Two Skirts are Better than One

Thank you so much to my editors for taking my messy ideas and turning them into something that you can read and enjoy.

***I have had several people tell me that my stories are a little bit too slow. To accommodate those readers, I have written this story at a slightly faster pace than many of my other stories. I do not for one minute think this is the speed at which two people would meet, discover something new about themselves, and then act on that discovery. This story is entirely a work of fantasy. That having been said, if this has happened to you then I am so happy for you. It took me 20 years to find my soul mate. Please let me know in the comments below what you think of this story and the new pace. ***

It was a Friday afternoon and I was in my apartment. It had been a long stressful week. I decided to relax alone. I had planned to take a bath, put on some classic jazz, and have a glass of white wine or two. Life and one of my younger sisters had other plans.

My name is Aaron Cross by the way. I am 24 and I still live with my parents; three older sisters, Daphne, Penelope, and Opal, and my one younger sister, Sophia. I know what you're thinking. This guy is 24 and he still lives at home? What a loser. But hold on and let me explain. You see my parents own an apartment building and so each of us, my sisters and I, have our own apartment and pay our own rent. Except for Sophy, she's not old enough to live on her own yet. The rent is reasonable but naturally, we are also required to help maintain the building's upkeep, the grounds, and in my case, do the books for our parents.

I asked my mother about our family history once and she said that we were Mediterranean. When I asked her to elaborate on that she said we have ancestors in our family from pretty much every country around the Mediterranean. As a result, my skin is a nice hot chocolate color. I have jet black hair which I wear tied in the back and brown eyes. I am only 5'4 and I am pretty skinny. When I was younger, I wanted to grow one of those big Zeus beards. After a year of trying, I barely managed a pencil mustache and gave up.

I work full-time, remotely, as a call center representative for a local life insurance company. I am in quality control, which means I spent most of my day listening to calls and evaluating the other employee's customer interactions. How I score people plays a big role in whether they get a promotion, a raise, or a pink slip. As you might have surmised that does not make me very popular with some employees. The fact is, I have only one real friend at the company and his name is Harry Gim.

Harry is a Korean copy of me. He has my build, hair color, and height but has short hair and is only 20 years old. I didn't like Harry at first. He followed me around like a puppy. He was constantly asking questions or trying to please me. It was so annoying. Then we all got sent to work remotely and I found that I really missed him. Thankfully we started a private chat and I found out over time he was living with his parents only 10 blocks from where I currently reside. Don't judge him too harshly for living at home either dear reader, rent is insane right now. I know what my parents charge non-family members.

I had my bath, half a glass of wine, and moved to my guest bedroom to begin the activity that relieves my stress the most. Putting on women's clothes. I have been wearing woman's panties pretty much full-time since I was 12. I stole a pair of my older sister's, I'm not sure which one, and tried them on. They felt so much better than mine. I mostly wore my sister's hand-me-downs until I got the courage to buy some for myself. When I was 16, Daphne caught me in one of her nightgowns. I thought I was dead. To my surprise, she was cool about it and became my confidant.

She took me under her wing just as she had Penelope and Opal, and taught me a lot about clothes, and makeup. I am not sure who taught Sophy how to dress but it was not Daphne. She even made some suggestions on how to handle boys, if I ever decided I liked them better than girls. She always likes to plan at least three steps ahead.

That is probably why she is so good at chess. She was even sneaky about showing me new stuff too. She would show Opal a new way to do her hair or apply new makeup when she knew I was around and could watch from a distance. I love my big sis.

She also covered for me a couple of times when I almost got caught. Mom would see new panties in the wash and ask, "who's are these?" Daphne would always claim them and give them back to me later. Once my dad saw one of my dresses in my laundry basket and Daphne said it was hers. Now that I think of it though, I never did get that dress back and Daphne wore it a ton. Could she have planned that? See what I mean about her always thinking ahead?

After my bath, I put on my favorite cream panties and matching thigh highs. Over that went a green and blue plaid skirt. I put on my bra and put in my size B breast forms. Then I completed my schoolgirl outfit with a simple cream blouse that matched my stockings and panties. Truth is, I have a weakness for schoolgirl outfits. I have a dozen different ones. I finished my makeup, less is more, my hair, and simple braided pigtails and went to lay down on the couch. I was listening to Dave Brubeck play Take 5 when I heard a knock at my door followed by my friend Harry's voice calling out, "Aaron. It's Harry."

