by John Dylena
“That’s right, Jake; cum from being fucked in the ass like the girl you are!”
Her insult didn’t bother him in the slightest. He was too absorbed by the pleasure from being anally raped to care.
His hips jerked, and he blew his load all over the hard ground. His cum went everywhere, from his stocking-clad legs to his heels and the ground underneath him. It was better than the orgasm he’d had that morning, and this was from not only being dressed as a slutty maid, but by being fucked like one too. If they kept this up, he knew in his mind that he’d eventually submit.
Much to his disappointment, the punishment ended there. It was when she slowly pulled out that Jake realized that the Master was watching the entire time.
Jake’s face turned bright red with embarrassment, and the old man laughed. It was an unsettling laugh, one the built up from just a chuckle to a howl.
“Cage him,” he said to Erica.
“Yes, my Master.”
Erica backed away from John and walked around behind him. He could hear her shuffling around, once again opening and closing drawers. Her footsteps grew louder and she walked in front of him.
“What is that?”
“This Jake, is a chastity cage.” Erica smirked and knelt down in front of him. She bowed under the stocks and moved between his legs. “You made quite a mess down here Jake.”
She tiptoed around the puddles of cum and held his flaccid dick in her hands. The clear plastic was cold on his skin and he twitched. The cage was tight and uncomfortable. The sheath that held his penis was directed downward, making it very difficult to piss standing.
He heard the click of the padlock and Erica backed away, wiping her hands.
The Master stood up and walked toward Jake. He looked up at the old man, confused. Jake didn’t know what to feel. Deep down, he was pissed at Mr. Smith for not only what he did to Anne and Sarah, but what he promised to do to him.
The old man lured Jake in with what was most likely a lie about a six-figure income. He even got Jake to dress up like a woman in this slutty maid outfit, complete with a wig and makeup. He wanted to run away, to escape this horrid place, yet at the same time, he wanted to stay. Jake wanted to be there—to work and dress like a maid—all to serve the Master.
The old man walked up to him and put his hand on Jake’s head.
“Rest now, Jake. Tomorrow is a big day.”
Jake’s eyelids felt heavy, and he drifted off to sleep.
He woke up the following morning back in his bedroom. Anne and Sarah were there, urging him to get out of bed. His head ached. He felt congested and light headed. Anne reached out and pulled the sheets off of him.
“Get up, Jake. You mustn’t keep the Master waiting.”
“Anne… I… I’m sorry,” he grumbled. His memories from the night before trickled in. His asshole was sore, yet he felt no hatred towards the Master. Why? Why can’t I be angry?
He sat up and he felt a slight tug on his chest. He looked down and saw two mounds on his chest, breasts that were about a B-cup.
Jake looked past his chest down the rest of his body. All the hair on his body was gone, replaced by smooth, fair skin that shined like silk. The cage was still on his manhood, yet it wasn’t uncomfortable. The clear plastic didn’t feel tight or constrictive, but the gold padlock was still attached.
He reached up and scratched his neck. His longer nails caught him by surprise, and he broke his skin. He looked down at his filed and polished nails. Their surfaces were smooth and shined with a clear coat of gloss.
His fingers returned to his neck and found the choker still around it. The black material was smooth, and though his fingers traced it all the way around, he found no evidence of a break in the material. It was sealed around his neck with no way to take it off.
Jake’s delicate fingers stopped when they touched the gem on the front of the collar and he caught himself smiling. Why does this choker make me feel happy?! What is happening to me?!
“Time to get dressed, Jake.”
He looked over at Sarah, who held the corset in her hands.
Jake climbed out of bed and let the women dress him. Unlike the previous day, he felt no arousal coming from the clothes or the beautiful women dressing him.
They’re not women. They’re men, just like me. But why do I keep thinking of them as women?
He slipped on the high heels and followed the two of them over to the vanity in his bathroom.
