Christy's Diary

By ChristyDancer

Published on Mar 3, 2023

Transgender

Sunday, September 15, part 3

Whew... I'm exhausted and trying to go to sleep, but I promised myself I'd do my diary entries every night before bed so I don't forget anything. Wow... so much to remember from today!

This morning was hot, and so rather than wearing a robe to breakfast, I pulled on a pair of cute pink pajama shorts we'd bought yesterday at Target. I ran a brush thru my hair, and noticed that I hadn't taken off the pink lipstick from the night before. Frankly, I hadn't wanted to, and enjoyed the feel of the lipstick on my lips as I fell asleep. I was sure Mom was going to say something about that, so I patted my lips clean with a tissue and headed downstairs for breakfast.

Sunday was always pancake day in our house, so I dug into my favorites (banana pancakes with warm syrup) and felt happier than I could ever remember. Between bites, I reminded Mom that I wanted to swim in our pool at least one more day before we started winterizing it, and asked if we had any plans for the day.

Mom sat down with her plate, and said, "We need to get you a new swimsuit. Unfortunately, cute girls swimsuits won't quite fit you, but I have an idea about that. We also need to work on your makeup and discuss what you're going to wear to school tomorrow."

I sat bolt-upright at that last thing. "What about school tomorrow?" I hadn't really thought too much about it. Everything was happening so fast. I was having a great weekend, and overjoyed that the girl side of me was coming out and at least Mom and Aunt Lilly seemed to approve and encourage me. I guess I hadn't really thought this thru. Was I really "coming out" as a girl? Was I ready for that? What would everyone say? How could I pull that off? A million questions started swirling in my head.

Mom seemed to read my mind, and said, "That's OK. We can take this slowly. I'm overjoyed to have a happy daughter rather than a sullen, unhappy son. You were actually skipping yesterday at the mall! Chris never skipped."

Mom went on, "But if you're serious about living as a girl, at least around the house, then we need to deal with the fact that, well, how do I say this... whatever bulges you have, they're in the wrong places."

I just hung my head and started to turn red. I'm pretty skinny, and most girls my age who haven't gone thru puberty yet are, well, pretty skinny. But most of them, at least, have some modest boobies showing and none of them have even the small bulge I have in my panties. How will I wear a girls swimsuit and hide that? Am I going to be stuck with wearing boy--shorts to the pool forever?

"So anyway," she said, "after breakfast, let's work on makeup, and then go swimsuit shopping. I have a friend, well, actually she's a friend of Lilly's, who may have a solution in the "bulges" department. Finish eating, go take a shower, dry your hair, and meet me in my bathroom."

I ate quietly, thinking about what the day had in store and wondering what Mom had in mind. I took my shower and quickly blow--dried my hair. The combination of my natural hair body and the great cut I got yesterday morning left my hair falling naturally into a cute, shoulder-length girl cut. Like yesterday, I put on clean baby--blue panties and the cute lacy white bralette we'd bought yesterday, and padded off to Mom's bathroom. Before I left, though, I looked in the full-length mirror in my room an saw the faintest of bulges in my panties. Nope, I figure, that won't do. I hope Mom has a solution.

When I got to Mom's bathroom, she had apparently rifled some makeup from Becky's stash. "You and your sister have nearly the same complexion. Of course, today she wears a lot more makeup than a 14 year old girl should, but I think we have a few items that will help out a bit. I'll do this for you today, and then in the future you can work on this yourself."

First, Mom dabbed just the tiniest bit of very pale concealer on some blemishes near my chin and on my forehead. She took a sponge and showed me just how to spread this out and completely cover any sign that I'd ever had a pimple. Next came some very light foundation powder. For this, she used a big soft brush. She added some light bronzer to my cheeks, also with a soft brush, and then used a very small, stiff brush to smooth out my eyebrows. She dabbed a bit of eyebrow makeup on and worked that in with the stiff brush.

