Lipstick & Miniskirts

by John Dylena

  Will I even wear these again? I mean, I do like them and they’re really sexy. Brian shook the thought from his head. No. Even if he did end up keeping them, there was no way he’d ever wear them again. This is for today only.

  He looked out into the living room as the eggs and bacon cooked. Lee paid no attention to him. His eyes were half-open and focused on the TV. Brian sighed as he finished cooking breakfast.

  “Master Lee, breakfast is ready,” he called out to him as he poured the coffee.

  Lee smiled as he walked past Brian and sat down at the table. “I could get used to this. I wonder if I could get Leah to do this for me. Better yet, I should find a way to make both of you my pretty little maids.”

  Brian said nothing as he set the plate and mug down in front of Lee in between the last clean fork and knife. He looked back at the dirty dishes stacked high in the sink and frowned. His work was cut out for him.

  “Where are you going?”

  “To make myself something to eat.”

  “Not until I am finished. You must stand by me and wait patiently. I might need something.”

  Brian quietly sighed. “Yes, Master Lee.”

  Lee looked up at him and smiled smugly, his mouth full of food and some yolk on his chin. Brian pointed it out to him, and Lee handed him his napkin.

  “Wipe it off for me.”

  Brian hesitated. He shot Lee a glare.

  “Don’t make me say it again.”

  Grumbling, he took the napkin from him and wiped the yolk off of his chin. Then he handed the napkin back.

  “I am finished. Brianna, that was a delicious breakfast. You may now eat and begin your chores.”

  As if you needed to tell me tha—

  Brian’s thought was interrupted by a slap on the ass. His face turned bright red and he watched Lee laugh as he walked out of the kitchen. He looked down at his dress and squirmed as he felt his cock harden a little bit from the rude and strangely arousing gesture.

  With his own hunger quickly dealt with, Brian pulled on a pair of bright yellow rubber gloves and scrubbed away. He quietly hummed to himself as he tackled the mountain of dishes, scrubbing them clean and filling the dishwasher to the brim.

  But it was just the first on a long list.

  Brian moved about the apartment, dusting, vacuuming, scrubbing, mopping, stopping only to empty the dishwasher and reload it with the second wave of dishes. Lee occasionally barked an order at him, from handing him the remote to scratching his back, to getting him drink after drink. Brian answered each command with a curtsy and a “yes, Master Lee.”

  His stomach rumbled as lunch arrived and Lee saw fit to task him with making the most over-the-top sandwich. Brian delivered the supposedly tasty sandwich to his roommate, who hadn’t left the couch all day.

  “Another beer, Brianna,” he said, taking a bite of the sandwich.

  “Yes, Master Lee.”

  It had become instinct now. Brian didn’t have to think about his reply. It along with the curtsy and his feminine voice came naturally. His semi-erect cock twitched in his panties at the thought of it. He was walking naturally in the heels, his hips swaying with each step. His legs weren’t the least bit tired or sore. He could spend the rest of the day, or even the evening in them.

  “Hurry that cute ass up,” Lee shouted, “I’m thirsty!”

  Brian froze and looked back at Lee over his shoulder. Lee remembers I’m a guy, right? That I’m not actually a woman? Then he remembered the two beer bottles that he had already thrown away and the third he was retrieving.

  He removed the bottle from the fridge, opened it and walked over toward the couch. Brian held the bottle out for Lee to grab it, but his roommate made him bend closer and closer to get it.

  Brian yelped as Lee both grabbed the bottle and his waist, then pulled him onto his lap. Lee laughed as Brian sprang back up onto his feet, cursing and shouting.

  “Oh, come back, Brianna! Don’t you want to sit on my lap?” Lee fell onto his side from laughing so hard.

  Brian would’ve told him to fuck off, but something else was bothering him. He could’ve sworn that he felt it, but he wasn’t sure if it was really what he thought it was. Was Lee… hard? Was that his cock I felt when he pulled me onto his lap?

  This wasn’t a good sign. Brian had to finish cleaning the apartment before Lee got too drunk. He recalled how touchy-feely Lee got when he was drinking, often openly flirting with other women as long as Leah was out of earshot. It seemed that Lee had forgotten who the maid was that was cleaning the apartment. As far as Brian could tell, Lee believed him to be an actual woman and not his roommate dressed en femme.

