Lipstick & Miniskirts

by John Dylena

  She grabbed his hand and led him into the bathroom. She sat him down on the chair, cracked her knuckles, and began the makeover. One thing he noticed was that she was using nearly all of the available items, while he had only used a few. He hoped and prayed that her knowledge of the dressing up only went as far as the clothes and didn’t extend to the wig and makeup.

  Part of him was excited, as he’d finally see what he would look like with makeup applied by a professional. His knowledge of the makeover process was so limited.

  His thoughts were interrupted by a sharp pain in his forehead.

  “Ouch! You’re not plucking my eyebrows, are you?”

  “Nah, but I am getting rid of what looks like a mono-brow that’s starting to grow.”

  The entire time Jessica worked on him, he was turned away from anything that he could see his reflection in. He knew she was done when she plopped the wig on. Before he could see himself, she put a blindfold on him.

  She walked him into her bedroom and sat him down on her bed again. She grabbed a few pieces of jewelry and put them on him: a bracelet, a ring, a necklace, and some clip-on earrings. She then stood him up and sprayed some perfume on him.

  “Was that necessary?”

  “Of course, I don’t want you smelling like a man in my clothes.” What happened next shocked him. She removed the blindfold and he saw his reflection in the mirror—rather her reflection. Compared to what he looked like now, his earlier appearance had, in fact, looked like a man in drag. All he could do was drop his jaw. Anyone who saw this would have no doubt in their mind that what they were looking at was one-hundred-percent woman.

  Allen was shaken to the core. He looked like a woman, he smelled like a woman, and he couldn’t believe that the person staring back at him was not a woman. He didn’t know what to do or say. He was speechless.

  Jessica grinned. “Looks good, don’t it? I’ll bet you weren’t expecting this. Okay, give yourself a twirl.”

  He looked at his reflection from every angle. His heels accentuated his slender calves and elevated his firm butt, while the dark stockings hid the hair on his legs. The corset and fake breasts granted him an hourglass figure that any many would drool over.

  Jessica squinted, looking him over. “Time to come up with a name. Umm, let’s see… how about… Jennifer?”

  “Jennifer?”

  “Yep,” she said definitively. “Jennifer. It has a nice ring to it.” Come on. Let’s begin your training. You're going to stay dressed for the rest of the night, and you’re going to walk, talk, and act like a lady.” She smiled. “I'm thinking tonight, we have some wine, talk about men, and watch a nice romantic comedy. Then afterward, we can do more dress up! Oh god, I'm so excited!”

  Allen sighed. “I guess no amount of arguing or protesting can stop you.”

  Jessica smiled slyly. “Don’t lie, Jennifer. I know you want to.”

  Allen felt his shoulders slump. She’s right. I do want this.

  After several glasses of wine, intense lessons, and a romantic comedy, Allen was taking on the role of Jennifer rather well. He has walking, talking, and acting like a lady: crossing his legs when he sat; smoothing his skirt; he even had the voice down.

  Even though a part of Allen was only pretending to be Jennifer just to get it over with, another part of him was really enjoying it. Deep down, he didn’t know which side was in control, and the alcohol blurred that fine line between playing pretend and actual enjoyment. As the night went on, Jennifer became more and more a part of him until he slipped into an alcohol-induced slumber.

  Hours later, Allen sat up straight on the couch and slid his feet in front of him. It was early. The morning sun shone into the room and gave it a faint orange glow. He looked at the table in front of him and saw three wine bottles; two were empty, and the other was less than half full.

  He noticed that he was still dressed. He looked down to see the high heels still on his stocking-clad legs and the skirt he was wearing was now even more miniature, as his aggressive sleeping habits had bunched it up into ball at his waist. It left nothing to the imagination; his panties were fully exposed. He grumbled, his eyes half-open and his head full of cobwebs.

  “Morning, sleepy head.”

  He turned to see Jessica in the kitchen. She was drinking some coffee and reading the paper.

