Little Red's Big Night

I had spent weeks perfecting the look, and tonight, it was finally paying off. Halloween night. The one night it's publicly acceptable to dress like a total slut, whether you're a man or a woman. And I was dressed like a slutty girl at a Halloween party with my friends. A black corset trimmed with lace cinched my narrow waist impossibly tight, and also pushed my flat chest into the illusion of delicate curves. The red dress that covered it flared out in layers the bottom layer ruffled white tulle that stopped about mid-thigh, barely covering the black lace panties I had on underneath. White thigh-high stockings topped with delicate lace clung to my pale and slender shaved legs. A scarlet hooded cape draped over shoulders that I had practiced slumping just right to seem more dainty, and an auburn wig clung to my head, styled to perfection into curls that spilled over my shoulders beneath my hood. And to top it off, I had bought a wicker basket prop, which I was now using to store my phone and a few other belongings since all the cookies I had brought were gone.

I was twenty-four, skinny as a twig, with a pretty and feminine face that I had softened even more by carefully applying my makeup. Rosy cheeks, painted lips that matched my red hood, and just enough eyeliner to make my blue eyes look big and doe-like.

I had been building up to this for weeks. Months. Years, really, almost always dressing up like a girl in my alone time, and dreaming of being able to present myself like that in my world. But, finally, tonight was the night.

I had carefully curated my costume, scrolling Amazon and Google for hours on end, reading reviews, consulting the size charts, wanting everything to be perfect for my big night. Even though I had been into crossdressing for years, practicing a lot in private, I had never been able to summon up the courage to go out in public like that. But that had all changed when one of my friends had jokingly said, "Alex could totally dress up like a girl!" And I had replied "Challenge accepted!" Maybe a little too eagerly, but I had said it. And tonight, I was going through with it.

I was a man, undeniably so beneath all the makeup, the lace and satin and tulle. But tonight, I looked like a girl. A girl who'd stumbled into a fairy tale. And all of the alcohol I had

consumed definitely helped with the illusion, loosening my body as I swayed through the crowded party, accepting compliments from strangers who couldn't tell and from friends who absolutely could. All the while I was actually searching for a certain lady friend. This friend had curly purple hair and glasses and a total milf body, big, round tits, a nice round ass that she alemways displayed in tight leggings, and she was a really good friend who I was hoping to flirt with a little tonight, or maybe finally try to make my move and get out of the friend-zone.

"Alex, you look ridiculous! And totally hot," my friend Britney had laughed out loud earlier, snapping photos of me posing with my wicker basket prop. I had loved it. Feeling seen as the girl I sometimes fantasized about being, if only for a night.

"Where's Robin?" I shouted to Britney, the music of the party bumping so loud that our cheeks were touching and we could still barely hear each other.

"Um, I saw her in the kitchen like ten minutes ago," she shouted back.

"Derek?" I asked, sounding more like a plea.

"No," said Britney, "I'm sorry!"

"It's okay!" I shouted, even more loudly, "they've got to be here somewhere!" I kissed her on the cheek, gave her a wink as I raised my drink in the air to avoid spilling, and dived back into the crowd.

The shots of tequila and the vodka cranberries had kept coming, but still no sign of Robin, and somewhere around midnight the room began to spin. I stumbled around for what felt like forever looking for my friends, but having no luck. I was feeling a bit sweaty and claustrophobic, so I stumbled out onto the front porch, gasping in the cool October air, and still searching for the familiar faces of my ride home. But the spot where Derek's car had been parked was empty. The driveway was empty. Their car, the one they'd promised to take me home in, was gone.

"Fucking seriously?" I slurred, immediately fumbling in my basket for my phone. Three texts, all from an hour ago. Sorry, man, had to go! You'll have to catch an Uber!" And just then, my phone's battery died as I was staring at the screen.

I was currently living with my grandmother, who's cottage was about four miles away. On the opposite side of town. And walking that far? In this outfit? In these heels? Well, that was going to take forever. But, there was always the shortcut. Through the woods. At night. I had walked that trail hundreds of times in the daylight, using the narrow dirt trail that wound through the dense trees to shave off about half the distance. But at night? Drunk and in a slutty, girly costume? It seemed less appealing, somehow. But the alternative was sleeping at a stranger's house, so... I adjusted my hood and cape, pulled my white stockings up where they were starting to sag, gripped my nearly empty basket, and started walking.

