Lipstick & Miniskirts

by John Dylena

  “Can I go talk to Mr. Smith now?”

  Erica looked him up and down. “Not yet, Jake. You must look presentable, and as you are now, he would be insulted.”

  “So does that mean…?”

  “Yes. You’ll need makeup and a wig. But first, the apron.”

  Erica grabbed the white apron from the closet and put it on him. She tied it behind his back and then led him into the bathroom.

  It was almost as big as the bedroom itself. At one end was a large marble-topped vanity with three angled mirrors and lights. Scattered across the surface was makeup off all types and colors, as well as a plastic head form with a brunette wig atop it.

  Erica sat him down on a small stool, and the three women went to town on his face. They applied everything from foundation and blush to mascara and eyeliner, and finished with a coat of ruby red lipstick, the same color that they all wore.

  For the amount of makeup they put on his face, Jake was shocked at his appearance. He expected to look like a drag queen, but the makeover was flawless and he looked very convincing.

  It wasn’t until they put the styled brunette wig on him that he realized how convincing he looked. To a passerby, he would look like any other woman.

  Jake marveled at his new appearance. He looked at his reflection and didn’t see a man, but a woman staring back; a very beautiful woman.

  “I think he likes his new look,” Erica said, combing his hair. “Don’t you think so, ladies?”

  “You look beautiful,” Anne said.

  “Gorgeous,” Sarah added.

  The three women finished with his makeover. Then they led him out of the bedroom and stopped in the hallway.

  “Remember, Jake: you must address him as Master,” Erica reminded him. He nodded at the red-head and the three maids led him to Mr. Smith’s private library.

  The maids stopped at the door. Erica knocked and waited a moment before opening it. “Master, Jake is here to see you.”

  “Is he dressed?” the old man asked.

  “Yes, he is.”

  “Good. Send him in.”

  Erica stepped out of the room and turned to Jake.

  “The Master will see you,” she said to him.

  He walked past her and entered the room. Erica closed the doors behind him as he moved toward the chair by the fire.

  “You wanted to see me?”

  Jake jumped as the voice came from behind him. He expected Mr. Smith to be in his chair, but instead he stood by one of the bookshelves.

  “You look wonderful, Jake. That uniform looks good on you.”

  “That’s what I wanted to ask you about,” Jake said. “You never said anything about having to dress like one of the maids.”

  “If you are to work as a maid, you must dress like one.” The old man walked past him with a book in his hand. There was something different about him. His movements were smoother and his back was straighter. It was subtle, but the Master looked a little bit younger. It was hard to see with just the fire illuminating the room, but Jake could’ve sworn Mr. Smith’s hair was a little less white, too.

  “I figured I’d have to wear a uniform of sorts, but I didn’t expect this. I mean, isn’t there a male equivalent? Something like a jumpsuit?”

  “I’m sorry, Jake, but that is all there is. If this is too much for you, you could always leave and go back to your old life.” Jake frowned. What does he mean my old life? “However, if it will make you stay, I’ll add an additional fifty-thousand dollars to your salary.”

  “Wait, did you say fifty-thousand?!”

  “I did. Like I said when I first met you, I have a vast amount of wealth. My staff are well taken-care of. And I am desperate. It is a big house, and having a fourth maid would make things much easier for the women.” The old man sat down on the chair and rested the book on his lap and waited for Jake’s reply.

  That was a lot of money. One hundred and fifty thousand, just to dress up like a maid and clean the house?

  Then why am I so hesitant to take his deal? That’s a crap-ton of money. You know what, screw it.

  “I’ll take the deal,” Jake said finally.

  “Very good.”

  In the light of the fire Jake could see the old man’s smile. It looked twisted, and for a brief moment, Jake thought he saw a look of evil on the man’s face. He pushed the thought aside and blamed it on the shadows cast by the fire.

  Mr. Smith reached out and rang his brass bell once, and a couple of seconds later, Erica appeared carrying a long, narrow black box. She walked past Jake, bowed to Mr. Smith, and handed him the box. He took it from her and she moved over to the side of the chair, her eyes on Jake.

