Lipstick & Miniskirts

by John Dylena

  “Yup, that one. Stockings need to be black fishnets, the panties should be black lace, and the heels… make those ruby red—five inches or taller.”

  “Five inches! Are you kidding me?! I won’t be able to walk in those.”

  “Well, buy them now and start practicing!” Lee laughed as he slapped Brian on the shoulder. “I like blondes, so you’ll need a blonde wig—style doesn’t matter. I’ll get the jewelry and borrow some of Leah’s makeup, and that covers everything. You have one week to get the outfit together and buy all the necessary cleaning supplies. Remember, you’ll be dusting and vacuuming, cleaning the windows, mopping the floors, scrubbing the kitchen and bathroom, and doing the dishes—and anything else that comes to mind on that day since, you know, you’ll be ‘serving me.’ ”

  “What about the trash?” Brian said, trying to ignore the thought of having to serve Lee.

  “That… that you can do whenever. As much fun as it will be seeing you all dressed up, it is for my eyes only.”

  Oh, thank god, Brian thought. As bad as it would be to dress up like a maid, it would be the end of him to have to go out in public in that costume. The front door of their apartment faced the atrium of the complex, and the trash chutes were down at the end of the walkway. Taking out the trash would mean possibly exposing himself to a majority of his neighbors.

  For the following week, Lee teased him over every package that arrived, and on Saturday night, he had Brian lay out all the items on his bed. Lee couldn’t hide his laughter as he looked at the pieces of the costume that Brian would be forced to wear the next day.

  Everything was there and passed Lee’s inspection.

  “Oh, one more thing that you’ll have to do,” he said, “and I suggest doing it both tonight and tomorrow.” He ran out of Brian’s bedroom and came back carrying a plastic shopping bag. Lee dumped out the hot pink razor and ladies’ shaving crème and Brian’s face went pale.

  “No… that was not part of the original deal!”

  “Technically, it was. You can’t be a sexy lady maid if you don’t shave your body. Though you are pretty sparse. Just be glad you aren’t like Stu.”

  Both men cringed as they recalled their mutual friend. Stu was covered head to toe in thick black body hair all over his arms, legs, chest, back… even the back of his neck.

  Brian threw his head back and sighed. “All right, fine.”

  “Oh right, the makeup.” Lee returned with another bag. “So, Leah has a lot of makeup and she’s out of town for the next couple of days, so I don’t have to worry about her looking for it. I grabbed what I think you’ll need.”

  “What did you grab?” Brian said, looking through the plastic bag.

  “Lipstick, foundation, blush, mascara, and eye shadow.”

  Brian held up the tube of lipstick and removed the cap. The lipstick was bright red, matching the color of his heels. He returned it and took the bag from Lee.

  “What about my jewelry?”

  “That’ll come at the very end once you’re all dressed and ready to go.” Lee winked and walked out of his room. “Good night, Brianna.”

  “Oh, fuck off, Lee.”

  “In…” He looked down at his watch. “…four hours, that’ll be Master Lee.”

  Closing the door behind his roommate, Brian sighed and returned to his bed. He thoroughly eyed each piece of the outfit he was to wear tomorrow and held them in his hands, his fingers stroking the light, delicate fabric.

  Lastly, he held up the dress. Without it, the items on the bed would just be ordinary lingerie. It was the most important piece.

  He held it against his chest and turned toward his full-length mirror. It was a perfect fit, and as he held it, the urge to actually put it on got stronger and stronger.

  He bit his lip, his face turning red and his dick hardening in his boxers as he held the dress out in front of him.

  Only for a minute… just… to see if it fits.

  Nodding, he pulled off his shirt, kicked off his pants and stood in his boxers. He stepped into the wide neck and pulled it up. The strapless neckline had elastic built into it, which clung to his chest and kept the dress from falling down as he slid his arms through the attached sleeves.

  The white ruffle lining tickled his body, and without the petticoat, the short hem fell flat onto his legs. Brian turned toward the mirror, watching as the hem flared out from the quick spin. He giggled quietly, looked at his reflection curiously, and then grabbed the hem of his dress and curtsied.

