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The Question
(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 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 appropriate."

"Sounds like I'm taking him shopping tomorrow," my mom finished.
Beautifully written. Thank you
Note: I appreciate any comments and feedback on the story. There is still more I plan to write and put in here, it's just having the time to write...with that said, here's the next installment:

I woke up the next morning and as I slipped out from under the sheets, I saw the nightgown I was wearing and it reminded me of the night before. I looked over to the bra and slip sitting on my dresser. I looked into my open closet to see the blue and green flower print dress I had been wearing the night before, hanging there, waiting for me to change into it once again. My mom had said I looked good as a girl, that with makeup on and my hair done, nobody would know I wasn't a girl. I thought about whether or not I really wanted to go that far or not, and decided that it probably wouldn't hurt to do it and it might be fun. It certainly wasn't what I had expected when I had asked my mother that question the night before, but then again, I realized that I wasn't sure what I wanted to know.

I left the nightgown on to go down and go to the bathroom. Trying to hold all the fabric up as I stood to pee, became rather difficult, but I managed to get it done and pulled the panties back up before heading downstairs. Walking in to the kitchen to grab a bowl of cereal, my mom was standing there already with a cup of coffee.

"Well, at least you didn't pee in my nightgown last night," she joked. I turned red and concentrated on getting breakfast for myself. She continued on. "You had said last night that you wanted to get your hair done today and some makeup on so you can see how much you really do look like a girl, do you still want to do that?"

"Yeah, I'd like to see what I look like," I answered sheepishly.

"Well, we've got that to do today, and we need to go do some shopping, so once you're done with breakfast, go ahead and change and we can get started on things," she finished.

As I finished gathering my breakfast, she finished her coffee and left the room to finish getting ready for the day herself. I ate quietly, thinking to myself about the plans for the day. If we needed to go shopping, I didn't want to go out wearing a dress. At the same time, if my mom spent a bunch of time doing my hair and getting makeup on me, I was pretty certain she wouldn't be happy to undo it all just so we could go run errands. I finished my breakfast, put my bowl and spoon into the sink, and headed back up to my room.

As I closed the door behind me, I looked at the dress in the closet again. It would certainly have to wait until after we got the shopping and whatever other errands we needed to run out of the way. I slipped off the nightgown, folded it, and placed it on my dresser next to the bra and slip from the night before. I looked down at the panties I was wearing and decided I should take them off as well; I didn't want to run the risk of having my shorts slip down my waist slightly and have the lacy edges of the panties showing while out and about. I took them off and set them on top of the nightgown, then got out a pair of my regular underwear to put on, together with a pair of shorts and a t-shirt.

Getting dressed, I put on a pair of sandals and went downstairs to see if my mom was ready to go or not. I went back to the kitchen to find her completely dressed and finishing another cup of coffee. She looked over at me, and noticing my attire, asked, "I thought you wanted to do hair and makeup?"

"You said we needed to go out, so I figured we would wait with it until we were done with that," I explained.

"Suit yourself," she shrugged her shoulders. "I guess we'll head out first thing then." She set her coffee cup in the sink and looked back to me. "I'm going to grab my purse, go ahead and get in the car and we'll go."

I went out, got in the car and strapped myself in. My mom came out and got in the driver's seat, started the car and we pulled out of the garage. As she hit the button to close the garage door, she began to talk. "I called your stepfather last night and told him about what you asked me." I looked over at her, afraid to hear what he had said about it. She obviously saw the fear on my face and went on. "Don't worry, he's fine with it. The thing is, you had said you would dress up again if the clothes were available, would you still do that? I mean, I understand you're worried about getting teased, but if we could keep it in a safe space where you don't get teased, would you dress up as a girl?"

I couldn't do much besides nod, somewhat in shock that she had told all of this to my stepfather.

"Well, we discussed that," she went on, "and we're both OK with you doing that, but it kind of presents a couple of issues. Your sisters certainly aren't going to want you borrowing their clothes, and depending on how often you want to dress up, I can't always make my clothes available. Not to mention the fact that sharing underwear isn't really sanitary. So the idea we had is to get you your own things. That way, you can dress up as often as you want. Not only that, but you'll get a bra that fits instead of trying to make do with one of mine." She chuckled slightly, noticing my nervousness, and trying to make light with the reference to the night before.

We kept quiet for a while, me slowly digesting what she just suggested, while she concentrated on driving. As we neared downtown, she began to talk more. "One thing about doing this for you: if we buy you these things, you don't just get to wear them in secret in your room. If we spend this money on you, your stepfather wants to see how you look in them, and your sisters will probably get to know as well. You should wear them somewhat regularly, so it'll be hard to hide it. Not only that, but I'm not going to do special loads of laundry for just your things, so everyone in the house will know. We'll make sure your sisters don't tease you, but there may be special occasions where we want you to dress up." We pulled into the parking lot and found a space. As my mother got out of the car, I was still unsure what to think about all of this.

She came over to my door and opened it. "Well, unless you've got something to say, let's go!" I got out of the car quietly and followed her into the department store. 

Entering the store, she immediately headed to a section marked 'Intimates'. I followed my mother meekly, somewhat wanting to just disappear. She headed to a rack full of packages of panties, looking them over and noting the sizes. "Let's see, the size seven you wore last night seemed to fit perfectly...great! Here we are, size seven. She looked at the patterns and pulled out three packages, thrusting them into my hands. Not sure what to do, I said, "What am I supposed to do with these?"

"They're yours, you can carry them. Now let's get you a couple bras," she finished.

I looked down at the packages of panties in my hands, reading the front of them, trying to make sure I didn't make eye contact with anyone around. each package held three pairs of panties, 'Women's Cotton Briefs' was the description. I looked at the patterns she had settled on--tiny flowers all over, with light lacing around the legs and waist. I followed my mother quietly over to a rack of bras. "Let's see," she talked quietly, "here we are, I just got Mindy her first training bras last month, let's see if they have a 34 double A for you." I wanted to crawl into the carpet, the mention of my youngest stepsister reminded me that she would know I had these things and would probably see me in them as well. My mother picked out three bras and handed them to me to put with the panties. I looked at these new items. They had even more lace, but were mostly a sheer white fabric except for a tiny pastel flower nestled between the cups.

My mother walked over to the 'Young Miss' section with me in tow. She began scanning over racks of sundresses, occasionally taking one out and holding it up to me to see what she thought. She settled on two similar dresses in different sizes and handed them to me, then began looking over a rack of skirts. She picked out a couple blue skirts, then found a white blouse that she thought would pair well with it and handed a couple of those to me as well. Keeping quiet, I meekly accepted them and hoped we were getting close to being done. She looked at me and said, "OK, let's go see how they fit!"

My jaw dropped. I had thought it was bad enough to be out shopping for girl's clothing for me like this, but now she wanted me to try things on? I protested a bit. "But, can't we just get them and go?" I didn't want to be having to put a dress on in the fitting rooms of the department store.

