Halloween Cross-Dressing Bash Ch. 01

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Bob receives a cross-dressing invitation from Topsy Turvy.
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Part 1 of the 8 part series

Updated 10/21/2022
Created 10/15/2008
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Bob went to the bathroom, locked the door, and sat on the closed toilet lid. He pulled the invitation from his wallet and unfolded it. Well worn from reading it over and again so many times, he had saved it hidden there in his wallet and in his back pocket since the beginning of September. He had received the invitation online and printed it out before deleting it, so that his wife wouldn't see it.

It excited him to read it. It excited him to think about attending the Halloween party. Reading this 8 x 11 piece of paper was one of the few things that gave him any real happiness. This invitation to the Halloween Bash gave him hope for a new beginning and another chapter in his life with the hope of making some new friends who shared his interest and desire to dress as a woman.

"Topsy Turvy invites you to our biggest and best cross-dressing dance of the year, The Happy Halloween Cross-Dressing Bash. This is your chance to come dressed as you really are. This is your chance to be yourself without embarrassment or ridicule. This is your chance to fit in with the rest of us and to shine. So, kick off your jeans and flannel shirts and leave your work boots home. Put on a dress, a wig, some makeup, and your highest high heels and come strut your stuff with us while dancing to the music, Honey."

They got his name and e-mail address from the query he sent online last year. He wanted to go last year, but had chickened out at the last minute. He had reserved his place and ordered and even paid for the ticket. He even went as far as to pick out the clothes, but he left them in the carriage in the aisle when he saw his friend, Jim and his wife enter the store, as he was nearing the register to pay for his selections.

He panicked and left in a mad rush without them seeing him, thank God. That was all he needed was for Jim to see him buying women's clothes. That was all he needed was for Jim to tell everyone that he was a cross-dresser. He was a big blabbermouth and would tease him unmercifully not realizing that what he thought was a joke and was innocent teasing was, in fact, actually the truth.

He'd never live it down. Never again could he go to the tavern for a beer while watching the game on the big screen. Never could he shoot pool with the guys or be invited over to their homes for a game of draw poker. He'd have to quit the bowling league, too. And they'd never allow him to coach another Little League or Pop Warner Football team; two things that he loved to do every year.

He couldn't imagine what the guys at work would say. They'd think him gay. They would never understand his need and desire to wear nice things and to dress as a woman. They'd laugh at him. He couldn't imagine what his minister would say to him about this. His life as he had known and loved it in this little community of closed minded and unforgiving Christians would be over.

He imagined Jim's conversation.

"Hey, Bob, where's Sheila?"

"She's home."

"Home?"

"Yeah, I'm here alone."

"Alone?"

"Yeah, I thought I'd do a little shopping and pick up a few things that I needed."

He imagined his friend peering in the carriage and picking up his items, a dress, pantyhose, shoes, a pocketbook, a bra, and panty.

"What's all this? This dress is huge. It would never fit Sheila. Are you buying clothes for your mother or are you a cross-dresser?"

"No, uhm, it's for the women's shelter. Yeah, that's it. They are in desperate need for clothes for when they have to go out and get dressed up for a job interview."

He imagined himself turning red with embarrassment. With guilt and shame written all over his face, he imagined himself stuttering with nothing to say to make Jim believe that he wasn't a cross-dresser. What was the use? He knew Jim would never believe him, which is why he fled the store. His friend would immediately know that he was lying.

There'd be no way to explain himself out of that one because Jim's wife, Connie, was best friends with Sheila, Bob's wife, and she'd tell her that she saw Bob shopping for women's clothes. Then, when he didn't give his wife the clothes, Sheila, of course, would think he was having an extra marital affair.

He'd rather be deemed a cross-dresser than for his wife to think he was having an affair. He didn't know which was worse. Either way, she'd kill him. Either way, she'd divorce him. Either way, he was screwed.

He hated all the sneaking around just to buy an outfit for the Happy Halloween Cross-Dressing Bash. He had been so excited to attend and now to have all his excitement suddenly end was devastating. It was his fault. He hadn't really thought it through. What the Hell was he thinking shopping here in town anyway?

He should have shopped at a mall where no one knew him. Then, again, maybe he wanted to get caught. Maybe, he wanted all of this to be made public finally after spending a lifetime hiding the fact that he enjoyed wearing women's clothes. Maybe, he was just tired of not being himself and wanted to come out of the closet, so to speak.

So what if he enjoyed wearing women's clothes? He wasn't hurting anyone. He wasn't committing a crime. It was just something he enjoyed doing. People should mind their own business. How dare they put their morals and societal interpretations that forced him to conform to their standards and restricted him on how to act not only when in public but also even when in the privacy of his own home? He wished everyone would just leave him the Hell alone. This was his life to live and not theirs.

He'd even thought about ordering the clothes online, but what if his wife saw the credit card bill? What if the women's clothes came to his house when he was at work and his wife was home? How could he possibly explain that? Oh, my God! He was in a panic just thinking about what she would say and do.

"Bob, a box from He/She Outfits came for you while you were at work," he imagined his wife confronting him at the door with a rolling pin as soon as he pulled in the driveway with his pickup truck.

"What? He/She Outfits. I don't know what you're talking about." Deny, deny, and deny, he thought to himself when in a jam, even if she's holding proof. "I'm tired. I just want to get a beer and watch some TV."

"I should have known they weren't for me because you never buy me anything," she'd say showing her disappointment in that fact and in him. "Yet, I was so excited thinking that you bought me a gift and bought something for me that I opened the box. Can you imagine my surprise when I found these clothes? None of these clothes are my size. I take an 8/10 and these clothes are an 18. Can you explain this, Bob," she'd say holding up a dress that would surely swim on her petite frame, but coincidentally was plenty big enough to fit his fat body. "What the Hell is all this?"

