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That First Halloween

"Guy ventures out on Halloween dressed at Princess Jasmine."

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Guy just sat there in his car wrestling with the decision to get out. Every time he reached for the door handle it caused his heart to beat harder in his chest so he stopped. He would occasionally check his make up in the mirror expecting that something changed since he last checked it.There was no change, he was still as stunning as ever.

He finally worked up enough courage to exit his vehicle and stand next to it. He watched as other party goers arrived and entered the club across the street. This club was not one of his preferred watering holes, it catered to those who embraced a different lifestyle and their Halloween parties were rumored to be the best in the city.

Every person he saw was in costume and make up and he felt a little better, but he was still afraid. His fear was well based. Guy was a cross dresser and this would be his first time out in public dressed as a female. It was a coming out party so to speak and he had waited and planned this night for along time.

Like many others he never knew where this desire to dress up had come from and he tried to ignore it at first. Maybe it was the fact that he had grown up with two attractive older sisters and that he was always in close contact with their clothing, especially during his week of doing the laundry.

Maybe he was envious of their soft silky clothing.Their bras, slips and panties were in a variety of styles and colors and just touching them caused a tingling in his balls. He remembered the day when he finally give into his urges and borrowed a pair of clean panties from the laundry basket and hid them in his room.

Later that evening after the household was asleep he removed the boxers he slept in and slid the tiny silken panties up his legs. The feeling of his cock and balls being cradled in this silken cocoon was beyond description, but it wasn't enough.

He recalled silently creeping back downstairs in the dead of night and removing a pair of black pantyhose from the line and hurrying back upstairs. Once in his room he slowly slid them on over the borrowed panties.

The sensation of his legs being encased in the black filmy material had him as hard as a rock. He stood in front of his mirror and ran his hands all over his legs and groin, he could not believe how good his legs and butt looked and felt in the borrowed finery.

That was how it started. Now detection of this habit by his family and friends would spell trouble, so he kept this habit a secret. He survived high school by borrowing his sisters lingerie or nighties and wearing them at night behind closed doors.

His desire to dress and look female changed the course of his life and led him to take cosmetology classes in college. Male hair dressers where the up coming thing and he excelled at makeup and hair design. He passed his state exam and was eventually offered a job at a high end hair salon after graduation.

His long lean frame and good looks made him very popular with his female clients and they brought their friends to see him. His popularity grew and so did his income, he was finally able to move out of his parents house and buy a condo. Now he could indulge in his fetish without fearing discovery. 

Guy soon set up a dozen accounts with on line make up and lingerie companies, his collection swelled with dozens of bras, slips, panties, garter belts, and nylons. At nights he dedicated a few hours practicing his makeup techniques and soon mastered the art of looking female.

He eventually purchased a pair of high heels and after a dozen falls mastered how to walk in them.

Now Guy had never considered venturing outside as a female until tonight, but it was Halloween and he needed to see just how passable he was. His Princess Jasmine costume had been custom made and it fit him like a glove, it drew many whistles from the passing cars as he walked across the street.

The turquoise colored harem pants were almost sheer and showed off the silhouette of his long and slender legs as he moved. The sensation of them rubbing his legs as he walked was indescribably sensual. The top was short exposing his arms and shoulders and it ended under his phony breasts.

With the harem pants hanging on his hips his flat and tanned midsection was exposed. He was glad that he had spent those extra hours doing crunches at the gym. The brief he wore underneath did a great job at hiding his manhood and hugging his butt.

The wig and jewelry were exact copies of those that the Disney character wore and he added a thin veil trimmed with lace worn across his nose and mouth. 

Based on the number of times he was complimented as he waited in the small line he knew that his makeup was perfect. Even the bouncer at the door was so taken with his looks that he was never asked for an ID. His hand was stamped and he was bade to have a good time as he entered the club.

The club was bigger than it looked and jammed with people.

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As he made his way to the bar he received more compliments and kisses of welcome on the cheek. There were even a few gentle caresses of his silk covered bottom from unseen hands as he moved through the throng of costumed party goers.

