Lipstick & Miniskirts

by John Dylena

  He sighed and climbed up onto the wooden table next to the machines, planning on waiting it out in his towel when something caught his eye.

  When he’d walked into the laundry room, his focus had only been on the machines. His tunnel vision had prevented him from noticing that the walls of the laundry room were filled up with lots of women’s clothes and underwear.

  “Whoa.” He climbed off the table and walked up to the racks.

  Various ladies’ undergarments were hanging on the walls in all sorts of colors, styles, and fashions. An idea popped up into his head, something he’d thought was lost forever. He was surprised to find that it wasn’t.

  Jessica’s words on how she and Susan weren’t going to be back until late that night echoed in his head. Breathing deeply, he browsed through the selection, gingerly touching all the different fabrics.

  He gently pulled down a black bra and a matching pair of panties and set them on the table, making a gap on the rack so that he’d know where to put them back. Scanning the rest of the rack, he found something even better: a black corset with cups and garters. He grabbed it, put the bra back, and then set the new garment on the table.

  He dug through one of the baskets and pulled out a pair of black stockings and set them on the table next to the other items. His mind was set. There was no going back.

  Taking one more deep breath, Allen set his towel on the floor. The panties were the first to be put on, the light material tickling the insides of his legs. Then he climbed up onto the table and proceeded to roll the stockings up his long, slender legs. The dark nylon hugged his legs, hiding the little hair he had on them. After sliding both of them on, he got up off the table, grabbed the corset and stepped into it, pulling it up his body.

  He reached behind to his back and fastened the clips, thankful that it wasn’t laced. Needing to stuff the bra, he grabbed some socks from the large basket and filled the cups.

  “Man this is tight,” he said to himself. He felt up the sides of his body and noticed the more defined hourglass shape the garment gave him. His hips were anything but womanly, but the narrowed waist helped with the illusion. He bent down and fastened the tops of the stockings to the garters that hung from the corset.

  Looking down at his stocking-clad feet, he realized he was missing the most important piece: shoes.

  It was easy enough grabbing the clothing from the laundry room, but going further required infiltrating the ladies’ bedrooms and bathroom. He made a mental note to put everything back exactly where it belonged. The last thing he wanted was the women to find out he wore their clothes.

  The nightmare scenario played out in his head. They came back and found their stuff disturbed. What then? Would they chastise him? Call him names? Would they kick him out of the apartment?

  His mind switched to the other possibility. What if they forced him to dress up, instead? Would they turn him into their slave? Make him clean and serve them in some ridiculous maid outfit?

  He stopped before the scenarios got out of hand in his mind. No, they won’t find out. They mustn’t.

  But why couldn’t he stop? If he wanted to make sure they didn’t find out, why not just put the undergarments back? His old fantasies were pulling him forward, urging him to continue.

  You know you want this.

  He grabbed his towel and walked out of the laundry room, nearly slipping on the wooden floor of the hallway. He quickly made a stop in his room, tossing the towel onto the floor and then stood in the hallway outside Jessica’s door. He remembered Susan occasionally poking fun at Jessica because she apparently had big feet. If Susan’s jests had some truth to them, then there was a chance Jessica’s shoes could fit his feet. The stockings would help if they were a tight fit, but if they were too small, his feet would cramp and the experience wouldn’t be the least bit enjoyable.

  He slowly opened her door. The sun was shining into her room, its light coming down right on her closet door. He walked up to her closet and slid it open.

  His eyes turned to her bed. Jessica was a beautiful woman; a tall brunette with light green eyes. She was smart and funny, yet in the few months he’d lived there, he’d never heard her mention a boyfriend.

  Susan, on the other hand, was more proactive. She was shorter than Allen, but her killer body got all the attention from the boys. She was too outgoing for him, and she always seemed to get a little too drunk when she went out to the bars or clubs. Allen would be lying if he said he never fantasized about having sex with either of them.

