Blinding Revelations


Blinding Revelations

By Ricky

Some teenagers would get all flustered in the lingerie department – was I stupid or not? I told the truth.

It's about my earliest memory, shopping with my mother. Not that I loved shopping with my mother or anything like that, but I loved running underneath the clothing racks and feeling the fabric rub over my face and caress my body. I couldn't have been more than three or four years old, but it sure felt good.

When I was that small the adults would laugh and think it was cute, so I had even more incentive to run down the rows of soft fabrics while giggling my head off. The adult's amusement gradually turned into toleration and finally to annoyance as I grew up, so I had to abandon the practice but every once in a while I would sneak into my mother's closet and just stand there and let her skirts and dresses caress me. I don't think she ever knew, but with my mom, who can tell?

Mom is a bit of an odd duck. Not that she physically resembles a duck in any way of course , but now that I'm of an age to appreciate feminine beauty I can tell you she would actually knock your socks off. OK, I'm her son and biased, but I see the looks and hear the wolf whistles. She's also a Doctor of Philosophy, a very successful real estate agent, and a force to be reckoned with. She's the daughter of a couple of aging hippies who raised her to be independent and self reliant; she carried on the tradition with me.

Mom is tall for a woman, wears her light brown hair about shoulder length and has a penchant for dangly earrings. I've always kidded Mom about her 'secret identity.' When she's working she wears what might be called power suits, skirted suits that make her look like some high-powered executive at a Fortune 500 company, but at home and relaxing her hippie roots come out and she likes jeans or bright, full skirts. It's those skirts that feel so nice when I stand amongst her clothes in the closet.

Dad? Now you may not believe it, but Dad's an auto mechanic. Yeah, I get that a lot - an auto mechanic and a Doctor of Philosophy? Look, anyone who ever listened to Click & Clack on NPR knows that getting yourself covered in grease and grime on a daily basis doesn't exclude being philosophical. Don't get him going on the existential qualities of modern, computer driven vehicles, you might have to skip lunch when he gets up a good head of steam. He's a hard guy to stop when he gets going.

He's on the short side, a few inches shorter than Mom, but it doesn't bother him. He keeps his blonde hair short because it gets in the way when working on cars, but there are old pictures of him with hair to his belly button. He also has a penchant for dangly earrings in his own ears when he's not working. Between the two of them their bedroom walls are lined with racks and racks of earrings.

Now where was I? I get distracted easily. Oh yeah - sneaking onto my mother's closet to feel her clothes covering my body. Not that I did it every day without fail, but from the time I was old enough to be left home alone I would renew my acquaintance with those soft, colorful fabrics when the spirit took me. I could stand in the middle of her closet for what seemed like hours and just revel in the sensual symphony of fabric and scent it offered. I guess I was about twelve when it finally occurred to me that I didn't have to stand there in the closet, but maybe I could try them on my very own body.

That blinding revelation required me to employ my mother's philosophical attitude: the damn things didn't come close to fitting my twelve year old body. Now, pictures of a little kid playing dress-up can be kind of cute, but the picture of the twelve year old me swimming in Mom's dress is just plain absurd.

I was disappointed, but the idea of wearing a dress as a way of getting the full sensation of those lovely fabrics against my skin was firmly lodged in my mind and wouldn't go away. I cursed, well alright I grumbled, at the fact that I didn't have a sister or a cousin who was near enough my size to provide me with a dress, but I was out of luck. So it went for a couple of more years until I figured out what to do about it.

By the time I was fourteen I was one of those kids with a dozen side jobs. I mowed lawns in summer and shoveled sidewalks in winter. I had been helping in both my dad's shop and Mom's office. With Mom I sometimes answered the phone and booked appointments on weekends; with Dad I learned to swing a wrench and use the diagnostic computer. I could even change the oil and coolant and replace brakes competently. I wasn't so hot at changing tires, Taking after my dad, I was on the small side and lifting those buggers took every ounce of strength I could muster.

The end result of this was I had some money in my pocket. One afternoon, when that odd urge to stand amongst my mother's clothes hit me, it occurred to me that I could actually buy a dress for myself. One that would fit me. Now I don't want you to think that an Angel from Heaven descended to the Earth in a blinding flash of glory to impart this revelation, but it came close to my teenage mind.

I could buy my own dress! A pretty radical thought for a fourteen year old boy, but remember my hippie grandparents, my philosophical mother and my practical father. All that combined in me to produce a kid who looked at life from a rather different perspective. I could buy my own dress! Why the hell not?

Well, I had some money of my own, but nowhere enough to buy the type of clothes Mom bought. Remember, she's a high powered real estate agent; she dresses pretty damn classy. Sure, she isn't averse to hunting for bargains, but even her bargains would strain my limited budget.

Which is where the thrift store comes in. Up until my realization that I could buy my own dress, I had spent much of my money in the thrift store on computer junk and electronics - you can get some great deals on perfectly usable but not up-to-the-minute gear in the thrift store. I had my bike and knew where all the good places were - Volunteers of America, Savers, Goodwill - there were quite a few. So I knew they also had racks and racks of clothes that still called to me, but I was taller than the racks and no longer able to run under them while giggling my head off.

So I had a new goal in life - find a dress that fit me so I could feel what it was like to wear one. The that fit me part presented a problem. I had been looking at the labels on Mom's clothes and the sizes didn't make much sense to me. She had a whole bunch of dresses that fit her, but the size numbers were all over the place. It's tempting to say I get my practical side from my Dad, what with the popular image of a philosopher as a head-in-the-clouds, impractical type, but you don't become a successful real estate agent without a pretty good grasp of how to get things done.

So anyway, when I made up my mind to find a dress that would fit me, I just Googled dress sizes. The answer to why Mom's dresses had several sizes was twofold - some of them were European sizes since she bought them in Europe; the rest came from the good old USA. That's where rampant commercial pandering to feminine egos comes in. Manufacturers seem to think if she's rich enough to pay beaucoup bucks for a high end dress, she wants to think she wears a size six when her body is a size ten. (I get my cynicism from both parents, too.) Really, the more expensive the dress the smaller the size printed on the label. God knows what would happen if they did that in Dad's business. Would the tires on a Mercedes have different sizes than those on a Chevy? Since some women are sensitive about their weight would some sales genius try to change the load rating on the tire so the customer thinks they're driving a lighter vehicle?

Sometimes I wonder how these thoughts get into my head. I started out trying to find me a dress…

Since I was going to be shopping at a thrift store I shouldn't have to worry about the shrinking size phenomenon, so I measured myself and Google told me I'm a size ten. Well, mostly - I don't have any boobs so that part was kind of hard to figure. Which brings me to the Business of Boobs.

By fourteen I had certainly noticed that girls had boobs; even if I hadn't my buddies would have pointed out this natural feminine occurrence in great detail. They didn't have to - I had a genetic predisposition to become aware of this biological phenomenon. They were certainly fun to look at (being properly circumspect about the looking) and there were times when I tried very hard to imagine what they felt like. Since Lexie, my almost-girlfriend and I were not on intimate terms, imagination was all that was available. It was at this point that blinding revelation number two occurred. What would it be like to have boobs on my body?

I suppose it's not too big a jump from a boy wanting to wear a dress to a boy wanting to know what it was like to have boobs, but until I realized that I could actually wear a dress I had never put too much thought into the subject of boobs on a personal level. For damn sure I had put a great deal of thought into boobs on girl's bodies, though. This whole thing was getting rather more complicated as I considered the practical side of wearing a dress.

At this point you might be wondering if I felt guilty or ashamed of being a boy who wanted to wear a dress. The answer's easy: nope. For a start, remember my hippie grandparents. They had taken me to several Folk Festivals where it was not at all unusual for male square dancers to be wearing colorful printed skirts. Dad the auto mechanic wore earrings (two of them - he claims he would be unbalanced if he only wore one) when he wasn't working. Both my parents believed wholeheartedly in a gender-neutral policy when raising children, even if they only got one of me to practice on. Dad's sister is rather butch, I've never seen her in a dress or skirt. Once again, from my more mature perspective as I'm writing this, she is a good looking woman, but she just didn't like dresses or skirts.

By fourteen I had long since gotten the 'birds and bees talk', I had a fine theoretical knowledge of the difference between men and women even if I hadn't had any opportunity to discover the practical implications. In other words, I knew that wanting to wear a dress was certainly not mainstream, but it didn't bother me in the least to have such thoughts.

So, back to the story. I had a goal - find a dress, I had my size - 10, I had a supplier - the Savers store on Marketplace Drive, I had money in my pocket, I had my bicycle; I was ready to buy a dress. At least I thought I was. Thus, when I found myself standing in front of the dress racks one fine Saturday morning, I realized I didn't know squat about fashion. It's one thing to stand among Mom's dresses and soak up the feel of the fabric; it's something else entirely to find something you, a fourteen year old boy, would want to wear.

