tagTranssexuals & CrossdressersCross Dressing for Valentine's Day

Cross Dressing for Valentine's Day


This is a Valentine's Day contest story. Please vote.


First time in public, Frank attends his first cross dressing Valentine's Day party.

Frank was online surfing the web, when he stumbled upon a site pertinent to him. He couldn't believe what he was reading. He had no idea such a thing existed. He pushed the button on his computer to print it and to post it up on his refrigerator, so that he wouldn't forget the date.

'Come one, come all, come in drag, come with a friend, or just come stag, but this is our yearly Valentine's Party for Cross Dressers.'

He was so excited. A Valentine's function just for cross dressers, he never knew such social functions existed. Suddenly, as if a whole new world opened up to him, he felt relieved, revived, and rejuvenated. He felt normal. He felt ready to finally emerge out of his self-imposed closet and socialize with men who shared his secret love and need to dress as a woman.

Frank was a cross dresser, only no one knew it. Managing to keep it hidden, he had been cross dressing for thirty years without anyone knowing, not even suspecting, that is, except for his wife. She knew and they discussed it openly, after she discovered his secret. Even though she was understanding of his reasons and accepting of his need to wear women's clothes, he could tell that she didn't approve, an understatement. She became cold and distant, after his confession.

Although he tried and successfully hid it from her for years, it was inevitable that she'd discover his secret. How could she not know? Happy that she knew and that his secret was off his chest, her finding out, no doubt, was probably the reason for their eventual breakup and divorce.

Maybe because he was tired of hiding it, maybe because he wanted people to know, it had become increasingly difficult to continue to hide his secret. One day he forgot to remove his fingernail polish, when he went to work. He discovered he was still wearing nail polish, when he was already in the car and driving to work. Once at work, he rifled through his secretary's desk drawer to borrow and put back her nail polish remover, before she came in to work.

Over the years, he's had some close calls that surely would have made his secret known to friends, family, and acquaintances. Tired of the nerve racking panic attacks, he wished he could live his life in the way he wanted to live it without having to hide and sneak around. Only, this time, with this cross dressers' Valentine's Day party, was different. For the first time in his life, he wanted the world to see what a pretty woman he made.

It wasn't so much the attention that forced him to go public, he was tired of hiding. He wanted to be free from all the secrecy and the circumspection that he felt from others. He needed to be accepted for who he was, a man who enjoyed wearing women's clothes.

So what? What's the big deal? He wasn't a serial killer, he was just a woman trapped in a man's body and he wanted to live life in the way that he wanted to live it, without people thinking him mentally ill, weird, or a pervert and making fun of him.

For once, instead of wearing his mother's clothes, instead of wearing his ex-wife's clothes, instead of wearing his daughter's clothes, he wanted to buy his own first outfit, something that he had chosen himself and something that was his. He wanted to wear something that more comfortably fit him. For once, excited about the Valentine's party, he wanted to look as pretty as he could. Wanting to finally publically experience his feminine side, he wanted to look his best.

Only, how could he do that? He was terrified of walking in a women's clothing store and shopping for what he needed to buy to look how he wanted to look. Walking through the aisles and looking at all the pretty things, if he wasn't a cross dresser, he'd have no problem shopping in a women's store for clothes for his girlfriend, wife, or significant other. The fact that he was a cross dresser heightened his paranoia and made him feel that everyone was staring at him and that everyone knew his secret.

Maybe some were staring at him and others knew his secret, so what? What did it matter? Yet, what wouldn't have mattered to others mattered to him. After spending a lifetime being teased and ridiculed because he was different and was never one of the regular guys, he spent his life avoiding those painful situations. Putting himself back in situations that caused him emotional distress brought up too many painful memories that he worked so hard to forget.

Then, what if he needed to try something on to see if it fit and how it fit. In a woman's clothing store, there was no place for a man to try on clothes and even if there was, he'd only be calling more attention to himself, attention that he didn't want or need to have. If he took the chance and just bought the clothes, it would be a pain to have to return it without making more of a perceived spectacle of himself. No doubt, after returning the clothes, the customer service employees would remember him, watch him, and whisper about him, the next time he came in the store to shop.

