NOTE 1: A thank you for my passionate and thoughtful editors: Steve B and Estragon.
BECOMING MY COSTUME: HALLOWEEN TRAIN
I moved to a new school this fall and, although I was pretty crazy in college and am rather dynamic in my classroom, I am pretty shy and reclusive with my colleagues. I was the only new teacher in the school and I just didn't seem to fit in. The only other new person was an intern named Heather. We went out for drinks a couple of times, and had shared some rather naughty sexual secrets while intoxicated, but had not really hung out more than after-school drinks. Then out of the blue she invited me to a Halloween party. Sick of being alone marking History papers, I figured I might as well go.
I should note I love Halloween. My craziest sexual encounter occurred on Halloween when my boyfriend at the time actually penetrated me while we were standing in line for a movie. I was panty-less, as my boyfriend always expected me to be, and the line was packed tight. He draped his sports jacket over his arm and I felt his hard cock on my thighs, so although nervous as hell, I spread my legs, attempting to give him access. He only got the wide mushroom head of his cock in me before the line started to move, but it started a night of firsts.
During the movie, a showing of Rocky Show Horror Picture Show, I sucked him off and swallowed the first of two loads he would fill me with. After the show, he fucked me on the hood of his car and came in me as two peeping Toms watched. I noticed them but, instead of being mortified, it seemed to turn me on. I put on a very naughty show for them, talking dirty and doing porn star moaning. It was my one act of crazy-out-of-character sex I ever had, and was always the one recurring fantasy I jilled off too late at night when I was all alone in bed. But I digress ... the point is I love Halloween. I get to dress up and be someone other than myself. In the past I had been a French maid, a naughty nurse and a sexy cowgirl. Yet, when I learned I was going to a party with a bunch of strangers, I decided to play it safe and ended up going as an angel, dressed completely in white. I had the halo, the conservative dress, the white pantyhose and the three-inch white heels.
Heather picked me up, dressed in a slutty Robin outfit from Batman and Robin that barely held in her ridiculously large breasts. The skirt also barely went mid-thigh, and she chuckled when she saw my outfit. "Why didn't you just go as a nun?"
I stammered, now feeling silly, "I don't know anyone at the party and didn't want to come off as slutty."
Heather smiled as she led me to her car, "Oh don't you worry, they will all know you by the end of the evening."
At the time the statement seemed odd, but in retrospect it was an incredibly subtle hint of what was in store for me. We did the usual chit-chat work bullshit on the drive, while I tried not to stare at her perfect breasts. In comparison to my 34b breasts, hers were Amazon-like. I should note, in full disclosure, I am very bi. I had a few lesbian relationships in my past, again mostly college, but had a six month relationship with an older teacher at my last school that ended poorly, leading me to switch jobs. And although it had been six months since I had touched a man or a woman, suddenly my wanton desire was becoming harder to ignore.
We arrived at the party. As soon as we entered the house, a mansion really, I felt out of place. Not only did I not know a single person here besides Heather, every girl I saw was dressed as if they were about to be filmed in a porno scene. There was the slutty pirate, the slutty mermaid, the slutty flapper, the slutty cop, the slutty nurse, the slutty Cinderella, three slutty Lady Gaga's and, of course, the slutty school girl. The women's ages ranged from early twenties to over forty.
Heather grabbed my hand, intertwining her fingers with mine, which surprised me and gave me a slight tingle down below, and led me to a beautiful redhead. The redhead was introduced as Amy and she was the hostess of the party. Her green eyes were hypnotizing and my tingle down below began to distract me. The redhead was dressed as a real slutty version of Pebbles Flintstone. She put her hand out and said, "You must be Mandy. I have heard very good things about you."
"You have?" I stammered, stunned that Amy would have talked about me to her.
"Oh yes," the redheaded Goddess smiled, "she said you would be a perfect fit for our group."
"Oh," I replied, confused.
Before I could get any clarification, another woman, dressed as the mandatory slutty maid, came over and pulled Amy away.