Since this was a time before phones with Internet capability were ubiquitous, I couldn't resort to my old friend Google for a quick course in lady's fashions, so I just pawed through the racks looking for something I liked. Naturally enough, given the origin of my desires, I operated on feel as much as sight. After a few minutes of searching I found a nice green dress that was made of a sensuously soft fabric. I'd like to describe it to you in detail, but this all happened a long time ago, (we were all freaking out about Y2K at that time) and the details escape me now - it was a green dress and all I wanted was a dress.

Despite my gender-neutral upbringing I realized that most people would frown on a boy wearing a dress, which led to blinding revelation three: I couldn't just take the thing into the changing room and see if it fit. I had a good bit of cash for a fourteen year old, but not enough to be able to buy a dress that I couldn't wear. The size tag agreed with what Google had said I needed and it looked about right, but I really wanted to be sure.

Once again my practical side took over - I went over to the boys clothing section and randomly selected a couple of shirts and pants, piling them on top of the dress in my cart. At the changing booths I just grabbed the whole pile and went in. I hung up the boy's stuff and stripped off my own boy's clothes, removed the hanger and stuck my arms into the hemline, raising my green prize over my head where it promptly stuck on my too wide shoulders and refused to continue on down my body.

There's an old song that says Big Girls Don't Cry - so what if I wasn't really a girl or all that big; I wanted to cry. I wiggled my way out of the dress, put my own clothes back on again and returned the clothes to the racks. Then, using the too-small dress as a guide found one a bit bigger in blue. This one was knee length with a high neckline, obviously for someone on an important date or some semi-formal occasion. I loved it and, throwing caution to the winds. As the store was pretty empty, I just took it to the changing booth.

This one fit! When I felt the dress slide down over my body I had to sit down for a minute and wait for the sheer sensual pleasure to lessen enough so I could stand up again. That pleasure was lessened when I looked in the mirror and saw an obvious boy in a dress, but it still felt magnificent on my body. At that moment I resolved to follow my Dad in having my ears pierced. My hair was a bit longer than most boys wore it (no doubt the influence of my grandfather, who had grey hair down to his waist) but shorter than many girls.

Then there was my face - I didn't have 'chiseled masculine features' but I didn't have a face that would launch a thousand ships, either. Would makeup help?

It suddenly hit me that this whole thing was getting out of hand. All I had wanted to do was see what it felt like to wear a dress, but here I stood thinking about fashion and makeup and… needing a bra so I could look like I had boobs. I was higher than a kite, (if you'll pardon the cliché) my brain addled and racing with the possibilities of what I hadn't yet learned to call crossdressing.

The lady at the checkout looked like she wanted to ask why I was buying a dress, but she just rang it up and put it in a bag. I tucked my treasure in my bike's saddlebag (it locks, by the way, you learn pretty quickly that some people have no respect for personal property on a bike) and went across the street to the Wal-Mart.

I must have still been high from buying my own dress, because I headed right into the lingerie department without a second thought. Hell, this is Wal-Mart - if they sold whole cows no one would blink if you threw a side of beef, dripping and bloody, into your cart and toddled through the registers. Well, maybe the guy who had to clean the floors might object, but a boy buying a bra, ho-hum!

That is until I arrived at the lingerie department. It's one thing to know you should have a 36 bra band (of course the cup size was negotiable since I would be stuffing it with something.) but I just kind of froze when I was confronted with rack after rack of bras. I mean, there were red ones, blue ones, purple ones, sports bras, lacy bras, long bras that would cover a girl's navel, skimpy bras that would have a boy just waiting for her boob to pop out of the bra. How the devil did a girl decide what bra to pick, let alone a confused but determined boy?

"Hey Kyle, whatcha looking at?"

That was all my fourteen-year-old self, frozen with confusion and overwhelmed by feminine froth, needed - a panic attack on top of utter confusion! My brain, sluggish as ever under stress, identified the voice as Lexie, my almost-girlfriend.

Almost-girlfriend, you ask? Well, we hung in the same crowd, usually ended up near each other while we were hanging, and I liked her a lot. Maybe you could call us best buddies, we could tell each other pretty much anything without feeling too stupid and it helped that Lexie had a whimsical sense of humor. We had never been on anything you could call a date together, but you could say we were growing very aware of each other. There had been a couple of very tentative groping sessions in the back room at parties, so yes, my fourteen-year-old self naturally wondered about sex and what could happen between us.

Lexie could be easily described as bouncy! She was a very enthusiastic creature, often given to bouncing with her enthusiasm, which did very interesting things to my developing libido as her breasts described fantastic arcs independently of the rest of her body. Her figure was Rubinesque and her mind as sharp as her body was round.

But back to the story. I think it was Mark Twain who said the best way to lie is to tell the truth badly. I didn't really care who authored the quote, but that's the course I chose.

"Hi Lexie. I just bought a new blue dress and I'm trying to find the perfect bra to wear with it. How do you girls do that with all this stuff to choose from?"

Now there were two of us in a state of confusion. The part of me that wasn't in a panic was snickering at the look on Lexie's face, but there was a part of me that was kind of hoping she could help me find a bra. I wonder if Lewis Carroll felt like this when he started writing about Alice? If a white rabbit came hopping by with a teapot it wouldn't have phased me in the least.

"You're looking for a bra?"

"All I have to do is open my eyes and I can't help looking at bras at the moment."

"Let me rephrase that, Kyle. You're here to buy a bra. Do I have that right?"

"Uh… yeah."

"You're one strange puppy, Kyle. Is it too personal to ask you why you want a bra?" I might point out that you haven't got any boobs."

"Really, Lexie, have I ever been so gauche as to point at your boobs?"

"You've always been a gentleman, even when you stare at my boobs."

How did I end up discussing boobs with a girl? Her boobs, my lack of boobs, anybody's boobs!

"You still haven't answered the question: why does a gentleman such as yourself want to buy a bra?"

"I told you, I need it for the new blue dress I just bought."

"You bought a blue dress?"

Mr Twain - or whoever it was - missed the mark. I told the truth, and I can say with complete honesty I did a very bad job of it, but Lexie didn't fall for it. Maybe it's my honest face? Anyway, I just plunged ahead recklessly.

"Right. I just said that."

"I heard you, but I'm having trouble with why you were buying a blue dress. Are you going into politics or is there a girlfriend somewhere I don't know about?"

Remember, this was a time when everyone was obsessing about Monica Lewinski's blue dress. That hadn't even occurred to me when I got the thing.

"Not really, I don't think there any suspicious stains on it. But I kind of like the idea of you as a girlfriend, so I’d like you to be sure you really don't have to worry about anyone else."


"Sure. I know neither of us is allowed to date yet, but maybe you'd be interested in being my girlfriend?"

"Kyle, you're one weird dude. Who else would ask a question like that in the middle of the lingerie aisle?"

"Well, it wasn't like I planned it…"

"Anyway, you're changing the subject. Blue dress?"

"Uh, yeah…"

"So just who is this blue dress for?"

I had a bad case of motor-mouth. This was supposed to be a secret mission, no one was going to know about my strange desires. Now here I was telling Lexie all about wanting to wear a dress! I couldn't stop myself.

"Uh, me?"

"Kyle, you're one weird dude!"

"You said that already."

"Yeah, just after you asked me to be your girlfriend. Doesn't that seem like a strange combination of events?"

"Well, I guess it is. You kinda surprised me."

"And like you didn't surprise me buying a dress? A blue dress? And a bra?"

"I guess that does seem pretty weird. Like I said, I hadn't planned on telling anyone."

"So what were you planning to do?"

"Buy a bra. I just didn't realize there would be so stinkin' many of them to choose from!"

"Typical male."

"Typical? Me?"

"You know what I mean!"

"Strangely, I do. Even if your average boy doesn't usually go shopping for bras. I need help."

"You have that right! I'm not sayin' just what kind of help…"

"Thanks, I think. How do you decide what kind of bra you need?"

"Depends on what it's for. If you're exercising you want a sports bra - one that squashes these puppies flat so they don't bounce. (I told you she was bouncy!) If you want to get your boyfriend howling you pick one that really makes them bounce. If you're just going to school or something then a plain, white cotton bra makes sense. Then sometimes a girl likes to know she has something sexy under her blouse that no one knows about."

"I didn't know it was so complicated."

"We women like to have an air of mystery about us."

"You've succeeded. Look, would it gross you out if I asked you to help me find a bra?"

"You already did. Anyway, I'm gonna be too busy laughing to be grossed out."


"Actually I think it's kind of cute. You really want to wear a bra?"

"The dress just doesn't look right if you don't have something on top."

"This is no doubt the strangest conversation I've ever had. You going to tell me why?"

"Maybe later, the middle of Wal-Mart isn't the best place to bare my soul."

"You've got that right. So, do you want to go for sexy or sweet?"

"Somewhere in the middle?"

"Lacy then, but not ridiculous?"

"I can't help feeling ridiculous, but yeah - that sounds right."