  “Get up and get out of my clothes already. If you wear them any longer, I’m gonna have to replace all your clothes with new ones.”

  “All right, all right. Don’t get your panties in a knot—”

  “Like yours are?” she interrupted, laughing.

  Allen scowled. “Very funny.”

  Jessica stepped out of the kitchen and helped him up off the couch, leading him into her bedroom.

  “Now, don’t ever try to sneak into my clothes again. There’s still a lot of ‘womanhood’ that I didn’t teach you last night, and if I catch you again, I might just take you to the mall to go shopping while dressed. Then we can hit up a club and find a couple of horny guys and—”

  Allen put his hands in the air, waving her off. “Okay, I get it. I’m sorry. Just please keep this to yourself. I beg of you.”

  Jessica smiled and nodded as Allen removed the last article of clothing and left her room, not wanting the conversation to go on any further. Being with her last night had been torture. He had developed feelings for her in the time he’d lived in the apartment. But instead of getting undressed together, she had dressed him up. It was all backwards.

  Yet for some reason, Jessica was more friendly with him when he was dressed as a girl than how he had seen her act when she would chat with guys. Could that be the reason she was still single? Was Jessica a lesbian?

  No—just because she didn’t have a boyfriend didn’t mean she was into women. She probably just had standards that no guy had met.

  He closed the door to his room and fell onto his bed.

  Summer flew by and the days got shorter. Fewer people visited the beach outside Allen’s apartment, and nothing had happened since his night with Jessica. Allen was nervous whenever Susan would be gone for a long periods of time. He wondered if Jessica would try to get him to dress up, but she had been acting like nothing ever happened.

  After the first couple of weeks, his paranoia subsided and he just enjoyed himself. Work had been good—busy, but good. The bigger paycheck was always nice and living frugally had helped fatten up his savings. He took a week off in mid-June to go on vacation with his family, but other than that, he had been living his life day by day, enjoying the freedom.

  While he enjoyed the many beach trips, especially the ones with Jessica and Susan, Allen found that he had a hard time keeping his eyes off of their bikini-clad bodies. Even so, he was looking forward to winter. The rain and the cold was always his favorite weather.

  Recently, Jessica and Susan had been having private conversations, and whenever Allen came by, they would either stop and act like nothing was going on or move somewhere else. He tried eavesdropping once or twice, but afraid of what they would do if they caught him, he eventually gave up and just ignored it.

  At first, he feared that Jessica was sharing their secret with Susan, but every now and then, he managed to pick out keywords; words such as “party,” “drinks,” and “Halloween.” The mention of the fall holiday squashed any fears he had of his secret being shared, but it also replaced the old fear with a new one.

  Allen panicked. The last time he was at a costume party was many years ago. Halloween was never a big deal for him, as he was never a partier. Every year he would just have a movie marathon and play video games. He was an introverted man, not a big fan of loud, crowded parties full of strangers.

  On the first of October, Jessica and Susan decided to bring Allen into the conversation. It turned out that Halloween was their favorite holiday of the year, and they always had a huge costume party to celebrate it. They were still hashing the details, and they had wanted to surprise him.

  Susa
n filled him in on what they had decided so far.

  “Okay, so every year, we host a Halloween party, and they're always lots of fun. Last year’s was so good that we got mentioned in the paper! It’s gotten so big that we’ve had to hire bouncers to keep uninvited guests out. It gets pretty hard core and you have to have a costume if you want to attend. And trust us, you’ll want to be here.

  “So, my advice would be to start coming up with your costume now. There’s really only one rule for the costume: you can’t tell anyone what it is. Other than that, go all out. There’s nothing you can’t dress up as, but you gotta be covered in certain areas.”

  “Yeah, keep it clean, buddy,” Jessica said as she smiled.

  “Sounds fun. I'm in,” Allen replied. Even though he had no idea what he wanted to dress up as, he still wanted to be there. It would be a chance for him to impress Jessica.