Mom said, "Now, we're going to work on your eyes. This can be the hardest part for a young girl. We're not going to use any eye shadow for day-to-day makeup, but we may add that if you go out to something formal in the evening. For now, we just want to add some mascara and a little liner pencil. With your fair skin color, you should use brown mascara and a brown liner pencil, just like Becky does." Mom did one of my eyes, and then let me take over with the other eye. She did a better job, but I thought my attempt was passable. Finally she had me apply the pink lipstick, and then stepped back to admire her work in the mirror. I was overjoyed -- I was looking at the best version of me I'd ever seen!

Finally, Mom put my hair back with a brown plastic headband that contrasted nicely with my blond hair. "There," she said. "You're just right. What do you plan to wear today?"

I stumbled a bit, and said, "Where are we going? What do you have planned?"

She said, "The lady we're going to see is named Martha. Lilly highly recommends her. She runs a shop that caters to... well... how do I put this... the `trans' community."

"Aunt Lilly know this?"

"Yes, apparently, there is a whole spectrum of folks out there, from drag queens who perform on stage to well known businessmen and politicians who need a quiet place to dress up and just relax, and everything in-between. Many of her customers are straight' men who only want to dress and relax, and many are actual transgender women who are in various stages of their transition." Then she took a breath and went on, "Aunt Lilly said that apparently there are more than a few young women your age who go to Martha for advice and, well, passing' help."

"Huh..." was all I could say. I never really thought about my `transition' outside of my own world. Yeah, sure, it makes sense that there is a whole community out there. I've seen videos on YouTube and seen transition photos on Reddit, and envied all of them. But, I always thought of those girls as living in some distant universe, not right here near me. I found myself getting excited about the chance to be accepted by someone outside of my immediate family.

"When do we go?" I blurted out.

"Well," Mom said, "we've spent all morning getting YOU ready. Give me a few minutes, and we'll drive."

I went back to my room and grabbed a crop-T-shirt and a pair of shorts. Then I pulled THAT off and put on a simple yellow sundress with little white flowers. Then I took THAT off and tried on the romper we'd bought yesterday. Then I ended up with the T-shirt and shorts again. I looked at my makeup in the mirror, but didn't dare mess with it. I touched up my lipstick, though. And then again. And again. Sigh... I was working myself into a frenzy.

Mom came in all dressed and said, "here, put these on." She handed me a pair of espadrille wedges. "I found these in Becky's closet. She won't mind, plus it will do you good to get used to wearing heels. These make it easy to learn."

I strapped them on and stood up. Wow! I suddenly felt 3 inches taller, mainly because I WAS 3 inches talller! I stepped forward and found it was a very different walking experience. My legs were 3 inches longer, and the physics of everything was off-balance. I walked back and forth across the room a couple of times, and saw Mom smiling at my progress.

"If you pay attention," she said, "you'll notice that boys and girls walk differently. Some of that is anatomy, but some of it is practice. Wearing heels give you a jump-start on the practice. Plus, wedges are the safest way to do that. If we go out somewhere fancy, you'll probably wear a pair of kitten heels, and they'll feel a lot more natural after wearing wedges for a while."

"Now," she continued, "let's go get in the car. The day is wasting."

Martha's place was in a remote part of town, fairly far away from the `nicer' neighborhoods. I commented about that, and Mom said, "yes, good observation. Most of Martha's customers prefer privacy. If you were a bank president or city council member who wanted to get fitted for a teddy and a pair of stilettos, you might not want to park in a shopping mall."

We ended up in a small parking lot with only one other car there. "It's Sunday morning, and there's not much traffic. I picked this time on purpose, and Lilly called her yesterday to make sure she was open."

I was beginning to wonder how Aunt Lilly knew so many people in this business, but I kept it to myself.