"You don't happen to know your size?"


"Whoa… Really?"

"The Internet can tell you anything you want to know."

"And so had you, buster. I'm looking forward to finding out why I'm doing this."

"If I can figure it out you'll be the first to know."

"You going to try it on?"

"I suppose I should but…"

"Yeah but… Pick one out and I'll carry it in and help you try it on. Nobody's going to look twice if I go into the changing rooms with a bra."

"You're gonna help?"

"It's not like I'm going to try it on with you watching, at least not yet. I've seen you before; you guys bare your non-existent breasts when you go swimming."

While we had been talking I was scanning the racks of bras, looking for something that might go with my blue dress. Hesitantly, I pointed to a light blue one with just a little lace around the cups.

"I kind of like that one."

"So do I. I wouldn't mind wearing that one myself."

"Matching undies? How cute."

"Our little secret? Are you going to be my boyfriend or my girlfriend?"

"Maybe like I could have a secret identity?

"If you're going to be wearing a blue dress it might be a good idea not to do it in the middle of the road."

"Yeah, I hadn't planned on telling anyone, but you just sort of happened."

"I didn't just sort of happen, my parents were very deliberate about it when they decided to make me."

"You know what I mean!"

"Yeah, I stumbled on a little lost boy amongst the bras. So if you got the nerve let's see if it fits you."

"Uh, you OK with this?"

"I'm curious, and I like sharing a secret with my boyfriend. Or maybe girlfriend?"

"Do I have to decide now?"

"Now for the bra, later for the boyfriend part after you tell me why you want one. Let's go into the changing booth, Kyle."

There wasn't much dialogue to report, since we mostly looked at each other and laughed a lot while I put on the bra. Luckily they were changing booths with complete doors, not those silly things with a couple of feet of open air on the top and bottom to discourage shoplifting. Actually, putting on a bra wasn't hard at all. Remember, even in the early days of the Internet it wasn't hard to find porn, so I had seen women undressing for the camera in a number of interesting ways. Sometimes they even put their bras back on after the act while reciting some stilted dialogue. It looks a lot easier than it is to connect those snaps on the back, but after a couple of tries I managed it.

Even though I was really embarrassed to have Lexie helping me, once I had the bra on me it felt… right. Strange, but comfortable.

"Earth to Kyle… Earth calling Kyle… Come back, Kyle!"

"Uh, yeah?"

"You're just standing there with a contented look on your face and your brain a million miles away."

"It feels… right. I never would have guessed. Uh, does wearing a bra feel like that to you?"

"Jeez - I gotta wear one or it hurts. It's not like it's a mystical experience or anything…"

"I guess when you have to wear one it wouldn't be the same."

"Look, if you want to look like you have boobs, and I still don't know just why you do, then you're going to need a bra even more than I do. You just don't need it because you were born that way."

A look in the mirror told me she was right - without boobs, the cups just sort of hung there, looking forlorn.

"I think you need a visit from the Boob Fairy, Kyle."

"Is there a 1-800 number I can call to schedule an appointment?"

"If there was I would have used it long ago."

"Well, she seems to have found you even if you didn't call."

"But she took her own sweet time doing it."

"It was worth the wait."

"Thanks, I think. Anyway, while I was waiting I learned a few tricks to, umm, fill things in until she worked her magic. A little padding goes a long way."

"I think I'm going to need more than a little…"

"You're in luck, fiber-fill comes in bags in the sewing department."


"Yeah, the stuff my Mom uses to stuff the toy animals she makes. Soft and fluffy and, if you're careful about it, not too lumpy in a bra."

"Thanks, Lexie. I was wondering what to do about filling the cups. You're a sport."

"And you're kind of cute in a bra. You really want to be a girl?"

"Not really, I like being a boy just fine but I've always loved the feel of dresses and stuff like that. I only just realized I could buy one of my own to find out what it feels like."

"So buy the bra already and let's go over to the park so you can tell me why. And I guess it’s going to take a little while since there must be quite a lot to this story that you’re going to be telling me."

So that's what we did


I guess I was lucky that Lexie was an independent sort - she had ridden her bike just like me. I don't know what I would have done if her mother had driven her and she wanted to be in on our conversation.

I don't want to think about that, even a decade or more later. Let's just skip to a table in the nearby park, where I stammered out the story I just told you, but far less coherently. She had lots of questions, but I found answering her questions helped me understand just what my nebulous desire to find out what wearing a dress would feel like was going to lead me.

If I had learned anything from my parents, nebulous desires don't sell houses or fix cars. You need to understand the subject in depth if you were going to succeed. Like most bits of sage advice it was simple to state and a bloody big pain to put into practice. Lexie made me think about what I had to do if I were going to do this right.

An hour or so later we were co-conspirators in the grand plan to let me have a peek into the world of the feminine. When I got home I stashed my purchases away and dreamed of what I was going to do. Well, I did try them on and stuffed the cups, but my folks were home and I was too nervous to wear the dress for more than a few minutes before reluctantly hiding it away.

And dream was all I did. Remember how I told you what I did to get my own spending money? Well, until I wanted to carve out some time absolutely alone it hadn't occurred to me how much time I spent working in one place or another. Even with school off for the summer I had so many commitments it was a good week later that Lexie and I both had any time to let me try on that dress.

The first hurdle was just where could we go to let me dress up? No matter how liberal your parents are they were bound to have objections to letting a fourteen year old boy and a fourteen year old girl remain alone for a considerable time. Then, when you figure that their chosen activity includes the boy removing his clothes… You get the picture, I'm sure.

The only workable place was in our family room one quiet weekday. I had finished mowing all the lawns I had contracted for and Lexie was free. No way was I going to invite her to my bedroom; no way I could explain to my parents if they came home! If disaster struck I could retreat to the downstairs bathroom and change while Lexie made polite conversation with all her clothes on.

Our parents weren't the only ones who would have second thoughts - do you have any idea how embarrassing it is to take your clothes off with your girlfriend watching? (That part had been settled, more by her than me. She was now my girlfriend.) Especially if she has no intentions of taking off her own clothes? Even more especially when she started humming The Stripper when I removed my shirt! If there's one song that every generation knows that's the one, even if it started out when my grandparents were young.

"Hey Kyle, did you know that your whole body turns pink when you blush?" Lexie inquired with a grin.

"Gee, Lexie, I didn't know that. Thanks for pointing it out."

"No problem! You just going to stand there or you going to put on your bra?"

"I've always been a fan of Ben Franklin."

"Huh? What's he got to do with it."

"Didn't you learn about old Ben's air baths in history?"

"Give me a break!"

Yeah, Ben Franklin was big on air baths. Like he would run around without any clothes for the therapeutic value of it."

"Forget it, Charlie - I'm not likely to be taking an air bath!"

"I didn't mean…"

"Right, so put on your bra. Cold feet, Kyle?"

"No, I just… well… help me with the snaps?"



That was the sound of the wedgie she gave me.


"Some boys think that's what bras are for, you know."

"Not me!"

"Yeah, you just want to wear them."

"Well, it is kind of fun."

"Weird! You been practicing?"

"A little bit. Hard to find time alone most days."

"Poor Kyle, such an active social life! How are we going to find time to go on a date, boyfriend?"

"I thought your folks wouldn't let you date until you were sixteen?"

"They won't, so we just call it hanging out or chilling when they ask."

"Aren't you the sneaky one!"

"Yup. I even have a good reason for hanging out with a half naked boy wearing a bra if we get caught."

"You do?"

"You're my science project in changing gender roles."

"That's science?"

"Psychology. Sure!"

"Well, somebody needs a shrink."

"Says the half naked boy wearing a bra."

That's when she kissed me. For a little while I completely forgot about anything else. My first serious kiss, not some peck-on-the-cheek with Mom or Auntie, but a full-blown romantic kiss with a willing girl. Sure we had kind of pecked at each other in the dark at a party or two, but this was… Back then I would have used earthshaking or shattering. Today? Well, today I haven't changed my mind.

"Mmmm… nice!" I said.

"Yeah!" She agreed. "You better get dressed or I can't be held responsible for what happens."

"If I said you had a beautiful body would you hold it against me?" I warbled. Can I help it if Dad likes classic country music?

"Hey! You can sing! But no you can't - we're working on your body right now so no more distractions."

"Oh, yeah."

"Here," she held out the bag of fiber-fill. "Get stuffed!"

So I stuffed my cups and put on my blue dress, wiggling a bit to get it into place. Then I modestly removed my shorts from beneath the dress. Before you ask, I wore briefs, not boxers. Boxers suck.

"You're cute when you shimmy, Kyle."

"You're not bad yourself."

"No drooling, we're supposed to be exploring your femininity."

OK, I kept my mouth shut and ignored the straight line. It was hard though.

"Sit down," she ordered, "and let me see if I can do something with your hair."