The woods were hitting differently at 1 AM. The bright full moon hung fat and yellow between the skeletal branches of the towering trees, casting long shadows and making it seem as if the branches were reaching out for me. Every snap of a twig under my heels made me flinch. The black satin corset suddenly felt too tight, my lace panties too scant and revealing. The whole costume seemed ridiculous now in the chill night air. I was a scrawny, pathetic boy in girl's clothes, alone in the dark woods, and my warm, drunken joy was rapidly fading into cold sobriety.

I was muttering curses at my friends, something along the lines of "assholes... fucking leaving me... I hope their car breaks down," when I heard something behind me, and I froze. A low, menacing growl came from somewhere in the darkness, followed by heavy, ragged breathing. "H-hello?" I said, in not much more than a whisper. My throat suddenly felt very dry as the weak sounds tumbled past my crimson lips. And then, as the full moon appeared then from behind dark gray clouds, a booming howl broke the silence, and goosebumps broke out all over my smooth, sissy body. Whatever it was, I could hear it coming toward me, twigs and branches snapping loudly as the thing moved through the shadows like smoke in the wind. I stood there, still as a statue, but there was no stilling my racing heart as it beat rapidly against the stays of my corset.

And then the thing emerged from the shadows, and it was like a nightmare given flesh. Seven, maybe eight feet tall, huge rippling muscles bulged beneath it's thick, gray fur, a long snout protruded from the front of it's big head, large and furry pointed ears were sticking up from the top of it's head, and eyes that glowed golden in the moonlight were fixed on me with a predatory hunger. It's lips then pulled back in a wolfish snarl, revealing huge teeth like daggers.

It was a werewolf. A real life, flesh and blood werewolf, bigger than anything I had ever seen, and it was now blocking the path before me.

I backed away slowly, hands raised, basket shaking, speechless and unable to believe my eyes. "Oh, m-my... what big... big eyes you have," I said weakly. The werewolf began to approach me, eyes still fixed on me menacingly, and still baring it's very large and sharp teeth with that low, deep growl rumbling in it's throat. "N-nice wolf," I whispered, voice cracking and sounding high and girlish. "G-good wolf..."

And then my heel caught on a thick tree root and I went down hard, back hitting the cold, hard ground and my skirt flipping up, black lace panties totally exposed to the frigid night air. I scrambled backward, heels digging into the dirt, and the beast was on me in seconds. It's massive paws were tipped with huge claws and they closed around my wrist and then lifted me up like a rag doll, my heeled feet dangling helplessly off the ground. And then I gasped loudly as the beast spun quickly, hauling me up against the rough trunk of a thick tree and pinning me there with one massive, furry paw. And then the other paw began to roam.

It started to grope my girly ass, squeezing my small, tight cheeks through the lace, then slid around to grip my narrow hips, all the while sniffing and snorting loudly. The huge beast pressed closer, and then I felt it. Hot, hard, and enormous, it's huge werewolf cock was now pressing firmly against my stomach through the thin flimsy costume that was my only protection. "Oh, god," I squeaked, terror, and something else, welling up inside of me. "Please don't kill me, please don't..."

But the werewolf didn't kill me. It sat me roughly on the ground and began to sniff me some more, and again groping and grabbing with it's large clawed paws, poking and prodding, inspecting my trembling body. And much to my surprise, it crouched low before me, lifted my skirt with an upturned claw and began to roughly flick my sissy clit with another claw, almost seeming amused. My clitty was now rock hard and throbbing, straining tight against my lacy black panties and totally giving myself away....

