Sissy training

The question often is should a man need to go to sissy school for sissy training or are there other options?  As a hardcore femme sissy, I believe that sissy schools are one option for sissy training and may be the best option. That said there are many other options for sissy training that you can and should look into before choosing just one. One on one instruction from a mistress can be an effective way to learn about what is required to be a sissy and what a mistress requires in return. One on one instruction sissy training is the fastest way to get up to speed but it is also the most expensive way. One the other end of the spectrum there are many books that have be made about men that want to become sissies and this is by far the least expensive way to become knowable on the subject and to see if sissy training is something you really want to become involved with after all being a sissy is a lifestyle change and it is a big change at that. If you are reading this it is highly likely you have already made the decision to become a sissy and maybe you have known for years that it is your true identity, that’s great but you should spend time learning about what it takes to make the total transformation and how intense sissy training can be. Another option is trying different aspects of sissy training things like make-up work, male to female transformation clothing including the panty designs that change you from male to female, these styles are unbailable in the job they do to erase the male anatomy and change if to female. Chastity training is a big part of sissy training and something you can start right away but make sure to order a cage that is geared for a sissy. We will talk about many of these aspects of sissy training along with others but I think we will start at the area I personally know best which is male to female transformation for sissy training and how to femininize the genitals of men. Sissies should be training their penises to be as small as possible. There is a product called the Micro Penis Maker Sleeve that can take a small to normal sized penis and with sissy training change it to a real micro penis. I have personally seen a normal sized penis trained down to under 1”, it was actually very close to ½” in size what can be classified as a sissy clit. Before I go any further let me say that a sissy should always be completely shaved. Legs shaved, bikini area completely shave and there should be no hair what so ever on the penis, it should always be completely smooth. All hair on the butt including the anus should be completely shaved or you can have a full Brazilian wax which gets rid of the hair front and rear. Many that are in sissy training myself included have opted to have all the hair lasered away. This gets rid of it once and for all with very little regrowth. My very small penis is completely smooth and hairless which gets you ready for the next step and that is wearing male to female transformation panties and swimwear.

 Sissy training and wearing panties and swimwear that feminize you.

There is a world of change happening with male to female transformation swimwear and panties that give the wearer a realistic vagina. These styles were originally crated for men that are transitioning to female but have become extremely popular with other men/girls that are into the femme look including crossdressers, femme boys, sissies and both straight and gay men that have become interested in being in touch with their feminine selves. I will now show you why when it comes to sissy training why these have become the go to fashion for many sissies. First let me list a number of different designs that you can google to see what they look like: Koalaswim Clever Girl, Koalaswim Spicy Girl, Koalaswim Lady Gear Shorts, and Koalaswim Lady Girl Micro shorts. As you can see from the listing all the designs are from Koalaswim and the reason for that is they literally invented this category of clothing and they send their designs all over the world. I would love to see a bunch of sissies running around the beach wearing these very small bikinis and thongs which change their penis into a very real looking vagina, I get wet thinking about it! These designs work by forcing your flaccid shaft into your body and securely but comfortable keeping it there. This makes the shaft disappear! Then things get really interesting, the balls are split and kept in separate micro lip style pouches when the suit is in place you will have a vagina that your girlfriends will believe is real even if they touch it. It looks and feels real One of the more interesting aspects of how these designs work with sissy training is that after a while a very short while your brain see’s a vagina there and starts to change the thinking pattern and the way it views itself(you) as male of female. It turns out the brain is a very visual organ and will start sending feminine feelings when it no longer sees a penis and now sees a vagina. You brain starts to recognize you as female.

 I feel an additional aspect of sissy training should entail public work, that is being shown in public as a female and also being female in the most vulnerable positions one of which I believe is wearing almost nothing in public something like the male to female transformation suits we talked about above and forcing the sissy to wear them when she goes to the beach. This is some of the most intense but highly effective sissy training sessions one can experience.

More on this next post.

“The Sissy Mistress of Silverlake”

In a quiet, ivy-draped house nestled in the hills of Silverlake, Mistress Celeste built an empire—not of steel or glass, but of satin, lace, and submission.

She never set out to become a Mistress. At first, it was just a fascination. She was beautiful, sharp-tongued, and always in control. Men adored her, but they rarely satisfied her. That changed when she met Liam—her first real project.

Liam was a shy, tech entrepreneur in his thirties. Successful, handsome even, but nervous, always apologizing for his existence. Celeste saw through the stiff posture and expensive watch—he wanted to be told what to do. What to wear. Who to be.