I froze. What the hell was he doing here and how the hell had he gotten in? Building security was top-notch. The answers to both of those questions were expected and forthcoming. KNOCK, KNOCK, KNOCK. "My friend got me an advance copy of Star Blazer 2202. I knew you wanted to see it as much as I did, so I came right over." Harry paused, "Sophy said you were home and buzzed me in."

Two things went through my mind at that point. First, I was so psyched that Harry's friend had come through. This friend (air quotation marks), had promised much and delivered nothing over the last year. I was honestly not sure if this "friend" was not of the imaginary variety. Second, despite being told a million times to never buzz anyone in, Sophia had once again buzzed someone in without checking first. I was going to kill her.

Maybe he would just go away. I waited a few minutes in silence. Knock, knock, knock. "Come on man let me in," Harry called.

Well so much for that idea. Then things got worse. Harry started to sing. "Where off to outer space. To save the human race...If you don't let me in, I will keep singing until you do."

Maybe he was bluffing. He went through the theme song twice. He was not bluffing. You had to give the guy credit. He is persistent. It was one of the many things I found annoying at first but came to accept and then respect him as I got to know him. He's such a cute little nerd, I thought with a smile.

I could not believe I was going to open my door dressed as a schoolgirl, but I had no choice. My neighbors were undoubtedly minutes away from calling my parents to complain about the off-key noise or to report something dying in the hallway and then I would be outed to everyone on the floor. I opened the door before he managed to start over and pulled him into my apartment. I then checked up and down the hall as if I was a secret agent or something.

To say that Harry had a look of shock on his face when he saw me would be totally incorrect. It was more like shock, fear, dismay, and a sprinkle of jealousy all wrapped up in a nice confusion burrito. I had to give him credit. He recovered rather fast. His brain swiftly narrowed down the possibilities of who I could be to one of two, home invader or my, that is to say, Aaron's, girlfriend. Since I was not dressed in black, wearing a mask, or carrying a bag marked 'loot,' he went with the second option. "Who are you?" Harry took a step away from me and the front door, "Aaron never told me he was seeing anyone."

I was filled with pride at the fact that Harry thought I could get a girlfriend like me. I mean female me, not male, me. I do not want to toot my own horn but I make a pretty attractive woman. Further proof to me that I undoubtedly should have been one in the first place. As a man, I am quite plain, to say the least. "I'm not Aaron's girlfriend," I said.

The girlfriend option thus eliminated Harry went with the only other option left to him. "Where's Aaron? Is he OK? If you have done anything to him, I'll call the police." He pulled out his cell phone.

I was so touched by Harry's concern for my well-being. I mean, I knew we were friends. I would even say best friends, but the guy was standing up to a presumed intruder. A very short, skinny one, but an intruder all the same. I could not help but smile at the big lug. The fear in his eyes and the fact that he found his phone brought me back to reality. There was nothing left for me to do but confess. I put up my hands in a peace gesture and said, "Harry, it's me." When he still looked confused, I added, "Aaron."

Harry didn't look convinced. My ego was about to explode. I mean really, I had done such a good job of dressing as a woman that my best friend and co-worker didn't recognize me. Damn, I must be better at this than I thought. I smiled again, "No really Harry, it's me."

Harry still didn't look persuaded. "Your name is Harry Gin, we have worked together for two years, your employee number is 56478 and you are addicted to orange soda and ham and cheese hot pockets."

Harry seemed to be coming around but was still not sure so I pulled out the big one. The fact about Harry that only I knew. "Last year, you accidentally deleted the check request folder. I was the one that stayed up all night with you reconstructing it before anyone noticed."

Harry gasped. "Aaron? Is that really you?"

I couldn't help it. I gave him a, well-duh, look. "Yes, Harry it's me."

He asked the obvious question, "Why are you dressed like a schoolgirl?"