Like I said before, my hair was about shoulder length, not as long as many of my girl classmates but longer than many of the boys. I really enjoyed having Lexie play with my hair. Let's face it, at that age any excuse to have my girlfriend touching me was welcome, but having her stroke my hair was heavenly.

It also made me feel rather feminine - this was what I imagined women went through in a hair salon. Even though barber shops were starting to die out in favor of 'unisex salons' back then, Dad always took me to the barber shop when I need a haircut. Jake the barber teased me about my long hair, but he did a nice job on it.

But it sure didn't feel like this when he worked on my head!

"OK, you can look now."

I had been spaced out with my eyes closed. The hairstyle helped, I was not so obviously a boy in a dress. I now had two short pigtails, one on each side of my head. Too bad I wasn't two years old, I would have been adorable.

"Cute. It looks better, doesn't it?

"Some. You game to try some makeup?"

"I guess…"

"Hey! You're the one who wanted to look like a girl."

"I wasn't thinking so much of how I looked as how the clothes felt."

"So how do they feel?"

"Wonderful, like this is how I should have been dressed all my life."

"I'd say you were weird but I've already said it too many times."

"You aren't grossed out?"

"No, not really. It's kind of fun to play dress-up with you."

I'll never know how I managed to control my motor-mouth after that remark, but I did. A smart remark right then could have blown the whole relationship.

"You think makeup would help?"

"It can't hurt. I came prepared, you know."

"You did?" Again with the straight lines!

"Well, I am curious to see what I would look like."

"Sit down and let me get to work."

So I sat and again enjoyed being the passive subject, but this time she kept tickling my face.

"Keep still or you'll look like a clown."

"But it tickles!"

"Don't be a sis… baby!"

"I guess I'd be called a sissy if anyone found out."

"I didn't mean that, Kyle."

"Don't worry. You're pretty special to do all this for me."

"That's 'cause you're pretty special. And I don't mean just 'cause you want to wear a dress. I like being your girlfriend."

"Even if I want to look like your girlfriend?"

"Even then. You're you and it suits me just fine, Kyle."

"Thanks, I'm a little nervous just now."

"Me too."

"I'd kiss you but it would ruin my makeup."

"Damn, that's my line."

"Rain check until I change back?"

"You bet. Take a look."

The makeup made a lot of difference. Looking back, I know I looked like a raccoon with the heavy eye makeup and such, but remember that for a fourteen year old girl such overdone makeup was almost mandatory - at least out of school and away from their parents.

Wow! I can almost believe that's a girl in there."

"Maybe next time we can try some nail polish."

"I'll have to let my fingernails grow some." I kept them short for working in Dad's shop. I could see that grease under the fingernails would be a problem.

"If we have time. I don't know when we can do this again."

"We'll work it out. Speaking of time, what do you want to do now you're all dressed up?"

"I hadn't thought that far ahead."

"Watch a movie?"

"Can you eat popcorn wearing makeup?"

"You'll have to learn to repair your own lipstick."

"Popcorn might taste funny with lipstick. It tastes - I don't know - strange."

"Get used to it, girlfriend. After a while you won't notice it at all."

"You pick the movie, I'll make the popcorn..

So she picked something called She's All That, where a high-school jock turns a plain girl into a beauty queen. I recognized it as an update on Pygmalion, but I also recognized why Lexie picked this one from Mom's collection.

I was pleasantly distracted while we watched because we were cuddled close on the sofa. Talk about conflicting feelings - I loved wearing the dress and being all made up, but cuddling Lexie brought up some distinctly unfeminine feelings. I know fourteen-year-olds are supposed to be confused about sex, but this isn't what people usually have in mind. When the movie finished we didn't let go of each other and let the box shut off by itself.

"So you think you could make me into a beauty queen?"

"Now that would be a challenge."

"I was right, this whole girl's clothes thing feels as good as I hoped."

"So you want to keep going?"

"If you're willing to help."

"It's fun. You seem so happy just to be wearing a dress. I like it when you're happy."

"It's a strange way to start a romance, though."

"Who cares? You better change back before your folks come home."

"I guess…"

"I'll show you how to take off the makeup, but it'll be messy. Better get a garbage bag to hide the evidence."

"You're pretty good at this secret identity thing, Lexie."

"Mom caught me trying makeup before she thought I should be wearing it when I left a whole bunch of gooey tissues in the garbage pail in the bathroom. I won't make the same mistake twice."


"Nice earrings, Dad."

"Your mother gave them to me for our anniversary."



"Do you get much grief about wearing earrings?"

"Not much. I get some funny looks but I've never had anyone tell me I'm going to Hell or anything like that. Why the sudden interest?"

"Uh, Lexie thinks I'd look cute with earrings."

Well, she said so. I just didn't tell him that I thought I'd look good with earrings, too.

"Lexie, huh? You picked a good'n with her. I don't know if you'd look cute, but she does have good taste. The question is: do you want to get your ears pierced?"

"I think I do."

"Then go ahead and do it. I have to warn you, though, it's an addiction. You won't have any money to take Lexie on a date because you're going to spend it all on earrings."

"Does that mean you've changed your mind about dating before I'm sixteen?"

"Whoa! I walked into that one. You've been seeing a lot of Lexie this summer, haven't you?"

"Sure, we're partners; she helps me with the lawn care and I help her babysitting sometimes."

"Which might explain why you aren't spending much time at the shop. I bet she's a lot more fun to work with than me or Frank."

"Aww Dad!"

"No sweat. At your age I would have preferred my girlfriend to my father any time. But to get back to the dating business, I don't suppose there's much difference between dating and hanging out with her all day, is there?"

"It's cheaper to watch a movie on the TV than to go to the theater. Besides, I can't drive yet so it would be hard to take her out."

"Which means I have another couple of years before my auto insurance rate goes through the roof. Riding your bike with her on the handlebars isn't so romantic if it's raining, though."

"It's not so romantic any time. Besides, she has her own bike. We like to ride in the park together."

"And no doubt stop along the way for a little fooling around. That's what I would have done at your age."

Dad? Fooling around? With who???

"Hey", he continued, "I was young once, it's not like you mother and I didn't fool around in the bushes a time or two."

"TMI, Dad!"

"You're fourteen, almost fifteen, Kyle. If you and Lexie aren't fooling around with each other I'd be purely surprised. Sex is nature's way of making sure we don't die out; you can't ignore it, son. It ain't healthy to try, but make damn sure you use a rubber when the time comes."

"Aww Dad!"

"I mean it. You've become a responsible young man and your mother and I are proud of you. Don't think we haven't noticed you're spending a lot of time alone with Lexie, but we trust you to behave yourselves. It's too soon for me to be a grandfather."


"Things that go without saying usually need to be said. I've said it and thus endeth the sermon on the mounting. Go get your ears pierced and you can borrow some of my earrings until you amass a collection of your own."

"Thanks, Dad."

"No problem, son."

I had to wonder what Dad would think if he knew how Lexie and I spent much of our time alone together. And no, we hadn't approached the need for rubbers.


But my bra wasn't the only one I had unsnapped.


By the end of the summer I had figured out two things; wearing girls clothes felt very good and being with Lexie felt very good in a different way. Doing both was wonderful.

Not that we spent all of our time together playing dress-up. Our 15th birthdays came and went, we were now sophisticated and worldly - or so we thought. We hung out together quite a lot, but most of the time was with our friends terrorizing the town park or - if the weather was lousy and we couldn't promote one of our parents to take us to the mall - hanging out at the teen center. That was sort of the last resort; we were borderline too cool to go there, but you had to do something!

I had my various jobs and so did Lexie, and we spent a good bit of time at the library when nothing else was going on. We soon discovered there wasn't much written material on boys who liked to wear dresses, but the fast-growing Internet was a wealth of information.

The busybodies of the town hadn't yet organized themselves to demand filters on the net in order to 'protect the innocent minds of our children' so I found out I was most likely a crossdresser and I wasn't alone. That was good to know, but it did little good to find out there was actually a group - I suppose it could be called a club - of crossdressers in town. It wasn't like I could ask my folks to take me there and the members of the club would probably would have turned green at the thought of some prude accusing them of child molesting if I did turn up at a meeting.

But the best days were those when Lexie and I had the chance to play dress-up together. By the time school was about to start I had, with Lexie's help, blown much of my summer earnings on a small wardrobe, including panties, hose, a pair of flats and my own makeup. We both still looked like raccoons - the in look for 'with it' girls, I might add - and I think I had gotten just about as good as Lexie at makeup.

My hair had grown, I had a bunch of earrings (the girly ones hidden with my girly clothes) and could put them in without staring at a mirror to find the holes. Dad was right about them being addicting.

Puberty had been kind to me, I had a pleasant tenor (according to Mom) and I didn't get all big and hairy. 5'6" seemed a good compromise, at least to me, and I was frequently described as 'thin and wiry'. I hoped my body would agree and not grow any further. At least I didn't have to worry too much about shaving yet. Funny how I had gone from wanting to have enough hair to shave to hoping I wouldn't need to shave.