  She smirked secretively, but he ignored her. He could tell that she had a dominant personality, and from the way she teased him as he got dressed and how she ordered Anne and Sarah around, Jake assumed that she was not only the head maid, but the Master’s favorite.

  “Come here, Jake,” the old man said as he opened the box.

  Jake moved in front of Mr. Smith, and in the light of the fire, he saw the contents of the box: a black choker identical to the ones the other maids wore. When they’d helped him get dressed earlier, he saw that Erica’s gem was an aquamarine, and when he laid his eyes on the multi-colored tourmaline in his choker, Jake finally grasped their meaning.

  Birthstones. The gem in the stone correlates to the month they became his maids.

  The Master held the choker in his hands and looked up at Jake expectantly. Erica glared at him from beside the chair. Bend down to him, you idiot, her eyes said.

  Jake leaned forward and lowered his head. The Master wrapped the choker around Jake’s neck. It was tight enough to where it he would never forget about it, but it was loose enough to be comfortable.

  The Master leaned back in his chair and Jake straightened up. He lifted his hand and felt the gem with his fingers.

  “Welcome aboard, Jake,” the Master said, clapping his hands together.

  “Thank you, Master,” he replied.

  Erica smiled, and Jake realized what had just happened. He didn’t mean to say those words; they just came right out of him.

  The old man rang his bell three times, and Anne walked into the room.

  “You called, Master?” she asked as she curtsied.

  “Anne, you will be in charge of Jake’s training. He will shadow you and assist you in your daily tasks. Teach him well.”

  “Of course, Master,” she said as she bowed and turned to Jake. “Shall we begin?”

  “Good luck, Jake,” the old man said.

  “Thank you, Master,” he replied, bowing. Once again, his body moved and spoke on its own, and it frightened him.

  He followed Anne out of the private library while Erica remained at the Master’s side.

  Jake stayed close to Anne the entire day. She guided him around the house and told him what the daily tasks were. The blonde maid taught him the proper way to make the bed, to fold sheets and clothes, prepare the Master’s meals, and more.

  “Some things we have to do every day, like dusting and dishes, while other things are done once or twice a week, or even once a month.”

  “There are a lot of bedrooms in this place. Does he get many guests?” Jake asked while helping Anne make one of the many beds.

  “The Master does get guests every now and then. He hosts two large parties, one around Christmas, and the other at the beginning of summer. Those are the busiest times of the year for us.”

  Jake watched her work. She moved with determination, and not once did he catch her slacking in her duties. In fact, she chastised him a couple of times for either slacking off or going too slowly. It was hard for him to take his eyes off of her, not only because of her natural beauty, but because the outfit that she—and he—wore was so sensual.

  By the end of the day, he lusted after the gorgeous blonde, and when they were isolated in a bathroom on the top floor, he made his move.

  “Say Anne,” he sai
d as he moved closer to her.

  “Yes, Jake?”

  “Does he ever let you guys… you know, have fun?”

  “I don’t know what it is you me—”

  Anne set the basket of towels down on the floor, and when she turned toward him, he pressed up against her. He looked deep into her eyes.

  “Jake… we can’t. It’s forbidden.” Her face turned red and he put his hand on her silky smooth leg.

  “We’re alone up here,” he reasoned. “Come on, it’ll be fun.”

  His right hand moved slowly up her milky-white thighs while his left playfully squeezed her ass. He pressed his body against hers and kissed her. He could taste her lipstick, and after a moment of resistance, she caved and kissed him back.

  A soft moan escaped her ruby red lips when his right hand moved under the band of her black lace panties. His dick grew hard in his own panties as they locked lips. His hand moved inwards and he cradled her small balls and three-inch dick.

  Jake pulled away from her soft lips and jumped back.

  “What the hell is that?!” he shouted. He took his eyes off of her and looked at his right hand, acting as if he just touched radioactive material.

