The Halloween Party


Saturday, October 31st, 1998“So, is it possible to put this stuff on without opening your mouth?” Mitch asked as he delicately attempted to apply mascara to his eyelashes for the first time.“No, it’s not,” Heather answered simply from the bathroom doorway.  “Are you about ready?” she questioned. “We’ve been ready for thirty minutes.”“I’ve never done anything like this before.  I’m worried I’m going to look totally stupid,” Mitch responded.“Turn around, let me take a look,” Tracy encouraged as she stepped into the bathroom.  “You look great,” she said honestly. “A hell of a lot better job than I did the first time I put on makeup by myself,” she admitted. “You must have a natural instinct for it,” Heather added with a wink.Mitch rolled his eyes and tugged one more time at the little red dress he was wearing.  “This thing barely goes past my ass, everyone will be staring,” he complained.“That’s the idea,” Heather stated as she slapped him on the ass and started inspecting her own outfit in the mirror.  She adjusted her bow tie and smoothed the front of her tuxedo shirt. “Besides, welcome to our world. Guys stare at our asses every day.”“I should have never let you talk me into the dress,” Mitch argued.  “I should have just gotten a pantsuit or something.”“Hey, I wish I had legs as nice as yours,” Heather said, glancing down at his bare thighs and calves.  “If you’ve got it, flaunt it.”Mitch, Heather, and Tracy had all known each other since they were kids.  All three had attended the same high school, and all gone off to the same college as well.  As they had advanced through college, each one of them had progressed down a similar path of self-discovery. Tracy was a confirmed lesbian.  She had made that proclamation to the other two during their freshman year—neither was surprised.  Heather was confidently bisexual. Strangely enough, because of her short-cropped, spiky black hair, and her fairly strong feminist stances, many were actually surprised that she liked guys at all. Mitch was—well, Mitch was still trying to decide what he was. He supposed he was bisexual, but he would never admit that to his family, or anyone else back home.It was now their senior year of college and they were getting ready for a Halloween party.  A fairly large group of like-minded people had rented out a facility for what was sure to be a very interesting costume party.  The theme was “Gender Bender”. All the women were supposed to dress as guys, and all the guys dress as women.The two girls had difficulty getting Mitch to agree to go.  “Come on,” Heather had said, “No one there will know you,” she promised.  “And if they do, they’re going to be dressed just like you! So, who cares?!”After much encouragement, he had finally agreed.  Then came the hard part—actually picking out an outfit.  They’d taken Mitch’s measurements and went about finding an outfit that would show off all the right parts and hide all the wrong parts.  Mitch quickly discovered there was far more to it than just a dress and some makeup though. He also had to purchase a special pair of panties to help conceal what needed to be concealed, a fairly decent wig, and a pair of high heels.“Do I really need to buy all this stuff? Just for a one-time thing?”  Mitch asked.“Anything worth doing is worth doing right,” Heather had countered.  “Besides, who says it’s just a one-time thing? Trust me, once you go out like this once, you’ll want to do it again, and again.”“What makes you think that?” Mitch argued.Heather shrugged.  “Just a feeling.”So, with many reservations and much trepidation, Mitch purchased everything that Heather and Tracy suggested.  By the time every item had been purchased, Mitch realized he’d spent too much şişli escort money to back out of going to the party.The real moment of truth came about a week before the party.  Mitch was hanging out in Heather and Tracy’s apartment when Heather walked up to him with a package full of disposable razors and plopped it down in his lap.“Better get started,” she said.  “It might take you all damn week to shave.”“And trust me,” Tracy added, “shave now, so you can have some time to get used to it.  You don’t want your first hairless night to be the night of the party. Otherwise, you’ll probably be itching like crazy.”Mitch sighed.  “Do I have to?” he asked weakly, knowing the answer.“You do, unless you want to look like a gorilla in a dress next weekend,” Heather quipped.Now the big event had finally arrived.  It was the night of the party and the three friends had been preparing themselves all evening.  Heather had rented a tuxedo, complete with top hat, a cane, and tails. Tracy had opted for a tweed jacket and a bowler derby, her blonde hair tucked up underneath.“Here’s all that’s left,” Heather said, offering Mitch his wig.Mitch slipped the wig on over his hair, straightening it and fluffing it to the right shape with his hands.  