12 comments/ 423359 views/ 87 favorites Halloween Dress-up By: sirhugs "Tim, can you please come on over? I have to go to a party later, and I'm already dressed in costume." "Why are you dressed up so early?" "I had to take my little brother Teddy trick or treating. But now my parents have taken him to a party at the club." Even though I was a guy, and she obviously wasn't, Sally Brown was my best friend, and had been since we were kids. A few months before we had turned eighteen, Sally's dad had won the lottery. Sally's folks had moved into a fancy ranch house on a new golf course miles out of town. They had insisted that Sally finish high school in private school, so we had to really scramble to see each other. Usually, that meant Sally driving into the city to visit me, since she had been given a car last birthday. Tonight, however, was Halloween and to my shock, Sally had plans. She was going to a party. Without me. I was surprised at how this made my stomach churn, my heart sink. I gulped, regaining my composure. To buy time, I nervously asked, "How was trick or treating?" "Well, some old perv showed me his thingy." "Yuck, what did he do?" "He just came to the door in a ratty old bathrobe. When Teddy turned to leave, I was still holding the door. The perv just brushed the robe open with his hand. His thingy was drooping out just like his sweaty tongue. I tried not to look, but then I met him in the eye and he grinned at me and wet his lips. I felt like Little Red Riding Hood meeting the Big Bad Wolf, and you weren't there to be my brave Woodsman." "Is that what you dressed up as?" Sally laughed a deep belly laugh. Though she had long hair and a curvy figure, she was never afraid to be just one of the guys. "Not anywhere close. The party is a themed event, one of the kids at my new school is hosting. His parents are away, so he dared us to be really wild." At the mention of this classmate, I again felt tense. "So what are you?" This time Sally's laugh was all girl, a series of rising soprano trills. "I'm not telling," she said, teasing. "You have to come over to see." "So what did you do after the old man showed you his ...." I paused, unsure what word to use. "His dink?" Sally suggested. "You'd think a perv would be all hard and stuff when he flashes. But this guy had a wrinkled little thing, and it was just dangling there." "How do you know it was little?" The question was out of my mouth before I thought about it. For years, Sally and I had talked about everything. Puberty hadn't changed that. We talked girly stuff when she needed makeup tips and football when it was the season. Since her move, however, it all felt a bit weird. "Because I've seen how lumpy your pants get when there's a sex scene in a movie, and felt how big it is when we took those dance classes before junior prom. I always wondered whether holding just any girl makes a boy that stiff. Or whether it was me especially doing it to you." I was really glad at that moment we were talking on the phone, because if Sally had asked me that in person, my blush would have told her all she needed to know. I was speechless again, struggling with strange emotions. I wondered whether to risk my best friendship and tell Sally how I really felt. I did not dare tell her that I lay awake at night, my cock throbbing, until I learned that if I caressed the shaft just right, my balls would draw up tight to my groin. That I would picture her last summer, at her Dad's country club, climbing out of the pool, water droplets flying off her hair, her tanned skin glowing, her breasts bursting out of a teeny tiny bikini top. Thinking of that would always make my hand stroke faster. My fingers would be clenched around my rod, the tips of my nails grazing the tender flesh of my scrotum at one end and the lap beneath my head at the other. It seldom took long before the slit at the end of my helmet would start gasping like a dying man in a dessert, as I imagined her full plum lips kissing the tip of my tool. Sleep would follow only after the explosion of goo. I usually drifted off imagining Sally licking me clean. Suddenly, in the silence, I wondered if my best friend swallowed. In fact, whether she was still a virgin. Surely, she would have told me if she lost it. But then, she hadn't mentioned this party. If I had not called, I would never have known about it. We never went to Halloween parties. Those were for cool kids, and we had never been part of that crowd. "Who's this guy having the party?" I stammered, asking possibly the worst question to break the silence. "Oh, Chad. He's kind of cool. You'd like him. Not a typical private school rat at