(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.)
Things continued in their routine as time wore on. I never ran into trouble with other kids at school regarding my dressing, though there were plenty of the jock kids who just needed someone to pick on for their own entertainment and I was often their preferred choice. Even though I often wore the white panties, nobody picked up on it.
When Christmas break rolled around, I was happy to have some time away from school. I wasn't sure what I would be getting in terms of presents from my family, again asking for music from a couple bands I liked but understanding in my mind that it wouldn't be out of place if they got me more dresses and skirts or feminine things.
We usually did dinner with my stepfather's family on Christmas Eve, and that was planned for this year as well. My mother almost always chose clothes for each of us to wear, with the thought that she wanted us to look our best for the inevitable family photographs.
The standard way things went was that we would all sit down for a brunch together as a family, usually with us kids still wearing our sleep clothes, before heading up to our rooms to begin getting ready for the afternoon family time and evening meal together. Once up in our rooms, my mother would come in and pick out an outfit that she wanted for us to wear, sometimes coordinating them so that we wore similar colors.
All of us had enjoyed the brunch together, eating a breakfast specialty from the country that my mother and grandmother had emigrated from long before I was born. All four of the kids sat there in the nightgowns, and once finished, my mother had us clear the table and help do dishes before sending us upstairs.
I had gotten my bed made and was going to sit down and read when my mother came in to decide on clothes for me to wear. She went over to my closet and looked in there to see what was available. Considering I had a couple of nice button-down shirts, I figured she would grab one of those for me to wear, then get a pair of slacks from my dresser.
I was rather surprised when she turned around holding the green and red plaid skirt I had received for my birthday, together with a white blouse. I could only stare in shock as she went over and laid them down on my bed.
"Can't I wear a nice shirt and pants?" I stammered.
"What's wrong with this?" my mother demanded.
"It's a skirt, mom!"
"So? You look very nice in it, it's nice and Christmas-y in color, and I think it will go well with what I want the rest of the girls to wear," she reasoned.
"But, but...," I tried to think of something to say.
"Listen," she went on, "I want all of you to look your best tonight, and I think you will look nicest in this skirt and blouse. We're going to take pictures like we do every year, so there's no reason you can't dress up."
"But everyone else in the family…," I tried thinking of some reason to avoid this.
"Everyone else in the family already knows you're wearing dresses and skirts, and you were told that it wouldn't be a secret from anyone in the family anyway," she interrupted. "This is what you're going to wear tonight." Her tone sounded final, and she started to look unhappy with me.
"But…," I said weakly.
"But nothing," she rebuked me sharply. "So help me, I will make your life miserable if you go pushing me on this tonight." I knew the argument was now over. If I didn't go along with what she wanted, the evening was going to be rough, and she would figure out a way of making life even rougher for me after.
Resigning myself to it, I stepped over to my dresser to start getting things out to change into. "Should I wear hose with the dress?" I asked my mom as she went to step out the door of my room. My mother had bought me some control-top pantyhose in the past couple months with the argument that they would help me 'conceal' the small bulge in my crotch.
"I think that would look very nice," my mother smiled broadly, knowing that I was now going to be following her wishes. She stepped out, and I grabbed a clean bra, panties, and the pantyhose and laid them together with the dress and blouse on my bed, waiting for my turn in the bathroom to shower and begin getting ready.
Once the bathroom was open, I took my turn in the shower, making sure to shave my legs before getting out to dry off. I was fully used to the routine of dressing now—pull out a panty liner, drop it on the counter and slide my panties halfway up my legs, remove the adhesive backing and stick it in place, then slip the bra around my chest, hooking the band in front and rotating it around to slide the straps over my arms.
I sat down on the toilet to slide on the pantyhose, creating a mass of material in my hands so that I could get my toes down to the bottom (and also prevent a run in them) like my mother had shown me. I did one leg, then the other, pulling the top up around my waist. I slipped the blouse on, and then stepped into the skirt, zipping it at my side. I grabbed my nightgown and dirty underwear and padded back to my room, stopping to let my younger stepsister know that the bathroom was now hers.
Once she was done, it became a minor battle in the bathroom for space. Each of us was vying for room in front of the mirror to get our hair done and makeup on. My sister and older stepsister argued for seniority, so my younger stepsister and I waited our turn. While waiting, I spent the time putting a layer of nail polish on my fingernails.
