This is my first time writing a sex story! Had a lot of fun doing it and I'll write a second chapter if this one gets a good reception, so comment and leave a like!!
I had never been so embarrassed in my life. The woman in front of me looked at me with disgust that burgeoned on fear. Seconds prior, I was knocking on her door and ringing her doorbell expecting for a man to answer.
This man was Anthony, or at least that's the name he'd given me when I asked. We'd met online a couple weeks ago on a gay dating site.
For a few months now I've been exploring my feminine side. Actually, I haven't been "exploring" so much as diving right in. After a bad breakup I had last year with my ex girlfriend I went on a self exploration binge and discovered I was pansexual.
Shortly after coming out, I began to discover more and more about myself, such as how fascinated I was by makeup and how much I really admired women's clothing.
One day, while I was working at my part time job at a clothing store, I found myself thinking out loud as I examined an amazing outfit on a mannequin in the women’s department.
It was a simple, yet elegant, white dress that fell to about the middle of the thigh. It was split on the right side so that the leg poked out, showing off a lot of the thigh, but not too much. Over it lay a navy colored cardigan that was cropped to just below where the woman’s breasts would be. A silky, navy blue sash was tied lightly over the hips and a pearly white purse was slung over one of the mannequins shoulders.
I was hypnotized by its elegance. As I gazed at the lifeless model, my mind drifted and my imagination conjured up the image of the woman who would wear it. She would be gorgeous- absolutely stunning.
Her dark hair would drift gracefully behind her and every step she took would breath new beauty into the eyes of both men and women who ogled her and who drank in as much of her magnificence as they could until it threatened to drown them.
The only thing that would speak louder than her beauty would be the confidence with which she presented it.
She knew exactly who she was and loved every bit of it.
The woman I imagined was the complete opposite of me- a lonely, self-loathing man (a boy really) who could hardly be called masculine no matter how much he tried to emulate the sort of toxic masculinity he hated so much- the type of toxic masculinity that seemed to work so well for other men.
The confidence she exuded is what I admired the most. My confidence shone about as brightly as my future- which isn’t saying much given that I was currently a part time retail grunt who was spectacularly failing all of his college courses.
I sighed as my mind drifted. “I wish I could wear womens’ clothes,” I said without thinking.
Suddenly, a voice from behind me broke me out of my reverie.
“Why don’t you?” I jumped at the sound and spun around to see my coworker, Casie.
We were wearing the same uniform, but the attitude with which she wore it was completely different from mine.
All of the buttons on her polo were undone, and the cuffs on her khakis were rolled up to expose chain necklaces and ankle bracelets. Similar jewelry adorned her wrists as well as her ears in the form of piercings. These perfectly complemented her hair which was platinum blonde and shaven on one side.
Her look was essentially that of your quintessential punk rock feminist. This threw off most of the men around her, including the customers and our coworkers. I admired it, though.
She wasn’t bound by any gendered stereotypes, and through her style and accessorization, she screamed in the face of all that tried to define her with a confidence I knew I could never muster.
I gave Casie a puzzled look after her comment, so she repeated it.
“Why don’t you wear women’s clothes? It’s just fabric.” She said it like it was nothing and simply shrugged before walking off, leaving me to my thoughts.
Huh, I thought as I stood dumbfounded in the isle. She’s right. Why the hell don’t I??
And so it began.
It started out small. A pair of womens’ jeans here, a tight fitting t-shirt there- all things that were still somewhat passable as something a man would wear. It’s not like I was wearing any of this in public- I wouldn’t dare- but I was still hesitant. Then I just went deeper.
After that, crop tops, skirts, tight shorts and dresses began to line the back of my closet. Pretty soon I was buying several new pieces of women’s clothing with each paycheck. Each item was more provocative than the last.
In the meantime, I spent my nights browsing youtube for makeup tutorials and practicing with a small makeup kit I’d bought for myself. I found it amazing how much I could change my appearance. It truly was an art form.
I also taught myself to shave my body properly, although I didn’t have that much hair to begin with.
One of the most intimidating parts of my exploration was wearing a wig. I had no idea where to start, and after seeing so many infamous celebrity wig malfunctions, I was afraid of even trying.
I eventually gave in and bought a decent wig online. It was a little bit pricey, but I didn’t want to go cheap. Plus, this one had such beautiful curls. Since I was half black and had curly, afro-like hair myself, I wanted something that would look natural on me.