I turned to Heather, who was still holding my hand, and asked, "What group?"
"Oh, just the people here. She is very selective in who she invites into her home. Thus I had to vouch for you," Heather explained, squeezing my hand just a bit.
Feeling a bit lucky and decadent, I thanked the younger intern, "Well, I am happy you thought of me."
The next twenty minutes I was introduced to over thirty people and had two glasses of wine before I was introduced to Amy's husband, dressed not surprisingly as Bam Bam Rubble. He went to kiss my hand all suave-like, and spilt a whole glass of red wine on my pure white costume.
Within seconds, Amy was over and pulling me away. "I am so sorry Mandy. My husband is a klutz at the best of times, never mind when he has had a few drinks in him."
I attempted to explain that it was no big deal, but before I knew it, I was in a massive bedroom, a room that was truly bigger than my whole apartment. Before I could even say how gorgeous the room was, the pretty hostess had my dress off. "Shit," she muttered, "the wine went through and onto your bra." In the blink of an eye, she had unclasped my bra. Just as quickly she was gone and I was alone in white panties, pantyhose and heels in a stranger's bedroom. Instantly a chill went up my back and I was shivering. Against my own wishes, my nipples perked up and I attempted to cover myself while I waited.
Amy returned and said, all apologetic, "I am so sorry about that. Now let's get you a new costume." She shuffled through her closet and sighed. "Unfortunately, I am a bit larger than you, but my daughter may have something." She handed me a robe, which I quickly put on. She grabbed my hand and led me to another large room, although this one was not as big as my apartment. She let go of my hand and, after much snooping, came back with a school girl's uniform and a cheerleader's outfit. "Well, the choices, I am sorry to say, are rather limited."
I joked, trying to put some humour into the situation, "Well, at least I will fit in with the rest of the costumes now."
She laughed in return and suggested, "Well let's try the schoolgirl look, shall we?"
I shrugged, thinking why not?
Her sweet tender voice asked me, as one would ask to pass them some sugar for their coffee, "Please take off your robe, Mandy."
Not feeling at all self-conscious around this stunning woman, which was odd for me, I took off the robe.
The older hostess surprised me when she commented, "I would die for your legs, girl."
"Thanks, I always considered them my best asset. I wish I had breasts like you," I replied, attempting to return the compliment.
"Are you kidding me?" she responded, "They are too big. My husband treats them like fucking basketballs and no matter how much I workout I can't prevent the inevitable sag." The surprises continued as she took off her flimsy tight costume. Underneath her costume she was only wearing a white thong.
I saw little evidence of sagging and could feel my mouth watering at the thought of them in my mouth. I questioned, trying not to stare at these large breasts, "What sagging? Those look pretty perfect to me."
The big-breasted hostess moved directly in front of me and surprised me yet again. She grabbed my right hand and placed it under her left breast and assisted me in cupping her breasts. "See, they sag."
Mesmerized by the breast in my hand, I mumbled, "They seem pretty damn perfect to me."
Still holding my hand to her mouth-watering breasts, she complimented, "You have perfect little titties, Mandy."
Not used to such flattery over my most insecure body part, I blushed and sputtered, "Thanks, but they are so small."
Her right hand went to my left breast. An uncontrollable soft moan escaped my lips at her sudden touch. Her smile broadened and she explained, "They are the perfect size. Not too big, not too small. A perfect handful." She squeezed my breast gently as she finished speaking. I desperately wanted to feel her lips on my erect nipples. Instead I was brought back to reality. Her hand left my needy breast and she noted, seemingly concerned, "It must be freezing in here. Your nipples are as hard as diamonds. Although the costumes we have probably won't warm you up much. " The domino-chain of surprises continued on this roller coaster ride of teasing. The beautiful and almost completely naked redhead dropped to her knees and I instantly felt a shiver flow through my whole body and a little juice leak out of my very wet pussy. I instantly worried she would be able to smell my naughty scent. She asked, "Lift your foot up, honey."
I obliged, and she unbuckled the straps on my high heel shoe. Once my first shoe was off, she took off my second heel before complimenting, "What cute toenails."
