Lipstick & Miniskirts

by John Dylena

  “Lynessa! You can come down and take a break, I made you some lunch!” Ms. Stevenson yelled from downstairs.

  I stepped into the hallway and yelled back: “Okay, be right down!”

  Moments later, Ms. Stevenson could hear the clicking of my heels on the wood floors upstairs. She couldn’t help but laugh a little at the sound of it, and at the fact that she managed to blackmail me into being her maid for the day.

  “There’s some sandwiches and lemonade in the kitchen. Help yourself.”

  “Thank you, ma’am,” I replied, adding a little bow. She watched me sit down and enjoy my lunch and the break from the servitude.

  “How much more work do you have, Lynessa?”

  “Not much,” I replied. “Just a little vacuuming, and then I have to finish cleaning the master bathroom.”

  An hour or so later, I finished vacuuming and when the master bathroom was spotless, I came downstairs and sat down on the couch next to Janet.

  “All done?”

  “Yes, ma’am,” I answered.

  “Good. Come with me.” I followed her upstairs to her bedroom. “Okay, go into the bathroom and change out of that outfit, then wait for me to call for you.”

  “Umm, okay,” I said, slightly confused.

  She’s up to something.

  While I was in the bathroom, she quickly went into her closet and picked out a new outfit for me. I had finished stripping and was standing naked in her bathroom waiting. She opened the door and handed me some clothes.

  “Here, change into this. Clean up a little bit and redo your makeup.”

  The new outfit consisted of a black and red lace bra, matching panties and garter belt, and black fishnet stockings. I put the breast forms into the bra and tidied up my makeup.

  “All done?” she asked through the door.

  “Yes, ma’am.”

  “Good, put these on, too.” She handed me the same pair of hooker heels I wore earlier in the week. I quietly sighed, not wanting her to hear my protest, and put them on. However, this time they seemed strangely more comfortable than when I had previously wore them.

  Must’ve been due to the heels I wore all day today.

  “Okay, Ms. Stevenson,” I called out.

  “I told you to call me Janet!” she said with a little annoyance in her voice.

  “Okay, Janet, I'm all dressed.”

  “Good. I'm all ready, too. Come on out.”

  Her words worried me. All ready for what? I gulped and opened the door.

  “Janet?”

  “Over here, hun.”

  I turned and saw her on the bed. She was dressed in a really sexy and provocative outfit. A weak-minded man would’ve been ensnared instantly.

  “J-Janet? What are you doing?” I asked.

  “Oh, Lynessa, watching you do your work and all the video footage I have of you drove me insane! I gotta have you!” For some strange reason, I couldn’t look away. She was super hot already, but seeing her in that outfit drove me crazy.

  What are you doing, John? You can't! But the little voice in my head wasn’t strong enough, and I gave into my carnal urges.

  I crawled onto the bed and kissed her. I could taste her lipstick melding together with and mine. We kissed and caressed each other. Then she backed off.

  “Wait here, my little minx, as I get your special gift.”

  The ecstasy of the passionate make-out session was overwhelming my senses. “Lynessa” slowly took over my mind. Seconds later, Janet returned, but she was wearing a pink strap-on.

  John, what are you doing?! That's a strap-on! She’s gonna—

  The little voice in my head was cut off when she climbed back onto the bed and continued making out with me. By now, “Lynessa” had nearly taken over and I started craving the dildo. Janet rolled onto her back and I moved towards the strap on.

  “Oh, Lynessa, you're such a slut!”

  “Yes I am,” I replied in a girly voice.

  No, no, NO!

  The voice was powerless as I started sucking on Janet’s rubber cock. After giving her a blow job, she pushed me onto my back and slid down my panties. The saliva-coated dildo slid easily up my ass.

  Girlish moans escaped my lips as I stroked my hard cock.

  “Ohhhh yes!” I cried out in an effeminate voice.