Unfortunately, the nail polish hadn't fully dried by the time the bathroom counter was open, but I lucked out in that my mother came in at that point to see how close we all were to being ready. She took the time to help me get makeup on and put a few curls in my hair while I waved my fingers back and forth in the air to get my nails to dry faster.
We headed over to where my stepfather's parents lived, a small single story house in the center of town. When we knocked on the front door and entered, my grandmother (my mother's parent) had stood up already to greet us. Her husband, Jack, was just behind her, and I could hear my stepfather's parents in the kitchen. Knowing them, his mother was probably fixing the meal while his father was mixing drinks for the adults.
My grandmother and grandfather greeted each of us in turn. I had held back, trying to hide behind everyone else, when I heard my grandmother exclaim, "Wow! You were right, Linda, he doesn't look like your ex now."
My grandmother stood in front of me, and a second later, her husband joined her. "Mom, Jack, this young lady you used to know as Richard, now we're calling her Tina," my mother introduced me.
"I must admit, I wasn't sure about all you told me about how much he looks like a girl," my grandmother admitted. "You're definitely right, though, he completely loses the likeness to his father like this."
"If I had just met her, I would never have known it was actually a boy under there," her husband replied. "Most definitely a pretty young girl."
I blushed at the attention, giving each of them a hug in greeting, before heading in with the rest of the family to greet my stepfather's parents. They too, gave their ooh's and aah's over my appearance before turning back to what they had been working on.
John's mother did speak to me before I could walk away, saying, "Well, certainly not the first time I've seen boys in dresses, but I have to admit, you probably look the best from what I have seen before."
I was curious about this. "You've seen boys wear dresses before?" I asked.
"Oh, my, yes," she answered. "I was a young girl back when the Great Depression hit. There were a lot of families that didn't have money for food, let alone new clothes. There was at least two families on our block that had kids where the girl was the oldest and when she outgrew the clothes they just had the boy wear them. When it was wear a dress or don't eat, it was a lot easier to deal with."
"What did the boys think of it?" I was still curious.
"Oh, they never really liked it much," she continued, "but it wasn't much of a choice for them. I don't think anyone ever gave them any trouble over it, everybody knew just how bad things were in the area."
"At least they had an excuse," I reasoned.
"Your mother says you wanted to know what being a girl was like, didn't you?" she asked.
"Yeah, and I don't mind dressing like a girl a lot of the time, but sometimes I don't want to," I mused.
"Well, there's always things we don't want to do in this world," John's mother replied. "All we can do is grin and make our way through it, we're always stronger in the end."
It was then I heard another knock on the door and more people enter. John's sister came in with her husband and their two children, James and Danielle. My mother came into the kitchen to guide me out and introduce me.
John's sister looked me over as she came in. "My word," she said, "I know you had said he looked like a girl, but I never realized that he looked this good as one." Her husband just greeted me quietly, not really saying much. James sneered at me, while Danielle seemed disinterested. All of the kids were sent to go watch television in the back room while the adults continued their chat in the front room until dinnertime.
It wasn't long before James started harassing me about the way I was dressed. "What are you," he asked, "some sort of sissy faggot?"
"Sorry, you're not my type," was my answer.
The insults and name-calling continued, and I tried to ignore it. Obviously, this wasn't going to deter James in the least, he wanted to get at me somehow. The next thing I knew, he was trying to flip up the edge of my skirt, asking, "You wearing girly panties under there, too?"
I finally had it. I walked out to the front room and sat down next to my mother, who was busy catching up with John's sister. She saw me and asked, "Why aren't you watching television with everyone else?"
"James is being a jerk," I told her, "he's calling me names."
"Well, ignore him," my mother responded. John's sister heaved a deep sigh, apparently James' behavior wasn't anything new.
"I did," I went on, "but when he started trying to flip up my skirt to see my panties I got sick of it."
This was the point John's sister became unhappy. "James!" she called out. A minute later he was out in the front room to see what she wanted. "Were you trying to see up Tina's skirt?"
"Aww, mom," he tried to brush it off, "I was just playing with the little queer."
"And you think trying to get up her skirt is funny?" She was getting upset now. "Maybe I should put you in a dress or skirt for a couple weeks and see what you think of it all! Or maybe that's what you want in the first place?"
"Now, dear, I don't know that's appropriate," her husband tried to soothe her.
