I’d always loved wearing ladies’ clothing. Whether it was the thrill of stretching a pair of stockings over my smoothly-shaven legs or fastening a brassiere around my back and feeling it clasp tightly to my body. I just loved everything about it and relished in the moments when I was able to dress.
It started around the age of sixteen. At first, I thought it was just a kinky fetish, finding an old dress in the attic and trying it on out of curiosity. But soon I began to feel the rush of adrenaline and the sexual impulse that followed whenever I dressed en femme.
I can vividly remember the first time I came in ladies’ clothing. I was wearing a pair of pantyhose that I’d found in my aunt’s house and a netball skirt that I’d stolen from a girls locker at school. As I slid them on, I felt a rush of arousal, laying down on my aunt’s bed and sliding my body over the silk sheets.
I fantasized about being a girl, enjoying the sensation from the sheer pantyhose as they rubbed against my penis on the soft mattress. And the moment of bliss, when I began to fill the pantyhose with my come. Spilling my sticky seed all over the bedding.
It was the greatest sensation I had ever felt, aside from the panic that set in after I noticed the mess that I’d made all over my aunt’s silk linen! Of course, this wasn’t the last time I would make a mess, nor have to come up with an excuse as to what had happened and why a certain piece of clothing must have simply “gone missing”.
The day my mom discovered the netball skirt I had tucked away inside my school bag, I made the excuse that one of the guys must have put it there as a practical joke. She looked at me suspiciously but didn’t question me any further. Thinking back, it must have been pretty obvious.
A year or so later, I found myself regularly sneaking into my sister’s room, trying on her bras and panties, and enjoying wearing her skirts and dresses. I had become addicted to cross-dressing in secret and could think of nothing else.
By this time, I had started working part-time in a retail store, which is where I “acquired” my first pair of high heel shoes. One of my most vivid memories was trying to walk in them for the first time. Teetering around the house, before confidently strutting up and down the hallway, swaying my hips effeminately.
I’d almost been caught several times. Rushing off to my room to frantically strip off, hiding the clothing under my bed or in a wardrobe until I could return them when no one was around.
The time I came closest to being caught was the day I called in sick for work. My mom had left the house, and I decided to take full advantage of being home alone by playing dress-up. I was so engulfed in the experience that I didn’t even hear my mom come home early to check on me.
All I recall was the sound of her knocking on my bedroom door as I dashed into the bed and under the duvet, still fully dressed up. When she entered the room, I pretended to feel sick, asking her to fetch me a drink, then raced to undress while she was gone. The threat of being caught was such a rush and totally motivated me to continue chasing the feeling.
Slowly, I began to accumulate a small collection of my own and before long, I had a secret bag stashed away with at least two full outfits that I could wear. My favorite early set contained a pair of vintage beige nylon panties, a white satin lace cup bra, a ruffled grey netball skirt, some black pantyhose, an off-the-shoulder cotton spandex top, and my black patent high heels.
A few months before my eighteenth birthday, I decided to leave home, moving into a shared apartment with a friend from college. My flatmate, Lauren, was a meek kind of girl who spent much of her time at her boyfriend’s house.
Unsurprisingly, the first time I was left alone in the apartment, I couldn’t help myself from poking around inside her room in search of some new clothing. Although modest, she had a fairly nice collection of pretty dresses, skirts, and lingerie that I was just dying to try on.
It didn’t long before I found a sexy little tight grey skirt and some thigh-high socks that made me feel like a naughty school girl when I wore them. Coming extra hard as I masturbated frantically on her bed, screaming like a girl as I reached my orgasm, covering myself in hot sticky come.
I soon realized that Lauren’s meager and conservative collection wasn’t enough to satisfy my desire to dress, and took to the internet in search of some sexier clothing. It was at this point that I discovered how attracted I really was to dressing girly. I wasn’t particularly interested in the women that wore the clothes, but instead, I became completely besotted with the clothes themselves.
After several hours of searching, I ordered a substantial collection of cheap and slutty clothing and waited eagerly for the deliveries to arrive. As the orders began to appear over the coming days, I took the time to relish in the moment, slowly studying the look and feel of every item, pairing each piece to create the perfect outfit.
