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.)

My sister asked me a few more questions as the day went on about my new clothes and dressing up. She wanted to see the outfits my mother had bought me and know about it, it seemed more out of curiosity than any sort of malicious intent. She was a bit surprised at first when I revealed I was dressed all the way as a girl, including the panties and bra. I told her what our mother's reasoning had been behind me having both, and she just nodded her understanding.

The best support I got from her that day was when she found out I had also been bought a girl's swimsuit. The house where she had been babysitting didn't have a pool, so she hadn't been able to swim during the warm summer weather and was looking forward to some time at home where she could. She suggested I get my bathing suit on and we would get in the pool for a bit.

My mother saw us heading out to the pool and stopped me to look at how my new swimsuit fit. She was happy with it (other than the small bulge at the bottom), and shortly joined my sister and I outside as well. My mother didn't swim, she lay out to get a bit of a tan, while my sister and I got some time in the pool. I quickly learned that girl's swimsuits tended to ride up as one got out of the pool around the bottom, and I was constantly putting a finger in the edge of the fabric to adjust it as I stepped out.

I was a bit nervous when my mother suggested I lay out to tan a bit while drying off from the swim. I was worried that the suit would leave the telltale tan lines that one could always see on girl's shoulders when they wore dresses; I was worried that when school started back up someone might see it on me. A quick bit of admonishment from my mother about worrying too much made me realize she wasn't going to give me a choice.

My sister helped me dress while at home the next day, helping me with makeup and hair to get my techniques with both better. On Wednesday morning, when I came down to breakfast, my mother came over to where I was sitting eating my bowl of cereal and sat down across from me.

"My period started today, you should start yours to match," she said, matter-of-factly. I wasn't sure how to respond to this. "You've got pads and tampons both you can try, so figure out which one you prefer to use over the next day or two and let me know so I can get you a good supply of them. And remember, don't leave a tampon in more than six to eight hours." She stood up, grabbed her purse, and made her way out the door for work.

I had forgotten about my mother wanting me to match her cycle. While I did dress up, I had paid little attention to the things my mother had given me the previous weekend, just grabbing a panty liner whenever I was dressing up. This morning, as I went up to my room after breakfast, I figured I should probably wear a skirt or dress, thinking my mother would be looking for it when she got home from work.

Grabbing panties, bra, and the green sleeveless dress I had, I headed to the bathroom to shower for the day. I set down the clothes on the counter and stripped off my nightgown. My boy's briefs seemed out of place with everything else, but I hadn't dressed the day before so I hadn't worn panties. Even though I was finding the panties more comfortable, most days I wasn't dressing I didn't want to put a bra on just to have the comfort of panties.

I finished stripping off my clothes and showered. Once I was out and dried off, I opened the cabinet under the sink to look at what my mother had given me. The pad was thick—probably half an inch thick, I could see why my mother thought they might feel like a diaper between your legs. I set it on the counter and pulled out the partial box of tampons to try and decide which to use.  My mother had left the instruction sheet in with them, so I pulled it out and read through it to make sure I knew what to do.

I looked at the tampons and the pad both. I figured there really wasn't a reason I couldn't try both at the same time, my mother had said that a lot of girls used pads as backup for tampons. I pulled one of the tampons out and ripped open the plastic wrapper to look at it. There were two cardboard tubes, one inside the other, with the tampon itself in the outer one. A string dangled out the smaller of the two tubes, and I read through the instructions one last time.

I held the outside tube between my thumb and middle finger, placing my finger like the drawing on the end of the inside tube. I couldn't reach back behind me through my legs, so I placed one foot up on the toilet as the instructions suggested and reached behind me to spread my cheeks and push it into my bottom. It wasn't easy at first, then I remembered visits to the doctor for my bedwetting over the years. They had regularly inserted a finger into my backside as part of their exam, and always instructed me to push like I was going to the bathroom. I did this, and the applicator and tampon slid in to where my fingers touched my anus.

The inside tube pushed in easily, and I pulled the pair of tubes out, leaving the tampon inside me. I could feel it there, not uncomfortable, more of a full feeling, I certainly didn't find it unpleasant, instead I found myself getting an erection just from the thought that I was mimicking a girl's monthly period. I slid the tubes inside the plastic wrapper and dropped it in the trash, grabbing my panties and the thick pad to stick into place in those.

As I pulled my panties into place and reached for my bra, I understood my mother's complaints regarding pads. My panty liners were something I could barely feel and easily ignore as I got used to them. The tampon I could feel, though I could see myself getting used to having it in as time wore on. The pad bunched up between my legs and I could feel it chafe slightly with every step I took.

I finished getting dressed, grabbed my nightgown and briefs, and walked back to my room. I made my bed and tucked my nightgown under the pillow, then threw my dirty briefs in the hamper. I grabbed my sandals as I wasn't in the mood to fight with the wedges. I walked back towards the bathroom, then headed back to my room as I noticed my sister had gone in to shower herself and shut herself in.

When I heard the door to my sister's room open and close again, I knew she was done in the shower and headed back down to the bathroom to do my makeup and hair. It was only a couple minutes later my sister walked in behind me to get ready herself.

"Hey, kiddo," she said, "cute dress. Felt like getting pretty today?"

"Kind of," I answered. It hadn't been what I had originally thought of, but I knew my mother would want to see me dressing up when I was doing other feminine things.

