(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.)
Later that night my mother asked me about dressing for the day. I told her, "I thought you would want me to since I was doing the period thing."
She smiled at me, and answered, "It's certainly appropriate. You should have enough clothes to dress for the full week with laundry being done this weekend."
I changed my tampon before bed, took off my makeup and brushed my teeth. I woke up again the next morning with wet sheets, unhappy with the cold and clammy feeling. As I stripped them off my bed and bundled them with my wet nightgown and underwear, I grumbled slightly. I hated the fact that I still had trouble like this as often as I did. I was putting them in the washing machine when my mother came out to get in the car to head to work. "Wet again?" she asked. I nodded glumly, not really wanting to admit to the problem. "Don't need to put you back in diapers, do we?" I just hung my head at the thought, shaking it to tell her I didn't need to go that route.
After breakfast, I took care of things in the bathroom, including brushing teeth, showering, and another clean tampon. I got dressed, did my makeup and hair, and had a quiet day doing little. When my mother came home from work, she handed me a small bag with a box of tampons inside. "I didn't give you enough to last the full week, so you'll definitely need these," she commented.
The next day, when my stepfather got home from work he had my stepsisters with him. There were similar bits of snickering from them at seeing me dressed as a girl until my mother laid down her thoughts on the matter. I didn't think too much about any of it until I heard my stepfather suggest to us all, "So why don't I treat all of you ladies to dinner tonight?"
Though I had been out once before as a girl, I still found it nerve-wracking. The restaurant was one we had been to many times before, so I was worried I might be recognized by someone on the staff, but it didn't seem to happen. I was mortified when I excused myself to go to the bathroom and my mother asked me if I needed a fresh tampon though. I told her I didn't, and took care of my business.
The following day was Saturday, and with everyone home from being out and about, there was plenty of laundry. My mother would run it all through the washer and dryer, but we would all sit down together and fold it at the end. I hadn't really thought anything about this until my sister and stepsisters started sorting through the pile with me to fold things.
"Whose panties are these?" I heard my youngest stepsister Mindy ask. I looked over to see her holding up a pair of the briefs that my mother had bought me.
"Oh, those are Richard's," my mother answered in a nonchalant tone. "There's probably a bra or two of his in here as well, and some other stuff as well." I turned beet red at this. Even though all of this was out in the open with my father, sister, and stepsisters, it was still rather embarrassing to have the panties and bras being considered part of the 'normal' clothes with the rest of the family. As we finished with sorting and folding the laundry, each of us was given our piles to take to our rooms and put away. This was the first time my feminine underwear had been so open out in front of the rest of the family and I found myself rather nervous as I was handed a pile with the panties and bras sitting on top of it. Somehow, knowing they were mine just made it that much worse.
I took them up to my room and put them away. Even with being in a dress while doing all of this, there were still times it seemed unreal. I grabbed the journal from my bookshelf and began to write some more. I was finding that there were parts of doing things as a girl that were much more difficult than as a boy; all the time spent doing hair and makeup, the attention that had to be paid to how you walk and sit, these were things that were harder than being a boy. However, there were some parts of being a boy that were not easy; you were expected to be tough and emotionless, and were relied on for strength, all things I never seemed to be good at.
I heard my mother calling all of us from downstairs. "Girls, you've got more clothes here. Richard, that includes some of your dresses!" she yelled. I cringed at the mention that these were mine, but it wasn't a surprise. Anything that needed to be hung up when taken from the dryer was usually immediately hung up by my mother as she pulled clothes out, which meant I usually never had anything as most of my clothes had been things that just got folded—jeans, shorts, T-shirts, and underwear pretty much covered my entire wardrobe up until the last couple weeks.
I walked out of my room and downstairs. On the side of the stairs as we walked into the living room, my mother usually hung any clothes of ours that we needed to take up to our rooms. There were a few dresses, skirts, and blouses each for my sister and stepsisters, and I recognized mine among the bunch. I grabbed them and took them back up to my room, passing my youngest stepsister as I walked back up the stairs.
