Learn to be a sissy.

Was there every any doubt? You spent years trying and failing to be a man and one afternoon as a sissy had felt more natural and right. You beam up at your mommy, feeling suddenly clear and confident, "I want to learn how to be the best sissy daughter ever for my Mommy and Daddy!"

Your mom smiles proudly as she hands you your outfit and as you slip it on you know you've made the right choice. The silk bright red thong hugs your sissy sack tightly and the string in back feels so snug and teasing against your tight little hole. The white stockings create a frustrating frisson as you slide them up your legs leaving you squirming sweetly. A padded bra gives you the illusion of tiny teen breasts and rub achingly against your swollen, puffy nipples. The skirt barely covers the top half of your ample ass and you can't help but imagine returning to school in this skirt and all the lustful stares, hungry hands, and hard cocks trying to get under your skirt. The top completes the look and as you stare at your reflection you wished you could see the schoolslut fucked by a dreamy Daddy dick. You know you'll be horny and needy every waking second in this outfit, and strangely, you're looking forward to it.

"Oopsie poopsie. We forgot the accessories!" Your mommy hands you a pair of Mary Jane school shoes and more importantly, a bright pink buttplug with a heart shaped base. You squeal with unabashed arousal as your mommy lifts your skirt, pulls down your panties and buries her face in your ass. You moan as she tongues your cunt ravenously, getting you wet and oh so willing to fit in your plastic plug.

"Mmm you have such a tasty cunt, sticky snacks. Now I'm going to push this pretty, plastic plug up your pert, puckered sissy hole, and it's going to feel so dreamy and creamy. But lesson one is, good sissies wait for permission to cum. So no matter how good it feels, don't cum or you'll fail before you get started."

You feel the tip of the plug pushing insistently against your ass. It tingles, tantalizingly, but you're sure you can hold out. The plug flares fatly as it forces inside you, the pain is so searing you feel like you might melt, and all your nerves burn brightly begging for the relief of blissful sticky squirts to drown out the flame. You are almost done, can you hold out? It would feel so good to give in and gush, but you so want to be a good sissy...