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Image Copyright © 2012 Tracey Willows

Special thanks to S.L.Hawke for technical assistance with medical details and in this post advice on body proportions.

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The Taylor Project
 

Chapter Eighteen

Saturday night, Dad and Julie were out on a date as was Rick. On my way to get some more juice I’d noticed Grandma had fallen asleep in front of the TV. She hadn’t reacted at all as I walked by. I’d had some opportunities yesterday evening, but I’d chickened out. With Grandma snoozing this was about as private as we were ever going to get. So this was now or never. If I wanted to try dressing as a girl this was the time to ask. The hallway to my room seemed to stretch out like in a dream or a horror movie. Did I really want this? I didn’t think Hailey would freak, but I wouldn’t be able to take it back if I asked her. I could just do nothing. Say nothing. Be one with the three monkeys: hear no, see no, speak no. I’d be found out in time and I’d get put on testosterone and that would be it. Wouldn’t that be easier? Just bury these feelings?

But then I’d never know.

I’d arrived at the end of the endless corridor of doom and there was no man in a hockey mask with a knife waiting to stab me. Instead Hailey sat quietly playing on my computer engrossed in her game of Sims. She had become almost as addicted as me. I could sit down and talk Sims with her and pretend nothing was wrong.

No, no I couldn’t. I don’t know when it happened, but I couldn’t bury it. I had to test it. Just once. If I felt nothing, then I could put it away. If I didn’t do this, I’d always wonder what if. I willed myself to speak and somehow forced out the words. “Hailey, can we talk about something?”

She turned away from the computer screen immediately. “Scott? What’s wrong?”

Hailey abandoned the computer and led me to my bed. I was like a zombie and just let her lead me. We sat down side-by-side and she stroked my back. “What’s going on? You look awful. What happened?”

“I need your help with something, but I need it to be a secret.” The words still wanted to stick, but I was past the point of no return now. I knew Hailey. She’d dig it out of me if I tried to clam up.

“Of course, friends first, friends last, friends forever, remember?”

“Yeah, I remember.” Would she feel the same way after I asked? Too late to stop now. “Would you?... Would you help me dress like a girl?”

“Uh…” Hailey looked stunned, but not angry or judgmental. “Wow, totally didn’t see that coming. I thought you hated the boobs.”

“I don’t know what’s going on. That’s the problem! I want them to go away, but a part of me wonders what it’s like and I just want to do it this one time as a test to see.”

“To see what? I don’t understand. Are you a transvegetable?”

I broke out laughing and couldn’t stop. Suddenly that sounded like the funniest thing that I’d ever heard. “Yes! You’ve got me. I like to dress up as a cucumber!” Really I couldn’t let that one go. I tried to do it with a straight face, but I had the giggle fits and I couldn’t turn it off.

It took a while for the giggles to die down. Both of us ended up rolling on my bed like little kids. Eventually Hailey rolled over on her stomach and propped herself on her arms. “But you’re serious aren’t you?”

Even with the conversation turning back to my dark secret things seemed lighter, hopeful now. I rolled over to match her. “Yeah, I’m serious and not really a transvestite.” I enunciated the correct pronunciation clearly. “A transvestite is a cross-dresser, a man who likes to wear women’s clothes or vice versa. I think I might have a different trans problem. I think I might be transgendered.”

“And that’s different how?”

“It means maybe I’m a girl inside my head. Look, you pointed it out to me. How I like DDR and hanging with you and Cathy and the Sims being like playing dolls.”

“And how we’re both laying on your bed with our legs in the air?”

I hadn’t noticed, but I paused and took in how we were posed. Hailey was on her belly at an angle on the bed. Her legs were bent back in the air and I was mirroring her. “I’m totally laying down like a girl aren’t I?”

Hailey giggled at that one. “Oh yeah, big time. And the Sims, I was right and wrong about that. There is more to it than I thought, but it is a lot like playing with dolls. You know, I wasn’t serious. I was just teasing you before, but this is different. You’re serious. Cathy and I are your best friends and we hang out all the time. Can’t it just be that you’re picking up some of our habits? I mean how can you be a girl in your head? You’re all into Cathy aren’t you?”

“I’m not as much into Cathy as she is into me, but yes I’m into her.” I hadn’t yet worked out how Cathy fit within all of that. “I think it might go deeper than that.” How to explain it though? “Some people are mixed up in the head genderwise. It isn’t something people choose. It’s like being gay or a lesbian. It’s inside you.”