She smiled as she saw me passing holding the clothes in my hand. "Those are cute," she mentioned, "I can see why your mom likes you wearing them." I could only mumble my thanks as I headed back upstairs. I didn't know if she or my other stepsister knew I was mimicking a monthly period like they were, but I figured it was going to come out no matter what.
I hung the clothes up in my closet and sat down at my desk again to write some more in the journal. My thoughts were still a jumble with everything that had happened in the last few weeks, I hoped that writing things down might help me cement in my head my feelings on everything.
There were parts I certainly felt were worthwhile. My mother and stepfather were very accepting of me as a girl, and in a lot of ways I felt my mother was more affectionate towards me. I certainly got more attention from them when I was in a dress, my mother always seemed to want to make sure I looked my best. In a lot of ways, I liked being a girl. There were still worrisome thoughts that invaded my head, however. What would other people around me think if they found out? My father and mother had divorced around when I was six and I had lived with my mother since until she remarried when I was eight. I still had occasional visits with my father, what would he think of me wearing a dress and getting all dolled up?
Friends were another concern. I was a bit of a nerd, so I wasn't in the popular cliques at school and I certainly wasn't one of the jocks. I had a few friends that I had known for several years, only two or three that had been around for more than just a year or two. I was entering high school in the fall, and my parents had enrolled me at a private school where I really didn't know anyone while my friends were headed to the local public high school.
Kids my age were not known for being kind to those who were different. I had certainly had my share of teasing over the years, and the times I had toileting troubles seemed to just magnify that. There had been a stressful period in third grade when my mother had just remarried and I switched schools for the second time in a handful of months together with moving. My toileting troubles seemed to get really bad, and my mother made the decision to put me back into diapers for a short while.
This had almost led me to being removed from the class I had just joined. The principal at the school called my parents in and wanted to have me moved to a special education class because of the diapers. It was only because of the teacher who had seen my academic performance and capabilities that I wasn't sent to that school across town. Even so, the other kids at school were merciless about teasing me for it.
Because of that, I hid any further times I had accidents at school as much as I could from my parents. I didn't want to be sent back to school in diapers, and as I got older I knew just how much worse the kids would be if they found out. The previous year in middle school, I had one teacher who wouldn't let me go to use the bathroom because the end of the day was only fifteen minutes away, and in the time between when I asked and when the bell rang, I started wetting myself. By the time I stood up to head out, the added pressure on my bladder made me lose control. I was already teased for instances like that, I didn't want to imagine how bad it would be if I was back to school the next day wearing a diaper.
At least a diaper could be half-hidden under my pants. Showing up to school in a dress or skirt would have zero chance of hiding anything. I might be able to get away with it one day of the year—Halloween; other than that, it was an open invitation to anyone to ridicule me. Thinking more about it, I might be able to get away with wearing panties under my normal clothes to school, though PE class would make things questionable. If I didn't have PE, I could definitely get away with it; I might even be able to sneak wearing a bra.
I sat back and looked at what I had just written. Was I actually considering dressing as a girl this much, to the point I would wear a bra and panties to school? My mother had commented to me before about people that might hurt me if they found out I was a boy under the dress. That was certainly something I wouldn't argue. Being a bit of a nerd, and also seeming to hit puberty later than other boys (something my mother had also commented on), I wasn't as interested in girls and didn't have much luck with them anyways. This led to me often being labeled as a 'faggot' or 'queer', and the other bigger boys often wanted to play 'smear the queer' at break during the school day. Even with all this, I was actually thinking about wearing girl's clothes to school.
I put the journal away to spend time thinking about things. I hadn't figured things would go like this when I originally asked my mom that question. Now, I had just sat down and been writing when I noticed I had put down my thoughts on wearing clothes like this in places where I normally wouldn't. Did I really want to be a girl?
I finished the week on my 'period' without much further in the way of new experiences. The only thing that came up was as my mother came up to me the day that hers stopped to let me know I was done, she spent a bit of time to let me know that some women would douche after their period had ended to make sure things were clean inside. She said it was something she didn't necessarily recommend for us girls as vaginas would normally have a small amount of discharge to clean themselves out automatically and squirting the douche inside could help start a yeast infection, which was something no girl wanted. She offered to buy me one and let me try it if I wanted, but I declined.
