Using Halloween to Dress as a Queen


A time to wear a costume, Jerry uses Halloween as his excuse to dress as a woman.

Jerry loved October, his favorite month of the year, by far. The Fall was his favorite season, too. With the colorful array of leaves that crunched underfoot and the multi-colored canopy overhead, he loved the cool crisp air that made his nipples as hard as his cock. Whenever he went out for a stroll in the brisk October breeze to enjoy the Fall day, he enjoyed wearing women’s silk panties beneath his pants. The feel of the panty against his hairless skin was pure luxury and the freeing sensation of them helped him to pretend that he was completely dressed as a woman, even when he was dressed as a man. With every step he took, the feel of the soft material continually rubbed against the head of his cock helping to keep him hard.

It was fun being naughty without anyone knowing. Unless he was hit by a car, while crossing the street, no one would know, even suspect, that he was wearing women’s underwear. A man with a secret, a man wearing silk panties, it was his secret not to tell. Remembering what his mother used to tell him to always wear clean underwear, they may not be men’s boxer shorts, but at least they were clean, Mom.

Even though he was the youngest of three children, he grew up as the man of the house, after his Mom divorced his Dad. Jerry adored his mother. He loved his sisters. For him, cross dressing started so many years ago. Whenever his mother and sisters weren’t home, he had a complete wardrobe of their clothes to wear. He’s spent his teenage years serendipitously and stealthily sneaking around the house wearing his sisters’ and/or his mother’s clothes, whenever he was home alone. After his mother passed, he still cherishes a memory of wearing his mother’s panties to school on those days he didn’t have gym.

Now, living alone, after his marriage ended in divorce, too, he’s finally free to live his life in the way he wants to live it. Maybe it was the leaves turning colors, before falling to the ground, but he somehow viewed his life much in the same way. As if he was an artist using a kaleidoscope of color in his new, sexy makeover, as if he was a chameleon changing color to compliment its background, in his case from male to female, as if he was a circus clown with a different colorful costume for each skit, not that he was clownish in any way, although there’d be some who think him a clown or worse for having the incontrollable need to dress as a woman. Nonetheless, as if shedding his skin and transforming his persona in deference to his inner beauty, as a caterpillar metamorphosing into a beautiful butterfly, spreading his wings to allow his feminine spirit to soar, he changed from a man to a woman with the season.

“Viola! How do you like me now?”

The makeover from within, from inside out, instead of outward in, was dramatic and dynamic. He talked like a woman. He walked like a woman. Even without his hair, makeup, and clothes, one could see that he was a woman beneath the man. He looked like a woman.

Changing himself to become his wished for identity and his preferred for gender, it was no one’s business what he did in his private life; that was personal. He was outraged when men questioned him, made him feel bad, and pried into his private affairs, whenever suspecting he was a cross dresser. These were the same men who never should throw stones at their own glass houses, while going to great extremes to keep their personal business secret; he never understood the difference. Why should he confess his innermost secrets when they don’t share their dirty little secrets? We all have skeletons hiding in our closets, don’t we?

When those men, who laugh and point at him, divulge all the strip clubs they visit on their long, liquid lunch hours and all the extramarital affairs they have when they lie to their wives and tell them they were working late at the office, is when he’ll broadcast to everyone that he’s a cross dresser. Until that time, they could all go and fuck themselves. Yet, except for those who have seen him perform in drag, few know his secret that’s he’s a cross dresser.

Even though he was a cross dresser, when he was dressed as a woman, he didn’t feel that he was a man cross dressing to look like a woman. He truly felt like a woman. Because he was a small man, barely 5’7″ levent escort tall and nudging 140 pounds, his dimensions were closer to female than they were to male. All his friends were 6′ and taller and most weighed over 200 pounds. They all dwarfed Jerry, that is, until he did his hair up and wore his high heels. Then, he was spectacular.

As if readying for the prom, as if readying himself to attend a debutant ball, he spent weeks readying for the Halloween costume parties that he was invited to and excitingly attended each year. Recently paid to perform, Halloween costume parties not only served as his coming out party in his need to dress as a woman but also fulfilled his need to sing, dance, and entertain, all while making some extra money, enough to pay for his extravagant costumes. He’s even given more than a few one liners to some drunken bashers in the audience. This year, he had received invitations to three Halloween parties, a record number, one Friday night, one Saturday night, and befitting Halloween, this year, one on Sunday night, October 31st.

In previous years, the most Halloween parties he was ever invited to and attended were two and, in this tough economy, an expensive proposition to host with all the food and drink, he was surprised that people still celebrated Halloween with a party. Maybe because Halloween fell on a Sunday this year, with the full weekend to prepare for and to celebrate the holiday, people were more apt to take advantage of the holiday by having parties. Besides, a time of the year that darkness falls over celebrations and holidays and people start to contemplate and dread a long, cold winter, if it wasn’t for Halloween, other than birthdays and anniversaries, there’d be little to celebrate between Labor Day and Thanksgiving.