  Bringing his mind back to the matter at hand, he stepped into Jessica’s walk-in closet looking for her shoes. Fortunately, he wouldn’t have to do any digging to find them; they were all neatly lined up on the floor. He laughed when he saw how organized they were. It made it easy to find the ones he wanted.

  After glancing over the selection, he picked up a pair of black patent pumps with five-inch heels. The black leather shined brightly, as if they had just been polished that morning.

  He took the shoes and sat on the edge of her bed. He set them on the ground and slipped his feet into them, praying they would fit. Like Cinderella being found by her prince, the shoes fit perfectly. They were slightly small, but the stockings helped them slide on, and they were snug enough to where they wouldn’t come off when he walked.

  He let out a sigh of relief and stood up. The heels were high enough to make him wobble, even while he was standing still. Taking a minute to adjust, he slowly stepped forward. He stopped in front of the full-length mirror.

  He admired his reflection, focusing on his body from the neck down. Seeing his male head on top a body clad in lingerie and wearing high heels easily broke the illusion. Years ago he would’ve killed for this opportunity. Two large closets full of clothes and shoes and dressers full of every type of undergarment he would imagine. All at his disposal.

  Allen marveled at how well the clothes fit him. At how the stockings accentuated the curves of his leg and how the corset shaped his otherwise straight body. He turned and stared at his ass in the mirror, bending his knees slightly and leaning forward to push it out further. The heels made it look fuller, perkier. He wiggled his ass and bit his lip playfully, causing his groin to stir to life, hardening in his panties.

  The beeper on the washer and dryer went off, and the suddenness of it scared him so much that he almost fell over. After he’d regained his composure, Allen walked to the laundry room, savoring the sound of his heels clicking on the hardwood floor, and switched loads. A few moments later, he excitedly returned to his “adventure.”

  His stomach rumbled, reminding him that it was still morning and he hadn’t had breakfast yet. Deciding to stay dressed, he walked into the kitchen and made a cup of coffee and toast. He remained standing, finding it rather uncomfortable to sit in the shape wear. Looking down at his body, then at the clock on the wall, he made the decision to go into the next phase.

  I can’t do this half-assed. I've gone this far. I gotta go all the way.

  Allen put the mug into the sink and walked into the ladies’ shared bathroom. Looking around, he noticed there was a brunette wig on the vanity, as well as a ton of various kinds of makeup.

  That's the wig that Susan wore the other day when she wanted to see what she looked like as a brunette.

  Susan had very blonde hair and was always proud to say that it was naturally that bright. However, she was always curious as to what she would look like with other hair colors. Instead of dyeing her hair, she would buy a wig and wear it around for a week. He remembered her trying on red hair, which she stopped after two days.

  He sat down at the vanity and began the long process. He had shaved his face not too long ago, so his skin was nice and smooth. He applied some foundation, and then slowly progressed further.

  Not knowing a thing about makeup color theory, he went with whatever he remembered the women wearing: purplish-gray eye shadow, mascara, a light layer of blush, and finishing up with a coat of ruby red lipstick.
He decided not to try to put on fake fingernails, as the smell would linger in the apartment.

  When he was done, Allen grabbed the wig and put it on. He stood up and walked back into Jessica’s room and looked into the mirror.

  What he saw wasn’t Allen, but a gorgeous brunette staring back. She was feeling up her sides, rubbing her fingers up and down her nylon encased legs. Her right hand slid up the front of her panties, up the corset, in between the cleavage, and eventually traced her lips. The bulge in her panties grew, and the sight of it snapped him back to reality.

  “Oh my god! What am I doing?!” he said as he snapped out of the trance. “I need to cover up.”

  He looked around and found the black dress that Jessica was wearing the other day. Not wanting to see himself wearing the sexy lingerie, he slid the dress on.

  He left her room and closed the door, heading for the living room. The heels clicked on the floor and echoed in the empty apartment.