  “As you wish, Master Lee,” he whispered.

  All at once, it hit him.

  Brian took a step back as a wave of arousal flowed through him. He bit his hand as his body grew warm. He felt his cock harden and his knees buckled under the weight of his lust, and he scrambled out of the dress before it could take him any further. The thoughts and visions that coursed through his head scared him.

  He was serving Lee, and he was enjoying it.

  No… I can’t go through with this. Putting his clothes back on, he went out into the living room to find Lee out on the couch, half-awake and watching recaps of the day’s sporting events.

  “Hey, Lee, what if I want to back out of this deal?”

  “What?” his roommate said, lifting his head off of the couch in a daze.

  “I don’t want to… dress up tomorrow and do this.”

  “Then you owe me a thousand bucks to pay for a couple of sexy maids.”

  “Fuck. Fuck! Damn it.”

  “Dude, you already bought the outfit, just fucking do it, you whiny baby. Don’t be a sore loser.” Before Brian could retort, Lee turned the volume up on the TV. “Shouldn’t you be shaving right now?”

  Brian returned to his room, sighing as he stripped out of his clothes, grabbed the shaving gear, and hopped in the shower. He watched his body hair fall off into the drain as the hot water flowed across his now silky-smooth skin.

  “Tomorrow is really going to be something,” he said to himself as he climbed into bed and slept a dreamless sleep.

  He had the rudest alarm clock of them all.

  “Wakey wakey, Brianna!” Lee pounded on his door.

  “Ah, what the fuck, man!” Brian groaned as he rolled over in his bed. He forced his eyes open and checked his phone. It was six in the morning.

  “That’s Master Lee to you!” his roommate shouted as he opened the door. “Up and out of bed, you lazy maid. Shower, get dressed and put your makeup on, then come get me.”

  Lee slammed the door shut and Brian cursed him under his breath. As annoying as he was, Lee was right. Brian had lost the bet fair and square, and it was either do what he had to or hand over a thousand dollars.

  Brian mumbled to himself as he threw the sheets off and wobbled into the bathroom. He stripped out of his clothes and inspected his body. His hair had yet to start growing back and he was as smooth as he was last night. Thankful that he didn’t have to shave a second time, he showered and returned to his bedroom.

  His eyes went straight to the black dress hanging on his closet door. Below it laid the bright red heels, and the rest of the items were scattered across his desk and dresser.

  Brian sighed and made fists as he summoned the strength to walk toward the outfit. He dropped his towel and stood before it naked. It’s now or never. Let’s just get this over with.

  He reached over and grabbed the panties, hesitating as he lifted his leg up and pointed his foot toward the leg hole. He bit his lip and slid it through, then quickly stepped into the other hole.

  The black lace panties ticked his hairless groin and he nodded at how strangely comfortable the garment was. It was light as a feather and gentle on his smooth body. It cradled his ass and caressed his slowly hardening cock.

  No! Stop! Damn it, you’re not supposed to get hard from this!

  Brian groaned as he tried to fill his brain with thoughts to counteract the effects of the panties. He kept focusing on things other than the arousal as he pulled the stockings
on.

  Just like the panties, they were light and gentle. They hugged his legs and gave them a more feminine look. They brought out his muscle tone and made them look long and slender.

  Ugh, I look like a hooker with these fishnets on, Brian thought as he looked down at his legs. Rolling his eyes, he took the dress off of the hanger and held it in front of him. Biting his lip and praying, he stepped into the dress in the same exact manner as the night before.

  When no urge to curtsy came to him, he sighed with relief.

  “Hurry up, Brianna! I’m getting hungry,” Lee shouted as he banged on the door. Brian swallowed the expletives that were itching to come out of his mouth and ignored his demanding roommate. Lee must’ve read his mind, because Brian could hear him laughing as he walked away from the door and turned on the TV.

  Brian filled the skirt of the dress with the white petticoat. It flared the hem out, revealing the scalloped tops of his fishnets. If he bent over at all, his ass would be on display.

  So no bending over. Just have to squat and kneel.