Looking in the mirror to see the girl version of me was interesting, but it wasn't long before I bought one of those throw-away cameras that were so popular before everyone had a cell phone with a camera. Lexie had fun posing me in twenty-four creative ways to 'show off my assets,' but I can't say I really minded. I did make her pose for her own twenty-four exposures, and - get your mind out of the gutter - she had all her clothes on.

The problem was this was the end of the film era, and you had to take the camera to the drugstore (NOT one near you!) and wait for the film to be developed while you hoped whoever did it wouldn't realize it was you on the film.

The pictures were… interesting. I was a little disappointed, however, because it was not quite the image I hoped for. The breasts just didn't look right. (I figured out later that real breasts have weight, fiber fill is very light and the bra just doesn't fit right without weight to pull down the straps.)

You might notice that I had gone beyond my initial pleasure at how the clothes felt to wanting to look right. Lexie the fashion consultant had lots of suggestions, and I tried my hardest to listen to her. We spent a lot of time together trying to get me to look like a real girl. I don't know why she was so helpful, it's not like the normal things a boyfriend and girlfriend do together, but she was a willing partner.

As pleasant as hanging out with Lexie had become, I was chafing a bit at being stuck in the family room. I was, in the parlance I had newly learned, in the closet but I wanted out.

Yeah, right! Limited to foot or bike, there was no way I could leave the house without the entire town knowing what I was doing. It was annoying and I'm afraid I was carping a bit to Lexie.

"Jeez, Kayla, you even whine like a girl now! Maybe you should audition for the RuPaul show if you want to go out."

"Like my folks would let me go to New York or LA or wherever they film the show."

"OK, so that won't work. Too bad we can only do this during the day when your folks are at work. We could try going out at night when people can't see us as well."

"Creeping like ghosts in the dark? Some fun!"

"What, you don't like walking with me?"

"You know what I mean. And once school starts Kayla will have to go away. As grandpa likes to say, Bummer!"

"Ghosts, huh? That could be the answer, Kayla."

"Look, I may be dying to get out of the closet, but I'm not ready to actually die and become a ghost. Besides, I don't think I'd look so good in white."

"No! You know how my aunt always goes over the top for Halloween?"

"Sure, her house is always covered in spiderwebs and her yard is full of tombstones. She goes a little crazy, doesn't she?"

"But she always throws a major costume party…"

"And I could go as Kayla!" Sometimes I was quick on the uptake.

"You can get away with all kinds of outrageous crap on Halloween, and you wouldn't have to hide it from your folks."

"I don't know about that…"

"C'mon, Kayla! You love it and you know it. How long do you think you can keep them from figuring out what's going on? They have to be pretty cool if they know we're spending so much time alone together."

"You know my Dad warned me I had better use a rubber if…"

Good thing there wasn't a mirror handy - I think I might have blushed right through my makeup. When we were spending time as girlfriends we could reveal just about anything to each other, both spiritually and physically.

"You'd better… when we go that far. Besides, when we do you'd have to take off your clothes and then you wouldn't be Kayla."

"Some things are worth the sacrifice."

"Sex fiend!"


"Honey, you'd be amazed at the things I can do with a broomstick."

"So go ahead and show me."

"Looks like you've got one handy…"

Yes, we had gotten that far in our relationship. What else did you expect from a couple of fifteen-year-olds spending a lot of time alone and changing clothes in each other's presence? From this distance I can say it was fumbling, inept, scary, exciting and simply wonderful. In our saner moments we had agreed that intercourse was too much; neither one of us were interested in being parents! I still wonder how we managed to keep that resolution, those passion sessions were anything but sane, but we didn't go too far.

And that's all I'm going to tell you about it except that she wasn't bluffing.


As much as I wanted Kayla to escape the family room, I was scared to have my folks know that I wanted to wear a dress. No matter how liberal and understanding your parents are, that sort of thing is still culturally taboo. By the turn of the 21st century transgender issues were rather more open than, say, a generation before, but certainly not to the point where every time you logged onto Facebook you saw a pile of posts on the subject. While LGBT had become a well known acronym; it was still reviled by many; I had even heard my parents use the term in passing. Not a big topic of conversation in our household, but not entirely foreign.

So how did I bring the subject up? Simple - I let Lexie do it. A cute and perky fifteen-year-old girl can get away with a lot.

By this time Lexie and I were frequently guests in each other's houses, her parents were cool with us spending so much time together (I fear I was considered a good influence!) Her folks were both in sales of some kind, (at that age the details of the job were if very little interest to me) so they were gone almost as much as my parents. Her dad was a great cook and he was happy to show both of us how to put together a substantial meal, so that night Lexie and I put together something special to get my folks into a mellow mood before popping the question.

With teenage irony, that's how we referred to asking my folks to let me go to the costume party in a dress. We hatched multiple and fantastic scenarios as to how to do it, each more outlandish than the previous one, but in the end sense prevailed - Lexie just asked if she could take me to the costume party as her sister.

The answer was completely unexpected. Mom just asked me "Do you think you've had enough practice to pull it off, Kyle?"

Just what do you say to a question like that?

"I assume it was Lexie that took the pictures that you left out a while back."


"The ones of you in a dress. Actually, I was pretty happy that you both had all your clothes on."


"You'll pardon me if I took a look in your closet and found your dresses? You have pretty good taste, daughter."

It didn't take too many incidents like this one to realize there was no way in hell I could fool my mother. Most of the time I don't even try any more, her powers of observation far outstrip my pitiful efforts at concealment.

"You know?"

"Of course she knows," chimed in Dad. "The country lost a great agent when she resigned from the CIA to marry me."

"It was the only way I could think of to neutralize the threat to the nation from a rogue mechanic. He was building an atomic bomb in his basement when I discovered him."

"Nonsense! It was only a small shaped charge, suitable for entering a bank vault in the early morning."

"Too bad computers hadn't been invented back then, it's so much easier to rob a bank over the Internet. You would have made a dashing hacker."

"Darling, I think we've rather drifted from the topic of Kyle's Halloween costume."

I realize now that they were giving me time to recover from the shock. Lexie was sniggering, but my brain was still screaming 'They Caught Me!!!'.

"Well, I suppose having your ears pierced will help," Dad offered, "or was that the reason you did it?"

"Ahhh… Part of it?"

My answer was very tentative.

"Not surprising. You want to know why I got mine pierced?"

"Sure, Mr Stone," Lexie answered before I could speak. "I always wondered."

"Lots of people do. You've met Kyle's grandparents, right?"

"Sure. Those tie-dye shirts stick in your mind!"

"That's his mother's parents. My folks are not quite so flamboyant, but they tried hard to bring me up without all the macho crap their folks had in their heads. Mom and Dad were both women's libbers, I got to play with both trucks and dolls, that sort of thing. The whole idea of respect for women and gender equality just soaked into my pores.

"I was always fascinated by my Mom's long, dangly earrings. They tell me I used to grab them even before I could talk and she stopped wearing them for a while when she was carrying me around half the time because I was like to tear out her ear lobes.

"Anyway, I just loved them, and when it came time for teenage rebellion I went and got my ears pierced so I could wear long, dangly earrings just like Mom and her friends. It's damned hard to be rebellious when your parents are so annoyingly liberal, by the way."

"Tell me about it!" I responded.

"Life is tough, ain't it, kid? So, are those pictures the start of your teenage rebellion?"

"Not, uh, not really…"

"You feel comfortable in telling us about it?"

I can report, since after all this was more than a decade ago, that the phrase You have the right to remain silent! was running through my head. I really didn't understand why it felt so right to be wearing girl's clothes, but I sure knew it wasn't normal. I was silent in my confusion.

"Your folks seem like they aren't going to go ballistic, Kyle," Lexie offered. "Maybe you should tell them what you told me."

There's that old cliché about the floodgates opening, but it's a cliché because it's so true. The whole thing just sort of tumbled out when I started to talk. Mom really didn't know that I liked to stand in her closet, Dad seemed kind of proud with the way I figured out sizes and such to find my own clothes. Lexie got kind of pink when I came to the part about her helping me try on the bra in the Wal-Mart.

I did have enough sense not to talk about the other things we did while we were alone. These days I would say that talking about gender roles was safe; talking abut our nascent sex life was not going to happen!

Heartfelt Revelation is hard work. By the time I ran down I was sweating and exhausted. Lexie had a firm grip on my hand all the time as I unburdened myself, and even that was clammy.

"Hell," Dad started, "do you get the feeling that even though we thought we had this whole parenting thing down pretty well that we still haven't got a clue?"

"Grams swore by Dr. Spock," Mom replied. "and then we found out he was all wrong. Dad swore by Heinlein's method - nail 'em in a barrel and feed 'em through the bung. When they reach teenage just drive home the bung. Now I find out all those How To Be A Perfect Parent books I read while I was pregnant didn't cover things like this. Somehow I feel like I'm in the barrel and someone's shouting Look out for the falls!"

