Lipstick & Miniskirts

by John Dylena

  “I was wondering why some of my makeup was out of place, as well as a couple pieces of my jewelry.” Leah took a step forward and put her finger on his chest. Her nails were long and sharp, their surfaces polished and painted the same color red as her lipstick. “I thought at first it was my fault, that I had put them back that way and just forgot about it.”

  She circled around him as she spoke, her fingernail trailing across his chest to his shoulder.

  “But that never happens, and I was left with only one other option: that Lee did something with it. I thought about what he would use it for. Lee never showed any sign of wanting to wear it himself—believe me, I would know if he did.”

  Leah stood behind Brian and put her hands on his shoulders.

  “Did you know he’s cheated on me? Twice in the past week, both times with some drunk slut he bumped into at a party. I even walked in on them one of those times, but Lee didn’t remember it. His memory has been pretty shoddy lately, even forgetting my name when we had sex last.”

  Her hands left his shoulders and traveled down the length of his back until they got to his hips and the hem of his dress.

  She pressed her breasts against his back and brought her lips to his ear as she wrapped her arms around his stomach. “So tell me, Brian—you didn’t just clean the apartment wearing this adorable outfit, did you?”

  Oh god, she knows. How? How could she know what I did with Lee? He didn’t tell her, did he?

  “N-No, I… just cleaned.” For the first time since Leah walked into the apartment, Brian’s throat eased up just enough to allow him to speak. He was stumbling over the words, hoping, praying that she was just teasing him.

  Leah moved her lips to his other ear as her hands slid further down his front.

  “Is that so?”

  “Yes. It’s true.” Brian’s heart pounded. His breaths were quick and shallow.

  “In this day and age, maids that wear that outfit rarely ‘just clean.’ You don’t have to lie to me, Brian. You can tell me everything.”

  He could feel her hot breath on his neck. It made the hairs on his nape stand straight up. Goosebumps covered his body and he squirmed under her touch. She lifted her leg and brushed it against his, her stockings grazing his own as her hands traveled up the front of his body and grabbed his flat chest.

  “Don’t be afraid. Tell me your deepest, darkest secrets.” Her voice was low and sultry as she purred into his ear.

  It was too much. He was powerless against her.

  “You’re right. I… didn’t just clean the apartment.”

  “Oh, you naughty boy,” she said as she lifted up the front of his skirt. “Tell me what you did.”

  Brian closed his eyes and gasped as Leah’s hand caressed his balls through his lace panties.

  “Lee… he took pictures of me… used them as leverage.”

  “And?”

  “When I finished cleaning, I… got down on my knees in front of him.”

  “Like a good, obedient maid?” she said as her fondling continued.

  “Y-Y-Yes…”

  Leah pulled down the front of Brian’s panties and gently squeezed his swollen cock. “Go on,” she said as she slowly stroked.

  “I… uh… unzipped his pants, and I… ooh!”

  “You what, Brian? What did Lee’s obedient maid do for him?”

  Leah stroked harder, faster as she breathed into his ear, moaning quietly, reveling at how much his body writhed under her touch.

  “I… I…”

  “Tell me, Brian!”

  “I sucked Lee’s cock!”

  He said it. The words came out of his mouth. The one person who he was most afraid of finding out knew about his secret act with his roommate, something he would never forget, and that forever changed him.

  Despite his revelation, Leah continued to stroke his dick. She would bring him to the edge and slow down, and as if she would read it on his face, she would then start stroking him again once he came down.

  “But that’s not all you did, is it? You went further, didn’t you? How far did the obedient, submissive little slave girl go for her master?”

  “No…” Brian lurched forward as legs gave out. Leah supported him, easing him down onto his knees. He fell back onto her and she whispered softly into his ear as she continued to jerk him off.

  “Tell me, Brian.”

  Leah didn’t slow down this time.

  “I got onto my hands and knees on the couc,h and he… he… he fucked my ass!”

  Brian’s body shook violently as cum exploded out of his cock onto the living room floor. He moaned as Leah milked him until his dick turned flaccid in her hand.

