Chastity Release

"It isn't fair, mistress," said Paul bitterly. He was seated in front of the large wall mirror in his bedroom and was staring angrily at his reflection.

"Nonsense, sweetie," said Julia, who was styling his long hair. "You know the rules. Every month you wrestle Luke, and the winner earns a release from his chastity device. It looks fair to me."

"He's a head taller than me and must be at least twice as heavy! Besides, his mistress doesn't force him to take oestrogens, right?"

"Don't be sexist, Cecily," said Julia, using his female name. "Weight and muscles aren't everything, you know. You practice yoga and aerobic every day, so you could make it if you really applied. Use his own strength against him."

"Easier said than done," said Paul, sighing in frustration.

If a stranger had come in the room right now, the scene in front of him would have puzzled him. A twenty-year-old boy, quite short and slightly built, dressed in a white silky robe, was waiting patiently as a woman in her thirties straightened his hazelnut brown hair in what was unmistakably a female hairstyle. At a closer look, there was clearly something off with the boy. His legs, chin and body were perfectly waxed, his skin looked smooth and soft, and his nails were long and shaped. He didn't have full feminine curves yet, but there was a hint of a breast on his chest and his hips were larger than usual.

"But please," he said after a while, unable to restrain himself. "Why do I have to take care of his release this time? I've never done it before."

Julia shrugged. "We love to spice things up. Anne and I thought it'd be a funny change. You're both straight, actually, so it'll be interesting. Anyway, I don't think it'll be such a bad experience for you. You need to learn how to please a man."

Paul swallowed hard. He didn't like the implications of her last words. After months of training and punishments, he'd got quite used to go out in female clothes, but he'd never slept with another man before. Clearly, Julia wanted to make a habit out of it. If only he could take off the awful steel cage that was crushing his member and forced him to do whatever she said. It was a perfect little trap.

"Now, honey, it's time to select your lingerie," she said cheerfully once his hairstyle looked flawless. "What do you think of the red set we bought last week?"

Paul's eyes widened with horror. "No, please!"

"Oh yes," she said with an evil smile. "You'll look fantastic."

Ten minutes later the poor boy's waist was crushed in a tight red lace corset that barely let him breath. A matching set of bra and panties covered his glued silicon breast and his tiny chastity device. Six garter straps came down from the corset and held up a pair of sheer floral-patterned stockings.

"My favorite part about this corset is that you can't even unlace it without someone else's help. Maybe you could get Luke to take care of that for you, right?"

Paul stood helplessly. He didn't know what to say.

"Let me think about the dress," she continued, looking at the clothes in his wardrobe. "We need something red, short and tight-fitting."

"Couldn't I wear the red pleated gown?" he dared to say, suggesting the only modest garment he could think.

"That's out of the question, babe. The pleated one almost comes down to your knees. You're going out on a date, not to church."

In the end she chose a red pencil dress that hugged his body like a glove. The cleavage wasn't too deep, in order to hide his fake breast, but all the rest was slutty. The skirt reached his mid-thigh and barely covered his stocking tops, so at the slightest movement he'd expose them. Altogether, it was basically like going around naked.

"These are a perfect match," said Julia, handing him a pair of shoes.

Paul's heart sank. It was a pair of red shiny platform stiletto heels with ankle straps. He'd worn them only once before and he remembered well that it was like walking on stilts. His poor feet would ache terribly.

"Le me help you with those," she said, ignoring his moans.

He tried to walk around the room. He needed all his concentration to keep balance on the heels, and he noticed the dress's skirt tended to ride up and expose his stocking tops. That outfit was a real nightmare!

"We need a final touch," was Julia's only comment.

She opened a closet and took out a big red hair bow. It was huge and flashy. Even a little girl would have probably refused to put it on, but Paul's didn't have any choice. He sat down in silence and let his mistress tie it on the back of his hair.

"Wonderful! Now let's do your make-up."

During those long years of feminization, Paul had learned to do his own make-up, of course, but Julia usually insisted to do it on great occasions. It meant less work for him, but the downside was that she always overdid it. As he imagined, this time wasn't an exception, and when she was finished he felt like a Barbie doll. She used them all: foundation, concealer, highlighter, blush, eye pencil, eyeliner, eye shadow, mascara, false eyelashes, lip liner, and last but not least a bright red lipstick.

