Boys Make the Best Girls

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A young man's journey to total sissy bliss.
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LiveSteam
LiveSteam
15 Followers

Part 1- A New Hobby


As a freshly graduated adult, if I could give the younger generation any advice, it would be to develop new skills and hobbies. Before I left home for university, I did little else than plan games and surf the internet. I was a classic nerd. I remember feeling so embarrassed during the first week with my vamp-ish pale skin, ridiculously square glasses, and a long greasy mane of jet black hair. All week I would go to sleep surrounded by the noises of my fellow residents socializing, partying and eventually fucking. One girl in particular would put on a spectacular performance, and I could hear every moan, whimper and scream through my walls, before to long I was obsessed, rushing back to my room to hear her getting ravaged, but of course obsessions like this only develop, so it did not take much time for me to start following her to the gym.

Now she was nothing like me, she was a bubbly blond with a classic hourglass figure, while I was still in my skinny awkward nerd body, so in a gym I was basically invisible. She would run through a legs, ass and tummy routine everyday, and of course scores of men would turn up to ogle her. Over the course of a few days something strange started to happen: I would get jealous, not of the flirtatious looks she would dole out to her admirers, but of the attention she was getting. And when I sat on the floor listening to her orgasm, I wasn't imagining taking her, I was imagining being taken like her! Of course I would push these thoughts aside, open my laptop and watch regular porn like a regular guy, but I had changed, each time I idolized the man, and stretched out my body like the woman in the video. Of course after I came I would slam the laptop shut and pretend it hadn’t happened, but after this cycle repeated itself again and again I had to admit that I wasn’t the man I thought I was.

Thankfully it was the 21st century and I had internet access, or else I may have never discovered where to go next. At first I googled "cross dresser", there were a few items that kept me coming back, but after a while it seemed to be more performative than I wanted. Like most intimate emotions it’s hard to describe, but I have never thought of myself as a gay man, and while I certainly enjoyed seeing dolled up men getting dealt with I had no desire to be seen as a man. The crossdressing videos led me to experimenting with female underwear. Sometimes I would watch straight porn, sometimes I would watch crossdressing porn, but now I would always put on some panties and pump my tight little ass. It’s normal I would tell myself, just a passing fetish, that was until I saw a link to a video titled "sissy breeding".

In the video an adorable brunette is bent over an office chair wearing a cute little plaid skirt, without warning a large older man enters the view and starts fucking her from behind, I say her, but of course she's a little sissy, you can watch as her cock swells up with pleasure before she rains hot cum all over the chair, what's most incredible is she didn't even touch herself, and neither did the man. Instead he fucks her like the sissy whore she is, he's not there to make her happy; he's there to cum, and that's it. Eventually he builds up and empties his load into her ass, and by this point the sissy is shaking, she has been ruined by pleasure and can barely talk.

When I watched that video I saw myself. Tiny feminine limbs, a weak soft voice, and a desire to be taken by a real man and filled with his seed. Ever since I saw that video I knew what my life would become. I didn’t want to be the man doing the fucking, and I didn’t want to be a woman being fucked, I wanted to be an object of desire, I wanted nothing more than the male gaze.

I started immediately. From there I opened another tab and started googling " bra, thongs, miniskirt", the plain jane panties that I had started with were overtaken by a collection of revealing lace, tight figure hugging tops, and scandalous panties. I watched makeup tutorials, I shaved and plucked my body, and of course I ordered a butt plug. That was the first real joy for me, to be sitting in lectures or talking to my classmates knowing that my little tush was all plugged up. I adored the gentle vibrations I felt through my body whenever I moved, it was delightful to know what a slut I was becoming. On more than one occasion I caught my lecturer staring at my ass, maybe he knew I was plugged, maybe he saw my panties as I bent down, the reason didn't matter. I just loved the attention. My semester was filled with the joy of my new secret hobby.

After my ass was used to being plugged and I had amassed a good range of panties I started to make myself up. I chose a bright red shade for my lips, I thought it contrasted nicely with my pale skin and black glasses. My hair was pretty long for a boy, so it didn't take the hairdresser long to cut it into a pixie bob. My main wardrobe was still pretty plain at this point, but I had become used to being stared at. Even so I was still a virgin and lacked the confidence to really seduce a man. I still listened to my neighbor being stuffed with cocks, but now rather than listening with a hand down the front of my pants, I would listen flat on my back with my legs in the air training myself for my first man.

