A gay sex stories: Pauletta's Halloween Pageant 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.”
“Thank you, Belle. You’re gorgeous yourself, and if I don’t win, I hope you do.”
“It’s nice of you to say that, but I think I’m over the hill.”
“Not yet. Not for a long time yet.”
Their exchange of compliments was interrupted when they were called on to take their place in a line on one end of the stage. Those places in line had been chosen by drawing names from a hat, and Pauletta would be the second to undergo the close and intimate inspection which would result in the winner being chosen for the year. The audience would cheer their favorites and whistle at all the beautiful contestants, but the judges would be free to ignore those demonstrations of affection and lust.
The first contestant was named Sweet Sue, and he was wearing a slinky black cocktail dress and had red hair, worn in a tall bouffant style. He strutted forward on his stilettos, carrying a silver handbag, and earning a cascade of cheers and other loud demonstrations of admiration. Pauletta and Belle and the others watched while Sue was subjected to a personal examination that, under other circumstances, probably would have evoked cries of outrage from him. Pauletta was glad to see one of the judges was Jack, the manager and night bartender from The Purple Knight, who had always been friendly toward Pauletta and did not try to hide a strong element of lust in his feelings.
When Pauletta was called forward, he sauntered up to the judges, flirting with all of them, something else he had learned to do since his first attempt to win the title of Most Beautiful Drag Queen. The crowd expressed their appreciation even more loudly than they had for Sweet Sue, but the judges were, for the most part, unswayed by their expressed opinion. Jack quickly stepped forward to be the first to use his hands in the inspection process.
“You’re looking really hot tonight,” the bartender/judge greeted him.
“Thanks Jack. You look really handsome too,” Pauletta replied, batting his long eyelashes. “Oooo, you’re a fresh guy. I like fresh guys.”
That last sentence resulted when Jack slipped his hand under Pauletta’s skirt and fondled his cute ass. He had heard the same comment at least a hundred times when Pauletta had said it to men in The Purple Knight in response to a similar liberty being taken, but he always smiled at it. He liked it even better when it was directed to him. Emboldened, he slid his hand through the slit in the sexy blonde’s panties and stroked the cleft between the soft hemispheres. Pauletta smiled flirtatiously, enjoying the attentions of his friend, and tossed his soft blonde hair.
There were no actual rules for the judges, but some decorum was expected. Jack’s fondling of a contestant’s bare ass probably would have exceeded the unwritten rules, but Pauletta was facing the crowd, and nobody could see just what was going on. When he turned and bent slightly over to let the onlookers get a better look at his panties, Jack removed his hand and started stroking the shapely legs before him. They were silky smooth, and the judge murmured his approval, making Pauletta glad he had spent the extra money for waxing, rather than shaving them himself. When Jack finished his extremely intimate examination, the other judges performed much the same kind of inspection, although nobody else got quite as personal.
When they had all finished, the admiring bartender from The Purple Knight patted his favorite’s ass a final time and kissed him on the cheek. “You look like a winner,” he whispered into the delicate ear by his lips.
Pauletta felt like a winner, and he thanked Jack and strolled over to the other end of the stage to join Sweet Sue. The two were rivals, but not friendly ones, and they ignored each other, as both watched the judging and fondling of the other entrants. As the winner the previous year, Belle Black was the last to be evaluated, and he and Pauletta stood holding hands as the scores were tallied.
The member of the City’s Board of Supervisors representing District 8, which included The Castro, stepped up to the microphone to announce the winner of the beauty contest. He had not been one of the judges, and he was there only to announce the decision of the judges and to present the silver plated tiara.
“Ladies and gentlemen,” he announced. “I am proud to announce the winner of tonight’s pageant, the most beautiful drag queen in The City and County of San Francisco and probably in the world, is Pauletta Porter.”
