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Founded Sep 10, 2012
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This sissy is hiding under a macho disquise
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smooth sissy lover
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Sissy Bill"s Fantastical Reunion

by Debra Darling

Sissy Bill had made a very serious mistake. Just how serious he would soon find out. He had told Mistress Lydia to whom he was a sissy maid in training that he was going to be out of town for the coming weekend. He was planning on attending his high school reunion.

The big dance on Saturday night was a theme party with costumes encouraged. Mistress had acted all excited for him and asked how he would be dressed. He told her he was going as the prom queen he had always wanted to be. Then, on Sunday for a brunch with some of his teachers, he would just be himself. Mistress Lydia was in charge of his sissyfication program and she suggested he be a sissy maid on Sunday. He could serve his ex-teachers just as they had served him as a student. Sissy Bill demurred. He was not ready to come out quite that far. Sisssy Bill did seem to notice the frown that briefly crossed Mistress Lydia's face.

Mistress then suggested he stop by her studio on Saturday before he went to the dance. She offered to have her staff of experts do his makeup professionally and even give him a free manicure and pedicure so he would look like a perfect princess. She said he should allow them several hours to really do the job right. She even agreed to lend him the use of her private limo with a driver so he would arrive at the party in style. He did so, and that was when things began to spin out of control. In turned out Mistress Lydia had some plans she had not shared with her Sissy Maid.

He had arrived at the studio wearing a gorgeous pink cocktail dress. It had a modest bust line, a flowing skirt and a built in crinoline. The Spanish style top was of shiny pink satin and was cut to display a modest decolletege. A ruffle held the sleeves just off his shoulders, displaying his hairless chest and a delicate rhinesonte necklace. The skirt was net over satin and held out from his waist with built in light petticoats. It was clearly a prom gown and he was so proud to have found it. He had even had it tailored to flatter his figure as much as possible.

Under the gown he wore a white satin briday bustier that drew in his waist and held the modest sized silicon breast forms he wore. Below that, satin panties and a panty gridle that was padded with form. Combned the garments gave him a fairly nice curvey figure. Matching shoes with three inch heels and a rounded toe set off his nylon covered legs. His pantyhose were nude in color. A long blonde wig topped his head and tasteful makeup completed the look. He did look like a prom queen, even to the tiara which crowned his head.

"How pretty," Mistress Lydia exclaimed. "Just have a seat over here and we will finish you off. Here is a cup of coffee to drink while we go to work on you." Sissy Bill asked if he could have his nails done in pink to match the dress and if they could be kept fairly short. He drank the coffee and was enjoying the manicure when he drifted off. At the last second, he realized he had been drugged.

At one point he seemed to almost wake up. He was aware he was on his back and he was cold. He heard someone ask about a new surgical glue and felt something being sprayed on his chest. Then he flet a prick in his arm and he was out again.

When he finally woke he realized immediatly that things had changed. He had been in Mistress Lydia's feminization program for nearly a year now and he could recognize some of the "accessories" associated with his maid attire even without opening his eyes. Other things seemed strange though. His waist was so constricted he could barely breath so he knew he was wearing the hourglass corset and it was cinched tight. He was soon to learn that this one was made of red and black satin covered rubber and had super strong steel stays. Bending at the waist was going to be almost impossible. His arms had that familiar numb feeling that told him his elbows were cinched together and he could feel the fingerless satin, elbow length gloves he frequently had to wear.

Ferafully he opened his eyes to see what else had happened to him. His pink gown was gone, replaced by a Barbie pink satin dress. It had a low cut top that revealed a spectacular cleavage. The skirt had a white ruffle around the hem and that hem flared out and ended just a smidgeon below his crotch. Miles of white petticoats were visible under the brief skirt. His hose had been replaced with pink stockings held up by garters attached to his corset. With all the pink and white, the black garters lay starkly visible on his bare skin. Each garter was highlighted by a bright pink ribbon. On his feet were pink sandles with seven inch high spike heels adorned with rhinestones. These were T-strap styled and he knew he could not kick them off with the straps fastened as they were. Also, tiny, shimmery padlocks held the straps closed. He would be perched up on the very balls of his feet all evening and the glittering rhinestones would make sure everyone knew it.