"Absolutely not," she was adamant. "We really need to see how these fit on you, I've never bought clothes for any of you without having you try them on first, I'm not going to start now." She found a younger sales girl on the floor and asked, "Excuse me, where can he go try these on?" The girl looked at the dresses and skirts in my arms, then pointed to the women's rooms. "Yes, ma'am," she said, "you can go try them on in the fitting rooms."

"No," my mother corrected, "not me. These are for him." She pointed directly at me, emphasizing her point. "Not me. Still over there?"

The girl looked over at me, and at what I was holding. The realization of what was being asked hit her. "Yes, ma'am," she replied, "I'm sorry, I thought they were for you. If they're for him, he'll need to use the boy's fitting room." She pointed out where they were at, and noticed me blushing, head hung quietly. "Sorry, but it's company policy. We get men in here occasionally buying things like this. If they come in dressed as men, they have to use the men's room. If they come in and look and act like women, then they can use the women's," she explained.

My mother thanked the girl and walked me over to the boy's fitting rooms. "See," she said, "maybe we should have done your hair and makeup before doing this today. You're the one who decided to wear what you did, it wouldn't have been so much of an issue if you had worn the dress now, would it?" I didn't say anything as we walked up to the fitting rooms. "Here," she said, "give me your panties, go try on the dress first, and try at least one of the bras on as well."

I handed her the packages of panties and took the rest into the fitting room, hanging them all on the hook on the back of the door. I slipped off my sandals, and took my shorts and shirt off. I stood there, looking at the dresses, skirts, blouses, and bras hanging on the hook. I took a deep breath, and fumbled with getting the first bra off the hanger. Once I finally got it free, I slipped it up my arms and worked on hooking it behind my back. It took a couple minutes, but I was finally able to get it done. I slipped one of the sundresses off the hangers, and slipped it over my head. I looked at myself in the mirror, and called out to my mom, "This one fits!"

"Come let me see," she responded. I had dreaded her wanting to see. I didn't want to step out in the open wearing this, I was ready for the earth to open up and swallow me. "Come on," she insisted, growing impatient. I knew better than to try her patience, or she would really make things difficult and embarrassing. I opened the door, and stepped out to where she could look me over. I felt fortunate that there didn't seem to be anyone else around.

She looked me over, pulling the fabric of the dress up a bit and letting it fall, before rubbing her hand across my back. "You have one of the bras on?" she asked. I knew she could feel the strap of it, I just nodded as she pulled the strap slightly, testing the fit. Satisfied, she looked back at the dress. "This one's a little too big," she noted, then looked at the label. "Try the other one on, I think it will fit better around your waist and hips. It's good we're getting you panties as well, your regular underwear shows horrible lines under this." I walked back into the dressing room to change as directed. When I came back out, she again went over me, having me turn around. As I did, I noticed the sales girl off in the distance, craning her head slightly to get a look at me. My mother seemed satisfied, and I went back in with orders as to which blouse and skirt to try on first. The blouse took a little getting used to the buttons being on opposite sides, but once I came out and got looked over my mother seemed satisfied enough to send me back in to change into my regular clothes while the sales girl walked up.

"Those look really nice on him," she commented to my mother. "Any particular reason you're buying him them?"

My mother looked back at her and smiled. "He asked what it was like to be a girl, so we're letting him be a girl to find out for himself. He seems to like the clothes and told us he'd dress up if the clothes were there, so we're getting him clothes to dress in." The sales girl nodded her understanding.

"Well, when you're ready to go, let me know and I'll ring you up," she walked away as I came out with the clothes. My mother hung the clothes that she felt didn't fit on the rack to go back on the floor, chuckling slightly at just how out of place they looked, the yellow sundress, white blouse, and blue skirt hanging there next to the boy's slacks and button-down shirts.  We walked back over to the 'Young Miss' section to continue shopping.

"I think we should get you at least one nightgown as well," she told me. She looked over the racks of summer-weight fabric and found one that she liked and held it up to me. "This should fit, what do you think of it?"

"It's fine," I said, eager to get this shopping trip done.

"Well, you're going to be the one wearing it, so you better be happy with it," she retorted. She looked around the area a little bit more, and her eyes settled on the bathing suits. "You're probably going to want to be in the pool a lot this summer, so we should get you a bathing suit as well," she indicated, walking over to the racks. She began flipping through the one piece suits, and I stood there quietly, looking around. My eyes settled on a red bikini with white trim on it. "What about this?" I asked my mother.

"I don't think you're ready for a bikini yet," she said, smiling. She found a red one piece suit that she liked, and added it to the pile of clothes in my arms. She found the sales girl who had helped us earlier, and we walked over to the cash register.

Ringing us up, the girl could only help but smile at all the things I was being bought. As she rang up the panties and bras, she asked, "Are you sure everything fits? We can't do returns on undergarments." My mom just smiled. "I had him try on one of the bras, and the panties are the same size as the ones he had on yesterday, so we should be fine," my mother answered.

The girl just nodded and looked over at me where I stood with my head hung down. "If it's anything to you, these things look really pretty on you," she remarked. "If you were to wear them in next time, you could use the girl's dressing rooms and not feel so out of place." She smiled sweetly at me, and I thanked her politely for the compliments, knowing my mother would berate me if I didn't. We paid, and carried the bag of clothes out to the car, my mother commenting that she wasn't the only one who thought I looked nice in a dress. She opened the trunk and I placed them in, turning to go get in. Instead she turned back towards the shops on the main street, urging me to follow. "Shoes next!" she smiled.

We walked into the shoe store, and my mother immediately went to the women's section to look things over. As she settled on a pair of low wedges, I found some sandals that I thought she might approve of to go with the sundress she had just bought me. As I pointed them out, she just smiled broadly at me, saying, "You really do have a good fashion sense, maybe you're more girl than boy." She went over and found a salesman and brought him over to where she had sat me down. "We need to get his feet measured and look at these shoes, please."

The salesman took my foot and placed it on the measurement tool. "Men's nine and a half," he proclaimed.

"That's fine," my mother agreed, "but do these come in men's sizes?" She held up the wedges and sandals for the salesman to see. It took a moment, and then he grabbed a different tool and placed my foot on it. "Women's ten and a half," he chuckled. My mother handed him the shoes and we sat there while he went in the back. I could hear a fair amount of laughter coming from the back, I just sat with my head down, knowing they were laughing at me. The sales man came back with the shoes, and handed them to my mother and I, together with a couple nylons to put on my feet while I tried them on.

The salesman chuckled as I tried walking around in the wedges, not having any practice with any sort of heels. My mother ended up being satisfied with both pair and we paid for them and started to leave. My mother was already out the door, and I was a few steps behind her carrying the bag with my shoes in it, when I overheard the salesman who helped us joking to another salesman.

"So," he asked, "do you think he's just some queer little faggot, or did he do something to piss momma off really bad?" As the door shut behind me, their laughter was the last thing I heard.
Really enjoying this and very well written...keep going!
(11-21-2016, 08:12 PM)Sissy Matthew Wrote: Really enjoying this and very well written...keep going!