  She pushed harder and faster, and soon I was taking the whole thing. The strap-on was double sided, so she was getting pleasured at the same time. I climaxed and shot a load of sperm onto my chest, but she didn’t stop and I came a second time. After what seemed like hours, and several climaxes later, we collapsed from exhaustion. She fell asleep instantly and I passed out only moments later.

  I woke up in the middle of the night thanks to a wet dream about becoming the shemale secretary and lesbian lover of Janet. I shook the ideas out of my head and went back to sleep.

  In the morning, Janet woke me up, ordering me to take a shower and “become a man again.” I did what she told without hesitation. I showered, removed my makeup, and got dressed in my normal clothes.

  After a quiet breakfast, it was time to say goodbye. She paid me what she promised, plus a little extra for “being a good sport,” and promised to delete all the files.

  “You know, I had a ton of fun yesterday and last night,” she said.

  I stood there, lost in my thoughts. “It was… interesting.”

  “Did you not have fun?”

  “Honestly, a part of me thoroughly enjoyed it—dressing up and whatnot.”

  She smiled. “You’re welcome to come by and we can do it again sometime. Besides, I’ll gladly pay you to clean my house. You did an amazing job!”

  I laughed. “Well, if I need the money, maybe I’ll consider it.”

  “We don't have to have sex again… unless you want to.” She winked.

  I walked out the front door and down the path. “I’ll think about it,” I said as I climbed into my car.

  She smiled as I waved goodbye and left.

  THE ROOMMATE

  “Hello?” Jessica held the phone with her shoulder as she flipped through the magazine. She was sitting on the couch in her living room, feet up on the table in front of her, making faces at the heavily-airbrushed photos of bikini-clad women in the newest edition of Sports Illustrated magazine. She didn’t normally read magazines like that, but it was pouring rain outside, and in lieu of anything else to do, she’d begun to read. Three hours later, this magazine was the only piece of “literature” she hadn’t blown through. Honestly, she was grateful for the phone call—now she had an excuse not to keep reading it.

  “Hi, this is Allen,” a man said on the other end. “I called the other day about the room for rent in your condo.”

  Jessica tossed the magazine down on the table and switched her phone to her hand. She sat up straight, changing her demeanor from slacker to professional.

  “Oh yeah,” she said much more attentively. “I remember you. What can I do for you?”

  “I was wondering if there’s a good time for me to come by, either today or tomorrow, to check out the place.”

  She picked up her smartphone off of the table and opened up her calendar app, scanning the dates for a vacancy.

  “Definitely,” she replied after a moment. “How does three-p.m. today sound?”

  There was a long pause on the other end. Then:

  “All right, sounds good. I’ll be there at three.”

  “See you then!” she chirped, hanging up the phone.

  She leaned back onto the couch and set her phone next to her, exhaling slowly as she gazed out the window of their apartment. She had been living there with her friend and roommate, Susan, for almost two years. It was a luxurious three-bedroom, two-bath apartment situated in west Los Angeles within walking distance of the beach. The building had an amazing view of the Pacific Ocean, and as she watched its waves roll lazily toward the shore, she thought about the circumstances that had warranted the phone call she had just received.

/>   Originally, she and Susan had move in with another roommate, Tina, but she had moved to Paris six months ago. For a while, they were able to pay the rent on their own, but as time passed, the financial burden became nearly unbearable, and it was clear that a new roommate was in order.

  After nearly a month of searching, they hadn’t found a single reliable tenant; all who had shown interest eventually backed out for one reason or another. Out of sheer desperation, they had lowered their standards and began opening the vacancy up to male candidates. The man on the phone—Allen—was the first one who actually seemed interested in the room, rather than the two beautiful women that came along with it.

  The sound of Susan emerging from the shower drew her attention to the bathroom door. Susan stepped out wearing a loose t-shirt and sweats with her wet hair draped over the towel around her neck.

  “Who was that on the phone?” she asked her.

  “That was Allen,” Jessica replied. “I've told you about him already… he might become our roommate.”

