If you’re in a D/S relationship where the female is dominant and the male is submissive, you might have thought about incorporating sissy training into your sessions. Sissy training can be a fun and satisfying experience for both parties, but before you get started, it’s best to understand why you’re considering training (or being) a sissy, what roles each partner should play in sissification, and how to get the most out of your journey. To that end, this guide details everything you need to know about sissy training, plus provides resources for additional exploration.
What is Sissy Training?
First, let’s start by defining a “sissy.” A sissy is a man who is (consensually) “forced” to adopt feminine appearances and behaviors. Sissy training, then, is the process by which the dominant partner gradually trains the submissive partner to become more feminine.
Why do people get off on being or training a sissy? There can be various reasons. Some of the most common include:
- A male sub who fantasizes about being a woman
- A form of dominance or control over the sub
- A form of obedience, punishment, or humiliation
- A psychological break from the pressures of being a male
- A form of self-exploration, self-acceptance, or self-expression
Note that sissy training differs from crossdressing in that there must be an element of dominance and submission. In other words, crossdressers dress like women because they want to and of their own accord. Sissies dress and behave like women because their dominant partner tells them to (whether they want to or not, which of course depends on the dynamics of your BDSM relationship).
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Sissy Training Guide
Whether you’re the mistress or the sissy-to-be, sissy training involves four types of modifications and activities:
- Identity
- Appearance
- Behavior and mannerisms
- Tasks, both sexual and nonsexual
Let’s explore each.
1. Identity
The male needs a sissy identity that’s separate and distinctly different from his own persona. Some ways to establish a sissy identity include:
- A female name
- A feminine email address
- Social media profiles based on the sissy persona
- A female-based backstory, which might include anything from movie and music preferences to imaginary relationships and experiences to favorite brands, foods, books, and hobbies
Related: 25 punishment ideas for subs and when to use them
2. Appearance
Perhaps the most marked change, at least at first, is in the sissy’s appearance. A man can change their appearance to become more feminine by:
- Growing his hair long and adopting a female hairstyle
- Shaving his chest, legs, and armpits
- Wearing makeup such as mascara, eyeliner, eye shadow, and lipstick
- Getting his ears pierced and wearing jewelry such as earrings, necklaces, rings, and bracelets
- Wearing panties and a bra
- Tucking his penis between his legs
- Wearing a chastity device, especially one designed to resemble a vagina or “clitty”
- Wearing female clothing: high heels, dresses, skirts, and other women’s apparel – even a maid outfit, especially for roleplaying sessions
- Wearing a penis shrinking sleeve
- Painting his nails (fingers and toes)
Related: 10 best chastity games to play with your partner
3. Behavior
Once a sissy persona is established and the male looks like a woman, the next step is to have him adopt feminine behaviors and mannerisms. Examples include:
- Adjusting his voice to a higher pitch to sound more feminine
- Adopting female postures, such as swaying his hips when he walks and sitting cross-legged
- Peeing sitting down
- Using feminine products, especially if colored pink
- Pursuing feminine interests and hobbies
- Checking out other guys with his femdom
- Watching porn made for women
- Adopting traditional female gender roles in the home
Related: Where to buy chastity panties
4. Tasks and Activities
Finally, sissy training often involves having the man complete tasks or engage in activities. These tasks can be used to reinforce his feminization or as a form of obedience. The male can be punished or rewarded depending on how well he completes the assigned tasks. Some might include sissy training equipment, which is basically another term for the clothes, toys, makeup, and other items used to train a sissy. Ideas include:
- Role playing, where the man acts as a woman in certain situations defined by his domme
- Wearing a butt plug for anal training
- Anal training by pegging with a dildo or strapon to simulate anal sex or to achieve an anal/prostate orgasm
- Wearing a chastity cage full-time so his penis is no longer a factor
- Sissy hypnosis (search online resources for recordings)
- Cum eating, where the sissy eats his own (or another man’s) cum
- Shopping trips, where the sissy buys new outfits or other feminine products
- Cuckolding, where the sissy watches his domme have sex with another man
- Giving a blowjob to another man while his mistress watches
- Participating in online communities as his sissy persona
Related: 21 femdom humiliation ideas
Exactly how you implement sissy training, and in what order, is ultimately up to you – and you don’t need to adopt or perform anything you’re not comfortable with.
Sissy Training Tips
Follow these tips to make your sissy training experience enjoyable for all parties.
1. Communicate
The most important part of sissy training is to communicate at the beginning, before you put on the first pair of panties. It’s important to define exactly what both parties want to get out of it and to set (and understand) limits to keep the experience fun and safe.
Related: Top fetish tests to discover your kinks
2. Give Assignments
Dommes can give their sissies daily or weekly assignments, exercises, or rituals they must complete. It’s a good idea to start slow and gradually progress to sissification. For example, you might start by wearing panties, then move on to applying makeup. Baby steps can keep things fun and interesting without becoming overwhelming.
Related: The ultimate guide to long-term and permanent chastity
3. Keep a Journal and Check In Regularly
It can be a good idea to have the sissy keep a journal so they can explore their emotions, thoughts, and feelings during the sissification experience. The domme should also check in with the sissy regularly to ensure he is enjoying the experience. It’s entirely possible for feelings of embarrassment, shame, or even guilt to creep in; if they do, be sure to address them immediately, and if it’s too much, press pause on becoming a sissy.
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4. Practice Positive Reinforcement
While it’s true that sissification can be a form of humiliation or punishment, positive reinforcement can go a long way toward keeping both partners satisfied, safe, and healthy. Reward and praise sissies who successfully complete tasks or modify their personas, behaviors, and appearance. Make sure both partners are on the same page in terms of expectations, and the sissification process will be better for everyone.
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5. Take Advantage of Sissy Training Resources
There are plenty of sissification resources on the web, from sissy training schools, blogs, and social groups to sissy clothing, chastity cages, and other equipment. Examples include:
Above all, sissy training should be a fun and enjoyable experience. Follow these tips to make sure both partners have a great time and get the fulfillment they’re seeking!