Thanks for the compliment. I'm glad to hear people like the writing--I'm an engineer by trade, so most of what I do is technical writing (and how many engineers can do a good job writing in the first place?), stuff like this is not normally what I spend time doing.  More will come, especially once I get some time off from work!
Next installment:

As we got in the car and headed out, my mother could tell I was somewhat drained by the day’s experiences. “How about we do an early lunch?” she suggested. “You were very good about getting all this stuff today, so how about your favorite place?”

She knew I liked a certain fast food restaurant, and so we headed there to order. As we sat with our food and ate, she talked quietly to me. “Listen, I know a lot of this is new stuff to you, I’m sure it’s going to take some time to get used to it all. To tell you the truth, I hadn’t been thinking this would be the plans for the weekend, but it is what it is. There’s nothing wrong with being curious, and I’m proud that you’re willing to try these things to learn for yourself what it’s like.”

Between bites, I nodded my head and quietly said, “Thanks.”

“Part of the reason we wanted you to have your own things,” she went on, “is that you’ll hopefully take better care of them than if they were borrowed from someone else. I certainly hope you can keep your panties a bit cleaner than you do with your underwear now.”

I turned red again, for what seemed to be the hundredth time. I knew what she meant, of course. No matter how many times I wiped after going to the bathroom, it seemed I never could get clean enough and I would leave ‘skid marks’ in my underwear. My mother always nagged me about it, between that and my bedwetting, it seemed I couldn’t get a break. I thought about it for a bit. “What do the girls do?” I asked my mother.

“They wipe clean after going to the bathroom,” she replied.

“Well, what about when it’s that time of month?” I asked. Being the child of a nurse meant we had learned about our bodies and biology in general quite a bit over the years.

“Oh, that gives me a great idea,” my mother said. “I think it’ll work, but we’ll have to try it to make sure. Are you done with lunch? We still need to run one more place before we head home.”

I finished my food and we left, stopping at a nearby drug store. We went inside, with my mother grabbing a small basket as we passed the stack of them. She took me down the cosmetics aisle, pausing every so often to look at and pick up different items to place in the basket. “Foundation…mascara…eye shadow…eye liner…blush…lipstick,” she verbally listed each one as she ticked them off her mental list, occasionally holding one item or another up to my face to look at the colors. Last, she picked up a bottle of nail polish and set it in the basket, a light red that was almost pink.

We headed over to another aisle marked ‘Feminine Needs’ that she steered us down. She looked over the packages on the shelves, seemingly intent on finding one thing in particular. “Here we are,” she announced, dropping a package marked ‘Lightdays Longs’ into the basket. “Anything else you feel you want or need?” she checked as we headed toward the front. Passing the infant care aisle, she jerked a thumb over and joked, “Not needing diapers, are you?” I could only put my head down and shake it, quietly saying, “No.”

The rest of the drive home was quiet until we turned into our neighborhood. “When we get home,” my mom told me, “We’ll put your clothes in for a quick cycle on the wash. I want you to go upstairs and run yourself a bath. I should have got you razors to shave your legs, but I forgot, so I’ll let you borrow one of mine, I’ll help you with it. I want you to wash your hair and body, and then I’ll help you get dressed in your new clothes, we’ll do up your hair, and get some makeup on you.”

We got out of the car, and she pulled my new clothes from the trunk, handing me the bag from the drug store and the bag with the shoes in it. “Go ahead and take the shoes up to your room, the other stuff into your bathroom,” my mother ordered. “Oh, and bring my clothes back down to my room if you don’t mind.”

I did as requested, and was about to head into her room with her clothes from the night before as she was walking up the stairs. She grabbed them from my hands, and reminded me, “I want you to go ahead and go take a bath, I’ll be there in a few minutes to help you shave your legs.”

Turning to enter the bathroom, I started running the water into the tub to heat it up, and began to undress. As the tub finished filling, I turned off the water and looked down at my naked body, trying to imagine what it would look like if it were a girl’s body instead of what I currently had. I slipped into the tub, sinking down to relax a bit. I dunked my hair in the water to get it wet, and began to shampoo it when my mother walked into the room.

“Good,” she said, “don’t forget to use conditioner on your hair as well. Styling can sometimes be hard on it.” I tried to cover myself again as she walked over to the edge of the tub. “Please,” she intoned, “didn’t I tell you last night, I see naked people all the time, and it wasn’t that long ago I was diapering you every night and seeing you naked. Besides, girls aren’t bothered by seeing other girls naked.” She winked at me with the last statement.

I dunked my head back in the water as she laid a safety razor down on the edge of the tub. While I used the conditioner on my hair, my mom went to the bag on the counter and pulled everything out, discarding the bag itself in the trash can. She walked back over as I rinsed out the last of the conditioner, and picked up the razor.

“Go ahead and stand up,” she told me. “Hand me the soap…please quit with trying to hide yourself, just move your hands.” I handed her the soap, and she lathered up a small amount and put it on my legs. “The soap helps with shaving so you don’t nick your skin,” she explained, “go in long, neat strokes, usually from the bottom up. Sometimes it helps to put one leg on the edge of the tub to do this.”

She helped me start with one leg, then left me to do the other while she ran downstairs to switch my clothes to the dryer. She came back in to check over how I had done, pointing out spots I had missed. She had me stand there for one last look, hands at my sides, looking up and down. “Go ahead and wash up a bit more,” she told me, “I’ll be back in a minute.”

I hadn’t got far with washing myself when she walked in holding a pair of scissors that I knew she used for trimming hair, motioning for me to stand up again. “You’re getting a bit of pubic hair now,” she explained, “you want to keep it trimmed a bit so it doesn’t stick out when you’re wearing something a bit narrower in the crotch.” She reached towards me with the scissors opened, and I reflexively stepped back.

“Don’t worry,” she chuckled, “I’m not going to cut anything off, just trim back the little bit of hair you have there.” She pushed my hands away and pulled at and trimmed the small amount of pubic hair I had. “Some girls like to shave their crotch, for now we’ll just trim yours back and let you decide later.” She finished with scissors, and placed them over on the counter. I finished washing my body, and then used the shower head to do a final rinse off before draining the tub, all under mom’s supervision.

She handed me a towel to dry off with as the water circled the drain. I dried my hair, and then my body. My mom took the towel from me and showed me how to wrap it around my chest and tuck in the end; “After all, girls don’t necessarily want to walk around with their boobs hanging out,” she chided.

The curling iron was plugged in, and then she grabbed the hair dryer that my sister and stepsisters shared. Taking a brush in her other hand, she had me kneel on the floor in front of the mirror while she went to work on my hair. The first several minutes seemed to concentrate on getting my hair dry while also getting it to stand up and have a bit of volume, then switching over to the curling iron to put a small amount of curls into it. I wasn’t expecting it when she reached down and grabbed the scissors and trimmed a few spots in my hair, hoping that it wouldn’t mess up how my hair would look as a boy. After spending some time double checking how things looked, she pronounced me done.

“If you were to let your hair grow out longer,” she remarked, “we could do a lot more with it. Give me a minute and I’ll go get your clothes from the dryer.” She left me there and I could only look at myself in the mirror, transfixed by the change the hairstyle had made. The face looking back at me was still mine, but it wasn’t really a male or female one—just the way my hair had been styled looked feminine, but I could still barely see the underlying boy that I still was underneath.

