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Shopping with My Sissy: Panties and Bras and Hose… Oh My!

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!

Cuckolding and the Humiliation of a Small Dick (Part III): The Thrill and the Angst

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

Cuckolding and the Humiliation of a Small Dick (Part II): The Realization That You Are Meant to be a Cuckold

Attention, future cuck! Whether or not you want to accept it, you know that your small dick is simply not enough to satisfy your woman – or any woman for that matter. Maybe you’ve seen more subtle signals such as her growing lack of interest in sex with you or going out while you are left at home. Perhaps she has decided to cut to the chase and be clear about your inadequacies and her resulting frustration, so she tells you that your cock is too small for her… or she begins talking about her ex who had a nice big dick. In any event, you get the picture, and it is crystal clear: Your teeny weenie has been vetoed. Permission to fuck denied! Continue reading Cuckolding and the Humiliation of a Small Dick (Part II): The Realization That You Are Meant to be a Cuckold

Cuckolding and the Humiliation of a Small Dick (Intro): Dispelling Dick Myths

Before we delve into the world of the novice cuckold, let’s establish a couple of facts about your dick size – and differentiate between what you think and what women want: Continue reading Cuckolding and the Humiliation of a Small Dick (Intro): Dispelling Dick Myths

Sissy Essentials Continued: From Strap-On Sucking to Dildo Fucking

You’re on your journey to becoming a sexy, slutty, strap-on sucking sissy, and you’ve been spending hours on your knees with your mouth filled in order to show your enthusiasm and dedication to evolving into a top-notch, cock-loving sissy slut. You’ve mastered stroking, kissing, licking, sucking, and worshipping your Mistress’ dildo, putting to good . . . → Read More: Sissy Essentials Continued: From Strap-On Sucking to Dildo Fucking