The Complete Sissy Training Guide Part 2

In Part 1 of The Complete Sissy Training Guide, we covered the basics of sissification. Basic training is just that: sissy things that must be mastered that serve as a prerequisite for more advanced and sophisticated training.

Think of her as the soft, sparkling version of yourself that’s waiting to come out. She’s the girl inside who wants to feel beautiful, delicate, and desired. She’s playful, expressive, and full of personality. The more you get to know her, the easier it becomes to shape your training around who you truly are.

Every sissy has her own energy. Some are sweet and shy, others bold and bratty. Some adore frills and lace, while others love sleek elegance and quiet grace. There’s no right or wrong way to be feminine, only your way. What matters is that you start building a sense of self that feels authentic and exciting to step into.

Before we explore advanced sissification, take a little time to visualize your inner girl.
What does she wear? How does she speak? How does she carry herself when she feels most confident?

Because once you know her, everything else, the makeup, the training, the attitude, will fall beautifully into place.

Establishing Your Sissy Persona

From the moment you’re born, or shaped by the world around you, there’s a certain way society expects males to behave. They’re taught to dominate, achieve, and always prove they’re right. Quick judgments, impatience, and emotional distance often come naturally.

But you, sweet sissy, are different. Your heart leans toward kindness, your mind toward understanding. You listen deeply, respond thoughtfully, and approach life with a gentle grace that feels effortless. You don’t need to argue to be heard; you navigate situations with compromise and charm, letting peace and softness guide your actions.

Being a sissy means embracing your role as a giver rather than a taker. You don’t shy away from vulnerability, in fact, you welcome it. Asking for help when you need it isn’t weakness; it’s confidence in your connection with others, especially women. You understand that true strength lies in softness.

And yes, your sexuality flows in harmony with your nature. You are naturally receptive, enjoying pleasure in ways that honor your surrender. In this next phase of your sissy journey, we’ll focus on reprogramming your sexual responses and desires so that your sensual self aligns beautifully with your gentle, feminine heart.

In light of your evolving sexuality, this Part 2 of The Complete Sissy Training Guide will begin by focusing on reprogramming of your sexual responses and desires.

Sissy Desire – Sexual Reprogramming

To continue the sissification process, it is crucial to eliminate any remaining masculine desires from your mind. This can be achieved by regularly listening to sissy hypnosis files every day.

Sissy Hypno

If it were possible to bitch slap the male out of you, I would certainly do that. Instead we’ll focus on a tried-and-true form of sexual reprogramming, sissy hypnotic files. You’re already familiar with them from Part 1 of this sissy training series.

Sissy hypnosis isn’t just about looking feminine, it’s about feeling it deep inside. Through guided hypnosis, you begin to quiet the masculine habits that once defined you and open yourself to softness, grace, and surrender. The more you listen and let go, the easier it becomes to move, speak, and think like the woman you’ve always imagined within.

Over time, your confidence shifts. You stop performing femininity and start living it, not as an act, but as a natural expression of who you are. The suggestions in these hypnotic sessions help retrain your thoughts, dissolve resistance, and awaken a calm, feminine presence that feels authentic, comforting, and beautifully aligned with your desires.

Sissy hypnosis, when practiced with care and intention, becomes more than a fantasy. It’s a personal re‑coding, a gentle rewriting of the mind that lets you experience femininity as both a mindset and a source of joy.

✨ Try This: SissyHypnox.com offers a 60-day program to guide your full feminization journey and help you unlock deep confidence and expression.

The next step will be to…

Learn to Pleasure and Release Like a Girl

Discovering how to connect with your feminine energy is a journey of softness, patience, and deep self‑awareness. Instead of rushing toward release or intensity, feminine pleasure flows from calm confidence and emotional openness. It’s not about performing, it’s about feeling.

When you approach your body with care and curiosity, you start to notice the subtle ways your energy builds, shifts, and expands. This isn’t a race or a goal, it’s an exploration of what makes you feel beautiful and alive. Feminine sensuality grows stronger when you relax, breathe, and allow yourself to feel every moment.

