Halloween: A Pussycat's Tail

The Literotica Annual Halloween Story Contest is on! Read the scary sexy stories (new ones daily!) and submit your tale of terror for fame, fun, and a chance at cash prizes!"

I smiled wistfully as I read the announcement on my computer screen. While I loved erotic stories almost as much as I loved writing, the unfortunate reality was that I lacked the talent to combine my two interests together. It was easy enough for me to write about things that I had personally experienced, but when the time came to depict the passionate, raunchy encounters that defined erotica, my mind would grind to a halt. A sparse and unexciting sexual history meant that I had nothing to draw from, and with the imagination of a cinder block, I was unable to produce the type of steamy smut that I loved to read so much.

A sexy Halloween-themed story would be doubly impossible. I couldn't even remember the last time I had put on a costume, as long as crossdressing didn't count, and I didn't think it should. A costume meant dressing up as something you weren't, but when I was dressed as "Jennie," I actually felt more like myself than I usually did. Despite that, I had never told a soul about my secret hobby, and short of a few exhilarating-yet-terrifying excursions around the block, I kept my activities confined to the privacy of my own apartment. I wasn't particularly bothered by having to conceal my feminine persona, as it kept things less complicated, but a small part of me always fantasized about what it would be like to show Jennie to someone else.

Still musing to myself, I clicked through the website with familiar motions to browse "Transgender & Crossdressers - Erotic tales of gender bending fun." As was often the case when I read these kinds of stories, I was dressed up as Jennie. Nothing fancy—just a baby pink camisole and matching lounge shorts from Victoria's Secret—it was something any girl might be wearing at home on a lazy Sunday. My shoulder-length hair, usually up in a man-bun, was at that moment pulled back in a loose, feminine ponytail.

Emphasizing my girlishness was the complete lack of body and facial hair that I had diligently maintained ever since I was able to afford to move into a small studio apartment of my own. I hadn't had a girlfriend in years, and had no fear of anyone noticing my unusual silky smoothness as long as I stuck to my usual sweats and hoodies; I was often amused by how drab and functional my male wardrobe was compared to the variety of cute and trendy girls' clothes that I greedily hoarded. Similarly, I had grown accustomed to painting my toenails because, frankly, nobody else was ever going to see them.

Currently they were a playful pastel pink, a distinctly feminine shade that contrasted sharply with the un-girlish bulge that was now growing in the front of my short-shorts in anticipation of the latest and greatest crossdresser fiction. I moaned softly as I rubbed the bulge through the soft cotton with my middle finger, pretending I was a real girl playing with her clit. Since I inevitably ended up fingering my butt whenever I masturbated, I always thoroughly cleaned myself inside and out before such "literature sessions."

BZZZT. BZZZT. BZZZT.

I sighed with annoyance at the interruption and glanced at the cell phone vibrating on my desk like an angry wasp. In the age of emails, texting, and instant messaging, I only received calls from telemarketers, my parents, and my best friend since elementary school, who despite being the same age as me, refused to abandon this archaic mode of communication.

BZZZT. BZZZT. BZZZT.

It was Zach, so of course I picked up.

"Hey man, are you busy?" he slurred, and I could tell he'd been drinking heavily. Zach was a party animal, but it was still a little too early to be going that hard, even if it was the night of Halloween.

"Nope, what's up?"

A pause on the other end. "Uh, hello?"

Shit. Even though I almost never left my apartment as Jennie, I still regularly practiced my girl voice just for my own amusement. At some point it had become second nature to use it when en femme, and without thinking I had answered the phone in a soft, feminine purr.

I coughed and exaggeratedly cleared my throat. "Sorry, something in my throat. Everything okay?"

"No." I could hear his voice shaking. "Uh...Jess's been cheating on me."

I was flabbergasted. Though Jessica was a stunning, blonde bombshell with no shortage of admirers, Zach was also a solid catch in his own right. Standing at 6'5" with a dimpled smile that he flashed easily and often, he had maintained his lean athleticism from his college basketball days. Even more endearing than his mop of sandy brown hair and a childlike obsession with comic books was a rare, sincere earnestness. I often joked that he was like a Golden Retriever trapped in a human's body. It was rare to find a sweet guy like Zach who also happened to be an attractive, physical specimen, and I would have expected Jessica to try to lock him down for marriage. They were a disgustingly picture-perfect, hashtag-goals couple. Or at least I had thought they were.