I had never been asked that particular question before, but I had asked myself why I liked to dress as a woman many times. I had come up with several answers over the years. I'm in the wrong body. Men's clothes are boring. Woman's clothes fit me better. It's a good way to freak out my family. I just like the way they feel.

I gave him a compilation of them all. "I like to dress as a woman..." I started slow and a little shaky, then I machine gun answered him, "because they seem to fit me better. I love the way the material feels. Sometimes I think I was supposed to be a woman."

I took a deep breath. Harry just stood there looking at me. Then he said the most random thing he could have possibly said, "Well, we are all girls, to begin with. Then something activates a gene in us and we become boys. At least that's what they said in Jurassic Park."

Thankful for the distraction I argued back, "Yes, but they were talking about dinosaurs and should we really put any faith in facts provided by a movie called Jurassic Park that only showed us one dinosaur that was from the Jurassic era."

"Good point," Harry agreed, looking sheepish.

We both laughed. I never realized how in sync Harry and I are. He kept looking at me and I just stood there letting him. I'm not sure why but it was kind of nice. I tried to read his mind. I started to turn in place. I'm not sure if that was what he was thinking or if I'm just a good guesser, but in either case, when I came around to face him again, he had a huge smile on his face. I blushed.

Finally, he seemed to snap out of some spell and said, "Don't take this the wrong way dude, but you are one of the most beautiful women I have ever seen."

My face flushed again. "Is there a wrong way to take that?" I asked, then remembered my manners. "Thank you, kind sir," I said curtsying.

It was Harry's turn to redden. "Do you dress like this all the time?" Harry asked.

"No," I answered a little too loud. Harry cringed. "Sorry," I apologized.

"Why not?" He rubbed his foot on the back of his leg like in the old romantic comedy movies. How in the seven vermillion hells had I ever not noticed how adorable he was?

I pulled him down onto my sofa. I knew that the soundproofing in the walls was not CIA level but it was also not paper thin. My parents run a respectable apartment building. Still, caution is the better part of not getting caught crossdressing. "Because Harry," I said in a soft conspiratorial tone, "Aside from my sister Daphne and now you, no one knows I like to wear woman's clothes."

Keeping his voice equally low Harry gave me a disbelieving look. "I must respectfully disagree," he said in the same tone he usually used when we debated which rebel starfighter was the best, "you don't think Daphne told Penelope and Opal?"

I stared straight ahead at the wall. That thought had never even occurred to me. Harry was right. My three older sisters didn't keep anything from each other, so for Daphne to not tell Penelope and Opal made no sense. Now that I thought about it longer, that she'd told them made far more sense given that they seemed to be totally ignorant to my crossdressing. They would have normally figured it out in short order. There was also the sheer number of hand-me-downs I had received over the years from Daphne that supported his theory. Surely not all of the clothes could have come from one person.

I began to wonder who else Daphne might have told. Mom and Dad sprang to mind. I had to smile. Would they have told Sophy? If they had told Sophy, would she have remembered? I love my little sister. Really, I do.

"By George, I think you're right," I said in a very bad English accent.

I hugged him. Good grief he was soft, but also warm. He smelled good too. Unlike some other men, who seem to think showers are an optional thing. Harry smelled of lavender and mint, two of my favorite scents. I was about to let go of Harry when he held me tighter.

I made up my mind that I was not breaking the hug for anything short of a fire alarm. Apparently, he had made up his mind to do the same thing. This gave me a chance to reorganize my thoughts. Did this mean I was gay? Did this mean I was bi? Had I ever wanted to just hold a woman like this? The answers I gave myself when I was completely honest with myself were; yes, maybe but probably not, and never, not even once.

We just sat there on my couch holding each other. I was beginning to wonder how long we could go without water when he said, "I never realized how big your chest was."

"They're inserts. They go in my bra." I explained.

"Wow, they feel real...nice." Harry caught and corrected himself to be more polite. He is so sweet. I wanted him. I wanted him bad. I could not believe how much.

"I know," I wiggle my chest a little while still holding onto him. Then I decided to up the ante and put my head on his shoulder.

Harry held me tighter and then let go a little but not completely. "Your right that shirt does feel soft," he commented.

"I know, right." I moved my head to his other shoulder, "You should feel it next to your skin."