Even though he tried to make himself believe that the people laughing at him behind his back didn't bother him, it did. He couldn't do it. He just couldn't put himself through all of that emotional trauma again. The negative way that people perceived him and treated him ruined what should have been an enjoyable experience.

His decided transformation began when he discovered a group of men online that not only celebrated cross dressing but also celebrated themselves during the most difficult of times, the holidays. With many of them divorced and living alone with their secret, they were tired of being an outcast and a public joke, ergo the reason why they were reaching out to one another. Much in the way that swingers, who were in the swinging lifestyle, had dances and house parties, this group of cross dressers had social functions for Halloween, Christmas, New Year's, and Valentine's Day. They were even in the early stages of planning a combination pool party and barbeque for the fourth of July celebration. Wow! Finally, there was some place for him to go to feel normal and to be accepted for who he was and not to be laughed at because of what he needed to publically wear.

So excited and relieved that there were other men out there, just like him, he never knew something like this even existed. Filled with guilt all his life, even though logically he knew better, he stupidly thought that he was the only one needing to dress as a woman to show his feminine side and inner beauty. The fact that he could finally meet other men just like him, men who needed to dress as a woman, and talk to them and socialize with them, while dressed as a woman, would finally set him free from the need to hide his secret. Even though he was nervous about attending the cross dressing social function, he couldn't wait to attend the event.

He joined the cross dressers' computer site by setting up a profile and logging in with his e-mail address; his log in name was Roberta. Where other men picked exotic women's names, such as Tiffany, Crystal, and Veronica, he wanted something he'd remember and not stumble over, if when nervous. Since his name was Robert, Roberta made sense. He didn't particularly like the name, but it wasn't as much about what name he used. Rather it was more important that he'd be socializing with men who were much like him.

The problem in finding clothes still existed, however. Literally, he had nothing to wear. All of his women's clothes were mismatched and when worn together, he looked as if he was a Salvation Army reject. Yet, now that he had a cross dressing resource, perhaps a member had a suggestion where to buy all that he needed to wear.

Because of how close he lived to the store, one online member, who went by the name, Samantha, directed him to a special women's store, where he wouldn't be hassled and/or embarrassed in buying his first outfit. Instead, he'd be helped to make the right decision. The store was just downtown and he went there after work. It was a small dress shop with a couple of customers inside and an older woman, his age, behind the counter. As soon as he entered the store, she gave him a look of recognition, as if she knew he was a cross dresser.

He felt small. He felt embarrassed. He felt conspicuous. In the look that he incorrectly perceived she gave him, he felt the same way he felt, when his mother caught him wearing her clothes, so very long ago. He wanted to bolt, but willing to face whatever painful embarrassment that he must endure to attend the cross dressers' Valentine's Day party, he didn't bolt. Thinking about the reason why he was there, thinking about the cross dressers' social function, he held his ground. Besides, he was directed here and was told that she was accepting of cross dressers.

"Hi, may I help you?"

"Samantha told me to--"

"Hi, I'm Rosalyn," she said immediately appearing as if she recognized the name he gave her, as if he had given her a secret code. She offered him her hand with a smile.

"Bob," he said returning her smile with his handshake.

"I have customers, Bob, but why don't you go across the street and have a cup of coffee. I'll be closing in just half an hour and I can help you in privacy then," she said with a smile. "Okay?" She patted his hand in the way his mother used to and that one action made him totally trust her with his secret. Still so very nervous, he felt somewhat relieved that she was a newfound friend.

"Sure," he said happy that he wouldn't have to be embarrassed with other customers staring at him, wondering about him, and gossiping about him.

He went across the street for a cup of coffee and a slice of apple pie. Then, when he saw her put the closed sign in the window, he went across the street and knocked on the door. Immediately, she opened the door and let him in.

"Let's go in back," she said with a smile. "I put out some things you might like."