“Ooh, a lot of people at your church including your father and grandmother would have a fit about that. I’m OK with it. We had people like that at my old church. Some of them tried to tell Mom that she needed to go back and do whatever it took to save her marriage.”

“OMG, they did not. Did someone set the wayback machine to the 1950s?” It boggled my mind, but I didn’t doubt her, because my church was majorly judgmental too. “So what happened?”

“We stopped going to church for a while. Not until we started going to yours. Mom and I had a talk about it. We’re giving your church a try, but if it makes either of us uncomfortable we’re out. Let’s get back to this test. How does it work? Scratch that. I get the how. You dress up in girls clothes. What does that prove?”

That wasn’t easy because I wasn’t sure myself. “I’ve just read that often when people are transgendered, they dress up as the other sex and it just feels right to them. If I’m a boy at heart and not just on the outside it will feel wrong.”

“I get it, I think. It’s like kissing a girl to see if you’re a lesbian or not.”

I looked Hailey over. Wow. “Um, is there something you want to tell me, Hailey?”

“Huh?” She blushed. “No, not me. Someone I know. I like boys. Although for some reason you’ve never done anything for me. I think that I friendzoned you from the start. Anyway, OK, I’ll help you. So we’ll have to use my clothes.” She looked me over. “I think they’ll fit mostly. You’re a little taller than me, but we’re close to the same size. How far do you want to take this?”

“What do you mean?”

“You want my Sunday dress or just jeans or somewhere in between and a skirt? You want to this inside out with panties as well as a bra? How about makeup, hair and nails? How far are you going to go with this test?”

“Oh?” I’d seen her Sunday dress. “Not the dress. I want a more everyday look for a test. Skirt for sure, I want something that looks feminine. So maybe one of your pink tops to go with it?” Most of her tops were pink. “I’ll do panties if you don’t mind.” OMG, had I just said that? It was just a test. A lot of the stories had raved about girl panties. It was an important part of the test, nothing more. “Makeup and hair we have to be careful. Nothing that will be too hard to take off. We’ve also got to hurry. I don’t want to get caught. Grandma is sleeping but she might wake up.”

“Then we’d better get started. I’ll be right back.” She disappeared into the living room and returned with her suitcase. “Skirt and pink top? How about these?”

I looked at the denim skirt and pink top she’d picked out. They were familiar. “I think the first time we met you wore these.”

Hailey paused and then nodded. “Yeah, I think that’s right. BTW, that’s another thing girly that you have going on. You notice clothes. Most boys don’t beyond how much skin a girl is showing.”

Great, add another check mark in the t-girl column. “So, bra and panties and um, shoes?”

“Of course, shoes. You can’t have an outfit without shoes. It’s weird thinking about loaning you my panties. I’ve traded clothes with other girls before lots of times, but never panties. They’re more personal.”

“Hailey, we don’t have to do this if it is making you uncomfortable.” I wanted to do this, but I didn’t want to lose her friendship over it.

“No, I’m good. It’s not like I can’t wash them. Besides it isn’t about me being uncomfortable. It’s about whether you are uncomfortable isn’t it?”

I was momentarily speechless because Hailey got it. “Yeah, that’s right.”

“So we go girly. How about my white panties with the little red hearts and my good lacy bra? It will probably be too big for you. I’m a B cup. If I known we were going to do this I would have brought some of my old A-cups. Why don’t you put on the panties in the bathroom? Then come over here I’ll help you get the bra adjusted.”

Chapter Nineteen

On one hand I was relieved. Hailey hadn’t freaked. She was taking it well and helping me. She even was giving me her panties. They where white and girly, spotted with red hearts and weighed almost nothing. Yet somehow while stepping across the hallway to the bathroom they grew heavier until they must have been made of lead. Someone had tied the same weights to my heart. I’d asked for this but now I had to go through with it and that was something else entirely. I took a detour to the living room and peeked in on Grandma. She slept on so I had no excuse to back out.

Then I was in the bathroom with the door locked looking at myself in the mirror. Too late to back out. I took off my jeans. I’d asked for this. I could still leave on my whitey tighties. They wouldn’t show under Hailey’s skirt, but I’d know and a lot of the stories had raved about the silken texture of panties and how they’d just felt right.