As he did, he stepped back to examine himself in the girls’ full-length mirror. He raised his hands to his chest and adjusted his “boobs”.  They had decided that water balloons provided the perfect size and weight to make believable breasts.“You look stunning,” Tracy volunteered, “you really do.  Just don’t spring a leak.”“Thanks,” Mitch accepted the compliment awkwardly.  He wasn’t exactly sure how he felt about looking stunning in a dress and high heels.“Shall we go?” Heather prodded, gesturing towards the door with a white-gloved hand.The location of the party was just across the street and down the block, so the group had decided to walk.  “It’ll give you good practice in those heels,” Tracy commented to Mitch.“I don’t like this,” Mitch said, a note of apprehension in his voice.  “This is not exactly what I had in mind. I mean, we’re out in public, walking down the street.  Anyone could see me.”“Baptism by fire,” Heather said, casually swinging her cane around on the end of her hand and doing a little sideways dance step.  “Besides, if anyone sees you, they’ll just think you’re one more hot chick on her way to a Halloween party—which is exactly what you are.”“She’s right, you know,” Tracy agreed. “You look better in that dress than most women would.”They walked a few more steps in silence before Mitch sighed.  “Seriously, Heather, would you stop staring at them.”Heather and Tracy both giggled.  “Sorry,” Heather apologized, “you just really do have awesome legs.”“I’m so glad you convinced him to shave them,” Tracy agreed.“And his underarms,” Heather added.“Yes, and several other things too,” Mitch muttered.  With each step they took, Mitch could feel his knees beginning to tremble.  It wasn’t the high heels either. He was becoming extremely aware that he was wearing a dress—in public—and in a matter of minutes, he would be seen by dozens of people.“Come on,” Tracy encouraged, “Cheer up, this is going to be a blast.”“Yeah,” Heather agreed, “who knows, you might even meet someone.”Truthfully, Mitch had no idea what he was headed towards.  He essentially knew two things about the party they would be attending.  He knew that everyone would be crossdressed, and there would be copious amounts of alcohol.“So, how come Becca and Sadie are skipping out on this shindig, if it’s going to be such a great time?” Mitch asked, referring to each of the girl’s girlfriends, respectively.“They both had to go to work.  Neither one could take off,” Tracy explained.They mecidiyeköy escort arrived at the party in just a few minutes.  Heather opened the door for the other two. “After you,” she said with a grin.Mitch’s nervousness had reached its peak.  He felt a drop of perspiration roll down the interior of his arm.  His breath shortened and his heartbeat rapidly, as if it trying to jump out of his chest.  He reached down and very subtly checked once more, just to make sure everything was tucked away properly.They stepped inside and were immediately dazzled with an array of Halloween decorations.  Cobwebs hung at the entrance, tickling their skin as they entered, sending a chill down their back and legs.  Several Jack-o-lanterns were lit up in the entryway, greeting them with a big smile and a warm glow. Retro decorations hung on the walls, big cardboard vampires, and skeletons that glowed with the black lights and strobe lights.  Several fog machines provided a nice spooky atmosphere throughout the building. Techno music filled the air. As Mitch glanced around at the other party guests, much of his apprehension instantly melted away.  In front of him, he saw somewhere between seventy-five to a hundred people… and about half of them were dressed just as he was.  He knew he was amongst fellow travelers. These were like-minded people who weren’t going to judge him because he’d shaved his legs and was wearing a dress.“Here, have a couple of these,” Heather encouraged, as she handed Mitch two Jell-O shots.“I prefer beer,” Mitch said.“Oh, come now, a hot little number like yourself?” Heather joked, “gotta watch your figure.  Beer will make you fat.” She pushed the Jell-O shots into Mitch’s hand, and he immediately downed one of them.Mitch settled in and began to relax.  As he rested against the bar, or lounged in a chair, he couldn’t help but notice how many discreet glances he was getting.  Girls—or guys as the case may be—were checking him out—he found it exhilarating. The more it happened, the more he found himself mingling, walking around, and allowing himself to be seen.  As he strode across the room, he felt a confidence in his step that he had rarely ever felt on a day-to-day basis. To his surprise, he also caught himself checking out lots of other guys.  Wearing dresses and showing off their assets, they certainly caught his eye.  At one point, he attempted to force himself to focus on the many women wearing suits and ties, but for some reason, that’s not where his eyes kept drifting.  