I loved the compliment. I always had my hands and feet perfectly manicured and had done them today, painting them a ruby red, a small contrast to the all-white outfit I had worn. It was my small, but subtle, hint at the naughty side that lay dormant inside. "Thank you, I just had them done today."
Reading my mind, she noted, "The red is quite a contrast, my dear. A naughty little contrast." I blushed. Still one her knees, in one quick lightning flash, she grabbed my pantyhose tops and pulled my pantyhose off. "You won't be needing these anymore," she nonchalantly said and tossed them to the side. She lingered, her face close to my very excited pussy before standing up. She grabbed the schoolgirl blouse. "Unfortunately, I don't have a bra that will fit you, so you will have to go braless."
Speaking for the first time in a while and attempting to hide my horniness and nervousness, I joked, "How 1960's."
She handed me her daughter's school uniform blouse. While I buttoned the somewhat tight blouse on me, I watched Amy grab the skirt and reposition herself at my feet.
Suddenly the door opened and I jumped startled and embarrassed by the perception of how this would look. Heather walked in and said, a look of shock on her face, "Oh sorry, I am obviously interrupting something."
Amy quickly explained, "Don't be silly. We are just getting a costume for our new friend."
Heather closed the door, an odd smirk on her face I couldn't understand, "I brought some more wine. White this time," she joked.
I quickly finished buttoning the blouse and lifted my feet up so Amy could pull the skirt up. Once dressed, Heather handed me a full glass of wine, which I quickly half downed, my tipsiness becoming more apparent.
Amy stood up and looked at me. "You definitely need the knee-high socks."
"For sure," Heather concurred.
Amy went in search of the socks while I continued to drink my wine. "She's awesome, isn't she?"
"Yes," I agreed, "She is very open."
"You don't know the half of it," Heather replied, her tone oddly foreboding.
"Found some," Amy announced, breaking the odd moment Heather and I were having. She handed them to Heather, who took them and, without a word, dropped to her knees and began to put the socks on me.
I protested, "Heather, I can do it myself."
Amy spoke for Heather, "No, no, no. Heather will do it for you."
I watched, almost detached from reality. Was this really happening? And what exactly was happening? The last twenty minutes had been all surreal and dripped with unspoken sexual innuendo, but Heather on her knees dressing me upped the ante. From my standing position, I had a bird's-eye view of Heather's ample cleavage. Her breasts and the third glass of wine, which I had just finished, had me thinking naughty, naughty thoughts. My increasingly wet pussy also gave away the impact the odd situation was having on me.
I began to fantasize diving between Heather's barely covered tits when I was brought out of my mischievous daze. "Hello, Earth to Mandy!"
"W-w-what?" I stammered, briefly confused.
"I said, you look really adorable," Amy repeated, and pointed to the closet mirror.
I looked at myself in the mirror and barely recognized myself. "Wow," I muttered out loud.
"Wow, indeed," Heather commented, her voice sultry sweet. "But..." she added.
"But what?" I asked, suddenly self-conscious.
"You need pigtails," Heather announced.
"Brilliant!" Amy enthusiastically agreed.
I stood like a statue as Amy grabbed a couple of elastic hair bands and quickly put two pigtails in my shoulder-length, light brown hair.
Backing up to get a full look at me, "Now that is perfect."
"Agreed," Heather concurred, "Plus, they will make great handlebars."
Amy burst out laughing, "That they will."
"Handlebars?" I asked, feeling completely out of the loop.
Heather smiled slyly, her foreboding tone back, "You'll see soon enough."