The bar was jammed so he found an unoccupied table and took a seat, a waitress appeared and took his drink order. Guy was so absorbed with watching the crowd that he did not see the tall dark figure approach his table.

"May I join you, Princess?" a soft voice asked.

When Guy looked up there was the masked bandit known as Zorro. He was well over six feet tall and his costume was a perfect replica from the old TV series.

Guy knew that this was bound to happen. An attractive female sitting alone was sure to attract the attention of some lonely male. Since this one looked safe and still sober Guy invited him to sit.

Though Guy's exterior was calm there was a storm brewing in his head. What was he doing? He wasn't gay so why was he smiling at this man? Why did you invite him to join you? What happens when this handsome stranger finds out he is not a real female?

Guy removed a pack of cigarettes from his tiny silver purse and placed it in his mouth. Zorro produced a small gold lighter from a hidden pocket in his cape and lit it. They chatted about their costumes and discovered that they had both used the same company.

Guy was asked to dance when the music slowed down and he accepted almost against his will. It seemed that the Princess was taking over his personality. Once on the dance floor Zorro gently embraced him and just the touch of his gloved hands turned Guy on.

He didn't press his body too close against his dance partner less the bandit feel his erection struggling against his nylon brief. As they danced Guy decided that he had better take his leave before things go too far.

Once again the female he had become resisted this notion and he allowed himself to be escorted back to their table.

"Have I told you how beautiful you are?" the bandit said sliding his chair closer to him.

"No you haven't. Did I mention how good you look?" Guy responded as Zorro placed an arms across Guy's shoulders.

"Leave now," his inner voice screamed.

"But you have not been totally honest with me," the masked bandit said as he removed one of his leather gloves.

Before Guy could react Zorro's hand moved toward the crotch of his harem pants and circled his cock that was hardening by the second. Zorro then placed a gentle kiss on Guy's cheek through his veil as his hand began to gently manipulate Guy's cock.

"Please stop," Guy said softly.

The bandit ignored his pleading and undid one end of the veil that was covering her nose and mouth and placed a gentle kiss on the now exposed red lips. Between the kissing and the non-stop movement of the bandit's hand Guy had become hard, harder than he had been in years.

"Please, what if someone sees?" Guy pleaded.

"No one is looking, now kiss me," Zorro said.

A force from within Guy moved his lips toward Zorro's. He started to gently kiss his lips and then inserted his tongue in his mouth, the bandit did the same. As they sucked each others tongues Guy's hand drifted to Zorro's crotch and began to manipulated the lump he found there.

"You have to stop. If I cum everyone will see the stain," Guy pleaded again.

"Well we can't have that," Zorro replied as he released Guy's swollen cock.

He stood up and took Guy's hand. Once again the Princess made Guy stand up and be led outside to the parking lot. They stopped by the side of a full size SUV.

"I want to fuck you so bad," Zorro stated.

Panic gripped Guy's brain, he never planned on this. He decided he would be compliant then deliver a blow to Zorro's balls when the opportunity presented itself and run like hell.

"You must not be so fearful, Princess. Things aren't always as they appear," Zorro said with a smile.

He kissed Guy a few more time before he stepped back and unbuttoned his silken shirt. He then grabbed one of Guys wrists and kissed his hand before pushing it through the opening of his shirt.

Once inside Guy's hand found a pair of breasts with swollen nipples that were almost flattened under a skin tight t-shirt. The Princess embraced Zorro again and allowed his hand to move under his cape as their lips met.

His hands felt a tight butt under the spandex pants and his fingers detected the outline of a thong underneath them. They sucked each other tongues as they ground themselves against each other.

"I still want to fuck you, Princess," the man in black admitted.

"Here in your car?"

"Of course not, that would ruin the illusion. I live in the Carrington Towers condos."

"I'm just down the street at the Carriage Hills," Guy replied.

Published 
Written by ThePhantom
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