The crowd and some of the other contestants applauded. The runners-up who applauded also congratulated the winner with their hugs and kisses but some others, including Sweet Sue, remained aloof as Pauletta approached the elected official. He continued with his presentation as the tiara was brought forth from the decorated box where it had been placed earlier, so he could hold it in his hands. He continued:
“Here to present the silver tiara, emblematic of winning this beauty pageant, is the winner from the last two years, the beauteous Belle Black.”
The previous winner approached the man holding the prize. Belle took the tiara from his hands and Pauletta bent down slightly so it could be placed securely amid his long blonde tresses. He straightened up after that, and he and Belle shared an embrace and a long kiss on the lips, and that was the finale of the pageant, except for more applause and other expressions of admiration.
There were still many revelers on the street, drinking and kissing and fondling each other, but the pageant winner and his man wanted to spend some time with their closest friends, whom they knew would be gathering at The Purple Knight. Cliff helped Pauletta with his long wool coat, although expressing some regret at concealing such a gorgeous body, and they went out through the front door of the center.
Hundreds of persons on the street paused in their carousing and called out their congratulations on the way to Castro Street and, once they entered The Purple Knight, the friendly shouts became a cacophony. Word of Pauletta’s victory preceded them, and a host of his friends, including Jack, were waiting there for him. The drinks were on the house for the lovely young drag queen, and for his escort too. He had never been a heavy drinker, and Pauletta always limited himself to no more than three small glasses of wine in one evening, but he exceeded that limit his night, and was actually a bit tipsy by the time he and Cliff left the club and headed for their apartment.
They were exhilarated by the night’s events, and were both anxious to get home and make love. The Castro is a relatively small area, and most places are close enough to walk to, so they hadn’t bothered to use Cliff’s car. Pauletta unlocked the door and locked it again after they were safely inside their warm, pleasant dwelling. All night long, they had wanted to demonstrate their feelings for each other, and to do it in private. They made the most of the opportunity, sharing a warm embrace and an even warmer kiss, pressing their lips together and letting their tongues roam freely.
“Get the bed ready, Sweetie,” Pauletta said after they separated their mouths. “I’ll get myself ready for bed.”
Cliff knew that would take quite a while, because he knew that meant carefully removing his makeup and brushing his long blonde hair. There would never be any complaint about the time taken, because Cliff was proud of the beauty of his mate, which had been officially certified that night, and he knew a lot of time and effort was involved. He considered the wait to be worth the result, and prepared the bed as he had been asked to do. This meant folding back the top sheet and other bedding, so just the fitted bottom sheet and the pillows would be in place to be used. Most important, it also meant spreading a towel under where Pauletta would be kneeling, so they wouldn’t have to sleep in the semen that would be ejaculated when he climaxed.
Cliff prepared himself too, removing his jacket and shirt and socks – they had both removed their shoes when entering the apartment — and sat on the bed to wait. Many minutes later, Pauletta exited the bathroom, wearing his panties and bra. He was carrying his other clothing, along with the bottle of Aqualube which was usually kept in the bathroom, and a damp towel. He left the bottle and towel on the bed and, after hanging up his skirt and blouse, sidled up to Cliff, who was eagerly awaiting him.
“Hiya, Handsome,” he said in his most seductive voice. “Did I make you wait too long?”
“No, it was worth the wait.”
“Well, we’ll have to make sure of that, won’t we?”
Pauletta knelt on the floor in front of the horny man who had been waiting for him and grinned. Cliff had left his pants on because he knows his lover likes to remove them as part of their sex play, and he smiled when Pauletta reached up and unfastened his belt and the buttons at the waist of his jeans. He leaned back to allow his fly to be unzipped and lifted his ass off the bed when Pauletta started pulling his pants down and all the way off around his feet, to be tossed aside. That left him wearing only jockey shorts, and his stiff cock was sticking straight up in the air through the fly.
