Sissy mouths and asses were meant to be used, fucked, and filled. Strap-on training ensures that all of your holes are wide-open and ready for my strap-on dildo or a real cock!

My favorite job as a Sissy Trainer is taking a virgin boypussy and breaking it in — I’ll train you to take bigger and bigger toys in your holes, stretching them open. You aren’t a true sissy slut until your holes are capable of taking my ten-inch strap-on — then you can call yourself a real buttfuck slut!

If you’ve never had anything up your ass before, I’ll guide you through a training regimen of fingerfucking, small slender dildos, then on to larger hefty dildos, and work you on up to staying plugged with a big buttplug for several hours at a time, opening and widening your hole. If you have a webcam, I’ll watch and instruct during our phone sessions, giving you pointers on how to fuck your ass.

Your ass isn’t the only hole I’ll give a workout to — your mouth needs to be trained as well! My advice for sissy cocksuckers in training is to get a VERY realistic-looking dildo with a suction-cup base and stick it to a wall or full-length mirror. Kneel in front of it while stroking your sissy-clit and practice taking it all the way into your mouth, making sure to slide your lips over your teeth and swirl your tongue around to give maximum pleasure to the cock you’re worshipping. Read more about Sissy Cocksucker Training here!

Are you ready for some anal discipline with a real Sissy Trainer? I’ll open up your holes and give you the skills you need to be the sissy slut bottom you’ve always wanted to be!

Forced Feminization | Gay Sissy Conversion Therapy | Chastity and Orgasm Denial | French Maid Sissies | Lesbian Sissy Girlfriends | Pantyhose and Stocking Fetish | Sissy Strap-On Domination | Smoking Lessons and Smoking Femdom | Sissy Panty Slavery | Petticoat Punishment