Showing posts with label Ass Pussy. Show all posts
Showing posts with label Ass Pussy. Show all posts

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.


 

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 

June 6, 2026

If You Knew You Wouldn't Cum...

 


  When the majority of us discover kink as male subbies, we do so looking for a different way to get off that bends our minds, hence the term Kink. We pretty much all start out as kink players. Some of us stay there contently, while others drift between kink and deeper levels of submission, while fewer still begin a journey into submission that they may not even know they are on, but one day realize they are far from where they started.

My initial steps into submission and kink play was no different. Things began to change once I felt safe enough to trust Mistress Morganna (Lady M) and later Lady Diva Cane. Once I began to confess my inner desires to explore and develop the inner sissy within that was there from my earliest days, a new world was created. It's like finding yourself in a room with many doors and you don't know where any of them lead, but YOU know that you need to go somewhere.

Being less than three weeks away from my 9th Chastiversary, I have learned a very valuable lesson in my sissy chastity experience; the act of me ever cumming in front of my Mistress or any Dominant Woman is completely inconsequential. It has zero importance. As my sissy clit shrinks and my sissy leaks become less and less frequent, I'm thrilled at the fact that almost 9 years in, my sissy clit is completely useless to any Woman. The only purpose it serves now is a constant reinforcement that I must continue to learn how to achieve orgasms from a mental aspect first, then transferring that energy into my p-spot. My sissyclit does not need, nor should ever receive attention in any manner that would resemble masturbation.

 


Sharing this monumental self realization with Lady Diva was a huge moment for me. Why should I burden Her with my filthy urges? Why should any Domme really cater to subbies nasty urges to spunk and make a mess. Wouldn't that time be better spent pleasing your Mistress?

But wherever you kneel in the kink world, could you fathom seeing a Domme and knowing that you will have zero expectations of getting off physically? I mean you still might, right? A powerful Dominant Woman has many abilities in Her toolbox to have you achieve all sorts of physical feats, but if you knew that your best odds would be 50/50, would you continue? Would it be a turn off to your selfish arrogant male ego that your needs wouldn't be attended to? Or perhaps would you be intrigued in what you might learn about yourself and your Domme in putting Her needs before all of yours?

 


Maybe it's my sissy nature and my growing desires to learn to try as best as possible to cum in a Female way, but there is something incredibly fulfilling in reaching a place in my sissy life where I no longer care if I leak, squirt or dribble. The smile on a Domme's face is far more rewarding. The pride of ownership that Lady Diva has in my sissy clit gives me a sense of sissy purpose. It's a feeling I never could have possibly discovered if I had remained merely a kink player.

Whether you are ready or not to ever get to that plane of submissive existence, you should at least ask yourself from time to time, "Is my cumming more important than My Mistresses' satisfaction?"

You might be surprised where you one day find yourself...

 


As a Shecock loving sissy, the other reason why I never need to cum again is that my purpose in life as a sissy is ultimately to make Shecocks cum. Again, my sissy dribbles out of my limp sissyclit mean nothing compared to devoting your abilities to make a beautiful rock hard glorious Shecock explode, preferably all over your face!

 


Feeling the sensation of a Shecock explode in your mouth and/or all over your face brings a sense of accomplishment like no other. You have brought beautiful physical pleasure to another, and superior person, and they have rewarded you with everything you really need. Feeling Her cum on your face cements your place in life, and gives your sissy life true purpose. When you find this nirvana, it's essential to share this with as many Women, both Dominant and vanilla as possible. Let that cum wash away any sense of shame and never look back at what you used to be.

When you find all that, why is your sissyclit even relevant?

It's not.

Sincerely Sissy

Devina 

March 21, 2026

Spring Comes and Devina Gets Horny

 


I'm still buzzing on cloud 8 or 7 as I share this with you all, but the ebony goddess above just finished pounding my little asspussy and treating me like the proper slut I really am.

My day was spent preparing myself by being fully shaven, clean (inside and out gurls) and the favourite part, picking out the proper outfit. It had been a few years since I have seen Sunshine and a lot has changed in my life, although my last encounter with Her had her fucking the living hell out of me too, and perhaps signalled the inevitable change that was to become in Devina. But I was just a bottom boi bitch back then, not what I presented to Her this evening.

I came out of Her bathroom in a black, white, and pink mini dress, knee stockings with pink bows at the back, pink Mary Janes and my sissy clit locked in it's chastity and graced in a pair of pink lace panties, along with Devina's trademark red locks. Needless to say Sunshine was surprised but pleasantly, much to my relief. She embraced me like a sister and we both sat on the bed chatting and catching up on my new persona.


 

She was blown away and loved the new person She saw before Her and couldn't wait to see more of me. I showed off a little as She took me all in and then refused to wait any longer as She had me assume the position, on my knees with Her black growing cock in front of my face as I immediately did what a gurl slut does and gorged myself on Her cock.

It had been far too long since I've tasted real She-cock and I completely gave in to this growing black piece of candy in my mouth. I wanted to lick it, kiss it, rub it on my face, all over my lips, kiss Her balls, I just wanted IT ALL! She sensed my enthusiasm and had to take her cock away from my mouth as She was turned on by this sissy slut worshiping Her cock. No, She didn't want to paint my face yet. She wanted my asspussy and I was more than ready to oblige.