I was absolutely shocked the first time I tried on the wig with full makeup and outfit on and looked in the mirror. It was like I was a completely different person. The woman I saw in the mirror looked stunning and confident- and I loved her.
I was starting to really like this.
Then there was the more… adult side of my exploration. Gay porn had never really interested me while I identified as straight, even though I always found the men very attractive. It still didn’t capture me like I expected it to, however, now that I openly identified as pansexual.
Something else did capture my attention, though.
Sissy porn.
Everything from hypnosis, to captions, to compilations and PMVs. Something about it felt different to me and turned me on like nothing ever had. Something about the dominant men that forced the sissies into submission, the humiliation they were subjected to and the pure ecstasy they seemed to feel from said humiliation.
I never imagined myself from the perspective of the man; I always imagined myself being in the sissy’s shoes. They seemed to be so happy, to have exactly what I wanted. Even though they were humiliated, made to submit, they seemed so confident in who they were. Even in such a submissive position, that confidence gave them a power that I had never felt, only witnessed.
This urged me further down the path I was following.
It wasn’t long before I bought my first toy. Just a small dildo, maybe four inches long. It wasn’t “big” by any standard, but I mean it when I say it hurt the first time I used it. I hadn’t prepared at all for my first time inserting something into my ass. Hell, I think I just used some shampoo as lube (let me tell ya, that burns!).
I didn’t give up, though. With the help of the internet, I taught myself how to prepare to have things going inside me. I learned how to douche, what lubes to use, and how to use plugs to stretch myself out.
Pretty soon I was riding dildos like a pro! The measly four inches of my first toy was nothing to me now. I quickly traded it for nine inch monsters of varying widths. The pain turned to pleasure and pretty soon I was riding those fake cocks like I needed it to live, pounding my prostate like it stole from me.
There was only one problem.
I couldn’t cum.
No matter how hard I tried, I could never achieve that fabled “sissygasm” I’d heard so much about online. I would come so close- almost to the point of ecstasy- but never crested that hill.
AND I HATED IT.
I had never been so frustrated in my life, sexually or otherwise.
I came to a decision: I needed the real thing.
So to the online forums I went! During my deep-dive into the wonderful world of sissy porn, I discovered several sites for men to meet and hook up with sissies near them. I had never dared sign up, though…
Until now.
I signed up on a website called Sissy Finder. It asked for all your standard dating site info, like what you were into, what you were looking for. Obviously I said that I was a sissy looking to hook up with a dominant man.
Just typing that out made me so excited and nervous at the same time. I hardly knew what to do with myself.
I found a strange and titillating ecstaticness in carving out this persona that was becoming more and more real by the minute.
Eventually, it asked me for my “sissy name” and I stopped. I’d never thought of this.
I’d always just gone by my real name, Julian. But if I were creating a new identity for myself, I should go by a different name, right?
Obviously, my first thought was to go as Julie, but it scared me how close it was to my real name. What if someone saw me, heard the name, and connected the dots?
No. That could never be allowed to happen.
I put my mind to work thinking of another name until I finally settled on Sasha. I don’t know why I chose that name, but it just felt… right. Graceful, refined and simple. Sasha.
And so, with the name decided, I clicked ‘submit’ and created my account.
It wasn’t long before I met Anthony.
To be honest he wasn’t anything special. In fact, I think the only reason he stood out was because he was the first person to message me.
He was thirty years old, so about a decade older than me. He was white, blonde and around average height and build.
I can’t remember what we talked about before he asked me to come over, something about his office job that he hated.
To be honest, I couldn’t care less. I only wanted one thing.
He sent me a picture one night and there it was: six inches, clean, cut and rock hard.
I spent what felt like hours just staring at and admiring his cock. My mouth began to water just looking at it.
It would hardly be the biggest thing to ever be in me, but it would be real.
My first real dick!
I was the last person to be complaining about size anyways. My own five inches of pathetic penis was nothing to get excited over.
It wasn’t long before we really got to talking and began exchanging pictures. I loved to tease him with photos of all my different outfits.
Before I knew it, he was inviting me to come over and my stomach was doing front flips from the thought of finally getting what I’d desired for so long.
