Lipstick & Miniskirts

by John Dylena

  “I will be back in an hour,” the maid said through the door.

  “See ya then.”

  He received no reply; the only sound was that of her heels clicking on the wooden floors.

  Jake turned around and took in the room. It was a large bedroom with a queen-sized, four-post bed. The floors were comprised of wooden slats, but there were several large rugs placed throughout. In addition to the bed, there was a dresser, two night stands with lamps, a full-length mirror, and a window with blinds. On the wall to his right were the sliding closet doors, and at the far end of the same wall was the door to the bathroom.

  Before he got any cleaning done, he figured it would be best to use the bathroom. Jake walked past the closet and opened the door to the restroom. The smell hit him like a slap to the face. He slammed the door shut and returned to the bedroom.

  “Christ, it smells like a frat house after a weekend-long party!” He covered his mouth with his shirt and he went back into the bathroom.

  Square, light blue tiles decorated the floor, and the appliances were all cream-colored porcelain. There was a toilet, bathtub, shower, and a sink. In addition to the appliances, there was a wooden shelf and a mirror on the wall behind the sink. The small window was closed, trapping the foul stench in the bathroom. Every surface was covered in grime and muck. The toilet seat was up and the bowl was stained. There were spots on the ground, the work of a man with bad aim.

  Jake tiptoed across the tile and looked away from the dirty toilet as he relieved himself. He relaxed when the toilet at least flushed properly. The water that came out of the faucet was yellow at first, but after a couple of seconds, it turned clear. He washed his hands and made up his mind to clean the bathroom first, as it would be better to get the harder task done earlier.

  If it wasn’t for the six-figure salary that the old man was offering, I’d be out of here.

  He left the bathroom door open and entered the bedroom.

  Sarah said all the items would be in the closet, as well as a change of clothes. It would probably be a good idea to change.

  Jake slid open the closet doors and stared at the contents inside. Maybe not.

  The first things he saw were the tools: two vacuum cleaners, a wet mop, a duster, a bottle of glass cleaner, and everything else a house cleaner could ever want. Hanging up next to the cleaning items was the outfit Sarah had suggested.

  I thought I saw her grin when she told me about it.

  The outfit was none other than the maid costume that Sarah and Anne both wore: a tight black dress, a black corset with garters, and a white petticoat.

  On the ground below the clothes was a shoe box. Curious, Jake reached down and opened it. Inside was a pair of dark stockings still in their packaging, and underneath those were black patent pumps.

  “Heh, like I’d ever wear these,” Jake laughed to himself.

  He put the shoe box back, rolled up the sleeves of his shirt, and started cleaning. It took him three hours, but he eventually cleaned the entire the room and bathroom. After putting the items back in the closet, he sat down on the chair and waited for Sarah to return for a third time.

  Right on schedule, he heard a knock on the door.

  “I’m done,” he called out. The knob shook, then turned, and Sarah walked into the bedroom.

  “I was hoping you’d be in the outfit,” she said to him, smirking.

  “Nope.”

  “I must inspect the quality of your cleaning.”

  “Be my guest.”

  Jake remained in the chair, following Sarah with his eyes as she moved about the room. The maid checked everything from the smoothness of the sheets on the bed to the dust on the shelves. She disappeared into the bathroom and returned a few minutes later.

  “The Master will be pleased. You did a very good job, Master Jake.”

  “Thank you,” he replied, bowing his head.

  “If you’ll follow me, I am to take you back to him and inform him of my judgment.”

  “Wonderful! That is good to hear.” Mr. Smith sat forward in his large, red velvet chair and rested his hands on the cane between his legs. The chair was turned toward the door this time, instead of facing the fireplace like it was when Jake had first met him. The Master had just finished listening to Sarah’s report on Jake’s cleaning job.

  “So, Jake, it seems you’ve passed with flying colors. How would you like to work here?”

  “I’d love to. This is an amazing house, and I’d much like to see more of it.”

