(Disclaimer: This is based on experiences I had, though I am adding a bit to cover what my mother's side of the story was, that is based on what I was told happened. It's a long enough story that it will likely cover several posts.)
"Mom, what's it like to be a girl?"
My mother had been working on continuing education material for her job as a nurse when I came over and sat down next to her to utter those words. It was just her and I at home at the beginning of summer; my stepfather was on a business trip for several days, my sister was baby-sitting a pair of kids while their parents were on several days vacation, and my step-sisters were off spending time with their mother. My curiosity about girls had been sparked quite a while before, but I had never been sure how to go about figuring things out. I certainly didn't feel I could talk to my siblings about it, and I wasn't close enough to my stepfather to feel like I could be open about my questions on girls. Up until I asked that question, I wasn't sure what I wanted to know.
My mother stopped her reading and put her book down, thinking quietly to herself for a moment. "That's not an easy question to answer. It's like me asking you what it's like to be a boy. You can't really describe the differences because you only know one side," she explained. She thought about it for a minute more. "I don't know that there is a way to explain what it's like to be a girl or a woman. It's just what I am, it's just something you do." I listened to her, and understood. She felt there really were no good words to use. "Give me a bit to think about it," she finished. I went back into the living room to watch television.
It was probably fifteen minutes later that she came into the front room to talk to me further. "Do you still want to know what it's like to be a girl?" she asked me. I thought about it for a minute. "I guess so," I answered. "Well, if you do, then come upstairs," she said as she turned and left the room.
As I followed her down the hallway and up the stairs, she began to explain her thinking to me. "Like I said, being a girl or woman is just something you do. So, if you want to know what it's like, my best suggestion is that you do it yourself. We'll have you dress like a girl so you can see what it's like." We stepped into her bedroom and she looked directly at me. "So, you get undressed and I'll get some clothes for you to wear. You're about the same size as me, so that shouldn't be a problem." I stood there, not sure what to do. "Get your clothes off," she insisted.
I started to unbutton my pants, somewhat in shock. As I did, I wasn't sure just how far I was supposed to get undressed. My mother began to step over towards her dresser and closet when I asked, "Underwear too?" She stopped and thought for a second. "Yes," she concluded, "you want to try being a girl, not a boy in a dress. So you should be all girl."
I finished unbuttoning my pants and had my shirt off when my mom dropped a pair of panties and a bra on the bed next to me. I hesitated with pulling my underwear off, trying to preserve some modesty and cover myself. She noticed this and laughed at me. "Don't worry about trying to cover yourself. I'm a nurse, I see this stuff every day. Not to mention I was still diapering you until what, just a year or two ago? It's not like I've never seen you naked." I hung my head slightly as I reached down and pulled off the last of my male garments. My bedwetting had never been a high point in my life, and my mother had been putting me in night diapers like she pointed out. She had only stopped with the diapers because I had outgrown the largest disposable diapers, not because I had stopped wetting. She would still ask me when she found my wet sheets if I needed to be put back in diapers.
With my shirt, pants, and underwear on the floor, I turned and picked up the panties. At least these were a plain cotton brief style. I knew from doing laundry as a family that my mother had some skimpier and sexier ones, these were much more modest. I slid them up my legs and into place. I turned my attention to the bra, picking it up and trying to figure out what was inside versus out, and once I had, I slid it up my arms and tried to figure out how to hook the straps in the back. As I was doing this, my mother came back with a green and blue flower print dress from her closet, setting it on the bed next to me. "Turn around, let me hook that for you," she said. I turned around and she grabbed the straps, pulling it tight around my chest. The wires that were in the bra under the cups bit into my armpits somewhat as I turned back around to see her holding the dress for me to put on. She had pulled down the zipper in the back and helped me slide it over my head before having me turn back around so she could zip it up for me.