It was at this time that I discovered my love of french-lace lingerie and wet look clothing. Delving deeper into the blissful world of cross-dressing, and widening my mind to the ever-growing curiosity.
Fast forward several months, and I had built up quite the collection, including half a dozen wigs and a small bag of makeup tools to help perfect the look. It felt so incredible to finally be free to dress up at a moment’s notice. Learning to move and act more effeminate with each day, and slowly transforming into the girly crossdresser I’d always dreamt of becoming.
By now, I had become slightly obsessed with porn and had developed a particular fascination with instructional sissy training, cross-dressing encouragement, and hypnosis videos.
I’d discovered clips from mistresses online with whom I felt a sense of kinship and admiration for, and I simply adored following their instructions. This helped in allowing me to become ever more feminized, and deeper entranced into the art they referred to as “sissyfication”.
The more risqué and suggestive the instruction, the more I found myself willing to submit and comply. Eventually, this led to my fascination, or should I say, deep subconscious inquisitiveness towards the idea of being fucked like a girl. Night after night, I followed the rabbit hole deeper, slowly becoming further entranced by the concept.
Each time I dressed, I imagined a strong dominant female figure, thrusting an enormous strap-on into my face and forcing me to pleasure her. It seemed perfectly normal to want to please a woman in this way. To unquestionably and willingly submit to her demands.
As directed by the videos, I began shopping for a dildo online, astonished by the diversity of adult play toys on offer. Finally settling on the most realistic one I could find. A long and slightly thick lifelike 6-inch cock. I was so nervous when it finally arrived, trembling as the delivery man handed me the package and paranoid that he knew what was hidden inside the box.
At first, I limited the dildo to practicing my blowjob techniques, as instructed by my favorite online mistress. This certainly helped me to develop an eagerness to serve someone, wrapping my lips around a dildo and sucking the cock lovingly, even if it was just for pretend.
Sometimes Lauren would spend the night in the apartment with her boyfriend, which often meant they would be having sex in the room next door to mine. On these occasions, I would dress especially slutty and hide out in my room, listening to the sounds of their lovemaking while I played with my dildo.
After a short space of time, I became more and more intrigued by the thought of getting fucked like a girl, slowly introducing the dildo further into my play sessions. There was definitely an adjustment period, and a steep learning curve, like understanding how to properly prepare, and how essential lube was.
Soon it became a natural part of my sissyfication process, allowing me to come even more intensely than before. At this point, I was still masturbating to achieve orgasm and wasn’t aware that there was another way. That was until I stumbled across a site dedicated to sissies.
This is where I gained an understanding of what a sissygasm was and read blogs from gurls who had learned to achieve one. The site contained guides and explicit instructions on how to achieve this euphoric experience. It was here that I first witnessed a video of someone coming without the need for masturbation.
I watched in disbelief at the fact that her clitty was locked away in chastity, yet she was still able to achieve a hands-free orgasm merely from anal stimulation alone. I was mesmerized, my eyes glued to the screen, completely intrigued and mystified by this newfound experience.
‘I just had to try this for myself!’ I thought, enthusiastically.
From what I read, this would also become a vital step in my progression but would take some dedication on my part. The guide had outlined a few rules that I must adhere to before attempting to sissygasm.
The first rule was that I could no longer masturbate nor touch my clitty at any time, aside from for hygiene reasons. The second rule described the behavioral changes I must make, such as wearing lingerie under my clothes at all times, peeing sitting down, and keeping my body completely hairless.
The final rule outlined the mindset that I must achieve, which described how I would need to adjust my thinking, transforming my perspective from a masculine mindset to a more effeminate one. All of these rules were to be followed for a minimum of two weeks.
After an excruciating couple of weeks, with no masturbation, I finally reached the next step in the process. I was now permitted to watch porn again, but with two omissions. I must always be dressed in sexy lingerie, and I was still not allowed to touch my clitty. I was, however, encouraged to practice and play with a dildo while I watched.
This was by far the hardest part of the process.
I’d decided to dress in some of my new French lingerie, slipping on a cute pink lace-up corset with suspenders and a matching silk thong. Completing the look with some natural skin tone sheer stockings and a pair of 6-inch sparkly stiletto heels.
