The next few years of my life may have looked normal on the outside, but inside was a mess. Every so often, my mind would be drawn back to that time I spent in my sister’s dress. Then the urges would strike again. Why was this happening to me? I tried looking it up online, but time was limited as I only had the family computer and some at school to work with. Privacy was hard to come by. Still, even when I did get the chance to look, I never quite knew what to look for.

Ultimately, I just kinda figured I liked crossdressing. Just being a boy in girls’ clothes, it was fun. Not to mention, I discovered other sorts of excitement from it. But that was never really the point. It sort of just became a hobby. There was nothing wrong with that, right?

As I grew older, I had more opportunities to be home by myself. Mom and dad would go out and instead of asking Tara to watch me, they said I would be fine on my own. Tara would go out with her friends and since I didn’t really have a lot of those, I just stayed home. Which was fine with me, I didn’t mind. These were the times when the urges were the strongest. I’d sneak into Tara’s room and, depending on how much time I would have, the fun would begin!

By now, I knew not to be so blatant about what I did. Rumors started going around the house about things going missing or being moved. I joked there must be a ghost or something, but really, I knew the truth. I was the one moving things, be it my sister’s or even my mom’s clothes. I was living for the thrill of this! Still, I had to be careful. I didn’t want anyone to know about this! My secret joy, my secret shame. 

Today was perfect. Mom and Dad were going to a meeting at their church. I was never much of a believer, so I’d asked to stay home. Tara was off to a sleepover at Samantha’s place, meaning I had the place to myself until late evening. Dad even left me $20 for a pizza! This was gonna be a great night! Once I was sure everyone had left, it was time to put the plan into action. I once again found myself at the threshold of my sister’s room. “Well,” I thought, “here goes nothing!”

I opened the door and went inside. Just as pink and girly as always. Somehow, I’d grown to like that color. Something about it spoke to me. For now, I went in and went straight to her closet. I wished she had more dresses, but she wasn’t really the dress type. Still, she had a few for special occasions, as well as a bunch of skirts. Sadly, I had outgrown the dress I wore the first time. Especially now that puberty was in full swing. I had gotten taller, my shoulders broadened and developed hair all over my body. I didn’t mind it too much. Still, learning to shave would be a pain. How I longed to be slim and feminine like my sister. Then I could wear any dress I pleased!

Who was I kidding though? I was a boy, I’d always be one. The reality was, I’d never actually be pretty. No matter how much I wanted to, how much I dreamed of it. In the meantime though, maybe I could at least pretend. I looked around and luckily, she had one dress that would somewhat fit me. It was a simple blue dress with a white ribbon across the middle. It was her church dress. Mom and Dad insisted we dress up nice for church, so she had that dress for it. I was stuck with a button up shirt and dress pants. At least they didn’t force me to wear a tie, that was the worst! It always felt like it was choking me, even if it was just a clip on.

I took the dress out and laid it on the bed. I would need more than just this, so I got to work seeking out the rest of the clothes. I hoped she wouldn’t notice if I borrowed some of her underwear, especially if it was from the dirty clothes hamper. I also grabbed a bra and some socks to stuff it with. Finally, one of her nice pairs of shoes. They didn’t quite fit, but I’d squeeze into them anyways. With everything gathered, it was time to get to work.

Once again, I stripped off my clothes. I quickly got the panties on, but struggled with the bra. After I had it hooked up, I stuffed socks inside. I slipped the dress over my head and stepped into the shoes. It felt good being dressed up again like this. Luckily, I had time to kill. So, I sat down at the vanity and got to work. I had gotten decent at putting on makeup by now, though the opportunity to use it was rare. I was far from an expert, but I figured I had the basics down. Eye shadow, mascara, foundation, blush and lipstick, those weren’t too difficult to do. When all was said and done, I didn’t look too bad! I still looked like a boy, but I was at least somewhat pretty!

From here, I didn’t really have a plan for what to do next. I just wanted to relax and play in this dress. I could pretend I’m a girl and be pretty, which occurred to me was what I wanted most. It was a thought that had been lingering in the back of my mind since I put on that first dress, I wanted to be pretty. I was a bit jealous of my sister, how she effortlessly glided through this. Being pretty came naturally to her and to other girls! Why couldn’t it be that easy for me? Guess I was stuck with that, being a boy and all.

As I played around, I thought I heard something. Was that a car door? I quickly took a peek out of the window. “Fuck!” I yelled, surprising myself.

It was my sister! What was she doing back? That was Samantha’s car she just stepped out of, why was she here?! No no no, this wasn’t good at all! I had only just gotten dressed up, I had to take it off now! In a panic, I kicked off the shoes and threw the dress off. I could hear Tara downstairs now, damn it she was moving fast! As I tried my best to take off the bra, the door opened. She took a couple steps in before stopping dead in her tracks, staring me right in the eyes. I must have looked like a deer caught in the headlights, as her jaw dropped to the floor.

“Michael,” she started, disbelievingly. “What the absolute fuck are you doing?!”

I tried to talk, to come up with some excuse. My mind was racing. What should I say? What COULD I say? But it was as if I had forgotten how to talk. My lips moved, but no words came out. Only desperate sounds.