As I turned back around, she looked me over and noted, "That dress really needs a slip under it." She stepped back to her dresser and pulled out a silk slip to hand to me, indicating how I should slide it up under the dress. I did the best I could, it took a bit to get it in place without getting the material of the dress caught in the waist of the slip as I pulled it up. My mother just watched with a slight smirk on her face as I did so. Once it was in place, she looked me up and down and pronounced, "OK, young lady, now you get to see what it's like to be a girl." She reached down and grabbed my boy's clothing, handing it to me and telling me to put them into my hamper and then come downstairs to talk to her.
I took the clothes down the hallway, acutely aware of the silk material swishing around my legs with every step, the cool air circulating around my bare legs and groin. The bra was still digging into my armpits and ribs slightly, and I wasn't sure what to think of it all. I dropped the clothes in the hamper in my room, and went downstairs to watch television, finding my mother already there.
I sat down at the other end of the couch from my mother, and we watched television quietly for a few minutes. As a commercial break started, she looked over at me and asked, "So what do you think of being a girl?"
I thought about it for a minute. "It's...different." I concluded. "How so?" she asked. "The dress is a lot cooler compared to my pants, you get a lot more air around your legs when you walk, and it's kind of nice with as hot as it's been lately," I answered. "The panties are comfortable and not as heavy as my regular underwear, which seems to keep things cooler too. Of all of it, I think the bra is probably the worst thing to deal with, it has wires that seem to dig into my ribs and armpits and it's not that comfortable."
"Well," my mother explained, "you're about my size for clothes, the only thing is that you aren't the same size for a bra. You don't have boobs like I do, so you could probably go without one, I figured that any girl your age will be wearing her first bra though, so you may as well see what it's like. You would need more of a training bra, like a 34AA instead of the 36D I wear. The wires help when you have big breasts like I do, you would probably find a properly fitted bra more comfortable. We could always go get you a properly fitted bra or two tomorrow if you want to see the difference," she joked.
I just blushed at this suggestion. "What do you think about how I look?" I asked.
She looked me up and down again. "Honestly, you look nice as a girl," she admitted. "With a bit of makeup, and doing your hair, I don't think anyone would know you weren't really a girl."
"Could we try that?" I asked. "I mean, the makeup and hair?"
"There's really not enough time tonight before bed," she concluded. "Maybe we could tomorrow if you wanted to, but certainly not tonight."
"Could we do that tomorrow?" I asked. Hearing what she said about how I looked, I really was curious to see just how much I might look like a girl with makeup and hair done appropriately.
"Sure. If you want to dress up again, then tomorrow we'll do your makeup and hair," she affirmed. After sitting and thinking for a couple minutes, she looked back at me. "So here's the next question I have for you: would you dress up again if you could?" she asked me. "I mean, if we made the clothes available for you to wear, would you wear a dress or skirt? Would you dress like a girl more than just this once if you could? Do you feel like you like it enough that you might want to dress other times?"
"I don't know," I responded. "I do like how the clothes feel, and I'm really curious about how I would look with hair and makeup. I guess I'm kind of worried about getting teased if I did."
"So if you knew you wouldn't be teased about it or anything, if there were a dress available for you to wear, would you wear it sometimes?"
"Probably," I reasoned. "I kind of like the clothes, other than the bra."
"Well, I've told you why the bra is uncomfortable," she said. "And I can tell you find the clothes kind of 'exciting'," she went on, pointing at the erection I had and making me blush. "There's nothing wrong with liking it, though I would hope you might get used to things enough that you can control it, that's a dead giveaway that you're not really a girl. There's other things, like how you walk, or how you sit in the dress, those are things you would need to learn about. Girls learn to sit with their legs together when they wear a dress or skirt, you should pay a little attention to it. Unless of course you want to flash your panties to all the boys."
I blushed heavily, and she laughed at me. "You want to know what it's like to be a girl, this is it. We'll do your hair and makeup tomorrow, so you can see what you really look like. For tonight, just get used to things a bit." We finished watching the program on television, and as we went upstairs to bed, my mother brought me into her room one more time. She walked over to her dresser and pulled out one of her nightgowns, handing it to me.