all. Seriously strange." I wanted to ask just how strange, and how she knew, but wasn't sure I was ready for the answer. Despite my confusion, I was certain of one thing. My trusty penis was threatening to burst our of my zipper, and the only solution was to see Sally face to face, if only to see what she was wearing which had inspired the old perv. "But I don't have a car." I said. "How will I get out there?" This time, Sally's laugh was plain wicked. I wondered at that instance if she was dressed up as a sexy witch, a bustier pushing her plump boobs towards her chin, nipples threatening to pop loose, knee high boots and a cape over a short tight leather skirt. Just the possibility almost made me come in my pants without even touching my aching organ. "If you want to see me, I'm sure you'll find a way. But hurry. Chad said he locks the doors at midnight, so I haven't got all night." The rush of confused emotions sent shivers through my spine. From there, it surged through my balls up my shaft. I had never felt so turned on, but so afraid. I was afraid that I was too excited by Sally as a female. I was afraid I would lose her as a friend. I was afraid she would lose it tonight with Chad, if she hadn't already. I was afraid that I would never get sex. I was afraid at trying sex with Sally, and disappointing her. I was mostly afraid that I would come in my pants before I got to her house. "I'll be there within an hour," I promised. I raced out of the house after hanging up the phone, glad that my Mom and Dad had already left for whichever bar they were frequenting these days. My alcoholic parents were a big reason why growing up an only child, I had wished that Sally was my sister. Now, it felt a bit like I was contemplating incest. Instinctively, I ran over to the nearest busy intersection, and stuck out my thumb. Hitchhiking is a lost art, because of the risks, but Sally and I had frequently used that as a way to escape the confines of the trailer park, before she had escaped forever. I had never hitched alone before. As I stood in the chilly air, I realized that Halloween night might not be the smartest night to start. But I had promised Sally I would get to her house, and I sure didn't have cab fare. A fancy convertible sports scar slid to a shuddering stop inches from my foot. Despite the season, the top was down. The driver was dressed as a ghost, white sheet flapping in the breeze. His date was dressed like a 1920s flapper girl. She was seated on the rear deck, her legs dangling over Casper's shoulders as she sipped straight from a mickey of gin. The nippy night, or the thrill ride had teased her nipples erect. They were threatening to pierce the flimsy fabric of her dress. As the driver spoke, I noticed that her lacy panties were clearly visible. "Where you headed dude?" the ghost asked. "West Grove Estates," I replied. "Too bad I only give rides to strangers in costumes, then, cause I'm headed straight there." He laughed and roared off, his girl blowing me a mocking kiss as they vanished. I stood shivering. There just wasn't much traffic on a Halloween evening. West Grove was at least a fifteen minute drive away. My promise to be there in an hour seemed impossible to fulfill. I slumped, dejected. Still confused about why I felt so strongly, I feared more than ever losing Sally, and had to admit, it was not her friendship which I feared losing. Just to make matters worse, it started to rain, a damp drizzle which matched my mood perfectly. I started trudging along; thumb at half mast, wondering why I didn't just go home, when seemingly out of no where, a black SUV screeched to a halt, the plume of water from the tires miraculously missing me by inches. A motorized window hummed down, revealing that the vehicle contained a bevy of beauties. It was overcrowded so that counting instantly wasn't possible. Someone said, "Hey , big boy, want a ride?" I peered inside the vehicle. The driver was dressed as a naughty nurse, with red fright wig hair, overstuffed bra, almost nonexistent skirt, and white stockings with pretty lace tops. Next to her in the other bucket seat was the spokesman of the crew, a gum chewing harem girl, whose bra needed no Kleenex. Her well tanned cleavage was all real, and seemed to be threatening to jump out of the car and slap me in the face. In the back, I made out several girls literally piled on top of each other- a kitten, a ballerina, a chef, plus a few others buried beneath. A strong odour of booze wafted to my nose. Once again, the blood exited my brain and filled my cock. "You look pretty crowded," I foolishly answered. "Suit yourself," the driver growled, sounding