Training yourself to embody that energy begins in the mind. It’s about letting go of control, slowing your rhythm, and embracing a softer presence. The more you practice patience and emotional connection with yourself, the more naturally your feminine side begins to shine through every part of you.

Here’s the setup:

• Give yourself a 30 minute block of time
• Always wear at least a bra, panties and heels
• Always have something in your pussy (from this point forward it’s imperative to associate sexual pleasure with anal stimulation)
• Tuck your clitty downwards into your panties
• Listen to sissy hypno or watch an erotic YouTube video
• Nub the tip of your clitty with one finger only
• With your other hand you can play with your nipples or sensually rub/caress your body
• As you become more aroused, moan like a sissy slut
• If your clitty gets hard, stop nubbing until you become soft
• Don’t become attached to any specific outcome, just focus on experiencing feminine pleasure
• If you do happen to release, that’s nice. If you don’t, that’s fine too

Once you experience sexual stimulation, if not satisfaction, in this way several times, you will gradually lose the desire to orgasm in a crude, manly-like fashion. It’s just not lady-like. Eventually you will train your clitty to remain limp throughout, even while climaxing.

Sexual Denial

Most men rush toward pleasure, chasing quick satisfaction and missing the deeper emotions hidden behind desire. It can leave them restless, always craving more yet never truly fulfilled.

A sissy’s journey feels different. Her path is slower, softer, more deliberate. She learns to live in a constant shimmer of longing, feeling her femininity rise every time she resists the urge for release. That gentle ache reminds her who she’s becoming, a patient, graceful, and attentive version of herself.

Each moment of restraint becomes a little act of devotion. Instead of chasing instant pleasure, she lets her focus drift to the small joys, lip gloss shining in the mirror, silky lingerie brushing her skin, the quiet pride in her own self-control.

Many sissies eventually choose a form of gentle physical reminder, like a chastity device, to help them stay faithful to their training. With the right fit and guidance, it becomes less of a cage and more of a commitment, a daily symbol of feminine discipline and surrender.

If you’re exploring that step, start by learning how sizing works so it feels safe and comfortable. Understanding your body’s needs makes the experience empowering, not restrictive. Think of it as preparing yourself for a deeper, more mindful kind of pleasure, one that blooms through patience and surrender.

Sissy Chastity Dice Game

Sometimes a little unpredictability makes your chastity journey even more exciting. Imagine handing over control, smiling nervously as your keyholder picks up two dice, one black, one white. The soft clatter of the roll becomes the sound of fate deciding how long you’ll stay locked. It’s simple, yet the thrill runs deep, doesn’t it?

What makes this so fun is the mix of surrender and chance. You don’t know whether you’re getting a short tease or a long stretch of denial, and that uncertainty is what fuels the erotic tension. It becomes less about control and more about anticipation.

If you want to try it, you can find the full rules in 7 Fun Sissy Chastity Games, where I explain exactly how the dice decide your lock-up time and how to make the experience even more playful and personal. It’s the perfect way to blend discipline with delight.

Attempt an Anal Orgasm aka Sissygasm

For those on the path of total sissy sexual reprogramming, reaching the point where you can experience pleasure exclusively through anal stimulation is a truly transformative milestone. This is what we lovingly call a sissygasm, and it’s not just about the physical sensation, it’s about embracing a fully feminized way of experiencing sexuality. Your clitty may still exist as a reminder of your old self, but it becomes a delicate, almost ornamental organ, only showing life when arousal calls, and never taking the lead again.

Getting here takes patience and practice, but once your body learns, the result is an intense, leg-quaking release that makes old masculine orgasms feel like a distant memory. It’s not just pleasure, it’s a celebration of surrender and feminine identity, a reminder of how beautifully your mind, body, and desires have aligned.