  Anne remained against the wall, her face bright red and her knees quaking. She looked away from him, ashamed.

  “I… I…” Her eyes were wet with tears. “I’m sorry, Jake.”

  “But… you’re a man! How? I mean… look at you!”

  “Jake…” Her eyes moved past him and a panic-stricken look came over her face. “No, wait!”

  Jake turned around to see what she was looking at. It all happened so fast. The only thing he remembered before the cloth was pressed to his mouth and the world went black was a bright flash of red hair.

  When Jake eventually came to, he was in a dark room and bound.

  He was light headed and restrained. When his vision cleared, he tried to move his head to get his bearings, but he couldn’t. Looking to his left, he could see that he was locked up in the stocks.

  He tried to move his legs, but attached to his ankles was a spreader bar that forced his legs apart. There were leather cuffs on his ankles, and they were chained to the ground.

  “Hello?!” he yelled. There was no answer, except for the muffled moans of someone else in the room with him. Jake looked over to his right, and out of the corner of his eye he could see that Anne was bound beside him.

  She wore a black leather blindfold and had a bright pink ball gag in her mouth. She was seated, her hands and ankles tied to the chair. The neckline of her dress was pulled down, and taped to her exposed nipples were bullet vibrators.

  Amidst the sounds of the blonde maid’s moans, Jake could hear the buzzing of the vibrators. The way she shifted in her chair, he assumed the little bullets on her chest weren’t the only vibrators tormenting her.

  Her. Even with the unexpected discovery of the package between Anne’s legs, he still thought of the blonde maid as a woman. He took his mind off of his fellow prisoner and turned to the sound of a heavy door opening.

  “Hello?” he called out again.

  “Hello, Jake,” a male voice replied. The Master, Jake thought.

  His suspicions were proven true when the old man with a cane walked in front of him. Erica stood next to him, and behind them was Sarah. Her head hung low and she stood with a very submissive posture. The red-head wore a cocky grin and looked down at Jake.

  “Comfortable?” she asked.

  “Yea, so very,” Jake replied sarcastically. His remark was greeted with a slap to the face from the head maid. Jake laughed and she lifted her hand to hit him again, but stopped. The old man raised his hand and Erica backed down.

  “It is a shame you discovered Anne’s little secret so quickly. I was hoping my magic would affect you sooner.”

  “Magic? What the hell are you talking about, old man?”

  Erica stepped forward and hit him again. Mr. Smith laughed, and in the background, Anne’s moans grew louder.

  “She is a nice girl, isn’t she? It is a shame she had to get punished.” The Master walked over to the bound blonde and stroked her cheek. “But that is what happens when you break the rules.”

  “What did you do to her?”

  “The same thing I did to Sarah. And the same thing I’ll do to you,” he added darkly. “Sarah dear, can you come here?”

  The maid stepped forward and stood next to the old man.

  “Lift up your dress.”

  Jake’s eyes went wide when he saw that Sarah also had a bulge in her panties.

  “Sarah was once Sean, and Anne used to be Alex. Both were men like you, now they’re my maids.”

  Jake now understood why Sarah looked so nostalgic when he asked about her about her choker. She had been thinking about the time before she became a maid—no a slave—to the old man. She and Anne were both probably promised salaries just like he was. Jake could feel the anger building up inside of him.

  “You’re a bastard, you know that?” he spat.

  “I’m a very old and rich bastard,” the Master replied, turning to his red-haired maid. “Erica, please.”

  The red head ran off and quickly returned with a chair for the old man.

  “Was she a man once, too?”

  “No, you fool,” Erica sneered. “I’ve always been a woman, and I’ve always been at my master’s side.”

  “You see, Jake, I’m not actually the eighty-year-old man that I appear to be. In fact, I’m just a little over two-hundred-and-forty. When I turned eighty the first time, it was Erica who found a way to sustain my life, and my youth.”

  “He took me in and saved me from the cold,” Erica explained. “I was an orphan and left to die, but he took care of me, and I promised to take care of him for the rest of his life. When he grew old, I wanted him to live, so I found a way to return his youth to him. All I needed was a young man.” She walked away from the old man’s side and stood next to Sarah.