Just as I was about to ask what that meant, Amy confused me even more by moving towards me and kissing me. My body melted at the touch, remembering how good it was to be kissed, and I didn't even hesitate to return the kiss. I opened my mouth and felt Amy's tongue slide into my mouth. The kiss, gentle at first, slowly escalated to reckless passion. Without breaking our lip-lock, Amy slowly pushed me backwards and onto her daughter's bed. Once on the bed, Amy broke the kiss, her big breasts now directly in my face, and offered, "Go ahead, baby, I know you have wanted to suck on them for a while now." I leaned forward and took her left breast into my salivating mouth. Amy moaned, "That's it baby, suck on my titties." I licked, sucked and nibbled on her breasts, eager to please. She pushed my head back on the bed and pressed her breasts back in my face. Although slightly suffocated, I continued to explore Amy's gorgeous mounds of flesh.
While my face was buried, I suddenly felt my skirt, well Amy's daughter's skirt, being pulled off me. I lifted my ass up to assist with my undressing. Now naked from the waist down, I vaguely heard Heather say, "Holy shit, her pussy is soaking wet."
Amy pulled her breasts away from my mouth and looked me directly in my eyes. "Is that true, baby, is your pussy all wet?"
"Yes," I moaned, feeling my legs being pushed apart.
Asking a question I am sure she already knew the answer to, "What got that sweet pussy of yours all wet?"
"You," I moaned again, feeling lips kissing my inner thigh.
"What about me?" she asked, beginning to unbutton my blouse.
Wanting to please her, to compliment her, I answered in complete honesty, "Everything. You're lovely breasts, your sexy voice, your tender touch and your open demeanour."
"My lovely breasts," she repeated, "I have had them called lots of things before, but lovely breasts is a first." My last button was undone and Amy opened my shirt and said, "Do you want me to suck on your lovely little titties?"
"Desperately," I moaned, feeling Heather's hot breath just inches from my already leaking pussy.
"Do you want Heather to lick that sweet pussy of yours?" Amy asked leaning forward and taking my erect right nipple in her mouth.
Another moan of pleasure escaped my mouth and I whimpered, "Yes."
Taking her lips off my breast, Amy said, "Well, then just ask her then."
Amy returned her attention to my breasts and I nervously begged, "Heather, please eat me."
"Eat your what?" Heather teased, her hot breath now directly on my pussy.
Desperate to be touched down below, I begged, "Please eat my pussy, my cunt, my hole. I am begging you."
"If you really want it, you are my pet tonight." Heather surprised me, before her tongue did one quick lick on my hard clit.
"What?" I moaned, a mix of erotic pleasure from Amy's mouth on my breasts and Heather's brief tease on my pussy.
Amy interjected, "You see, my dear, this party is our annual Halloween swing party."
"Swing party," I repeated, stunned.
"Yes," Amy explained. "And you see, every year a new guest is invited to be the special entertainment for the evening. Last year Heather was the special guest. This year it is you!" Amy returned to my hard nipples.
"Me?" I asked, in a state of complete bewilderment.
Amy released the nipple that she had between her teeth. "You indeed, and I think Heather made an excellent choice. You see, last year Heather was brought by Allison, who was the special guest the year before. Next year it will be your duty to bring a special guest if you want to become a lifetime member to this and other special gatherings."
She again returned her attention to my sensitive nipples. I moaned and tried to process all that I had just learned. My mind was a haze of drunkenness and horniness, neither a very good state to make logical decisions in. I repeated, trying to comprehend, "I am the special guest?"
Heather licked my pussy for a few seconds before quitting and answering, "Yes, you are the special guest." She slid a finger easily inside my dripping wet pussy and asked, "Do you want me to make you come?"
Without even a second of thought I begged, "Please Heather, eat my pussy."
"You mean your cunt, right?"
Thinking it was just semantics and both words were rather naughty and inappropriate, I repeated what she wanted to hear. "Yes Heather, please eat my wet fucking cunt."
"You'll be our special little plaything tonight?" Heather asked.
My pussy aching for attention, her finger still lodged in me, but not moving, I declared, horny to do just about anything, "Yes dammit, I'll do whatever you want tonight, now please eat my fucking cunt. I am so horny I am about to explode."