miffed. When she pulled away, she seemed to take extra care to splash me with the plume of water off of her tires. Dejected, I trod on along the road, the moonlight glistening off the puddles. At least the rain was slowing, but I could not stop thinking of what my beloved best pal Sally might be doing later with Chad. I pictured her as some total skank, an image of her I had never had before. I imagined that she would be scantily clad in a provocative costume. He would ply her with booze and then lead her to his bedroom. Despite the 'off limits' sign, another couple would be on the bed, except as Chad steered Sally to the mattress, Sally might notice that it was not just a couple but a threesome. She would be too drunk to care, but would still mumble "Chad, I can't." "Why not, you're not a virgin, like that nerd Tim you hang with, are you? Maybe you prefer sissy boys?" I pictured Sally shaking her head no, her long hair flying about her face, both Chad and one of the girls brushing it away from her face as she lay back. In my fantasy, my waking nightmare, Sally protested at the feminine touch. Chad would stroke her face, cooing reassuringly. "It's okay." And then the girl would kiss her. "It's okay," the girl would repeat, her lips still brushing Sally's. The remaining couple would barely stir, but there might be a slight shift, so that they could watch this new thrill. "It's okay," I heard Sally saying in my mind. As revolted as I was by these thoughts, I noticed that my cock stiffened despite the rain. I stuck my thumb out again, though if no one serious stopped soon, I would give up. As I stood shivering, I pictured Chad taking Sally's arms and stretching them above her, while the strange woman distracted Sally, gently shifting her lips along Sally's throat, licking, then kissing, then licking more, finally, nibbling the soft porcelain skin. The other guy might move then to help Chad, producing a pair of handcuffs. "It helps that you came as a cop," the final girl would slur, very drunkenly trying to suck the guy's cock, which had been limp until Sally had entered the room. "Ohhh, look who's excited," the cocksucking girl would say, causing her friend to stop painting Sally with lip prints and look over. "He really must like these tits," she would respond, pulling Sally's top down, allowing her nipples to burst into the air. This thought made me pause. I realized that I did not know what Sally's nipples looked like. Suddenly I resolved that best friend or not, and whether or not she was a virgin, my goal for this Halloween was to find out about Sally's nipples. In the meantime, my fantasy supplied generic light brown kisses, a tad bumpy in the chill. I shook my head, trying to clear out the offensive yet exciting images. I wanted to scream 'No Sally,' like shouting out as another victim goes to their fate in a horror movie. The two strange gals might shift their focus to the guy's rejuvenated erection, leaving Chad to slip along the bed and tweak Sally's nipples. He may reach over, though, and grab a hair clip from the first woman, releasing her flowing black mane as she licked her lover's meat. Chad would apply the clip to Sally's nipple, making her groan in pain, but then moan in pleasure. Suddenly, I sensed that the same perversity which initially repelled her might by then be exciting her. Just as my mind tortured my soul with images of Sally voluntarily reaching over to free Chad's hardness from his costume, a monster truck skidded to a stop, drenching me with water. The passenger was a blonde girl, who looked barely eighteen, dressed as Raggedy Ann. I didn't have to see to guess that the driver would be her boyfriend, and he would be Raggedy Andy. "Sorry about the water," the doll cooed, impossibly girlishly. "How can I make it up to you?" An internal voice deep inside of me which I had never heard before wanted me to tell her that the only way she could even things up would be to strip herself, use her silly costume to dry me, and then suck my cock, swallowing my first load while her wimp boyfriend watched, and then letting me fuck her ass as he licked my cream pie from her cunt. I was shocked. I never thought that way. I still did not say what I thought. Instead I replied, "I need a ride out to West Grove." "No problem, hop in," Anne said, so I did. It was cramped in the cab of the truck, so Anne, after a bit of uncomfortable squirming, her thighs rubbing against mine and Andy's on either side, hopped into my lap. My cock had deflated since the drenching, but the warmth of Anne's tush rubbing against my wet pants quickly revived my erection. I was afraid she might get upset that