July 19, 2026
July 18, 2026
Milestone Moment in my Sissy Life: My First Real Sissygasm!
Originally Posted Aug 15th 2020
I wanted to share this with everyone on Thursday, but to be honest, I was too swept up emotionally to put everything into proper context. The other afternoon something truly wondrous happened to me that created a new major moment in my sissylife: I experienced my first ever Female-like sissygasm!
Since discovering my inner sissy and recognizing the person that was Devina needed to grow out of the shell she had been kept in, the sissy journey I embarked on has been full of firsts and mind blowing experiences. I've been transformed, I've modelled, I've been fucked as a sissy girl by Transwomen, taken Shecock facials as Devina, started this blog, shared my secret moments and experiences as a sissy gurl with the world, and have proudly been a slut for more than one Shecock.
Every step along the way has only propelled me deeper towards wanting to experience the most personal and intimate feelings and sensations from a Feminine perspective and emotion as possible.In fact my entire sissy chastity journey has been based on a deep seated feeling that I had to completely put behind me any physical and sensual pleasure from any sort of male influenced perspective and begin a quest to see if I could learn how to achieve Womanly pleasure, in a physical, emotional, and physiological place as possible.
I've been so blessed to have Lady Diva, encouraging me every step along the way, and to know that She truly understood where my submissiveness was taking me; away from session based experiences and more towards deeper life altering experiences which have only deepened my submissive nature and has taught me to love Women on a level I never knew existed before.
At the heart of my desire to express Devina to the world, is the need to come out to more and more Women, to show them that a sissy has the capacity to love Women on a level far deeper than they might think. My self discovery as a sissy has always led towards the Female gauntlet of shock, surprise, ridicule, embarrassment, laughter, incredulousness, humiliation, and hopefully turn the corner to understanding, learning, and acceptance, and finally celebration of my sissylife. But for me, I needed to learn as best as I could what it meant to experience the magic of a Female orgasm. Could a sissy ever reprogram their original male biological settings to cast aside the impulses of immediate selfish gratification and all the icky traits and habits that go along with them, in order to tap into the Female spirit and consciousness to find the ever elusive Womanly sissygasm?
When I discovered that sissies could bring themselves to a hands free sissygasm by stimulation of their p-spot, I was wonderfully fascinated. I foolishly thought that such a thing could be easily achieved by any sissy but as many Women in the world struggle to achieve a Female orgasm, I always struggled mightily to bring myself to sissygasm; always coming close, feeling the wave build but never being able to let go mentally enough to let it wash over me. My mind was still preventing my body from changing how it experienced sensual and sexual pleasure. Something more drastic was needed. Sissy chastity
My sissy chastity journey wasn't a punishment at all but something I entered into on my own. I thought that extended long term chastity could be the key to ultimately reprogramming my mind to allow me to tap into the Feminine emotions, and empathy that was growing within Devina's personality, combined with a deeper understanding on how her submissiveness was changing who I was on a day to day level. I also knew that I couldn't cheat the process by using dildoes, monkey rockers, or fucking machines, because I needed to tap into the source of a Female orgasm, which starts in the mind. A Woman visualizes Her eventual orgasm based on mental images added to emotional desires which ultimately manifests in an intense physical wave of release that crashes on Her shores. THIS is what I wanted to achieve if I could!
When I began to experience sissy leaks with no physical stimulation of my locked sissy-clit or asspussy, it was a momentous event, and each time it happened I felt a beautiful rush of warm emotion, as I visualized Lady Diva or other Domme's in my life being there to see it and to visualize their smiles and see the satisfaction on their faces. Each sissy leak would have me repeating in my mind in Lady Diva's voice, " Good gurl! That's my lovely little sissy..." Perhaps I didn't even know it but I began to condition myself to associate a sissy leak with a Women's satisfaction in me. This has gone on all throughout my almost 1150 days now in sissy chastity.
As time has gone on now into 3 plus years of sissy chastity and only a could months away now from my 6th year of denial of Womanly sex, I've focused on the only sexual pleasure that I knew could bring me happiness and that was Shecock. It's been fascinating to experience the drastic drop off sexual physical stimulation from Women, simply knowing that I can't provide Them any physical pleasure with my locked sissy-clit. Yet as a sissy slut I can pleasure a Woman's strapon Shecock, and all manners of TGirl Shecock. As Lady Diva can attest to in O/our chats, Shecock is the driving force in my desires for physical pleasure and emotional satisfaction. The only pleasure I can hope to receive from any Woman is their acceptance of me as a sissy, or their amusement in how useless my sissy-clit now is, or in their satisfaction in my manners or performances as a sissy slut for their pleasure. The daily reprogramming of what constitutes pleasure, and emotional release has been a slow and steady one, even if the magical sissygasm continued to elude me.