After much internal debate, he finally gave in and indulged in ogling the other men’s legs.Mitch had just approached a table, reaching for another Jell-O shot when a familiar voice said, “I’d recognize that face anywhere—even in a dress.”  Mitch stood erect. He would never forget that voice. The voice of the man he’d lost his virginity to.“Derek!” he shouted with genuine excitement.  A huge smile erupted onto his face.Derek returned the smile with a broad grin of his own.  “You look awesome,” he commented. “I wish I had your legs and ass.”Mitch paused for a moment and took notice of Derek’s own outfit.  He was dressed slightly more conservatively than Mitch was, but looked stunning just the same.  He wore a short-sleeve, little black dress that cut off at mid-thigh. Sensible heels that were shorter than the ones Mitch wore, and a very nice looking shoulder-length wig completed the outfit.“You look great too,” Mitch finally remarked after taking in his old friend’s feminine beauty.  “I mean, really great,” he added for emphasis, scanning down Derek’s figure one more time.“I think I’ll have a couple of those too,” Derek said, reaching for the Jell-O shots.  “Or maybe five or six,” he joked. They both helped themselves and moments later, threw the tiny empty cups into a nearby trash can.  “So, what are you doing here?!” Derek started in, and for the next few minutes, the two tried to catch up with each other. It wasn’t easy, as they had to talk over the driving rhythms and pounding bass of the dance music.Finally, after both realized the music was just too loud for a practical conversation, Derek asked, “Would you like to dance?” He motioned towards the small dance floor where many people were dancing to the upbeat music and having a good time.“I’m not much of a dancer,” Mitch said apologetically.“Oh, nonsense!” Derek yelled.  “There’s nothing to it! I’m sure you’re just as good as anyone else here.”  Without further argument, he grabbed Mitch’s arm and pulled him onto the dance floor.Mitch was tentative at first, but with Derek’s guidance and encouragement, he was dancing along with everyone else.  As he danced, a transformation occurred within him. Mitch’s confidence continued to soar, and he experienced a liberation that was quite exhilarating.  He began to lose himself in the moment. The more he danced and mingled amongst the crowd, the more feminine he felt. He was no longer just a guy awkwardly wearing a dress. He had embraced the role wholeheartedly.The music was an unusual mix of different varieties.  They danced to several songs before the two friends decided they needed a rest and drifted away from the dance floor.  Immediately, another “woman” came up behind Derek and wrapped his arms around him in a loving fashion.“Who’s your friend?” the newcomer asked in a good-natured tone.“This is an old friend of mine,” Derek replied.  “Mitch, this is my boyfriend, Tony. Tony, this is Mitch, I met him during my freshman year here.”Mitch shook Tony’s hand, and the two eyed each other up and down.  Mitch realized that he had already seen Tony earlier in the evening.  He had been one of several that had caught his eye. He even recalled seeing Tony on the dance floor, striking an incredible figure.  He was long and lean and with luscious legs and an upper body that looked spectacular in the white spaghetti-strap top he had chosen for the evening. The top cut off at his midriff, revealing a trim tummy with a belly button piercing. In the dark club light, Mitch couldn’t tell if it was real, or a prop for the party.  A pleated miniskirt flowed around his waist which, as Mitch had already noticed, was perfect for dancing. Tony’s wig was a short, curly blonde number. It reminded Mitch of Marilyn Monroe’s hair.After a few more introductory remarks, the three returned to the dance floor.  Mitch was surprised to find that he was actually excited to resume the dance session.  In no time at all, the three were dancing up a storm, along with everyone else. As they danced, Mitch couldn’t help but notice that both Derek and Tony’s dancing had become much more provocative—specifically towards him. At one point, he found himself sandwiched between the two of them, their bodies undulating with the pulse of the music. At another point, Tony spread his long legs, pushing his crotch up against Mitch’s thigh, grinding against Mitch’s bare leg.Mitch began to feel aroused.  However, it was not an arousal of his genitals, as he was used to experiencing as a man.  It was a deeper arousal, something more internal, like an underground spring rising from the depths of his being.  The throbbing rhythms, the strobing lights, the heat of dozens of bodies surrounding him, the half-a-dozen Jell-O shots—it all kindled this smoldering eroticism burning within him.He spotted Tony whisper something to Derek.  Derek glanced in Mitch’s direction with an impish grin, simultaneously biting and licking his lower lip.  Derek nodded his head in agreement. A moment later, Derek approached Mitch and whisper-shouted in his ear.