Dear Mistress Peyton,
Being a cuck boy would be both painful and exciting. Sometimes emotionally painful, sometimes physically painful, often very exciting too. 
It’s emotionally painful to know that i am not up to the task of sexually pleasing a Woman because i am too small and dribble too quickly. It is emotionally painful to see Her be so sexually aroused by a real man’s cock when She couldn’t care less about my pathetic little cocklet and swollen, achy balls. But it is really exciting to hear Her moan when his cock stretches Her pussy open and slides completely inside of Her pussy. It is painful to watch Her tiny pink pussy open and accept that real man’s cock because it is a visual reminder that Her tiny pink pussy can stretch and fully take that big hard cock and that She would likely not even feel something so small and pathetic like my tiny cocklet inside of Her pussy. Seeing that up close like that makes me realize that i don’t deserve to put my tiny cock in a Woman’s pussy. Ever. But hearing Her cum and have a very strong orgasm is one of the most delightful sounds on earth.
Hearing Her beg for his cum to fill Her pussy is exciting and humiliating too. Especially knowing that one of the jobs of a cuckold is to clean Her pussy up after they done fucking. The pleasure of having my face buried between Her thighs and licking Her pussy is coupled with the emotional pain of licking my sexual superior’s semen from Her pussy. It is all cummy, wet, sticky and his ownership of Her pussy is dripping back out into my mouth. Hearing Her laugh and taunt me for being a submissive loser and licking his cum from Her is painful too. Having Her ride my face until She orgasms again is incredibly exciting, even as i am tasting his sperm in Her pussy.
Having Her tell me that because i am unable to please Her pussy that i do not deserve sexual pleasure and sexual release can be both emotionally and physically painful. Being teased over and over again by eating Her pussy, worshiping Her ass, sniffing Her panties and wearing panties for Her is very exciting, but that is coupled with the pain of being denied a release and having swollen and achy balls that are filled with unspent loser goo for Her amusement.
Knowing She tells all of Her girlfriends causes angst and emotional pain which is intensified when they see You and giggle, Her girlfriends all knowing that She doesn’t fuck you, but She fucks real men with real cocks and then has me lick Her pussy clean. There is also emotional and physical pain when She doesn’t trust that i can control myself when She isn’t around and She feels that it is necessary to lock that pathetic little thing in chastity to ensure there is no unpermitted masturbation or ejaculation. The almost constant denial results in constant arousal and physical pain when She is teasing me with Her pussy and ass and when i am worshipping Her body.
As always, Your questions are very insightful and it’s very true that cuckolding is an interesting dichotomy of pain and pleasure…
Wow, so refreshing to see a Dominatrix being so real. She obviously is the real-deal lifestyle fem-dom that understands the right way to have a D/s relationship. Has the right idea (in my humble opinion) of the roles of both dominate and submissive partners in any interaction. I would consider myself extremely lucky to have Ms. Peyton in my life in any capacity…and thrilled at any opportunity to serve Her. And of course, I would be eager to please, amuse, entertain Her, or whatever She was wanting.
it at Your feet, Your feet playfully nudging and pushing my genitals. I am told next to kneel. You command me to look into Your eyes as You explain the new life You have fashioned for me: complete submission to You, Your control is total, dictating my activities, and taking ownership of my finances.
