Halloween Cross-Dressing Bash Ch. 02

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.

Finally, there was a place for him to go where he'd feel accepted. The Topsy Turvy Happy Halloween Cross-Dressing Bash, run and organized by cross-dressers for cross-dressers, he'd finally meet men who were just like him and who shared his need to dress as a woman. There was nothing else like it and he couldn't wait to go. Tickets were $30.00 a person and the invitation even read that he could bring his spouse or girlfriend or significant other to the event. Only, he had no one to bring. He was alone in his secret.

He envied those men who had a woman by their side who understood their need to cross-dress. His wife would have a heart attack if he told her that he needed to dress as a woman. She'd never attend if he asked her to accompany him and would forbid him to go. She'd think he was insane and she'd divorce him for sure if he dressed and attended the event.

He hated the fact that he couldn't share something this big, something that was so important to him, and something that made him this happy with his wife. He hated having to sneak around. He hated feeling so guilty. He wished he could tell her. He wished she'd be supportive of his need to cross-dress. He felt so alone safeguarding his secret desire. Happy and excited, he was sad and guilty at the same time. He was miserable.

When they went to New York City, last year, they had seen a few cross-dressers and drag queens and she laughed at them and made fun of them to him.

"Bob," she said squeezing his arm. "Look at that one. That's a man dressed as a woman, isn't it? How can someone so sick walk around like that in public? I'm so embarrassed for him. He looks nothing like a woman. It's so obvious that he's a man. He's not fooling anyone. What a bunch of faggots."

Her hostility towards them shocked him. What would she think of him if she knew that he shared their desire to dress as a woman? Would she think he was sick? Would she be embarrassed for him? Would she think he was a faggot, too?

He thought the cross-dressers looked pretty. He envied how they looked. He wished he were one of them and was free to be himself. He envied that they were so dressed in women's clothes and out walking about on a public street, when he was still hiding his secret desire to so dress. He wished he could be as brave and as true to himself as they were. He wished he was as free to express himself in that way.

She made him feel bad. She made him feel perverted. She made him feel dirty. She made him feel less than the man he truly was. She made him feel that he was a degenerate just because he wanted to feel feminine and pretty. There was just no way he could tell her, never mind asking her to attend the Topsy Turvy Happy Halloween Cross-Dressing Bash with him. He imagined the fight they'd have and her respect he'd lose.

"What? You want to dress up as a woman? You want to drag me to this perverted and sick dance with you? I'd be mortified. I'd be humiliated. Are you crazy? What is wrong with you? What are you gay? I married a gay man! I want a divorce."

He imagined her thinking that he suddenly lusted over men and not understanding what cross-dressing was about. Not necessarily sexual, not necessarily even a fetish or homosexual, cross-dressing, a behavior of transgender, does not always mean that the cross-dresser has a different gender from that assigned at birth. Only, how could he convince her of anything in her state of close mindedness?

She was as close minded about it, as were most people. She'd never understand. She'd hate him. She'd be hurt. She'd feel that she did something wrong. She'd feel that it was her fault that he wanted to dress as a woman. She'd feel it was all about her and not about him.

Bob didn't want to shock anyone. He didn't want to challenge social norms. He wasn't trying to make a statement. He didn't even want to pass as a woman by adopting her voice or mannerisms. By keeping his mustache and not shaving it off, without even realizing it, if anything he was genderfucking. He didn't even know what genderfucking was.

He was just an average guy who enjoyed the feeling of women's clothes against his skin. He liked how he looked when he was all dressed. That's all. He felt pretty, he felt sexy, and he was happy, and he only wished that he could experience that feeling more often.

Bob hid the bag of clothes away in the toolbox of his truck while waiting for his wife to go out and do her errands before bringing it in the house. He was excited to see his purchases again and to try them on to see if they all fit.

He was sweating he was so nervous. He had never done anything like this before and he was embarrassed, but excited at the same time. The saleswoman at the store, an attractive and heavyset woman, who was about his age, wouldn't leave him alone. He didn't know if she was hitting on him, was just trying to do her job and help him, thought he was a shoplifter because he was acting so nervous to arouse her suspicions or if she suspected that he was buying the clothes for himself and that he was a cross-dresser.

He figured he was just being paranoid. He figured she was just doing her job. He needed to calm down, relax, and have a good time picking out the outfit he'd wear to the ball. This was the beginning of a new chapter in his life.

He successfully avoided her by heading down different aisles whenever he spotted her heading in his direction. Then, as she neared, he tried not looking at her hoping that she'd head the other way and busy herself with another customer.

"Can I help you to find something?"

"What?"

"Do you need some help with sizes?"

"Oh, well, yeah, I think, uhm, maybe. It's my wife's birthday and—"

"What size does she take?"

"Size? Oh, I don't know. I didn't think to take her sizes with me. She's big, as big as I am." He was glad he didn't say as big as you are. Some woman, all women probably, are sensitive about their weight.

The saleswoman looked at him with a knowing look and he felt embarrassed. Was she looking at him because he was a typical guy who didn't know his wife's sizes? Was she looking at him because she could tell what size his wife would take by the size of him? Was she looking at him because she thought he was a potential shoplifter? Or was she looking at him because she suspected he was a cross-dresser. His palms were sweating and his pulse was racing. He figured she thought that he was a cross-dresser. Suddenly, he felt exactly how he hated others made him feel. He felt perverted.

He felt as if he was doing something wrong and maybe he was, but it was none of her business why he was there. As far as he was concerned, he was there to buy clothes for his wife. As far as she was concerned, he was just another customer with every right to be in her store to shop for whatever and for whomever.