  “Good girl,” Leah purred. She lifted her hand up and frowned. Strands of Brian’s cum clung to her hand. “Say, Brian…”

  “Yes?” hHe said breathlessly.

  “Did Lee give you a name?”

  “He did, it was… Brianna.”

  “I like that name. Now, Brianna, you’ve gone and made a mess, and I need you to clean it up.”

  Leah held her hand in front of Brian’s face, and he spotted the strings of sticky cum on her long, slender fingers. She moved her hand close to him.

  “Well? Clean up after yourself, Brianna. I don’t have all day.” She brought her hand up to his mouth and pressed her finger against his lips, smearing the cum.

  “Be a good girl now, Brianna.”

  Brian groaned as he slowly opened his mouth and Leah slid her finger inside. He grimaced as he sucked the cum off of her, and when her finger was clean, he stuck his tongue out and licked the remaining clumps.

  “That wasn’t so bad now, was it?” Leah backed away from Brian and got back onto her feet. She reached down and helped Brian up.

  “Look, Leah, about all this—”

  “Hush. You don’t have to worry. It’ll be our little secret.”

  “If you don’t mind me asking, why were you here?”

  “To confront Lee about him cheating on me and to break up with him. He’s been avoiding my calls and texts, so I was hoping to catch him before he left.”

  Leah sighed as she plopped down on the couch.

  “I was so angry, so furious with him that I could’ve torn his head off. But now? Now I feel so much better.”

  “Oh,” Brian said, looking back at his bedroom door. “If you don’t mind, then, I’m going to get changed.”

  “Who said you could get changed?” Leah answered, looking up at him with a grin on her face. “I didn’t recall giving you that order. But yes, why don’t you get changed? Put some regular clothes on, then grab your wig. We’re going back to my place.”

  Brian’s jaw dropped. “Wait, what?”

  Leah stood up and stretched. “You heard me. We’re going back to my place. Actually, we’ll be making some stops first, and then we’ll be going back to my place.”

  “But—”

  “No buts, Brian. This is a side of you I’d never thought I’d see.” She moved in front of him and placed her lips by his ear, whispering. “And you know what? It really turns me on.”

  She planted a kiss on his cheek, and he stood dumbfounded as he watched her walk toward the front door.

  “You have five minutes. If you’re not standing beside me before then, I’m walking out this door, and not only will this opportunity pass you by, but you’ll never see me again.”

  Leah lifted her wrist up in front of her and looked at her watch. “Five minutes, starting now!”

  It took a moment for Brian to realize what was going on. He had a chance, an opportunity to experience something he never thought he’d want to experience. Not only that, but he finally had the chance to be with Leah.

  Leah, the drop dead gorgeous woman who not only didn’t scream, freak out or run away when she caught him jerking off in the living room while cross-dressing, but embraced it and took him to the edge and beyond.

  Now she was giving him the chance to go even further with her. Not with Lee, his
drunken, self destructive roommate—it would be with her, the woman he’d always wanted to be with.

  “Four minutes.”

  Brian said nothing as he turned and ran into his bedroom. He didn’t even bother closing the door as he quickly peeled off the dress and tossed it onto his bed. He slid off of the panties, kicked his heels off and removed his stockings.

  “Bring the heels. I like the heels,” Leah shouted from the other side of the apartment.

  Brian set the wig onto the bed and got dressed, grabbing the first pair of boxers, jeans, and a t-shirt he could find.

  “Two minutes.”

  What happened to three minutes?!

  He slipped into some socks and shoes, grabbed his wig and heels and ran out into the living room and next to Leah. He doubled over, gasping for air, blonde wig in one hand, red heels in the other.

  “You made the right choice, Brian. Are you ready to go?”

  “I am.”

  “From now on, you are to address me correctly. Which will be Mistress. Understand?”

  “Yes… Mistress!” Brian threw the title in there at the last moment.

  Leah smirked before opening the door to the apartment. “Shall we?”

