Lipstick & Miniskirts

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Lipstick & Miniskirts Page 2

by John Dylena

The woman turned her gaze back to Jacob and grinned.

  “She returned to the parking lot, where her ride was. It was a limo, and waiting for her in the backseat was a man she’d just met at a club earlier that night. They fucked on the way to another club. She was once a man who sat behind his computer all day and hated on women. He called them shallow, two-faced, and all kinds of names. Blamed them for his loneliness. Who would’ve thought that the moment he became a woman, he’d be all the things he hated?”

  The reflection giggled, then laughed. It was a laugh of the popular girl in high school or the manipulative sorority president who always got whatever she wanted.

  “What do you want from me?” Jacob asked, the sudden fear causing his new girl voice to tremble.

  The reflection stopped laughing and climbed back down from the counter. “Do not fear, Jacob. I only punish the naughty boys. The fat woman-hating neckbeard will be given a choice: return to his old self and fix his ways, or remain a cock-hungry slut for the rest of his—her—life. He has no influence over his actions; he’s merely a passenger in that body. You, on the other hand, have been a good boy. And good boys get rewards.”

  Jacob’s body suddenly moved on its own accord. The woman in the reflection put her hands on the counter and leaned forward, and Jacob did the same. She arched her back and pressed her chest forward, her large breasts straining the fabric of the shirt. She leaned closer, bringing him closer to the mirror.

  “I know what it is you desire, Jacob. I know who it is you desire. I know what you search for on your computer late at night and what you dream about in your sleep. I know you’re a shy, scared little man who’s afraid to put himself out there. I’m giving you a chance.”

  He was only an inch or so from the mirror. He could feel the heat radiating off of his body. He could smell the intoxicating perfume of his drenched sex.

  The woman smiled. “She’s there now. Waiting. Alone. You know who. You know where. The night is young and tonight is the only chance I’ll give you. You have until dawn. I have provided you with all that you need. Good luck, Jacqueline.”

  Jacob—now Jacqueline—regained control over her body. She slumped forward, almost hitting her head on her mirror before straightening and taking a couple deep breaths. That’s when she noticed the mark on her mirror: someone wearing an identical shade of lipstick as her had kissed the mirror. Written above the lip print in what also looked like lipstick was a name: Melissa. There was even a little heart drawn next to it.

  She knew in the back of her mind who the mysterious woman was referring to in her vague, quest-giver tone. Melissa lived on the floor above Jacob. They used the same grocery store and had bumped into each other at random times, once even at the laundromat. She was a very attractive woman, not to mention smart, clever, and a fellow geek. They’d have small talk and occasionally chat about video games; they were friends on some gaming sites, too.

  He had asked her out once and she had declined, saying that she was a lesbian. At first Jacob had thought Melissa was just saying that because she didn’t find him attractive and wanted to find some way of declining his offer without hurting his feelings. While he was bummed, Jacob tried not to let it get to him too much since she was still a great friend.

  Maybe that’s where I got it right, Jacqueline thought.

  Jacob eventually found out Melissa was telling the truth about being a lesbian. He found out in the most unexpected way. Jacob was a fan of BDSM, but his favorite thing above all others was lesbian BDSM. He’d been a member of an online fetish community since before he had befriended Melissa, only he barely ever frequented it since he was a shy, socially awkward guy. It was hard enough meeting women in the vanilla sense; throwing kink into the mix made it feel almost impossible.

  After reading a rather thrilling erotic short story one night, he logged back into his account and browsed around the local scene. There was a dungeon relatively close by that he’d gone to once and stayed at for an hour before wussing out. While looking through the threads, one particular profile picture caught his eye and when he opened up the profile, he discovered that it belonged to Melissa. She listed herself as single, and a lesbian, and some of her pictures verified it.

  That night, Jacob shamelessly masturbated to Melissa’s photos of her topping other women, after which he swore to never do so again. Talking with her became awkward after that. He had thought about how to bring up their mutual interest many times, but he never went through with it. He could never bring himself to attend a party at the dungeon she would go to in fear of giving off a stalker vibe.