My mother walked back in a minute later holding the yellow sundress together with a pair of panties and bra that we had just bought. She laid them down on the counter, and handed me the panties to begin with. I slid them up my legs, and while I did, she grabbed one of the packages from the drug store off the counter. “These are panty liners,” she noted, “girls can regularly get some small amounts of vaginal discharge between their periods, so we use them to keep from ruining our panties.” She pulled open the plastic and pulled out one of the thin pads. She flipped it over and showed me the adhesive strip on the back. “They just stick in your panties, you put in a clean one every day, and fold up the used one with the adhesive on the outside and wrap toilet paper around it to put it in the trash. Here, pull your panties down and put it in.” She held it out for me to take.

I slid my panties down to my knees, and then took the paper off the back to expose the adhesive. “You’ll want yours a little further back where us girls usually stick it straight in the middle,” my mother advised. I stuck it in place and pulled my panties up. “These will be under the sink here next to the ones the girls use, let me know when you’re running low and I’ll get you more,” she finished.

“Next to the girl’s stuff?” I asked, somewhat scared. There would be no way that they wouldn’t know now, I was afraid of what might come of it. “They’re going to find out…”

“I told you already, this isn’t going to be a secret, everyone living in this house is going to have to find out,” my mother admonished. “Your stepfather and I will make sure you don’t get teased about it,” she finished, trying to calm my nerves. She placed the package under the sink in the space reserved for anything of mine. I saw similar packages for each of the girls, and resigned myself that it was going to be completely out in the open.

I took off my towel and hung it up while my mother handed the bra to me. “Some girls like to hook it in front, then bring the cups around and put their arms through the straps. Some of us have just gotten used to hooking it in back, so you can do whatever you think is easiest.” I took the bra, looked at it, then slid it up my arms and hooked it in back as best I could.

“You’ll get used to it and it’ll be easier,” my mom explained. “Is this more comfortable than the one last night?”

“Definitely,” I agreed.

“Having a properly fitting bra is always worthwhile,” she fiddled with the straps on my shoulders while she spoke. “I remember getting the girls their first bras, never really expected I’d be doing it for you too.” Satisfied with the fit of the bra, she picked up the sundress and handed it to me to put on. I dropped it over my head, and she looked me over.

“That’s a very pretty color on you,” she noted. “Now, turn around and face me and we’ll get some makeup on your face. I got you your own, since I doubt the girls want to share any of theirs.”

I faced her and she began to apply things one by one, giving me descriptions and directions on how to use them at the same time. In the short breaks that came, I thought back about the day. “Mom,” I asked, “do you think I’m gay?”

“Whether or not I think you’re gay shouldn’t really matter, what matters is what you think. Why do you ask?”

“When we were getting shoes today,” I explained, “when we were leaving, I overheard one of the salesmen asking another if they thought I was queer.”

“Well, whether or not you’re gay depends on what you feel and think,” she reasoned. “It depends on whether or not you’re attracted to boys or girls. If you’re gay, that’s fine with your stepfather and I, but I know we would certainly be happy if you all found nice men to marry.”


She laughed at me. “Now you’re relaxing a bit! Good!” She continued applying the makeup. “Look,” she reasoned, “you wanted to know what it was like to be a girl, and there’s a lot for you to learn. Who you’re attracted to isn’t that important with it, but it is important that you understand that if you do this right, people won’t see you as a boy in a dress, but they’ll think you’re really a girl. That’s why I pointed out last night how you were sitting in the dress; if boys think you’re a girl, they’re going to want to sneak a look at your panties. You need to learn not just how to dress like a girl, but to act like one as well.”

She stepped back and admired her handiwork. She motioned for me to turn around and look at myself in the mirror. I was amazed to see the boy from earlier completely gone. Nothing about the person looking back at me even hinted at not being a girl.

“Put your makeup in your drawer, and bring your nail polish downstairs and we’ll do your nails,” my mother said as she stepped out.
I opened the drawer that I had for my things in the bathroom. It had been sparse in there before—toothbrush, toothpaste, comb and brush, that was about it. As I placed each of the bits of makeup in there, I looked them over and tried to remember what my mom had said about how to use them. Foundation, just enough to even your skin tones out. Blush, just a bit to highlight your cheekbones. Eyeshadow, just on your eyelids and not too heavy. Eyeliner, just the edges of your eyelids. Mascara, one or two strokes to make your eyelashes longer and thicker looking. Lipstick, a thin coat to color your lips. Overall, don’t use too much makeup, you want to highlight your natural features, not hide them. Not to mention that with too much you look like a cheap whore…

Closing the drawer, I stopped to look in the cabinet under the sink. My area under the sink didn’t hold much before, just a seldom used bottle of hair gel. Now, the package of panty liners sat right next to it. The things my sisters used were there as well, each of them had a package of panty liners of one type or another, and they also had boxes sitting next to them. I pulled one out and looked at it. ‘Tampax Tampons’ was what it said on the front. I took one out, finding it to be what looked like a plastic wrapped marker. I put it back, then pulled out the folded piece of paper inside. I opened it up and looked it over. There was a huge amount of warnings about toxic shock syndrome, and then diagrams and descriptions of how to insert one. It was interesting, but my mom was waiting for me downstairs. I folded the paper back up and put it all away before grabbing the bottle of nail polish and heading downstairs.

My mother was in the kitchen again, getting herself another cup of coffee. “Was wondering what happened to you,” she chuckled.

“I just,” I paused, not wanting to explain the fascination I had had with the box of tampons, “it’s just that I was looking in the mirror and getting used to this.”

“Fair enough,” she replied. “It’s been a long time since you last wore a dress, you probably don’t remember it. Go ahead and sit down and we’ll do your nails.”

I sat down, wondering what she meant. I had worn a dress before? I certainly didn’t remember wearing dresses at any point in my life. She had me put my right hand on the table and shook the bottle of polish before opening it and laying down a layer on my fingernails.

“Mom,” I asked, “what did you mean it’s been a long time since I wore a dress?”

“You were still pretty young, I’m not surprised you don’t remember,” she answered. “Do you remember how old you were when you were potty trained?”

“No,” I replied. While there had been a number of times I was in diapers during the day for occasional bladder and bowel accidents, and I had been diapered nightly up until a couple years prior, potty training wasn’t something I remembered.

“Spread your fingers a bit,” she instructed, “you don’t want to touch your nails to anything while they dry. As for potty training, you didn’t start with it until you were almost five. It was really frustrating, because I had been hoping you’d be out of diapers before you turned three, like your sister.

“Anyway,” she continued, “one of the hardest things with changing your diapers as you got bigger was that I had to pull your pants or shorts off to get the plastic pants off and then change your diaper. Pants and shorts for babies have snaps in the crotch to make this easier, but not for older kids. Your father didn’t understand very well with as much as he was out of the house flying, but I needed to find some way to deal with this. Having you run around in a shirt and diaper was fine for at home, but not out and about.