  Brian smiled as he stepped through the door. Leah closed and locked it behind them, and he followed her out of the complex to her car. Fortunately, no one saw them.

  They climbed into her luxury coupe and sped off.

  “So, Mistress, where are we going?”

  Leah said nothing as she turned to him and winked. She turned the volume up on the radio, blasting the music as she drove.

  Brian’s cheeks turned bright red as she pulled into the parking lot and parked directly in front of the sex toy shop. He looked out at the mannequins in the display windows and the wide array of sexy lingerie they wore.

  “Stay in the car. What I’m getting is a surprise.”

  Brian nodded and watched as she disappeared inside the store. It left him wondering what she was getting for him. It could have been any number of things, from bondage gear to sex toys, maybe even costume.

  He shifted on the leather chair and looked away from the storefront to the heels in his hands. Taking them in, he couldn’t help but smile. Minutes later, Leah emerged from the store carrying several black shopping bags.

  Brian tried to peek into them as she walked past his door, but he saw nothing but tissue paper and frowned as she opened the trunk and stashed his presents. Leah grinned as she slid into the driver’s seat, then followed Brian’s gaze to her skirt, which had slid up higher onto her thighs and showed off the tops of her stockings.

  The car engine roared to life and she drove off, music blaring as they arrived at the parking structure for her condo. Leah made Brian carry the bags from the car to her condo, occasionally looking back at him over her shoulder and smiling.

  As much as he wanted to peek into the bags in his hands, there was no way he could tear his eyes off of the figure in front of him. Leah walked so gracefully in her stiletto heels, and his eyes followed the seams of her stockings up to her perfect ass. It swayed back and forth hypnotically as she strode with confidence.

  It was when they stopped in front of her door that Brian realized he had never actually been to her place. In fact, the only times he ever saw Leah was when she came to the apartment with Lee, either for one of his many parties or when they returned from a date. Lee had mentioned occasionally how successful Leah was and how she had a nice place.

  “Holy crap, this place is awesome!”

  “Hard work has its rewards,” Leah said as she walked in after him. “Follow me, Brian, it’s time we begin.”

  He followed her through the living room, into the hallway, and finally into the master bedroom. Her home was well furnished and cozy, not to mention remarkably clean.

  No wonder she had me leave the maid outfit at my place. There’s nothing for me to clean here!

  Her bedroom, despite being much larger than his own, was modestly decorated in comparison to the rest of the condo. Leah had nothing more than a queen-sized bed, a long wooden dresser, a bookshelf filled to the brim and a small writing desk.

  On one of the walls was the entrance to her walk-in closet. Brian stood in the center of her bedroom and watched as Leah slid open the white shutter doors and closed them behind her.

  “Brian,” she said before closing them all the way, “while I am getting changed, I want you to hop into my shower and shave. I take it you had to shave for your day as a maid?”

  “I did, Mistress,” he said with a nod.

  “Good, then shaving again shouldn’t be difficult. Just be sure you’re thorough. Don’t want my little pet to be all hairy, now, do I?” She closed the doors to her closet and Brian walked away from the bags of goods she’d bought for him.

  Her bathroom was sleek and ornate, with granite counter tops and cream-colored appliances. Leah had a bathtub with silver faucets and an all glass shower. There was a low vanity table with all kinds of makeup neatly organized on the smooth white surface.

  Brian frowned. No wonder she’d found out that Lee borrowed her makeup. Brian’s roommate never put anything back the way he found it—if he even returned it at all.

  “I don’t hear any water running in there!”

  “Sorry, Mistress!” Brian quickly stepped into the shower and fumbled with the knobs until hot water poured down on him from the showerhead. The process was quick, and once Brian was all clean-shaven, he returned to the bedroom with the towel around his waist.

  Leah was waiting for him there. She sat on the edge of her bed, her legs crossed and her eyes trained on the bathroom door. She grinned as she watched him walk into the room and Brian turned bright red as she stood up.

