Halloween Dress-up

I turned away, ready to walk back to the freeway and hitch another ride, when the massive double oak doors creaked open, drawing my attention.

I got a shock when I turned. I didn't realize that the Brown's had hired a butler. The servant was uniformed in formal attire, had a dark moustache and hair and was wearing a bowler hat, just like in an old British movie.

"Is Sally home?" I asked hopefully.

"I'm the only one here."

My shoulders slumped. The butler looked me up and down. I did not know whether to be more embarrassed by my hair or by the raging erection still trying to rip through my zipper.

The butler grinned. "You look wet and miserable. I should invite you in to dry off, but this being All Hallows Eve, you lack the proper pass phrase."

I just stood there, puzzled. Just as I was about to turn and walk away, the butler giggled, and said, in a much higher voice, "Trick or treat, silly Timmy. It's me Sally. How do you like my costume?"

She grabbed my arm and pulled me inside the foyer, wrapping me in her arms and hugging me tightly.

"Trick or treat," I managed to mumble as her lips unexpectedly met mine, her tongue pushing my teeth open much like Anne's had. This time the sensation was less unexpected, but the sudden quality still made the sensation electric. A current ran from my teeth to my toes. Along the way, it raced through my balls and up my shaft. I was again embarrassed by the surge of my meat, trapped against Sally's groin. I tried to pull away, but she wriggled fiercely against my wood. As we clenched together, her moustache rubbed along my skin, a totally unfamiliar sensation. I had heard that it tickles, but I found it added to my shivers, like a thousand tiny needles were pricking my skin, each sending a signal via a nerve ending which ran directly to the tip of my cock.

"Since I tricked you with the costume, I better give you a treat," Sally said, stepping back out of the kiss, ending the hug but still with her hands on my shoulders.

"Wow, you totally fooled me," was all I could think of to say. What a dork.

"Just what would you like as a treat?"

Sally looked at me in a totally new way. She glowed, and behind the makeup and pasted on moustache, her eyes danced and her smile beamed. Suddenly, all things seemed possible.

"You....I want you," I stammered.

Sally took me in her arms. It felt odd, not just because I was hugging a girl who had been my best friend forever, but because the visual of hugging a man was superimposed upon the moment. The roughness of the whiskers brushing my cheek added to the gender confusion. However, my cock was not confused. It surged larger than ever. I knew it was ready to explode, and did not know what to do about it.

"You seem pleased to see me," Sally growled, again using the butler voice. She pushed her pelvis against my erection, holding me tight, her hands gripping my back. Her tongue flicked across the skin on my neck just below my chin.

"You taste yummy," she giggled.

Now that we were close, I could smell the odour of alcohol on her breath.

"Have you been drinking?" I stupidly asked.

"Just a little," she replied, and then belched.

She giggled again, stepping out of the clench. "Okay, maybe more than a little. Chad dared us all to dress as the opposite of our true nature. I thought that going as a slut would be too obvious, so I thought I'd be a gentleman."

"As opposed to a lady?"

"I'd rather be a tramp."

I think my jaw dropped straight to the floor. I always knew Sally liked kidding around, but I always saw her as shy and reserved. As far as I knew, she was a virgin, not a tramp.

She broke the silence. "You should come too."

"But what would I dress as?"

Sally thought, miming the part, finger up to her cheek. Then, as if a light bulb was going off she announced. "That's it. Dress indeed. I have loads and loads of dresses. You can wear one of those."

I felt my cheeks warming as I blushed. "How is that opposite the real me?"

"Going femme is so opposite your hunkiness," Sally said, her fingers trailing along my arm, making my hairs stand on end. Hunky? Me? Not really, but if Sally thought so, fine. Still, I seemed to have been backed into a corner. Especially since Sally's fingers traced the line of my arm to my hand, caressed my palm, and then lifted my fingers to her lips. She took each digit into her mouth individually, rolling her tongue around the flesh, teasing them. The scratchiness of the fake moustache was odd at first, but once she closed her lips around each finger, the sensation was incredible, like being inside a whirlpool. I imagined her doing the same to my cock.

Sally may have sensed that I was even more excited than earlier, or else she just had good eyes focused on my crotch. "I guess that you're still glad to see me," she observed. "Don't worry, Tim, I won't think that you're queer or anything if you dress as my lady friend. In fact, maybe you'll find wearing panties just as exciting as I'm finding boy's briefs."

