from Richard

(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.)

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."


12-04-2016, 11:50 PM
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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