"Well, we did try not to impose gender roles on you, Kyle. I guess it worked…"

"It's not that, Dad…"

"Hey, I know. Don't sweat it, son. I spent a lot of my life trying to abandon the lousy gender stereotypes I was born into. My folks did the same and I'm not at all upset that you're carrying on the tradition. Somewhere in the old albums there's a picture of me and your mother in the matching skirts and blouses she made for a big square dance at the Falcon Ridge Festival. It was fun and dancing is pretty cool in a skirt. I just never thought about taking it any further."

"You did?" I asked.

"He sure did," Mom chimed in. "I thought it was cute but it took him a while to agree, didn't it Paul?"

"Yeah. It was fun but I didn't get the kick out of it you seem to get, Kyle. So you want to use Halloween as an excuse to try going out dressed like a girl? That should be pretty safe, I would think."

"Better than decorating the trees with toilet paper." Mom has a strange idea of humor, but then so do I.

"I'm not in trouble?"

"Of course not!" That was Dad. "Why would you be in trouble? You're still the same person no matter what clothes you're wearing. We still love you. If wearing a dress makes you happy, then so what?"

Then Mom chimes in, "What I want to know is why you would actually want to wear a bra. Most days I can't wait to take mine off!"

"A sentiment I heartily share!" Dad added.

"Paul, you're a dirty old man. You're embarrassing the children."

"They're not children any more if they're playing dress-up together."

"I suppose you're right, but you haven't let Kyle answer my question. Do you actually like wearing a bra, Kyle?"

For a second I hoped their banter would relieve me from having to answer, but no such luck. After being reassured that they weren't mad I decided to just be honest.

"Yes, I do like it. I don't know why, but it feels good."

"I guess it takes all kinds. And are you OK with this whole scene, Lexie?"

A deer-in-the-headlights look. I don't think she was expecting the question.

"I think so. It's kinda weird but I like having a boyfriend who can be a girlfriend. Kayla is not exactly a different person, but we do share things together that I might not want to talk about with Kyle."

"Kayla, huh? Not a bad name."

"It felt funny to call him Kyle when she looked like a girl."

"I'm sure! The whole situation is rather funny," answered Mom. "So OK, Kayla, knock yourself out and have a great time at the party. Can I offer you any help with makeup or accessories?"

"Would you?"

"Sure. Like most teenage girls, it looks like Kayla needs to learn how to tone down her makeup."

"Aww Mom!"

"Get used to it. Mothers are required to criticize their daughter's makeup. It's in the rules."

"How come no one told me about these rules?"

"Because my son never needed to know. This is strictly classified information; until you came over to the other side you didn't need to know."

"See," said dad, "I told you she was CIA. Hey - wait a minute! I haven't come over to the other side as you put it."

"You get exempted because of your earrings, that and you did look cute in that skirt. Maybe you and Kayla…"

"I'll leave the gender-bending to Kayla, thank you."

"Why do I feel like a spy when it was you guys that were spying on me? Looking at my private pictures…"

"Then you shouldn't have left that envelope out where your mother could see it. Any CIA operative worth her salt would never be able to resist something like that," said Dad.

"At least I only checked your closet, I didn't go pawing through your underwear drawers."

"That wasn't very thorough spying, Mom."

"Well, I thought I should wait until you were ready to talk to us. You're a pretty sensible kid."

"And wanting to wear girls clothes makes me sensible?"

"Hardly sensible, but not so unusual. Those talk shows that Kathy listens to in the office would make you think that half the men in the world are trying to find their feminine side and the other half are getting surgery. Lord knows how the race will continue if everyone becomes female."

"At least your assistant mechanic isn't addicted to Rush Limbaugh," Dad responded. Now there's a guy who needs to find his sensitive, feminine side. Which brings up a serious question, Kyle." Dad had abandoned the banter. "Is it just the clothes or is there something deeper here that we should be aware of?"

That one was easy, I had been thinking a lot about it for a while.

"It's just the clothes. I really like wearing them, but I like being a guy, too. I think I'm a crossdresser, not a transsexual."

"Well, the jargon shows you've been doing some research, not that I'd expect any less when you had a serious question. So right now all you want to do is go out as Kayla and have a good time with Lexie at her aunt's party."


"Then have you given any thought to what you'll be wearing? Your mother would be a pretty good resource. If you're going to do it, then do it right."

"I've been thinking I'd like to dress like grandma when she's in her all out hippie mode. All that embroidery…"

"See, all this must come from your side of the family, which will be a relief to my parents when they find out." Dad was grinning as he said it.

"They'll get over it - they got over you, after all."

"Certainly a challenge. Good thing I've never gotten over you. Kyle, I guess we'll have to go see your grandmother this weekend and see if she can help with your costume. You'll have to give her a call."

Talk about your mixed blessings, but I was very relieved that my folks were so understanding. Not many people were as lucky as me.


I may have been lucky, but Mom and Dad had this kind of sink or swim attitude when I got enthusiastic about something. They figured if I were interested enough, I would get off my tush and do the work needed to get it done. Once they saw I was serious, then they were willing to help.

I must admit this kept me from doing some pretty stupid things, and I've adopted the same policy for my own youngsters, but making that call was one of the more difficult tasks of my young life.

You'd think that after baring my soul to my parents with Lexie watching, calling grandma would be a cinch.

You'd be wrong.


"Hi grandma, it's Kyle"

"Well, hello honey. What's up?"

"You're going to think I'm weird but…"

"Honey, I don't think you're weird."

"Well, that's nice, grams."

"Honey, I know you're weird."

"Good! That will make things easier. I need to borrow some of your clothes."

"Run that by me again. I'm an old woman and I think my hearing's failing."

"You heard me right. My girlfriend's decided I need to go to her aunt's Halloween party dressed as her sister. If I'm going to do it I like all the embroidery and stuff you wear sometimes."

Girlfriends make convenient people to blame crossdressing on. Just ask Lexie.

"It must be the pierced ears. You poke holes in your head and all the brains leak out."

"Nah, it just lets the new ideas in. I thought you were all for gender equality."

"Well, so I am. I just didn't realize you were going to be leading the charge."

"Someone's got to do it and Lexie elected me."

"I'm going to have to meet this girl. She is a girl, isn't she?"

"Of course. You can meet her when we come over this weekend. To, uh, borrow some of your clothes?"

"Well, 'my stars and garters' as my grandmother used to say. I bet you don't know what a garter is, do you?"

"It's that thing the guy takes off the bride's leg at a wedding."

"Close. That's about the only place you find them these days. A garter is what a lady used to hold up her silk stockings before they invented pantyhose. The whole deal was annoying because the garter kept slipping and your hose ended up around your ankles six times every evening. At least you won't have to put up with that. Are you are planning to wear pantyhose?"

"I guess, if that's what you wear with a fancy skirt."

"Your great-grandmother would approve, once she got over the shock of a boy in a dress. She hated it because I was an authentic hippie. I refused to wear a girdle and never shaved my legs or wore stockings. Stockings or pantyhose hid my toenails after all the work I went to painting them."

"Geez, this is getting complicated."

"We women have our beauty secrets. If you expect to pull this off you'll have a lot to learn. This girlfriend of yours going to do your makeup?"

"She tried, but mom says we looked like the losers in a boxing match."

"I'll let you in on a secret. Your mom looked like a raccoon when she was that age and trying to seduce your dad. It's a stage most girls go through before they learn how to use makeup properly."

"I think that's why mom wants to do our makeup."

"The world is wondrous in it's ways; a boy going to a party in his grandmother's clothes and his mother's makeup with his girlfriend's help. The counter-culture lives and we will once more storm the bastions of gender equality. Why, I feel positively youthful once again, child."

"Thanks, grandma."

"Think nothing of it, child. I do have to ask a rather indelicate question."


"When I was in my hippie phase we women spurned the idea of wearing a bra as a sexist plot by the male dominators. I hardly think that will work in your case, Kyle."

"Got it covered. Lexie helped me buy a bra."

"And people thought we were radical forty years ago…"

"These days 'radical' is a term of approval."

"Well, so it is. Do your parents approve of this whole crazy scheme?"

"Well, approve may be a bit strong, maybe amused would say it better."

"I can hardly wait to see your grandfather's face when I tell him about all this. He will certainly be amused."

"It is pretty funny, but I don't want to look like a clown."

"Kyle, is there more to this than just a Halloween party?"

"Uh, maybe…"

"Then tell your old granny, child."

So I did, confession is good for the soul.


By the time the weekend rolled around I had a very unexpected problem. In fact, I was seriously considering becoming a conservative or - gasp! - a Republican.

Why, you might ask. Why, thanks for the question, I appreciate it. Let me say this about that: Instead of freaking out that their only begotten son was a crossdresser, my sensitive, liberal, free-thinking parents had become downright enthusiastic! It didn't stop there: my kindly old grandparents were ga-ga about turning me into a waiflike, hippie-freak love child in peasant blouses and swirly skirts, complete with ankle chains and high-heel sandals or some such nonsense. Conservatives seem to have all the answers with no room for questions. Having all the answers would have been nice about then.