As the week went on, I didn't dress, I had just finished a solid week without a break and pretty much all of my outfits were dirty anyway, so I didn't have much to wear. On Saturday, I decided that I would wear a pair of my panties at least, I really liked the way they fit much better than my boy's briefs and thought they were much more comfortable. After showering, I put them on followed by my shorts and T-shirt. When I was back in my room to put away my nightgown, things just didn't seem right with it all. I realized that I didn't have a bra on, and thought for a minute about it. I tried to consider what my mother what might say if she found out I was wearing the panties but didn't have on a bra. My sisters would wear shorts and T-shirts on a regular basis, and I could hear the argument my mother would make in my head: "A girl your age is going to always be wearing a bra."
She would likely be fine with me wearing the panties under my normal clothes, especially with all my outfits dirty. But she had bought me enough panties and bras that I had enough to last a full week of non-stop wearing before needing washed. She would likely be upset if she found out I was wearing the panties without the bra. I took off my T-shirt, got out a bra and put it on, dropping my T-shirt back into place after. The day seemed to go normally, I was a lot less concerned when my mom wanted to go out and about because I still looked fully the part of a boy, I didn't think the bra and panties could be noticed. What surprised me slightly was at dinnertime.
We were outside having barbecue in the warm summer evening on the patio. We were gathered around the picnic table, chatting quietly as we finished our food. My mother was sitting next to me, and I don't remember what I said, but she reached over to rub my back. I knew right away that her hand went right across my bra strap, she stopped for a moment to look over at me. She rubbed my back a bit more, this time causing my T-shirt to rise up and I noticed she looked down the back of my shorts.
She leaned over to me and whispered quietly in my ear. "Bra and panties today?"
"Yeah," I answered quietly. She left it at that and we continued with dinner.
After dinner, it was time for us to fold the laundry and put it all away. I took my folded clothes upstairs and was putting them away when my mother walked into my room holding my dresses, skirts, and blouses ready to hang in my closet. She walked over and hung them up, talking to me as she did so. "I wanted to talk to you for a minute about all this," she said.
"OK," I looked down at the panties and bras I was loading into my underwear drawer. I wasn't sure what she wanted me to do now. She walked over and shut the door, then sat down on my bed as I finished putting away my clothes.
"So," she began, "you know I noticed you wearing bra and panties under your clothes at dinner. There a particular reason you decided to wear them today?"
I had finished putting my clothes away and sat down in my desk chair facing her. "I kind of like the panties," I admitted. "They're more comfortable than my regular underwear. As for the bra, I figured that it was something I should have on if I was going to wear panties."
"You've had them on all day?" she asked.
"Yeah," I told her, "I just figured it wouldn't be a big deal since it would be hard for anyone to see them."
"Well, I certainly didn't notice until I ran my hand across your back at dinner," she agreed. "I just want to understand why you're wearing these things and how much you like it. If you wanted to wear panties all the time, you probably could, we just get rid of your boy's underwear."
"I don't want to do that," I told her. "I mean, when school starts I don't want to be wearing girl's clothes to school. A bra might get noticed if someone looks close, and even if it was just panties everyone would know when I changed for PE."
"So what do you suggest we do when you're on your period?" my mother asked, surprising me.
"On my period?"
"A girl has her period one week out of every four on average," she explained. "It starts as somewhere around the pre-teen years or early teenage years and usually doesn't stop until they hit menopause, in their 40's or 50's."
"I'm going to be doing it again?" I hadn't thought it would be a regular thing past the week I had just finished.
"You wanted to know what it's like to be a girl," my mother pointed out. "This is part of being a girl. We don't get to decide when or if we have our period. You wanted to know what it's like, this is what it's like."
I just hung my head, not sure what to think or say at this latest revelation. Was she planning on sending me to school in a dress or skirt for that one week per month? This was something that really started to worry me, and I think she noticed.