When he sat down in front of the mirror, he saw the changes in his face. Even though he still looked like a man, he looked more androgynous and less masculine than he did before. His hair was longer, but it was still too short, and they gave him the wig. Anne and Sarah used less makeup than the day before, but the outcome was even better than it was then.
I look more feminine today, Jake thought, staring at his reflection. Even with the amazing job they did yesterday, I look more like a woman today.
He stood up and followed the two maids out of his bedroom and into the dining room where the Master ate his breakfast. Jake froze when his eyes caught sight of the old man. He’s not that old anymore.
Last night, the Master had looked to be close to eighty. Today, he appeared closer to fifty. There was far more color in his hair and skin, and his cane was nowhere to be seen.
“Ah, Jake. Good morning. How are you feeling?”
“I feel fine, Master,” he said as he involuntarily curtsied. My body is moving on its own again!
“That’s good to hear. Today, you’ll be shadowing Sarah. She’ll be taking over your training.”
Jake and Sarah bowed, and he followed her out of the dining room. Anne remained by the Master’s side, and Erica was nowhere to be seen.
Jake spent the remainder of the day with Sarah. They dusted, vacuumed, and polished the fancy dinnerware. Several times throughout the day, Jake’s eyes looked upon Sarah’s ample bust and round ass when she bent over, but not once did he lust after her. His dick remained flaccid in its cage and he only saw her as a fellow maid, not a sexual object.
Is it because she’s really a guy? he wondered. No. Even with her package still intact, she’s got a beautiful body. Why am I no longer sexually attracted to her?
His mind wandered off many times during his duties, and as the hours passed, he become more and more frustrated.
Jake was finally starting to feel angry and decided to do something about it. It wasn’t too late. He could still escape, and maybe his body will turn back to normal. The choker could be cut off with some scissors, and the thin padlock could easily be removed with a hacksaw.
Evening came. Jake and Sarah brought out the Master’s dinner and patiently waited for him to finish eating. Sarah took the tray full of empty dishes, and Jake remained by the table.
“Would you like some dessert?” he asked.
“Why, yes, Jake. That sounds good.” Jake bowed and turned to leave, but the Master stopped him. “Where are you going?”
“To get some dessert, Master.”
“No, no. That’s not what I want.”
Jake’s face turned red when the Master spread his legs and unzipped his trousers. His eyes spotted the rather large dick that had started to harden.
“I would like for you to give me a blowjob, Jacqueline.” Jake hesitated, sure he’d misheard him, but The Master looked up at him expectantly. “Well? What are you waiting for, Jacqueline?”
There it is again: Jacqueline. Is that my new name? A woman needs a female name. ‘Jake’ is no name for a maid. Wait, what the hell am I thinking!?
Jake looked down at the old man’s dick. It was exposed and… big.
The Master’s dick looks rather delicious. Jake felt his mouth water as he stared at the monster between the Master’s legs.
No, Jake, fight it! You must escape.
Jake smiled and lifted his heeled foot. He lunged forward and kicked Mr. Smith right in the chest. The old man cried out as his chair toppled back.
Run!
Jake remembered where the front door was. He sprinted as fast as he could in the high heels, not thinking once about removing them before running any further. He rounded the corner and the front doors came into view. The brass knobs were so close.
Jake reached out, his fingers inched closer and closer. I’m almost there. I’m so close—
His body fell to the floor hard. The Master tackled him like a linebacker. He hit Jake so hard that his breath left his lungs and he collapsed against the hardwood floor, coughing, gasping for air. Jake lifted his head to breathe, but the Master’s right hand struck him hard across the face, knocking him out.
“You almost escaped, Jake,” the Master said to Jake’s unconscious body. “Just think, if you had reached those knobs and stepped through those doors, you would’ve been free.”
Anne, Sarah, and Erica came into the entryway as the Master climbed up off of Jake’s body.
“Bring him to the dungeon and prep his body.”
“Yes, Master,” the three maids replied.