  Hours passed by, and just as Brian was about to finally finish cleaning, things took a turn for the worse. He had lost track of how many beers Lee ended up drinking, and with each one his roommate got more and more horny.

  Lee had stopped calling him Brianna and started calling him by pet names, and finally insults until Brian’s nightmare came to fruition.

  “How much more cleaning do you have, slut?” Lee slurred.

  “I’m just about done—”

  “Yeah, sure. Come here and give me a blowjob.”

  Brian dropped the duster. “No fucking way, man.”

  “Oh? Is that so?” he said, whipping his phone out of his pocket. “Who should I send the pics to first?”

  Lee started listing off names aloud, and when he mentioned Leah, Brian finally walked over to him. He tried to swipe the phone from Lee, but even in his drunken state, his roommate was too fast for him.

  “Too slow, Brianna,” he said, slipping the phone into his back pocket. He spread his legs and pointed to his crotch. “If you want those pictures, you have to go through my cock first.”

  “Oh, fuck you, Lee. I’m not sucking your dick.”

  “You can lie all you want, but I know the truth.”

  “Bullshit,” Brian spat.

  “I know you’ve been horny all day. Prancing around in that outfit has gotten you all hard.” Lee snickered as he lifted up Brian’s dress, exposing his erect cock held flat against his stomach by the panties. “See? And besides, I heard you moaning and jacking off this morning.”

  “No… that’s a lie.” Brian looked away, his face turning red. He totally knows. Fuck! It’s true. It’s all true. I’ve been so fucking turned on by all of this.

  “Well? I’m waiting, Brianna. I command you to pleasure me.”

  A light bulb lit up in Brian’s mind. “What about Leah?”

  “What about her?”

  “You would be cheating on her.” Brian folded his arms.

  “As if. If I had sex with another chick, then I would be cheating on her. You? This? It doesn’t matter. Besides, what are you going to do? Tell her you dressed up as a maid and I blackmailed you into sucking my cock? Yeah, like that’ll save you.”

  Lee said nothing more. He just sat there and smiled and took another drink of his beer. He had won, and worst of all, he knew it.

  “I’ll say it one more time: Brianna, get on your knees and pleasure me.”

  Brian’s eyes shifted from his smug roommate to one of the bottles on the table in front of him. He could pick it up and smash it on his roommates head, knock him out and delete the photos.

  No, he has a password for his phone. Even though his passcode could be as simple as ‘1234’, Brian didn’t want to risk it.

  He took a step forward, and another.

  His hands failed to reach out and grab the neck of the bottle. Instead, he turned away from the table toward Lee, who spread his legs wider. He was wearing jeans and a t-shirt, and as Brian’s eyes moved toward the button on his pants, he saw it.

  Lee had a hard-on.

  It pushed up against the tough fabric of his pants and fought to be free.

  “Wait, you forgot something.”

  “What did I… oh.” Brian took a deep breath and sighed. “Yes, Master Lee.”

  He curtsied, then knelt down between Lee�
��s legs, swallowing hard as his fingers slowly moved toward Lee’s pants. Brian’s fingers trembled as he grabbed a hold of the waistline and fumbled with the button.

  I… I can’t believe I’m actually doing this. I’m… going to suck another man’s cock!

  Brian’s body betrayed him.

  His cock throbbed in his panties and he squirmed as lust washed over him. He grew warm and his face turned bright red as he unbuttoned Lee’s pants and pulled down the zipper.

  “Thatta girl, Brianna,” Lee purred.

  Brian yelped as Lee’s cock sprang free. It was bigger than he imagined, bigger than his own. Free of his jeans, Lee’s dick straightened out and fully hardened.

  Brian wrapped his gloved hand around it and slowly stroked, looking up at Lee for approval. His roommate groaned as he slid his hand up and down.

  “I didn’t ask for a handjob, Brianna!” Lee moaned. “All or nothing.”

  Brian took a deep breath before wrapping his lips around Lee’s dickhead. His own cock twitched underneath his dress as he moved his lips further down Lee’s shaft.

