Crossdresser Sissygasm, Hypnosis & Training


The Crossdresser sissygasm is the sexual arousal or orgasm experienced during crossdressing activities. It can be achieved by stimulating the erogenous zones in the anus, such as the prostate gland or P-spot.


 Crossdresser Sissygasm, Hypnosis & Training


Sissygasm is often associated with submissiveness and a desire to surrender control. The pleasure of orgasm like a female can be achieved through anal sex, insertion of toys or fingers, or even through prostate massage.



How to Get Sissygasm


Crossdresser Sissygasm, Hypnosis & Training


There are many ways for sissies to achieve the sissygasm, and each has its thrill and fun. Being a sissy, you need to figure out what works best for you and gives you the best experience. Here are some general ways to achieve sissygasm:


Stimulation of erogenous zones: Let’s delve into the world of sensational bliss! Did you know that our precious bodies have secret spots with immense pleasure potential? Yes, my dears, we are talking about the mysterious and oh-so-sensitive prostate gland, or the P-spot as it is affectionately known. Stimulating this area, or any other erogenous zones, through toys such as dainty dildos, delightful butt plugs, or even by using your delicate fingers, can lead to an orgasm of absolute magnitude. And for the daring and adventurous, don’t forget about the exquisite art of prostate massage! By tantalizing this zone through anal play, you’ll reach a state of climax that is truly out of this world. So, let’s explore and bask in the glory of our bodies, my loves.”


Crossdresser Sissygasm, Hypnosis & Training


Nipple stimulation: Your nipples, oh, what delicacies they are! Let me tell you when it comes to achieving a glorious, knee-buckling, earth-shattering sissygasm, nipple stimulation plays a crucial role. So, pamper those lovely little nubs with all the love and attention they deserve, my dearest sissy.”


Perineum stimulation: Sissies, allow me to introduce you to the ever-so-fabulous perineum, located between the scrotum and the anus. No need for any tedious preparation. Simply recline upon your body like a stunning china doll and let your fingers talk as you tantalize this oh-so-sensitive spot, just like how GGs play with their clit.


Mental stimulation: To have a sissygasm, you must be mentally ready. Think of yourself as a fully willing sissy. Watching sissy hypnosis videos can help your mind be more open to pleasure. Also, thinking about kinky things can make it easier to have a sissygasm.


Sissygasm Training


Crossdresser Sissygasm, Hypnosis & Training


Learning to attain a sissygasm is a wondrous journey, and it’s important to start with the basics. You must equip yourself with the proper knowledge, my dears, by exploring the many articles, books, and educational materials available on the subject. Communication is key, especially when engaging in a sissygasm with a partner. You must ensure that both of you are comfortable and fully consenting.


Now, let’s get to the fun part! A sissygasm starts with embracing your feminine energy and removing any trace of masculinity. Dressing up as a beautiful sissy is a critical aspect of the process, my sweetie. Adorning yourself in a cute bra, lovely makeup, and a pair of heels will make you feel stunning inside and out. And now, it’s time for the main event! Your anal training will prepare your behind for the delightful insertion of toys, increasing pleasure and reducing discomfort during your sissygasm. Get ready to experience sensations like never before, my little love.”


Here are some preparations before anal training:


 Crossdresser Sissygasm, Hypnosis & Training


My dearest sissies, cleanliness is of utmost importance when it comes to indulging in the tantalizing realm of anal play. You must ensure that your sweet, puckered rosebud is thoroughly cleansed before and after every session. And darling never forgets the power of a high-quality water-based lubricant. It will glide you smoothly and effortlessly toward pure ecstasy.


Begin with delicate, smallest of toys or even just your lovely, delicate fingers. Gradually, as your body becomes more comfortable and used to the sensation, you can increase in size. Remember to take your time. Breathe deeply, allow yourself to fully surrender, and if you feel discomfort or pain at any point, take a break.


Communication, my love, is key. Your partner should be your guiding light, helping you control the pace and intensity of the stimulation, ensuring that you are completely at ease and relaxed throughout.


And don’t be afraid to experiment, my dears. Explore different techniques, such as circular motions or playful tapping, until you find what sends shivers of pure delight down your spine. And most importantly, focus on the sensations. Pay attention to the feelings coursing through your body, and let yourself fully relax into them.