He wished for the time when he’d have multiple Halloween parties to attend in a day. Much like the Christmas season that starts the day after Thanksgiving and runs through to New Year, he wished Halloween had a prolonged season, too. Wishing he lived in Salem Massachusetts, where they festively celebrated Halloween every day the entire month of October by dressing up and walking around in costume in public, maybe he’d take a vacation there next year.

Then, he thought of Elvira, Mistress of the Dark. Boy, if she wasn’t a woman, she’d make for a great cross dresser. The first time he saw her, he thought she was a cross dresser. She had her year round, Halloween spook movie night. Also, playing year round Halloween costume dress up, there were the fictional freaky Munsters and the Addams Family of television and movie fame. He yearned for a place and a time where he could live as a women every day. Wow, he’d finally be free. He’d finally be at peace. Finally, he’d be who he was always meant to be.

Even though dressing as a woman wasn’t Halloween scary, albeit maybe it was to some, he thought, while laughing to himself, he wondered how he could make more use of the Halloween holiday to his personal advantage. As an entertainer, a singer, a dancer, and an amateur comedian, he wondered if he could make a year round business out of attending or throwing Halloween parties. When the holiday was more about wearing a costume, why must Halloween only be on October 31st? If it was up to him, Halloween would be every day. With Halloween his pretense and his reason for him to play dress up and cross dress, he loved dressing as a woman.

Halloween was the one time of the year that he could be the woman he always wanted to be without feeling self-consciously uncomfortable and guilty. As far as most people were concerned when they saw him, he wasn’t as much in drag, as he was in Halloween costume. As far as he was concerned, he was the woman he always wanted to be, while still being the man that he’ll always be beneath the clothes, the hair, and the makeup.

“Trick or treat.”

Halloween was his special holiday and his special day that he didn’t feel the embarrassment and the shame that he always felt before, when he hid his need to cross dress by hiding in his house. Finally, brave enough to go outside, whenever he ventured out of the house dressed as a woman, he spent more time feeling conspicuous and feeling like the monster that he wasn’t than he did enjoying his moment, as the woman he always wanted to be. His beyoğlu escort excuse and his reason, should he bump into someone he knew, a friend, an acquaintance, or a relative, whether they were dressed up as ghost, a hobo, a witch, or a goblin, was that he was going to or coming from a Halloween party. Halloween was the day we all dress up as someone or something else, anyway, and it was the day that he dressed up as a sexy and desirable women.

Even though dressing as a woman was a charade, he was tired of the charade. He wished he didn’t have to hide behind Halloween, as his pretense to be himself and who he truly was, a woman trapped in a man’s body. He envied women and wished he could dress as a woman all the time, and not only when in costume on Halloween. For the sake of others having something to say about what he did and when he did it, it wasn’t fair that he was so tortured and unable to live his life the way he wanted to live it without having to endure all the stares and acrimony.

Yeah, sure, he could say fuck them, but the question was, did he believe it and the truth was that he didn’t because he spent more time being too preoccupied, consumed, and concerned with the perception that other people had of him. Why was that? Why should he give a care about them and how they felt, when they didn’t give a care about him and how he felt?

Maybe that was the reason why he was so endeared to certain female celebrities, who really could say fuck you and mean it, Bette Midler, Cher, and Madonna, immediately sprung to mind, along with Christina Aguilera and Lady Gaga. They all danced to a different drummer and they all stayed true to themselves. Truly, they didn’t care what others thought of them. They needed to be who they were and they did. Because of those women is why he’s the man that he is by becoming the woman that he so needs to be.

“Fuck them!” There, he felt better saying it and meaning it. “Fuck them! Fuck them! Fuck them! Who the fuck do they think they are? This is my fucking life. Fuck them!”

Wow. Save the anger, hold it, and then let it go. Even though it’s there, always there, just beneath the surface, he finally felt free. Free to live his life the way he wanted to live it and to do whatever he wanted to do.

“Yeah, baby!”

He loved wearing sexy under things, bras, panties, slips, corsets, stockings, girdles, and garters beneath his clothes. His dead giveaway that he was a man dressed as a woman, besides his Adam’s apple, was that he dressed better than and, if he’d say so himself, looked better than most women his age. Most women don’t know how to put on makeup. Generally, in two groups, those how put on too much and don’t who don’t put on enough.

Most women don’t know how to make the most of what they have. He did, of course, not having any female body parts, what he could do with makeup was artistically amazing. Most women his age, more comfortable in jeans, sneakers, and a sweatshirt, give up and, unless they have money, no longer take the time and the expense to properly care for themselves. He put those women in a non-gender category. Dressing more like men than they dress as woman, when wearing jeans and a sweatshirt, unless it’s a tight sweatshirt and the woman has big tits, that sloppy attire does nothing for their sensuality, sexuality, and femininity.