  He had been so timid and withdrawn out of fear of her knowledge of his crossdressing that she would probably just look past him without giving him any consideration. He needed to step up his game, impress and wow her, or else the opportunity would pass him by.

  It didn’t take long for him to come up with something; it hit him like a truck when he saw it. Even though he’d never made another attempt to dress up in the company of Jessica, nor did he purchase his own items and do it on his own time, that fetish of his still existed in his mind.

  The internet is a vast and open ocean and it wasn’t hard to find all sorts of transgender-themed sites. Allen had always been a fan of Japanese anime and manga, and his discovery of the many artists who put out series on those topics was a gold mine. One of them in particular had become a recent favorite for him. After reading it, he decided he was going to dress up as a “Playboy Bunny girl,” similar to the ones that the Japanese seemed so fond of.

  There had been many Halloweens where he had thought about dressing up as a girl, as it was the only holiday where it was socially acceptable to crossdress. Jessica and Susan were too obsessed with their costumes to care about what he was doing; they both seemed to think that he would come up with some lame costume. On that day, they would be in for a big surprise. It would take courage and confidence to pull off that costume, exactly the kind he would need to woo Jessica.

  The weeks went by. Slowly and quietly, Allen collected the necessary items for his costume. He didn’t want to give away any clues, and it seemed that the ladies shared the same philosophy. As a result, October was awkwardly quiet, even with all the party planning.

  The sun was shining brightly in his room when he crawled out of bed on Halloween day. He had all the parts to the costume and kept them hidden and separate. Jessica and Susan were already up and decorating the place, as well as triple-checking that everything was in order.

  The party wasn’t going to start until sundown, and they all decided to have a pre-party celebration with just the three of them in their costumes. Allen had until three-o’-clock to get ready. He got out of bed, went over the steps of getting the costume together in his head, and the headed out to the kitchen to get something to eat.

  “Morning, Allen,” Jessica said. She was standing on the couch hanging decorations from the ceiling. “What do you think?”

  “Looks good,” he replied.

  “You excited for tonight?” Susan asked him. While Jessica was balancing on the couch, Susan was darting around in the kitchen. The sink was full of dishes and stove and oven were both in use. He had offered to help many times throughout the month, but they insisted on doing it themselves. The only duty they had given him was carrying groceries up to their apartment from the parking garage underneath the building.

  He nodded his head in reply and watched her move around the kitchen. “Are you sure you don’t need me for anything?”

  “I hope you don’t have a lame costume,” Jessica said, ignoring his offer.

  Allen sighed and tiptoed around the kitchen, doing what he could to not be in Susan’s way. Then he finished eating and headed back to his room. He knew it was going to take a while to get ready. Fortunately, he had all the time he needed.

  He undressed, threw his clothes into the hamper, got on his hands and knees, and reached under the bed, retrieving a large suitcase. Before opening it, he locked his door, making sure neither of the ladies tried sneaking a peek at his costume. The moment would be ruined if they saw it before he had finished getting dressed.

  He unzipped the suitcase and removed its contents. When it was empty, a makeup kit, brunette wig, set of false nails, body shaving cream, feminine razor, and theater glue lay across his bed.

  The next item was a wooden box. Inside was a pair of realistic silicone breasts. Allen had special ordered them off the internet, making sure the color of the falsies matched his own skin color.

  Leaving the items on the bed, he opened his closet door. Hidden inside a suit protector was a typical suit, but beneath that was another suit protector. He removed it from the closet and carefully set it on his bed next to the other items.

  Inside the hidden container was the red bunny outfit. The satin material was smooth and soft in his hands. It was a one-piece costume with a built-in corset. On the back of the garment, right where the lower back would meet the ass, was a large white bunny tail. The hard part was going to be hiding his manhood.

  He opened his sock drawer and pulled out the pair of black pantyhose stuffed into one of the socks. Then he removed the last items from the suitcase: satin bunny ears, a bowtie, and matching cuffs.