I made a plan to visit him that night. He messaged me his address and as soon as I got off work, I rushed home to get ready.
My mind raced as I tried to pick out the best outfit. I finally settled on a long sleeve, white, fishnet crop top and light blue denim booty shorts. These were my favorite shorts. They somehow made my butt look HUGE and like I had all of it hanging out.
I put on a pair of black striped thigh high socks with a matching pair of converse shoes.
With my outfit ready, I was quick to apply my makeup. I’d had so much practice by that point that it was finished in no time at all.
Then followed the wig which I had already washed and styled. It came with its own wig cap, so I didn’t need to worry about glueing it down or anything. I just slipped in on.
Once everything was complete, I looked in the mirror and froze.
There she was again. That beautiful, confident woman stared back at me from the mirror. I watched and felt as a smile crept onto her lips.
This was me.
For once, I finally resembled the person I wanted to be.
Shaking myself from my reverie, I looked around to double check that everything was ready.
“Oh!” I exclaimed. There was just one thing I’d forgotten.
I scrambled to my closet and rummaged around till I found it. I stood up and smiled, bringing with me a pink, plastic chastity device.
I had bought it just recently and felt a thrill every time I put it on. I quickly undid the lock on it and pulled my soft, little penis out of my shorts. I slid it carefully into the device. Thankfully I was just small enough when soft to fit inside.
I snapped it shut and voila! Perfectly locked, just like a sissy should be.
Once I was finally ready, I went to my bedroom door and peeked outside. This was where the tricky part came in.
My parents had no idea I crossdressed in my free time. I had never even left my room with so much as a smidge of makeup on.
They also happened to be the only people that I hadn’t come out to about being pansexual.
To be honest, I was afraid to. My dad was your stereotypical “man’s man”. The perfect image of hypermasculinity. And he wanted nothing more than for me to be just like him.
He had raised me to be just like him. All throughout my childhood, I was in and out of football teams, boy scouts, and boxing gyms because of him and his various attempts to make me “man up”.
Whenever I expressed dislike in something, he would just move on to the next thing to force on me. I was almost shipped off to military school a few times, but was saved by my godsend of a mom.
In fact, my mom was the only reason I was allowed to stay in their house. At this point in my life, my dad had all but given up and wanted nothing to do with me. Fortunately, my mom stopped him from kicking me out, but that didn’t stop him from trying to make my life as difficult as he could.
Whether it was raising my rent, forbidding me from bringing friends over, or constantly berating me for the slightest transgressions, he never ran out of ways to punish me for not being the son he wanted.
Both of my parents were in their room watching TV, so escaping unseen shouldn’t have been that difficult. Fearing the repercussions and wanting to air on the safe side, however, I ran back in my room and pulled on a pair of basketball shorts and a large jacket over my sissy outfit.
I pulled the hood over my head and left.
One nervous drive later and soon I was standing before a woman glaring at me with an expression that filled me with equal parts fear and shame. I felt as though my stomach would drop through the floor.
I had knocked on her door, Apartment 103, expecting Anthony to answer, but instead was greeted by her. At first she was curious and kind, asking who I was. But the moment I opened my mouth and she heard the deepness of my voice, that changed.
No one named Anthony had ever lived there, and none of her neighbors went by that name.
I don’t know if her expression conveyed fear, disgust, anger or some morose mixture of all three. But I knew one thing for sure: she didn’t want me there.
“I think you should go,” she said.
I couldn’t have agreed more.
The brisk walk back to my car was as tear filled as it was shameful. I struggle to remember a time when I had been more embarrassed than I was in that moment. I walked with my arms crossed and my head down.
Trying my best to see through my tears, I logged onto the dating site on my phone and messaged Anthony.
‘Fake address. Nice. I love being lied to.’
A second later he was blocked.
Having finally reached my car, I started searching my pockets for my key.
“You look troubled.”
I nearly jumped out of my skin when I heard the voice from behind me. I wheeled around to see a strange man standing on the other side of the street. He was wearing a long, black trench coat with his hands in the pockets. The hood was pulled over his head so that his face was almost completely obscured.
I couldn’t see the look in his eyes, but I could see his smile. Creepy, hungry and malicious, illuminated by the overhead street lamp.
Needless to say, it wasn’t a smile I ever wanted someone to look at me with.