"I thought it was a date, not a wedding," he said bitterly.

"Not yet, honey," she said, making his blood run cold.

While he was still trying to understand if she was just joking, she started to select his jewelry. She picked up a pair of long silver earrings with heart-shaped pendants, a matching necklace, a series of bracelets, and a few rings. Paul now began to realize how a Christmas tree must feel while being decorated in December.

"Oh, and before I forget," she added, opening another closet. "You'd better wear this one too, or the night might turn out very uncomfortable for you."

Paul gasped as he saw what she was holding. It was a big long ass plug, bigger than anything he'd put on before. And as a cherry on top, it was bright red too. Julia lubed it well with a water-based product and told him to bend over, which wasn't easy in a tight corset. Once he finally managed to get into the right position, she lifted his dress and lowered his panties. He couldn't help but cry out in pain as she inserted it up in his body, forcing his muscles to widen take it all.

"Don't be such a baby," she scolded him. "You'll thank me later for this."

She told him to stand up and to follow her to the door. Before they left, she gave him a little red purse and a stylish black coat. Paul was more than happy to put it on. It was short and ended well above his knees, but it made him feel less exposed.

"It's a shame to hide your pretty dress," said Julia with a sad smile. "But I don't want my little girl to freeze to death, either. It's going to be a cold night."

She opened the door and headed for the street. Paul did his best to keep up, fighting his way down the stairs in his impossible heels. Once he finally reached the building's entrance, his feet were already on fire. He had no idea of how he could survive a whole night in those awful shoes. He wrapped himself tightly in his coat and followed her outside. But to his surprise, Julia didn't go to get her car.

"You just need to wait here on the sidewalk, honey," she said smiling. "Luke will come soon to pick you up."

Paul's face lost what little was left of its color. He hated the idea of being left alone on the street. He clung to his purse, trying to find some courage.

"There's still one little thing, baby," said Julia. "You need to take this."

She put a small metal object in his hand. It was sharp and cold. Paul looked down and startled. It was a tiny steel key. He looked at her in disbelief.

"Oh now, don't look so surprised. Did you really think Anne would trust Luke with his own chastity key? He'd probably run off to fuck a few hookers before he even remembers to come and get you. Keep it safe in your purse and use it when it's time."

That said, she turned around and went back inside. Paul felt the cold night wind breezing against his legs and shivered. His little coat and sheer stockings were hardly enough to protect him from such a wintry weather. He dreamed about wearing a pair of thick manly jeans, but this made him feel even worse. It had been months since the last time Julia had let him wear pants, and even then they had been female ones.

He remembered that he was still holding the key in his hand, so he opened his purse and put it inside. He checked the rest of its contents. He found paper tissues, a hand sanitizer, some peppermints, a basic make-up kit, a spare pair of sheer stockings, a tiny bottle of water-based lube, and a package of extra-large condoms. There was neither a wallet, nor a mobile phone, which meant he didn't have any money or documents, and couldn't even make a call in case of emergencies.

Luckily for him, it was just a quiet residential street, so he managed to master his nervousness. The few passers-by didn't bother him too much, even though his ridiculous hair bow and his platform high heels didn't fail to catch everyone's attention. Trying to ignore their stares, he concentrated on the street. A few cars passed by, but he didn't see Luke. He was starting to freeze and he began to walk back and forth on the sidewalk to keep warm. He didn't use to suffer so much for such things, but ever since Julia had forced him to lose so much weight, he'd become much more sensitive to the cold.

He didn't even have a watch, so he couldn't tell how much time had passed, but in the end, after what felt like an hour, Luke arrived. He was driving a beautiful sports car, which must cost a fortune. Paul sighed as he looked at it, since he loved nice cars, but Julia didn't even allow him to drive a motor scooter. Luke pulled over, got out of the car and approached him with a cold smile on his face.

"Good evening, Cecily," he said, using his female name.

"He... hello," said Paul, who was already terrified.