  He sat down on the couch, hoping that watching the TV or maybe a movie would take his mind off of recent events. But even with the TV on, his mind kept going back to when he was standing in front of the mirror. The woman in the reflection was beautiful. Realizing that that woman was none other than himself was scary.

  The TV failed to distract him. After watching no more than twenty minutes of it, his body was twisting and turning with nervous anticipation. He had to stop before things got out of hand. If he let himself go, Jessica and Susan might find him in one of their bedrooms playing with their toys. Or worse, he might just leave the apartment and go looking for a seedy back alley somewhere.

  Returning to Jessica’s room, Allen slid off the dress and hung it back up. Once more saw himself in the mirror. He sat down on her bed next to the night stand. He knew that if she had any toys, it would be there. He bit his lip, his eyes fixated on the small drawer.

  Then the phone rang, and he nearly jumped out of his skin.

  It was enough to end the internal battle. He removed the wig and put it back on the fake head on the counter and left the bathroom. He kicked off the high heels and put them back into the closet. Closing her bedroom door behind him, he returned to the laundry room.

  Everything was exactly how he’d left it. The dryer had finished it cycle and his clothes were calling out to him.

  Removing the stockings and panties, he checked for any signs to show that he wore them, squinting as he looked for any stray hairs in the lacy garment. When his search came up empty, he put them back in the basket where he found them and removed the corset.

  After putting lingerie back up on the racks where it belonged, he went back into his room and took another shower. He scrubbed his face clean of makeup and laid down in the tub, letting the water pound onto his face and chest.

  After awhile, the phone rang again, and he got out of the tub and dressed himself in his newly-laundered jeans and t-shirt. Then he went into the kitchen to check the messages. Both were from telemarketers.

  His stomach rumbled, and in response, he made himself a sandwich and sat back down on the couch to watch a movie while he ate his lunch. The images from his dress-up session replayed in his head as he tried to focus on the film flickering across the screen.

  The day went by as he went from the TV to his computer and back. After hours of movies, television, and video games, he looked out the window. The sun was low on the horizon and the sky was getting dark. He shut down the console and decided to go out for dinner.

  When he returned, Jessica was sitting on the couch. Her posture and demeanor reminded him of the father of the girl he took to the prom.

  She was waiting for him.

  “What's up?” he asked her.

  “What were you up to today?” she replied tersely.

  “Oh, nothing. I spent half an hour in the laundry room waiting for my clothes, but other than that, my day was rather boring.”

  “Did you do anything to the rows of clothes in the laundry while you were waiting? It looks as though someone took them off the shelf and put them back hastily.”

  Oh shit, he thought. Did I get caught? Does she know that I wore her underwear, makeup, and shoes? Quick, Allen, come up with some bullshit excuse.

  “Umm… yeah, I did. When I ran in there after getting your note, my feet were still wet, and I slipped and knocked a few things over. So I put them back, hoping you wouldn’t notice.”

  She eyed him suspiciously. “Right…”

  Allen let out a quiet sigh of relief as Jessica got up off the couch walked into her room, closing the door behind her. He cut across the living room, believing he was in the clear.

  “Allen, come in here,” she said through her door.

  Shit.

  He froze. His hands were shaking and his mind was racing. That’s all, folks. This is the end for me. I’m doomed.

  Allen opened the door slowly and poked his head into her room. Jessica was sitting on the edge of her bed. Her closet door was open. She motioned for him to come in.

  After he walked in, she got up and closed the door behind him. She then grabbed his shoulders and walked him over to her closet and pointed to something.

  “See something wrong?” she asked him, pointing to her shoe rack.

  His heart sank when he saw it. His mouth went dry as his eyes focused on the high heels he was wearing earlier. When he’d finished with his dress up, he had put her shoes back in the wrong way, and she had noticed.

  The racks of clothes in the laundry were easily defended with his lie, but the shoes? There was no logical reason to explain that other than the fact that he did something with them. How could I have missed that?