I was aroused. Instead, she sighed, and then it turned into a moan. She was clearly enjoying the ride. I glanced over at Andy, but he was keeping his eyes on the road. I doubted that he could be unaware of what his girlfriend was doing. I figured he had to at least tolerate her pleasuring herself this way, or perhaps even be a bit excited by it. I knew that I was very thrilled. Anne adjusted herself slightly. I felt the pressure from her pussy pushing down on my cock. The more Anne squirmed, the more fun we had. "What a waste of a good hard-on," she whispered, twisting around and pecking her lips on my ear. "Oh, Andy, he's all hard," she said, then darted the tip of her tongue deep inside my ear. This in turn made my cock thrust harder at the fabric of my pants. Anne mewed like a kitten as she rubbed her bum along my zipper. She lifted her butt and resettled, so that she was higher in my lap. The tip of my rigid member would be piercing her pussy lips as she rocked back and forth if our clothes weren't in the way. All this while, Andy just drove. After a few miles, he spoke," I bet she'd like it if you played with her titties. That really gets her off. I hesitated, not really comfortable with the whole situation. Anne resolved my doubts though, grabbing my paws in hers and planting them on her bodice. "Ouch," she exclaimed," not so hard. You aren't testing melons." She again placed her hands over mine and spoke as she guided me. "Stroke them, and then squeeze softly. Start slowly. Yes, like that. Now spread your fingers wider and lift the weight of my flesh." She groaned loudly. "Now, now, now squeeze the nipple between your fingers." She was still bouncing on my lap, riding my cloth covered cock. "She can come just by having her tits played with," Andy explained. I had never heard of a girl doing that, but then, I was pretty inexperienced. "My panties are getting all wet. If I stain this dress, the party shop will charge me extra," Anne pouted. "Well, take the panties off, darling," Andy suggested. Since the costume came with ankle socks, it was simple and easy for Anne to obey. She nonchalantly tossed the wispy cotton drawers over the rear view mirror, and then settled back on my lap, rubbing faster. Without thinking, I began thrusting my hips up off the seat, matching her rhythm. She responded by pushing down harder. "This is almost as good as fucking," Anne sighed, her words now separated by moaning. "Your pants are better for me than a condom. The roughness rubbing on my lips is a special thrill." I thought I was about to blow my load in my pants. That never quite happened. Instead, Anne screamed, " I'm commmmmmminnnnng...." and collapsed back against me with final fierce wriggle followed by a triumphant giggle. Andy turned into the entrance of the gated community, coasting to a stop at a tiny guard house. Anne pulled herself together quickly, slipping back into the narrow middle space of the seat. I could tell by the guard's posture that he was unimpressed by the monster truck. Fortunately, as he stepped closer, I saw it was one I knew from visiting Sally. He was an old retired cop, who liked supplementing his pension. I also knew that he liked night shift because the lighter traffic left lots of time for him to nip at his flask. Tonight, his nose was glowing so red that if it was Christmas rather than Halloween, he could be Rudolph. "Oh, it's you, Tim. Here to see Sally?" He stared at Anne's tits, which were pushed up half out of the top, and had very apparent erect nipples. "Even though I know you, not supposed to let you in with being on the list." He waved a clipboard. "Especially tonight, what with the residents worried about outside rowdies party crashing." I was prepared for this familiar ritual. I reached into the pocket of my hoodie and pulled out a mickey bottle of rum. Reaching across, I passed it to the guard. With practiced speed, it vanished, hidden somewhere in his uniform. "I suppose since you are a good friend of Sally, I can make an exception for you. Your friends can't take this heap of steel in though." "That's fine", Andy replied, "We have our own party to go to anyway. We were just giving Tim a ride." I started to open the door, but first, Anne grabbed my arm and pulled me close. Her tongue pressed between my lips. My mouth opened a bit in shock, so she inserted her pinkness in past my teeth, her tongue wrestling mine. Her left hand held the back of my neck as she continued swapping spit for what seemed like forever. Finally, she came up for air. "See you soon, I hope," she breathed, exhaling slowly, slipping a note into my hand. After I climbed gingerly to the