  The Master tapped his cane on the ground. “Sean was a punk and a pickpocket. He tried to rob me, but I caught and punished him. You see, Jake, the spell works like this: I take the masculinity out of a young man such as yourself, I get my youth back, and the young man’s body turns feminine.”

  “Then how do you explain Erica here?” Jake asked. “How has she earned eternal youth, and yet you are stuck aging?”

  “My Master could never bring himself to kill another, even if it was to save his own life,” Erica said somberly. “The spell he uses is a twist on the one I use. I maintain my immortality by killing a young girl. But he gets to be young again, and in the process, gets a submissive maid. It’s a win-win.”

  “And you expect me to just cave and let you turn me into a chick? You’re dumber than you look.”

  The copper-haired maid smiled. “Oh, don’t worry, Jake. You weren’t the first to be resistant, but like Anne over there, we have ways of making you submit. All it takes is time.”

  Over in the corner, Anne moaned loudly. Erica walked over and lifted up the front of her dress. Her panties were stained with her cum and it started to pool around her crotch.

  “What do you think, Jake? Shall we let her go? I’ve lost count of how many times she’s orgasmed. I’m sure her body is about to give out.”

  “Let her go!” he shouted.

  “If I free her, it’ll be your turn to get punished. Or you could remain locked up for twenty-four hours, and then be set free.”

  Jake grimaced. He could see the poor blonde was in agony, and this was all his fault. If he had only kept his lust in his pants, they wouldn’t be in this situation.

  “Free her,” he said softly.

  “Beg your pardon?” Erica said, holding her hand up to her ear.

  “Let her go,” he said louder.

  She smiled triumphantly. “That’s a good boy.”

  Erica walked behind Anne and switched off the vibrators. She removed the bindings and the blindfold.

  “Sarah, take her to he
r room.”

  Jake watched as Sarah ran over and helped the weakened Anne up off the chair. The color from his face vanished when the blonde stood up and revealed the six-inch vibrating dildo attached to the chair. Her fluids dripped down the insides of her legs as she wobbled off, her knees weak and barely able to support her weight.

  “I’m sorry, Anne,” Jake said as she staggered by. The blonde said nothing, but Jake just figured she was too weak and too mad at him to speak. He might never get an apology from her, and he accepted that.

  Erica kept her eyes on Jake and waited for the two other maids to leave. The heavy door closed, and she grinned wickedly.

  She said nothing as she walked out of sight. Jake could hear the sounds of her digging and going through shelves. A minute or so later, she walked back in front of him and his punishment was clear. Harnessed to the front of Erica’s lace panties was a six-inch strap on.

  “Like I said, Jake, we have ways of making you submit.”

  “Oh, you’ve got to be sh—” Jake’s smart remark was cut off by the rubber phallus sliding into his open mouth.

  “That mouth of yours will get you into trouble. Better get it under control,” Erica said, sliding in and out.

  With Jake’s head restrained, he had no choice but to let the strap on enter his mouth. She pulled it out and he gasped for air. He coughed, and she laughed as she walked around behind him.

  “Thanks for lubing it up.”

  Jake cried out as the fake dick slid into his asshole. He clenched his jaw and grunted, fighting the rubber intruder. She pushed it in deeper and as time went on, his resistance weakened. Jake’s body betrayed him and his asshole opened up, allowing Erica to slide in, his insides providing little resistance. His grunts turned into moans, and Jake found it harder and harder to fight as she pounded his ass.

  “Ohhhh!” he cried out. His mouth hung open and he rocked back in forth. The maid slapped his ass as she slid the strap on all the way in and out. Jake’s dick grew hard in his panties as he neared his very first orgasm from anal.

  Oh god… Why does this feel so good? I… I can’t fight it!

  “I’m going to cum!” he announced, his rock hard dick poking its head out of the top of the lace cage. It bounced up and down as Erica reached around and stroked it.