This is an entry in the Literotica Halloween Contest. I hope you enjoy it and vote and leave a comment accordingly.
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Every year, Pauletta really looks forward to the end of October. As in many cities with a substantial population of gay, lesbian bisexual and transgendered persons, Halloween is a special occasion, more so than any other day of the year. In San Francisco, this has been the case since the 1970's. To Pauletta, this is ancient history, although he has read and heard about the city's futile efforts to suppress the gay lifestyle, which finally ended during that decade. Accepting the inevitable and recognizing the political clout of GLBT persons, the city now blocks off streets in order to allow the gay community in the Castro District to put on an annual party every Halloween.
Pauletta, like other celebrants, enjoys the partying in the street and in clubs, but what he likes most of all is the drag queen beauty pageant. On his first Halloween in San Francisco, he marveled at the charm and grace and beauty and the way the contestants exuded sexuality, and his viewing of the contest was the one event most responsible for his deciding to become one of those lovely creatures too. At the time of the second Halloween of his residence in San Francisco, he was an entrant, but did not do well. He and his friends have always attributed his rather poor showing to several factors.
For one thing, when he arrived in town, his blonde hair was worn in a crew cut, which had been a form of protective coloration in his home town in America's Bible Belt. For no good reason, his blondeness, his short, slender physique and his fair skin had made some of his contemporaries suspect him of having gay tendencies. Long hair would have further aroused their suspicions. Being gay in that place, except that "queer" or "faggot" or "fairy" would have been the descriptions used by gay bashers, would have been considered grounds for vicious beatings and extreme ostracism.
Paul Porter, as he was then known, kept his true nature concealed in hopes of avoiding such a fate. He let his hair grow out immediately after arriving in San Francisco but, at the time of his first participation in the contest, it was not yet long enough to fall in feminine waves down his back, and this was regarded by the judges to be a negative quality.
For another thing, he was still getting accustomed to high heels. Until donning feminine garb, he had always worn sneakers, and he was still not used to the new footwear. As a result, he had been awkward during the promenade before the judges, which was an important part of the contest, instead of graceful as the other entrants had been. Even more important than either of those reasons was the political nature of the event. The judges were all owners and managers of gay bars, and they tended to vote for their own patrons. Pauletta had not become a regular at The Purple Knight back then, so he had nobody to vote for him on that basis.
During his second year as a drag queen, his hair was shiny and long enough to cover his shoulder blades, and he had mastered the wearing of the high-heeled pumps that went with the clothing he chose to wear. While competing the previous year, he had felt self-conscious and ill at ease sashaying in a miniskirt in front of a crowd, even of persons who appreciated his beauty and were cheering for him. That was no longer the case when he entered the second time. In addition, he had become a frequent patron of The Purple Knight, and knew the owner and all the regular bartenders. He didn't win that year either, but he was a strong contender and deserved his second place finish at that pageant and the one the following year.
This year, he expected to win the first prize, which had no intrinsic value but did carry a lot of prestige among his peers. His main competition, and the first place winner the two previous years, was a Black woman who was not aging gracefully and had put on quite a bit of weight. There were others who were regarded as contenders, but Pauletta believed he would have been considered the betting favorite, if there had been any betting on the contest.
He took two personal days, on Halloween and the next day, a Tuesday. Wanting to be as close to perfect as possible, he had his hair professionally done and his legs waxed. At the parlor where he had those procedures, he was a regular and a favorite, and everybody there knew he was to be a contestant in the beauty pageant that night. Knowing his efforts would be on display to a large number of potential customers, the owner of the establishment did the work himself, and wished Pauletta good luck after he was finished with what he regarded as the best job he had ever done.
"Good luck, Pauletta. You're going to win tonight," was the sendoff the perfectly coifed blonde got from the owner and employees and most of the customers.
He thanked that group of well-wishers and left, to stop in and greet his closest friends and supporters who were in The Purple Knight. Pauletta was never a heavy drinker, and he ordered his usual, a small glass of white wine, and only drank half of it. After receiving the good wishes of the bartender and patrons, he went home to wait for Cliff in the apartment they shared in the converted Victorian home. He greeted his lover with a warm hug and a long kiss, not concerned with his makeup, because he would do what repairs were necessary just before they left for the celebration.
When it was almost time to leave, he put on the new blue micro-mini skirt he had bought for the occasion. It fit snugly and just covered his curvy ass, and he wore a sheer light blue blouse with it. Those garments perfectly set off his hair and pretty blue eyes. His panties were dark blue and crotchless, like he always wore, and the ruffles on the edges of the slit would be visible to anybody below the stage where the actual judging was to be held. Clearly visible through the blouse was Pauletta's matching padded bra, also with ruffles, and he had decided to buy one a size larger than he usually wore. Larger breasts, he had decided, would make him sexier, even though everybody knew they weren't real. Light blue leather pumps completed his ensemble, and both he and Cliff believed he cut an even sexier figure than usual.
The contest itself would be held in the gymnasium in Eureka Valley Recreation Center, a block away from Castro Street. Many of the contestants, including Pauletta, would be scantily clad, and the late October night in San Francisco would be too cold and maybe foggy for them to look their best while outside. On their way there, he wore a long wool coat, which Cliff would hold onto during the judging. When they entered and made their way backstage, the audience greeted them with enthusiasm, for they all knew he would be one of the leading contenders for the title this year.
Belle Black, the winner in the pageants for the last two years was greeted with almost the same level of enthusiasm. Although competitors, he and Pauletta were on friendly terms, unlike some of the other entrants, and their kisses of greeting were full on the lips. Belle was a large African American, and he wore his long black hair in cornrows, and his smiling face was meticulously made up, but the rouge and mascara and eye shadow and lip gloss couldn't cover the signs of aging.
Each drag queen in the pageant wore the attire he thought would make him the most alluring, and Belle had chosen a long black jersey gown that hugged his voluptuous figure. Both sides were slit to the waist to show off his shapely legs in red fishnet stockings and red panties and matching garter belt, and he wore red shoes with two inch heels.
"You look beautiful, Pauletta," Belle enthused. "This will be your year to win."