His hair had been redone in a blonde mass that looked like the style Farah Fawcet had worn in Charlie's Angles. His makeup was now garish, with blue and purple eye shadow, long fase eye lashes coated in black mascara, three shades of rouge and bright cherry red lipstick.

Someone pulled up his skirts to show him his underwear. White sissy panties with ruffles over his ass. His male equipment was wrapped up tightly in a wide pink ribbon. Not exactly a chastity device but in many ways much worse. His testicles were stretched as far as possible from his body and hung like two ripe plums between his legs. His penus was kept engorged by the trapped blood held in place by the ribbon wrappings. The tight satin ribbon covered every inch except for the very tip. The whole chastity belt like affair was covered by a hugh pink satin bow which helped to keep most of his private parts hidden at least most of the time.

The panties were crotchless and if he was not careful how he moved, everything would show. Someone also explained that his breastforms had been glued on with surgical glue and his wig had been laced into his own hair. He stared at his reflection in a mirror. He looked like a sissy maid. His helpless hands waved about near his waist and he saw the bright red nails that matched his lipstick and his toenails. The nails must have been three inches long.

Cathedral style rhinestone earrings hung from his ear lobes. They were huge and so long they brushed his bare shoulders. A rhiinesonte necklace covered his bare chest, dropping down to a point that lead hte eye to his cleavage. He stared at his reflection for a while before he figured out what the intircate necklace design included. Among the clear, glittering splendor were stones in his school colors, green and white that spelled out the words "sissy" and "maid." In a moment of horror, he realized the necklace also paointeed down to a plascit card nesteled deep in his cleavage. It was his reuniion registration card whichh bore his name and high school picture. Now everyone would know who he was as well as the fact that he was a sissy maid.

Mistress Lydia clipped a rhinestone studded leash to a ring embedded in the necklace and tugged him to his feet. He obeyed automaticaly after his year of training. Carefully he minced his way out to the car and off to his fate. He was actually so frightened he begged Mistress Lydia not to do this to him. He was so fearful of having his old classmates know of his secret desire to be a Sissy Maid. Mistress Lydia just laughed and told him would pay fearly for that indescretion. Being a Sissy Maid was a priviledge and he should be proud to show he served her.

When they arrived at the Country Club Mistress Lydia had the drivr pull up at the front entrance. Her fancy car drew the attention of the crown. He was forced to exit the car first, one long sexy leg and then the other as the gathered crowd watched in amazement. When he was standing up at last, he turned and opened hte door for his Mistress. She stepped out and again clipped his leash in place. To great laughter, he tiptoed carefully after her into the building and the ballroom.

Once inside, Mistress Lydia inflicted the next indignity upon him. She pinned a corsage to his dress, just above one breast. Ribbons hung down and a card was pinned to them. In small print that anyone would have to lean close to his chest to read the ribbons said he would donate $10.00 to the class support fund for every dance he danced as someone's partner. Kisses would result in a $25.00 donation. Other services would be negotiable with his Mistress.

He stood by Mistress Lydia's side during the cocktail hour while she told embarrrassing stories about him to anyone who asked. She also made him curtsy to any male who was introduced to him and to hand them a card that read: Forced Feminization and Sissy Training by Mistress Lydia."

He saw many of the men and a few women give money to Mistress Lydia who then put their names on a card. Then he stood by her seat at dinner helping serve her. Occasionally she would run her hand up his leg and even rub his panty covered bottom. Once she let the guy sitting next to her to do the same. Sissy Bill was totally shamed by this, especially when Mistress Lydia told him to "shake his ass nicely for the gentleman" loudly enough for all at the table to hear. He even had to thank the gentleman for the "honor and pleasure." By the time the band started to play, his legs and feet were screaming from all the hours of standing in those impossible heels.

As the first man presented himself, Mistress Lydia showed Sissy Bill 'her" dance card. Every dance had a man's name penciled in. She would be on her feet and in some guy's arms for the rest of the night.

