a way I had never seen anytime we had sex. She moaned out my name in a higher and more charged pitch then I had heard before from her. She came. Something that was usually only possible if I spent a lot of diligent time eating her out.

I couldn't see my own face obviously but it must of been pretty contorted with pain because she asked what was wrong. I told her how uncomfortable that just made me feel. She assured me that she loved sex with me more then what we just did. Hard to believe that when you watch someones body betray their words so clearly. I felt uncomfortable almost immediately so I'm sure my face was uncomfortable the whole time and she hadn't picked up on that. Her lust rightfully overriding her recognition and compassion in the moment.

I was insecure and immature at the time so we never touched that toy again in our relationship. Now I feel bad I kept her from pleasure and could only imagine the sheer cock lust I could have seen in her eyes if I kept pursuing that uncomfortable feeling.