Oh hell no, I thought. I tried to pull my keys out, but they got caught in the tight pocket of my shorts. I yanked as hard as I could, only to have the keys fly out of my hand and onto the ground.
Of all times for me to be a klutz, this had to be the worst!
My blood ran cold as I heard footsteps start to approach me. My panic rose with every dull crunch of the gravel.
“No, no. Don’t be afraid,” He said, his voice much closer this time. “I only need you for but a moment.”
No the fuck you don’t! I thought. There was no way I was about to be the next murder story on the news. At the very least, I didn’t want the world to find out about my crossdressing like this.
I quickly bent down and grabbed the keys. Wasting no time, I picked out the car key, inserted it into the lock and flung the door open…
But it was too late.
I felt a hand on my shoulder. It was soft, yet strong, and with that strength, it whirled me around to come face to face with the stranger.
He was closer than I expected. Our faces were mere inches apart. His eyes were the first thing I saw. It was dark, so I couldn’t make them out completely, but I could’ve sworn they were glowing. There was a gentle and mysterious glint in them that drew me in with a deadly curiosity.
His breath was the second thing I noticed. Far be it from me to take any sort of joy in smelling another person’s breath. It was an experience I typically tried to avoid.
This man was different, however. His breath carried a scent with it that I can only describe as inexplicably sweet. Something about it lured me in and threatened to beset me with an insatiable craving.
As I was hypnotized by this strange, frightening man, I almost didn’t notice that my jacket and top had been lifted up. I snapped myself out of my stupor, but it was too late. He brought his other hand up and pressed the palm hard against my abdomen.
For a moment, I felt nothing but his soft skin on mine and the pressure of his abnormally strong hand. Then, as though someone had jabbed me with a hot iron, it began to burn.
The pain was indescribable. It was more excruciating than anything I’d felt before. I opened my mouth to scream, but nothing but a pathetic whimper escaped.
My eyes began to roll back as my entire body cringed and contorted. Then, a second later, it vanished, leaving only an echo of pain behind.
I gasped as I finally regained my senses. Now back in control of my body, I brought my hands up and pushed the man back as hard as I could. As he stumbled backward into the street, I leapt into my car, started the ignition and sped off.
My heart, riddled with fear, pounded violently in my chest. I had no idea what just happened, but all that mattered was that it was over. I took what felt like my first breath in forever as I drove away and ignored every stop sign on my way home.
I threw myself onto my bed. I felt drained.
Every ounce of energy and anticipation had long since fled my body, leaving only exhaustion and bad memories.
I was so ready to have my cherry popped only to have my hopes brutally dashed right before my eyes! Not to mention I was pretty sure I had almost been killed as well.
My mind drifted as I thought back to the strange man on the street. Something was weird about him, and I don’t mean your typical, rapey kind of weird. Something else about him caught my attention but I couldn’t place my finger on it.
My hand subconsciously drifted to my stomach on the spot where it felt like he burned me. I gasped and quickly lifted up my shirt and looked down, only to sigh in relief.
He hadn’t left a mark.
Good, that would’ve been hard to explain.
I let out another breath. To be honest, I just wanted to move on and forget this all happened. I stripped off my clothes until all I had on was my skimpy sissy outfit.
As I laid back down, my mind wandered to where it always does: the gutter. My head was quickly filled with thoughts of what could’ve been.
What if Anthony had really answered the door? What would he have done to me? How good would it have felt?
Fantasy after fantasy came to mind and I could feel myself getting hotter by the minute.
I reached down into my shorts and pulled out my limp dick while I grabbed the lube off my bedside table with my other hand.
I poured just enough into my palm and began to stroke. Slowly, then faster, pulling with a gentle yet firm grip in familiar and practiced motions.
Before long, I was rock hard.
I stroked my little dick faster and faster, running along the length of the shaft all the way to the tip.
I would stop for just a moment to focus on the tip and spread the copious amounts of precum that leaked out, then go back to stroking. My hips rocked gently along to the steady rhythm.
After a while, I noticed that something was wrong.
I wasn’t cumming.
Not only was I not cumming, but I wasn’t even getting close.
This was strange. I could usually make myself cum in almost no time at all, but here I was, rock hard, horny as hell, and nothing to show for it.
It was strange, and extremely frustrating.
My strokes got more and more aggressive.
I wanted- no, I NEEDED to cum.