Heather, finally content with my answer, dove into my dripping cunt and began licking me while she also began to finger-fuck me. The double sensation, triple if you include Amy's tender playing of my breasts, was too much and in only a couple of minutes of concentrated attention to my wanton cunt and I was screaming like a nasty whore. "Oh my fucking God, that feels so amazing. Don't stop Heather, keep licking my cunt." Heather, clearly aware of how close I was to an orgasm, my first orgasm with another person in four months, slipped a second finger in me with surprising ease, and began pumping my cunt while sucking on my swollen clit.
Unlike many women who can only come once, my first orgasm usually takes a while and then they come fast and furious. So although my moans were loud and I was loving every minute of Heather's clearly experienced tongue, I knew I was still a while away from an orgasm ... but I was wrong. Heather sucked my clit into her sweet little mouth like she was a fucking Hoover vacuum and hooked her fingers inside my fevered cunt and found my long lost g-spot. I instantly screamed, "Oh, my bloody heavens, I'm comingggggg." My legs tightened around Heather's head as I gushed like a broken faucet all over her pretty face.
Once my orgasm had subsided, my next one was already lingering, when Heather pulled herself up and out from between my legs. Heather, her face literally glistening from my juice, smiled, "Fuck! You come hard."
Amy sat up also and I shrugged, "Once I start coming, it takes forever to stop."
"That will surely be tested tonight," Heather predicted.
In the heat of sexual bliss I had forgotten that I was some sort of special toy for the evening. Amy handed me another glass of wine. I quickly shot half of it. Amy looked me over for what seemed like forever before she decided, "I think the cheerleading costume will be better for the rest of tonight's entertainment."
"Agreed," Heather responded with a nod.
Unlike the erotic sexual undertone tease of my first dressing, this time Amy and Heather dressed me with systematic precision.
When they were done, I looked in the mirror. I was wearing a red and white cheerleading outfit, with white thigh high stockings, clearly in view with such a short skirt and my hair was still in pigtails. I looked fucking hot.
"You are good enough to eat," Heather commented and added, a sexy smirk on her face, "again."
Amy chuckled, "Time for the main attraction."
"Indeed," Heather smiled, taking my hand.
Although nervous and full of angst, I allowed myself to be led into the sexual unknown. A small tinge of trepidation was easily overtaken by the excitement I was feeling. My pussy was still soaking wet and I was revved up for more.
Once back downstairs, I quickly realized a lot had changed. Now I didn't walk into a full-scale orgy or anything, but things had apparently started to get a lot looser. A guy dressed, as I think, an eighties pimp was fucking a girl dressed as Marilyn Monroe and the girl in the slutty Cinderella costume was sucking on a big black cock, which was attached to a guy wearing some sort of medieval costume.
I was led to a chubby, but very pretty, woman dressed in a Batman outfit that was a size or two too small. She also was wearing a strap-on dildo around her waist. I assumed this was the afore-mentioned Allison, and soon learned I was right.
"Good choice, Heather," the chunky brunette complimented.
"Thank you, Allison," Heather replied, before introducing me, "and this is Mandy."
The strap-on cock-wearing Allison took my free hand and said, "It is a pleasure to meet you." Her smile dripped with sweetness, her cock poking me ever so close to my still fired up pussy.
I blushed, "it is nice to meet you too."
"Are you ready for a fun night?" she asked, with a suggestive smile.
"I think so," I stammered, extremely nervous, as I looked around and felt more than a dozen sets of eyes boring into me.
"Come with me," Batwoman said, taking my hand. I followed her and she took me to a quiet area of the house. "What is your fantasy?"
"What?" I asked, surprised by the question.
"Well, you are the special guest and many men and women here are salivating with the thought of using you, but we do like to attempt to make some naughty fantasy of yours come true."
"Oh," I said stunned, "I don't know."
"For example," Allison explained, "Two years ago when I was the special guest I received my fantasy of being used as a personal sex-toy for a younger couple. Last year, Heather's fantasy was to be the centerpiece of a lesbian orgy."
"Oh my," I whispered, a naughty fantasy flashing in my head.
Allison's noticed my smile and asked, "One popped into your head didn't it?"
"Yes," I said, suddenly ashamed.