Sissy Chastity Training: The Ultimate Guide

Sissy Chastity Training: The Ultimate Guide

Get Access to the Hottest 18+ Sissy Assignments Around!

Personalized collection of assignments created just for you. Click below to start your journey!

Get Assignments for 2025

Sissy chastity training routine (by a Reddit user)

Wanted to share my daily sissy routine in case it inspires someone or anyone else wants to share 😊

Sissy dress time comes first, of course. After that:

1 hour – Sissy playtime and milking session. Anal stimulation with realistic cock dildo and (optional) vibe or prostate massager, while listening to cock worship or sissy hypno on headphones. I listen to the same one for a week, then switch to another.

45 min – Solicit men and mistresses to serve on various dating apps, Reddit, and other sites.

30 min – Anal stretching with large toys while listening to hardcore sissy brainwash and objectification hypno. Only recommended for a sissy who wants to ruin her boipussy.

10 min – Lying down, slowly play with a fat dildo while repeating my mantra out loud. No music or hypno. Then go another 10 minutes repeating my mantra silently.

My current mantra is: good – sissy – worship – cock

30 min – Shower and clean my sissyclit’s cage. Sissy humiliation hypno in the background.

45+ min (optional) – More soliciting for men throughout the rest of the night as time allows.

1-3 hours (optional) – Serve men, a group of men, or a mistress when a play date is scheduled.

Weekends: Same routine as above. At night, visit gay clubs and solicit my pussy as much as possible.

Like what you read, Sweetie?
Share with your friends 🎀

Twitter
Facebook
Reddit
WhatsApp
Tumblr

Get a FREE Sissy eBook!

Here’s your chance to claim one of our exclusive sissy eBooks—completely free! 

No strings attached, just pure sissy fun!

Ready to Be the Sissy You Dream About?

Safe. Discreet. Addictive. Everything you’ve been craving, in one girly little world.