  “So tell me, what were you doing with my heels?” Jessica asked, staring at him intently. “Did you slip and knock them over, too?”

  Allen couldn’t think of anything to say. He wanted to be clever, but he knew it would be pointless. In fact, he suspected that it would’ve made the situation worse.

  She walked him over to her bed, sat him down, and then sat down next to him. “I’d say that the stunned look in your face and the fact that you’re not saying anything answers my question. By the way, I knew that you were lying earlier. The front of the panties were slightly stretched out, and that could only mean one thing.”

  He was expecting her to kick him out of the apartment right then; no excuses, no chance to defend himself. What she said next was something he didn’t expect.

  “So… whatcha think of women’s underwear?”

  “W-what?”

  “Let me rephrase it: did you like wearing my underwear?”

  “Uhhh…”

  “I’ll take that as a yes,” she said as she smiled. “Come on, Susan had to drive up north for work. She isn’t gonna be back until tomorrow evening. Show me what you wore… We can play dress up!”

  He looked at her, confused, disappointed, angered. She was supposed to kick him out of the apartment or call him names, not smile and have him dress up again.

  “Why are you so happy? Shouldn’t you be grossed out?”

  “I was, at first. Don’t get me wrong—I am very upset with you. But I was the only girl in the family. Now that I know you’re a crossdresser, it’s like I have a secret little sister.”

  “Well, I'm not. I haven’t done anything for a very long time, and even when I did, it was only once or twice. Most of time I would just think about it, but I haven’t done any of that for years.”

  “No worries. I won’t tell anyone. Come on, show me what you wore!” she said, pulling him off the bed and into the laundry room.

  Like a giddy schoolgirl, she ran into the room and jumped onto the table, waiting to see what he chose. He walked in slowly, took a deep breath, and walked up to the large rack. He grabbed the pair of panties that she found and he also grabbed the corset with the garters.

  “Oh my god! That means you also wore stockings!” She was even more excited. He grabbed the stockings out of the basket and handed them to her. “Good choices. Now I see w
hy my shoes were messed up. Come on, let’s get you dressed!”

  She both grabbed his hand and the clothing and pulled him back into her room. Following her commands, Allen stripped in front of her and put the garments on. Panties first, followed by the stockings and then the corset. She helped him fasten the clips on the back and then she handed him the heels.

  Jessica frowned as she inspected him. “Still missing a few things, though…” Then she snapped her fingers. “I’ve got it!” She pulled out a pair of false breasts from her dresser and placed them into the bra.

  “Don’t worry, what you see is all real. I got these for a Halloween costume a while back. They’re big enough to where it’ll look like you have breasts!” She wrinkled her nose. “I don’t like that bulge in your panties, though. We might have to do something about that.”

  Allen sighed. He’d always wanted to get naked in front of her, but not like this. He wanted her to take off her clothes, not put them on him.

  He took off the panties and she handed him one of her bikini bottoms. It was tan-colored and almost matched the tone of his skin.

  “Its gonna be tight,” she said. “That material will help hide your manhood.”

  He slid them up. She was right. The tight material of the swim suit forced things to shift around. The bulge was gone. She handed him the black panties and he put them back. From the neck down, he had the body of a woman.

  “Okay, let’s get you dressed,” she said. She browsed through her closet and pulled out a black mini skirt and a white blouse for him to wear. The skirt was very short, stopping several inches above his knee, and the blouse was made from a semi-sheer fabric that Allen couldn’t help but imagine would turn see-through when wet. It had sleeves that stopped at the elbow and a V-neck that showed off his new cleavage. Though the outfit was comfortable, he felt that the skirt was too revealing.

  “Looking good,” she said. “Almost done!”

  “Isn’t this enough?” he protested

  “No,” Jessica said with an evil smile. “You set the terms when you decided to wear my clothes, and now you're gonna enjoy them.”