I gasped loudly as the beast then rose up, and it's wet nose was suddenly pressed against my slender neck, inhaling deeply. It growled again, low and rumbling in it's throat, and I realized with a sickening lurch that it was smelling my fear. And my arousal. Sweat beaded on my skin as those massive paws again roamed over my entire body, groping my smooth chest, my hips, my little ass and skinny legs. I could feel every bit of it through the thin, cheap fabric of my costume. I let out a high-pitched squeak as it ran it's claws down up my smooth thighs, almost scratching, and then pushing my skirt up to my waist, but I just stood there frozen, completely exposed and helpless. My black lace panties tented pathetically, my clitty so hard and dribbling precum despite my terror. Despite the danger. BECAUSE of the danger. The werewolf looked down at it, then at me, and I saw intelligence in those yellow eyes. A hint of mockery, even. It knew what I was, and it was going to treat me as such.

The beast then dropped to it's haunches, and I thought for a wild moment it might bite me right then and there and end it quickly. Instead, it hooked the front of my panties with a big claw and pulled them down, letting my small sissy clit spring free, pathetic and still leaking. And I could have swore that this monster smirked at me before once again rising to it's full height. "Please...." I said again weakly, but I wasn't even sure what I was begging for anymore.

Towering over me, the monster grabbed the back of my head, squeezing my scarlet hood and also some of my hair in it's monstrous grip. It pushed down hard, forcing me to my knees in the cold dirt and dead leaves. Still held in it's powerful grip and unable to move my head, my eyes swiveled upward, and the beast's cock was now right in front of my face. My eyes went wide with shock. Massive, bright red and veined with a pointed tip and a thick, tapering shaft, it ended in a big canine knot that was rapidly getting bigger.

It pushed my head back and slapped it's fat dick against my crimson lips, smearing precum across my face. And then, maybe because I was in shock, or maybe because of the endless fantasies I had had about being a girl, being desired when dressed like this, being claimed and used, I truly don't know, I closed my eyes and opened my mouth wide. Because honestly, what else could I do?

As the werewolf's huge red cock entered my mouth, I tasted sweat and musk on my tongue, and something else. Something primal and wild. Then, unexpectedly, it's powerful hips jerked forward, not gently, not kindly, and the size of it's huge cock forced my jaw wide. Immediately I gagged and tears were springing to my eyes. My mascara began to run down my cheeks in black streaks as it forced it's fat cock completely down my throat, and the swollen knot pressed hard against my lips, too big to fit. It smashed it's knot against my lips repeatedly and I moaned around it helplessly as the beast fucked my mouth with rough, jerking motions. My hands came up instinctively, pushing against it's big furry thighs, but it was like trying to move a mountain. I was just a skinny boy in a girly costume, and this thing was using me like a toy. My little clitty swung uselessly between my legs, untouched but dripping steadily onto the forest floor and betraying my arousal more with every drop.

The werewolf finally pulled it's dick out of my throat with a wet plop, leaving me sputtering and gasping, spit trailing from my lips to the pointed tip of that monstrous red cock. But I quickly realized that it wasn't finished with me. Again like a lightning flash, it grabbed my arm and spun me around, shoving me face-first against the rough bark of the big tree. My hood fell over my eyes so I couldn't see anything, and I felt my skirt being pushed up and those huge paws on my hips again, moving and positioning me. My black panties were visible now and I felt the creature hook his claw around the waistband and pull them down slightly, just under my small round asscheeks. The corset felt unbelievably tight now like it was suffocating me, and my skirt was still bunched around my waist as I was held against the ancient tree trunk by the monstous creature. And I couldn't help but to laugh at myself then, at the thought of what was happening, mentally picturing myself before this enormous, hairy monster, my pale ass completely exposed to it in the bright moonlight.

"Wait," I whimpered, quickly coming back to the reality of what was about to happen. "Wait, no! It's too big, it's--"

But the werewolf didn't wait.

It's mighty hips jolted forward and I screamed into the tree bark, and my girly scream faded away unheard into the darkness. It hurt so much, like it was splitting me open, my saliva on it's impressive length acting as a poor lubricant. But the beast was relentless, working it's cock into my tight sissy asshole with short, brutal thrusts, not caring that I was sobbing, not caring that I was a drunk, pathetic sissy boy who'd just wanted to feel cute and pretty for one night. It only cared that I was warm, and tight, and his.

Inch by inch, it claimed me. My fake pointed nails scrabbled at the bark of the tree, and a few of them popped off and bounced away into the darkness. My skinny body was shaking, my little sissy clitty bouncing uselessly with each hammering thrust. And then I was aware of that massive knot repeatedly smashing against my tight rim, and I realized with horror what was coming next. It was going to knot me. Lock us together while it bred me like a bitch.