I dropped my underwear and pulled on the panties. They weren’t all that different. They were cut higher on my thighs, but they fit me surprisingly well. They did feel a bit softer than whitey tighties, but there was no amazing sensation that I should have been wearing them all my life. In fact they felt a bit wrong, dirty. I could almost hear Dad and Rich and all the other boys calling names at me: sissy, fag, freak, queer, fairy. I hesitated at the bathroom door for the longest time with my jeans in my hands before I decided to see this through. I forced myself out the door and dashed across the hallway to where Hailey was waiting. “I’ve got them on.” I half-expected her to laugh at me.

“I can see that.” Her face was very serious. “Take off the shirt and bra then.”

“Yeah, OK.” Maybe this was all a big mistake. Hailey wasn’t laughing, but I still felt like a joke. I was a boy in panties, a freak, a sissy. I took off my double layer of shirts with no problem. Then I realized I’d made another mistake. Why didn’t I take the bra with me to the bathroom? I didn’t want to strip in front of Hailey. I’m not sure of the logic of that. First off, all I had were fake boobs, not real ones. So as a boy I could show my chest. Even if they were boobs, Hailey had the same equipment. Regardless of what was logical, it didn’t feel right. I pushed those feelings down and ripped off my sports bra. Then I immediately covered my boobs with my hands.

“I can turn around if it bothers you, but I’ve seen breasts before.”

“I know. It’s just...”

“Embarrassing? That’s OK. It’s just a natural girl thing to cover up like that. I do. Even in the girls locker rooms most of us don’t strut around flaunting our boobs. That only happens in the movies. Some girls flaunt, but I’m not one of them. I won’t watch if it makes you uncomfortable.” She handed me her bra and then turned around.

I did feel better when she turned around. I slid my arms through and reached behind me. I felt better covered. Put another check in the acting like a girl column. “You can turn around now.” I was trying to get the clasp done behind my back. It was a lot harder than I expected.

“Turn around. I’ll help you with the clasp.”

I was getting frustrated so I turned around. “OK.”

Hailey stepped in behind me and start hooking up the bra. “There is a trick to doing it yourself. You do the clasp or hook it in front first, then spin it around back and poke your arms through. Probably best that I adjust it this time though. You’re on the tightest hooks, but you’re doing a good job of filling out the cups. Hmm, you’re filling those out pretty well. Maybe you don’t need my old A cups after all. I’m a 32B and this is a bit loose in the cups, but it fits. At a guess you need a 32A, but you really need to be professionally sized.” She paused a moment. “Scotty, they’re not getting smaller. How have you managed to hide these at school?”

“Did you guess I had boobs before I showed you?”

“Well, to be honest I thought you had man boobs. Those oversized shirts and jeans you wear aren’t very flattering. Oh hell with it, they make you look fat.”

I laughed at that. “Better being thought fat than people seeing I have boobs. Most of what I wear are hand-me-downs I got from Rick and they’re too big for me. I’ve got nicer clothes. I just don’t dare wear them most of the time. Except to church and then I wear my jacket over my shirt.”

“Yeah, I get that, but how are you hiding it in gym class?”

“I face the corner to change, only take off my outermost shirt and change quickly. Even the t-shirts I wear in gym are baggy. Everyone has known me for years. I guess they see what they expect to see.”

“I guess people are blind, but you’ve had some luck, too. One slip up and you’re busted.” She paused and then smirked. “Busted. Heh. Anyway, your plan is not going to work. I don’t see how these are just going to go away in two months time.”

I was watching in the mirror and what I saw didn’t look much like a boy. With the panties and the bra I looked like a half-naked girl with a bad haircut. What Hailey was telling me didn’t really come as a shock, but what I was seeing was blowing the circuits in my brain. Why was wearing girl underwear so much more than being naked?

“Hellooo, are you listening?”

What? Oh, my boobs. “You’re right. They’re not going away. I think I’ve known that for a while now. I just don’t know what to do about it.”

“Do you mean about how to tell your dad or whether you are a boy or girl?”

I was still in shock from seeing myself in the mirror. With one question Hailey cut to the heart of something I hadn’t quite admitted to myself. It had stopped being about hiding things until they went away. It had stopped being about growing boobs. That was actually minor compared to the real question. “It’s about whether I’m a boy or a girl now.”

“OK, lets find out then. You’ve got the parts. Well, mostly. Lets make you pretty.”

“Yeah, pretty silly.” The nervous twitter that escaped my mouth was a little frightening. I was feeling a little lightheaded, but even if I was a girl, I wouldn’t be pretty. At best I’d be a boy in girls clothes. Still, she was trying and handling this so much better than I was. “Hailey, thank you. For helping.”