  “Perfect. Sarah, would you be so kind to lead Jake here on a tour? Make sure you show him all of the house.”

  “As you wish, Master.” She bowed and beckoned Jake to follow her.

  The maid led Jake on a tour of the entire house. He knew the house was big just from when he looked up at it from the outside, but he didn’t realize it was this big.

  In addition to the many guest rooms, Sarah showed Jake the master bedroom. The room put all other bedrooms to shame. The bed was bigger than any he had ever seen and the bathroom itself looked like it had cost a million dollars to build.

  There were more than just bedrooms and bathrooms in this hotel-sized mansion. She showed him the game room, which included an antique billiards table, fully-stocked bar, flatscreen TV, and a poker table, as well as several couches.

  Sarah led him up and around. The mansion had a fully-stocked kitchen, where he was introduced to the third maid, a red-head by the name of Erica. There were several living rooms, a large library, a dining room, and a private theater.

  “Where do you guys sleep?” he asked.

  “We each have our own bedroom and bathroom at the end of that hall. They are nice rooms, smaller than the guest rooms, but still spacious. That door leads to the basement. There’s nothing down there but storage.”

  Jake kept his eyes on the door to the basement as they walked down the hall. What’s stored down there that justifies a deadbolt and padlock?

  They came around to the back of the house and stood in another sitting room. This one was designed differently from the rest. There were many small tables and chairs in addition to the couches. Jake could only assume that this was where Mr. Smith might host a party. There was a bar at one end and a narrow hallway that led to the kitchen. But that wasn’t what held his attention.

  The entire back wall was glass. Massive windows and several sets of French doors lined the wall, and through them, Jake could see into the backyard.

  Sarah walked up to the main set of doors and opened them. A cold autumn breeze blew into the room. She urged him outside and she closed the doors behind them.

  The doors opened to a patio with chairs and tables with umbrellas jutting out of them. The matching covers were all folded down and wrapped up. On the other end of the patio was a set of stairs that led down to a pool, barbecue, and another patio. The more Jake saw the house, the more it reminded him of the mansion from The Great Gatsby. If this were the ‘Roaring Twenties,’ then Jake was sure Mr. Smith would be Gatsby, and all the best parties would be held there.

  “What’s that building over there?”

  “That is the garage. Only the Master is allowed in there. Come, let us get inside. It is getting rather cold.”

  Jake looked at the maid. Even though she wore a very revealing outfit, she didn’t look the least bit cold. He, on the other hand, was starting to shiver.

  “I’m sure this place would be nice in the summer.”

  “Yes, very much so.”

  They headed back inside and Jake stopped and stood by one of the chairs.

  “Master Jake,” Sarah said. “Are you all right?”

  “I’m sorry. I just feel a little… light… headed…” His voice trailed off as he fell sideways and landed safely on one of the couches.

  Sarah watched as he collapsed. She walked over toward him and made sure he was out cold before walking over to the bar. She picked up the small brass bell and rang it. A minute or so later, Anne and Erica appeared
and joined their fellow maid by the couch.

  “Take him to his room,” Erica ordered.

  Anne and Sarah bowed their heads, and the three of them lifted Jake’s body off of the couch and down the hallway into their quarters.

  They opened the door to one of the vacant rooms and set his body down on the bed. They stripped his clothes off of him and then covered his naked body with the sheets.

  Jake remained unconscious for the rest of the day and slept straight through the night. It was early morning when his eyes finally opened back up.

  Jake woke up to the soft touch of the maids. They pulled the covers off of him and he twisted and turned and fought to stay asleep just a little bit longer.

  “Wake up, Jake,” one of them said.

  “You need to get ready,” said another.

  His eyes opened slowly and he sat up in the bed. Erica, Anne, and Sarah were all in his room waiting for him to get out of bed. He looked down at the sheets and felt the soft fabric on his skin. He realized that he was completely naked.

  “What… Where are my clothes?”