  Susan’s ocean-blue eyes lit up with recognition. “Oh yeah, him. So, what—is he coming by to check out the place? I’d really like to meet him.”

  Jessica nodded. “He’s coming by around three.” She watched Susan’s face fall.

  “Damn! I’ll be at work.” She pouted. “You’ll have to tell me everything when I get back. And don’t skimp on the details!”

  “Don’t worry,” Jessica replied, hesitantly picking up the magazine she was reading earlier. She exhaled heavily, trying to remember where she left off in the brain-numbing editorial.

  Three-o’-clock eventually rolled around, and Jessica heard a knock at the door. Between the phone call and the appointment, she had showered and changed out of her pajamas and into actual grown-up clothes. She decided to wear something that would cover up most of her body as a test of Allen’s intentions, choosing a loose pair of jeans and a long sleeve shirt covered by one of her favorite hoodie. The once blue sweatshirt had faded into a dull gray from the many washings.

  “Hello!” she greeted as she answered the door. “Wow, you’re right on time.”

  Allen stood in the doorway. He was wearing a t-shirt and jeans, but he didn’t look at all sloppy. His brown hair was nicely-combed, and his face was clean-shaven. He smiled.

  “I thought I would get here a little later, but thankfully, there wasn’t much traffic.”

  She stepped aside and motioned for him to enter, subtly smelling him as he walked by her. No body odor and no trace of pot or cigarettes, she thought. He actually smells good! He waited for her in the entryway as she closed the door behind him.

  “Follow me,” she said, leading him into the kitchen. It was a good-sized space, with granite counter-tops and state-of-the-art stainless steel appliances. The sink was free of any dishes and all the surfaces were clean and spotless, a condition Jessica hoped to keep it in.

  They sat down across from one another at the kitchen table. Jessica ran over the interview questions in her mind.

  “Nice place,” he said, looking around from his seat.

  “I’ll give you the tour when were done.” She clicked her pen. “Tell me about yourself.”

  “Well, I graduated from a four-year degree program majoring in computer science with a minor in environmental science. After that, I got a job with a software developer. The pay was decent, and I was living with another guy in a tiny two-bedroom apartment. He was quiet and kept to himself, but my room was as big as a dorm room. I recently got a major promotion, which included a bigger paycheck, so I decided to move out of that dinky place into something much nicer.”

  Jessica was impressed. “Wow, that's pretty cool,” she said, thinking of the financial stability his promotion could offer them. “Want a tour of the place?”

  Allen smiled. “Sure, I’d love to.”

  The kitchen opened up to the living room. It was decorated with potted plants, art on the walls, and other odds and ends that made the place warm and homey. There were several chairs and a large couch, all facing the big flatscreen TV on the wall.

  The rest of the living room area was comprised of a well-stocked mini bar, a small pool table, and several huge windows with beach views that, when opened, let in a pleasant ocean breeze that could cool the whole apartment. There were magazines and books on the table, and just like the kitchen, the place was clean and spotless.

  Allen approached the entertainment center housing the flatscreen TV and began perusing the DVDs stacked alongside of it. They had some of every genre, but most were action and sci-fi.

  “I really like your movie library,” he said.

  “Yeah, we’re a little nerdy,” Jessica admitted.

  “No worries. I’m a geek myself.”

  She smiled. This guy’s not so bad. He’s definitely not one of those bodybuilder bros that obsess over their bodies, and he hasn’t tried to hit on me, either. So far, so good.

  “This way to the bedrooms,” she said, gesturing to the wall opposite of the TV. There was a narrow hallway with two doors on the left, one at the end, and a large doorway on the right. Sliding wood-panel doors hid whatever was in that room.

  “Okay, on the left side are mine and Susan’s rooms.” She opened one of the doors. “This one is mine, and Susan’s is on the far end. We also share a bathroom.”

  She closed the door and they walked down to the end of the hall.