ground, I saw that the note was her phone number. Andy turned around, and tooted his horn gently. He leaned out his window. "I'd love to watch you finish what she started," he said just as he drove off. My cock pulsed in my pants, moving as vigourously as my hand waving goodbye. I was amazed by how this Halloween was unfolding, but for now I just shoved the note into a pocket and put the whole wild ride out of my mind. Sally was close by, and I felt ready to scale the Mount Everest of our attraction. Sally's house was behind the third green, a short hike from the entrance to the club. Still, I was wet enough that the breeze off the pond used for irrigation chilled me to the core. The wisps of fog in the crisp fall air added a somber tone, bringing me down from the thrill of riding with Raggedy Anne and Andy. My member though was still rigid. At least I was here almost exactly an hour after I spoke with Sally. That thought lifted my spirits as I lifted the ornate door knocker. I listened to the echo of the bong travel through Sally's father's tasteless tribute to newfound wealth. The developer could regulate the size and cost of the homes, but there was no governing good taste. The turrets and battlements were only appropriate once a year, and tonight happened to be the night. It looked every inch the Haunted House as I stood in the cold wondering whether I had missed Sally. Perhaps she had already gone to Chad's party, and my bad daydreams may be coming true. 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. Halloween Dress-up "Would you rather I just fuck you right here?" she growled. "Should I pull your clothes down and slide my cock inside you?" As perverse as it was, Sally's conduct sent shivers down my spine. I managed to shake my head, and to take each succeeding step more quickly until I was finally moving fast enough that my arms were stretched out far enough behind me that Sally's cock was not bumping me each time I climbed. "That's it, girly, shake that ass," Sally taunted me as I wriggled away, ever upwards. I was amazed to notice that my cock, rather than fading from disgust, was bobbling excitedly. I stumbled where the curve of the stairs shifted to the right, my nose ending up buried in the carpet, my body stretched out. Sally took advantage of the moment and pressed her entire body against mine from behind. She shoved her cock hard into the crevice of my ass, though my briefs prevented her from penetrating. Her breath warmed my neck, and then her moustache ticked my lobe as her tongue teased inside the ear. I tried to relax and just enjoy the pleasant parts, especially her heavy tits mashed against my back, although the layers of clothing diminished that sensation. "I think your ass likes my cock," Sally whispered. Until she said that, I had not been aware that my hips were indeed humping up off the stairs, meeting her thrusts. "We better get you dressed before your treat," she finally said, pulling back and roughly hauling me upright. I had always known Sally wasn't a small girl – her self-consciousness about her body was a reason she never dated- but her strength amazed me. This time, I needed no urging to climb as fast as I could up the rest of the stairs. Once we reached the landing, Sally deftly untied my hands and without a word propelled me into her bedroom. Which was right in front of us. She slammed the door behind me. Through the oak, I heard her say, "I'll wait out here until you are properly dolled up." The first thing I noticed was the outfit she had laid out fir me on the bed. It was a maid's uniform, in just the right classic cut and style to match Sally's gentleman butler- a soft dark fabric with a white collar cut in an only modestly revealing "V", and a knee length skirt. Much more the "Gosford Park" look than like a xxx movie French Maid. Beside the dress lay a strapless white lace bra and a matching pair of boy cut lace panties. "The panties are my stepmonster's...I thought hers might fit you better. Neither of you has any hips." Sally's deep tones rumbled through the closed door. Black stockings and a garter belt were also ready. I wondered for a second about the bra, and then saw the box of tissues perched beside the ensemble on the bed. I had never realized until now that my best friend's tits likely made her chest the same size as mine. A floral scent was wafting out of the en suite bathroom. I stepped over and saw that Sally had run a tub full of lavender bubbles. A razor sat on the shelf beside the old fashioned claw foot tub. I understood what I needed to do to wear the stockings. I quickly discarded the rest of my clothes and climbed into the warm