As it turned out, Sissy Bill not only danced all night he also got a kiss from nearly every partner. Most of them were long, passionate affairs with lots of tongue swapping. For a totally straight male, this was pure torture and something new for him. Mistress Lydia was forcing him to learn new ways a sissy maid was expected to perform. Ways he had not even imagined before this.

During the first band break, she handed his leash to a man she had been talking to. Sissy Bill had seen money change hands and he could only imagine what they had been discussing. He soon realized exactly what she done when Mistress Lydia told him to do what the mean ordered and to see that he got his money's worth. She had sold him.

He followed as the man lead him away although he balked at first when they started into the men's room. His worst fears were realized when the man jerked on the leash and told him Mistress Lydia claimed sissy maids gave the best blow jobs and that if he failed to live up to the promise, Mistress Lydia would demonstrate how a Mistress chastised her maid right there in front of everybody.

So that was to be his final indignity of the evening he thought. A blow job in private or a public flogging. Somehow he knew if he failed in any way to perform adequately, Mistress Lytdia would lash him until he screamed and then make him agree to suck the guy's penus anyway. She would probably make him beg for it publicly.

Resigned to his fate, Sissy Bill entered the men's room. He was about to graduate to the role of upstairs maid.

When it was all over, he found that there was yet one more item to make certain this was a reunion he would always remember. Besides the humiliation of having to unzip a guys pant, pull out his engorging cock, kiss it, lick it up and down and then take it in his mouth. Besides the shock of having to suck it as it was drivenin and out of his throat. Even besides the salty taste of semen as the guy exploded inside his mouth and forced him to swallow every drop.

Several more guys then croweded around him and laughed at his cum smeared lips. They held his head steady as one of them used a pari of barbers clippers to shave his head bald. When they were finished, they shoved the now crying sissy maid back out into the dining room where he was instructed to start cleaning up the tables and bussing the dishes into the kitchen. Now he truly looked like a silly sissy slave maid.

When the band returned he found himself dancing again and again kissing his partners and this time truly dreading the next break. As he whirled about floor in his painful shoes he tried not to even think about the next morning. He had seen what Mistress Lydia had packed. The scandalously sexy black satin French Maid's dress with the multi-colored petticoats. The "special" black, patent MaryJane shoes with the eight inch high ballet heels. (He had finally learned to walk in them but he knew after serving eighteen teachers brunch his toes would be bleeding like a ballerina's after practice. Especially with those black fish net hose cutting into his feet. He also thought of the paddles she had packed. In school, his teachers had all expressed a belief in corporal punishment when he was a student. He knew that aftery the time the brunch was over his rear end would be as bright red as his nails and lipstick were now.

His thoughts were wrenched back to the present as the band quit playing to take their second break and he saw Mistress Lydia with another man. He heard her say something about lubricant as he was lead off to the men's room. This time he was held bent over the sink, his panties pulled down while he learned yet another new his "special" maid's duty.

Afterwards, he was again the subject of much attention from the gathered men. His head was held steady while a large ring was inserted in his mouth. His teeth slipped into gooves in the ring and locked it into place, holding his bright red lips open in a big "O" shape. They held him steady while one used his own lipstick to write on his cheeks and forhead. When they finished they let him see himself in the mirror.

His forhead had Sissy written on it in big red letters. On one cheek were the letters "WH" on the other "RE". It took a minute for him to figure out what it all meant and when he did he blushed bright red as he was forced back onto the dance floor.

Once there, he heard the class president saying that Sissy Bill had raised more money than anyone else for the class fund but a little more was still needed. So Sissy Bill was being auctioned off for the rest of the night. He would be available to go home with the highest bidder to clean and provide "other" maid services for the rest of the night until the brunch on Sunday. He held up a scandoully sexy red negilieg, floor length but very revealing. It was two piece as it included a flowing gownwith feather boas as trim. A pair of black stockings and bright red CFM sandals with six inch heels went with the package. Sissy Bill heard Mistress Lydia as she leaned near and whispered in his ear, "I think I'll even throw in a package of Viagra for the lucky bidder. And maybe even your favorite whip."

Yes, this would truly be Sissy Bill's Fantastic reunion. One that he would never forget.

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