More comfortable with applying makeup than he was with applying quick set cement for a building project in his backyard that he doesn’t want to do and keeps procrastinating doing, he loved dressing as a woman. He loved doing his hair, a wig actually, and doing his nails and makeup. He didn’t even mind so much shaving all the hair off his trim and fit 5’7″ body, that is, except for all the itching, when it all started growing back the very next day. If he was really a woman and had estrogen instead of testosterone, he wouldn’t have to shave all the places that he shaves now. He could only imagine the time he’d save.

As if shopping for Christmas gifts for others, he spent the entire month of October shopping for the right outfits for the Halloween parties he’d attend. Shoes were important. It was always difficult finding a shoe wide enough and comfortable enough to wear. Always, he’d have to jury rig it somehow to expand the width and find a softer pad to put inside kağıthane escort as a cushion. Still, he couldn’t wait to go shopping. He hasn’t been this excited since he was asked to perform in front of a live audience dressed as Cher.

He always wanted to sing, but he never had the talent or the voice. Yet, he had a knack and the ear for impersonating the voices of others. Weird. Just as weird that he could impersonate the voices of others, it was weird that he was unable to find and develop his own singing voice. Always he was deemed a better singer than he was, when he copied the sound of someone else.

That first night at the karaoke bar, after he found the courage to perform with more than a few drinks giving him the who cares attitude, his friends thought it was a joke and that he was kidding when he told them that he could sing just like Cher, that is, until they heard him sing. Then, every time they’d go to the karaoke bar to drink, they’d pressure him to get up on stage and sing. Always, he stunned the crowd. Always, he received the biggest round of applause and for the rest of the evening, he didn’t have to buy another drink. People continued coming to his table buying him drinks and asking him to sing this song or that song, as that singer or another.

“Jerry, you sound just like Cher, better than Cher. It’s unbelievable. If I close my eyes, I’d think you were her. Do Bette Midler.”

Only, for him, it wasn’t the same show visually and he didn’t derive the same pleasure from doing his female singing impersonations, unless he dressed up as the person he was impersonating. Even then, especially then, he’d never felt comfortable enough to dress up as a female impersonator and impersonating a celebrity in front of his friends. Without doubt, even though he’s a straight man, loves women, and never even contemplated having sex with a man, his friends would think him gay. They just don’t get it. They just don’t understand. It’s hard being friends with someone, who really doesn’t know who you are. Certainly, he was tired, so very tired, of pretending to be who he wasn’t.

It’s bad enough they joked around with him calling him a female impersonator and a drag queen, if only they knew his secret. If they only knew that he was. If they only knew he loved cross dressing. Fearing that he’d want to have sex with him, clueless and ignorant, they had no idea.

If they only knew he wished he were born a woman. If only they knew he was wearing silk panties beneath his pants and a nightgown to bed every night, they’d be his ex-friends, instead of his friends. His real friends were other cross dressers. They knew what it was to have that incontrollable need to dress as a woman and what it felt like to have that overwhelming feeling of being so pretty when they did.

Nonetheless, he wasn’t committed enough to becoming a woman by having a sex change operation. He liked his penis and having sex with women too much, and a sex change operation was a step that he was unwilling to take. Besides, he wasn’t gay and wasn’t looking to have sex with men. As much as he loved dressing as a woman, he loved women too much, which is why, perhaps, he impersonated them so well.

For sure, he never wanted to have sex with a man. He wouldn’t mind having breast implants, though. That would be cool to have his own breasts instead of having to wear a padded bra with silicon falsies. He could only imagine the pleasure he’d feel jerking off, while feeling his own tits. Also, it would make him happy to take just enough female hormones so that he wouldn’t have to shave as much hair, as often as he must shave it off his hairy body. The preparation for his male to female transformation was the real time consuming pain in the ass.

It’s funny how most of the women he could impersonate went by one name. Beginning to build quite the repertoire, he had a list of women he could do, Cher, Streisand, Celine, Madonna, Christina, Aretha, Whitney, Mariah, Shania, and Beyonce. Then, there were the more recent female singers, Bette Midler, Lady Gaga, Carrie Underwood, Dolly Parton, and Taylor Swift. Yet, Britney, because of her sexy antics and in the sexy way she dressed, was the most outrageous fun. Dressing up like her with a short skirt and pigtails, while dancing around the stage, was always a good time. He felt the most like a woman, when doing her.

A celebrity impersonator, who used impersonating celebrities to cover his cross dressing, it was his way to feel free. Yet, confined to the month of October and mostly to Halloween, his freedom was short-lived, which is why he loved October and which is why he loved Halloween parties.