“So, since your sister was the last girl born of all the cousins,” she explained, “we had all the hand-me-downs from her that weren’t going to go anywhere. I figured we could get some extra use out of them by putting you in them. It would make diaper changes easier when we were out, and some people thought it might even give you some incentive to potty train.”

“Oh, I don’t really remember this,” I said.

“Like I said, you were really young, so I’m not surprised you don’t remember,” she went on. “Your father didn’t like it when he found out, but I didn’t really care, he was making me stay home instead of going back to work and he never dealt with your diapers anyway.” She paused for a moment. “OK, that hand is done, make sure not to touch your nails to anything, but why don’t you try doing your other hand.” She handed me the brush from the bottle.

As I began to try and work the polish on to my nails, my mother went over to freshen her cup of coffee, and she continued to talk to me. “With diapers for bed, it wasn’t really a problem, it wasn’t like we were going out anywhere that I’d have to change you, so it wasn’t a big deal. The few times you had trouble during the day where we put you in diapers really weren’t that big of a deal since it only seemed to last a few weeks. I did consider having you in some of your sister’s old things right after the divorce when money was tight, but when I met John things got better and we didn’t need to do it. I didn’t think you’d be wanting to wear them on your own.”

“I hadn’t really thought about it before yesterday,” I admitted. “I’m still not sure what I was hoping to get for an answer when I asked you what it was like.”

“Well, this is what I thought would help you understand the best,” my mom reasoned. She came over to look at how I was doing on my nails on my left hand. “Not bad, you’ll get better with practice. Anyhow, I wasn’t sure how to answer that question either, so I figured if you wanted to know and were willing to dress up, it would give you a taste of it. I was a little surprised when you said you wanted to do your hair and makeup, and more so when you said you would dress again. I have to admit, you show some very decidedly feminine traits, and you look really pretty as a girl, so maybe this shouldn’t be a surprise.

“Of course,” she went on, “you’re worried about getting teased about this. We’ll make sure the girls don’t tease you, but I think it would definitely be worthwhile for you to really learn how to present yourself as a girl. You certainly look the part, but you need to act the part so people don’t see you as anything other than a girl when you go out.”

“Go out?” I was worried again. It was bad enough that my sister, stepsisters, and stepfather would know, but my mom expected me to go out in public dressed as a girl?

“Calm down,” my mother soothed, “it’s not like we’re going to tell anyone that you’re a boy underneath. I can see John and I wanting to take all you girls out for dinner or for some special occasion, so don’t be surprised if that happens. The thing is, if you can act like a girl, you already look like a girl, everyone is going to think you’re a girl, not a boy in a dress.”

I thought about this while I let my nails dry. “You need to learn some things pretty quick that the girls have been learning for a lot of years,” my mother went on. “You should smooth out your dress or skirt behind you before you sit down, and you need to either sit with your legs together or crossed. If you sit with them open, you end up letting everyone see your panties. Understand, when people think you’re a girl, you’re going to get treated as such. Boys are going to think you’re pretty and be attracted to you sexually, so that’s something you better think about. If you’re constantly flashing them your panties, they’ll think you’re attracted to them sexually as well.”

I blushed at what my mother had just told me. I understood her point, thinking back to the face I had seen in the mirror just a bit before. I certainly looked the part, but would I be able to act it as well? “I’m not sure about this thing with boys,” I said with hesitation.

“Sweetie, it’s not something you get to control,” my mother explained. “Look, there’s a lot of kids out there who would beat you up if they knew you were a boy under that dress, we’ll certainly do what we can to prevent it, but the best prevention is never giving them the slightest hint you’re not a girl. The downside to it is that you’re going to be seen as a girl and treated as a girl, so you need to think about life from a girl’s perspective. Boys and how they treat you and look at you, how you react to that and treat them in response, that’s part of it.”

I couldn’t argue with her logic. “I hadn’t figured I’d be going out as a girl when I asked you last night,” I admitted.

“Well,” my mother explained, “I hadn’t figured you’d even ask me a question like that. But you did, so I came up with an option for you, and you seemed to like it enough to want to do it more, so here we are. You wanted to know what it’s like to be a girl, you’re going to learn all of it firsthand. After how much we spent on you today for the clothes and makeup and everything, we don’t want it to go to waste, so we expect you to wear these things regularly.”

“OK,” I replied. I knew at this point I was stuck. By not protesting it earlier, and letting my mom take charge as we did the shopping while I still was in a state of shock, now my choice had been made.

By this point, my nails were dry, and my mom brought the rest of my clothes in from the dryer. She helped me to hang up the skirt and blouse, and helped me fold my panties, bras, bathing suit and nightgown. She handed me the hangers with the skirt and blouse, and took the rest, motioning me to follow her up to my room. When we entered, she went over to my dresser and opened the underwear drawer while telling me to hang up the skirt and blouse in my closet. I walked back over as she finished putting things away, noticing she had moved much of my regular underwear to the side and saw the new panties and bras on prominent display next to them. The nightgown she handed to me to place under my pillow, while she placed the bathing suit in the drawer with my pants and shorts.

“Why don’t you grab your wedges and come downstairs and you can practice walking in them,” she pointed to the new boxes on the floor of my closet.

I opened the box and pulled them out. They weren’t that tall in the back, maybe an inch or inch and a half more than under the toes. They had a thick canvas that went over the front of the foot but had an open-toe, and then another piece to hold your heel in. They were a neutral beige color, something I figured my mom picked out so they could go with most outfits.

I padded down the stairs behind my mother with the shoes in hand. I sat down in the kitchen again, and pulled the shoes on my feet. My mother looked down at them and remarked, “You should probably paint your toenails later.” She pulled me to my feet from the sitting position and I tried to maintain my balance as best I could. The problem I found was not so much the difference in height between the heels and toes, but that height coupled with the narrow heel took some getting used to.

I tried walking back and forth across the kitchen and found a lot of trouble doing so. My mother watched me, and as I sat down, she started pointing out my problems.

“You’ve got to remember that the heels on these are a lot narrower than what you’re used to for shoes. If you were in actual heels it would be worse, but when you step with your feet wide apart, it puts your weight off to the side and makes your ankle unstable. What you need to do is take shorter steps and keep your feet under you, almost like a heel-to-toe walk except that you put more space between each foot,” she explained. As she did, she walked back and forth in front of me a couple times to try and highlight what she was saying.

I stood back up, and tried to focus on what I was doing while walking. It certainly was easier when I kept my ankles under the middle of my body to not wobble like before. It certainly took a lot more concentration to keep myself focused on how to step and then move the next foot forward. I made it across the kitchen and came back to stand in front of my mother.
“Much better,” she complimented, “though you should practice a lot more walking around in shoes like these until you don’t have to think about it. It’s definitely a more feminine walk, and it gives your butt that little wiggle that drives boys crazy.”

“Mom!” I blushed again.

She just laughed at me. “Like I said,” she told me, “this is all part of being a girl. Whether or not you like boys is only part of it, they’re definitely going to think you’re pretty and they’re going to like you. So you need to be ready for when something like this comes along.”