"You can wear this tonight to bed," she explained, "hang up the dress in your closet for tomorrow, and just set the bra and slip aside to wear tomorrow as well. Just try not to pee in my panties and nightgown if you could." I dropped my head in shame as I accepted the nightgown from her and retreated to my bedroom. It took a bit of trying for me to get the dress unzipped and the bra unhooked as I changed for bed. I stood there in the panties, dropping the nightgown over my head, and looked from the dress that hung in my closet to the slip and bra sitting on my dresser, and wondered what I had gotten myself into.
For my mother, she didn't go to bed right away. She got on the phone and called my stepfather at his hotel, wanting some feedback on the events of the evening. The two of them made small talk for a couple minutes before my stepfather asked, "So what's the real reason you called? It can't just be to chat about little things."
"It's not," she admitted. "Richard came to me tonight and wanted to know what it was like to be a girl."
"So what did you tell him?"
"I didn't know what to tell him," she said. "Can you tell me what it's like to be a man versus a woman? It's just something you do."
"Fair enough," he replied.
"I decided that if he wanted to know what it's like, that that was probably the best way for him to learn," she continued, "to have it be something he does. So I had him dress in some of my clothes for the night."
"How did that go?"
"He seemed to like it," she admitted. "He wants to do hair and makeup to see just how much he looks like a girl, so we're going to do that tomorrow. The thing is, I asked him if he would dress up again if the clothes were made available for him to wear."
"What did he say?" my stepfather asked.
"He was worried about getting teased about it. If that's not an issue, then he said he would. I just don't know how to make the clothes available to him that easily."
"Does he actually look good in the clothes? Does he seem to like it all?"
"If he had hair and makeup done, and then learned to walk and sit properly in a dress, you would swear he was a girl. He couldn't sit with his legs together and I had to warn him about flashing his panties," she went on.
"He was wearing panties?"
"Yes, I figured he should be dressed up all the way instead of just slipping on a dress. He did complain about the underwire from the bra digging in."
"And a bra too? Wow, you went all the way with this. So, what do you want to know from me? Just that I'm OK with it, or what?"
"I'm pretty sure we stop any teasing that might happen, and he said he would dress up again if the clothes are available, so I'm willing to let him dress as much as he wants. But the question is how?" my mother went on. "I can't keep letting him borrow dresses or skirts of mine, and wearing a pair of my panties and a bra for one day or the night is fine, but it's not really sanitary in the long run...so what do we do?"
"Why not buy him his own clothes?"
"I had joked about getting him his own bras so he could see how much more comfortable a properly fitted bra was, but I hadn't thought about doing it for real. Are you really thinking I should buy him his own things?"
"Why not? So what, he gets his own panties and bras, a couple of outfits, whatever you think he needs to dress up as a girl. Now you don't have to worry about him borrowing your clothes, and the girls don't either. He gets his own underthings which is more sanitary, I don't see what the downside of it is," my stepfather reasoned.
"He'll probably take better care of the clothes if they're his," my mother reasoned, "and he could dress up as much as he wants in them. You don't have a problem with him dressing as a girl?"
"Like he's ever been much of a boy, seriously. Not to mention the fact that I think girls are easier to raise anyway, and this would make four girls in the house instead of him being the odd one out. Besides, if he looks as good as a girl as you think, then it's fine."
"He needs to learn how to walk and sit in a dress, but other than that, he's very feminine. As for buying him his own things, what do you think I should get for him?" my mother asked.
"I would only do a couple outfits to begin with, until we see how often he wants to dress up. The thing is, if we're going to buy these clothes for him, I want to see how they look on him, I don't think it's fair that we spend money on things that he only wears in secret in his room," my stepfather finished.
"I think that's fair," my mom agreed. "I'm not going to do special loads of laundry for these either, so it's going to have to be out in the open in the family. We just need to keep the girls from teasing him, which I think we can do."
"Sounds like I'm taking him shopping tomorrow," my mom finished.