"If he thinks this is funny, we'll see what he thinks when he's on the receiving end," she said with finality. "Do I make myself clear?" James could only answer, "Yes, mom," and retreat back to the other room with the other kids.
During dinner, the conversation did turn at one point to my dressing. James had kept quiet, not wanting to upset his mother further. John's sister certainly seemed ready to carry out her threat, and she wasn't going to let her husband stand in the way. John's parents, my grandmother, and her husband though all seemed to want to know more about my future as a girl.
"So, is this going to be a permanent thing?" my grandmother asked.
"We're in the middle of trying to figure that out now," my mom replied.
"Well, you've got my vote for it," she answered.
The holidays were just another step on my road to femininity. Of course I received plenty of gifts that were for my female side, but that was only part of what would occur. I had doctor's appointments, visits with a counselor to discuss my thoughts on actually becoming a girl and help figuring out which way I wanted to go, and spent plenty of time on my own trying to decide what I wanted.
There were plenty of times I dressed up as time went on, from the weekends and holidays when school was in session, to the times I would change when I got home from school. The following summer my mother kept suggesting I could dress up even more with there not being school to worry about.
On top of that, my mother kept me on a monthly schedule to match her cycle, and it got easier to deal with over time. I just began to think about it as a normal part of life, even though I wasn't really menstruating. There was plenty for me to do, and I got really good at doing my makeup and hair, keeping my haircut in a style that could easily be worked either as a male or female style.
Of course there were new clothes added in, from some new school clothes (for my male side), to new dresses and skirts, and underthings to replace those that were wearing out. I got a bikini for out by the pool the following summer, and when we went on a vacation that summer, my mom convinced me to spend the whole time dressed as a girl.
During the next school year, a major upset happened with our family. My stepfather was offered a position in a location halfway across the state, meaning we would be moving at the end of the school year. My oldest stepsister was already in college, so it wouldn't affect her, and my sister was finishing up her senior year of high school, so she would already be moving out. My younger stepsister (a year younger than me) was able to go to live with her mother (just a few miles from where we were at), so she could stay around her friends and continue on in the same school. For me, I had no choice but to follow my mother and stepfather.
One option that was quickly brought up to me by my mother was that this could be a clean start for me to live my life as a girl. Nobody at the new school knew me as a boy, we were going to be a long enough distance away from our old town that we wouldn't run into anyone, and we were moving to a much bigger city where it would be easier to just 'blend in'.
I was told I had to make a decision when we moved. I could throw out the male clothing I had and go to living life fully as a girl, or I could decide to stay a boy. If I decided to become a girl, the doctor would get me on hormones to start breast development, they would get things squared away with the school for me to attend as a girl, everything needed. It was a big decision.
After all of the meetings with the doctors and counselors, I finally made a decision. I sat down with my mother and stepfather and told them what I wanted. "I want to stay a boy."
My mother was a bit upset by all of this. "After all that money and time we spent for you on this? You want to just throw it all away, waste all of it?" she said.
"I'm sorry, mom," I answered, "but while I like dressing up and acting like a girl a lot, I don't want to do the surgery, or live my life all the time as a girl. I like being a boy sometimes, too."
"It still seems like you've just wasted all that money we spent on clothes for you, on the doctor's visits and medications," she pointed out. "Now you want to go living completely as a boy?"
"I'll still dress up," I offered, "I'm not saying that has to stop. But I don't want my body to be that of a woman, I don't want to do the surgeries or anything. I'd rather make the decision now before we spend more money."
"So we'll still get to have Tina around?" my mother asked.
"Yes," I agreed, "I'll still be Tina plenty of times, but I just don't want my life to be nothing but Tina."
"So are you wanting to stop the testosterone blocker medication as well?" she asked next.
"If I'm not going to become a girl, then yes," I said, "isn't that what the doctor and counselor have said anyway?"
"Fine," my mother said, "but we still want Tina to be around."
"She will be," I assured her.
I stopped the medication shortly before we moved. The summer in the new city was much tougher to deal with for me—not only had we moved hundreds of miles right at the end of the school year, I knew nobody in the area, and we were in a much bigger city where there were not so many kids my age living around.
Once I stopped the medication, puberty hit full bore within a couple months. As the new school year started, I found myself dealing with plenty in terms of changes in my body while I tried to cope with the changes in my life as well. One thing this didn't help with was the trouble I had always had with wetting the bed.
