Cindy (Part 1)

by Cassandra Di Bonet

Sidney lived with his gay twin older step brothers in their plush uptown apartment. He was just 18 when his brothers took him under their roof. The problem was that his brothers were both gay crossdressers and treated poor Sydney like a slave. Whenever they dressed up to go out, Sydney had to paint their long fingernails, help them zip up their dresses and other tasks. He was not allowed to go out but had to stay at home and clean the apartment, wash the dishes, wash and iron their sexy dresses and lingerie, and clean their high heeled shoes till he could see his face in the patent leather. Most nights his twin brothers would bring home hot looking trannies, which they would take to their rooms and fuck til morning. Little did they know that when they were out, Sydney would prance around the apartment in their oversized 4 inch spike heels masturbating his hard cock, and wishing he could go out dressed to kill.

Now Roy and Raymond (those were their names) weren't exactly the most glamorous crossdressers on the planet, but they were passable because of their slim builds and long legs. They both took size 14 in high heels and that along with being almost 6 feet tall without heels made them wear nothing higher than a 4 inch stiletto. Sydney on the other hand was quite attractive for a boy and was no stranger to kissing sissy boys and giving them blowjobs. On one night in paticular the twins were invited to a crossdressing party at the gay disco called Cloud 9. Poor Sydney helped his brothers get dressed for the occasion and wished he could go with but knew he had to stay behind to wash the dishes and the three loads of washing and ironing that they left for him.

He watched their car dissappear down the driveway when a voice behind him made him jump: "Would you like to go to this party too?" Sydney turned around to see a slim effeminate young man of about thirty in killer stiletto boots and a Pvc catsuit standing in the living room. He noticed the mystery visitor had long red sexy fingernails too. Even with the heavy make-up the man was wearing, Sydney recognised his godfather, Uncle Jack. Now Sydney knew about his gay Uncle Jack, but didn't know he had such a hot fetish like this. It made his cock rock hard.

"What are you doing here and how did you get in the apartment?" Sydney asked, smiling.

" Oh I discovered I had some special talents, hon. I'm your fairy godfather although it's just a part time job.....I'm a qualified domatrix who femminizes sexy sissy boys. I'm here to grant you a wish........what will it be?" Uncle Jack said.

"I want to go to this party........but I don't have a thing to wear," Sydney said, looking dissapointed.

"No problem!" Uncle Jack said as he waved his effeminate hand over Sydney. In a couple of seconds Sydney noticed his own hands began to change as his fingernails became longer. He gulped when they stopped at two inches and noticed they were painted a bright red......his favourite color nail polish. His chest seemed to swell as he suddenly grew huge D-cup boobs, his clothing seemed to change too. In no time he was wearing a tight purple top which made his boobs look bigger and a short sexy PVC miniskirt which showed off lots of leg and thigh. His legs were soon covered in black lacy thigh high stockings and suddenly Sydney found himself balancing on his toes. He looked down and saw the sexiest pumps on his feet. They had very pointy toes and a towering 7 inch heel. He was hornier than he had ever been before.

"You better go to the bathroom and take care of that," said Uncle Jack, looking at the huge bulge in Sidney's lacy panties. Sydney amazed himself at how easily he managed the sexy killer stilettos as he sashayed to the bathroom, swinging his hips sexily. When he got there he took out his rock hard cock and stroked it purposefully, admiring his new long nails wrapped around his shaft, until he shot a huge load of sissy cum into the toilet bowl. He wiped his throbbing cock clean and licked the cum off his hands. He tucked his half hard cock back into his panties, he glanced in the mirror and popped another boner when he saw his heavily made up face. He looked like a high class slut. He sashayed back to Uncle Jack in the living room, wondering what else was going to happen.

"Oooh! Uncle Jack these high heels are sooo sexy and sooo high!" Sidney giggled.

"Yes, they are!!" Uncle Jack remarked. "But you have a party to get to.........let's go downstairs and see what mode of transport we can come up with."

They both click-clacked noisily down to the garage, but all they could find was an old mountain bicycle. "Mmm..... this will have to do." Uncle Jack said waving a feminine hand over the bike. A cloud of pink smoke enveloped it and as the visibility got clearer, Sidney saw a stretch limosine like the Hollywood filmstars rode around in. "Wow!!" Sidney gasped, "But I can't drive."

"No problem!!" Uncle Jack replied and waved his hand and a very cute sissy boy with long sexy nails stood by the driver's door. He was wearing ultra short PVC hotpants and thigh high stiletto boots with incredibly pointed toes and towering seven inch heels. And his cotch bulged obscenely.

"Now go along......have some sexy fun........but remember Cindy, you must be home by the time the clock has finished beeping midnight!" Uncle Jack said seriously.

"Can I first........?" Cindy asked, as he couldn't keep his eyes off his chauffeur's bulging crotch. The sissy boy driver was eying out Cindy lustfully too.

"Oh you wicked sissy boy," laughed Uncle Jack. "Of course you can........you better make it a quickie in the back of the limo. Time is running out!"

The two sissys climbed into the limo, and in no time were both their panties down around their knees. They both kissed each other hungrily and then sucked each other's hard cocks til they orgasmed.

"You're one hot horny sissy, hon!" the sissy driver said. "Where have you been hiding?"

"You're a hot sissy boy too.....and you're sooo big!" Cindy giggled as he frondled his sissy chauffeur's enormous nine inch cock. "Maybe we can get together again after tonight?"

"Maybe.......I work for your Uncle Jack. I fuck him every night in return for high heels and lingerie. I help him out with other sissy boys by driving them to functions. A sort of sissy boy escort. We better get going, hon. We have a party to attend."

He kissed Cindy passionately and climbed into the driver's seat, his cock still rock hard. As he drove to their destination, he masturbated. He kept looking in the rearview mirror at Cindy in the back who was busy stroking himself, his eyes glued to the huge hard juicy cock of his chauffeur.

It was going to be one hot, horny night that Cindy would remember for a long time. He sighed as he watched the sissy driver's huge cock orgasm and in no time he was spurting his sissycum all over the backseat.