Sissygasms aren’t just a milestone, they’re proof that your training has unlocked a whole new, intoxicating way to experience yourself, fully feminine and fully yours.

Your Sissy Slut Factor

Many people confuse crossdressers and sissies, but the distinction really comes down to submission. As a crossdresser, you may simply enjoy expressing your feminine side through clothes, makeup, or behavior. A sissy, however, embraces a deeper level of submission, actively seeking to serve and please dominant individuals of any gender or orientation. This isn’t just about outward appearances, there’s a psychological and emotional layer to the surrender that makes sissies uniquely devoted.

Part of what defines sissy submission is the willingness to embrace your role fully, including sexual receptivity. Even if your attractions don’t align with traditional expectations, part of the sissy journey is accepting and enjoying being penetrated rather than taking on an active sexual role. It’s an empowering form of surrender that can heighten your sense of femininity, intimacy, and connection in ways that go beyond just wearing a pretty dress or applying makeup.

Being a sissy is about celebrating every aspect of your feminine identity, including your willingness to give up control, explore vulnerability, and find pleasure in the act of serving and being penetrated. This kind of submission isn’t just sexual, it’s deeply transformative, allowing you to fully inhabit your feminine self while strengthening your connection to those who dominate you.

Sissy Chastity

If you’ve already explored the art of gentle self‑pleasure and learned to connect with your body in softer, more feminine ways, you’ve probably felt that inner spark that comes with surrender. That’s just the beginning, sweetheart. There’s a deeper level of devotion waiting for you, one that’s all about patience, restraint, and control.

True feminine transformation often blossoms when you learn to quiet old habits and let discipline shape your desires. For many sissies, this means embracing a form of self‑denial that helps refocus energy away from instant pleasure and toward lasting growth. It’s not about punishment, it’s about purpose, choosing to prioritize your feminine evolution over quick release.

When you commit to restraint, you begin to experience yourself differently. Your energy builds, your focus sharpens, and your sense of identity grows stronger. You start to understand that femininity isn’t just about how you look, it’s about how you feel, graceful, intentional, and beautifully in control of yourself.

Learning to redirect your desire can be deeply empowering. It turns temptation into motivation and discipline into devotion. As your journey continues, remember this: every act of restraint is an act of love toward your own transformation.

You’re not losing anything, darling, you’re reclaiming the part of you that’s meant to shine.

Dildo Training

Hopefully, you have accepted the fact that your pleasure will now come from anal stimulation only. It’s time to purchase a dildo for yourself, if you don’t already have one. It should be the perfect size for you – not too big or small – just enough to provide some initial discomfort.

But don’t worry, you’ll get used to it soon enough. Part of sissy training involves expanding and stretching out your tight sissy ass.

Practicing Blowjobs in the Shower

Many dildos come with a suction cup at the base so you can practice riding it while it’s secured to the floor. This works even better in the shower as the wet environment will make the dildo stick really well, to the shower floor; or to the wall.

Stick it to the wall, soap it up, bend over and let it slide right in. Then turn around, get on your knees and practice being the sissy slut that you are rapidly becoming.

Caged and Plugged While Fondling Your Body

If you wanna feel super slutty, lie down on the bed and stick the dildo up your pussy. Pull on a pair of panties over your chastity cage and fondle your titties while fantasizing about being fucked silly.

Create that scenario enough times and you’ll be compelled to go out and find yourself the real thing. Once you do that, you are a bona-fide, card-carrying sissy slut.

Watch Videos of Your Favorite Fantasy

Every sissy has that one fantasy that just makes their heart flutter and their body tingle. Maybe it’s the idea of surrender, or simply watching someone embody the confidence and grace you crave. Whatever it is, there’s no shame in letting your imagination explore it.

Watching a video that captures your favorite fantasy can be a sweet reminder of who you want to become. Notice how it makes you feel, the way your breath changes, the spark in your eyes, the little ache of desire mixed with curiosity. That’s your feminine energy waking up, asking to be seen.

