Sissy Training Program: A Guide to Sex as a Sissy Girl

Now that you have accepted your sissy training program it’s time to think about ‘pleasure’. You will be allowed to orgasm, but you must do it as a girl. That will mean no direct contact with your little clitty. You will be taught to gain sexual pleasure by having your nipples stimulated and, yes, even through anal penetration.

Most Masters and Mistresses will want their sissies to have the right amount of stimulation. It will be carefully controlled during the sissy training program.

Sissy Chastity is a Must

You will need to wear a chastity device almost all the time. The reason for this is, as a sissy in training, you can’t be trusted. Your Master or Mistress does not want you touching yourself in a masculine way. They want to encourage female orgasms which requires a bit of reprogramming.

A chastity device is usually some form of cage that fits around your tiny wee-wee and is held in place with a lock. Your Master or Mistress will keep the key.

The sissy chastity device forms the bedrock on which you will be trained to experience orgasms and sexual pleasure in a more feminine way. For example, you may be asked to kneel in front of Mistress and play with your nipples through your silky bra and moan like a girl. As things advance, you may be expected to bob up and down on a vibrator, stimulating your prostate and bringing yourself to girl orgasm.

Girly Moans and Groans

Even if you are not feeling stimulated, as a sissy girl you need to moan and groan as if you are enjoying yourself. This can also act as additional reinforcement and is particularly important if your sissy training program dictates that you will eventually start servicing real men and pleasuring them.

Sissy Milking: What is It?

Many Masters and Mistresses will use a milking regimen to keep sissy under control. This will either be administered weekly or monthly. As a sissy, you will remain fully caged most of the time but this can be removed for the milking process.

It involves inserting something to stimulate the prostate gland leading to a deeper orgasm. This may be done several times in a short period to ensure that you become more compliant and learn to experience an orgasm in this way (through anal stimulation). Dominant partners use it primarily as a method of control and the chastity device can later be left on while you orgasm in a girly way.

Another option that can be added to this is collecting the semen from the sissy milking which you will then be forced to consume. You can also buy dildoes that can be filled with semen and ejaculated while you are sucking it.

Sissy nipple play can also be added to make the depth of the orgasm and its girlishness stronger.

Incorporating Nipple Play

Nipple play should be an essential part of the sissy training program. There’s nothing more delightful for a dominant partner than seeing their feminized other half playing with their nipples and moaning frantically.

The more you play with your nipples, the more sensitive they should become. Playing with them through a silky bra helps immensely and adds that feminine slant but you can also try these approaches to produce more stimulation:

• Gentle stimulation: Regularly massaging or gently brushing your nipples can help to increase blood flow and stimulate nerve endings, potentially leading to increased sensitivity.

• Temperature play: Experimenting with warm or cool compresses or even ice can help to increase blood flow and stimulate nerve endings.

• Essential oils: Some people find that applying diluted essential oils like peppermint or lavender can help to increase sensitivity. Always dilute essential oils properly and test them on a small area of skin first to avoid irritation.

• Nipple clamps: Some people find that using nipple clamps for brief periods can help to increase sensitivity over time. Start slowly and use them with caution to avoid injury.

Ideally, as a sissy, you should be playing with your nipples at least every evening, though edging and not orgasm. This builds a strong brain/pleasure connection. A Mistress may, for example, bring in a male friend to play with your nipples while you are dressed in sexy lingerie.

Penetrations and Toys

As well as nipple play, as a sissy you will need to learn to pleasure yourself anally. This applies even if you are not gay. As a sissy girl, you will need to learn how to stimulate your prostate and take a large cock to please your Master or Mistress.

For some, this is a prelude to penetration from a real man and is all about learning how to please. In addition, you will be instructed to practice sucking a cock while staring up at your Master or Mistress.

There's a wide variety of anal toys, each designed to provide unique sensations and experiences. Here are some common types:

• Butt Plugs: These are the most basic anal toy, usually shaped like a cone with a flared base to prevent it from getting lost inside. They come in various sizes, materials, and textures, and some even vibrate or have remote control functions. Butt plugs can provide a feeling of fullness, stimulate the anal muscles, and help prepare for anal sex.

• Anal Beads: These are a string of beads, with each bead gradually increasing in size. They are inserted one bead at a time, providing increasing levels of sensation and stretching for the sissy. Anal beads can be a good option for beginners or those looking to gradually increase their anal play experiences.

• Anal Vibrators: These combine the sensation of a butt plug with the added stimulation of vibration. They come in various shapes, sizes, and vibration patterns, and some even have remote control functions. Anal vibrators can provide intense pleasure and help to relax the anal muscles.

• Anal Dildos: These are specifically designed for anal penetration and typically have a flared base for safety. They come in various shapes, sizes, and textures, and some even have realistic features. Anal dildos can provide intense pleasure for sissies and allow for anal penetration.

• Prostate Massagers: Designed for people with prostates, these toys are curved to reach the prostate gland through the rectum. They often vibrate or have other features to stimulate the prostate, which can lead to intense pleasure and even orgasm.

• Anal Hooks: These are curved toys with a small hook at the end. They are inserted and then gently pulled out, providing unique sensations and stimulation. Anal hooks can be a more advanced toy and are not recommended for beginners.

When choosing anal toys, it's important to consider your experience level, preferences, and any potential sensitivities. It's also crucial to use water-based lubricants and prioritize hygiene to ensure a safe and pleasurable experience.

The Art of Pegging

Pegging is where your Mistress will penetrate you anally, usually with a dildo. This is an important part of the sissy training program because it is the ultimate humiliation. Mistress for a moment takes the role of a man and treats you like a slut. Maybe you’ll be wearing your pretty little maid’s outfit or perhaps Mistress will have you dressed in sexy lingerie – panties, bra, stockings and high heels.

Check out our post: Pegging Sissy: A Guide for Beginners

Learning How to Please a Man

If you are ultimately feminized and accept your role, you may progress to pleasuring a real man. Many men, particularly Alpha males, love to take a sissy. You will be expected to give oral relief at a moment's notice and accept his huge manhood like a real girl.

Much of the training beforehand leads up to this moment. Imagine, dressed in your finest lingerie, kneeling before a rugged man and pleasuring him with your mouth. You will groan with pleasure and stare up at him and then accept his hot juices when he is ready.

As a sissy, you will also be trained to pleasure women and provides an addition to your skills as a bimbo.

We’ll write more about this in due course, but, for now, enjoy your sissy training program and be a good girl!