"Explain what? There's nothing to explain. I didn't order that stuff. I don't know what you're talking about."

"Who did you buy these clothes for, Bob? Did you buy these clothes for your fat girlfriend? You'd better not have a girlfriend, fat or otherwise, Bob," he imagined her saying while tapping the rolling pin in the palm of her hand. "I won't tolerate you cheating on me after all I've done for you. I cook and clean for you and make you a good home. You'd better not have a girlfriend on the side."

"I have no idea what all these women's clothes are, Honey? I didn't order them," he'd say squeezing by her while pulling the dress from her hand.

Deflated that he'd have to return everything that he took the time to buy online, saddened that he now couldn't attend the Happy Halloween Cross-dressing Bash because he wouldn't have an outfit to wear, he imagined scooping up the women's clothes and stuffing them back in the box.

"What are you going to do with all this, then?"

"I'll return them tomorrow," he'd say going in the house. "Obviously, it was delivered to the wrong address."

He thought about opening a post office box and have whatever he ordered online delivered there, but he lived in a small town and he knew all those who worked at the post office and they were all blabbermouths. Even though he didn't understand why people thought that men wearing women's clothes was perverted, even though he didn't believe he was doing anything wrong by buying women's clothes and having them delivered to his house or post office box, the mailman knew all the perverts in town and he didn't want to be known as one of them.

He had spent many a day gossiping to the mailman about this one and that one and he didn't want to be the mailman's gossip fodder for the remainder of his route for that day and the remainder of the year. It pained him to think of the mailman gossiping to his neighbors about him being a cross-dresser because of what was delivered to him in the mail.

He just wanted to be left alone to live his life the way he wanted to live it, only he couldn't. People couldn't mind their own business. People were always pointing their fingers and laughing at anyone who was the least bit different. What the Hell did they know? They didn't know him? They didn't know how he felt? How could they? If they did, maybe they'd understand. Well, he was glad that he wasn't like them. He was glad that he finally found something that made him happy, even if he had to sneak around to enjoy it and even if it was considered taboo and/or perverted.

Now, a year later, back in a different woman's clothing store and shopping for women's clothes again, he was having a panic attack. He couldn't breathe. He was so nervous, so guilty, and so afraid to be himself. Wearing dark glasses and a baseball cap, always ready to abandon his carriage and flee the store, he continually looked around the small store to see if he recognized anyone shopping.

As soon as he grabbed a carriage and started shopping, his hands were shaking. Before he had picked out anything to put in his shopping cart, already, he feared taking his purchases to the register. As the anxiety that a thief must feel when about to shoplift, he felt as if he was doing something wrong. He felt everyone was staring at him. He felt everyone knew he was here buying clothes for himself. He felt that everyone knew he was a cross-dresser.

After not dressing as a woman for years, since before he was married, he had successfully fought the urge to dress up in women's clothes. Yet, always it was there. Once in a while he'd squeeze his fat ass in his wife's panties and wear them to work. Only, he always feared the embarrassment should he have an accident at work and have to be taken out by ambulance and driven to the hospital. He had women's clothes hidden all over the house, in the cellar, and in the garage when he needed to feel some comfort by wearing something nice, something soft, and something sexy next to his skin.

He imagined that the emergency medical technicians, doctors, and nurses at the emergency room saw it all, but this was a small town where everyone knew everyone and they all talked about everything to everyone. He could never live with that embarrassment and shame he'd feel should anyone in town discover that he enjoyed wearing women's clothes.

He'd have to move to get any peace after that. He'd be an outcast. He imagined the whole town turning against him and shunning him. He imagined mothers at Halloween pulling their children away from his house and passing it by completely.

"Don't go to that house for candy, kids. Bob lives there and he's a very sick man who enjoys wearing women's clothes. Pervert," he'd hear his neighbors yell when he came to the door with his dish of candy to pass out to the kids, only to watch them walk by his house before throwing eggs at his windows.

Even now, years later, he couldn't pass by a lingerie counter without feeling the silk and satin panties. He loved how they felt. Women were so lucky. He wished they made men's underwear that felt as nice and as soft and that made him feel as sexy when wearing it. He couldn't pass by a rack of women's clothes without pausing to browse the merchandise while imagining how he'd look in this dress or that blouse or that skirt.

Now, having given into the urge of wearing women's clothes, safe within the acceptance that he'd surely receive at the Happy Halloween Cross-Dressing Bash, he was excited about attending and getting dressed as a woman without being made to feel foolish or being harshly judged and meanly ridiculed. He just wanted to go somewhere that he could dress as a woman without anyone making fun of him or looking at him like there was something wrong with him. He just wanted to experience, for once, what it would be like to see himself in the mirror while being completely dressed as a woman in public. He wanted to be accepted for who he truly was without having to hide, without having to lie, and without having to make excuses for his behavior.

In the next chapter Bob goes shopping for women's clothes.

*

Thank you for reading my story. I sincerely hope you enjoyed it. Please take a moment to vote, make a public comment, and/or give me feedback. Your support is why I write. Your feedback will motivate me to write a better story the next time.

If you haven't already, please take moment to add me and/or this story or any other of my stories to your list of favorites. Thanks, Freddie, Bostonfictionwriter.

To be continued...

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  • COMMENTS
3 Comments
sharkjcw1sharkjcw1over 15 years ago
SUCKS!!!!!!!!!!!!!

TITLE SAYS IT ALL

AnonymousAnonymousover 15 years ago
Finally the truth comes out

And we find out why your wife threw you out. You're lucky she didn't cut your balls off too, or did she and that's why you're a whining, woman-hating asshole? Or are you just jealous of her?

AnonymousAnonymousover 15 years ago
The Truth

Nice to see that you are writing an autobiography.

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