I could only drop my head, understanding what she said to be true. I walked back and forth one more time across the kitchen, and then went to sit down at the table. “Hold it,” my mom said, “when you sit down brush the back of your dress so it’s under you and not getting wrinkled.” She showed me how to keep it from bunching up under me, and had me sit. “And remember to either cross your legs or keep them together when you sit in a dress or skirt.”
Sorry, I hadn't had much time to write lately, here's another installment.

I spent the rest of the day under my mother’s constant supervision, learning how to walk, sit, and stand like a ‘proper young lady’. There were short breaks, like dinner and a bit of time relaxing while watching television after, but there was still her watchful eye making sure I didn’t lapse into walking or sitting like a boy. I did figure out one thing on my own, which was using the bathroom to pee. It turned out to be rather difficult to hold up the hem of my dress, pull down my panties, and point myself to pee standing up. After fumbling for a minute trying to do this, I gave up and sat down, finding it much easier to control everything.
Through the evening, my mother talked to me about my dressing. “You should probably spend the next few days dressing up and getting used to this, practicing doing your hair, makeup, and nails,” she said. “John gets home from his trip Wednesday evening and he wants to see how you look in one of your outfits.” She must have seen a bit of worry on my face. “Don’t worry,” she tried to calm me, “he’s not going to tease you about it. One thing to remember is that if people see you and think you’re a boy in a dress, you’re a lot more likely to get harassed about this. If they can’t tell you’re not a girl, then they won’t know there’s anything to tease you about.”
“I’ll help you work on everything when I get home from work,” she instructed, “but you’re going to have to get good at this on your own. You’re not always going to be able to have someone else do this for you or help you.”
When bedtime rolled around, my mother gave me a bit more instruction on removing my makeup and preparing for bed. “Most girls don’t wear their bras to bed,” she instructed, “usually just their panties under their nightgowns. You should probably set aside most of the clothes to wear again tomorrow, I think you should get as much practice with all of this as possible. Put on clean panties and a clean panty liner in the morning, but your bra you can usually wear two or three days before it needs washed.”
I went to my bedroom and started to get undressed. I put my shoes on the floor of my closet, and hung up the yellow sundress next to the skirt and blouse already there. I stood there, just looking down at myself, at the bra and panties I was wearing. It wasn’t something I had pictured myself doing, it was certainly going to take some time to get used to. I pulled the nightgown my mother had bought for me out and slipped it over my head and walked down to the bathroom to brush my teeth and prepare for bed.
I stepped into the bathroom and looked in the mirror. I still looked decidedly feminine. I grabbed the soap and scrubbed my face with a washcloth. I didn’t know how much makeup I had on, but I hoped I got it all off. I brushed my teeth, and tried brushing some of the curls out of my hair as best I could. As I dropped my brush back into the drawer, the new containers of makeup stuck out like a sore thumb from the limited items I used to have in there. Last, I pulled up my nightgown and dropped my panties to sit down and pee.
As I finished, I pulled my panties back into place and looked at myself in the mirror again. Even with the makeup gone and my hair somewhat brushed out, I could see myself looking more like a girl than a boy. I padded down the hallway to my room while thinking about this. Maybe my mother was right, maybe I could pull off making everyone think I was actually a girl. These thoughts turned over in my head as I drifted off to sleep.
The next morning I woke up and went downstairs to have breakfast. My mother was finishing up her coffee as I stepped into the kitchen. Seeing me, she looked me over and commented, “That nightgown looks really nice on you.” I didn’t really know what to say in response, so I just said, “Thanks.”
As she put her coffee cup into the sink, she told me, “You really should spend some time today trying to learn how to do your makeup and hair. It won’t hurt if you have to take it off and try again a couple times to get the practice you need.” I just nodded my assent as she grabbed her purse and walked towards the garage. “And remember,” she finished, “clean panties and a fresh panty liner this morning.”
“Yes, mom,” I replied. I hadn’t been sure whether or not I was going to dress up during the day when I got up, but I now realized that if I didn’t and somehow my mother found out, it could spell trouble for me. My mother was one who was used to getting her way around the house. When she wanted something to happen, my stepfather either helped make it happen or she pitched a fit. When it wasn’t my stepfather who needed to be doing something for her, we faced a number of creative punishments at her hands if we didn’t acquiesce. Most of us had learned long ago it was easier to just go along with what she wanted, lest we face her wrath and also risk bringing my stepfather down on us for not doing what she wanted.
I finished my breakfast and went back up to my room. I grabbed my bra off my dresser, got out a clean pair of panties, and took the sundress from my closet before heading to the bathroom. Setting the clothes down in the bathroom, I went over and turned on the water for the bath. I stripped off my nightgown, and pulled my panties off, removing the panty liner as I did. I folded it in half and wrapped toilet paper around it like I had been told, tossing it in the trash once done.
I stepped into the bath and lowered myself into the warm water. I ran the water until it covered most of my body, then turned it off. I soaked quietly for a few minutes, trying to collect my thoughts. This all seemed so new and different, yet according to my mother this wasn’t the first time I had worn dresses. I looked down at my body, trying to understand how I could pass for a girl so easily.
My body certainly wasn’t stocky or muscular by any means. The sports I tended to do were not ones that were known for big, muscular types of people. I preferred bicycle riding and running to anything else, I tended to use my bicycle to get anywhere I needed around town instead of relying on my parents or public transportation. Because of this, my upper body was fairly skinny. My legs were muscular, but not bulging.
Looking at my crotch, I wondered what I would look like if I had been born a girl instead of a boy. I reached down and tucked my penis and testicles between my legs and held them together. My crotch no longer had anything sticking out, but appeared smooth like a girl’s would be. It was interesting to see what the difference would look like, but it certainly wasn’t comfortable.
I finally stopped thinking about all of it and washed my hair and body. The water drained out of the tub as I stepped out and grabbed a towel to dry myself off. Once dry, I grabbed the clean pair of panties and pulled them on. I reached into the cabinet and pulled out a panty liner, removing the backing from the adhesive strip and throwing it away. I placed it in my panties, and then spent a minute trying to figure out the best way of putting on my bra.
With the bra in place, I looked at myself again in the mirror. I seemed to be doing this a lot now as I tried to get used to the sight of myself in these things. I turned around and looked at my backside in the mirror. While my face and hair before held minor bits of masculinity, from behind I looked just like my sisters did when they were getting ready.
I picked up my sundress and dropped it over my head. I plugged in the curling iron, grabbed the hair dryer and a brush. I wasn’t sure what I was doing exactly, but I tried my best to imitate what my mother had done with my hair the day before. I spent a fair amount of time trying to figure out what I was doing with the hair dryer before I picked up the curling iron and tried to put a few small curls around my face like my mother had.
I found the curling iron to be a lot more difficult than I thought. Even though I had watched my sisters use it plenty of times, not to mention paying attention to what my mother had done yesterday, it was a lot more difficult than it looks when it’s right up next to your face and head. I did as best I could, and finally looked at myself in the mirror, not sure how much better I could do. I unplugged the curling iron and left it to cool, opening my drawer to pull out makeup.
Again, I understood why my mother had suggested I spend time doing this. It wasn’t easy. Putting on foundation and blush wasn’t that bad, but trying to do eye shadow, eye liner, mascara, and lipstick took some doing. I was not used to having to put things that close to my eyes while focusing on them, and it took me several tries. I cleaned my face off a couple of times and started over before I felt I had done a decent job.
The makeup was put away and I grabbed my nightgown and dirty panties, heading down the hallway to my bedroom. I made my bed and placed the nightgown under my pillow to wear tonight, and threw the dirty panties on top of the clothes in my hamper. I reached into the closet and grabbed the wedges my mother had me wearing the day before, and slipped them on my feet. I went downstairs and sat down to watch television for the day.
Around lunchtime, the phone rang. I picked it up to hear my mother on the other end. I was a bit surprised, normally she didn’t call during the day.
“Hi, sweetie,” she said, “what did you decide to wear today, your dress or skirt?”
“Mom,” I protested, “I don’t want everyone where you work to know I’m dressing as a girl.”
“Sweetie,” she soothed, “it’s lunchtime and I’m in my office. Nobody else is going to hear me and if I were to tell anyone, it would only be people I trusted with the secret.”
I calmed down. “I’m wearing the dress today,” I answered.
“Good,” she said. “How was it doing your hair and makeup?”
“That’s going to take some practice,” I admitted. “I had to start over on my makeup a couple times.”
“Well, now is the perfect time for you to practice,” she answered. “Depending on how much you like dressing up and how good you get at this, we might get you more clothes. That does remind me, I’ll have to run by the store on the way home and get you some razors for shaving your legs.”
We didn’t talk much more, she had to finish her lunch and get back to work. I made myself some food, and concentrated on making sure I could walk easily and sit right. I didn’t do a lot through the day besides watch television, there really wasn’t a lot to do during the summer for a kid my age besides hang out with friends, and I certainly wasn’t going to go do that dressed like I was.
When my mother came home, she looked me over and had me come into the kitchen to help with dinner. As we did, she began talking to me.
“You didn’t do too badly with the makeup today, go a little lighter on it tomorrow,” she pointed out. “Remember, you want to highlight your features, not hide them. Too much makeup makes you look like a slut.” I asked about using the curling iron and my hair. “You did fine there,” she admitted, “though you may have held the curling iron on your hair a little too long. You can damage it if you do that. You want to just do the curls around your face and a little bit back, frame your face as best you can with them.”
As we sat down to dinner, she watched me. “You’re getting good at sitting like a girl,” she said. “You made sure your dress was under you and you’re keeping your legs together.” I smiled and thanked her, she continued on while we began to eat. “You seem to be getting used to dressing and acting like this a bit more. You had an erection most of the night on Saturday and had several yesterday, I haven’t noticed you having as much trouble keeping things controlled today.”
I blushed at the mention of this, hanging my head and trying to concentrate on dinner. My mother obviously noticed my unease with the discussion. “Sweetie, it’s a natural thing for a boy once he hits puberty to have them quite often,” she explained, “I know I’ve discussed this with you a bit. Based on how little hair you’ve got down there, it seems like you just may be hitting the start of puberty, so you’re a little later than most boys.
“Not to mention how you’re not that big,” she went on. I really blushed at this, trying to hide my face. “Remember, I’m a nurse, I see these things every day, so this is nothing new to me. Usually, a boy’s penis will get bigger as he goes through puberty because he’ll get spontaneous erections that will eventually cause it to grow. You’re still quite small down there, so there’s a good chance you’ll get bigger. Hitting puberty you’ll begin to ejaculate, which is production of sperm and fluid to help get a girl pregnant. Once your body is mature enough, you’ll find it happens quite often when you masturbate.”
I really didn’t say much, “OK, Mom,” was about all I could muster.
“Honey, there’s nothing wrong with learning about puberty and the changes your body is going to go through,” she stated. “Unless you don’t want me to teach you about puberty for a boy? Maybe I should tell you about puberty for a girl, especially since you’re sitting here looking like one? Should I tell you about menstruation and everything that happens to your body in puberty as a girl?”
“I learned about puberty for me in school,” I offered.
“So you learned about puberty for a boy,” she reasoned. “Did they teach you about puberty for a girl?”
“No,” I admitted.
“Well, young lady,” she finished. “I think it’s time you learned more about being a girl.”
We finished dinner and were doing the dishes as she talked to me about puberty for girls. “There’s a lot of changes that will happen in your body as you hit puberty,” she began. “Your breasts will develop, and you’ll begin to menstruate. This is your body signaling that you’re changing from a girl into a woman and are ready to have children. Normally, for you to get pregnant, a man will shoot his sperm into your vagina…”