  She had changed out of her rather sensual work attire into something just plain sensual. She wore a black fishnet dress, her perfect breasts and pink nipples visible through the sheer fabric, and thigh-high black leather boots. He could see her thong, a garment of crimson and lace that just barely covered her ripe cunt.

  Leah turned and walked off to the side, revealing the items laid out across her bed. “Come here, Brian. Let me show you the fun we’ll be having today.”

  He swallowed hard as he stood next to her, his eyes scanning the surface of her comforter and the items carefully laid across it. Everything he imagined she would buy for him—both out of excitement and fear—was there on the bed.

  One thing was missing, and it was the item in her hand.

  “Got to take care of this first,” she said, pulling off his towel. Brian’s eyes went wide as she turned and knelt down in front of him. She produced a clear chastity cage, and before he could open his mouth to protest, Leah gently eased his balls through the ring and attached the front. There was a quiet click as she locked it in place with a padlock. She stood up.

  “Consider this your punishment for cumming all over my hand this morning.” She reached down and picked up the gold chain on the bed and wore it like a necklace. “These are the keys to your freedom, Brian. They shall remain in my possession until you have earned them. Understood?”

  “Yes, Mistress.”

  Leah smiled. “Good. Back to the demonstration.” She turned toward the bed and pointed out the various items. “I got you a collar, inflatable plug, a vibrator, suction cup dildo, restraints, and other bondage gear, as well as that cage that you’re wearing.”

  “Oh… wow.”

  “Something wrong, Brian?”

  “No, nothing’s wrong, Mistress. It’s just… I’m a little overwhelmed.”

  “Yes, that’s understandable. It’s a new strange world you’re being introduced to, so hesitation and fear is justified.” Leah moved between him and the bed. She smiled as she placed her hand on his cheek.

  “Brian, we don’t have to do this if you don’t want to. I’m not forcing you to do anything here. It’s just… I’ve never had anyone to play with. Lee isn’t into this sort of thing, and any boyfriend I’ve had in the past w
as scared off when I brought it up.”

  “Leah…” Brian said as he grabbed her hand. “I’d be glad to do this with you. I mean, sure I’m nervous about all of it, but I want you to be able to enjoy yourself. You did buy all these things for me. I don’t want them to go to waste.”

  “Oh, you’re so sweet,” she said, kissing him on the cheek. “Now, bend over for me.” She smiled as she placed her hand on Brian’s back.

  “Of course, Mistress,” he said as he leaned forward and placed his hands on the bed. He watched her over his shoulder as she stared at his ass and smiled. She moved her hands over it, squeezing and playing with his cheeks as her thumb glided over his asshole.

  “You have such a pretty ass, Brian, so smooth and delicate. Lee never let me shave him. He also never let me top him. I always had to be on the bottom, letting him control what happened in the bedroom. It’s not that he was a Dom; no, he just felt that the man should be in charge. The woman should only be there for his pleasure.”

  She playfully slapped his ass and gigged.

  “Even if he had remained faithful to me, I doubt I could have been with him for another month. The key to any relationship is compatibility, whether it’s intellectual, emotional, political, or sexual. If there is no compatibility, then the relationship is doomed to fail. You can’t put a square peg in a round hole, and two dominant—or even submissive—people won’t make a stable, healthy relationship.”

  Brian remained silent as she spoke. She walked away from him, her hand lingering on his ass until she moved out of reach and it fell to her side. Leah continued talking as she rounded the bed and reached for the inflatable plug, her eyes looking over it curiously as she squeezed the ball, filling the black rubber cock with air.

  He could feel his cheeks turn red as he watched it grow larger and larger in her hands. It grew long and thick, bigger than his own and even bigger than Lee’s. There was no way that would fit inside of him. Leah let the air out of it and it returned to its original, much more tolerable size.

  “I stuck with Lee for so long because I thought he would grow more open to the idea of letting me take control. There were a couple times where I tried to warm him up to the idea, but he was dead set in his ways. We grew apart and he cheated on me. He probably wanted to sleep with a girl wouldn’t resist him, who would get on her knees and suck him when he asked her to. A woman like Brianna.”