He took a breath and tried to relax. He wanted to tell her that the clothes weren't for him, but he figured that would make her even more suspicious. Yet, what did it matter? He'd never see her, again. He traveled nearly clear across the state on the pretense of going to a monster truck show to shop for women's clothes. No one knew him here, he hoped.

"Well, if your wife is as heavy and as tall as you are, you'd want to go to the plus sizes that are on the other side of the store. These are the petite sizes."

Bob stood 5'8" and weighed about 200 pounds.

"Oh, okay."

She escorted him to the other side of the store and now that he was relaxed enough to take note of the woman who was helping him, he determined that they were both about the same size. She was pretty, much prettier than his wife. He felt better knowing that she could help him pick out the correct sizes he needed without making her think that the clothes were for him. Maybe, she'd even try the clothes on to model them for him.

Nah, she'd never do that. It's probably against store policy. Besides, this wasn't Rodeo Drive. This wasn't a high end store where they had models to model the clothes while you lounged in a chair sipping champagne and comfortably waited for your wife or girlfriend or significant other to make her fashion selection and she wasn't Pretty Woman.

Suddenly, being in her company, he was horny. The more he interacted with her, the more he was attracted to her. Nonetheless, he felt conspicuous and uncomfortable being the only man in a woman's clothing store. Finally, he felt relieved when he saw that there were other salesclerks helping customers, too, and not just helping him. That made him feel better that he wasn't being singled out, but it was just store policy and helpful store clerks helping customers find what they needed.

"Are you shopping for pants, a skirt or a—"

"A dress," he said with a nervous smile. "She only wears dresses. She said that pants make her look fat and that dresses hide her weight more."

"Yeah, that's true, normally, but we have some slenderizing pantsuits that just came in for our Fall selection and they go on sale—"

"Nah, she'll return it if I bought her pants. She never wears pants."

"Well, I have several racks of dresses. Do you know what colors she'd like? Does she like solids or prints or—"

"Solids and in a dark color, black, navy blue, brown or forest green because she says the darker colors make her look thinner."

She rifled through a rack and pulled out half a dozen dresses. Every dress was more than he wanted to spend. Some of the dresses were well over one hundred dollars, more than he paid for the last suit he bought to attend his friend's wedding.

"All of our dresses can be altered. We have a seamstress—"

"I like this one," he said pointing to a dark green one that had shiny gold buttons. He didn't even look at the others she had pulled from the rack. He acted as if he was afraid to even touch any of them.

"You have good taste. This is a popular style and a very comfortable dress. Many of our customers choose this dress because it is roomy without looking baggy," she said twirling around with the dress held up to her before holding it up to him. Being blessed with abundant proportions, she was very curvaceous for a full figured woman. "And it just falls right because of the material," she said. "And the gold buttons dress it up a bit otherwise it would look a bit plain."

"It's not for me," he said taking a step back. "It's for my wife."

"I know that," she said giving him a sexy smile and a chuckle. "I'm just holding it up for size," she said taking a step towards him, "since you told me that your wife is about your size."

"Oh, okay. I'm just a little nervous being in a woman's clothing store without my wife. I'm more comfortable in Home Depot shopping for power tools," he said with a laugh.

"We are about the same size. Is your wife about my size?" She gave him a smile before slowing turning in each direction. Bob couldn't help but stare at her big breasts. They were huge.

"Yeah, she is, only she—" he paused embarrassed while holding his hands out in front of his chest and staring at her huge double D breasts. Certainly, she could suffocate someone with those weapons, but what a way to die. He imagined her hanging those huge hooters down over his face and sucking on them while she sat on his cock.

He imagined the conversation that his friends would have at his funeral should he meet with foul boob play.

"So, how did Bob die, anyway?"

"Bob was suffocated by big boobs, really big boobs, the lucky bastard, but he died with a smile on his face."

"Wow! What a way to go. When I die, I hope I go that way, with big boobs, really big boobs, suffocating the life out of me."

She looked down at her abundant cleavage before looking back up at him and catching him looking at her tits and giving him a sexy smile.

"Not many women are as top heavy as I am. It's been a curse more than it has been a blessing. My husband left me for some flat chested bitch. Can you imagine passing up a steady diet of these big tits," she said raising her tits up with both her hands, "for a woman who has not much more than nipples?"

Top heavy? He didn't know why this woman didn't continually fall forward from the weight her her huge hooters.

"No, I mean, yeah, he'd have to be crazy to pass up on those. Sorry," he said feeling a bit uncomfortable with the conversation and her forwardness. "I didn't mean to stare." He could feel his face turning a bright red.

Now, he was unable to remove the image that she had given him of her standing next to her ex-husband's flat chested girlfriend with her big tits casting a shadow over her feet. He imagined the two women standing side by side topless. It took all the control he had to wipe the smile from his face imagining her big, naked breasts.

"It's okay," she said. It's been years since we divorced."

Still holding the dress up to him, she pressed one hand against his chest with her other hand pushed against his pelvis with her fingers only inches away from his cock. If he took one step to the left, her fingers would be in contact with his growing erection. There, he did, but just as he did, she handed him the dress. Darn.

"Thank you," he said accepting the dress from her.

"You can return it if it doesn't fit her. We can go a size smaller or a size larger. We have some in a size 16 and a size 20. And if she doesn't like the color, but likes the style we have the dress in brown, black, navy, and red. I'm sure she'll love it."

Bob looked at the price, $89.95. He could buy a nice fishing rod or a power tool for that. He calculated that his entire outfit he was wearing today, jeans, flannel shirt, work boots, and even his underwear didn't cost as much as this one dress.

"I can try it on for you, if you'd like and model it so that you can see how it would look on your wife."

"Really?" He couldn't believe his ears. Suddenly, he imagined her whipping off her dress and putting on this one right in front of him. "You can do that?"

In the next chapter Bob enjoys the show.

*

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To be continued...