  Grabbing the lotion and razor, Allen made his way into the bathroom and took a long, hot shower, shaving off all his body hair and any trace of his facial hair. He got out and dried off. The feeling of the towel on his smooth hairless skin was a new feeling that sent chills down his spine. He threw the towel aside and headed into the bedroom to get dressed.

  The clock on the wall was nearing two-p.m., meaning he had only an hour to get ready. In the quiet of his room, he couldn’t hear any signs of Jessica or Susan in the living room. They’re probably getting into their costumes, he reasoned.

  Standing naked in his bedroom, Allen held the final piece of the puzzle in his hands: the answer to the question, “how would he pull off being a female if he had a bulge in the front of his costume?”

  It would be different if the party he was attending was put on by the LGBT community and no one would think twice of seeing a woman with a bulge in her panties, but for this party, he needed to hide it. After searching high and low, he finally found a site that created realistic, false vaginas designed for the transgender community. The item he had bought not only hid his manhood, creating an authentic—not to mention fully functional—vagina, but also contained pads for reshaping his hips and ass.

  Stepping into the garment, Allen pulled it up to his waist. He slid his penis into the sleeve which connected to a tube, allowing him to piss like a woman. The way it hid it created a space for the penetrable vagina. The thin, flexible material perfectly matched his skin color and went on without a hitch. Looking in the mirror, he couldn’t help but laugh at the sight of his new female organ, curvy hips, and bouncy butt.

  With the bottom half of the illusion taken care of, now came the top half. He applied a thin layer of the glue to the false breasts and pressed them to his chest. After holding them in place for more than a minute, he released them. Testing the realism, he bounced and twisted his body, watching as the breasts jiggled. He watched his reflection squeeze and fondle the tits. While one hand played with the breasts, the other explored his nether regions. While not moist, the fake vaginal cavity was warm and the material felt real—to his limited knowledge, at least.

  Hurry up and complete the transformation! his mind demanded in an effort to push him along. Ever since deciding to dress up in this costume, he had longed to see what he would look like in it. He remembered what he’d looked like when Jessica had dressed him up months ago and he wanted to replicate that as best as he could.

  The pantyhose came
next. Carefully, he pulled the fragile nylon hose up his legs. The top went above his waist to his belly button.

  When the material was on straight and even, the costume followed. Allen grabbed the red satin outfit and stepped into it, pulling it all the way up. His breasts rested in the cups of the costume and the panty rested inside his crack, giving him a tiny wedgie. If it wasn’t for the pantyhose, then it would have ridden up his bum like a thong.

  He gazed at his reflection in the mirror and saw that he had a genuine woman’s body. There was no bulge in the crouch, and the breasts looked perfect. The corset pulled his waist in, and combined with the padding in his hips and butt, it gave him the hourglass curves that the bunnies were known for.

  I think you might’ve gone with too slutty of a costume, he thought to himself, playing out some scenarios in his mind. All of them included drunk guys getting way too friendly. It’s too late; there’s no going back now, he decided. If drunk guys hit on me, I’ll just laugh and play them off.

  There was a tightness in his crotch, and seeing his new sexy body didn’t help. His groin ached as it tried to harden. Allen looked down at his new female crotch. He knew he was erect, but the transformation garment did its job. His attention turned away from his dick and back to the costume, and grabbing the remaining items, he headed into the bathroom.

  In the weeks leading up to Halloween, he had purchased a complete makeup set. Late at night when everyone else was asleep, or during the days when he had the apartment to himself, he watched tutorials online and practiced his makeup application. After remembering the crappy job he did and how good his makeover from Jessica was, he wanted it to be flawless. Fortunately, both of them were gone often, which gave him time to practice putting makeup on.

  Finishing up with red lipstick that matched his outfit, he grabbed the wig and put it on. Satisfied, he looked at the clock to see that it was almost three. He heard a scream in the hallway. It was Jessica and Susan, both loving each other’s costumes. He put on the matching red nails and left the bathroom.