I was soon bent over, knees on the bed, Mary Janes pointed toes horizontal like a good slut does, as She began rubbing Her lubed cock all over my asspussy. My mind raced back to the last time, years earlier when I was in the same position, just a hairy male bitch. Now this was different. This was an entire evolution of the real me! I was shaven fully, sissified, cocksucker lipstick smudged and asspussy exposed and eagerly needing to be filled. Sunshine slowly entered me and with steady force began to open me up. "Oh my!"

 I knew I was going to take it all, and I had tried to be relaxed as possible but being grabbed by the hips and feeling Her searing hot cock enter me filled my sensed to overload and I gasped. She sensed my tightness and took Her time slowly opening me up until completely inside me. Gawd I loved the feeling of Her cock filling my asspussy and I missed it so. She began to drive Her cock deep inside me and soon enough my complete inner slut, now exposed fully as the sissy whore I really am, just took over and I pushed back hard on Her cock each time it entered me.

"Oh Devina, you like that?" She cooed

"Fuck, I love Your cock in my asspussy! Fuck me!" I moaned, loving each thrust.

By now I was not being some lethargic bottom boi, like long ago. I was being impaled by this black She-cock of my dreams and I didn't want it to end. I was driving myself on it, losing myself on it, rotating my hips and clenching on it. I was a slut and I wanted to fuck this She-cock like a dirty whore would. No quit, no stopping, just being used like a slut. For the first time, Devina was outside Lady Diva's Dungeon and being exactly what she's always wanted to be. Each thrust of black She-cock confirmed my place, my purpose, and my reward for devotion to the Feminine Spirit. The Universe at that moment was rewarding me for my love given to all Dommes, all Women, and all TGirls. My reward was being fucked like a sissy gurl, my sissy clit locked away and useless, pleasing the cock inside me with my asspussy, my enthusiasm, and my wanton desire.

 


"I LOVE Your cock in my asspussy...pleeeeeeeaaase fuuuuuuuuck meeeeeeeee!!!!" I hoarsely moaned as She grabbed my hips harder and with one hand pushed my face onto the bed, giving Her full entrance deep inside my asspussy.

Sunshine pounded away a little while longer until She gave me one last deep thrust feeling Her balls slap my ass as She ordered me to turn around because it was time for a slut's reward: A face full of cum! A cumshot from Sunshine is more akin to taking a cumshower, and she painted my face, lips, chin, hair, dress, boobies, and I lapped it up willingly. A final kiss on the head of Her cock was the icing on the cake, taking a last glorious taste of She-cum.

 


 I stayed between Her legs long after Her eruption as we talked about Lady Diva's progress with me and how She would like to take part in my ongoing training. This sissy was indeed heaven! A face full of She-cum and knowing that coming out to Her as Devina was now going to pay off in my ultimate dream to be with lady Diva and Shemales at the same time. 

 


It was a beautiful night as I took another step on my own as Devina, and was embraced by a beautiful TGirl who not only rewarded my courage, but after She encouraged me to keep transforming, and not to turn away from it. Those words of acceptance and encouragement were so welcomed by my inner Femme spirit. Tonight I got to be who I really wanted to be the first time I surrendered my asspussy to Sunshine years earlier, and I couldn't be happier... 

February 17, 2026

Closer and Closer

 Originally Posted Feb 17, 2020

 


 To me the most beautiful thing about the Female orgasm is that it starts in the mind, and that in many instances, a Woman can visualize Herself towards an orgasm first, rather than just physical stimulation leading to one. Women create a build up of mental and physiological energy that releases in a wave of pleasure around Their sexual needs and desires. As a sissy, transitioning away from our born methods and habits of achieving orgasm as males would, and learning how to achieve orgasms in a truly Womanly way, requires a lot of work, and understanding.

As sissies develop a deeper understanding of their Feminine self, they begin to progress into learning how to cum without touch or the act of stroking masturbation and begin to start training their asspussy to stimulate their p-spot. This is not an easy thing to do as I'm still learning but it's still focusing on the physical aspect. We gurls tend to miss out on the mental aspect of cumming like Women do, and that is the other side of the equation.

 


Over the last year there have been instances in my sissylife where as I've been enjoying a nice morning sleep, my waking dreams have been centered around Shecock and being fucked in my asspussy with images of Lady Diva and Her Female friends watching, and enjoying the show. The mental images are very powerful and even being locked in chastity, with my sissy-clit mostly limp, I've been stirred awake by a small convulsion of my p-spot. Not quite enough to make me leak into my panties but undeniable that my dreams of being taken by Shecock, could lead to a mental type of orgasm for real. Sharing theses experiences with Lady Diva has been another shared joy of my evolution as a sissy gurl. Harnessing the power of the mind to begin the process of cumming like a gurl is a mind blowing thought.

 


This should be the goal for all sissy gurls. Harness the power of your minds after a lengthy period where we transform ourselves away from physical stimulation of our sissy-clits, and learn how to achieve pleasure and orgasm from our brains connected to our p-spot via penetration, rendering our sissy-clits useless and limp as the sissy cum is fucked out of us. Transforming yourself into a Feminine creature that orgasms fully limp will most certainly fill your Domme with pride in the efforts She has made into permanently transforming you into a proper functioning sissy.

These are the only true gifts we can give back to the Dommes in our lives. The proof that Their guidance and training has permanently made a difference in our lives via our submission.

 


If you truly wish to cum from now on as a Woman, it all starts in your mind, and visualizing your true joys in orgasm as a sissy. Lets all make the world a better place by deepening our transformations. None of us will ever wish to go back, I'm certain!

Devina