  “I can’t fucking believe this,” Jacqueline said, her voice still foreign in her ears. She looked up and tentatively stared at her reflection. The ceiling light reflected off of her glossy lipstick and the shiny gold jewelry that she wore. The woman had given her a chance to be with Melissa. All she had to do was muster some courage. She knew there was a play party tonight, as the dungeon had it on the same night every month.

  “It’d be a lot easier to go outside if I didn’t look like a porn star,” she muttered. Then she remembered what the woman had said: I have provided all that you need. “What did she mean by that?”

  She exited her bathroom and stopped when she saw what awaited her on her kitchen table. A large square shoebox and a rectangular department store box innocently sat there, and a long, black coat hung from a clothes hanger hooked over one of the cabinet door handles.

  Jacqueline opened the square box first. Inside was a pair of thigh high, shiny black boots, complete with platforms and what looked like a six-inch heel. “Fuck me,” she said as she grabbed one for a closer look. The gleaming latex would probably cling to her like a second skin and just screamed for someone to bend her over and take her.

  She returned the boot to its box and opened the next one. “Oh, you’ve got to be shitting me.” Jacqueline pulled a shiny black dress with fishnet sleeves out and held it in front of her. There was more fishnet then solid fabric. To say that it was a revealing outfit would be a massive understatement. Now I know what the coat was for, she thought.

  She walked from the table to her kitchen counter, where a small black purse rested. Inside she found her wallet with a new ID. All of her credit and debit cards had “Jacqueline” instead of “Jacob”, and the mystery woman had even thrown in some extra cash. The remaining contents of the purse consisted of some emergency makeup, a few condoms, gum, and her car keys. She frowned when she realized that they were the same keys she’d had when she was a man. Not that there was anything wrong with her car; she was just hoping to find the keys to a Ferrari or something.

  She glanced up at the clock. Only thirty minutes remained until the party’s doors closed and no one else was let in. Her gaze returned to the kitchen table and the clothes. “Time to get dressed, I guess.”

  “I look fucking ridiculous,” Jacqueline said when she surveyed herself in her bedroom’s full-length mirror. Forget the fact that she could somehow effortlessly walk in platform high heeled boots despite having never worn such a thing before, but the dress could barely even be considered a dress. The hem reached her upper thigh and when she bent over it showed the bottom of her ass. The stretchy fabric clung to her body and left practically nothing to the imagination. Fishnets exposed most of her full cleavage and midriff, the neckline dropping down below her belly button. Barely a quarter of her breasts were covered by the solid black fabric, including her nipples. The back of the dress was almost entirely fishnet, exposing the waistband of the hot pink thong that had started this whole mess.

  Jacqueline wrapped the coat around her, which covered her entire body from her wrists down to her ankles, and grabbed her purse. She paused just in front of the door to her apartment as fear and anxiety welled up inside.

  “You can do this. You know the way to the dungeon. It’s a short drive down the street. It’s got a private parking lot and everything.” Slender fingertips adorned with hot pink polish reached out and gripped the doorknob
. “Walking down to the car will be the hardest part of all of this.”

  Taking a deep breath, she opened the door and stepped out into the hallway of her complex, making a bee line straight for the elevator and jabbing the button like a kid on a sugar rush until the doors closed and she was alone. Her relief was only momentary as she only made it two floors down before the doors opened again and three guys entered. Jacqueline could smell the alcohol on their breath and felt the weight of their lustful stares.

  The elevator ride seemed to slow to a crawl, but thankfully the men got off on another floor. Jacqueline let out a heavy sigh and arrived at the parking garage without any further excitement. Her car waited for her where she had left it.

  Just as she was able to flawlessly walk in high heels, Jacqueline was also able to easily drive in high heels, a fact which didn’t cross her mind until she was already halfway to the club. She arrived there with fifteen minutes to spare until the doors closed, and as she approached the front door, she wondered if the mysterious woman had also RSVP’d for her as well.

  The woman at the front desk smiled as she checked Jacqueline’s name off of a list and accepted the money for her entry fee. “You can check in your coat on the other side of the door.”

