Josephine

Changes

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It didn't happen overnight. But over time I relaxed into my new freedom.

I started shaving my legs, and I loved the way stockings felt against my smooth legs. One of my lovers taught me how to trim my "bikini" area and encouraged me to do so. Before long I was either shaving or using depilatory cream to denude most of my body.

My sister noticed my bare legs under my robe one morning and encouragingly suggested that I should try the moisturizing cream that she used to help prevent the sort of irritation that shaving could cause.

I began sleeping in a delightfully silky nightie that made me feel comfortable and sexy at the same time.

When my sister wasn't home I would slip into a simple ensemble and walk around the apartment, watching myself in every reflective surface that I passed.

I started to become very comfortable with who I was and the way that I dressed.

I knew that I couldn't paint my nails because of my job, but I began painting my toenails. I figured that if anyone ever discovered them I would say that my girlfriend painted them while I was asleep.

I experimented with different ways to create the illusion that I was curved like a woman under the clothing. I began wearing a padded bra and experimented with different ways to stuff it. I discovered "shaper" undergarments that were designed for women but helped with my illusion.

Feminizing my appearance became the thing I did when there was nothing else to do. And then it became a part of my lifestyle. And the handful of lovers I had at the time all approved. And when she would see some evidence of what I was doing, my sister would remain supportive and make suggestions.

Josephine

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My environment was safe, but I should have seen that it was just a matter of time before my sister caught me all dolled up. Despite all of her support and love, I was still anxious about her seeing me actually wearing women's clothing.

It was late and my sister was out with one of her boyfriends. I had lost track of time and was on the couch watching a movie when I heard the key in the lock. I had become so comfortable with myself that it took me a moment to remember that I was wearing my nightie and cliché candy-striped thigh highs!

Quickly, I hopped up and dashed past the entryway and down the hall toward my room. Out of the corner of my eye I could see my sister and two men and I hoped that neither of the men would recognize me.

As I ran I could feel the hem of the nightie rise up to reveal the ruffled boyshorts I wore underneath.

I quickly shut the door behind me, still hoping that being quiet would allow me to escape.

"Was ... that ...," I heard one of my sister's regular lovers start to say.

"My sister," came my sister to the rescue.

I heard an unfamiliar voice say, "Your sister is pretty hot."

My sister laughed a little and replied, "Josephine. Yeah. Josephine is really something."

I could hear the familiar male voice move across the room saying, "I remember you saying that she was coming out. For a visit."

And there was a pause.

"From what I could see, hot must run in the family," he continued.

"I didn't bring you two back here to ogle my kid sister," her voice was coming down the hall and I could hear her bedroom door open.

"Do you two want to get naked, or what?" She asked with a hint of challenge.

I stayed in my room for the rest of the night with the door locked.

Recognition

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In the morning I waited until I was sure that both men had left, and when I came out for coffee I was wearing my work clothes, even though it was Sunday.

"Going to church?" she asked with a raised eyebrow.

"I, uh, wasn't sure if anyone was still here," I answered.

"Yeah," she smirked. "Because my kid sister went into the bedroom and my kid brother came out. That's about as subtle as Clark Kent using a phone booth."

I hadn't thought of that. That would have been pretty awkward, at least.

"I didn't mean to surprise you like that last night," she apologized. "If I had known what you were doing I would've given you some warning."

"I didn't want to ... be ... indiscrete. I didn't want you to actually have to see me like that," I tried to explain.

"I've known you liked to cross dress since we were kids," she explained.

"That time I fell in the barn"

"As soon as I saw that you had shaved your legs, I realized who had been ruining my good nylons. I'm fine with it. And I was then, too," she continued. "But you know where we were. I was afraid for you. I don't want you to get hurt."

There was silence.

"Let's get this over with so you can stop feeling ashamed of yourself around me," she said putting her hands down on the counter. "I refuse to allow you to live in shame. Lord knows you've been listening to me have little orgies in my room since we decided to live together."

That was an interesting way to describe it, but I indulged myself in the way she reframed the circumstances. I supposed that I could have found my own place by then if I had really wanted to.

"Go back in there and get dressed up again," she commanded. "I don't care if you want to be my brother or my sister or something in between. But around me, you should be whoever you want to be."

I didn't move. I couldn't say anything.

"Go on," she gently nudged. "I'm not letting you have coffee until we get this over with and I can show you that I mean it."

She was serious. I was scared, but I wanted to get this over with too. I knew it was something that I had to do.

"ok," I whispered, and made my way back to my room.

It took some time, but I carefully pulled one of the more comfortable and conservative outfits that I had assembled over the months. I stood at my door for a moment collecting myself. I took a deep breath, opened the door and carefully walked back out into the kitchen.

My sister watched me come down the hall wearing a knee length black skirt, violet long sleeved blouse, opaque patterned tights, and wide heels.

"Mm. Looking good," she casually declared in the same manner she would use any other time I took the time to dress up.