My mother still ribbed me about the problem, asking every time she saw me putting things into the washer, "Again? Don't need to go back to diapers, do you?"
Finally, after what was probably almost two weeks of nightly wetting, I was fed up with her bugging me about it. The next time she asked me, I just answered, "Maybe, I don't know."
She stopped, taken aback by my admission. She just looked at me, then turned around and walked away, heading out the door to work. I didn't think anything more of it, and finished getting ready and headed out the door to school. When she got home from work that night, she informed me that she had made me a doctor's appointment.
"What do I need to go see the doctor for?" I asked.
"You've been wetting the bed almost every night," she replied. "If it's bad enough to the point that you think we might need to go back to diapers, then you should be checked out by the doctor to make sure it's not something more serious."
I cringed at the mention of diapers. That was definitely not something I wanted to go back to. With all my troubles over the years, it just brought back memories of being sent to school in diapers and how miserable life was back then. If it was something that the doctor could help with and we could avoid that, I was up for it.
It was a week later when my mom came home early from work and met me as I walked in the door from school. We headed down to the doctor's office and went through the check-in and got taken back to the exam room. The nurse asked, "What are we being seen for today?"
"He's been having problems with wetting the bed every night," my mother announced. I could do nothing but hide my beet-red face in shame.
"Well, the doctor will be in in a couple minutes to talk to you," the nurse said, making a few notes in my chart and then leaving.
When the doctor came in, he looked over the chart, and asked, "Trouble with wetting at night?"
"It used to be just a few times a week," my mother answered, "but lately it's become a nightly thing." Again, all I could do was just hang my head at the discussion.
"Well, it's definitely more common in boys for this to happen, and a small percentage of them have problems even up until they're 18," the doctor explained. "Puberty seems to definitely be a time when it hits worst for a lot of these boys, but I would think he'd be past most of that age already."
"Maybe not," my mother said, "there were a lot of gender questions Richard had, so he was on testosterone blockers until he got it all figured out. He just stopped those a few months ago."
"So he's probably in the middle of the worst of puberty," the doctor surmised, "school just started, any major changes there?"
"We just moved to this area as well, so he's at a new school this year," my mother pointed out.
"Well that's certainly a major change," the doctor reasoned. "So there is definitely a fair amount of stress in his life with all of this, I can see why there's an issue. We'll double check to make sure there's nothing like a urinary tract infection real quick, and then discuss it further."
The doctor left, and the nurse came in to lead me out to the bathroom to pee in a cup for them to check for an infection. About fifteen minutes later, the doctor came back in to discuss the results with my mother and I.
"Well, there's no infection," he told us, "so that's good. Overall, I think this is a combination of puberty and stress, and it will end up clearing up on its own. With the history of this, and everything else that is happening right now, I think it's something you'll outgrow. A small percentage of boys have this happen, so it's nothing new."
"Is there anything we can do about it in the meantime?" my mother asked. "I mean how do we deal with it? Would diapers help?"
I was mortified at my mother's question of putting me in diapers. I was now sixteen, I should not need diapers.
The doctor just looked over at my mother and I, thinking about what she had asked. "I see boys like this a few times a year," he said, "and without fail, they almost always outgrow this within a year or so. Diapers aren't going to make him outgrow this any faster, about the only thing they'll do is keep the bedding dry. There's plenty of techniques to help control it beyond just diapers, like limiting liquids before bed and making sure to use the bathroom before bed."
"We've been doing that for years," my mother replied, "he's had trouble pretty much all his life, it's just getting to be every night right now."
"Well, you're doing what you need to," the doctor answered, "he just needs time to outgrow this."
We left the doctor's office shortly after that, with no follow-up scheduled based on the doctor's thinking. My mother drove us towards home, but stopped along the way at the drug store.
"We need something here?" I asked.
"I was going to get you some diapers," my mother stated flatly.
"But, but…," I started, "didn't the doctor say I would have to outgrow it?"
"Yes,' she answered, "and he also said that they would keep the sheets dry until you did. With as often as you're wetting the bed, we can't keep running them through the wash every day, it costs too much and is going to ruin them really quickly."
I couldn't argue with her about it, I knew she had her mind made up. We went in the store and she quickly found the aisle she was looking for. She spent a fair amount of time looking over the different packages of adult diapers, trying to determine which would provide the best absorbency and protection for my nighttime troubles.