Remember, everybody is different. What works for one may not work for another. So listen to your body and always communicate with your partner, my lovely sissies.


Sissygasm Hypnosis


 Crossdresser Sissygasm, Hypnosis & Training


“My dearest sissies, allow me to guide you on an amazing journey of self-discovery and indulgence through the art of sissygasm hypnosis! This is a form of hypnotherapy specifically crafted to enhance the experiences of crossdressing sissies, elevating their sexual arousal and pleasure to new heights. You will be taken to a state of deep relaxation by a skilled hypnotist who guides your thoughts and desires toward the most delicious sexual scenarios. They will help you tap into your innermost desires and kinks, empowering you to embrace your sexuality with confidence and grace.


Through positive affirmations and uplifting suggestions, you will strengthen your self-esteem and cross-dresser identity, feeling more comfortable in your sexual experiences.


The hypnotist will also ensure that your experience is safe and positive, catering to your unique needs and concerns. It is crucial to seek out a qualified and experienced hypnotist to ensure a successful journey. So, my darlings, get ready to surrender to a world of boundless pleasure and self-discovery!”


Sissygasm Stories


Crossdresser Sissygasm, Hypnosis & Training


Girls, let me share some wisdom with you about the tantalizing world of Sissygasm Stories! Whether fictional or factual, these titillating tales are a treasure trove of sultry escapes from fellow sissies. Oh, the relatable delight they bring! Reading these stories can be an absolute revelation, providing you with many ideas, fantasies, and techniques to indulge your sexuality and reach new heights of sissygasmic bliss.


They can also provide a sense of community, normalizing and validating the desires, leaving you feeling positively euphoric.


But it’s important to remember that these stories are not strict rules or instructions. Everyone is different and has different boundaries. Some stories may be too explicit for some people. So, while these stories can be a source of excitement and learning for crossdressers, they should not be the only source. It’s important to prioritize being safe, consenting, and communicating in any sexual situation.”


Crossdresser Sissygasm, Hypnosis & Training


Here are some good reads of sissygasm stories.


Mistress AYN


Crossdressing Tales

Roanyer Crossdressing Stories


Toys for Sissygasm


Crossdresser Sissygasm, Hypnosis & Training


As sissies, you need sissy toys for anal play to give yourself the pleasure you deserve. Sissy toys are used as a means of enhancing the sexual experience and achieving the sissygasm. For example, a thick hard dildo can add extra stimulation and help build up to orgasm compared to your tiny little fingers. The following are some of the toys that can help achieve sissygasm:


Crossdresser Sissygasm, Hypnosis & Training


Dildos and Vibrators: Oh darling, I know your excitement when you touch a dildo. They are simply the ultimate indulgences for a sassy and flamboyant individual like yourself! Dildos, with their phallic shapes and smooth curves, are the perfect playmates for exploring one’s inner desires and satisfying carnal cravings. Meanwhile, vibrators, with their powerful pulsations and various speeds and patterns, add an electrifying touch to your intimate moments and bring you to new heights of ecstasy. Whether you use them solo or with a partner, these toys are the epitome of sultry and flamboyant play. So add a flamboyance to your intimate sissy life with these delectable playthings!


Realistic dildos: You might lose control and immediately take in like a horny sissy. These dildos are designed to look and feel like a real penis, often with added features such as veins and a lifelike texture. They come in various sizes; some even have suction cups for hands-free use. You don’t need a man anymore to satisfy your sissy needs as these toys are as good as a really hard penis.


Crossdresser Sissygasm, Hypnosis & Training


Glass dildos: Available in multicolor, beautiful-looking glass dildos can fulfill your wildest fantasy. These are made from tempered glass and are designed for temperature play. They can be heated or cooled for added sensation and can also be used for g-spot stimulation.


Strap-on dildos: If you are a sissy who likes being dominated by her mistress then strap-on dildos should be in your sissy stash. Get on your knees and follow the commands of your mistress as she’ll be going wild on you with these hard strap-on dildos. They come in various shapes and sizes and look like real dicks that will shake you like a lady.


Vibrating dildos: These dildos come with a built-in vibrator for added stimulation. They can be controlled through a remote or through the device itself. Imagine having a vibrating dildo in your clitty while having dinner in a restaurant controlled by your master. The humiliation which will lead to orgasm is unimaginable.