"Ah, fuck. I'm so sorry, dude." My heart truly went out to him. It wasn't the first time that he'd been deeply hurt in a relationship. Despite having every right to be a fuckboy, he was instead loyal and guileless to a fault, which more often than not led to him being taken advantage of. "Do you wanna talk about what happened?"

"You know how I was in New York all of last week for work?"

"Yeah."

"I just did the laundry and...Jess's panties had a bunch of dried cum in them." Despite the circumstances, my pulse noticeably quickened. The words "panties" and "cum" together in a sentence tended to have that effect on me, a Pavlovian response to all the dirty crossdressing stories that I read.

"Are you sure it wasn't—"

"Yeah. We've been fighting and haven't had sex in a while. Well, I haven't been, at least."

"Dude..." I didn't really know what to say. "Have you...talked to her?"

He chuckled sadly. "There was more screaming than talking, but yeah. I told her to grab her stuff and kicked her out."

"You...okay?"

"Yeah, I guess. I just needed someone to talk to, you know?" Zach's voice cracked a little.

"Of course. You know I always have your back." This wasn't just an empty platitude; we both knew that we could talk to each other about anything. Well, almost anything, I thought, tracing a finger down the pink strap of my cami.

"God, I feel so fucking stupid," he sighed. "And I know this sounds dumb but I was really looking forward to tonight."

Unlike me—who had planned to spend Halloween night at home with a box of tissues and some sexy crossdresser fiction—Zach loved Halloween. Every year, he spared no expense in hunting down intricate, tailor-made costumes based on his favorite comic book heroes. Competitive by nature, he usually joined one of the costume contests that took place in the nightclubs around the city. This year, I knew he had been planning to go as the Dark Knight version of Batman.

He had invited me along, of course, but as usual I had declined. It wasn't that I hated partying—what I hated was how I inevitably ended up back at my apartment all alone, with a pounding head and another few hundred dollars in credit card debt. Especially after I had built out my collection of girly things, it was simply more fun and economical for me to stay in on the weekends to dress up, take pictures, and read smut.

"Hey, Halloween's not cancelled," I said. "You can still party. In fact, you should. It'll do you good to have some fun."

"We were s-supposed to be in the couple's c-costume contest," he said, hiccupping, and in my head, I could clearly see his sad, innocent, puppy dog eyes. That bitch.

"Ah, shit...you can still do the individual contest, yeah?"

"No, it's too late to sign up. I don't care. It's stupid anyway," Zach said without conviction. "Halloween's stupid."

"You know you don't mean that, buddy."

"I guess not," he sighed. "Hey, did you end up making plans tonight? Wanna come over and play Halo or something?"

"No plans." My best friend needed me, and so my dirty stories had to wait. "I'll be right there."

* * * * *

Zach was an inconsolable mess. His puffy red eyes betrayed that he had been crying, and he reeked of whisky, confirming my suspicions that he had been drowning his sorrows. Ordinarily, we were a competent duo in almost every video game we played together, but after our fourth loss in a row it was clear that Zach's mind was on something else, likely the girl who had just broken his heart. He was also uncharacteristically quiet, and unused to the awkward silence between us, I had been generously helping myself to his alcohol.

As we queued up for what was certain to be another lopsided beatdown, I downed a big gulp of whisky Coke from a red plastic cup. "Might as well loosen up," I joked. "Before I get completely fucked."

"Fuck, I'm sorry. I'm playing like ass."

"Yeah, you are, but don't worry about it—"

"Thanks."

"—because what else is new, loser?"

With effort, he gave a small smile at my attempt to bring our usual banter. "You know I'm the one that carries your little bitch ass, right?"

"Yes, daddy," I said, rolling my eyes sarcastically as I struggled to extricate myself from the couch. My low tolerance was showing, and it seemed like I was perhaps a little drunker than I had realized. "Pause the queue, I gotta pee."

I shuffled my way to the bathroom, where the sterile white tiles were uncomfortably cold beneath my bare feet. The lights flickered on at my touch, then multiplied and danced around my pounding head. Ugh, should've gone easier on the booze.