She selected a package that she thought would work and handed it to me. I followed her over to the infant aisle, where she grabbed a container of wipes, a tube of diaper rash ointment, and a bottle of baby powder. "I think that's all we need," she told me, "it's been a few years since we were dealing with this, so we'll see as we go along if we need anything more."
Her comments certainly didn't help things any, and the picture of the smiling baby on the front of the container of wipes only seemed to heighten my unease with all of it. As we walked towards the front of the store, she commented as we passed the feminine products, asking, "You're still on a cycle, do you still have plenty of stuff?"
"I'm good for now," I informed her. I just wanted the day to be over with, to be home where I could hide myself away.
We got to the register and put everything down for the cashier, a lady about my mom's age, to ring up. She looked at me and then at the purchases we were making. It felt to me like she knew why we were buying what we were, and I could only blush. As my mother paid, the cashier bagged the smaller items and my mother handed me the package of diapers.
I picked up the bag, quietly averting my eyes when I heard the cashier tell my mother, "Let him know it's OK, we get boys with that sort of trouble in here quite a bit." While I know it was supposed to help calm me about what was going on, it just seemed to hammer home that people would know I was going to be wearing diapers again.
Once we were home, my mother handed me the bag to take together with the diapers up to my room. I dropped them on the floor in the corner close to my closet, not wanting to acknowledge that we actually had bought them. I think my mother noticed how upset I seemed to be over it, she didn't bring it up at dinner time in front of my stepfather.
When bedtime rolled around, my mother came into my room. "We need to get some protection on you," she said.
"You mean a diaper," it was hard to get the word out of my mouth.
"Yes," my mother admitted, "a diaper. I think you should get to where you can put them on yourself, but for tonight I want to help you so you can get it on right and not leak." She picked up the bag from next to my closet together with the package of diapers and set them on my bed. "Go ahead and get undressed and then lay down."
I was nervous again about being seen naked in front of her, hesitating to pull my underwear down. She chuckled at me, saying, "It wasn't that long ago I saw you naked when you first started dressing up, and it wasn't long before that I was still changing your diapers, so get your panties off and let's get your diaper on."
She had taken to calling all my underwear, 'panties' and I just slid my briefs down and kicked them off before laying down on my bed while my mom opened the package of diapers and pulled one out. She also grabbed the diaper rash cream and powder, setting them on the bed down by my feet.
"This is certainly bigger than the last diapers I was putting on you," she noted. "Go ahead and lift your butt up for me." She unfolded the diaper and slid it under my backside before having me drop back down on top of it. She opened the tube of diaper rash cream and squirted a dollop out onto her fingers before pushing my knees up and back for my legs to be in the air. I inhaled sharply when I felt the cold cream being pushed in between my butt cheeks.
"You don't want to get a diaper rash," she cautioned, "this will help avoid it from happening." She wiped the remainder of the cream off onto the inside of the diaper, then opened the powder and liberally sprinkled some on my crotch, using her hand to spread it around my penis and testicles gently. I started to get erect at the stimulation, which elicited a response from my mother. "Ugh, you really should have at least gotten your testicles removed, it would keep this from happening and look so much nicer."
She wiped the powder off her hands as best she could, then brought the front of the diaper up between my legs and spread it out. She went back and forth, doing up the tapes on both sides, until it was snugly in place. "There," she announced, "you can go ahead and get a nightie on while I put this stuff away."
She was putting everything on top of my dresser, what felt like it was in plain view for anybody to see, while I slipped on the nightgown. I wasn't too happy about having to be in a diaper, I could hear the plastic rustle every time I moved. "Mom," I asked, "I'm not going to have to wear these to school, am I?" I thought back to when I was younger and all the trouble I had, not wanting to go back to that.
"I don't see why you would," she answered. "You're not having problems during the day as well, are you?"
"No," I replied. "It's just I remember you made me wear them to school during the day when I was younger and the kids made fun of me."
"No, sweetie, I'm not going to send you to school in diapers," she soothed. "I don't see a reason to, you're having control problems at night, so that's all you need the diapers for. If you're having trouble during the day, I think that's something the doctor should know about, I just want to make sure you're not wetting yourself during the day as well. As for having you wear diapers during the day when you were younger, that was a long time ago. We did that because you were having so many troubles during the day, and come to think of it, it was when we moved into our last house and you changed schools as well."