Minutes passed by and still nothing. I was still hard, my cock leaking a constant stream of precum. I growled in frustration.
“What the hell do you think you’re doing?!”
I nearly leapt out of my skin when I heard the voice from the other side of my room.
I whipped my head around, flinging my hair into my face, to see my dad standing in the doorway. He was staring at me with an angry and bewildered look in his face.
A thousand thoughts rushed through my mind all at once as I put together what was happening. There I was, dressed head to toe in the sluttiest women’s clothes I could find, complete with makeup and a wig, my small hard dick in my hand, in front of my insanely misogynistic.
“D-dad, what are you-?”
Before I could even get five words out, my dad was across the room with his hand on my neck. He yanked me toward him with more force than I could resist.
He looked me up and down.
I could feel his hot breath on my face as he growled, “So this is what you’ve been doing behind my back.”
His grip on my neck was tight and kept me in place so that the only thing I could look at was his furious eyes.
I was trembling with fear. I had never seen him this angry before. There was no telling what he was about to do.
“P-please wait, it’s not what you-”
Before I could finish, I felt more pressure on my neck as he pushed down and my weak legs buckled under the force. A second later, I was on my knees.
And that’s when I noticed the bulge in his pants.
It was huge, like a snake hiding in his pants. It was thick, maybe only a little thinner than my wrist, and it extended almost to his mid-thigh.
I heard a rustling sound above me and watched as he unbuckled his belt with vigorous fervor. Once it came off, it was quickly followed by the button and zipper on his pants.
My dad slowly pulled down his jeans that I had watched get tighter as the monster inside grew stiff.
As soon as I realized what was going on, his massive cock was springing from its confines to smack aside the face.
My eyes grew wide as I stared at my father’s member. It looked even bigger outside the pants. The thing had to be at least 8 inches, and thick as hell.
I felt his heavy hand on the back of my head start to push me toward it. I looked up at him with begging eyes, searching for some sign of mercy.
But I saw nothing of the sort, just a hunger that he would satisfy by whatever means.
With my head in one hand and his cock in the other, he placed the tip on my whimpering lips.
He smiled as he smeared the precum on my lips like he was applying chapstick. Once it coated my already painted lips, he positioned himself, and started pressing and pressing.
I was helpless to resist and the swollen head popped into my gaping mouth.
I gasped around his cock.
The first thing I noticed was the taste. Salty with a hint of sweetness. I tasted almost exactly the way he smelled with his nearly overwhelming musk. But this flavor was gentler somehow, almost pleasing.
My tongue retreated at first, but then came out reluctantly to explore the soft and squishy feel of his head.
I didn’t have much time to ponder that thought, however, as he began to apply more pressure and push his dick ever deeper into my mouth.
As he went farther in, my tongue rubbed along every meaty inch, taking in the alluring salty-sweet taste and the smooth almost rubbery texture of his skin.
I suddenly felt something strange, and I don’t just mean the feeling of my dad’s cock in my mouth. It was the feeling I had so desperately been chasing earlier.
Pleasure.
I could feel it rising inside me like a creeping tidal wave washing down from the top of my spine to the tip of my still erect clitty.
My mind was reeling. NO. No way. There was no way I could be enjoying being raped by my own dad!
I started freaking out. I couldn’t move my head much on account of the massive incestual cock making its way toward my throat, so I reached down with one of my hands to confirm my fears.
And sure enough, on the ground beneath me was a growing pool of thick, sticky precum. I tentatively touched the head of my penis and felt it streaming out as if my dad had turned on a faucet.
I grunted in surprise as I felt my father’s rod hit the back of my throat. By now, it was dripping with my saliva and a few drops even fell to land on my chest. I could see that there were at least three inches of hard meat to go.
He paused there and I looked up at him with pleading eyes. The tears streaming down my face caused my makeup to run.
I must’ve looked like a pitiful sight because the man looked back at me with a malicious smile full of cruel pleasure.
At that moment, I knew he would not relent.
With one last aggressive thrust, he shoved the last few inches into my mouth and I felt his huge head penetrate and slide down my waiting throat, blocking my airway.
I squeezed my eyes shut, waiting for my gag reflex to kick in at full force and reject his cock along with whatever I’d had for lunch…
But nothing happened.