After briefly fondling the erection, Pauletta pulled off Cliff’s shorts, dropped them on top of the jeans, and leaned forward, his elbows resting on the thighs of his partner and his fingers delicately holding the hard shaft. Even before he and Cliff started living together, this had been one of his favorite cocks, long and hard and thick. He leaned forward so his tongue and lips could give a long, slow caress, from the scrotum to the head, and the rigid shaft felt even better to his mouth than it had in his fingers.
Pauletta rose up and started licking the head, reveling in the velvety texture. His tongue stroked in concentric circles until he was licking under the ridge, at which time, he bent his neck down and took the shaft all the way to the back of his throat. His lips stayed in that position, while his tongue laved the shaft inside his mouth, loving the smooth skin stretched over the hard roundness.
Sometimes he sucked Cliff off but, on that night, he wanted that big cock all the way in his ass. He stroked a few more times with his lips, then stopped and held the shaft in his fingers again.
“I want this big dude in my ass tonight,” he informed the man who would be putting it there.
“Then that’s where you shall get it.”
Cliff went to the dresser, opened the drawer where the condoms were, selected one and rolled it onto his cock. He picked up the bottle of Aqualube and the damp towel when he returned to the bed, where Pauletta was lying face down with a pillow under his hips, presenting his ass to the man who would soon be fucking him there. To Cliff, it was a truly beautiful sight, the lovely, pure white mounds, which Pauletta reached back to spread, and the cute pink rosebud between them. He leaned over and planted a wet kiss on either of the succulent twins before reaching between them and using the thumb and forefinger of his left hand to spread the soft sides of that rosebud. Holding the open bottle of lubricant in his right hand, he pressed the neck against the small hole being created and squeezed the plastic sides.
Pauletta murmured happily when he felt the cool, oily liquid gush into his ass, and started squirming in anticipation. The next delight was when Cliff’s finger eased in all the way to the knuckles and spread the Aqualube evenly around the inside of the place that was so eager to be filled by his cock. His prostate gland, which he always called his clit, was being massaged, but he knew his partner’s cock would do a much better job of that. After that part of their love-making, the digit was withdrawn, and the sexy drag queen eagerly anticipated what would happen next.
He didn’t have to wait long, because Cliff was every bit as avid for the carnal pleasures they would be sharing. Holding Pauletta’s love hole open with the same thumb and finger, he guided his cock with the other hand until the tip was pressed against the oily hole and moved it up and down to spread the lubricant and make the first penetration. When everything was ready, he thrust forward and both men sighed happily when the big cock head wedged into the place where it was wanted so much.
Cliff remained in that position, while waves of pleasure swept through him and Pauletta. When he finally thrust forward again, they moaned in bliss as an inch more of his cock burrowed into the horny young blonde on the bottom. The man on top ran his finger all around his lover’s ass to make sure there was no loose skin or other potential problem and, finding none, drove his cock in still more deeply. It was in far enough he no longer needed to guide it, so he let go of his shaft and used the towel to wipe all the excess lubricant and anything else from his hands.
He was ready for some serious fucking, so he placed his hands on Pauletta’s hips and pulled back on them while plunging his cock in farther. Most of the rest of its length surged into the ass below him, and the blonde hotsy moaned in pleasure. Cliff’s sounds of joy formed a happy duet with those of the other man.
Pauletta’s body was writhing blissfully from the hard, thick cylinder that was being imbedded in his ass, especially the way it was massaging his clit. He turned his head back toward Cliff and begged for more. “I love your big, hard cock, Sweetie. Give me all of it.”
“I’m glad, because I love your cute little ass. You’re gonna get everything I’ve got for you.”
He was as good as his word and, after two more strong thrusts, Cliff’s entire cock was buried in Pauletta’s ass, so deep he could feel pubic hair brushing against the soft insides of his cheeks. For harder and deeper stroking, he moved his hands to his partner’s shoulders, and they lay like that for a minute or so, letting the exquisite pleasure throb through their bodies. Finally, Cliff slowly drew back and paused for a few seconds with just the head of his cock inside the ring of muscles at the entrance to Pauletta’s ass. While the supine man writhed in anticipation, he paused for a few seconds, before driving the entire length back in until his pubic hair was once again tickling the damask insides of the succulent cheeks.