  His roommate placed his hands on Brian’s head and gently urged him further. Brian obliged, and his tongue caressed the cock in his mouth.

  Just get it over with, Brian, he told himself. As much as he repeated the mantra that he was doing this because he had to, it wasn’t all truth. Buried deep within was something else. A curiosity had taken hold early on in the day, a thought that persisted when Lee had made a joke about pleasuring him. Of course back then, Brian had believed it was just that: a joke.

  The more he pleasured his roommate, the more he enjoyed it. It was different than anything he could have imagined—not that he often wondered what it would be like to suck on a dick. Lee’s musk filled his nostrils as he neared the base of his cock. He pulled back, letting the thick rod fall out of his mouth to catch his breath.

  It remained hard in front of him, the taut skin slathered in a mixture of his saliva and Lee’s sticky precum. After a couple of breaths, he went back in and cradled Lee’s balls with his left hand as he stroked the base and bobbed on the upper half, occasionally licking the underside and tracing the head with his tongue.

  Lee writhed on the couch, moaning and groaning with approval. “H-Holy shit, Brianna! You’re like… the—oh god—best cocksucker ever!”

  The best cocksucker ever. That’s what you are. Brian moaned through the cock in his mouth as his dick twitched. He took his right hand off of Lee and reached under his dress to pleasure himself.

  Lee smirked. “You jerking off down there?”

  “Yes, Master Lee,” Brian said, taking his mouth off of the cock for a moment.

  Lee pushed Brian’s head away from his cock. “No more blowjob. It’s time I fucked you properly.” Lee scooted over onto the couch and pointed next to him. “Hands and knees!”

  Brian whimpered as he climbed up onto the couch. He uttered not one word of protest as Lee lifted up the back of his dress and pulled his panties down. Brian looked back at him over his shoulder and watched as his roommate slipped a condom onto this rock-hard cock and lined up.

  “I want to hear you moan. Beg for it.” When he didn’t, Lee slapped Brian’s ass. “I said beg!”

  Brian bit his lip. “Please fuck me, Master Lee.”

  Lee thrust in so hard Brian saw stars. The pain that filled him quickly gave way to pleasure as Lee buried his cock in his ass. He gripped Brian’s hips as he pushed in and pulled out in a fast, deliberate fashion. There was no romance or passion, just pure, hardcore sex.

  Lee treated Brian as he treated most of the women he had one-night stands with. They were there solely for his pleasure, nothing more.

  “Goddamn! Your ass is so tight, Brianna!”

  As rough as it was, Brian couldn’t get over the pleasure that filled him. From his time spent on the internet, he had come across many accounts of men and how much they enjoyed anal, whether they were with another man or their female significant others who fucked them with a strap-on. There was immense pleasure to be had from getting thrust into, especially when the prostate was stimulated.

  Brian fell forward onto his elbows, and the change in his position amplified the erotic sensations as Lee’s cock brushed up against his prostate. He moaned loudly, his voice soft and feminine. He sounded like the women that Lee would bang after his many parties—until he’d started dating Leah, that is.

  He reached back and grabbed his aching cock. He wanted release so bad. “I’m going to cum!”

  “So am I, slut!” Lee said with another firm slap.

  It pushed Brian over the edge, and he closed his eyes as he came all over the couch, his white-hot cum spraying everywhere. Lee’s thrusts grew uneven until he pushed his cock as deep as it would go into Brian’s ass.

  “Ohh, yeah!” he groaned. Through the thin latex sheath, Brian could feel Lee’s cock twitch and the tip of his condom fill with his cum. He kept his dick inside until he stopped throbbing, then pulled out, letting out a heavy sigh. “Well, fuck. I’m spent!”

  Lee climbed down from the couch and pulled his pants back on. He wiped the sweat from his brow and pulled his phone out of his pocket.

  “Clean up the mess you’ve made on the couch and you’re free to go. I’ve deleted the photos and you’ve held up your end of the deal.” Lee didn’t even look back at Brian as he whistled and walked toward the front door. “Night’s still young. I’m hitting up the bar.”