Instead of rushing through it, let yourself soak in the mood and the beauty of what you see. Ask yourself, What draws me in? What does this awaken in me? It’s not about copying someone else, it’s about discovering your own rhythm of sensuality.

Every time you tune in with intention, you’re not just watching, you’re learning how to express your softness, confidence, and surrender in a way that feels real to you.

Sissy Training Guide – The Humiliation Factor

Knowing that your caged clitty will be slowly shrinking in size because of non-use should put you in a humiliated state of being. That’s exactly the place where you want to be… sissified, emasculated and humiliated.

Sexual humiliation is an indescribably erotic feeling. That’s one of the perks of being a sissy. You want to begin looking for ways to purposely place yourself in humbling and demeaning situations. Here are a few ideas:

• Walk up to a makeup counter and ask the sales girl what type of foundation would be appropriate for your skin tone
• Make an appointment with a salon to have your toenails manicured and polished
• Go to a department store (in male mode) and purposely browse through the lingerie section
• Wear high-waisted panties that not-so-subtly show above your jeans
• Have your belly-button pierced

By practicing putting yourself in embarrassing situations, you will become addicted to feeling that erotic rush that a humiliated sissy craves.

Dollification – Beautification

Every sissy dreams of becoming irresistibly pretty, that kind of beauty that turns heads and melts hearts. Dollification is your path to that transformation, where every touch of gloss, every flutter of your lashes, and every delicate detail brings you closer to your most enchanting self. It’s not just about painting a perfect face, it’s about learning the art of presence, poise, and feminine allure.

Women spend hours perfecting their look because they understand that beauty is both ritual and expression. For you, it’s even more meaningful. Each brush stroke and lipstick glide is a small act of devotion to your feminine side. You might not mirror every detail of a natural-born woman, but you can absolutely glow with a polished, confident, doll-like beauty that radiates effort and care.

And here’s your secret advantage, many women take their femininity for granted. They skip the polish, the softness, the magic. You, my dear, won’t. You’ll embrace every detail, from smooth skin and glossy lips to graceful posture and perfect presentation.

Through dollification, you don’t just look feminine, you become feminine, body and spirit. Each beauty ritual shapes not just your appearance, but your mindset too, turning everyday self-care into a deeper journey of transformation.

Hair Removal

Smooth, soft skin is such a beautiful part of feeling feminine, isn’t it? There’s honestly no reason for any seriously minded sissy or feminine soul to keep all that body hair. It hides your glow and makes you feel less like the gentle, polished version of yourself you’re becoming. These days, plenty of men shave their bodies, so you don’t even need to worry about it being unusual.

Think of hair removal as one of your little beauty rituals, not a chore. It’s your time to connect with your body, to nurture it, to make it feel delicate and loved. A clean shave once a week, at the very least, keeps your skin silky and your confidence higher. When that razor glides and the last bit of roughness disappears, you’ll notice how much more feminine your body feels in soft fabrics and lingerie.

Start small if you need to, but once you feel that smoothness, you’ll never want to go back. It’s one of the simplest, most powerful ways to express your femininity and self-care.

If you’re ready to perfect your shaving routine, check out this helpful article on Sissy Shaving Tips — it’ll guide you through every sweet step toward softer, prettier skin.

Makeup Magic for Your Sissy Glow

Makeup isn’t just powder and paint, it’s your soft armor, your self-expression, and the sweetest little signature of your feminine side. The real magic isn’t about hiding who you are, it’s about showing her off. But for your look to shine, you need two things: caring for your skin and practicing a few smart techniques.

One of the very first steps, as we always share inside SissyHive’s “Best Makeup for Sissies” guide, is to treat your skin like the precious canvas it is. That means gentle cleansing, a light moisturizer, and a little patience before any color touches your face. A fresh, smooth base is what makes the difference between “that’s cute” and “oh my god, who is she?”