water, enjoying the bubbles tickling my nose. I felt like a kid again. For a second, I wished that Sally and I were both four so that we could share the tub. Then my throbbing balls reminded me that sharing the tub with Sally all grown up would be much more fun. After we finished our treats, she likely would need another bath herself, and I planned to do my best to share it, although I realized that meant submitting to her will. A handy body sponge sat by the razor on the shelf. I soaked it in the foam. As I coated my body with soapy suds, I admired my own hard nipples bobbing at the surface. By concentrating on them, I was able just barely to rest stroking my cock. I knew even a modest touch might make my load explode out of the aching tip of my head. Sally would not like that. I lifted each leg out of the water, drizzling suds down the inside of my calves, letting the moisture trickle down between my thighs. This just forced me to look at my throbbing hardness. It looked larger than ever, perhaps a trick of the candlelit bathroom filled with mirrors. I risked brushing the underside of my manhood, fondling the soft flap of skin which linked the mushroom to the shaft. As my fingers rose up around the head, I detected a thin coating of precum leaking out. "Don't take all night, sissy, or I'll be forced to come in there after you," Sally shouted in her deep voice. I wished suddenly that I really was a girl, that I could pinch my nipples and pet my pussy until I climaxed, and still be able to recover and share sex with my master Sally. I slowly caressed my nipples, pretending that I had soft breasts, kneading my chest. In a trance, I lifted my right leg up onto the edge of the tub. Before reaching for the razor, I slipped my left hand along my side, caressing my body. My bum lifted up off the porcelain as my fingers curled around beneath me. My finger slid into my anus, piercing the sphincter ring with ease. I had never stimulated myself there before, but perhaps because of Sally's playfulness it seemed so natural. My cockhead bobbed above the surface of the water and a few drops of cum spurted out. I decided to hold off and focused on shaving my legs smooth enough to please Sally. Shaving my legs was not really very hard. The soap bubbles sufficed nicely to make the razor slide in even strokes up my skin. I was not very hairy to start with, so the tougher spots like knees and ankles were already pretty bare. I did get one tiny nick on my right shin, but otherwise, the work proceeded quickly. "Don't forget to shave your groin as well," Sally shouted through the door. This was tougher. My pubic hair was dense, and curly, and seemed to merge with the fuzz on my thighs and belly. I had to carefully lift my throbbing shaft up and away from my scrotum. If I wasn't careful, the handling itself would cause my load to erupt, thus frustrating Sally. As I gingerly eased the blade along my taut ball sac, Sally spoke again, "I'd come in and do it for you, but I want to see you all dressed up." I finished up by carefully trimming the hairs off my perineum, the little stretch of skin between my balls and ass. "I'm as soft and smooth as a baby's bottom," I told Sally. "Then dry off. Use lots of powder, so that the clothing slides easily." "What if I don't know how to put the things on?" "Just try." "Aren't you the 'there is no try, just do' Yoda chick?" Sally laughed in her normal manner, briefly reminding me of my gal pal. "They were sold out of that costume." The fluffy white towel was soft against my skin, but pearls of semen sprayed across its surface as I fondled my balls in folds of cotton. Satisfied that I was dry, I looked around the bathroom, only to discover that the single tin of powder was lilac scented. I hesitated, but I decided I had gone too far to disappoint Sally now. I sprinkled trails along my arms and rubbed it on my legs and chest. I was careful to coat my scrotum and cock without trigger an orgasm. "I don't hear fabric shimmying onto you tender young body," Sally called through the door, resuming her gruff manly tone. As I moved into the bedroom, I noticed a bottle of brandy set on the dresser, with a small glass. I quickly downed a shot to fortify my courage. I liked it so much I had another, and then another. "Us girls prefer crème de menthe," I giggled, warming to my role. "Hurry." I decided to start with the panties. They slid on easily, just like briefs, though my engorged cock could not fit in any way I tried. I did not attempt any more because my balls were drawing up inside my body, and the pressure in my shaft was threatening to burst. I just left the cockhead poking out of the