I didn't trust myself to not pee all over Zach's floor in my dizzied state, so I put the toilet seat down before sinking into it with a groan, curling my painted toes in pleasure as I peed like a girl. Glancing down, a cold realization dawned upon me.

I wasn't wearing socks.

My cute, pastel pink toenails had been on full display for the past three hours.

Oh fuck. My mind spun frantically. Oh fuck, oh fuck, oh fuck. I was always so careful about this kind of thing, but in the rush of Zach's emotional emergency I had finally slipped up.

Why didn't Zach say anything? There was no way he could've noticed and not said anything, right? We were talking about a guy who answered "yes" when his girlfriend asked if a particular dress made her look fat. He couldn't tell a lie to save his life, plus he had seemed pretty wasted. He must not have noticed, I decided with a sigh of relief.

But that relief was short-lived, as I realized that it would still take a few more hours before Zach, with his absurdly high tolerance, would get drunk enough to pass out. I couldn't just bail on him in his current state and go home. But neither could I risk him noticing that his best friend was wearing pink nail polish on his toes.

Panicking again, I rifled through the bathroom drawers and cabinets in search of any nail polish remover that Jessica might have left behind, to no avail. I did find a mesh bag of hers stuffed deep in the recesses of the bottom drawer, but when I unzipped it I was disappointed to find only makeup.

I slapped my forehead with my palm when it suddenly occurred to me that I could simply borrow a pair of Zach's socks. I silently apologized for the invasion of privacy as I opened the door that led to the adjoining walk-in closet. Had someone done the same to me, I would have had a difficult time explaining the number of dresses, skirts, and high heels inside. But Zach had, as expected, a very ordinary male wardrobe that smelled pleasantly of dryer sheets, albeit with several conspicuously empty spaces where I assumed Jessica's stuff used to be.

Then I saw it: the couple's costume that Zach had gotten for Jessica, which she had no doubt intentionally left hanging in one of the closet's gaping voids like a knife in his heart.

Mesmerized, I walked up to it and ran my fingers lightly over the supple leather and intricate stitching. It was the Dark Knight version of Selina Kyle's Catwoman's outfit, seared into every adolescent boy's memory by the voluptuous Anne Hathaway. Matte-black with a highly impractical four-inch stiletto heel built into the foot, a single zipper from crotch to neck allowed the lucky girl to put on—or take off—the catsuit. A springy tail and eye-mask were looped over the neck of the hanger.

Never in my life had I seen a piece of clothing that was so cloyingly and overwhelmingly feminine, and this was as someone obsessed with girls' clothing! I wasn't particularly into leather, but could now see its appeal; there was something erotic and taboo about wearing another creature's skin over your own.

All thoughts of my nail polish problem fled my head as, in a trance, I slipped the costume off the hanger and held it up against my body, glancing at the floor-length mirror in the corner. Jessica was pretty tall for a girl, and so the tailored catsuit was just the right length for me. In my hands, I noticed that the costume was much heavier than I had expected, even taking into account the weight of genuine leather. Apparently, thick gel padding had been cleverly sewn into the hips, ass, and bust, no doubt intended to enhance the endowments of a genetic girl like Jessica to outrageous, comic book proportions.

Before I knew it, my clothes were on the floor, and I was drunkenly stuffing one foot and then the other down the legs of the catsuit. It was a tight fit but I managed to squeeze in, and I eventually felt the familiar constriction of my foot inside a heeled leather boot. Like most crossdressers, I was no stranger to high heels, and after years of practice in my apartment I was able to walk in them as naturally as in my sneakers. Inebriated as I was, I was still able to expertly balance in the sky-high stilettos of the costume.

I shivered in delight as I then slid my arms into the slick, rippling sleeves, feeling the soft leather caress my body like a lover. My boy parts were, out of habit, tightly tucked between my legs, but I could feel them straining against their leathery confines. Taking care not to accidentally pinch my skin, I nervously zipped up the costume before looking at the mirror once again.

I covered my mouth and gasped.

I looked fucking hot.

It wasn't just the costume's exquisite quality; it also fit like it had been painted onto me with a wet brush, and the gel padding that jiggled realistically with my every move also transformed my figure into a definitively feminine hourglass. As I swiveled in front of the mirror to check out what the padding had done for my butt, I noticed a strange hole that had been deliberately cut into the costume directly below where my tailbone was. Dismissing the oddity, I excitedly ran my hands over my new curves as a warm tingle curled up my spine. I drunkenly wondered what I would look like with makeup and the rest of the costume on.