Anyway, we walked in and I saw a place like I'd never seen before. It was a clothing store of sorts, but very dark, and with racks full of lingerie, sexy dresses, high-heeled shoes, strange jewelry, and what I supposed were sex toys of some sort -- stuff I'd really never seen before, even on-line. I recognized a rack of butt plugs' but had no idea what a prostate stimulator' was. I was exactly 3 days into being openly a cross--dresser, and suddenly I'm in the Disneyland of cross dressing. It was all a bit much to handle.

The only other person in the place was a women about my Mother's age who I quickly surmised was Martha. She came up to us, all smiles, looked at me, and then looked to Mom and said, "so, this must be the Christy I've heard about."

Heard about? Huh?

"Lilly called me this morning to fill in the details. I'm so glad to see you've already got her in heels. Good choice. It will help her posture and overall passing, even when she's wearing flats. Lilly said you had a bathing suit problem? I'm sure I can help you with that, and maybe a few other things, as well."

She turned to me and said, "What sort of bathing suit do you have in mind? Where do you plan to wear it?"

I just stammered, "Well, we've got a pool and I want to swim a few more times before summer ends. I'm not planning to go to the beach or any pool parties, but... sigh... how do I say this..."

Mom injected, "Christy's bulges are in the wrong places."

Martha just chuckled, "Well, Christy, that's why I'm here. You're very fortunate. You're starting at a young age. What are you, 13?"

"Fourteen," I said. "Fifteen in January."

"Huh. OK. That helps. You'll be hitting puberty soon, so let's deal with what we have today, and then we can work on the rest later." Martha pointed to a dressing room just to the left of a small stage. "The stage is so I can get a good look at what we're working on. Go in the dressing room and take off your t-shirt and shorts. Leave on your bra, panties, and shoes, and come out on the stage so I can see you."

I headed for the dressing room, hung my clothes up on a hook on the wall, and climbed a couple of steps to the slightly elevated stage. I pulled apart a couple of curtains and walked out on a short runway, with blazing theater lights overhead and under, and Mom and Martha sitting in a couple of seats to the side as if watching a fashion show.

Martha indicated for me to walk out a few steps, and then motioned for me to turn around. She said, "I like the way the bralette is padded, and we're in luck that there's not much in the way of a bulge there for us to deal with. I have a couple of ideas. Christy, have you ever heard of `tucking tape'?"

"Ahhh.... No. What's tucking?"

Martha just laughed. "Tucking is what we do with your male package to get it out of the way. We're in luck -- you haven't gone thru puberty yet, so we don't have to deal with a lot to hide, and I assume there's no hair down there, right?"

I just nodded.

Martha said, "I've got a great A-cup colorful top with silicon gel inserts that will make your upstairs look like a normal, developing, 14-year-old girl. You'll even bounce a bit. The silicon gel will stick to your skin just a little bit, enough to give it a more natural look. As for your bottom.... I'd suggest a black high-cut bikini bottom with the either a tucking tape or possibly a little plastic insert I've been working with. Let's try the insert for now, but maybe use the tape for other occasions."

With that, Martha went to her swimsuit rack and came back with a very pretty top with the promised silicon gel interior. She also had a black bottom, and in it she'd put a small form-fitting cup that looked like it would press up against my `package'. The outside of the cup resembled the normal mound you would expect to see in a girl's bikini bottom.

"Now, go try this on, and when you come back, if this works, we'll try something else as well."

I quickly went back to the dressing room and put on the black bottoms and the colorful top. The cup fit me pretty well -- not perfectly, but I could see in the mirror that my ugly bulge had been disguised into a girl's mound. The high-cut sides of the bikini pulled up to the tops of my hips and made my legs look longer and accentuated what little butt I had. I was pretty impressed with the results, and felt a lot more confident when I walked out on stage.

Mom and Martha were obviously impressed. Martha said, "that's just perfect. You pass wonderfully. Now, I want you to try this." She pulled out a package labeled `tuck tape kit' and opened it to reveal a stack of wedge-shaped tapes very close to my skin tone. She said, "Now, let me show you how this goes on."