She giggled again. "Thank goodness for little brothers. I never would have fit my Dad's."

Another hug followed, complete with a kiss that included even more tongue. I could taste the sweet booze breath. I was conflicted. As much as I wanted Sally, I was afraid she might hate me if I took advantage of her drunkenness. Plus the situation was just plain weird. Yet every additional twisted image stiffened my cock more.

"Wanna see?" she asked, snapping me out of my introspection.

"Huh?" I muttered, but my chin was nodding yes.

This was all the encouragement Sally needed. I had seen her panties a few times when she bent over to pick up books or such, but then I had always turned away, embarrassed to be peeping at my chum. This time, it was all erotically charged. I had never been to a real strip bar, but I had seen strip teases in movies, and Sally reminded me of an old time stripper, with lots of tease. She began by swaying her hips, shimmying at the knees. She tossed her head back, closing her eyes as her hands slowly undid the buttons of the heavy man's coat. Starting from the bottom, saving the revelation of her chest for last. With each movement of her hands, her body shook more forcefully, finally seeming to thrust towards me

The unbuttoning took quite a while because Sally began tracing her finger tips across her groin, and then her belly as it was revealed, each circular motion more daring than the last, teasing at the belt , then undoing a button, and then brushing the zipper of her pants, and then another button, and so on.

When my own fingers started caressing my bulge, Sally, as if clairvoyant, snapped her head forward, looked at me and said, "Save that for me."

I could not believe my ears. She wanted my cock, and maybe my cum. I was quivering as I watched the rest of her show.

She finally undid the final coat button, brushing the heavy fabric aside. Underneath however, her tits were still masked by a waistcoat over a white men's dress shirt and tie. She did not remove them, since it was the boyish underwear she planned to show me. Instead, she prolonged the tease by miming undoing each button on the waistcoat from top to bottom. This served to draw my eyes down from her hidden treasure chest to her swinging hips.

Dancing to her own internal music, Sally swung around as her palms cupped her buttocks, and bent over so far that she was smiling up at me upside down between her legs. With a quick spank on her own bottom, though, she reminded me where my eyes belonged. As she spun back to face me, springing up right with the grace you might expect from a cheerleader, not the library nerd which Sally really was, somehow she undid her belt buckle. One second it was taut against her cute pouchy waist, the next, the buckle was dangling loose, as she reached towards the sky. Again, the motion drew my eyes up, allowing me to drink in her heaving beasts pressing through the waistcoat, but then settling on the shiny brass at her groin.

As she ran her hands down her sides to her hips, Sally spoke again. "Poor Timmy, you don't know where to look. Is it a strange feeling, being so turned on by someone with a moustache? Are you wondering whether the bristles will tickle your dickle?"

Sally must be drunker than I thought. This was not how best friends acted. We had never teased about blow jobs. Unlike a lot of girls, Sally had never passed them out as a way to gain social standing. Suddenly my heart leapt into my throat again. What if Sally had been blowing Chad or the other guys at her new school, in order to belong?

She read my mind. "I bet Chad would like a moustache tickling his balls. That guy talks about blowjobs so much that you just know that he's not getting any. Unless he's giving them."

I was still puzzled. "So are you dressed this way to try to turn Chad on if he's sort of gay?"

"No silly, I want to turn you on. I'm dressed this way to see if you are a little gay."

As my jaw dropped to the floor, Sally quickly unzipped her trousers and dropped them to the floor. Underneath, she wore a plain white pair of jockey shorts. She laughed heartily. "So, Timmy, are you queer or do you like to eat pussy?" Sally challenged me, her eyes again closed as she focused on her self help.

"I never have," I stammered.

"No time to start like now," she answered. She opened her eyes, locking her stare on me. "I dare you. I'm sooo wet," she moaned, her arm flexing. I stood there, still in shock.

"Don't worry, I think my little brother is too young to be jerking off yet, so there likely aren't any of his cumstains on here, if you want to eat me. Any cumstains are mine."

Her hand dove under the elastic waistband. I could guess from the curve of her wrist that she had immediately buried at least one finger in her pussy.

All our lives that had been our code, a silent pact. Whenever either of us was too cowardly to do what we had to do, the other would make it a taunt, and the challenge was always accepted.