  The door slammed shut and Brian finally relaxed. He straightened up and slowly got off of the couch, narrowly avoiding the large puddle of cum. Back on his feet, he pulled his panties up and cleaned off the couch.

  It was finally over. The apartment was the cleanest it had ever been, and Brian had never felt so dirty.

  He shuffled into his bedroom and stripped out of the costume. He kicked his heels toward his closet and tossed the rest of the clothes onto the floor by his bathroom door.

  He peeled off the wig and set it on the counter and placed the jewelry next to it. Overjoyed to be finally out of women’s clothes, he stepped into the shower and tried to wash the dirt, grime, shame, and memories of the day away.

  But no matter how hard he scrubbed or how long he let the hot water flow over him, the thoughts and feelings remained, and he knew it would only be a matter of time before he cross-dressed again.

  In fact, it wasn’t even a week.

  “I’ll see ya next week,” Lee said as he wheeled his suitcase out the front door. Brian watched him leave and sighed with relief. He had the apartment all to himself for an entire week and didn’t have to deal with Lee’s drunk ass tearing the place up and making a ruckus.

  Brian sat on the couch and lifted his legs onto the table. It was finally peaceful.

  But he quickly became restless, and as much as he fought it, an hour later he returned to the couch wearing his fishnet stockings, red heels, black lace panties, wig and his entire maid costume.

  He slid down onto the couch, closed his eyes and moaned as he jerked off with his gloved hand.

  He was so wrapped up in his erotic stimulations that he didn’t hear the front door unlock and open. Brian’s moans drowned out the sound of high heels on the wood floor, and it wasn’t until Leah screamed that Brian came out of his erotic trance and scrambled onto his feet.

  He stood in front of the couch, his hands covering the front of his dress and stared at Leah, his face blood red.

  Lee’s girlfriend stood and stared back, and after a few silent moments, her posture shifted. She closed her slack jaw and folded her arms, looked at Brian through her sapphire-blue eyes and smiled.

  TORN APART PART 2:

  REMODELING

  The silence was agonizing.

  Brian’s heart was beating as fast as a hummingbird’s as Leah stood in the foyer and slowly looked him up and down. Her smiled curled into a satisfied grin and she took a step toward him.

  Brian swallowed hard as he took her in. Despite the fear, dread, and pa
nic that filled him, he couldn’t help but survey her beauty. She was a gorgeous woman. She had long blonde hair and her eyes were a sapphire blue that sparkled like the gem itself. She wore dark red lipstick that was both professional and sensual.

  Leah slowly walked toward him, the clicks of her heels echoing in his head like the ticking of a clock. Brian shook nervously as she neared him, her eyes moving all over his body, inspecting him as if she was a potential buyer.

  Why? Why is she so calm and collected about all of this?! Brian opened his mouth to speak, but the only things that came out were quiet whimpers.

  “Oh? You got something to say?” Leah said, moving behind him. “I never knew you were into this kind of thing, Brian. I mean, you are thin and scrawny, and with the right padding you would have a very sexy body.”

  Brian bit his lip, his cock still rock hard underneath his dress. He could only imagine what he’d look like to have a woman like Leah transform him—someone who actually knew how to put on makeup and had a wide array of jewelry and outfits at her disposal.

  His eyes scanned her own clothing as she moved back in front of him. She had on a tight white blouse, the long sleeves folded at her elbows. The buttons were a shiny metallic gold that reflected the lights of the apartment. The top looked to be custom tailored for her perfect body, and Brian couldn’t get past how well it hugged her frame.

  Below the cream-colored blouse was a black pinstriped pencil skirt that stopped above her knees. It had a long slit up the side, and when she shifted her weight onto her other leg, Brian could see the tops of her stockings through the opening. He swallowed hard as beads of sweat slid down his forehead.

  Leah was a sensual dresser who knew how to use her body to her advantage. She skillfully wielded it, and could have any man—or woman—eating out of the palm in her hand.

  Many times Brian witnessed her using this ability on Lee, getting him to do chores and other tasks for her. He’d do them in a heartbeat, but if anyone else asked him to do the same thing or lesser, he’d tell them off.