What the hell was I saying? He's a friend. He's a co-worker. He's not gay. At that moment I didn't care.

I had expected him to release me and then run his hand up and down a sleeve. Instead, while still holding me, Harry leaned in and rubbed his cheek against my shoulder. Points to Mr. Gin for once again thinking outside the box. He was always doing that.

What Harry asked next was more than outside of the box. It wasn't even on the truck the box was on. He moved his head to my other shoulder. I am not sure which was shaking more him or his voice. After a minute he took a deep breath and in a very nervous tone he asked, "Do you have one that will fit me?"

I broke the hug and just stared at him. I was suddenly very excited. My breathing was fast, my blood pressure was skyrocketing and my throat felt like I had swallowed a dozen cotton balls. Harry must have thought he had said the wrong thing as he looked like he was about to throw up. Weary that I was about to fall into a too-good-to-be-true trap I asked, "So, you want to try crossdressing?"

I don't think he could have gotten any more nervous than he was at that moment. "I guess that depends on whether you are into crossdressers or just cross-dressing," Harry answered and asked. Then he took a deep breath and went on in a whisper, "I like crossdressers."

The 1812 overture started to play in my head and my heart expanded to twice its normal size. Cautiously I said, "I'm into people that make their own decisions and don't just follow others."

"Honestly, I have always wanted to try it," Harry argued and pleaded a little with me, "but I never had access to the clothes or someone who could help me. Trying it with you would be a fantasy come true."

I thought about what to say next for a minute. "Let's back up, I will be more than happy to help you try crossdressing, Harry."

I had not answered his question and we both knew it. He wanted to pin me down, metaphorically, and I couldn't blame him. I wanted to be pinned down by him literally. He asked, "so, you would not be opposed to dating another crossdresser?"

I figured for being so honest with me he deserved a reward. I leaned in and for the first time in my life, I kissed a co-worker. When I pulled back, he was still frozen in mid-kiss. He opened his eyes and then just zoned out a little.

"Naturally people are attracted to people who are similar to them, but I like you Harry so...," I paused to let my admission sink in (Harry beamed), "if it turns out you like cross-dressing that would be great. If you don't, I don't see that as a deal breaker. I would still like to explore a relationship with you."

Harry started nodding his agreement. He liked me. I mean he really liked me. I could not believe I had never seen how much he liked me. I mean it was as obvious as a stop sign now. His smile was so wide I wanted to check to see if it went around the back of his head under his hair.

My heart was still racing. I didn't want to ruin the moment but I had to know if his offer to try cross-dressing was just to ingratiate himself with me or not. I was so nervous as I asked the next question, I had to hold onto the couch cushion. "So, if you don't want to wear dresses that's OK. As long as you don't mind me wearing them. I would understand."

Harry didn't, "I wasn't kidding about wanting to try on dresses. I have even thought about doing more than that but, I figured, baby steps." He put his arm around me, "I only hope I will look a tenth as hot as you."

I snuggled in close to Harry. He took a deep breath. I was so excited to hear what he had just said. In less than an hour I had gained a potential boyfriend, a potential crossdressing buddy, and the prospect of a weekend of binge-watching the new Star Blazer. I checked my pulse quickly to make sure I was still alive. I sat there and let him just ponder what he wanted to do next. I was about to get up and put in the DVD when he said, "How do we get started?"

I got up as planned but then turned to help him to his feet. I took him by the hand and lead him to my bathroom. He was still wearing a smile but now it was a cautious one. I reached into the cabinet and pulled out tweezers, shaving cream, my personal hair trimmer, and a couple of ladies' razors. I set all of these items on the sink. I took the clippers and toggled the switch on and off a couple of times. It made a very satisfying buzz, buzz, buzz sound effect.

"We start by getting you naked." He looked a little scared, "then we operate."

Less than an hour later Harry was standing before me, naked and hairless save for what was on his head. His legs had taken no time at all and after a whole lot of promises that he would like it he let me shave his cock, balls, butt, and armpits. To be honest, the part that had taken the longest and I think hurt him the most was his ears, eyebrows, and nose. He was a real trooper though and only cried a little.