"Look," she soothed, "I understand you don't want all the kids at school to know about this. I get that, some of them are little thugs and might hurt you or do something stupid. You've worked really hard at being a girl, and I'm really proud of you. I don't think most boys ever get an inkling of what it's like for us, you're trying hard to learn and you'll be able to empathize so much better. I think any girl who might want you as a boyfriend is going to find you treat her really well."
She paused, then continued. "Of course, that's if you're interested in girls. In the meantime, I don't think you should stop with all of this when school starts. We can probably get you some plain panties to wear to school, and I don't think you need to wear a bra for school. I'm not going to make you wear a dress or skirt to school, that's up to you. Would that work?"
"Yeah," I admitted, "just when I'm on my period though, right?"
"On school days, yes," she agreed. "Though you're still going to wear your dresses and skirts other times, right?"
"Yeah, that's fine."
"Good, you look so nice in them I think it would be a shame if you stopped wearing them," she said. "Besides, we spent enough money on getting you all of this, it would be a waste if you just stopped. The thing is though, I don't think you want to stop, do you? What I'm trying to figure out right now is whether or not you want to be a girl for real."
I looked up at her, wondering if she had been reading the journal I had been writing in. I didn't think so, but I was so conflicted right now I wasn't sure what I wanted. "I don't know," I replied, "sometimes I think it would be nice. Other times, I'm not really into it."
"You know, when you first asked me about this, I figured it would be a one night thing and you'd be done," she said. "When you told me you liked the clothes and wanted to see yourself with hair and makeup, that surprised me. I was somewhat shocked when you admitted you would dress up again if we got clothes for you. Over the last couple weeks, I've gotten used to it and I have to admit I like having you as a daughter. I guess this shouldn't surprise me as well. "The thing is, I want to know what you are really wanting with all of this," she continued. "If you want to stop being a boy and instead be a girl all the time, that's something that needs to be addressed. As for wearing bra and panties under your regular clothes, you can do that as much as you want, we don't mind."
"OK, mom," I answered. "Part of wearing the bra and panties today is that you bought me just as much girl's underwear as I already have of my regular stuff, and you said you didn't want it to sit. I kind of figured you might want me to wear it with my regular clothes."
"You can if you want to," she responded, "but I won't make you. I understand that there may be days that dressing up may not be something you feel comfortable with. Still, there are going to be times that we may push you on that comfort zone, like when we went to dinner as a family. So understand that we will want to see you wearing these things, especially with how nice you look in them."
"Yeah, mom, I understand," I replied. She seemed to be done with the discussion, and left my room. She had certainly given me a lot more to think about. While I had been mulling over in my mind and in my writing just how much I liked dressing and acting the part of a girl, I had never really thought about whether or not I wanted to actually BE a girl. I liked several things with the clothes, I liked feeling pretty with it, but I wasn't sure I wanted to make it a complete change-over.
From there, I was a bit surprised when she told me I was going to be expected to continue with a period past the time I had just finished up. It hadn't really bothered me to be using tampons, I had actually found it a bit exciting at first to think that I was using the same things the girls in the family did. By the end of the week, I began to understand it could be a bit of a chore. Now, I was considering how I was going to deal with it once school started back in a couple months.
To be honest, I knew I had already been writing in my journal about how I might get away with some girl's clothing items paired with my regular clothes for school. A tampon was even further hidden than a pair of panties. Still, I knew I would need to carry spares in my backpack, and the thought of wearing panties that whole week was worrisome. My mother definitely had a good idea about getting me panties that were similar enough in color that they might not get seen as different than my regular underwear, I hoped that would work.
The rest of the weekend passed uneventfully, and though I spent a fair amount of time ruminating on the discussion with my mother, we didn't discuss things further. I did get surprised when my mother came home from work Monday night, however. She once again took me aside to talk about things with me.
"I had a conversation with a gal at work today about you dressing up," she revealed.
"Mom! I thought it was just going to be kept in the family," I exclaimed. I wasn't happy about things possibly getting spread around about all of this.
"Don't worry about it, honestly," she tried calming me, "she's a doctor and this wasn't me spilling the beans to just anyone. She's done a fair bit of work with some people who have gender issues, so I figured this was appropriate."
"Gender issues?" I asked.