He followed her to the backroom and sure enough, she had put out a complete outfit that appealed to him. With green his favorite color and that color complimenting and enhancing his hazel eyes, the dress was a forest green and there was a coordinating belt, shoes, scarf, and pocketbook. He was amazed. He couldn't have chosen a better outfit had he walked around the store for an hour. Moreover, it was all his size, a size 8. She only saw him once for less than a minute, how did she know his size?

"This is perfect," he said looking up at her with a smile, before looking back down at the clothes. "I can't believe you knew my size just by looking at me."

"Well, if you were a woman and weren't so broad shouldered, you'd be a size 6 with your small frame," she said.

Usually, he'd take offense, when someone called him small. A lifetime of teasing from his classmates and neighborhood thugs, he now accepted who he was.

"Even so," he said. "I couldn't have chosen a better outfit," he said picking up the dress and holding it up to him, while looking in the mirror. "I just love the color."

"My brother was a cross dresser and he went through holy Hell trying to hide his secret, even I didn't know his secret for years. I was the first person he trusted enough to tell," she said with a sad smile. "Then, when his so called friends discovered what he was hiding, they made his life a nightmare with all the mean spirited teasing and public embarrassment and humiliation."

"So, what happened? I mean, how did he get through all of--"

"He didn't. He committed suicide."

"Oh, I'm so sorry."

"Don't be. My brother is finally free and in Heaven. He was my best friend and with him sharing his secret with me, I used to help dress him. Later, he helped me to buy this dress shop. Because of all that he had to go through and deal with, in his memory, my shop is a safe haven for cross dressers. I met a lot of his friends and they were the best people I've ever met and still are my best customers. I never met a cross dresser I didn't like. All of them are friendly, sensitive, intelligent, and creative. I wish he had a crossing dressing group to turn to in the way that you do now but, a time before computers in the Internet, they didn't have anything like that."

"What do I owe you for the clothes and accessories?"

"Don't you want to try on the dress?"

"If you don't mind, I'd rather try it on at home."

"Sure, no problem. I understand."

"Well, everything, the dress, the shoes, the handbag, the scarf, as well as all the costume jewelry comes to $330.00."

He gave her his credit card and she bagged everything for him. Then, when he was getting ready to go, she handed him a big box.

"What's this?"

"These were some of my brother's things. As soon as you walked in my store, I did a double take. I thought for a second you were my brother returning from the dead. You look like him and are the exact same size. There are dresses, shoes, and handbags in the box. You're welcome to them. I rather give them to someone who could use them. Whatever you don't want, you can donate to a homeless shelter."

"Thank you," he said taking ownership of the box. He was so excited that not only did he buy his first outfit but also he had an entire box of clothes that would fit him.

With the night of the cross dressers' Valentine's Day party quickly approaching, he was excited, but nervous. A good way to ease him out of the closet and to admit his secret to others, he never would have gone out in public dressed as a woman, if he didn't have this cross dressers' social function to attend to ease him out of hiding. He only wished he had someone to go with, instead of going alone. Not the most outgoing person, he knew he'd have a hard time mingling and making friends. He figured he'd spend the evening sitting alone, sipping a beer, and watching everyone else having fun. A lot of these functions are obnoxiously clicky with men, no doubt, whispering about others, in the way that women do about other women.

Something he didn't think of before, he realized now. Dressing up as a woman in a room full of men dressed as women, would they be looking to see what he was wearing, how he applied his makeup, and did his hair? Wanting to look good anyway, suddenly, he felt pressured to look perfect. Accustomed to not fitting in a man's world, he didn't want to be an outcast in a cross dressers' world, too.

If he was going through all of this trouble, time, effort, and expense to dress as a woman, he wanted to look like a woman. The last thing that he wanted to look like was a man dressed as a woman. For him, that would never do. The one thing in his favor was that he was small, barely 5'6" tall and weighed a slim and trim 135 pounds. Wanting to be a jockey as a boy, he never thought he'd grow this tall. Up until his early twenties he was 5'3" and 110 pounds. Then, he had a sudden growth spurt that summer that made him look more like a man than a boy.