Grabbing the mask and tail, I rushed back to the bathroom and spilled the contents of Jessica's makeup bag onto the counter. Velvety black eye shadow and mascara from Bobbi Brown, Kat Von D stiletto eyeliner, and ruby red YSL lipstick—a girl like Jessica used only the good stuff. Coincidentally, it was also exactly what I needed for the dark, sultry "night out" look I had in mind.

I applied the makeup to my face with practiced motions, and was amazed at how flawlessly the products went on despite my nervous, trembling hands. I made a mental note to return at some point in time to "borrow" Jessica's kit, as I was certain neither she nor Zach would miss it.

Taking care not to smudge my makeup, I carefully put on the eye-mask that—in true comic book fashion—did absolutely nothing to conceal my identity. Instead, the strip of black leather with its two pointy "ears" only emphasized my porcelain features and fuck-me makeup. Now for the pièce de résistance. Examining the tail, I couldn't find a waist strap, buckle, or any other means to attach it to the body of the costume. Then I saw it.

Oh. So that's what that hole was for.

At the end of the sinuous tail—made out of the same leather as the rest of the costume but internally reinforced with springs to give it a life-like bounce—was a stainless steel butt plug. And not a small one, either. I immediately deduced how it was supposed to work. The plug was meant to go through the hole in the back of the costume and...into the wearer. To a casual observer it would look like the tail was merely stitched onto the exterior of the costume, but the person wearing it would know better, especially if anybody touched or pulled on it. My pulse quickened at the thought of Jessica strutting around with the heavy plug in her tight little butt, and quickened further when I imagined Zach tugging and playing with her tail in public with no one the wiser. No wonder Zach had been "looking forward to Halloween!"

In for a penny... I raised the plug to my lips and licked the cold steel like a lollipop, lathering it with wet saliva. Watching the dirty scene in the mirror, I somehow felt like my own voyeur.

Threading the slimy butt plug through the back of my costume, I took a deep breath and pressed the cold steel against my smooth, hairless sphincter. It slid inside me with a pop, and, shivering, I felt the familiar, erotic feeling of "fullness" in my rectum.

I gave a little victory wiggle, and gasped as the spring-loaded tail rippled with motion, sending a surge of intense pleasure straight into my tight, sensitive hole. I knew that as long as I had it in me, my lips and cheeks would stay attractively flushed and my pupils fully dilated in an aroused "sex face." Pursing my lips a final time and wiping off a stray fleck of mascara with a pinky, the full impetus of my dramatic transformation finally hit me.

No trace of masculinity remained in the stunning creature in the mirror. Impossibly thick lashes framed smoldering, smoky, come-hither eyes, and her full, crimson, attention-seeking lips were half-parted in a dangerously seductive pout. Her long, tousled hair topped off a leather-encased body with supermodel proportions. She oozed with mystery and powerful sexuality.

I lost track of time as I primped and preened in front of the mirror, drinking in the sight of my own exquisite femininity. Whenever I smiled, the gorgeous Catwoman smiled back and I would feel my poor, confined dick attempt—and fail—to get hard. Trapped in this narcissistic feedback loop, I wanted nothing more than to fuck myself silly. I had become my own perfect dream girl.

It was then that I noticed that the doorknob in the mirror seemed to be turning. I had never had a reason to lock the door at Zach's, and I was a creature of habit. Unfortunately, my carelessness now meant that I was completely and utterly fucked.

Before I could react, Zach drunkenly threw open the door.

"Dude, you've been in there for like an hour. Are you throwing up or somethi—" Zach froze. "Holy. Shit."

The expression of utter shock on my best friend's face would have been comical under ordinary circumstances, but I cringed and braced for the onslaught that I knew was coming. Disgusting. Pervert. FREAK.

The combination of arousal, shock, terror, shame, and confusion was too much for my poor brain. I sniffled and felt the tears well up in the corners of my eyes, threatening to undo the hard work I had put into my makeup.

"I'm..." Sick to my stomach, I put my arms up and gestured helplessly, choking back tears. "I'm sorry. Fuck, I don't know what I was thinking. I know this is really fucking weird. I'm sorry. I don't know what came over me. I'll take this off right now."