Even Lexie was no help, she thought I was a really cute girlfriend and kept making helpful suggestions. Certainly I enjoyed crossdressing and was sure I wanted to do more of it, but I was beginning to feel like General Custer when he saw all those natives appear over the ridge.

Jeez! The next thing you know I'll be writing purple prose for some tabloid. OK, it wasn't as bad as I made it out, but it was overwhelming for my fifteen-year-old self. Lexie and I were still trying to figure out the whole sex thing and now I was trying to figure out if I was a boy or a girl or something in between. Most kids would have pretty rigid guidelines on the subject and know the answer in black-and-white. Me, I had a whole tie-dyed palette to work from and permission to paint my own picture.

Talk about overwhelming…


As I have mentioned, I wasn't old enough to drive yet, so someone had to take me over to grandma's place. Thus I found myself, dressed in my normal boy clothes, in the car with Lexie, clutching a small package with my bras and panties while Mom waved goodbye to Dad, who was looking a bit miffed at being left behind. Mom had been adamant that the afternoon was 'just for us girls.'


As I nervously rode over the river and through the woods, (how else would you get to grandma's house?) I realized that I had no idea if grandma's clothes would fit me. Really now, did you expect a fifteen-year-old boy to speculate about the size of his grandma's bust and hips? Well, actually I had speculated about the size of grandma's bust, since I nearly suffocated in it when she hugged me as a little kid. The woman was well endowed, which was confirmed when we arrived and she hugged me. I didn't suffocate because I was too tall for my face to end up in her cleavage, but with my current hyperawareness of breasts and other feminine attributes I was keenly aware of hers against me.

Can I help it if my foremost thought was I wish I had boobs like that!

Well, I suppose I should take responsibility, one of the major parental dictums in my young life was you alone are responsible for your actions. It was unspoken that I was responsible for the thoughts that preceded actions, but I didn't worry too much about that particular thought. Despite the faintly icky feeling I got when thinking of my grandma's boobs, the overwhelming joy of being able to dress like a girl had me wishing I could have my own breasts to fill my bra. Fiber-fill just didn't do the job any more.

I introduced Lexie, who got firmly hugged and kissed, before I got the grandma inspection. This is the invariable family ritual where grandma grabs you by the shoulders and informs you how much you have grown while she uses her x-ray eyes to record the minutest changes in your body since she last saw you. It doesn't matter if it's been a day or a century since the last meeting, she just has to complete the inspection before anything else can happen.

"Kyle! How much you've grown!"

See - I told you she would do it…

"You're looking good, grandma. Is gramps around?"

Can I help it if I was a bit nervous about the whole dressing up thing with him watching?

"Nope! I sent him off to drown some worms in the lake, not that he protested all that much. So you want to go to a party looking like an old woman…"

"You'll never be old, grams, and the day you dress like an old woman will never come!"

Hey - I know how to bullshit with the best of them!

"That's not what my body tells me when I get up in the morning, but thanks for the compliment, Kyle."

"It was my idea, Mrs Everett," said my guardian angel, Lexie.

"Well, if he comes out looking as cute as you do nobody will know it's a costume."

Lexie looks very cute when she blushes. It goes all the way down to her nipples, which I found out the first time I took her bra off.

"If I look as cute as Lexie then I'm all for it. She may have had the idea for us to go to the party, but I was the one who wanted to try wearing girl's clothes in the first place."

"Did he really ask you to help him find a bra, Lexie?" asked grandma.

"When I saw him standing there in the ladies' wear section looking lost I just had to find out what he was doing. The last thing I expected was him wanting to get a bra for himself."

"You aren't the only one, Lexie," chimed in Mom.

"Hey, the dress just didn't look right without boo - uh - something up top," I finished lamely.

"So, did you bring your bra, Kyle?" asked grandma. I swear she giggled.

"Sure, and my panties."

Just brazen it out, Kyle. This time I was sure she giggled.

"Then come into the spare room and we'll see if I have anything to fit you. I laid out a few things and some wrap-around skirts that might work."

"Thanks, grandma. I really appreciate this."

"Well, I have a polite granddaughter, in any case. Right in here, child."

So we all trooped in and discussed which clothes would be the best to start with. Women sure can take a long time doing stuff like that. Me, I spotted the perfect blouse right off and decided which skirt would go with it right away. Not that my opinion made much difference, but I managed to get my way.

"Uh, are you all going to watch me get dressed or do I get a little privacy?" I asked.

"Of course, dear. I guess you've had enough practice you don't need any help."

I almost told them that Lexie always helped snap my bra together, but realized that would not be greeted with very much enthusiasm. Lexie almost stayed with me before coming to the same realization.

So I closed the door and stripped, putting on my bra and panties with mixed feelings. Relief at finally being able to wear them and a bit of apprehension that I was going to have my mother and grandmother looking at me when I was done. So I stuffed the cups of my bra with fiber-fill and put on the clothes - or tried to. There was no way they were going to fit me.

Talk about disappointed! In my distress I put my t-shirt back on and went out to tell them the bad news.

"They don't fit!"

It wasn't until I opened my mouth that I realized I hadn't taken off my bra, which got me some very funny looks.

"Not to embarrass you, dear, but there's something wrong with your bustline."

"I think your breasts are too high, Kayla," was Mom's opinion.

"And they don't bounce right, either," Lexie observed.

"You're right, Lexie," Grandma agreed. "Take it from me, I've had to cope with large breasts all my life and they do bounce around."

Did I wish to be accepted as one of the girls? Be careful what you wish for, it seemed these women had no problem discussing my breasts, or lack of them, in great detail while I was standing there.

"What do you have in there, Kayla?"

While I appreciated Mom calling me Kayla, I had a hard time answering her.

"She's using fiber-fill from Joanne's," Lexie saved me from stuttering out an answer.

"You need something with a little bit of weight to it, Kayla. Any ideas, Mom?" asked my mom.

"We could try a couple of oranges…"

Which we did. Try to imagine my embarrassment while stuffing fresh fruit down my bra with mom and grandma watching. Even when I tore up the fiber-fill and re-arranged it, I had breasts that looked like baseballs at the bottom of a sack.

"No, I don't think that will work. We need something heavy but pliable…"

You might laugh at our consternation. If this happened these days you'd simply Google something like fake breasts and buy them from Amazon Prime and they'd be at your door the next day. However, Google was only a couple of years old and Amazon was selling mostly books back then. Besides, I was just starting to be computer literate and the generations before me were clueless about electronics. The thought never entered our heads.

Quite a few other thoughts did enter our heads, but were promptly banished as too impractical, too expensive or too gross.

Examples, you ask? Things like marbles, (Too lumpy) a baggie of mashed bananas or jell-o, (Food spoils and there's an ecch factor) various grains and pasta. (At least they won't spoil but they didn't have the right weight.)

Working with Dad at the shop made me think of using a big glob of engine grease from the garage. (Big-time ecch factor and I weren't sure the stuff wouldn't eat through the baggie and spoil my bra. But it did feel a lot like Lexie's breasts, not that I would ever make the comparison in her presence!)

We finally settled on a handkerchief tied around some navy beans. I think you can see why I'm so pleased with the silicone breast forms I use today!

With the filling selected and inserted, I again underwent the x-ray eye inspection. I was getting used to being a human slide under a microscope by this time.

"Your bra straps, need adjusting, Kayla."

"I can't do that. The adjusters are on my back."

"Turn around, dear, and let me help," offered Mom.

Do you have any idea what it feels like when a boy who wants to dress like a girl has his mother adjusting his bra straps? I hope you'll let it remain a mystery - you really don't want to know!

This time when I looked in the mirror my breasts were much more natural looking, even if I still looked mostly like a boy.

"Well, we'll just have to find something else she can wear." Grandma was right on target.

But none of us had any good ideas. Which was what led us to migrate to the VOA (that's the Volunteers Of America thrift shop) in town - after I had removed my bra! In her enthusiasm, mom bought me three new outfits and grandma found an embroidered blouse as well. No, I didn't try them on, but I was surreptitiously measured against the clothes so there was a pretty good chance they would fit.

After all that shopping we were hungry, so we had lunch before returning to grandma's place. There I was compelled to model the new clothes with my newly stuffed bra. I felt like I was going to drown in enthusiasm at any minute, but I fell in love with a pink dress with a white lace collar and contrasting stitching.

Then the women had to set about doing my makeup, and my nails, and messing with my hair, and making sure I had the right earrings (Grandma had a LOT of earrings!) and completing the outfit with pantyhose and sandals. It took the entire blessed afternoon to accomplish all this. I didn't realize how much time a woman needed to look good!

"Someday I'll have to have a picture of you with your cousins." Grandma was just full of ideas. "Wouldn't that be a hoot?"