My jaw must have dropped open. "That's it, open wider," she teased, running her hands along the top edge of the waistcoat, caressing the upper slopes of her otherwise buried breasts, and then down again, fingertips brushing her hip bones, tracing the lines inwards to the top of the underwear.

I still stood frozen while Sally dug fresh juices from her pussy and raised her fingers to her own protruding tongue. She dramatically licked her lips and then rolled the nails along her little pink tongue.

"Now your pants," she continued, not taking her hand from her mouth.

"You do it," I said, a bit shocked by my own nerve. I stood there frozen, almost unable to breathe.

"You pansy," Sally growled in her mannish voice, rushing at me in a couple of quick steps. She didn't just close the gap. She kept walking, her shoulders slamming up against me and her energy pushed me hard into the wall.

Sally's whiskers rubbed my cheek as her hands struggled with my belt. The roughness was disconcerting, and for a moment, my hands went automatically to her shoulders to try to push her back, but Sally pinned me tight with her knee. Soon, the unfamiliar feeling warmed my flesh, and suddenly I was aware that each hair was sending electric currents directly to my nipples and groin as they rubbed along my skin. I relaxed and struggled just enough to encourage Sally to continue. I felt my pants fall to the floor as she stepped back.

"Now we're even." I said.

"Not quite," Sally replied. "You haven't reached inside your underwear. Though you oughta be wearing panties."

My right hand seemed to move with a mind of its own, accepting Sally's dare. My fingers dove quickly past the waistband of my briefs, which was already stretched open by the cockhead trying to burst free.

"Imagine it is silk lace, not plain cotton and slide your hand up and down that fat pulsing shaft," Sally instructed, her eyes locked onto my groin.

I did as instructed, trying my best to forget she was watching and simply do the familiar motions. Staring at her fingerfucking herself with one hand while tweaking her own nipples under her shirt with the other made concentration difficult. A corner of my brain still was free for rational thought, realizing how unlike the normal Sally this was. The unusual clothing seemed to make her into a bolder person.

"Try to keep the fat knob at the top inside your shorts. It keeps peeking out at me," she scolded, "if you had silk on, you'd want that smoothness against the flesh there. Is that part extra sensitive?"

A lump caught in my throat. Unable to speak I just nodded.

"I think I'd like to feel it, if you are man enough to eat me first. I might even kiss it, if you don't mind the moustache."

With a quick flick of the wrist, Sally's panties fluttered to the floor. She leaned back against the door frame, the open door into the rest of the house providing ample room for her to spread her legs wide.

I had never seen her pussy before, despite all the years we had been best friends. It was trimmed, I could tell from reading porn and trolling the internet, curly reddish hairs in a neat triangle.

"What are you waiting for, eat me boy," she growled in her mannish voice. Her fingers were slowly stroking her pubes, nails grazing the labia. I was frozen, just watching her clit peep shyly out of its nest like a baby bird.

She tweaked her flesh, making that bud pop out fully.

"Suck my dick, pussy," she demanded.

The little rational corner of my brain was silent. Automatic muscle control took over. Two quick strides and I was in front of her.

"Kiss me first," I pleaded.

She grasped my hair roughly and pulled my lips to her mouth, our teeth clattering as she held me by the ears, twisting our faces together.

Time had lost any meaning. It might have been seconds or hours. All I know is that Sally finally used my ears as handles to push me back, both of us gasping for air. She barely paused before shoving my head down along her body. I rolled my tongue along the soft curve of her neck, enjoying how this made her tremble, goose bumps blossoming on her flesh. However, when I tried to raise my hands and pull open her vest, she released my ears and pinned my arms behind me.

"A good little cocksucker doesn't kiss the master's nipples," she growled.

The pressure of her hands on my arms arched my back and buckled my knees. It was impossible for me to continue standing. My nose barely grazed her enclosed chest as I fell to my knees.

My nose fell naturally into the "v" at the top her thighs. I instinctively began nibbling at the tender white flesh, causing Sally to mew like a kitten. Her fingers again grasped my hair, guiding me towards her honey pot.

The first real clit I had ever seen in person stood proud and stiff in front of my eyes, sticking out, as if begging to be kissed. It did indeed look a bit like a miniature cock. I paused, watching it vibrate as Sally anticipated my tongue.

"Blow me, bitch," she demanded.