waistband, which sank down to just above my balls. The bra was next. I had never put one on, of course, but had seen it done in the movies. I fumbled only briefly with the clasp. Since the cups were empty, it was not difficult to fasten the garment below my nipples. I struggled a bit with the straps, but wormed them over my shoulders more easily than I expected. A few handfuls of tissue and I was ready to admire myself in the mirror. Once glance told me that I looked fine for the current game, but that if Sally intended to take me out to Chad's party, she better help me put some makeup on. "Don't forget, I like full firm tits," Sally called through the door. I took her hint and doubled the stuffing in the bra. I then took a few extra minutes to shape and shift the mounds, so no tufts stuck out the top, but the curve, I hoped would look natural. In order to check, I slipped the dress on, despite not having put on the stockings. Although the fake cleavage had no nerve endings, adjusting my tits sent shivers through my body. I noted that the look of the dress was ruined by the tenting action of my erection. No matter how I waggled that, I just got more excited. If I kept going, I would surely stain the fabric. I sat on the edge of the bed and tried to figure out the garter belt, but no matter which way I looked at it, I knew I could never get it on. Around one thigh, maybe. "If the garter belt is a problem, don't worry, those are stay up stockings- Lycra is a wonderful thing," Sally said. I tentatively rolled a stocking up my left leg. As the strangeness faded the softness of the silk sent shivers again up my spine. With my smooth legs well shaved, I now understood how dressing up made girls feel special. "Are you ready?" Sally grumped from outside the room. I knew that just a Sally's moustache made her costume real, I needed a crowning touch. Sure enough, Sally had thought of everything. A blonde wig and a lacy maid's cap were neatly displayed on a vanity. I took a moment to settle these in place over my short hair, pausing only long enough to adjust the curls falling across my forehead. "Come and get your treat," I trilled, pitching my voice into a falsetto. I sprawled across the bed, one elbow propping me up, my legs crossed daintily, but my left leg crooked so that my skirt slid above the knee. Sally burst through the door, every inch the butler, and stood, hands on hips, admiring me. I know I blushed as she smiled. "You are a beautiful girl, but that lump under your dress has to go." With no further fanfare, Sally dropped to her knees at the end of the bed and flipped the skirt up above my waist. My cock surged vertically, despite the chilly air. It was fully exposed. Sally grasped the base firmly in her fingers and turned it about, admiring it. "This is beautiful too," she said, still using her mannish voice. The deep growl and the visual of the moustache hovering inches above my slit were odd, but the gentle pumping action of Sally's hand prevented any loss of erection. A few beads of cum tentatively spurted out of my cockhead, the rest restrained by Sally's grip. "I've always wanted to taste this," she said. She inched forward and lowered her head slowly, just barely flicking her tongue across the tip of my helmet, licking up the goo, and looked up smiling. Her teeth glinted with pearls of cum. The gob stuck in her whiskers made my squirm a bit. She rewarded me by giving my cock a rough squeeze. "Lay still and let me eat your overgrown clit," Sally demanded. I relaxed again; falling back on the mattress as she ran her tongue around the rim of my cock, then licked the whole head like an ice cream cone. She cleaned all of the precum off of it. Despite Sally's instructions, my hips had a mind of their own. They began bucking up off the bed, meeting Sally's lips, fucking her face. After the first few strokes, I no longer noticed the whiskers tickling. "Bad girl, getting so horny so fast," Sally said as she lifted her head. She reached over and slipped her hand under the edge of the top of the dress. She gave my nipple a twist until I yelped. Before I could respond, she again lowered her head over my cock, bobbing up and down the shaft with increasing speed. Her grip on my root never relaxed, so my sperm was trapped, urgently demanding an exit. "Have you ever done this before?" I asked, amazed that she was not gagging as my full length disappeared into her throat. In response, she twisted her head to signal "no". The resulting tongue whipping action around my shaft made the tingles run from my nose to my toes. I reached out. With my right hand, I found Sally's left nipple under her shirt. I