“You’re welcome. So…top next.” She handed it to me. “Cathy will freak, you know. She wants you as a boyfriend and she’s also really… churchy. I still like her, you know.”

I didn’t respond as I struggled into the top. It dropped into place. It wasn’t at all baggy. Hailey had B sized boobs. Should it be larger? Instead it clung to me. The shirt seemed to trick my eyes. I wasn’t that curvy was I? There had been a question about Cathy freaking. “Yeah, she will.” She wasn’t the only one. I was freaking out here myself. I felt like crying. I looked even more like a girl and I wasn’t done. “Would you hand me the skirt?” I asked in a small voice.

She handed it over. “BTW, what did you do to your… package?”

“Nothing.” Some of the stories I’d read had mentioned tucking my penis between my legs. I couldn’t figure out how to do that. It wouldn’t stretch far enough to get between my legs. I looked down. There wasn’t much of a bulge in the front. I didn’t have a hardon. I don’t get them very often. I don’t remember when the last one was, but this was scary not arousing. “That’s just me.”

“But… Nevermind. Put on the skirt.”

I put it on and twisted pushed in the shirt. Just like tucking a shirt into pair of pants. I couldn’t let her comment go. “What did you mean, Hailey?”

“Just that I couldn’t really tell even looking for it.”

So I wasn’t the biggest boy in the world. I knew that from stray glimpses in PE. Not all the kids were afraid to shower. “I’m just starting puberty. It will grow. Girls get boobs, boys get larger.”

“You’ve got the skirt too high. It should be around your hips not up at your waist.”

I pushed it down some, but it would only go so far. “It won’t go any further.”

“It’s not fair you have more hips than I do. Means you probably wouldn’t fit in my jeans anyway.”

“You mean I have a fat ass.” That was what Dad was always telling me. Move my fat ass.

“If you’re a boy, maybe so. If you’re a girl, then you have a cute bubble butt.”

Was that a good thing? Even if I was a girl I didn’t want a huge ass did I? “So my ass is too big for your skirt?”

“Um, not really. You’re a little bit bigger than me, but you’re taller, too. Honestly, for borrowed clothes mine fit you pretty good. My skirt is riding a little high on you, but not that much. Lots of girls wear them like that anyway at school. Tug them up to show more leg and tug them back in place if a teacher wants to do a skirt check. Here, let’s finish the outfit.”

I accepted a belt from her then some brown shoes with a low heel. The belt was a skinny little girly belt which meant it fit the clothes. I could tell what notch Hailey usually used. The hole was worn and I only needed two more notches. The shoes didn’t fit me; my feet were simply too long. I was like Anastasia trying to get her clodhoppers into Cinderella’s glass slipper. I finally gave up in frustration. “Forget the shoes. Tell me, how do I look?”

“I don’t know what you’re feeling Scotty, but you look like a girl. You’ve got mag legs, better than mine. Why don’t you look yourself?”

I knew where the mirror was, but I hadn’t looked yet. I wasn’t sure I wanted to look, but that was the point. Could I pass or was I just a boy in girl’s clothes? I turned to face the mirror and I saw a girl looking back at me. I couldn’t see Scotty at all. Just a girl with short hair.

Chapter Twenty

I stared at the mirror for a long time, but it didn’t change. That was me.

“So this is what you wanted to test. You look like a girl. Did you find out what you needed to know?”

If I was a boy it was supposed to feel wrong, unnatural. If I was a girl it was supposed to feel wonderful, like I was finally being myself. Instead the girl in the mirror scared the shit out of me. She looked so natural. It’s like she swallowed up Scotty and left no trace of him. It didn’t feel good. It felt freaky. This was supposed to be a test, not a one-way trip. “I don’t know what I’m feeling. I thought I’d look more like a boy wearing a skirt.”

“Do you want to go through with the makeup and the hair?”

I was scared to go on, but I was scared to stop here too. “I’ve come this far. We’d better go all the way.” If we stopped now, I might never know. It was scary as hell, but I had to know, one way or the other. “Let’s do this. Makeup and hair. If you can do anything with my hair.”

“You’ve got great hair.”

“Huh, no I don’t. I have haystack hair. It goes everywhere.”

“You’ve got naturally curly hair. Girls pay big bucks at the salon to make their hair look like yours. That’s what a perm is. It makes hair curly. If you go girl, you should grow it out more. You’ll have lots more options with longer hair, straight or curly.”