"Mom wants you to wear it, huh? Can't blame her, it looks nice on you," she commented.

I worked on styling my hair while my sister put on her makeup. She took a break at one point to help me get a slightly better look with my hair, and shortly after we swapped so that she could have the curling iron and hair dryer and I could get makeup on. We finished up, and she double-checked how I looked before heading downstairs to watch television.

As we flipped through the channels, my sister stopped and looked over at me more than once. Finally, she seemed to have her curiosity get the best of her and she began to talk.

"So I gotta know," she began, "you've got tampons, pads, and panty liners in your spot under the sink. Are you actually using them?"

I was embarrassed. I knew this was going to happen, that the girls in the family would figure things out. I looked down at the floor, having a hard time answering. "Yeah," I said quietly, "Mom wanted me to keep my panties clean, so she had me using the panty liners every day, then she said I should see what it's like dealing with a period, so she had me start this morning when she did."

"OK, that's wild," my sister admitted. "I can see how you can use the pads and panty liners, but tampons?"

I turned a deeper shade of red. "Mom said if a boy were to have sex with me, he'd put his penis in the closest thing I had to a vagina, so that's how I use them."

"You've got a tampon up your butt?!?" my sister exclaimed.

"Yeah," I admitted sheepishly. I almost wanted to cry, and I think my sister noticed this.

"Hey, it's OK, kiddo," she soothed. "A period is part of a girl's life, so I guess if you really want to know what it's like to be a girl that's part of it. Heck, I started mine last night, that's when I saw the stuff on your side of the sink."

I looked over at her. I hadn't realized she started as well, I guess we had a bit more of a common bond now. She kept quiet for a bit as we watched the show on television. I found it hard to concentrate on it, my mind kept drifting around to the clothes I was wearing, the fact that I was using tampons and pads, and everything that had changed in my life over the last couple weeks.

At one point during a commercial, my sister looked back over at me and began questioning me more. "So Mom talked about you having sex with boys?"

"Yeah," I answered, "she said she was going to give me the same talk she gave you girls."

"I guess that makes sense," she replied, "though you can't get pregnant." She paused, then asked a new question. "So, are you thinking of having sex with a boy some day?"

"I don't know," I answered honestly. "Part of me likes pretending to be a girl, and I was surprised on Saturday when Mom took me out to get more clothes and it seemed like everyone thought I was a girl. Mom even said there were some boys who were checking way things had started me out."

"Well, you're cute enough as a girl I can see that," my sister responded. "Were they cute?"

"I hadn't paid attention to them, and they were gone when Mom told me about them looking at me," I told her.

"Well, if you're not interested in the cute ones, point them out to me," my sister joked.

We left things at that, and didn't talk much more. Later in the day I was in the bathroom and realized that it was time for me to change the tampon I had in. I reached behind me and spread my cheeks with one hand, grabbing and tugging at the string with the other. I could feel it slide out of me, and I dropped it in the toilet to flush. I opened the cabinet under the sink and pulled out another one of the tampons she had given me, unwrapped it and inserted it.

After pulling my panties back up into place, I washed my hands and left the bathroom. I went down to my bedroom to grab a book to read for something different to do for a bit. While looking across the bookshelf I had (I had to admit I was somewhat of a book nerd), my eyes landed upon the writing journal my mother had given me at the start of the summer. The idea had been that over the summer we could write down our thoughts and have something to look back on as we got older.

I pulled out the journal and sat down at my desk. When my mother had bought me this, I had thought it was going to be a dull summer, but things certainly had changed. There were already a lot of conflicting thoughts going on in my head, and just the new sensations from today were giving me pause. I had never really had thoughts about sex before now, and my mother seemed to think I was hitting puberty late. I didn't get erections often, but I had when I had first started dressing in girl's clothing, and now, the feeling of the tampon inside me gave me regular ones throughout the day.

It hadn't even been two weeks, and life had changed a lot. I began to write down some of my thoughts on the clothes I had on. I had to admit, I really felt that panties were more comfortable than my boy's briefs, though the bra took a bit of getting used to. A dress or skirt was certainly much cooler in the summer heat when it allowed the breeze to make its way up your legs, but the time spent getting hair and makeup ready each day seemed a pain. As for boys, I had been asked several times about them and hadn't paid much mind to that until today. Now, with the new sensations from using the tampons, I began to wonder if I wanted to try doing something with a boy.

I wrote for quite a while and put the journal away when I heard my mother arrive home from work. I went downstairs when she called for me to come talk to her. I walked into the kitchen to find her starting dinner for the family.

"How did the day go?" she asked.

"Fine," I answered. I really didn't have much to say.

"So," she went on, "did you start with a pad or a tampon today?"

I turned red at her line of inquiry. "Both," I admitted sheepishly, "you told me about girls using tampons with a pad as backup, I figured I would try that."

She looked at me and smiled. "That's true, though usually you don't need a thick pad like that for backup when you're using a tampon. If you're having that heavy of a period, something is wrong.

"Even so," she continued, "which ones do you prefer? I'll stop by the store tomorrow and get you whichever you like using better."

"You're right about how a thick pad feels between your legs," I told her, "it's just so bulky it feels weird. A tampon you can feel, but it's not uncomfortable or anything, it's just, it's just there."

"Tampons, then?" she confirmed. I nodded my head.

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