grasped my own left nipple, massaging them both in stereo. Suddenly, Sally pulled back, a strand of cum forming a rope from my tip to her lips. Taking a fresh grip on my shaft, she pumped it harder, aiming the tip at her open throat. The first spurt of semen missed her mouth, striking her on the cheek, and getting caught in her moustache. Her tongue quickly flicked up to catch most of it. But I knew that as soon as she finished with my climax, she would expect me to groom her. I knew that's what maids are for. Sally had found her aim, and the second blast rocketed up to the roof of her mouth and from my reclining position, I saw the slimy cream slip back into her waiting throat. She briefly closed her mouth and rolled a ball of the goo on her tongue. Once again grasping my still full cock tightly, she shoved forward and forced her lips onto mine, forcing my mouth open. She swapped the snowball into my mouth and waited until I swallowed. "You are going to be a fine slut," she growled, "my slut." Then she slid down my body and took my cock back into her mouth. Several more shots of cum erupted into her throat, each one swallowed as if Sally hadn't eaten in weeks. The final drops leaked from the corners of her mouth. As my shaft softened on her tongue, Sally collapsed satiated to the floor. I decided to take a risk and act on my instincts. She did not complain as I followed, slipping off the bed to sit beside her. I carefully arranged the dress to cover my lap, and crossed my knees daintily. Gently, I took her chin in my hand turning her face towards me. She smiled dreamily. For the first time all night, I saw clearly my best pal behind the costume. I softly stroked the moustache with my finger tips, and then darted my tongue out, cleaning the bits of stray sperm. Sally shifted, and sucked my tongue deep into her mouth. After moments which seemed to last forever, she broke the clench. "That's enough tricks out of you, girly," she said, bit she was unable to stay in character, her deep voice breaking into girlish giggles. Her hand slid up my leg. "Oh, you're excited again already. We can't have you going to Chad's party like this." She lifted her hips off the floor and struggled out of the trousers, her underwear slipping off with the pants. Bunching my dress up at my waist, she bunny hopped on top of my erection. My rod slid effortlessly into the depths of her pussy. Sally used her legs to pump herself up and down my cock as my hips again showed a life of their own. I expected to encounter the resistance of a maidenhead, and paused in my response. Sally again was way ahead of me. "I lost that flap playing with carrots a long time ago, honey," she giggled. I felt like I was floating on a cloud, in heaven. The strangeness of our clothing no longer matter as Sally's fingers slid under us to milk my still swollen balls. My shaft throbbed, aching still from the last orgasm, but seeking more release. Sally's strong abdominal muscles began flexing in counter point to her up and down motion, wringing my cock. Shivers of excitement shot through my body with each twist. I seemed to drive up higher off the floor in response. Sally then in turn shoved down harder. I worked a hand between the buttons of her shirt and found her tit, massaging the meat first, and then touching the nipple, gently at first and then with increasing intensity. "Oh, gosh, that feels great," Sally moaned. She reached out and grabbed my other hand, sliding it around her ass until my fingertip pierced her sphincter. Now, my cock was ramming her cunt and I was finger fucking her ass as we bounced along the hardwood floor. The deep my finger sunk, the more Sally creamed with joy. While we fucked, Sally wrapped her fingers through my wig, and drew my lips to her mouth, kissing me deeply, sharing the remnants of my first load of cum. As we exploded in orgasm together, Sally held my face in her palms. I could feel her tears running down our faces. As Sally collapsed to the floor, we heard distant church bells tolling midnight. "I guess it's too late to go to Chad's party now, Halloween is over," Sally said. "Happy Halloween" I replied. Although I had yet to achieve my goal of seeing her nipples, it was the best night of my life. As she snuggled against me, I asked "are you sad you missed the party?" "No, I think my trick already earned me the best treat." Just then we heard the door knocker. "Trick or treat," we heard. The voices sounded like Raggedy Anne and Andy. Maybe they had figured a way past the gatehouse. Perhaps we would party after all. "Look at you, you're a mess," Sally scolded me. "Straighten up while I go greet our guests."