Luke wasn't just a big man. He was huge. He was tall as a basketball player, but strong and sturdy as a footballer. Not even the elegant dark suit that he was wearing could hide his incredible amount of muscles. Even on high heels, Paul felt like a child next to him. The fact that during their last encounter he had only needed ten seconds and a single arm to knock him down didn't exactly help his mood. Luke bent down and kissed him on both cheeks. Paul startled as he felt the man's short beard sting his soft skin.

"Get in the car," he said. "I've got a reservation in a fancy restaurant. You'll like it."

Paul did as told and took place on the passenger's seat. Even such a simple action wasn't that simple in his current outfit. He needed to keep balance on the high heels, prevent his miniskirt from exposing his underwear, and of course do it in a corset. Luke noticed his discomfort and smiled for a moment, but then he turned serious again. It was obvious he didn't like the idea of spending his chastity free time with another man, even though a feminine one like Paul.

"Pretty dress," he said as he started the car.

"Ahem... thank you," said the boy, fixing his skirt as a reaction. No matter how much he tried, the short dress kept riding up and exposing the lace stocking tops.

"How long have you been locked up?" asked Luke.

Paul sighed. "Seven months."

Luke whistled in surprise. "I don't know how you do it. I've earned a release every month, but I can barely make it anyway."

Paul cocked his head. "Well, the testosterone blockers and the estrogens help a lot. She uses the strap-on too, but I haven't managed to come that way yet."

Luke couldn't help but laugh at the idea.

"Why do you let her do this to you?" he asked.

"Why do you? You could just throw Anne on the bed and fuck her whenever you want."

"Fair enough," he said, and he laughed again.

A few minutes later they stopped in front of a nice seafood restaurant. Their little talk had shaken Luke, because he hurried to open Paul's door and help him get out of the car. On a normal day the boy would've found it humiliating, but he was suffering so much in his outfit that he was just glad to take his hand.

"You'd better behave as a perfect lady," warned him Luke looking him straight in the eyes. "If anyone finds out you're a boy, I swear I'll make you pay for it."

Paul swallowed hard and nodded, white as a sheet. He startled as the man took his arm and led him to the entrance. He was so scared he thought he might throw out. Somehow, instead, he managed to resist and he followed Luke inside. A polite waiter greeted them and offered to take their coats. Reluctantly, Paul took off his black coat and exposed his minidress. The glimpse of lust that crossed the waiter's face caused him to blush even more. He tried to pull down his skirt, but it was useless.

As they followed the waiter to their table, the poor boy could feel all the men in the room -- and most of the women too -- eating him with their eyes. He couldn't blame them, of course. Even though they were in an upper class restaurant, his dress couldn't possibly go unnoticed. He was relieved to sit down and have some cover from all those eager eyes. He crossed his legs as Julia taught him and tried to smile.

The dinner was awful. Luke couldn't care less about the food or his company and just wanted to go home as soon as possible. Paul ordered an expensive dish, but the corset and the stress got to his stomach and he could barely touch the food. As if all of this weren't enough, he had to keep up his act too, so he pretended to have fun and giggled every time Luke talked, even though he wasn't funny at all.

"Do you have it?" asked Luke while they were waiting for the check.

Paul blushed and nodded. He took his purse with his trembling hands and looked for the little metal key. He was so scared that he needed a while to find it, but then he took it and placed it on the table. Luke's eyes sparkled and he probably had an erection attempt, because he groaned and looked very angry.

"Let's go," he said as soon as he had paid.

Paul followed him to the car with the same enthusiasm as a man walking to his own execution. He could barely stand on his heels and he felt the corset squeezing his lungs. He was so upset he didn't even look where they were going. After a while, they stopped in what looked like a hotel's parking lot.

"Where... where are we?" he asked in a feeble voice.

"Anne needs the house," said Luke. "We're going to spend the night here."

Now he looked very excited. He took their room's key and even grabbed Paul's arm to make him walk faster. When they were finally inside there was a grim on his face. He unfastened his belt and lowered his pants. His chastity cage -- much bigger than Paul's -- looked like it was going to break under the pressure of his massive erection. The boy stared at it with his mouth open.

"What are you waiting for?" asked Luke angrily. "Open it!"

Paul tried to do his best, but his finger trembled so much that he needed a lot of time to finally insert the key in the locket. As soon as he took off the cage, Luke's cock grew so much that it almost reached his face. It was the biggest member he'd ever seen. It was so huge that his tiny penis didn't even qualify as such in comparison.