As I began to watch, my attention became fixated on the man in the video. Carefully anticipating the moment that his cock became exposed, making my mouth water.
I’d positioned the dildo on the desk in front of the computer monitor, so I could continue to watch while I replicated the girl in the video. My heart fluttered at the sight of his large erect penis, watching eagerly as the girl slid down to her knees in front of him.
Following her lead, I copied her movements as her hand reached out, cupping the shaft, sinking her mouth over the head of his cock and swallowing it hungrily.
My body trembled as I assumed the character of the girl, eagerly servicing the dildo as if it were a real cock. I’d never really felt an attraction to men, but the allure of a big cock was intoxicating. I was moaning audibly as I continued to suck and swallow the full length of the dildo.
At this point, my clitty was tingling and I could almost no longer hold out, craving to masturbate in a wild state of lust. I resisted, resisting the rules of the guide in my head.
“You must not touch or play with your clitty at any time!” voraciously, gobbling down the dildo as I whimpered and moaned loudly.
I’d completely lost track of time when the video ended, not realizing how long I’d been practicing fellatio, losing myself in the moment. When I looked down at my clitty, I could see a wet patch soaking through the silk thong and a small amount of precome slowly trickling out.
This was the time, I thought, recalling the advice from the site. The guide outlined that in the final stages of the process, when each of the necessary steps had been completed, you would be permitted to use an anal device, such as a dildo, to pleasure yourself like a girl. The only rule that remained was that you could still not touch or masturbate your clitty.
Releasing the suction cup from the desktop, I reached down and positioned the dildo beneath me, sliding the thong to one side and generously applying lube around my boy’s pussy. As I did so, my finger slipped inside accidentally, making me gasp with surprise and delight.
My “pussy” was ready and I was aching to take it deep inside, lowering myself slowly down onto the dildo and letting out a feeble but tender moan as it entered me. I remembered the mantra from the guide, that instructed me to repeat out loud the following words whenever I was in sissy mode.
“I’m such a good sissy. Please, fuck me like a girl,” focusing on my breath as I repeated the words, again and again, grinding my ass and speeding up, I rode the pretend cock, rubbing my hands all over my body and pinching my nipples hard.
“I’m such a good sissy. Please, fuck me like a girl,” I begged louder, my moans echoing around the apartment.
“I’m such a good sissy. Please… please, fuck me like a girl!” I screamed.
Moaning louder, my body trembling and shaking as I arched my back, grinding my hips back and forth, feeling the dildo pressing harder against my prostate.
It was probably a good thing I was alone in the apartment. Or else Lauren would have most certainly heard me through the walls. The thought excited me as I let go of my inhibitions, moaning louder still, continuing to repeat my mantra.
“I’m such a good sissy. I’m such a good sissy,” I squealed, my prostate throbbing and vibrating against the dildo, making my clitty tingle with sensitivity.
“Oh yes!” Please, fuck me like a girl!” I screeched.
My entire body began to tremble as my flaccid clitty slipped out of my thong and began flapping between my legs. I could feel the sexual energy rushing through me, making me levitate like an out-of-body experience as I looked down at myself with lust.
The feeling was incredible, unlike anything I’d felt before. Sending a warm wave of sexual gratification that emanated from my prostate, traveling all over my body, then weakening my legs as the sensation built.
I whimpered passionately, letting out a girlish moan, shaking with pleasure as my clitty began to ooze streams of come all over my stockings, making them stick to my legs.
“I’m such a good sissy,” I moaned one last time, the euphoric sensation rushing through my body, making me shiver uncontrollably. As the intensity of my orgasm crescendoed into the final climax. My clitty spilled out the last few drops of come.
“Oh my god, yes,” I panted, collapsing onto the floor, aimlessly attempting to regain control of my extremities following my first intense sissygasm.
There was a pure sense of serenity as I lay there, covered in come, trembling faintly. The dildo holding still and dormant inside me while I tried to catch my breath.
For some reason, I flashed back to the day that I first dressed. Remembering my innocent curiosity and the excitement of wearing a dress for the first time.
Perhaps it was fate that led me to this point? I wondered. Or maybe I was always destined to discover the magical experience of learning to sissygasm.