“I asked you a question! What the fuck are you doing in my clothes?!” She was clearly much angrier now. This was getting worse by the second! Could I hide? No, too late. Run? I was in a bra and panties, where would I go? Besides, she was bigger, stronger and faster than me. I was a pathetic, little nerd while she was an athlete, a member of our school’s track team. I shrank away, trying to put at least a little distance between us. I was scared, what was she going to do to me?

“Speak up now, or I’m telling everyone at school that my brother is a fucking little sissy boy! Mom and Dad will have to know too!” She was screaming by now, I flinched at the sound of her voice. I was clearly screwed at this point. This was too overwhelming, the tears started to flow as I broke down sobbing.

“Please! Please don’t tell anyone!” I begged, the desperation clear in my voice. “I’m so sorry! I, I don’t know what came over me! I just, I was curious! That’s all! This went further than I expected! I, I just…”

“Can the excuses! You and I both know this ain’t the first time you’ve done this.” My mind was almost empty at this point, I was so scared. I fell to the floor, shaking and crying. I couldn’t hold anything back at this point as my breaths grew harsher and more unsteady. She looked down at me, realizing she had pushed too hard. She took a deep breath before sitting down next to me.

“Hey now,” she said in a much calmer tone. “Easy, take a deep breath. In and out.” I followed her instructions. It was shaky, but I tried to take a deep breath.

“That’s it, much better. Keep taking deep breaths.” Her cell phone suddenly rang. She pulled it out and flipped it open. “Crap, that’s Samantha. She’s waiting outside, I gotta take this.”

She answered her phone, though I could barely make out what she said. “Hey girl! ... Yea sorry, can you just hang tight for a bit? Something came up and I gotta deal with it. ... Don’t worry, this shouldn’t take too long. ... Yea, ok, bye bye,” she closed the phone. She looked over at me and sighed.

“Look, Michael, I’m sorry I freaked out on you like that. I just don’t understand, why are you wearing my clothes like this? Sneaking around behind my back, that’s not okay. You understand that, right?” She sounded a lot more calm now. Still, between my sobs, I nodded.

“Then talk to me. Tell me why you’re doing this. I’m your big sister, you can tell me anything. Forget what I said before, this can stay between us. Just talk to me. What are you getting out of this? Does it make you happy? Do you like looking this way? I guess what I’m really trying to ask is, do you want to be a girl?” Her intent seemed genuine here, yet I was still afraid.

“No!” I quickly yelled, startling her. “No, I don’t wanna be a girl. I don’t know what I want. I just like doing this sometimes. I can’t be a girl, I’d know if I was one, wouldn’t I?” I looked up at her. She just sighed again.

“Honestly Michael, I don’t know. I haven’t met anyone like this before at all and either you or mom are always hogging up the computer. I couldn’t tell you. If you’re gonna keep doing this though, shouldn’t you get your own stuff?”

“What? No no no, I can’t! No way! No I’m, I’m done. I swear! I’ll never go through your closet or take your stuff again, I promise! I’ll never wear girl’s clothes again, ever!” If I’d believed in God, I’d have sworn to Him right there and then. She gave me an inquisitive look, like she was trying to see if she should believe me or not. We just sat there for what felt like ages until she spoke up again.

“If you’re sure about that Michael, then fine. Let’s get this stuff off of you and get you cleaned up. This will stay our little secret, for now. But if I catch you again, if I even get the slightest whiff of you wearing my stuff again, I’m telling Mom and Dad. Are we clear?” She offered me her hand, to make the agreement official.

“Yes Tara, crystal clear.” I nodded and shook her hand. The tears slowly stopped as she helped me to my feet. She helped me with the bra and turned around while I got dressed in my own clothes. She took a wipe from her vanity and used it to wipe the makeup off my face. When she was done, I was back to plain old me again. Which honestly, I didn’t mind. I was fine being a guy. I liked my clothes just fine. Maybe I just wanted to see how the other half lived or something. Whatever, I promised and now it was time to put crossdressing behind me.

Tara got all the clothes I wore into the laundry, she’d do the load herself later. After escorting me back to my room, she bid farewell once more, got the swimsuit she’d come for, and went back to see Samantha. She was trusting me not to go into her room again. I’d make sure that trust was well placed. I decided to load up a game on my PlayStation 2 for now. Still, the feeling of fear deep down in my gut never really went away. What if she lied? What if she and Samantha were laughing at me right now? What if she told Mom and Dad after all? I could hardly concentrate on the game at all, these thoughts were so distracting.

I felt sick to my stomach for the rest of the night. I ended up getting a pizza after all, but I barely nibbled at it. Soon Mom and Dad came home and treated me like everything was normal. Did she not tell them after all? I played it up like everything was normal, I just wasn’t that hungry. Mom was concerned at first, was I coming down with something? I reassured her I was fine, even if I wasn’t. They could never know what happened today, and I hoped it would stay that way.

After that day, I thought I was done with crossdressing. It did stay that way, at least for a while. Still, the urges nagged at me. I wouldn’t let them win, I didn’t want to break my promise to Tara. Soon enough, I’d find a new way to deal with them. But that’s a story for another time.

Chapter 2 End