The werewolf started to fuck me in earnest--long, deep strokes that made me go cross-eyed, and my tongue was hanging dumbly from my mouth. But now the pain was beginning to blur, and then fade, shifting into something else. Every thrust rubbed hard against my prostate, and pressing that button of pure ecstacy made my sissy clitty leak even more, and my legs started to tremble. The beast was holding my hips so hard I could feel them bruising, but it didn't care as it pounded into my ass. I was just a little sissy cock sleeve to be used for it's pleasure. And at that point, I started pushing back, completely lost in sensations of pain and of pleasure. It seemed natural, automatic, and I just couldn't help myself.

And then with the hardest thrust yet, the beast's huge knot caught againt my tight ring, and with an incredible amount of pain and pressure, my tight little asshole opened up and swallowed that gigantic red knot, and suddenly little stars were popping before my eyes. "Ohhhhhh, my god!" I screamed and moaned, over and over, voice high and breathy. "Ohhhhhh god, ohhhhhh fuck... fuck, fuck, fuck..." I cried, gasping for air. I was being taken like a real woman. Not pretending, not just dressing up--actually being fucked, claimed, used for pleasure by something much bigger and stronger than myself. And the realization sent me spiraling.

The werewolf's thrusts became more erratic, savage. It was close. I could feel it swelling even more inside me, the knot growing until it was like a softball, pressing, stretching me impossibly wide as it locked into place. The beast threw back it's head, snout pointing upward and howled at the moon again, a long, piercing note that echoed through the otherwise quiet and still night. And as it howled, it buried it's cock, knot and all, deep in my ass, and then I felt it. The hot, flooding rush of werewolf cum filling me, claiming me, marking me from the inside. And it just kept coming, pulse after pulse flooding my guts until my belly was bloated with it, the swollen knot keeping every drop inside. And then my own orgasm hit me like a brick and my pathetic little clitty was spurting wildly as my boypussy clamped down on the absurdly large cock, milking it, wanting every drop.

We stayed like that, tied and locked together, for what felt like hours. My cheek was still pressed to against the rough bark of the tree and the beast was panting heavily as it's hot breath rolled out against my upper back and neck. When it's knot finally subsided enough to pull free, it popped out with a wet, obscene sound and a big gush of warm cum immediately started running down my stockings and thighs. The werewolf stepped back then and looked at me, at the ruined little sissy in what was left of the Red Riding Hood costume, skirt up, ass out, cum leaking from my ruined hole, and it growled in satisfaction. Then it turned and loped off into the darkness, howling loudly once more as it padded away, leaving me used and abused on the forest floor.

I stayed there a while, on the ground, shaking and my body aching. And I could feel it still, hot werewolf cum, thick and copious, dripping down my legs and soaking into my stockings, pooling in my heels.

So. Much. Cum.

My black panties were somewhere in the dirt. My makeup was ruined. My costume was torn in places, the velvet stained with dirt and werewolf cum and my own spit and tears. I was utterly broken. But, finally, I pulled myself up slowly, wincing, my ass aching, my jaw sore, and genuinely feeling like I got hit by a truck. I began to look around the clearing for my things, and after a few minutes of searching I found my basket--empty, but intact, and even my panties in a bunch near the base of a tree trunk. I pulled them up my legs and over my ass and fixed and smoothed my skirt, or tried to, but it did nothing to hide the mess between my legs. The cum kept coming, thick rivulets sliding down my inner thighs, obscene and undeniable.

Then I started walking, and doing the walk of shame through the woods was somehow crazier than the act itself. Every step squeezed more of the beast's seed out of me, making me walk bow-legged in my heels, my little clitty still half-hard and extra sensitive against the lace of my panties. I was drunk, and used, and my grandmother's porch light was visible through the trees now.

I should have been horrified. I should have been traumatized. But instead I found myself grinning a private, satisfied smile as I limped toward the house, feeling more like a woman than I ever had in my entire life, and already thinking that I might just take that shortcut through the woods again next year.