  “They are being cleaned,” Anne said.

  “What happened to me?”

  Erica folded her arms. “You collapsed, Jake. We believe it was a combination of the fumes from the cleaning chemicals and exhaustion from cleaning.”

  That’s odd. Yesterday they called me ‘Master Jake,’ now it’s just ‘Jake’.

  “What happened to ‘Master Jake?’” he asked them.

  “You are no longer our guest, but part of the staff here at the estate,” Erica replied.

  “I see. But where are my clothes?”

  “We are here to help you get dressed,” Sarah answered. “All the clothes you’ll need are here in this closet.”

  She walked away from his bed and slid open the closet door. Jake’s eyes widened when he saw the contents.

  Hanging up in the closet were eight identical black dresses, and two white petticoats and aprons. On the ground in the closet were two shoe boxes. Both contained a pair of black patent pumps.

  Anne opened the top shelf of the dresser and Jake lifted his head to see what lay within.

  “Bras are in this drawer, panties in the other, and stockings in the third,” she explained. “Nighties and other items are in the other drawers.”

  “Like hell am I wearing that outfit.”

  “If you wish, you can take it up with the Master.” Anne said, shooting a glance at Erica.

  “Yes, I’d like to talk to him about this. There was no mention of a required uniform to work here.”

  “As you wish. But you mustn’t speak to the Master naked.” Erica answered, smiling.

  “Where are my clothes?”

  “They are locked away.” Sarah said.

  “So then…”

  “The only clothing you have available is your uniform.” Erica stated.

  Jake stared at the three women and they patiently looked back at him. He had no other choice but to wear the outfit.

  But he knew none of these women, and they knew nothing about him. There was no one that they could tell.

  Think about it, Jake. You’re getting paid six figures—who cares about some stupid uniform? It’s not like anyone you know will see you in it. Just put it on and remember the money.

  “All right,” he finally relented.

  The women said nothing. Instead they bowed to him and nodded at each other. Anne reached into one of the drawers and pulled out the black corset.

  “Jake, please get out of bed.”

  “But—”

  “No buts, please climb out of bed.”

  He swallowed his pride and slid his legs out from under the sheets. He got up off of the bed and stood by it completely naked.

  Anne handed Sarah the corset. She walked over to him and wrapped it around his waist. Jake looked down at the garment as she tightened it. There were cups meant for breasts, and hanging down from the bottom were garter straps. He held his breath as she buttoned up the front and he could feel it shape his body.

  “It is designed so that you can easily put it on and take it off by yourself,” she assured him.

  Jake looked down at the dark-haired maid who was less than a foot away from him. Her skin was soft and smooth, and her makeup was done perfectly. Not only did she look good, but she also smelled good. Her perfume filled his nostrils with a wonderful, yet not overpowering smell.

  “There. Slowly exhale,” she instructed him. He obeyed, and she taught him out to breathe in the constricting lingerie.

  Sarah backed away and Erica stepped forward. In her hands was a pair of black stockings. He didn’t have much body hair, but the stockings were dark enough to hide the sparse strands.

  He sat down on the edge of the bed and watched as she slid the silky thigh-highs up his legs. The material hugged and caressed his calves. He bit his lip and fought the arousal that was slowly building up in his body.

  With the second stocking on his leg, he stood back up, and Erica clipped the garters to the tops. Her head was so close to him. Her fiery orange-red hair was pulled back in a ponytail, giving him the perfect view of her face; her green eyes; her crimson lips.

  Such beautiful lips. If only she would wrap them around my—

  “Now, now, we’ll have none of that,” she said as she stood up. “What’s the matter Jake? The stockings turning you on?”

  His face turned bright red. “No,” he lied.

  Why… Why am I getting turned on by this?!

  Sarah walked around Erica and the red-headed maid backed away. He stared glumly at the object she held in her hands.

  “Do I have to?”

  “Yes, you have to,” Erica said.