  “This,” she said as she opened the door, “will be your room—should you decide to move in, anyway.”

  The bedroom was L-shaped with a bathroom at the very end. It was a good size; not big, but not too small, either, and perfect for just one person. It had a shower/bath combo, an ‘industrial strength’ toilet, a porcelain sink above a large, wooden cabinet, and a mirror with vanity lighting.

  “Wow, this is nice.” Allen said, looking around.

  “It differs from mine and Susan's, but you get your own bathroom. Also, because we’re at the corner of the building, you also get a nice view of the ocean.”

  She opened the window and the two of them looked out at the blue Pacific. It was a sunny day and the breeze was refreshing.

  “It’s definitely bigger than my current bathroom, and a lot nicer, too,” Allen said. “And that’s certainly a view that can’t be beat.”

  Jessica smiled. She couldn’t believe things were going so well.

  They left the room, and as they were walking back towards the kitchen to finish up the tour, Allen noticed the large wood-panel doors. “What's in this room here?”

  “Ah,” Jessica said, sliding one of the large panels aside. “This is the laundry room.”

  The room was bare, except for the high-end washer and dryer, several empty laundry baskets, and a rod with a bunch of empty hangers.

  “You should see what it looks like on laundry day,” she said with a smile. “I’m a clean freak. You probably noticed the kitchen. But when it comes to clothes, I can’t stand seeing a full hamper.”

  She closed the door and they walked back to the kitchen, sitting down again at the table.

  “What do you think?” she asked him, opening a can of soda.

  Allen beamed as he meandered around the kitchen. “I love it!”

  She took a long sip of the soda, her mind already envisioning life with Allen in the apartment. “Awesome, just what I wanted to hear. I’ll send you over all the necessary paperwork and you can move in whenever you’re ready—just be sure to give me a call ahead of time so I can put it on my calendar.”

  Allen was so excited, he didn’t know what to do with his hands. He crossed them in front of him only to put them in his pockets seconds later. “Will do.”

  They stood up, shook hands, and Allen left, excited about the new place.

  Three uneventful months went by, and Allen, Jessica, and Susan were getting along quite nicely. The girls were both glad he wasn’t trying to hit on them every hour of the day, and Allen proved to be courteous and respectful, often offering to do dishe
s or other chores. Jessica turned him down every time, mainly because she liked cleaning the place herself. Even so, he still offered every now and then.

  He was quiet kept to himself in his room, but he wasn’t a shut-in. He was social and went out with his friends every weekend and joined the two women every time they had a movie night.

  Everything was going great—until one fateful laundry day.

  Damn, I really need to take a shower, Allen thought that morning, smelling himself as he got out of bed. He stood up and stretched, staring out of the large window at the ocean. I love lazy Saturdays.

  He stripped off all his clothes and threw them at his hamper, which nearly toppled at the weight of the clothes pile. I guess it’s about time I do my laundry, he thought to himself. I’m surprised it isn’t overflowing.

  After toweling off, Allen returned to his bedroom to get dressed.

  “Ah, nuts. Looks like I'm out of clean underwear,” he said, staring at his empty drawer. “Looks like I’ll just wear a dirty pair from… what the—?”

  He walked over to his hamper only to find it empty. Completely empty. Looking around, he found a sticky note on the wall next to the hamper. It had Jessica’s handwriting on it.

  Allen:

  I'm sorry, but when I came in to say that Susan and I were leaving, I noticed the state of your hamper, and well, I couldn’t control myself :)

  Your clothes are getting washed and will hopefully be done when you get out. By the way, Susan and I are both gonna be gone until late tonight, so do what you please, but don’t make a mess of the place!

  - Jessica

  “Balls.”

  He walked out of the room, still wearing nothing but the towel, and headed into the laundry room. He hoped that she was right about the timing.

  When he slid open the large wooden door, he heard the sounds of the machines working. He looked at the washer and noticed it still had 30 minutes left, and the dryer showed the same.