I stopped her at this point. “Mom, I don’t have a vagina,” I noted.

She looked over at me and smiled. “I’m giving you the same talk I gave the other girls. You’re standing here next to me dressed as a girl because you wanted to know what it was like to be a girl. Well, this is part of being a girl. You’re convincing enough that you’re going to get treated like one by everyone else, it’s probably good that you get used to being treated like one. You can’t get pregnant, true, but you can have sex with men. You don’t have a vagina, but a man can still have his penis inside you like you were a female, that’s the closest to a vagina you have.”

I understood what she was saying, it was hard to argue. I had been the one who asked her what it was like to be a girl and I had said I would dress up if the clothes were available, so it was hard to complain.

“So,” she continued, “your body normally produces an egg that gets fertilized by a man’s sperm and develops into a baby in your uterus. There’s only a couple days a month that you’re really able to conceive, and the rest of the time is your body preparing for you to do so. The lining of your uterus will build up with blood to accept the fertilized egg, and if there’s no fertilized egg, it needs to shed this lining. This is menstruation, which everyone calls your period.

“Your period lasts about one week, and it repeats on average every four weeks. To handle your period, you can use pads that are more absorbent than your panty liners, or you can use tampons that you insert into your vagina.” I thought about the boxes of tampons my sisters had under the sink in our bathroom and the instructions for them I had read.

“I recommend tampons for you girls just from a cleanliness standpoint. You still use panty liners as a backup in case you have a heavy enough flow that the tampon isn’t enough, but keeping it all from getting spread between your legs and possibly onto your panties is often worth it, not to mention thick pads feel like a diaper between your legs. Also, with tampons, you can do things like swimming where you may have to hold off otherwise. You can’t use pads or panty liners while swimming, they’d just get soaked with water.”

We had finished with the dishes and were now in the living room. My mother hadn’t turned on the television, she was just continuing her talk with me. “Your period is the biggest part of developing into a woman,” she said, “it signifies your body is ready to have children. Having your breasts grow is another part, and your body will change in other ways as well. Your hips will widen some, you’ll get a more feminine body shape and features, you’ll change from being a girl into a woman.

“Of course,” she added, “for you this is all more information. You don’t have the equipment to get pregnant for real. You’re not going to develop breasts, well not unless you want to be put on women’s hormones that is. And you’re not going to menstruate like a woman would. Though now that I think about it, you could be on a monthly cycle to match us, and maybe you should do that. Being a girl isn’t all about getting pretty and looking nice for the boys, a period is a downside that maybe you should have to deal with at some point.”

I looked over at her and thought about this. “You said you recommend tampons for it?” I asked.