Grow it out? I’d always done the opposite, kept it cropped short. Except with Dad and Julie dating we hadn’t gone to the barbershop in a while. It was getting a bit long and going everywhere the way it did when it was more than an inch long. Did girls really pay good money for hair like mine? Why?

“I’ll work on it. You’ll see. I don’t have much makeup. Mom doesn’t let me wear foundation and you don’t need it. So I’ll just do your eyes and lips. Hold still.”

I held still as she brushed applied following her instructions. I closed my eyes and opened them again as she was putting on the lipstick. Then she put some stuff in my hair.

“What’s that?”

“Hair gel. Haven’t you ever heard of styling gel? What do you do with your hair?”

“Wash it and comb it.”

“Oh my god, you’ve got great hair, Scotty. You should take better care of it.”

Great hair? And Scotty didn’t sound right not dressed like this. “Call me Taylor.”

“Taylor? Where did come from?”

“It’s my middle name.”

“Oh duh, I knew that. OK, Taylor, what do you think of your hair?”

And there she was again, the girl in the mirror, the girl who was me and her hair looked really different, a bit wet but straighter and in place. It didn’t look particularly girly. I looked like a girl with a butch haircut, but it looked so much better than I’d ever seen it before. “It looks good, Hailey. What did you do?”

“Not much. I’m not a stylist. All I did was use some hair gel.”

It looked so different. Taylor looked so different. “So this is me.” I was waiting for the bells to ring. Instead I heard more of a funeral dirge. I got up and took a few steps. Moving didn’t break the illusion. “How do I look?”

“I told you already. You look like a girl. Maybe when I said that you acted girly, this is what I meant. I was picking up on this and didn’t even know it. How does it feel?”

“Like I stuck a knife in Scotty and he’s gone.” Great, I was talking about myself in third person.

“Just because you look like a girl, doesn’t mean you are a girl. I read up on your condition. You’ve got a shortage of male hormones. If you go to the doctor they’ll give you testosterone shots. You’ll end up looking like your dad and Rick. The clothes are just the wrapper, you know. It’s what’s inside that makes you a girl.”

I laughed darkly. “Oh, I know. That’s what all the t-girls say, but it’s deeper than having Tab A or Slot B. It’s in the heart, mind and soul.” And what was I at the core? Was I a boy with boobs or a girl with a penis? I looked like a girl. “I’m done now. I want to change back.”

Hailey looked surprised. “Already? So did you figure it? Care to clue me in?”

“I found out something, but I’m not sure what it means yet. I’m done now. I’ve got to change back. I’m going to have to think about things.” What if I couldn’t go back? I could remove the clothes but what if that wasn’t enough?

“Sure, whenever you’re ready. This was your idea.

I grabbed my clothes and bolted for the bathroom. I stripped out of everything and put my old clothes back on. My boobs didn’t feel as comfortable in the sports bra as they did the one Hailey loaned me. I didn’t care. I rushed through changing and looked in the mirror and saw Taylor in boys clothes. I still had the makeup on and I washed it out using soap and water. It took some scrubbing. I even stuck my head under the shower and washed out the hair gel. When I was done I stood there staring in the mirror. Taylor was still there mocking me. I could change the clothes and take off the makeup but she was still there.

I wanted to run and hide, but where can you hide from yourself?

I picked up Hailey’s clothes. I shouldn’t mistreat them. I folded them carefully into a neat pile and headed out to see her. She was going to want to talk. I knew it. I headed back into my room and she was sitting there just waiting. “Thank you for helping me. Here are your clothes back.”

Hailey took them and then pushed them back to me. “Why don’t you keep them for a while. Just in case you need them again.”

I nodded. “OK.” That made sense. I was very much afraid that I would need them again, but I wasn’t really wanting to face that yet. I put Hailey’s clothes in the corner of my closet. Maybe I should hide them better, but I’d deal with them later.

“You don’t look good. Do you want to talk about it?”

I felt all shakey inside. Like I was sick with the flu or something. “Can we not talk about it now, please? Can we just play DDR now or something?”

“Yeah, we can do that.” Then suddenly she rushed forward and hugged me. “Scott or Taylor we’re still friends. OK?”

I hugged her back and started crying. “Thank you, thank you, thank you.” She held me for a while and I cried. Then we played DDR and that helped for a while. Maybe it was a girly game, but I was able to lose myself in the music and focus on getting my steps right. However, I couldn’t hide from the way I looked when I had to take a bath and get ready for bed. My boobs were right there on my chest still just as real, but now Taylor lurked in the mirror staring out at me.

 

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To Be Continued...