Once your canvas is ready, build yourself a small but powerful starter kit:

• A liquid foundation that melts seamlessly into your jawline
• Concealer to soften any shadows (especially those tricky beard areas)
• A soft pink blush and a simple, neutral eyeshadow palette
• Mascara to open your eyes, a brow pencil for framing, and a flattering lip shade that feels natural yet feminine
• A setting spray to lock it all in and keep your glow steady through the day

The secret? Soft blending. Correcting shadows instead of piling on layers. Keeping your lips smooth and kissable rather than harsh or overdone, unless your style calls for a bold pop of color.(sissyhive.com)

So here’s your sweet little ritual, step by step:

1. Cleanse and moisturize
2. Smooth on a primer
3. Layer foundation and concealer
4. Add gentle contour, blush, and highlight
5. Define brows, soften eyes, shape lips
6. Mist with setting spray
7. Slip a few touch-up tools in your bag

At first, your hands may feel clumsy, your brush strokes a little shaky. That’s okay. Every time you sit down at the mirror, you’re not just practicing makeup, you’re practicing becoming her. And with each stroke, each little mistake, each moment of confidence, you’ll glow brighter as the sissy you are meant to be.

Wigs

Not every sissy is blessed with long, luscious hair, and that’s okay. Wigs are your secret weapon, and the good news is, there are tons of inexpensive synthetic wigs that look absolutely fabulous once you learn how to handle them.

Here’s the truth: the wig you order online may not look exactly like the glamorous photo you saw on the model. Sometimes they’re ready-to-wear straight out of the box, but other times they’ll need a little love, like trimming bangs, brushing them out, or giving them a gentle style.

In the beginning, I always recommend going for a low-maintenance wig. Something simple, feminine, and easy to slip on without a ton of fuss. Hair styling is a whole skill set of its own, and while it can be so much fun to explore later, you don’t need to overwhelm yourself when you’re just starting your sissy journey.

Over time, you can experiment with cutting, heat-styling, and even trying different lengths and colors. But for now, think of your wig as a crown, easy, pretty, and confidence-boosting, so you can focus your energy on practicing your makeup and learning to glow in your femininity.

Nails

In the world of masculine habits, nail care is something most men barely think about. But for us girls on the sissy path, neat and pretty nails are one of those small details that make a huge difference. Well-groomed hands instantly soften your look and add to your femininity.

The best part is, you don’t need to run to a salon to feel polished. A simple at-home routine can transform your nails: file them into a soft oval or rounded shape, smooth away any rough edges, and finish with a clear or matte polish. That tiny layer of shine makes your fingers look delicate and cared for.

There’s also a practical side. Smooth, shaped nails mean no more snagging your nylons or scratching your freshly shaved legs. It’s self-care with a purpose, and every time you glance at your hands, you’ll feel that little thrill of being more put-together, more girly, more you.

Makeover Time

Sometimes, as a sissy, it’s hard to imagine just how gorgeous your dollified self can become. When you’re still learning makeup, your reflection may not yet match the dreamy vision you hold inside. That’s perfectly normal, but it can also feel discouraging.

One of the best confidence boosts you can give yourself is booking a professional makeover. Many makeup counters or cosmetics stores even offer free sessions with skilled artists. Sitting in that chair and watching your face transform is such a magical moment—it shows you the potential waiting beneath your practice.

When I had my first makeover, it lit a fire inside me. Suddenly, I knew exactly what was possible once I mastered the brushes and colors myself. That inspiration is priceless, and it can keep you motivated through the learning curve.

Think of it this way: a professional makeover is a sneak peek of the girl you’re becoming. And once you’ve seen her, you’ll never stop chasing that glow.

Developing Your Sissy Body

After playing with makeup, the next step that really transforms your sissification journey is shaping your body into a slim and feminine one. Sweetheart, you should absolutely aspire to becoming that skinny, soft sissy you dream of.