"You know what to do," he said.

"I... I can't," tried to say the boy.

"Look, silly boy, either you do it willingly, or I'll have to force you, but the second option comes with a spanking."

The idea of the man's giant hands hitting his poor bottom was enough to force him to comply. He stretched his right hand and tried to take the massive cock, but it was too big for just one hand. He needed to use them both to grab it. Julia had forced him to practice on a dildo many times, but the nervousness made it difficult to remember the tricks he'd learned. He did his best, though, and soon the cock was even harder and longer.

"Take it in your mouth," ordered Luke.

"Please," said Paul, feeling the first tears in his eyes.

"Do it now!"

He closed the eyes and kissed the tip. Then, he slowly opened his mouth and touched it with his tongue. Luckily he was a clean man, so it didn't taste too bad. He tried to pretend he was just sucking a dildo, and he did his best to take it in his mouth. Of course, it was much too big for that, but he used his tongue to reach the parts he couldn't swallow. After less than a minute, the member began to pulse.

"Please, not on my..." he started to say, but it was too late.

The pulsing member shot an incredible amount of semen. It went everywhere, from his hair to his dress, and it covered his face. He was forced to close his eyes and he felt the salty liquid entering his mouth. He tried to step back, but Luke's strong arm forced him to stay where he was. The man pushed his cock in his mouth and the poor boy had to swallow what felt like a whole glass of sperm.

"Finally!" screamed Luke, letting him go.

Paul wiped his face with his hands and managed to open his eyes. He felt violated and dirty, and he just wanted to run away. Before he could do anything, though, Luke's cock started to grow again. He looked at it in disbelief. He didn't believe it was possible to have another erection in such a short time.

"Are you ready for the best part?" asked the man.

"What do you mean?" asked Paul horrified.

Luke lifted him without any visible effort and threw him on the bed. The boy knew what was going on and struggled to get away, but the man immobilized him easily and lifted his dress. Then, he tore up his panties, ripping the small lace garment, and he forced his ass to get in the right position to take his cock. He laughed when he saw the dildo and he took it off, making him moan for the discomfort.

"Wait! Wear a condom, please!"

"Are you afraid you might get pregnant, silly boy?" he mocked him. "Don't worry, I haven't fucked anyone in two years. Anne doesn't let me touch her."

And then he pushed his cock in his ass. Paul screamed at the top of his lungs. The pain was almost unbearable. Luke started to move back and forth, ravaging his tight hole with his giant member. Fortunately, despite his previous orgasm he didn't manage to resist more than a couple of minutes and soon he came in his ass. A massive flow of sperm was released into the poor boy's body, filling him up like a stuffed turkey.

This time even Luke needed to recover. He lay down on the bed with a satisfied smile on his bearded face. Paul pulled down his dress and got into a fetal position. He couldn't resist anymore and burst into tears.

"Don't worry, it's normal the first time," said Luke without looking at him. "You'll grow to like it, I think."

The rest of the night wasn't better than the beginning. The horny man managed to have four other orgasms, forcing the boy to take his cock in every possible way and position. When he finally went to sleep it was almost sunrise. With his ass impossibly stretched and his whole body covered in dried male semen, Paul hobbled to the bathroom. At least Luke had helped him take off the awful corset, since a special amount of flexibility was necessary for their last position. He was glad to take a long hot shower.

He had to wash his hair twice to get all the sperm away, but in the end he was clean again. Feeling regenerated, he wrapped up in the hotel's bathrobe and dropped on the bed, trying to stay as far as possible from Luke. He was immensely tired, but he was so upset that he needed a good while to finally get asleep.

"Wake up, sleepyhead!" said Luke.

Paul's head started spinning. He watched the clock on the wall and understood why. He'd been sleeping only for a couple of hours.

"Please, I'm so tired!" he begged.

"It's out of the questions, honey," said the man. "Anne's coming at nine and I want a last good fuck before she locks me back up."

Paul was too tired to argue, so he just stood still and let Luke do what he wanted. Luckily, his ass was still stretched and the penetration wasn't so painful as the previous night. Still, he was happy when he finally came and let him go.