  Jacqueline nervously slipped out of her outer garment. Even though a woman stood completely naked not four feet from her, she felt very much exposed. She exchanged her coat for a ticket from the smiling man at the coat check before awkwardly navigating her way toward the social area, passing by rooms where men and women were spanking, whipping, flogging, paddling, teasing, and doing all sorts of fun, kinky stuff to each other.

  The kitchen was empty of people, but not of food. A table and the countertops were covered in an assortment of finger foods, from healthy stuff like veggies to straight up junk food. Next to the kitchen was the social area, filled with round standing tables, couches, and a small bar with a counter. Not yet feeling up to socializing, Jacqueline browsed the selection of foodstuffs before carefully plucking a thick, chocolatey brownie from a stack of its kin with manicured fingers.

  She’d just lifted it to her mouth when she heard Melissa’s voice.

  Jacqueline stopped mid-bite and her jaw dropped. She spotted Melissa through the doorway, hanging out by one of the tables and chatting with an older woman. Melissa had her brown hair pulled back into a messy ponytail and wore a shiny black corset that showcased the curves of her bare breasts under a fishnet top. Jacqueline had seen pictures of Melissa topless when she had first stumbled upon her fetish profile, but she’d never actually seen her topless in real life. She quickly turned away so that Melissa wouldn’t catch her gaping.

  “Have we met before?”

  Jacqueline turned toward the male voice and choked on her brownie when she saw one of her coworkers standing there. His name was Andrew. He was short and wide, with a thick beard and a buzzed head. He had started working at the company before Jacqueline—Jacob—did, which was about six years ago. Andrew was a quiet but helpful man. He was also married, and his wife, who was a foot taller than he was, walked up behind him. He was shirtless and wearing a collar; she was dressed in a domme outfit holding a metal leash that clipped to his collar.

  “Oh shit, are you okay? Need some water?” Andrew said.

  “No, no, I’m fine,” Jacqueline replied, swallowing the brownie. “Just went down the wrong way.”

  “I’m Lady Diane, but you can just call me Diane,” Andrew’s wife said, extending her hand. “The man-child is my husband, and my submissive.”

  “Yes, sorry,” Andrew said, extending his hand. “My name’s Andrew.”

  “Jacqueline,” Jacqueline said, shaking both their hands. “And no, we’ve never met. This is my first time here.” She actually had met his wife several times over the years that Jacob and Andrew had worked together. Diane was a strong, proud woman. Confident, but not smug and arrogant. It didn’t surprise Jacqueline that she was the one wearing the pants in their relationship.

  “Welcome, welcome!” Diane said. “It’s always a pleasure meeting newcomers. Please, feel free to ask me any questions you have.”

  “I will,” Jacqueline said before the couple returned to browsing the food.

  “Now that is a sexy outfit.”

  Jacqueline froze when she heard Melissa’s voice. She took a deep breath and slowly turned around, just about fainting when she got her first full look at Melissa. Moments before she could only see her from the waist up, but now Jacqueline could see that below the corset was a leather miniskirt, stockings, and black, round-toed high heels. Tasteful dark makeup accentuated her eyes and left her features even more alluring. If she’d still had her cock, it would be full on erect at the sight.

  “I heard that you’re new. My name is Melissa,” she smiled.

  Jacqueline stuttered out a reply. “My name’s Jacqueline, pleased to meet you.”

  “I love your outfit,” Melissa said, walking around her. “It’s so sexy. I love the fishnets. Where did you get it?”

  “Online,” Jacqueline said, trying to hide her embarrassment.

  “Are you here with anyone? Or did you come by yourself?”

  “I came alone. I really like your outfit, by the way. You’re very pretty.”

  Melissa smiled. “Thank you! Do you have anything set up?”

  “What do you mean?”

  There was a loud smack, and a woman’s voice brimming with pained ecstasy echoed through the kitchen.

  “Oh,” Jacqueline said. “No, I don’t.”