Jake opened his eyes to nothing but blackness. He quickly tossed aside the theory of being blind when he felt the blindfold around his head. His wrists and ankles were once again bound, but he wasn’t in the stocks. He was seated, his legs spread apart and lifted high off the ground. His blood ran cold. Had they put him in a set of gynecologist’s stirrups?
“Hello?” he called out, shocked to find his mouth ungagged.
“Hello, Jake,” the Master replied. “Glad to see you’re awake. Are you ready for your punishment?”
“Go to hell.”
“Feisty. Once again, I underestimated you. But a wild horse must be broken if you want to ride her.”
Jake yelped at the cold application of the lube in and around his asshole. He heard the sounds of something being wheeled toward him, followed by the sound of something switching on and gears moving.
“What are you doing?” His answer came seconds later in the form of a dildo sliding into his ass.
“You’re hooked up to a fuck machine, Jake. It will penetrate you endlessly until the power is turned off. I can adjust the speed, but for now we’ll start off slow.”
“Fuck yo—OH!” He moaned as the phallus slid all the way in and pulled out. The Master wheeled the mechanism in closer to where the dick would never come all the way out of Jake’s ass. He wrestled with the restraints, but they wouldn’t budge. It was when he was moving that he felt something taped to his chest.
Oh no.
Another switch flipped on, and the vibrators attached to his nipples came alive. Jake screamed.
This went on for several minutes. At first, the vibrators were weak and low, but after a couple of minutes, the Master turned the juice up on them. The machine violating his ass picked up the pace, too.
Minutes later, the machine penetrated him at full speed, and the vibrators buzzed at the highest level. The removal of his sight improved his other senses, and his mind swam in erotic sensory overload.
“I’ll be back to get you in an hour. Good luck, Jake.”
“No… please. Don’t leave me here,” he begged. “Please, Master.”
The old man said nothing, and Jake heard the sounds of footsteps getting quieter until the door slammed shut.
Jake was all alone. His body twitched and spasmed from the toys. The plastic cage prevented his dick from getting hard, but it didn’t stop him from ejaculating. His cum oozed out of the head of his flaccid dick, but there was no sweet release.
Like a jackhammer breaking apart concrete, the fuck machine chipped away at Jake’s willpower. In only twenty minutes, his mind broke, and he submitted to the pleasure.
“Oh yeah! Fuck me, Master! Fuck your Jacqueline! Harder!” he yelled into the blackness.
When the door finally opened and the Master returned, Jake was a drooling mess. His tongue hung out of the side of his mouth and his eyes stared blankly. A stupid grin covered his face and cum pooled on the floor.
The machine clicked off, and the penetration stopped.
“No please! I want more! Don’t make it stop!” He whined like an addict who had been refused another dose of a drug.
The Master helped Jake off of the chair and out of the dungeon. Jake’s legs were weak, and he could barely stand.
Outside of the dungeon, Anne, Sarah, and Erica waited for him. They took Jake from the Master and carried him into his bedroom where he fell asleep begging for the Master’s cock.
“Will he be okay, Master?” Anne asked.
“She’ll be fine,” he said with a smile.
Jake woke up the following morning once again in his bed. However, this time Anne and Sarah were nowhere to be seen. It was just him.
He lifted his head off of the pillows, and his long brown hair tickled his back and shoulders. He felt the tug on his chest and looked down to see a pair of D-cup breasts bouncing on his chest. His hands squeezed the cream-colored mounds and his fingers played with his perky nipples.
A soft moan escaped his supple lips, and looking past his breasts, he saw his narrow waist and wide hips. The clear plastic cage between them was gone. His dick and balls were free, but they were shriveled up and pathetic looking.
He climbed up out of bed and got dressed. The corset amplified his cleavage and his black dress barely contained his jiggly breasts.
Jake slid on his heels and sat down at the vanity. In his reflection, he saw a woman. There was no hint of masculinity left in his face.