I stood there and let her look me up and down. Then she handed me my morning coffee.

"What do we do now?" I asked sheepishly.

"We have coffee," she stated. "You're no different to me in a skirt and heels than you are in jeans and sneakers."

She sat on the couch and beckoned me to sit next to her. We sipped coffee. She seemed completely comfortable and it put me at ease.

"It looks good. That outfit totally looks like something Anna would pick out," She said.

"Anna went shopping with me. We pretended it was for her and that I was the bored boyfriend," I answered.

"That makes sense. But this isn't how you were dressed last night. When we came in it looked like there was a Suicide Girl running down the hall," she smiled. "You ran by too quickly for them to see anything but your backside, but John and Matt were totally getting as much of an eyeful as they could."

"John knew I was me, though," I asked nervously.

"He figured it out pretty quick, but he still liked what he saw," she said. "He's bi, so ... you know."

That made me a little uncomfortable. I was not sure why.

"So, do you just wear these clothes when you're feeling ... you know, horny? Or do you like to wear these sorts of clothes more generally," she inquired trying to sound casual.

"It was ... a kinky thing at first. But living here, with you, and feeling as safe as you and your friends have made me feel ...," I searched for the words, "... I began to realize that I like dressing like this. I don't know why. It just feels ... nice. Comfortable. It even feels natural, as silly as that may sound."

"If this is how you feel comfortable dressing, then dress this way. I'm completely fine with it," she explained. "And a lot of my friends would be fine with it too. Hell, half of my friends are openly something other than heteronormative anyway. But unless you say otherwise we can keep this a secret. John won't say anything. And most other people, like Matt, don't actually know that I don't have a hot younger sister named Josephine. So it should be fine. We'll make up some story about her so we have the same story if anyone asks."

I felt as if a great weight had been lifted from me. I was incredibly grateful for having such a sister. I grew limp as the tension left my body. I placed my head on my sister's shoulder and quietly thanked her. She put her arms around me and hugged me.

"So ... I looked good last night?" I asked quietly. "I looked ... like a woman?"

"Sweetie, if I didn't know that you were my ...," she fumbled for a gender neutral phrase, "... family, I would have chased you down that hall and done wicked things to you myself. And I can't remember the last time John came so quickly. I think his mind was fixed on that sweet eye candy he caught when we first walked in."

I laughed a little.

"So," she inquired, "when you're dressed like this are you my sister? Or are you still my brother? Do you want me to treat you any differently than I always have?"

I hadn't ever thought about it. It didn't seem right to try to call myself a woman. It seemed like a lie. But I was intentionally dressing like a woman and taking on feminine aspects. But was that what I was doing? It didn't seem like I was acting. Sometimes I felt masculine and other times I felt feminine.

"I don't know," I answered honestly. "I'm a man. I don't want you to treat me any differently. But ... I liked the name."

"The name?" my sister asked.

"Josephine. It's my real name," I explained, "just with a few extra letters."

"Sweet Mary," she mumbled. "How did heteronormative even become a thing?"

I had to look up what heteronormative later. While I was well read and had a pretty broad vocabulary, I was not particularly familiar the language of gender politics at the time.

She rubbed my hair and said, "How about I just keep calling you Jo. It could be a man's name; it could be a woman's name. And if you want me to change that then you just let me know, ok?"

"That sounds good," I said. "Thank you."

It was raining and kind of chilly outside. We stayed in that day and just hung out. It was the first time I had worn women's clothes around someone that I wasn't having sex with. We read and talked and ordered pizza for brunch. I hid in my room when the delivery guy came. But I spent the entire day dressed as a woman might dress.

We even did "girly" things. My sister showed me how to shape my eyebrows to be less bushy and more androgynous in a way that would simply look like my masculine identity was particular about his grooming and appearance. And she put makeup on me. Not a lot. Not whorish makeup. It was just a little eye liner, shadow and lipstick. I had heard of women doing this sort of thing with each other, but had never experienced it firsthand. I remember being surprised at how much I enjoyed it.

Later in the night, she changed into a pretty little chemise and men's boxer shorts to watch a movie. And I changed into the same short, black nightie and ruffled boyshorts that I had worn the night before. But I thought the thigh highs were too much, so I left my smooth legs bare.

When my sister politely asked what was keeping my private parts secure, I pulled up my nightie and showed her the top portion of the high rising shaper thong that I was wearing under my boyshorts. It came up to just below where my breasts would be, if I had them, and helped to shape my waist. The stretchy fabric also pressed my boy parts up against my body and kept them from bulging or falling out of my panties.

She asked if it was uncomfortable, and I told her that it was a little at first but that when I wanted to feel feminine that they really helped me feel feminine.

When I went to bed, I removed my boyshorts and the shaper thong so that it wouldn't be crushing my cock and balls all night and slept in my nightie really knowing for the first time in ten years that there was nothing wrong with me.