Why a Slim, Feminine Shape Matters

When your body becomes slender and graceful, your whole presentation shifts. Dresses hug your curves instead of hiding them, and the confidence that radiates from that makes you glow in every room you walk into. Being slender also makes it easier to pass in public, slip into sexier, form-fitting outfits, and enjoy all the sweet attention that comes your way. Plus, there’s a huge bonus, you’ll look younger, feel lighter, and your health will thank you for years to come.

Skinny Sissy Diet

Darling, let’s be real for a moment. Diet is everything. When I worked as a personal trainer, I learned that weight loss is about 80 percent what you eat, and only 20 percent movement. That means the kitchen is your playground.

Most of us were raised on what I lovingly call crummy carbs. These are breads, pastas, chips, and sugary treats that don’t serve your feminine goals. The magic trick is simple: start replacing those with fruits and vegetables. When you feed your body with clean, colorful foods, the fat melts away and your skin glows like never before.

If you need structure, check out the guides and assignments on SissyAssignments.com, they’re designed to keep you motivated with fun little challenges that push you closer to your feminine ideal every single day.

Booty Workout

Of course, being slim is only half the story. A sexy, round, lifted booty is what gives your figure that jaw-dropping wow factor. When you slip into panties, leggings, or a tiny skirt, you want that butt to pop, don’t you?

The secret is in consistent glute workouts. Squats, hip thrusts, donkey kicks, and bridges, they may sound basic, but when done with intention, they reshape your rear into something deliciously round. If you need help staying disciplined, give yourself playful booty day assignments. It makes training so much more fun when you treat it like a game.

Sissy Waist Training

To tie it all together, every sissy dreams of that hourglass silhouette, where your slim waist cinches in and your hips and booty bloom out. A balanced diet will slim you down naturally, but to really accelerate your transformation, corset or waist training can help.

I still remember the first time I laced myself into a corset. It was tight, yes, but the moment I looked in the mirror, I nearly cried. I finally saw a reflection that matched the girl I’d always felt inside. A good corset not only reshapes your body, it reshapes how you feel in your own skin.

FAQs

1. What is sissy sexual reprogramming?
   A focused routine (hypnosis, mindset drills, disciplined pleasure) that shifts arousal patterns toward feminine, receptive experiences while prioritizing consent and safety.
2. How often should I listen to sissy hypno?
   Start with 15–30 minutes daily for 30–60 days; keep a journal to track triggers, mood, and progress.
3. Is chastity safe for beginners?
   Yes, with correct sizing, hygiene, short trial windows, and breaks. Begin with 1–3 hour sessions before overnight.
4. How do I practice for a sissygasm?
   Use breathing, edging without penile focus, anal training with lube, and pelvic floor relaxation; reduce visual overstimulation.
5. What makeup helps with beard shadow?
   Orange/peach corrector under foundation, soft blending, and setting; see our Makeup Guide for exact steps.
6. Are humiliation tasks required?
   No. They’re optional role-play. Keep everything ethical, legal, and consensual, choose softer tasks if anxious.
7. What’s a beginner wig I won’t ruin?
   Heat-resistant synthetic, mid-length, lace-front with a neutral color; learn detangling and parting before heat styling.
8. Do I need a corset for waist training?
   It helps visual feedback and posture, but nutrition and glute/waist workouts matter more for lasting shape.

Are You Ready for Part 3 of our Sissy Training Guide?

Part 1 of The Complete Sissy Training Guide covered the nuts-and-bolts of the sissification process. It’s meant to serve as a primer on how to train a sissy.

This Part 2 took things to a deeper, more intense level. We went over:

• Establishing Your Sissy Persona
• Sissy Desire – Sexual Reprogramming
• Your Sissy Slut Factor
• Dollification – Beautification
• Developing Your Sissy Body

Part 3 will take the sissification process to new, and even scarier, levels.

In Sissy Training Guide Part 3, we’ll be discussing:

• Voice Feminization
• Socialization
• Transition Education
• Total Transformation

Are you ready for that princess?