Twice now, both times during morning dreams before awaking in the past few months I have experienced something unique. Both times involved rather vivid imagery of pleasuring Shecock when I have felt a sudden pulse inside my sissyclit. Similar to what I used to feel during an ejaculation, that first contraction. Both times it woke me, and both times I was amazed at what just happened, but no further contractions happened, nor did any leaks occur. Yet both times I felt an enormous sense of happiness in thinking that my mentally stimulating sexual imagery was creating a physical reaction in a way that a Woman might feel. The mind visualized and the body deep inside the p-spot region reacted, even as my sissyclit wasn't erect but just semi turgid. Neither time was that experience something that I was able to control with conscious thought but it made me so proud that somewhere deep within me, my mind was being reprogrammed to react instinctively towards Shecock now in a sexually satisfying way. I shared each experience with Lady Diva and W/we both marvelled at the experiences
But something magical happened Thursday afternoon. My goodness did it ever, and it involved conscious thought. My job requires me to sometimes travel to one of our offices within an hour or two radius from my city, and on Thursday afternoon I was driving back from one of them, when I noticed a twitter notification from an earlier tweet by Domme Lady Mila, and I was obliged to quickly pull over and respond and a quick twitter convo ensued.
I was happy to see Lady Diva engage by liking parts of O/our exchange, and I always am quick to give any credit to Her, when a Domme offers a compliment to me, as I'm merely the result of Her efforts. And with that small exchange, I had to pull onto the road again and carry on back to my office. I felt a sense of satisfaction knowing my pathetic little sissy-clit had amused Lady Mila, and a sense of pride swept over me that I was able to demonstrate how effective Lady Diva has been in crafting a well mannered sissy sub. My little sissy clit nub was admittedly awakened in my panties to it's semi turgid peak state, but since I was driving, there was no attention given to it, but my mind now was flooded with emotions and images of Lady Mila now laughing at my sissy clit. This then led to other visual images of reoccurring desires to be presented by Lady Diva in front of a gathering of Women (both into BDSM lifestyles and not) in my full sissy self for their pleasure and amusement. I suddenly was swept over with thoughts of inviting Women who are my FB friends to this sissy social, where I would greet them, then kiss their feet/shoes to welcome them, serve cocktails as they introduced themselves and began to feel comfortable as Lady Diva welcomed them all and began to explain what was to occur for their amusement. The amusement would be me in full sissy glory having my asspussy spread open and fucked by a beautiful TGirl, and alternating with any of the Women in attendance who wished to use a strapon Shecock on me as well.
Then it happened....as I was driving
A strong contraction in my sissy clit!
It snapped me out of the daydream I was having while still on the road as I suddenly was surprised and wondered what just happened? My sissy clit didn't get any harder inside the confines of my CB6000s but my entire pelvic region was getting warm and I was feeling flushed. I tried to calm myself down, breathe deeply and relax, also trying to refocus my mind away from the flood of imagery that had swept me up.
Two deep breaths and I tried to relax my now tense kegel muscles that I've leaned to understand their sensations when a natural sissy leak has occurred in the past with out any orgasmic like contractions. I thought I was calming down, but my mind couldn't remove itself from the Femdom sissy party in my head when suddenly...
Another twitch in my sissy clit! Then a second smaller one!
It was in a split second while travelling at 65 mph on the highway that I knew I was about to have my first Womanly sissygasm, and there was nothing I could do to stop it!
In wave after wave my sissyclit still mostly limp, began to pulse and I suddenly felt the warmth in my panties as my p-spot sissygasm swept over me all while driving! My sissyclit released uncontrollably for almost a mile and a half in an intense sissygasm that had me gripping the wheel of my car and looking down to see what kind of mess I had made in my lulu panties. As I felt my p-spot empty it continued to pulse and pulse like waves rippling and I was so excited, happy, embarrassed, and stunned all at the same time!
In my head all I could hear now were the party guests at Lady Diva's laughing, high fiving, cheering, and celebrating as their little sissy just made a cummie in her panties for Them. I struggled to find a place to pull over where I could discretely try and clean up as best I could. Pulling over in a small wooded drive approach I was able to see that my sissygasm was unlike any ejaculate I remembered having, as the wet was not like a cumshot but like a Woman who can squirt, with little to no scent.
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Thankfully I was able to find some napkins in the car to clean my panties, which surprisingly had soaked up a large part of it, so my slacks only had 2 wet spots that I was able to dry off the best I could directing the car's vents to that area, while i composed myself to get back to my office. My mind was full scatterbrain, and has been for a day and a half.
For over 3 years, all I've ever wanted to do was to know that I could find the door to a Female-like sissygasm, and the only way I wanted it to happen was by being taken by a Woman or Transwoman's Shecock. That remains the only way I ever want to experience sex now, but I've discovered that I can create a sissygasm the same way a Woman does, and that starts in the mind.
You all have no idea how proud and happy this makes me as a sissy!
Love
Devina
Devina's Domme of the Day July 18
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