Although saliva was still pouring out of my mouth, I didn’t throw up, nor did I start choking. I still could hardly breathe around his cock, but this was hardly the feeling I was expecting.
I watched as he threw his head back in ecstasy. I could feel his cock twitching in the depths of my throat as he let out a loud, guttural groan.
“Fuck,” he said. “This throat’s even better than your mom’s.”
Is it weird that I felt a tinge of pride when he said that?... Maybe a little.
My father held my head in place for a moment, savoring the feeling of being buried to the hilt in his son’s throat.
Then, slowly, he began to pull back, letting his manhood slide out of my airway and back along my dripping tongue.
He did this until just the tip remained, cupped by my painted lips, then slammed it back in. His cock forced itself relentlessly back into my throat like it was trying to reach my esophagus.
“Mmrmph!” I tried to yell in protest, but my mouth was a little full at the moment.
This became a pattern as repeated the motion, sliding it out ever so slow, just ram it back in. He went slowly at first, but quickly sped it up to a steady rhythm.
My father was turning my throat into his own personal fucktoy.
And my body was loving every second of it.
Despite how horrifying the concept was to me emotionally, my physical response was undeniable.
I was coming closer to an orgasm than I had while I was stroking myself!
My stiff dicklet was still dribbling out precum, begging for release. The puddle underneath had grown larger and copious amounts had stuck to my legs, soaking my thighs.
My throat was getting more and more used to the feeling of his giant cock penetrating it.
After a moment, my body started to move on its own and before I knew it, I was bobbing my head to the rhythm of his thrusts.
I would open wider and loosen my jaw to let him in when he pressed forward, then pucker my lips and brush my tongue over the head as he pulled out.
Fuck it, I was enjoying this.
I started fantasizing about what would happen next. When was he going to climax?
My body quivered in anticipation at the thought of tasting his savory cum as it shot out onto my tongue.
I was getting lost in the ecstasy, but I quickly tried to shake myself from those thoughts.
This was my dad we were talking about- how could I think that??
Just as I was starting to regain my senses, I noticed that his thrusts were starting to get more and more forceful.
His face was contorted in pure pleasure, and before I could react, he grabbed the back of my head and went in for one last, great thrust.
His cock spasmed and I could feel his balls twitching on my drool covered chin.
Most of all, though, I felt something hot and thick pelt the back of my throat and slide lazily down.
I knew what this was, but didn’t want to admit it.
My own dad was cumming in his son’s throat.
His dick was so deep in that I had no choice but to swallow or risk drowning in his cum, and that wasn’t exactly the way I wanted to go out.
Seconds passed as streams and streams of my father’s cum poured into my mouth down the very base of my tongue.
It seemed endless, and I remember thinking that there was no way anyone could cum for this long!
Sure enough, however, his orgasm carried on and he continued to deposit thick spurts of cum into my stomach for at least a full minute.
Finally, after what seemed like forever, he pulled out and took a step back.
I fell back, exhausted and gasping against my bed. My mind was reeling from what just happened. It felt like it was in a fog.
I looked up and saw his cock. It was a little limp now, but still impressively large, and it was completely covered in my saliva and his cum. I was almost mesmerized by the way the fluids mixed and slid like molasses down to the bulbous tip, then fell onto the floor, staying connected for just a moment by a long, sticky strand.
My eyes turned up once more to his face, scared that he might still be angry…
But his expression was blank, almost sleepy. In fact, he wasn’t even looking at me. Instead, he just stared straight ahead.
Confused, but hesitant, I muttered, “Dad?” to try and get his attention.
But he gave no response. He stood as still as a statue for what seemed like minutes, then, without warning, turned on his heels and walked out of my room without a word, shutting the door behind him.
I was still gasping for air as I stared bewildered at the door.
What the hell just happened??
Well, I mean, I just got raped by my dad, obviously. But I had so many questions!
Why did he act the way he did at the end? Why did he do that to me in the first place? My dad was a dick, but he wasn’t a rapist, and he certainly wasn’t gay.
Most of all, though, I found myself wondering why I enjoyed the experience as much as I did…
These thoughts and more spun around my dizzying mind. It wasn’t long before my fatigue caught up to me and the walls of my consciousness began to close in. A minute later, I passed out right there on my bedroom floor, still dressed as the sissy whore I didn’t know I was becoming.