  Deciding to put the heels on last, Brian sat down inside his bathroom and started applying the makeup. It was an arduous task, but in the end he somehow came out of it not looking like a drag queen. The lipstick was a bright red, his blush a rosy pink, and his eye shadow was a deep, rich purple.

  Lying on the counter next to the makeup was the blonde wig. Instead of falling down past his shoulders in waves and curls, it was gathered up on the back of the head in a messy updo. Brian tucked his short brown hair into the hairnet that came with it and placed the wig on his head.

  The transformation finally set in.

  Brian stumbled backward from his bathroom mirror, his eyes wide and his jaw slack. He leaned forward, staring at his reflection. A woman looked back at him. If it wasn’t for his flat chest and Adam’s apple, Brian would’ve been a convincing woman.

  No, not again! He bit his lip and looked down. The petticoat masked the raging erection poking out the top of his panties. He cautiously lifted up the front of his dress and looked away from the sight of his throbbing cock pinned against his stomach.

  He felt blood rush to his cheeks and he squeezed the hem of his dress so hard his knuckles turned white. He squirmed. How could he be so aroused by all of this?

  Brian opened his eyes and looked back at his reflection. He whimpered and his red lips quivered. He brought his hand down to his cock, his fingers moving on their own as they wrapped around the rigid shaft and started pumping.

  His hand moved faster and faster, his eyes refusing to look away from his reflection. His lips came together and a soft, honey-sweet moan escaped from between them. The blush vanished among the red in his cheeks as he continued to masturbate to his girlish appearance.

  He reached for the tissues just in time to catch the white-hot cum that erupted out of his tip. Stars filled his eyes as the euphoria washed over him. He stumbled backward as the remnants of his orgasm oozed out into the tissues.

  Oh, fuck, he thought as his mind came back down from the erotic high. Embarrassment quickly filled him as he wiped the last droplets of cum off of his dick, sighing with relief as it went flaccid.

  “What the fuck is taking you so long? Are you jerking off in there?!” Lee banged on the door.

  “Calm the fuck down!” Brian shouted back. “I’m… on the toilet!”

  Lee’s anger quickly faded. “Well… finish up, man. You don’t have all day.”

  It’s only like, seven in the morning!

  Tucking his cock back into his panties, Brian put on the white elbow-length gloves, added the little headdress to his wig and slipped into the high heels. He wobbled around for a moment, and after getting his balance and adjusting his dress, he called out to Lee.

  “All right, man. I’m… ready.”

  He waited anxiously. After a few brief, agonizing moments, the doorknob turned and his heart leapt into this throat as his roommate laid eyes on him for the first time.

  Lee’s hand slid off of the handle as he stood in the doorway. His jaw fell so hard it would’ve hit the floor if it wasn’t attached to his head. Lee rubbed his face and blinked several times.

  “No… this cannot be real.” He walked past Brian and opened the closet door. “Brian, where the fuck are you? This isn’t funny.”

  “Dude, it’s… me.” Brian said. The last word came out slowly and awkwardly. That’s right. I’m standing here in high heels, fishnets and a maid outfit. I’m the one cross-dressing, and apparently, I’m pretty damn convincing. I’m the one who just jacked off to his own appearance.

  “I can’t believe it, man. You actually look pretty hot. Though you have no breasts.” Lee giggled as he poked Brian’s chest, yelping when he slapped his hand away.

  “Hurry up and give me the jewelry so I can get this over with.”

  Lee nodded and left the room, returning moments later with another bag. He set it on the bed and pulled the first item out.

  “Right, first the earrings. These are clip-ons, so no need to get your panties in a bunch.” He held them in front of him. They were gold chandelier earrings decorated with rhinestones. “I like the wig,” Lee said as he clipped them to Brian’s lobes.

  “Thanks,” he replied.

  “Master Lee.”

  “What?”

  Lee frowned. “Thanks, Master Lee. Remember, you have to call me that—and at least try to talk like a woman.” Brian rolled his eyes as his roommate grabbed the next piece. “A rhinestone choker.”

  The choker shone brightly in the bedroom, the lights reflecting off of the many rows of tiny square rhinestones. Lee stepped behind Brian and clipped the choker on him. It sat comfortably on his neck.