  Melissa laughed. “Me neither. Though if you want, I know of a quiet corner we can sit in and just chat. I’m sure you’re very nervous and with it being your first time, I’ll bet that this is all a little overwhelming.”

  “I’d really like that,” Jacqueline replied. She smiled and felt her cheeks grow warm. Melissa caught her lower lip between her teeth and returned the smile.

  Then she stuck out her hand. “Come with me.”

  Jacqueline felt like she was in a dream. The world around her seemed to slow down and turn hazy as Melissa led her through the dungeon with the sounds of kink welling up all around them. She heard moans and cries and even bouts of laugher. She heard the crackle of electricity as she passed by a woman tied to a St. Andrew’s Cross with her dom dragging a violet wand across her flesh. They exited the main room into a narrow hallway and the sounds became more distant.

  The hallway led to an open room with couches and chairs. It was mostly empty except for a woman on her cellphone and a couple chatting between themselves in excited whispers. Melissa sat down on a couch and Jacqueline sat down next to her.

  “So,” Melissa said after several moments of awkward silence, “this is your first time?”

  “Yeah,” Jacqueline replied. “First time.”

  “Tell me about yourself! I always enjoy meeting with and getting to know the noobs. When I came here for the first time, a woman sat down with me and took the time to get to know me. She made me feel welcome and has since been my mentor.”

  “That’s very cool. Makes me feel more comfortable. I’m so nervous!”

  “I understand. Though I’m surprised you came here dressed in that. For my first time, I wore jeans and a long-sleeved shirt!” She laughed.

  “I, uh, wanted to look good,” Jacqueline replied. “To be honest, I’ve wanted to wear something like this for a long time.”

  “Ha! I like your honesty. So, what brought you here tonight?”

  Jacqueline bit her lip and looked away. She couldn’t tell Melissa that she was actually her guy-friend Jacob, only that a mysterious woman had turned him into a smoking hot chick so that she could have a chance to live out a fantasy.

  “Well, I first discovered it in a book.” That part was mostly true. Jacob had found his way into the world of BDSM through the internet and porn. But it was when he read an erotic short story about a woman falling in love with another woman and experiencing BDSM through her new partner that Jacob discovered hi
s fetish for lesbian BDSM.

  “It wasn’t 50 Shades, was it?” Melissa scowled.

  Jacqueline laughed. “No, no. It was some short story on one of those free erotica websites. I can’t remember what it was called.”

  “Oh? What was it about?”

  “It was…” Jacqueline nervously shifted in her seat and looked away from Melissa.

  “It’s okay. Remember, we’re all perverts here. No kink-shaming, I promise.” Melissa said with a smile and a wink.

  Jacqueline took a deep breath. Here goes nothing. “It was about lesbian BDSM.”

  Melissa’s eyes lit up with interest and something a little hungry at her words. She leaned forward slightly. “I see. If I may, how do you see yourself in this lovely, kinky world? Have you ever played with anyone before? I know this is your first time here, but have you been to another dungeon or just played with a boyfriend?”

  Boyfriend. That was a strange word to hear directed at her.

  “No. No boyfriend. Never played with anyone before and this is my first ever dungeon visit. What about you?”

  Melissa smiled. “Well, I’ve been coming to this place regularly since I first moved here. I discovered kink back in college, when I dated a guy who introduced me to the scene. I liked it, but we weren’t together long. I learned two things in that relationship.”

  “What two things?”

  “That I wasn’t attracted to men,” Melissa leaned in closer, “and that I was a top, not a bottom.”

  Jacqueline’s heartbeat skyrocketed as though she’d spontaneously decided to run a marathon, and her mouth went dry as sweat started to dampen her skin. She had never seen this side of Melissa before. She was so… seductive. She had always seemed so casual and laid back, even withdrawn sometimes. She never talked much about her personal life with Jacob; it was always about their interests in music, movies, and video games.

  Something must have shown in her face, as Melissa straightened and her demeanor changed instantly. “I apologize. I didn’t realize I was making you so nervous. If I’ve overstepped my bounds, please tell me. The last thing I want to do is come off as some sort of a creepy predator. Sorry!”

 

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