My journey had just begun.


Part 2- Baby Steps


Even though my transformation was profound and all consuming, it did not lead to quick results. to be honest the whole experience was so intimate that I was regularly rushing off to the bathroom to clean up. I was a constant mess of lace panties, silicon and cum.

Nevertheless I was thoroughly committed to finding a cock to serve, however I was disappointed to discover that many men on campus were decidedly prudish. I saw so many stares and bulging pants, but nobody took the initiative. I think they were worried about the closed university environment and worried about rumors. Even now I love seeing the mix of desire and concern flash across a man's face as he realizes he wants to take me, but that's part of being a good sissy. We are not only here to be a receptacle for their sexual whims, we are also a way for real men to break away from society's stiff constraints, sometimes they need to get away from the 9-5, from the pressure at the office, and they need to be an animal. That's what a sissy is for; we help men reach their true nature. Back in the early stages of my sissification I hadn't realized this, the truth is that as much as I had to train myself, I also had to train the men around me, but first I had to find one.

During this period I kept going to the gym, initially I just wanted to maintain my slender build and to tighten up some key areas. Through a process of trial and error I found the perfect gym get-up. First of all, any aspiring slut (sissy or female) needs a good range of crop tops, these need to be short enough to ride up and show your chest, pair these with a set of skin tight plain leggings. It is important that these leggings are plain! You want your audience to focus on the line of your panties, or the line or your crotch, now if you're a filthy sissy whore you'll need a chastity cage, this will keep your beta cock down while you workout. As an extra personal note I like to mix my physical exercise with my sissy exercise by putting in a challenging plug and using a stationary bike. I promise you that the ability to hold a plug in while pumping the pedals will help you be a desirable and fuckable partner.

It was during one of these workouts when I first noticed my target. He was working as a personal trainer with some plastic Barbie with blow up tits, but every time I stood up on the pedals of the stationary bike, he would all but totally ignore her and fixate on me. He had a thick muscled body, a thick black head of hair hid his warm brown eyes, and his mouth was tightly pushed together as he tried to refocus on his client.

There was someone about his gaze that made me feel like I was in a dream, I could see a bead of sweat running down his chest. In my head I imagined that bead running down his abs, down his crotch before being gobbled up by my hungry mouth. His client rolled her eyes and cleared her throat in annoyance, clearly she was hoping for a fumble after class. She couldn't handle the truth, that I was more of a woman than her, that her tired tits and pussy were boring, that she was stale and I was fresh. In a perfect world women like that would bring men to us to learn how to serve, as it was I won the competition and my validity was confirmed by the attention of the alpha male.

I slowed my pace on the bike and bided my time, I knew that I had to do something, I just didn't know what. After an eternity of banal chatter that airhead finally left and my man headed to the showers. I squeezed myself into the corner of the locker room as he peeled off his shirt, wrapped himself in a towel and headed to shower. By the swaying of the towel I could tell he had a hog on him. As he turned on the water I rushed into the adjacent stall. There was a plate of translucent glass between us but I knew he was rock hard and staring at the outline of my body, I turned on the water and slowly bent down, even with the water pounding down I could hear him grab his cock and begin jerking. My own beta cock was dripping with precum, which I rubbed my fingertips into before reaching them into my own mouth.

Step by step I backed up into the shower divider, I pushed my ass right up against the glass so he could clearly see the plug inside of me, it even made a conspicuous clink against the glass, but by this point it was too late to worry about anything else. I straightened my back and turned around, my tiny beta cock uselessly bobbing up and down. My knees were shaking and I had to put a hand out to steady myself as I came to see the outline of an alpha male clearly jerking himself off to my visage. His cock looked huge, dangerous and delicious. I tried to imagine how it would feel in my mouth or splitting open my sissy pussy, but my mind was transfixed by the reality I was watching.