  Jake looked back at Sarah and the black lace panties in her hands. The black-haired maid looked away from him, her face slightly red as she handed him the underwear.

  He took them from her and held them between his fingers. The fabric was soft and sheer, and anyone who looked at his groin directly would be able to see his dick pressed up against the material.

  He sighed, stepped into the lacy panties, and pulled them up. They were strangely comfortable, and the fabric on his skin caused his dick to throb. Jake could feel his dick start to harden and he panicked. All three women watched him and Erica smirked. She stepped forward and placed her gloved hand on his groin and gently rubbed it.

  “So you do like wearing these clothes. Well, we’ll see to it that you get a little release later on, but only if you’re good. Understand?”

  “Yes… I do.”

  She pulled her hand away from his groin, and the two other maids’ faces grew bright red. Jake’s dick was rock hard and pressed taut against the lacy panties.

  “Good,” Erica said. “Sarah, hand me the petticoat.”

  Sarah bowed and pulled the fluffy white article of clothing out of the closet. Erica kept her eyes on Jake and she extended her hand. Sarah handed her the frilly piece of the ensemble and she held it out in front of her. He looked at the white petticoat and tilted his head curiously.

  “Go ahead, Jake. Feel how soft the fabric is.”

  He indulged his curiosity and allowed himself to feel the material. His hands shook with nervous energy as the fabric tickled his fingers. The monster in his panties throbbed, and he resisted the urge to touch himself. He put all his focus in preventing the eruption and noticed Anne move across the room to stand next to him.

  The blonde hovered close by with the black dress in her hands. It was identical to the rest: solid black, with a low neckline and short, white ruffles lining the edges. The sleeves were puffy and stopped above his elbow.

  She gave him the dress, and he stepped into it. It was made from a stretchy material that hugged his body and left nothing to the imagination. His corset-enhanced curves were improved by the dress, and the built-in cups made up for his lack of real breasts.

  Anne walked behind him and zipped up the back. The skirt of the dress was loose and waited for the s
upport of the white petticoat in Erica’s hands.

  She knelt down in front of him and placed the petticoat at his stocking-clad feet. He stepped into it, and she pulled it up to his waist. The skirt of the black dress spread out to the sides and the light material that gave his dress volume tickled his thighs.

  “I think we better relieve some pressure before he bursts,” Erica said slyly. “Sarah!”

  Jake watched as Sarah knelt down in front of him. The maid with the emerald choker pulled down his panties and released the beast. He couldn’t see her underneath his dress, but he could feel her. Her soft, velvet glove playfully stroked his pole, but it wasn’t until she wrapped her ruby red lips around his rock hard dick that he went over the edge. He jerked forward and ejaculated into the maid’s mouth.

  Sarah kept her mouth on him and swallowed every drop of his sperm. Jake rocked his head back and opened his mouth as he experienced the greatest orgasm he had ever had—and all from wearing women’s lingerie. The thought bothered him, but the chemical high from the orgasm pushed his worries aside.

  I can’t believe how good that felt. These clothes… I’m actually starting to like wearing them!

  Sarah didn’t once cough or gag as she swallowed his seed. She pulled her lips off of his flaccid dick and stood up, then backed away with her head hung low. With the monster tamed, his Jake’s dick returned to its normal size and disappeared into its lacy den. Jake found it much easier to think and focus now.

  He turned his head toward Anne. In her hands was a shoe box. The lid was gone, and he could see the black patent pumps inside.

  Erica sat him on the edge of the bed and the bottom of his dress lifted up. He put his hands on the fabric and pressed down and the maids giggled.

  Anne knelt down, lifted his right foot up, and slid the high heel onto his foot. The shoe was tight, but the stockings made it slide on easier. She put his foot down and did the same with the other shoe. When both heels were on, she and Erica stood him up.

  Jake wobbled as he tried to balance in the five-inch heels. Erica and Anne held his hands as they led him around the room. It wasn’t long before walking in high heels was comfortable, and he sauntered in front of them.