Crossdresser Sissygasm, Hypnosis & Training


Anal dildos: Anal dildos are specifically designed for anal play and come in various shapes and sizes, including graduated beads and curved designs for g-spot stimulation. Some anal dildos are very cute and available in various forms and colors.


Butt Plugs: A butt plug is a playful and fabulous addition to any sissie’s playtime! With its smooth, curved shape, the butt plug slides in easily and stays in place, while its flared base ensures that it won’t get lost inside. Whether you prefer a petite and playful plug, or a larger and more daring design, there is a butt plug out there that will tickle your fancy and make you blush. Whether you’re looking to spice up solo play or add a new dimension to your intimate encounters with a partner, a butt plug is a must-have toy for anyone seeking a sissy-like orgasm and fulfilling fun!


Crossdresser Sissygasm, Hypnosis & Training


Prostate Massagers: These are designed to stimulate the prostate, also known as the p-spot, which can lead to stronger and more intense orgasms. With the right touch, a prostate massage can be a tantalizing dance between your partner and you, leading to an explosive release of euphoria.


Bondage play for a sissy is like the ultimate sexual fantasy. It can enhance sensations and add an element of power play to sexual experiences. All my dearest sissies there, imagine being tied up, bound, and at the mercy of your big daddy. Every touch, every sensation heightened by the restriction of movement. It’s a game of trust and power exchange, where you are fully surrendered. Feathery ticklers, open-mouth masks, and silky ropes are just a few tools used to bring the fantasy to life. It’s a performance showstopper, with a standing of pleasure and sissygasm guaranteed! So, strike a pose and let the bondage play begin!


Crossdresser Sissygasm, Hypnosis & Training


Nipple clamps, darling! They’re the cherry on top of a decadent sissy bondage sundae. The playful pinch to your nipples sends shivers down your spine with each gentle tug. Imagine the sensation of tightness, mixed with the thrill of vulnerability, creating an unforgettable experience. Perfect for you to experience play with pain and pleasure. So add a little glitter to your tits with these fabulous clamps, and let the good times roll!


Sissy Chastity, my dear, is the ultimate form of submission and surrender for a crossdresser. It involves adorning with a delicate and ornate chastity belt, restricting access to your most intimate area. Submitting control and desires is the best way to achieve sissygasm, and chastity can help you with that. The delicate design of the chastity belt can be accented with lovely bows, frills, and even sparkles, making the experience all the more delightful. Wearing a chastity belt can also be a form of self-expression, showcasing one’s submissive side in a flamboyant and feminine manner.


These feminine designs can lead to a delightful sense of anticipation and excitement. They can bring a deeper connection between partners. So, my dearest crossdresser, embrace your feminine side and indulge in the tantalizing experience of Sissy Chastity. Let it take you to new heights of submissiveness, and revel in the thrill of surrendering control to your partner.


Things to Avoid for Sissygasm


 Crossdresser Sissygasm, Hypnosis & Training


Darlings, it’s important to remember that your comfort should always come first. Never push yourself beyond your limits or tolerate pain or discomfort during intimate activity. Using objects not designed for sexual stimulation, like household items, can be dangerous and is not recommended. Always steer clear of illegal or unethical behavior, as it’s not worth it. Protection is essential to keep you safe and worry-free, especially when engaging in intimate acts with a partner. Lastly, don’t forget about the rest of your physical and emotional well-being. A little self-care goes a long way in enhancing the joy of a sissygasm!





My dearest sissies, what a wondrous journey we’ve embarked on together! From exploring our erogenous zones to the delicate and sensual art of anal play, we’ve truly discovered the heights of sissygasmic bliss. With proper knowledge, communication, and openness to experimentation, we can unlock a world of sexual pleasure and surrender. So, my loves, embrace your feminine energy, and let’s bask in the glory of our bodies!

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1 comment

  1. Thank you for your information on how to achieve a sissygasm, as I’ve not had one in many years. I may have gotten away from what really turns me on a bit and thinking back to when I would achieve one, I was dressed fully with all makeup and especially red lipstick. I know it takes time and it’s a lot of work and clean up but in the end it is well worth the effort and time and they are faboulous. I guess I was not putting myself in the frame of mind that I am a beautiful woman desired by many, but it is now what I need to do. Thanks again.

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