I could pretty quickly see the geometry of the situation, and told her "I've got it. You want me to wear this under my bikini bottoms?"

She said, "No. I've got another idea. Your mom said that you're probably going to want to get dressy and go out to dinner or a show or something sometime soon. You'll probably want to wear a dress and something prettier under it, like a young lady's thong. Here is a little flesh-colored thong panty. Put on the tape and this thong, and change back into your bralette, and come back out here for us to see."

I hurried back to the dressing room, and followed my instructions. The thong was pretty skimpy, but with the tape, I fit into it perfectly. I put my bralette back on, and walked out on the runway like I was a model.

That's when I nearly fell to pieces. Rather than just Mom and Martha, there was also another couple - a boy and girl, probably in their 20's. I fought back the urge to run back behind the curtain.

Martha saw my distress and said, "It's OK. This is Carlos and Juan. They're used to seeing young women model undies."

"Uhhh... Carlos and Juan? I see a Carlos and I see a Juanita, but..."

Martha just laughed, "I called Juanita by her `boy' name just to see your reaction. Juanita is in transition just like you. She's 22, and has been transitioning since she started college. Carlos is her boyfriend, and he's been in here a hundred times with her."

I was till a bit rattled, but everyone smiling and nodding put me at ease. Martha indicated for me to turn slowly around, and I could actually feel al of the eyes focused on my nearly bare bottom.

Juanita was the first to speak up, "She looks perfect. I can't imagine she wouldn't pass completely."

Mom was smiling and nodding as well.

Martha said, "Go put your clothes back on. You might want to keep wearing the tape and the thong just to get used to them. When you come out, your Mom and I will have some more suggestions."

I scurried back to the dressing room, put my t-shirt and shorts back on, and headed out to the showroom. By that point, Carlos and Juanita were shopping in another part of the store, and seemed to be giggling over a rack of collars with small padlocks. Mom was paying Martha, and writing down some notes.

Martha said, "This is the contact info for Dr. Preston. He's great, and works with many of the girls in transition. He handles both the counseling part as well as the pharmaceutical part, so you'll be in good, experienced hands. He was my doc back when I transitioned."

I was struck by that last part. "You transitioned?"

"Yep," she said. "I was a macho male -- wrestling team in college and a different girl in my apartment every weekend. Somewhere along the line, though, I realized it was an empty existence. I was drinking myself into oblivion. I won't bore you with the whole story. I still like girls, but I found out I also wanted to be one. It took years of therapy and counseling, but here I am."

I had felt safe with Martha from the moment I met her, but if it was possible, I now felt even safer. I had a feeling I would be back in her store again soon.

Mom and I drove home in near silence. We got near our neighborhood, but not in it, and Mom said, "I need to pick up a few things from the store. Do you feel up to shopping in a grocery?"

I smiled and nodded. We pulled into a grocery parking lot and I began to hop out of the car. Mom reminded me -- turn first, then sit up like a young lady. She grabbed the cart and made me walk along side. I felt nervous at first, but realizing I was getting no ugly looks from anyone, I started walking a bit more upright and caught myself smiling. The practice walking in the wedges was doing me some good, and I could also focus on clenching my butt together with the thong. We got to the checkout, and the women actually called me "miss". Wow...

One of the things Mom bought was a pack of cherry chapsticks. She said, "For now, you probably can't wear lipstick to school, but it's important that you care for your skin, moisturize, and wear chapstick everyday to keep your lips from drying out. Tomorrow, you can wear panties under your `boy clothes', and we'll see how that goes."

I spent the rest of the day relaxing in the pool in my new swimsuit. I changed back into panties, a t-shirt, and a pair of terry cloth shorts for dinner. Mom and I just chatted and giggled like a pair of girls, and watched old movies until I almost fell asleep on the couch. This was much more relaxing than the way I fell asleep Friday night. Was that just two nights ago? Wow...

Anyway... more tomorrow.

Next: Chapter 5


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