"Men who want to be women, boys who want to be girls, and vice versa," she explained. "Kind of like where you are right now."
"OK," I answered, "So what did you tell her?"
"I told her about you wanting to know what it's like to be a girl," my mother continued, "and how you dressed up that first night. From what she said, it's fairly common for a lot of boys to try on their mom's or sister's clothes at some point around your age. The difference, though, is that you wanted to see how you looked with hair and makeup, and also that you would dress more.
"I told her about you actually wearing the bra and panties under your normal clothes and she asked if you wanted to actually be a girl, not just pretend to be one. I know that's something you're trying to figure out for yourself right now, and told her so. Even so, she suggested that I bring you in for an appointment with her to discuss all of this," my mother finished.
"OK," I wasn't sure what the end result of this was.
"You have an appointment in a couple weeks to see her," my mother said.
I hoped the next couple weeks would be uneventful. I needed the time to try and figure out what I liked about being a girl, and if I wanted to actually be a girl. There was plenty of time I spent writing in the journal, together with time spent reading back through what I had written and reflecting on it.
There was one day that my neighbor, Kevin, came over to see about doing something one day, I don't remember what exactly it was. He was a year younger than me, and we had been reasonable friends since our family had moved into the neighborhood. We had gone to the same elementary school, but he went to a Catholic middle school the last couple years, though his parents planned to send him to the same private school I would be attending in the fall. We were up in my bedroom talking about getting on our bikes in the next few days and heading into town for something. I was sitting on my bed, and he sat in the chair at my desk. We had been talking for a couple minutes when he stopped and looked over towards my closet.
"Whose dresses are those?" he asked. I shuddered, realizing that I hadn't closed my closet door and he could see my outfits hanging up in there. I needed to think of a fast answer.
"They used to be my sister's," I lied, "she doesn't wear them anymore and needed room in her closet, so since I don't have anything to hang up in mine they got put in here."
Kevin stood up and walked over to the closet, looking closer at the clothes. I saw him look down, then I heard another comment from him. "Doesn't she have her own hamper for dirty clothes?"
"Yeah," I replied, not sure with what he meant. Two seconds later, it hit me. There were undoubtedly dirty clothes in my hamper that just gave me away, whether it was panties or a bra or a dress, I didn't know right away. But I knew I was found out.
"Man, you are so lucky!" Kevin burst out. "These are your panties and bra?" He reached into the hamper and pulled the underwear out. They had been sitting right on top, ready to be seen by anyone who got within viewing distance. "I've got to sneak them from my sister," he continued, "my parents would freak if they ever caught me in them, and you've got your own."
It started to dawn on me what he was saying as he held them up to look at closer. Kevin liked to wear girl's clothes himself. I guess the doctor my mom had talked to was right, that a lot of boys would sneak their sister's things to try on.
"Can I wear them?" Kevin asked, shaking me from my thoughts.
I looked at the ones he was holding up before replying. "You want clean ones?"
I walked over to my dresser and opened my underwear drawer with him right behind me. There on the right side of the drawer were clean panties and bras, I grabbed a pair of panties and a bra for each of us to change into. In a flash, Kevin had his shorts and shirt off, shucking off his briefs to slide the panties up his legs over his already erect member. It took me a moment longer to get undressed and slide on mine, I was certainly faster hooking the bra and getting it in place than he was. Once I had on the underwear, I walked over to the closet and pulled out my green dress to put on. I turned to Kevin and asked, "You want a dress to wear too?"
"So those are your dresses?" Kevin responded. I nodded my head. "That's so cool. I don't want a dress, I just like the underwear." I slipped on the dress and zipped it up, putting the hangar back in the closet before going back to sit on the bed and talk to him more.
"Why'd you get all this stuff?" Kevin asked me.
"I asked my mom one night what it was like to be a girl," I explained. "She said the only way for me to find out was to do it for myself, so she bought me stuff and I've dressed up as a girl sometimes."
"Man, she is so cool," he replied. "My mom would flip over something like that, she wouldn't buy me my own things." Kevin absently rubbed his erection through the cotton panties as he spoke. "With as big in the church as they are, they would have a cow if they found out anything like this."
