It has taken me a while to answer this question because I wanted to do it justice by discussing it with him first.
There’s a lot of complexity to this for him and I’m wondering how many of my followers can relate.
Like many men with average sized penises, at a young age my boyfriend began comparing himself to the enormous penises he saw in pornography and started to wonder if he truly measured up. Confusing mixed messages about whether or not size mattered to women combined with a total lack of sexual experience brought on a feeling of inferiority. The logical part of him always knew better, but an irrational and passionately fearful part of himself always worried that his less than “perfect” penis would result only in humiliation and heartbreak. He worried that his lack of porn star level sexual performance would frustrate and bore any potential lover, quickly resulting in her not only leaving him but spreading the word. It became a fear of personal and social destruction and humiliation, caused by something he felt he had no power over.
Because sex and sexuality are unfortunately so taboo in our culture, these were feelings he was unable to express anywhere, with anyone. He felt there was no safe place to discuss his feelings, no safe haven where someone who knew better might have been able to soothe his concerns and put him at ease. Forced to internalize these obsessive fears with no outlet, they eventually began to express themselves sexually.
Cuckolding: “she deserves better than what I’m able to provide.”
Chastity: “I don’t deserve pleasure because I can’t provide it.”
By the time we got together he had been able to logically overcome these fears, but on a deeper gut level they were still very much a part of him. Because he was forced through a lack of any more viable option to deal with his fears through sexualizing them, turning him on by mocking his penis is a way for me to participate in his healing process. It’s not just something sexual, it’s something loving and liberating.
When I humiliate the size of his penis, and tell him that it’s small or pathetic, there is an implication behind those words.
It’s not just, “You have a pathetic little dick that can’t satisfy me.”
What is communicated is, “You have a pathetic little dick that can’t satisfy me, and I love you anyway. It doesn’t matter. You mean more to me than that.”
I’m not telling him he has a small penis out of spite or disappointment. I’m not pushing him off of me, shaming him about it, or trying to make him truly feel bad. I’m saying these words and yet we are continuing a powerful and loving relationship together.
Rather than using his fears to make him feel bad, I’m turning it around and using them to make him feel loved, accepted, and turned on.