  “Heh, you’re finally taller than me. One more thing.”

  “What is that?”

  “It’s an anklet,” Lee replied, holding the thin gold chain.

  “Are you fucking kidding me? Did you seriously get me an anklet that says ‘slut?’ ”

  “Yes I did, Brianna! I didn’t want to do this, but…” He took a couple steps back and whipped out his phone. Brian’s eyes went wide when he heard the familiar clicks of pictures being taken. “Now, either you do as you’re told or these pictures get sent out to everyone.”

  Brian made fists. He wanted so badly to punch Lee, knock him out and take his phone from him, but his roommate was strong and fast. He would easily dodge Brian’s blow and everything would go downhill fast.

  “Do you understand?”

  “Yes.”

  “Brianna!”

  Brian cursed him under his breath. “Yes, Master Lee,” he said a second time in his best female voice.

  “Good girl. Once I put your anklet on, you are to begin your day of servicing me.” Brian silently watched him kneel down and clip the anklet on. When Lee stood back up, he wiped his hands and smiled. “I want you to reply to every command I give you with a curtsy. Understand?”

  Brian nodded.

  “Good. Now, I am hungry. I want you to cook me a breakfast of bacon and eggs with a side of toast and a nice hot cup of coffee. Two eggs scrambled, three strips of bacon, and two slices of toast.”

  “Yes, Master Lee,” Brian replied, curtsying.

  As he dipped, he felt his cock start to harden. Yes, Master Lee, he heard again in his head. He sounded so weak, so submissive, so… feminine.

  Brian quickly walked past Lee, his hands clasped in front of him, hoping his roommate wouldn’t catch the crimson color on his cheeks.

  Unknown to his roommate and temporary master, Brian had in fact taken Lee’s advice about the heels. Knowing full well that he’d be spending quite amount of time in them—despite his optimistic and unrealistic estimate on how quickly he’d clean the apartment—they were the first item he bought and they’d even arrived a day early.

  They were beautiful shoes made from quality patent leather that shined in the lights of his apartment. When they first arrived and he held them in his hands, he was in disbeli
ef that he had spent so much money on the shoes. They were close to a hundred dollars, from a highly reputable company with a five-star review on the online retailer.

  The heels had slid onto his feet perfectly the first time he’d worn them. They were comfortably snug and his feet rested on the arch. Brian had sat on the edge of the bed and stared at them. They were lighter than he’d imagined, and with Lee gone for several more hours, he took the opportunity to walk in them.

  Brian stood up and immediately felt like he was a toddler learning to walk. The high arch of the shoes forced him forward and he almost fell face-first onto the floor. Getting his balance, he straightened up and stood awkwardly as the sexy footwear forced him to stick out his chest and ass.

  Looking over at his reflection in the mirror, he could see why women would wear them when they wanted to show off their assets. His flat ass now had volume and his legs looked long and slender. If he had breasts, they would be up and out. He couldn’t slouch and he stuck his arms out to the sides as he took his first step.

  It was a slow and tedious process. Each step was carefully calculated and Brian’s eyes didn’t leave the floor. His feet wobbled with each step, and he hoped and prayed that the next one wouldn’t shatter his ankle.

  Minutes passed as he moved about the apartment. His pace quickened and his paranoia faded as he adjusted to the shorter strides he had to take. Brian smirked as he recalled the instructions from the how-to video he had watched. The woman in the video made it look easy and her instructions were simple. He was sure all he had to do was practice.

  Brian walked heel to toe until he was confident enough to take his eyes off the ground and look straight ahead as he walked. He found that his hips swayed with each step and he felt so tall in the five-inch heels. After a while, his feet grew tired and his legs surprisingly sore, and with Lee home any minute, he’d retired the shoes to their box until the next opportunity arose.

  He’d had chances to practice every single day, and when the day finally came, Brian strode out into the kitchen with confidence. Walking in heels was no longer foreign. He was even able to run very short distances in them. In fact, Brian had grown so attached to the footwear that he didn’t want to get rid of them once the day was over.