The next stroke was much like the first one, and so were the dozens more that followed. Pauletta was thrashing on the bed and sobbing with the pleasure that was radiating from his ass and clit, but he knew a way to make their coupling even better. “Let me get up on my knees, so I can fuck back to meet you.”
That seemed like a good idea to Cliff so, with his cock buried in Pauletta’s ass, he got to his knees and helped his lover do the same. When they were in the desired position, they were both kneeling on the bed with Cliff behind and his hands resting on the soft hips in front of him. With everything in readiness, he drew his cock back, paused and thrust forward again. When Pauletta felt the hard cylinder surging into his ass, he fucked back to meet it, and the men’s bodies came firmly together with a soft slapping noise and a pair of happy sighs.
They continued like that, with Cliff plunging his cock into Pauletta, who fucked back to meet every stroke, while his movements became more erratic. The top man of the couple knew what that meant — that his partner was getting closer to an orgasm, and he leaned to his right to look around the drag queen’s body. He saw how he was starting to reach for his own cock, so he could masturbate, but Cliff pushed the hand away and gently held the rigid shaft in his own. He knew Pauletta liked to be on his knees for two reasons — to fuck back as he was doing and to stroke his cock to a climax or have his partner take care of it.
Like most men, Cliff believed the best fucking happened when all participants were able to enjoy it to the maximum, and that always applied to Pauletta. He started stroking the hard cock in time with his thrusts into the delightful ass in front of him. With pleasure coming from two sources, his partner’s movements became more erratic, and Cliff had to hold onto one hip to make sure they didn’t fall over. He was holding back his own climax, because he believed nice guys finished last, but he hoped Pauletta didn’t take too long, because he couldn’t delay for much longer.
Fortunately, he didn’t have to. “Oh, Cliffy! fuck me harder! Fuck me faster!” his partner warbled. “I’m ready to cum!”
As requested, he started driving his cock harder into Pauletta’s luscious ass, while stroking the young blonde’s cock at the same pace. Both men were whimpering from the exquisite pleasure they were giving each other, until the man in front sang out ecstatically that he was cumming. Cliff felt his partner’s cock jerk, and he felt warm semen gush out onto his hand, but he continued fucking and stroking until two more bursts of cum were sprayed onto the towel covering the middle of the bed. Pauletta sprawled forward, and Cliff continued driving his cock into the delightful ass until he climaxed too, and he ejaculated three times also, but his semen ended up in his condom.
After resting for a few minutes and catching his breath, Pauletta was almost ready for some sleep. There was still some preparation of the bed and himself needed, so he rolled up the towel and dropped it into the laundry hamper in the bathroom. While Cliff prepared their bed by pulling the coverings back into place, Pauletta washed his cum from his belly and put on his negligee. Even when he was sleeping, he liked the sensation of being in drag.
Being fucked long and hard by Cliff and being helped to a great climax by his partner’s hand before curling up to sleep beside him was a fitting end to what had been one of the best days in Pauletta’s life. He smiled to himself at all the good things that were going for him. There was the love, or at least the affection of the good man who lay beside him, the admiration of his many friends, the respect he knew he enjoyed at work and the envy of some of the drag queens who had been adjudged less attractive than he. The latter was attested to by the tiara that sat proudly on the shelf, announcing to the world how he had been named the most beautiful drag queen in a city which was well-known for its beautiful men and women.
He looked over at the shelf. It was dark in the apartment, but some light from a streetlight shone through the window, and this light was reflected off its shiny silver plating, so he knew it was there, and that was good enough. Life was, indeed, good for Pauletta Porter from the obscure and conservative small town in The Bible Belt.
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Thank you for reading this story by me, Boxlicker101. Here is an URL to many more of my stories: http://www.literotica.com/stories/memberpage.php?uid=207952&page=submissions
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