I complied, but not in the conventional manner. Instead, I literally exhaled across the tip of her love bud, the pressure making it nod to one side and then to the other. Only then did I taste her for the first time, inhaling her odour deeply as my lips surrounded her clit. I drew it deep into my mouth, wrapping my tongue around it. I must have learned something watching porn, because my fingers knew just when to slide up her thighs and caress her labia, forcing her to open her legs even wider as I first fingered her gently, and then finger fucked her forcefully. I let my teeth nip gently at the base of her clit as the head bounced inside my cheeks, my head bobbing up and down, stretching her flesh from her body.

Sally's hips bounced, her ass smacking the door frame, and then mashing her cunt into my face. Her juices were flowing freely, coating my hands and face. Her moans became groans, until finally she was screaming with pleasure. She closed her hands around the back of my head, trapping my mouth against her pussy. "Swallow my come," she cried.

I felt what had to be her climax as she shook so hard that she would have fallen to the floor except that I had her still pinned against the wood. Mind you, her screaming "I'm coming....." was also a good clue.

Her fingers loosened their grasp and I eased back, letting her clit slide out of my mouth. I busied myself licking up the fluids flowing down her thighs, making sure that each trail led me back to the bud at the center of her rosebush. As I worked, her shuddering subsided slowly, each wave flowing through her body more slowly.

As Sally stopped shaking, she released her grip fully. I shifted back. I took my fingers out of her pussy. She slowly fell down along the door frame to the floor as I licked her nectar off my hand. Once again, her eyes locked on mine as I slowly feasted on her come.

"Such a good little cocksucker, swallowing it all," she teased. "I bet you expect me to kiss that filthy mouth now, you little bitch."

"Please," I moaned. Her grin was evil, the corners of her moustache twitched like a bad movie villain.

Without another word, she reached up behind my head and drew my mouth to hers. Our kiss was like two lions battling to be the King of the pride. Her teeth tore at my lip even as she tongue lashed mine, forcing its way almost top my throat, the taste of her own loins her reward. Her fingers tousled my hair, tickling my neck and reaching down to the top of my spine, playing me like a clarinet.

Sally slowed the dance of tongues as her other hand brushed my cockhead, which was now fully exposed, flapping against my belly, excited by the rough fabric of her waistcoat and the heat trapped between our bodies.

As the kiss ended, Sally moaned slightly, and then giggled, girlishly this time. She quickly reverted to character, pitching her voice deeply. "That was a fine treat for me, but I think I still owe you one," she said.

"Yes, please," I said, imagining that she would now suck my aching cock. I no longer cared whether she was a virgin or a slut, a stranger or my best friend. I wanted her lush lips bathing my helmet, even if the moustache tickled.

"Well, first a trick," she chuckled. Suddenly, she whipped the belt out of her trousers which were puddled nearby on the floor. Before I could react, she lashed my hands behind my back, standing up, admiring her handiwork and then unleashing a lusty laugh. She left me huddled there in the doorway, as she stepped towards the huge ornate circular stairs which disappeared into the dark upper stories. Something about the foggy Halloween night and the dim lighting made this seem sinister. I had never doubted Sally in our entire lives. I was debating whether I should begin doubting her – or at least this masculine version of Sally- when she spoke again.

"Like I said earlier, since I'm the man, you need to become the girl. I'm going upstairs to lay out a nice outfit for you. Once it's ready, I'll come down and release you. You'll go up and dress, and finally, I will come and give you your treat."

I struggled briefly, but found that Sally had tied me up tightly. When she returned moments later, she found me resigned to my fate, relaxed in the doorway.

"What a scrumptious looking treat you have there for me. It's all I can do to resist eating it now. But that would be gay," she said in her manly voice, but then she giggled and added, "and this part is supposed to be your treat."

She stepped behind me and showed surprising strength, grabbing the belt and hauling me upright. One shove got me walking, albeit awkwardly. I stumbled when we reached the stairs and tugged my wrists apart, silently begging her to allow me freedom.

"Crawl if you have to. I'm not releasing you until you are a girl." Sally gave me another shove, less gentle this time. As I stopped on the first stair, she pushed up tightly behind me. While upstairs, she had apparently found another belt, as her trousers were once again in place. The belt was not all she had added however. My asscheeks were startled to inform me that somehow Sally had grown a cock. It was rigid, oppressed up between my cheeks.