In readiness for the cross dressers' Valentine party, he'd shave everything and pluck everywhere. He'd take the time to get his wig, just right, washing it and blow drying it, instead of wearing it in the way he usually does, like a stiff hat. He took the extra time to read some makeup tips by the professionals. Only, the makeup part of it was tricky. Other than applying lipstick, which he did that wrong, too, he was lost. With his eyes tearing and his hand jittery, it was impossibly difficult to keep his eye open, while applying his eye makeup. He didn't know how women did it.

With the big Valentine's party looming, ready to give up and not go to the party because he looked more like a punk rocker or a Goth girl than a beautiful woman, he called Rosalyn for help. Maybe she'd do his makeup. Only, she had a better suggestion.

"Hi Rosalyn, it's Bob. The man you gave your brother's--"

"I remember you Bob. How are you?"

"I'm great, thank you."

"How did the dress fit?"

"Perfect. That style looks really good on me, too, and I just love the color. Green is my favorite color."

"And my brother's clothes?"

"I love them all. Thank you very much," he said feeling an uncomfortable silence and suddenly feeling pressured to speak. "I need help with my makeup and I was hoping that--"

"Say no more. I know the perfect woman to help you. Her name is Linda and she works out of her house. She can do your makeup for you. It won't be cheap, though. As part of her service, she'll hope you'll buy her products, but she'll teach you how to correctly use them and apply them. Part of her service is to put on your face."

"Great," he said.

She gave him her phone number. Hoping she could take him a few hours before the Valentine's Day party and apply his makeup for him, that would work perfectly, if she could. As nervous as he was when going to the dress shop, he felt the same butterflies of dread in his stomach, while thinking about going to Linda's house to have her do his makeup. He knew if he was this nervous about going to the dress shop and now to someone else to have his makeup done, he'd be a nervous wreck when walking in a room full of men dressed as women at the Valentine's party. Yet, if he didn't go through all of this, in preparation for the cross dressing party, he'd regret his indecision the rest of his life.

He dialed Linda's number.


"Hi, you don't know me. My name is Bob and Rosalyn--"

"Hi Bob. I know all about you. Rosalyn just called me to tell me you'd call."

"Well, that's a relief that I don't have to go through an explanation," he said with an uncomfortable laugh. "There's this Valentine's party Monday night, Valentine's Day, and I was wondering if--"

"Sure. What time is your party, Bob?"

"It begins at 8pm," he said.

"Why don't you come to my house at 5pm. That will give us plenty of time to talk, apply your foundation, and put on your makeup."

Foundation? He didn't even think about foundation. He was glad he called her. She gave him her address and, as if this was the first real step in his transformation, he went there as excited as he was going to the dress shop and as exciting as he was anticipating going to the party. It was one thing for him to buy his own clothes, but having someone to teach him how to apply makeup and use a foundation was more of a serious step in cross dressing.

Eager to get dressed and to show Linda how he looked, especially after she put on his face, he wore his new clothes to her house. Only, when he saw all that she needed to do to apply his makeup and with the distinct possibility of her getting makeup on his dress, maybe he shouldn't have worn his dress. Not to worry, she put a towel around his neck and shoulders to protect his clothes.

Now, wearing his pretty green dress, coordinating, shoes, handbag, scarf, and jewelry accessories, and having Linda apply his face, when he looked in the mirror, he hardly recognized himself. He never knew he could look so good. Better than pretty, he looked beautiful.

For sure, he looked more female than male and in the dim lighting of the party, a few men on the way from his room to the function, already mistook him for a woman. He couldn't believe it. He was pleasantly surprised, when he was one of the best dressed and most authentically looking women there.

Instead of sitting alone, he was invited to sit and mingle with others. Some were just like him, first time attendees, then, there were others who had been attending functions like these for years. He was surprised that they had cross dressing socials in nearly every city in the country and all over the world. There was a secret underground of cross dressers that he knew nothing about. How would he know? Hiding and keeping his secret to himself, he never imagined there were so many men like him.

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bySuperHeroRalph© 8 comments/ 49135 views/ 8 favorites

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