You have an effeminate boyfriend even or submissive husband and discover that you really want a gurl. So it’s up to you to train your sissy to please you.
The first and most obvious thing to do is to require that she start wearing female underwear. There is something very sexy about pulling on female underwear as a sissy. It’s a really good place to start. It’s also a good idea at the same time to begin some form of anal training. To do so, you can start with a series of extended trials of butt plug insertion. On a gradient, your sissy can train her ass with a bigger and bigger plug, with longer and longer sessions of being plugged. You want her to get present to the idea that her ass is yours to use.
It’s a very good idea to train your sissy to wear stockings with a garter belt, and high heels and perhaps a skirt along with her frilly lady’s underwear for public showings. This will really put her in the correct frame of mind to be your service sissy.
Obviously, the main thing to focus on in training your sissy is to train her to wear a cock cage. If you think of her ass as her “man-pussy” and her cock as her “over developed clit”, then it becomes easier to help progress her sissyfication to full Gurliness.
Next, you need to begin to teach your sissy how to properly use makeup to make sure she is beautiful for you. And of course, she will need a pretty pink wig to complete the ensemble.
Imagine her in an outfit with her pink hair, all made up with her short skirt, garter belt, nylons and high heels and her cock cage peeking out of her frilly lingerie. How cute!
It’s a good idea to have your sissy in a collar and leash when you have guests so she on display as “owned” when she serves you. She can serve you and your friends drinks and hors d’oeuvres while dressed as your personal French maid to make everybody’s evening fun. And of course, you can use her and share her with your friends if that is what is desired. She can fluff your girlfriends, get paddled by them and even pegged by them if you desire.
Ultimately, while denial is a good teacher and while milking your sissy into a cocktail glass for her to drink every so often is a fun creative way to give her a release, you really want to train your sissy to be your pegging bitch. Training her to be pegged should begin with a one finger prostate massage and progress from there. You should train your sissy to take thicker and thicker and longer dildos with the goal of eventually using a strap on to fuck your sissy’s ass. Over time, bigger cocks and even fisting her ass is a possibility. It’s all a matter of training. Remember, your sissy is there to please you.
It’s fine to restrict your sissy to clean up duty, so she can eat out your cum filled pussy or ass, and its also fine to teach your sissy how to properly pleasure you orally so that if you feel like having an orgasm she can oblige. It’s also completely on the cards to train your sissy to fluff or clean your male partners or Bulls. I have known women to require their sissy to be a fuck toy for their Bulls too. It’s all up to you.
It’s a good idea accustom your sissy be paddled. The use of a paddle or a hairbrush on your sissy is a particularly good way to discipline her, and we all know that she will need to be disciplined occasionally. She should know that when you give her a good over the knee paddling, you do so because you are training her, not just to be cruel. It’s never a good idea to paddle out of anger. Training your sissy to be your good gurl is a time-honored process where care and nurturing of her is important. She thrives on humiliation and it’s your job as her mistress to bring her along so that she is well trained to please you the way you desire.
The good news is that there are innumerable cis men out there looking for a Mistress to serve. If you want a sissy, she is there for the taking.
Like with any kink, sissyfication requires communication. Many sissies do not really know all that there is to be gained by being feminized, and they often do not expect to have the strong positive reaction to being feminized that they do. They find that they really come to love the experience, and many go on to contemplate extreme measures, like castration, to fulfil on their duty to their Mistress. The thing is that sissyfication is and feminization is not the same thing as transformation. A trans girl is not feminizing because they are being trained as a sissy, they are feminizing because they are indeed a female inside. Feminization and sissyfication are aspects of humiliation of a cis male that your sissy thrives on.
A good way to approach the process of sissyfication is to work on “brainwashing” your sissy. Hypnosis is a useful tool in this approach. I recommend The Brainwshing Book: Hypnotic, Erotic Behaviorism and Beyond by Sleepinggirl, who both practices hypnokink personally and she also teaches hypnokink workshops.
“Brainwashing” is a concept that titillates and mystifies—it implies an intense kind of control over another person and surrender of will. Within the context of erotic hypnosis, it might be considered a sort of holy grail to some, but what does it mean to achieve this in an ethical, effective, and mutually enjoyable way? In “The Brainwashing Book,” she explores a model that teaches and takes advantage of well-researched psychological principles and intermediate-to-advanced hypnosis skills in order to pursue this fun, hot form of play—and find how it can improve your trancing as a whole. Sleepingirl is a queer writer, presenter, and podcaster with a decade of real-life erotic hypnosis experience on both sides of the “pocket watch.”
So armed with a cock cage, a series of butt plugs, a strap on and several didlos, a collar and leash, and a good paddle, your sissy can be trained to experience herself as a gurl designed to perfectly please you. She will need her ladies underwear, her garter belt and stockings, high heels and a short skirt along with a wig and make up. And of course, the most important consideration, a good attitude. She needs to buy in completely.
In many cases, it’s a good idea to train your sissy to serve you and your friends. She can present herself in her pretty outfit and make sure you and your girlfriends have drinks and snacks and she can serve to pleasure your girlfriends by letting herself be used by them as a fuck toy. This would be a very humiliating services and one to aspire to rather than one to start out with. I have learned of sissy’s who are well trained to be toilet submissives for their Mistresses. So the sky is the limit. If you can think of it, you can train your sissy to execute.
It is important to emphasize that training a sissy is about enrolling them in the process and bringing them along on a gradient that allows them time to adjust to the concept and context. Communication is key. Negotiations must be frank and its important to make progress with each transition with the sissy buying in completely. This may take some time, but its worth it in the end. The folks we have talked to who are involved in FLR dynamics who are pursuing sissyfication are among the happiest kinksters we have ever encountered. Living your true self expression as a kinkster is really powerful.
We have found that those submissive kinksters who know what they genuinely want and who they truly are experience the process of sissyfication with an open heart.
Ultimately its up to you to be responsible for leading the communication to make sure you train your sissy well. If you need coaching to help you train your sissy, then feel free to reach out to us to ask us how to begin.
On our pod, The Kinky Coctail Hour, we had a conversation with a sissy that is worth a listen https://www.buzzsprout.com/962578/8440166
SafferMaster and Lady Petra offer Kink Relationship Coaching with online, group, and personal coaching options.
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Lady Petra and SafferMaster also produce the Kinky cocktail Hour podcast available on all podcast platforms and here: https://kinkycocktailhour.buzzsprout.com/