One night, she slid a pink satin thong into his blazer pocket at dinner. No words. Just a look. He showed up at her place the next night wearing it—under his slacks. That’s when it began.

Celeste transformed Liam. His name became Lila. Weekly, he arrived to be waxed, tucked, painted, and perfected. She dressed him in ruffled panties, forced him to strut in towering heels, and trained him to serve tea like a delicate maid—while wearing a chastity cage and blushing the whole time.

Word spread in whispers through the darker corners of elite male circles. Powerful men—executives, attorneys, athletes—began contacting her. They all shared something: an aching need to surrender, to be feminized, to feel beautiful, pathetic, controlled.

Celeste started charging—high. Thousands per weekend. Her home became a discreet sanctuary where men could become sissies: Alexis, Bella, Gigi, Fiona, Crystal… Each had a custom routine. One learned to deep clean while wearing a French maid outfit and butt plug. Another was trained to pose for humiliating boudoir photos in sissy lingerie and post them (anonymously) online. Another learned how to twerk in a chastity cage until his makeup ran.

And they paid more for the humiliation. She made them curtsy for punishment. She made them compete—who could take the best strap-on session, who could deepthroat a training dildo better, who could walk a runway in 8-inch stilettos without falling. Each humiliation bound them to her tighter.

Mistress Celeste ruled without mercy—but with deep understanding. She knew this was more than fetish. This was transformation. Her clients didn't just want to be dominated—they needed to be rewritten.

Her favorite part? Watching the moment it clicked. The tearful gasp when a grown man saw himself in full sissy regalia for the first time—false lashes fluttering, lips glossy, bulge hidden, waist cinched. “Mistress,” they would whisper. “I think this is who I was always meant to be.”

And she would smile.

Because she already knew.

 “Becoming Bella” — A Steamy Sissy Training Session with Mistress Celeste

Bella had once been Brandon—an ex-Wall Street alpha who now knelt obediently on pink shag carpet, wearing nothing but a tiny lace thong, pastel garter belt, and his Mistress’s favorite collar. He wasn’t new to submission anymore. Mistress Celeste had been training him for six weeks, and tonight was his first graduation trial.

The room smelled like vanilla and dominance. Soft lighting reflected off full-length mirrors, making it impossible for Bella to avoid her own reflection. Her cock, locked tightly in a pink steel cage, throbbed with helpless excitement as she adjusted her glossy lips and practiced her curtsy in 6-inch pumps.

Mistress Celeste entered like a goddess of feminine power—wearing a black corset, thigh-high boots, and carrying the leather riding crop that had become Bella’s holy grail of both fear and desire.

“Look at you,” Celeste purred, circling Bella slowly. “You were a man once. Weren’t you?”

“Yes, Mistress,” Bella whispered, blushing furiously. Her voice was soft, trained—feminine.

“And now?” Mistress’s boot pressed gently under Bella’s chin, lifting it until their eyes met.

“I’m your sissy,” she whispered. “I belong to you.”

“Then show me.”

The next hour was a fever dream of lust, humiliation, and obedience. Mistress tied Bella into a heart-shaped spanking bench, legs spread wide by pink leather cuffs, butt cheeks exposed and twitching. One by one, she slid in her sissy training plugs—from the smallest to the one labeled “Princess”—moaning with approval at Bella’s gasps.

“You love how this stretches you, don’t you, slut?”

“Yes, Mistress! Please… more…”

Mistress laughed. “Good sissies beg.”

She made Bella strut in front of two mirrors, posture perfect, cage bulging obscenely through a sheer micro-panty. Bella danced, blew kisses at her reflection, and mouthed, I’m a sissy over and over. Each time she did it right, Mistress rewarded her—with a swat, with a plug twist, with whispered filth that made her knees tremble.

Then came the strapon.

Mistress Celeste lubed it slowly, provocatively, as Bella lay on her back, legs in the air, garters stretched tight and trembling. “Are you ready to be truly broken in, Bella?” she asked, running a manicured finger across Bella’s quivering lips.

Bella nodded desperately. “Please… I want to be yours. I want to be your favorite sissy.”

The strap-on slid inside slowly, relentlessly. Bella gasped, clutched the sheets, moaned like a girl in heat. Celeste didn’t let up. She pounded her sissy while tugging her hair, reminding her just how far she’d fallen—and how perfect she’d become.

“You’re not Brandon anymore,” she whispered into Bella’s ear as her hips drove in harder, “You’re mine. My trained, caged, fucked sissy doll.”

And Bella cried—tears of shame, joy, submission.

She didn’t want to be a man anymore.

She wanted to be this forever.