She thought about it for a moment before answering. “I guess you actually could use tampons, now that I think about it. Whether or not you use tampons or pads will be a personal choice, but either way, I think it might be best to have you match my cycle. All the girls in the house tend to menstruate on the same schedule anyway, it’s a common thing that happens. I shouldn’t start for another week and a half, so we’ll let you try it then.”

She left it at that, and I was left to contemplate what this was going to mean for me when this time rolled around. In some ways, it was intriguing, in other ways, I was nervous about it. I was beginning to find I liked some of the aspects that came with dressing like a girl, I wondered how much more I would like or dislike as time went on.

We didn’t talk much more before we went to bed. It took me quite a while getting to sleep as my mind mulled over all the things my mother had told me through the evening.

When I woke the next morning, I was cold and clammy. It only took me a moment to realize I had wet the bed during the middle of the night. This was far from a first for me, having been put to bed in diapers until just a few years prior because of my problems with it. My mother hadn’t stopped diapering me because I outgrew the problem, but instead because I had outgrown the largest infant diapers she could find. I still wet the bed quite a bit, it had just slowed down over the last couple years.

I crawled out of bed and stripped off the wet nightgown. The soaking wet panties came off next, I took a moment to remove the wet panty liner so it didn’t make its way into the wash. I grabbed a pair of sweatpants and a T-shirt out of my dresser to wear in the meantime. I stripped my bed down, and piled up all of the wet sheets together with my wet clothing and took it downstairs to put in the washing machine.

As I passed through the kitchen, my mother saw me with the pile of sheets and clothing. “Wet again?” she asked. I could only nod with as embarrassed as I was that I still wet the bed at my age. “Well,” she said, “go put things in the washer, you may as well grab your dress to put in with it, I’ll help you get it started.”

I took things out into the garage and deposited them in the washing machine before turning around and heading back upstairs to my room. The sundress had been hung up, but I understood my mother’s point about washing it. I had already worn it for almost two days, it could probably use a washing. I took it downstairs and into the garage where my mother was adding laundry detergent and starting the load running.

She took the dress from my hands and dropped it into the washer. “I’d like you to wear this tomorrow when John gets home from his trip,” she told me. “It’s a good color for you and you look really pretty in it. Were you going to wear your skirt and blouse today?”

“I guess so,” I replied.

“Well, I hope you’re not going to wear sweatpants and a T-shirt all day, that’s for sure,” she commented. “There, the wash is going, you’ll have to put things in the dryer once they’re done in here. Seriously, I had hoped you would stop with wetting the bed at some point. You don’t need to go back to diapers for it, do you?”

“No,” I said glumly, hanging my head in shame.

She just smiled at me. “You’ve always been my baby,” she soothed, “even with you growing up, you’ll still be my baby. Now, you should get yourself breakfast and then get a shower, you smell like pee.”

She followed me into the house so she could grab her purse, and then left for work. I ate a bowl of cereal, then went upstairs to shower and dress for the day. I went through the same process I had the day before in getting dressed and makeup on. It took me some time to get the buttons on the blouse done up, I wasn’t used to them being on the opposing side.

The rest of my time at home was fairly quiet. I did swap the laundry over to the dryer and then took it out to re-make my bed later. I also hung up the sundress, knowing my mother wanted me to wear it the next day when my stepfather came home.

When my mother came home that night, she had a bag from the drug store. In it were a couple razors and women’s deodorant. “You should shave your legs again tomorrow,” she explained as she handed me the razors, “and I noticed yesterday that your deodorant doesn’t really smell like a girl should, so I got you this. You don’t want to have anything that might let people know you’re a boy under there.”

She told me that night that she would be home from work early the next day, she wanted to make sure that my hair and makeup were looking their best for when my stepfather got home. I went to bed nervous about what the next day would bring.

I prepared as best I could on my own the next morning, and true to her word, my mother was home early from work to check my makeup and hair. She did some touching up, and I was upstairs in my room when I heard my stepfather get home. Now I was really nervous. I sat there in my sundress, not sure how to react, what he might think of me dressed as I was. Shortly, I heard my mother call from the bottom of the stairs for me to come down to show my new clothes to my stepfather.

Nervous, I walked out of my room and met my mother at the bottom of the stairs. She gently pushed me towards the kitchen where I knew my stepfather was waiting to see me. There was no turning back as I rounded the corner and stepped into his view.

My stepfather stood there and looked me up and down. “Oh my god,” he said after a minute, “this is really him? You had said he made a convincing girl, that he really looked good as one, but I didn’t expect this. I think he actually looks better as a girl than as a boy.”

My mother smiled at me. “See, the practice you did over the last couple of days really paid off.”

I just nodded and blushed, looking down at the floor, not sure what to think. My stepfather was the next one to speak. “I had thought he might look like a drag queen, but he really does look like a girl. If he wants more dresses to wear, we can certainly let him have them. You said he’s even wearing panties and bras?” My mother nodded her head.

“Your mother said you wanted to know what it’s like to be a girl,” my stepfather said. “So you like these clothes then?”

“They’re nice,” I admitted.

“Well, your mother and I are fine with you dressing as a girl, especially now that I see how you look,” he went on. “Just remember, this isn’t going to be a secret in the family, you’re not going to be able to just wear these things only in your room. You do look really nice as a girl.”

I just blushed. It seemed like the conversation was over, so I turned and started to walk out of the room. I was a bit surprised when I felt my stepfather’s hand reach down and pinch my ass! My mother told me to go back to my room and she would come talk to me in a few minutes.

“Well,” she said once she entered my room, “it’s not just me anymore that thinks you look like a girl. As long as you can keep this up, I don’t think you have to worry about getting teased, everyone will just think you’re a girl. John was really surprised at how nice you look as a girl, he actually asked me if this might be something you want to do all the time instead of just once in a while.”

“I don’t know, mom,” I admitted, “I’m still getting used to this.”

“Well,” she continued, “in the meantime he suggested we get you some more clothes so you have more choices of what to wear, so I’d like to go out and get you at least a couple more outfits this weekend. Would that be OK with you?”

“Yeah, we can do that,” I agreed.

“John is right, though,” my mother stated. “You do look better dressed as a girl than as a boy. You’ve taken to it like it was natural for you, like you’re really a girl inside. I guess it shouldn’t be a surprise, you were supposed to be a girl when you were born, all of your aunts and uncles all had boys and I wanted to have two girls to even things out.”

I didn’t know what to say about this. It certainly didn’t feel that strange to be in the girl’s clothing, or to be doing hair and makeup, or any of the other things I had learned to do.

“Honestly, you’re not a typical boy. You’re not into sports and don’t really seem to be wanting a girlfriend or anything. John has recognized this for a number of years,” she went on, “heck, he even suggested when we got married that you get a dress to match the other girls for the wedding, he thought you would be cute. I told him long ago about you being in Kristen’s hand-me-downs because you were in diapers so late, those times when you had to go back to diapers during the day for a bit he asked if I was going to put you in a dress.

“So, think about how much you like the clothes and everything, and think about whether or not you want to switch to dressing as a girl all the time.”

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