Nothing pleases me more than guiding a new sissy along the path to femininity, helping an eager and excited girl-in-bloom look on the outside just as she feels on the inside. It is this enthusiastic love for all things girly that was completely ignited on a recent three-hour shopping trip with a wonderfully fabulous sissy who only needs something very basic and simple: a girlfriend who understands and appreciates her desire to dress and feel like a beautiful, sexy, and sophisticated woman. She needs a guiding hand and gentle support in building her wardrobe and learning to maximize her efforts to dress well – and I have very readily and warmly extended an open invitation to be her mentor in this crossdressing endeavor. Continue reading Shopping with My Sissy: Panties and Bras and Hose… Oh My!
You now understand that you were meant to be a cuckold. Being a cuck is your true position in Life, and the more you think of the woman you love being fucked and filled by a big cock, the more you begin to experience a flurry of colliding and opposing emotions. One moment you are utterly humiliated because you know your small dick will never be enough to satisfy your partner. You feel helpless because your lack of size is beyond your control to change or correct. The embarrassment of another man being aware that you must defer to him the enjoyment of pleasuring your partner’s pussy because he has what you do not is overwhelming. You also find yourself experiencing feelings of great jealousy at the prospect of your woman being fucked and filled by another man. It’s not that you’re wanting her to fuck other men out of some voyeuristic kink of yours, but rather you want her to experience the fucking, filling, stretching, and pussy pumping that you cannot give her with your nub. Perhaps this jealousy spawns anger, shame, guilt, and/or other negative feelings, but… Continue reading Cuckolding and the Humiliation of a Small Dick (Part III): The Thrill and the Angst
Nothing pleases me more than guiding a new sissy along the path to femininity, helping an eager and excited girl-in-bloom look on the outside just as she feels on the inside. It is this enthusiastic love for all things girly that was completely ignited on a recent three-hour shopping trip with a wonderfully fabulous sissy who only needs something very basic and simple: a girlfriend who understands and appreciates her desire to dress and feel like a beautiful, sexy, and sophisticated woman. She needs a guiding hand and gentle support in building her wardrobe and learning to maximize her efforts to dress well – and I have very readily and warmly extended an open invitation to be her mentor in this crossdressing endeavor. Continue reading Shopping with My Sissy: Panties and Bras and Hose… Oh My!