I didn't say much in response. Having seen his hand rubbing his penis, I was almost transfixed at the sight of it. When he had been naked, I had been able to get an eyeful of his groin before he slid the panties up. He already had a big, bushy patch of pubic hair where I had a lot less and it was much thinner.
As for his erect penis, I could easily make out the outline of it through the thin cotton panties. Compared to me, he was huge. He was a year younger than me, but it certainly seemed like he hit puberty already. I was maybe four or five inches long when I was erect, and maybe an inch in diameter. Kevin was easily double the size in both dimensions. I could hold my erect member in just one hand, for his, I was certain it would take me both hands. I didn't want to push my luck with how things were already playing out with Kevin finding out about these things, so I kept quiet about the makeup and feminine hygiene products I also had for my use. I could see that having a tampon inside me like I did for a week could easily be construed as 'gay' and this might bother him.
Even with these thoughts I looked at the outline in Kevin's panties with wonder. I sat there quietly, thinking about what it might be like to have him in my mouth, or in my backside. What would he taste like if he were to shoot his load in my mouth? Would it hurt to have something that big inside me? I definitely had something new I needed to think and write about. What would it be like just to kiss him?
Kevin began talking a bit more, asking questions about what other clothes my mom had bought me. He was curious to see the one piece bathing suit and nightgowns, but really wasn't that keen on the dresses or skirts. We talked back and forth about it, with him asking how often I got to wear the clothes and who in our house knew about it all. He was a bit surprised when I told him everyone knew and that I had to dress openly in front of the family.
It wasn't much longer until he realized he needed to head home. He seemed reluctant to remove the panties and bra and hand them back to me. He still had an erection as he slipped his briefs and shorts back on, I was almost sad to see his large unit hidden away. I took the panties and bra over to the shelves in my closet and put them to one side.
"You can wear these again next time you come over if you want," I explained.
Kevin got a big smile on his face when he heard that. We quickly went over our upcoming plans, something we had seemed to neglect once we changed clothes, and Kevin said he would be back over in another day or two and we could work out any other details then. I walked him downstairs to our front door and bade him goodbye.
The next couple days, Kevin came over to talk further about heading downtown on our bikes on the weekend. It seemed like he was much more interested in slipping on the panties and bra than actually talking. About the only additional thing I told him about was using a panty liner to keep from getting streaks in the underwear. Kevin confided in me that he had been curious about those once he had started sneaking his sister's underwear, but had never taken one out of fear it might get noticed.
While I was happy to put on a dress or skirt, Kevin never seemed to be interested. It also seemed like he was in a constant state of arousal when in the bra and panties, while I had gotten quite used to it over time and didn't have it happen that often. Of course, with not really having started that far into puberty yet, it could have just been that I didn't have the same level of raging hormones.
I did take the time to write about the experiences and thoughts in the journal I had, not using Kevin's full name but only a 'K' to talk about him. In a lot of ways, it was nice to have someone that I could relate with to some degree. While I could talk to my mother or sister or stepsisters about things related to being a girl, there was still a difference there. With Kevin, while he only wanted to wear the underwear and it seemed to be more of a sexual thing with him, he was still a boy underneath who enjoyed the girly aspect.
From there, I did spend time also thinking about whether or not I would ever want to do anything sexual with Kevin. I don't know that he would want to do anything, but that didn't mean I couldn't think about it. In some ways, it could be any other boy, but for now, after having seen him naked with his large erection, I had someone in particular I could project my thoughts onto. I had never really seen that many pictures of naked women beyond having one of my friends sneak a Playboy magazine for us to look through, so it was a lot harder for me to think about girls or women that way.
In some ways, I wondered if being able to see the real thing rather than just pictures might be biasing me with my thoughts. I certainly looked forward to having Kevin over from time to time so I could get a view of him, but as time wore on, the frequency of him coming over to get into the panties and bra lessened. Once Kevin entered high school, it dropped to almost zero, which may have been a consequence of him finding a girlfriend.
Still, it left me wondering a lot about what I truly wanted.