Without warning his shoulders shuddered and a fountain splattered on the divider and wall. He slammed the water off, turned his back and wrapped himself in his towel, as he stepped to leave he paused and whispered, "eat it". Then he strode off down the corridor, his feet pounding off the tile floor. Unable to contain myself I rushed out of my stall and into his, whether or not anybody saw I don't know. My desire, my nature and my fate pushed me down to my knees putting me at eye level with his seed splattered on the stall. A breath ran into my lungs as I steadied my nerves, then I opened my mouth and licked it up. It was thick and salty in my mouth, it had the stink of a real man and my first instinct was to gag. I squashed the reaction, and sucked up every drop.

I can't tell you how long I was on the floor of the shower, but my belly was full of seed, and my mouth was coated in a film of cum. My mind was racing, my beta cock was leaking, and it was perfect.


Part 3: Hiding in Plain Sight


My experience in the shower stalls was an intimate learning experience for me. I had taken a chance and put myself out there, and I got a hot load as my reward. I was in the habit of going past the gym, but ever since my delicious trip to the shower, my alpha was ignoring me. I got the impression that he was taunting me in a way, letting me know that he could drop me, or fuck me at anytime. I was simply an object for him to play with. Unfortunately before I could confirm or deny these suspicions real life got in the way, and I had to put my personal journey on hiatus. The Christmas holiday was around the corner, and as much as I was a cock hungry whore, I wasn't ready to explain myself to my family.

I packed a small suitcase to take on the train with me. It was mainly boyish clothes like skiing pants and baggy shirts, but like a good girl I made sure I had a wide selection of clean lacy underwear. I was forced to take a smaller buttplug, I loved stretching out my boipussy, but the constant erections and dripping precum would make things awkward at home.

Without too much fuss I made my way to the train station, I had booked a seat on the overnight train. The weather was beginning to turn cold, I was frozen to my core, and I had to bundle myself into a giant coat. I was looking forward to the relative warmth and comfort of the sleeper train. After so long being outrageously flirtatious, and constantly seeking the approval of men it felt weird to be alone with my thoughts, and worryingly all I could think about was cocks. The obsession was deep within my brain. I did my best to forget about it as I collected my ticket and waited on the platform for the train, but as the station got busier, and more and more men stood around me my mind was filled with thoughts of being defiled on the platform, I wondered how many men I could keep hard on such a cold day, and without even realizing it I was grinding my ass up against a stranger behind me. To my surprise he squeezed my ass and then reached between my legs to feel my tiny dick. He gave me a few gentle strokes before leaving and walking off to board the approaching train. I was thankful for my giant coat as it had hidden my brief encounter, and would buy me enough time to find a toilet and clean up the precum that was gathering in my panties.

The train was busy but not rowdy. Most of the crowd were university students and staff heading back for Christmas, it was a 6 hour journey, and nearly everyone was getting set up with headphones, a book or simply resting their head on the window and going to sleep. By the time the train had started moving and we had left the town the queue for the bathroom had totally disappeared and I was confident that I could comfortably tidy myself up.

I was staring up when a firm hand gripped my wrist, "We didn't finish earlier". The man from the platform was standing in front of me, even beneath his thick winter clothes I could see the bulge of his throbbing cock.
"Eerrr I need to tidy myself up". My voice came out as a whisper, I didn't know what to do, this man wanted to use me, but the train was too public, people would hear. I could feel my face growing red with embarrassment, but the man acted as if he hadn't heard me. He was slightly older, maybe middle aged, he had a thick head of hair and a full beard, both black but peppered with streaks of grey. He looked as if he had an athletic past, but over time he had grown a bit of a belly. I could smell sweet Christmas food on his breath, and imagined that mouth clamped down on my neck. He must have sensed me wavering, because before I could respond he practically dragged me to the bathroom.

Luckily the bathroom was made to be accommodating so we both easily slid inside, and by this point nearly everyone had fallen asleep. I just needed to do my job silently and quickly before anyone realized what was going on.
The stranger from the platform sat me on the toilet, so I was level with his cock. He took a second to look into my eyes, he had a friendly twinkle, but also a deep desire. I had been mentally preparing myself for this situation for weeks by this point, and I knew exactly what to do. I slowly rubbed the bulge that was bursting through his trousers, then gently undid his zipper and prised his rock hard member out. This was my first time so close to a man's penis. It was breathtaking. The delicate veins and blood vessels running up the side contrasted with the brutal functionality of his circumcised head, it was so tactical that it would quiver and respond to my breath, but more than anything the smell drove me wild, it was the smell of submission and of addiction.