Jake did his makeup on his own. The process was as natural as breathing or walking. He styled his hair and his eyes spotted the choker around his neck. My Master, he thought. He smiled as he rubbed the gem and got up.
Not once did he think about how weird it was that he was doing his own makeup, or how gracefully he moved in the high heels. He didn’t care that his hips bounced with each step, or that his breasts were barely contained in the thin black dress.
He walked out of his bedroom and into the dining room where the Master ate his breakfast. Hearing the sounds of high heels walking toward him, the Master put aside his newspaper and looked at his brunette maid.
Jake couldn’t believe it. The Master looked to be no older than thirty. Not only that, but he had a hard time thinking about anything other than how handsome he looked.
“Morning, Jacqueline,” he said, taking her in.
Jacqueline curtsied. “I am here to serve you, Master. Tell me what it is you desire. I am yours.”
The Master set his paper down on the table and smiled at his new maid. He slid his chair away from the table and unzipped his pants.
Jacqueline stared at his meaty dick hungrily and her mouth watered. The Master grew rock hard as he stared at her. She had long brown hair with dark brown eyes. Her lips were painted red and wrapped around her neck was a black choker with a multi-colored tourmaline.
The maid knelt down in front of him and wrapped her luscious, ruby red lips around his dick. She had no qualms about pleasuring him. She only lived to serve her Master.
CHAPTER ONE
The Experiment
THE EXPERIMENT
CHAPTER I: THE DEAL
After hours of flipping through the phone book and searching high and low on the internet, Reed dialed the number for the professional dominatrix. She came highly recommended and her “areas of expertise” were exactly what he was looking for. He held his breath, waiting for the other end to pick up.
“Hi, is this Arina?” He said into the phone, hearing the other end pick up.
There was a moment’s hesitation, followed by the sound of shuffling papers. “Yes, this is Lady Arina, how may I help you today?”
“Yea, I was wondering if I could… set up an appointment?” His mouth was dry as he fought to say coherent.
“Let me check my schedule… how about 1pm today?”
“Sounds good, I’ll be there.” He hung up the phone, letting out a deep sigh of relief. Recently, a certain topic had kept his mind occupied for some time and in
order to put it to rest, he decided to seek an expert on the subject. The topic, “is a man’s greatest fear really that of becoming a woman?” was something he happened to stumble upon during one of his many internet sessions. Days after reading the discussion, which had maybe three comments then died, the idea still ragged on his mind. He looked up books in the library and searched for articles on the internet, but whatever he found didn’t help in the slightest bit. About to give up, he decided to try one last person: a dominatrix. He figured it would be odd for someone to see a dominatrix solely for a philosophical discussion and hoped this particular one, who came highly recommended, was a learned person.
He slouched and watched the clock.
The parking lot was empty except for a few cars scattered around the industrial complex. He looked down at the piece of paper in his hand with the address written down on it and back at the building.
No turning back.
He opened the door and headed inside, stepping into what appeared to be a waiting room. He had high hopes for this place; it was located in a very nice part of town, lots of wealthy people, no crime, and a very clean area. From the outside, it looked like any other building in the complex, but the windows were blacked out so no one can see inside. There were only a handful of parking spots directly in front.
When he walked in, he was instantly greeted by a woman who stood behind the reception desk. She was hunched over the computer so he didn’t see her when he walked in. Her welcome startled him slightly. She walked out from behind the counter and greeted him, dressed in full black leather: thigh high boots, mini skirt, tube top, and any exposed skin covered in fishnets. Her blonde hair was pulled back, and her green eyes glowed like emeralds.
“Hi, are you Reed?”
“Yes, you must be Arina,” he replied.
“That's Mistress Arina.”
He rubbed his head. “Apologies.”
Her face relaxed. “Welcome, since this is your first time here, follow me to the interview room… It’s where I do my consultations and where the client tells me what he or she is looking for.” She opened the door next to the desk and pointed down the hall. “First door on the right.”