I gently parted my lips and took the tip of his cock into my mouth, there was a pleasant salty taste and a strange familiarity that still makes me feel like I was born to be a sissy. My tongue rolled around his shaft as I swallowed more of his member, I reached my limit and slowly backed my mouth off as rivers of spit and precum flowed out of my mouth. We continued in the fashion for maybe half a dozen more strokes when we heard footsteps approaching.

"Be quiet," the stranger growled as he grabbed the back of my hair. "This time we are finishing" he held my head in place and he rocked his hips back and forth, once the footsteps had disappeared past us he really took control. His cock was pounding into my throat and his balls were slapping at my chin, as he backed away I only had half a second to breathe in before he penetrated my mouth again. All pretense of discretion has disappeared, my eyes and nose were running and my mouth was a river of spit and virile male juices. A rough hand had clamped down over my throat, perfectly pinning my head in position to be face fucked. And even though I was doing my best to be quiet, a rhythmic burbling and slapping sound echoed around us. He had stopped even looking at me, my mouth was his tool to cum, and I was just a fuck toy for him.

My brain left my body and I became completely unaware of our surroundings. I could only focus on repeatedly swallowing this delicious cock that was ramming my mouth, and teasing my own less impressive cock with my free hand. After a few particularly violent thrusts he held my head down to the base of his dick, I desperately gasped down a mouth full of air as I felt his hips shudder and a hot salty load sprayed the inside of my throat. Instantly I was thrown away coughing and gasping for air, the stranger quickly wiped himself off and departed, while I remained, my face covered in cum and my hand down my pants. My tiny weak orgasm came shortly after.


Part 4- Isolation


The rest of my journey was less eventful, I just stayed in my seat and did my best to be inconspicuous, the stench of cock was deep in my throat and I was very aware of the gurgling I had made in the toilet. It was clear that my fellow passengers knew exactly what I had done in there, and the atmosphere was a little icy.

The stranger had the sense to sit further down the train, but my seat allocation and an overbearing conductor kept me close to the scene of my oral debasing. Now that the safety and relative freedom of the university campus were literally behind me I had a wider sense of social pressures bearing down on me, the stares and judgment of the other passengers were scratching the back of my head. Men who would have eyed me up and down were averting their gaze and muttering under their breath. I heard a woman whisper "pervert" under her breath, while her male partner nodded in agreement.

It was that nod that brought reality crashing back into my consciousness, what was I doing? Spending all day in panties with a sex toy up my ass? Eating a cum in a public shower? Getting face fucked on the train? This train was going to my hometown, these people would disembark and see my parents! My hometown wasn't large, and my reputation could be ruined before I even opened my bedroom door. What if everyone knew what a whore I was? What would they think? The threat of being ostracized loomed over me, but I just could not stop my brain from wandering further. Maybe men would flag me down and fuck me on their way home, maybe I could be a true cum pig and ride cocks all day. I wouldn't need a job, my daddies would take care of me, my parents would be disappointed, but they'd hear about my talented cock sucking skills and accept me for who I am, maybe they would see my slender frame and tiny cock and realize that I'm no man.

Maybe, maybe... maybe I was out of my mind, my cock addiction was clouding my judgement. I just had to make sure there was no cum on my face and get home in one piece. The train juddered to a stop and my discrete butt plug felt uncomfortably large. A large sense of dread swallowed me as I disembarked, there was an almost inevitable sense that my carefully curated future was over. For all my time spent grinding on men, and obsessing over getting fucked I had worked hard on my course, and I did want to have an independent career after university. I just had to pray that I had been discreet enough. My pantie filled suitcase seemed to weigh a couple of tons and my feet slapped meekly on the concrete. Nevertheless I put my head down and walked toward the exit.

LiveSteam
LiveSteam
15 Followers
12