"I'm not so sure about that…"

"Correct me if I'm wrong, daughter, but you're not going to stop exploring Kayla after the Halloween party, right?"

"Right!" bubbled Lexie. "I like my new girlfriend."

"Uh, she's right."

I may have sounded a bit tentative, but it was true.

"I thought so," replied Mom. "Look, if you approach this with some common sense, which may be an oxymoron for a teenage girl, I don't see why you can't be both Kyle and Kayla as you need."

"I hope it will all work out."

"And I hope we can have some dinner soon. This brainstorming is hungry work!"

Grandma is always so practical.

"Mom. Do you have an extra purse for Kayla to use?"

"Sure, I have a bunch in the closet. Take your pick, dear."


"A young women never leaves the house without her purse."

"Leaves the house?"

"Of course! How else can I take you to dinner?"

All I'll say about dinner was I discovered breasts catch catsup dripping from a hot dog all too easily. That and having your mother wipe it off your boobs is very, very weird!

I made it through my first meal out as Kayla with only some minor bits of panic, and no, I deliberately didn't drink much so I didn't have to face the Ladies' Room bit that everyone puts into these stories. That came later.

I know Lilith Langtree hadn't written the story yet, but she must have borrowed the title to Either Do It Right, or Don't Do It At All from somebody like my folks. They were determined that I would not make a fool out of myself at the party.

Have you ever had deportment lessons? I mean like Miss Jane's Guide to Proper Behaviour for Young Women Of Superior Breeding. I deliberately spelled behavior with a 'u' because Mom turned into a hoity-toity British taskmistress to teach me all the little things I never learned growing up as a boy.

Boy are there a lot of them! I am now certain that she had been secretly yearning for a daughter. (The doctors warned her that another pregnancy might kill her, after my birth almost did the deed.) The problem was she had only about three weeks until the party to accomplish what takes most girls fifteen years.

Remember, I still had to live my normal life as a boy, going to school and doing homework and taking care of the side jobs I had promised to do. Good thing October is a slack month, lawns have mostly stopped growing and the snow has yet to fall and require shoveling. On the other hand, my cash reserves were pretty low. On the third hand, (neat trick, huh?) my folks pitched in to buy me some nice clothes to wear as Kayla. Who would have thunk it?

So I spent a several evenings a week being Kayla, helping Mom and Dad cook and clean (not that I didn't do that as Kyle, but doing it as Kayla was a bit more interesting) and indulging in conversation, trying to adopt a feminine voice and perspective. Not as easy as it sounds.

Sundays were spent with Grandma and Grandpa, out and about at a safe distance from home so no one would recognize me. Lexie came too, but I had to remember that we were girlfriends, so no PDAs were allowed. That part was both weird and hard, but we did it.

Now we come to the bathroom scene. My poor head just about spun off entering the ladies' room with my mother, my grandmother and my girlfriend. We all went to individual stalls and took care of business, but I did find out that ladies made just as many noises as men in the same situation. You just don't want to know that about your mother. Or Grandmother. Especially not about your girlfriend!

Lexie and I did the 'repair our makeup thing' while Mom and Grandma watched tolerantly. Neither one was wearing any makeup; their attitude to wearing makeup scandalized my youthful, girlish soul. It wasn't until much later that I came to consider makeup as a necessary evil when becoming Kayla.


And so we come to the Halloween party. At least when you're telling the story you can skip over the boring parts.

Yeah, right - my wife is reading over my shoulder and has another opinion. Since she is reading as I write and impeding my creativity, I shall not offer my opinion of her opinion. So there, Lexie.

That lets the proverbial cat out of the bag, doesn't it? You can take it as given that we fell in love and got married, since I already told you she was my wife. Too bad we weren't so clear headed and used to each other's idiosyncrasies when we were starting out, not that I'd want to change anything.

I suppose it was inevitable; just as I was feeling comfortable as Kayla someone recognized Lexie and came over to say hello. Not a real problem as they didn't know me or my family, but when they told Lexie's folks they had met her wandering around with a girlfriend when she was supposedly with her boyfriend and his family, they were more than a little curious. So she had to explain she was me and I was a he and we were all together. Wait… I think I may have just misquoted a line from the Beatles from back when Grandma was my age.

They weren't too mad, just mostly curious. They knew that Lexie had (as far as they were concerned) dragooned me into being Kayla for the party, they just didn't realize the extent of my wanting to be Kayla outside the party. Not that we had emphasized my feminine desires, mind you, just sort of played them down. So Lexie came clean, and her folks decided it was time to meet Kayla and her family.

See why I wanted to skip over this part? See why Lexie didn't? She still thinks it was highly amusing to bring home her boyfriend in drag, with his parents in tow. I love you anyway, Lexie.

The logistics of dinner were a bit complicated, as I was still trying not to let the entire world see me as Kayla. Alright, I was going to go public at the party, but Halloween excuses a lot of stuff. I just didn't want the word to get around school that I was a drag queen or something. Attitudes toward gays were starting to change back then (and no one made any never-mind about the difference between being gay and being a crossdresser) but the run-of-the-mill troglodyte was feeling hurt and confused by having their cherished notions of what it was to be male challenged. A scared and confused troglodyte tends to pound on people that scare him.

Me, for instance. I couldn't go to the party if I was in traction.

However, I was as cocky as a fifteen-year-old boy can get, despite outward appearances. I was comfortable, if not totally convincing, as Kayla and thought I could handle it. I did consult Mom about my outfit for the dinner with Lexie's family, and we settled on a simple, full brown skirt and orange blouse. Kayla, the human pumpkin, decked in seasonal colors. My bean bags, by now carefully hand-sewn together, were comfortable in my plain, white bra that just showed through the fabric of the blouse. Such a wholesome girl!

I hoped.

I haven't mentioned it before, since this is Kayla's story, but as Kyle I was over at Lexie's place quite a lot. Sharing dinner with her folks was pretty much standard once or twice a week, just like Lexie came over to our house. They hadn't met Kayla and, frankly, I never expected them to meet her except at the party. The whole idea of dressing like a girl just gradually grew; I hadn't put any thought into what would happen the inevitable happened. I didn't realize it was inevitable until it did happen.

Once again, I need a cliché here - nervous as a cat by a rocking chair about covers it. Hey - they're clichés because they make a situation clear without the need for a paragraph full of words. Anyway, Kayla arrived at Lexie's door, with parents in tow, in full daylight, just like it was a normal thing to do. I must have been broadcasting panic pheromones in great profusion, but at least my stocking-clad knees weren't shaking. I was glad I was wearing flats, because I would have fallen off high heels. I was embarrassed enough without doing a face-plant in the doorway.

I swear I was greeted with a hug and a 'How nice to meet you' from Lexie's mom and her dad took my hand and said "You look lovely, Kayla."

"Thanks, Mr McFee."

"I wasn't quite sure what to expect, but…"

"I know, nobody really knows what to say about me in a dress."

"Well, it certainly is a conversation stopper."

"Does that mean I can stop talking?"

"Until after supper, then we start the grilling."

"You'd better talk to mom first. She learned a lot of good stuff in the CIA."

"You were in the CIA, Kathleen?"

"See, Paul? Your big mouth has gotten me in trouble again. I'll leave it to you to explain."

In the ensuing confusion, Lexie and I made our escape. It was inevitable that the old folks were going to hash out whole situation. Better we should be somewhere else while we were dissected.


We indulged in a quick but careful snog - when you're both wearing makeup you have to be careful! - and then looked at each other and began to giggle. I don't know how that happens, but when I was Kayla I really could giggle like a girl. Strange!

Dinner was unremarkable, much to my surprise. There was pretty much the normal type of conversation; mostly among the adults but they did make an effort to include us. The only strain was being careful not to drop any food on my boobs, I just didn't want to have to wipe something off them with Lexie's parents watching!

The grilling afterwards was more like a light roasting, evenly browning the both of us as to what we were up to and where we were going. We covered what has now become my Crossdressing 101 lecture - Yes, I want to be a man most of the time. Yes I do respect women. Yes, I'm wearing women's underwear and all the accoutrements. No, I don't want to have surgery. Yes, I enjoy the clothes. Yes, Lexie approves but you should ask her. Yes, I do use the ladies room when necessary and get out after I'm done. Ask my mom, she can tell you.

That bit about Mom usually lays that subject to rest. At least it did until the recent nonsense with HR2 in North Carolina, but this story is set safely in the past when we didn't have to deal with idiocy like that.

Then came the expressions of faith that Lexie and I were sensible enough to be trusted alone together and the assurances on our part that we were well aware of how babies were made and would not do anything to make them grandparents too soon. The methodology of this assurance was carefully not discussed, much to the relief of all parties to the discussion, especially as Lexie and I had been exploring all the ways to have sex short of intercourse. The evening ended with cordial good-byes and a great sense of relief on my part.

Then Lexie's father dropped the bomb.

"So, Kayla. You've shown us that you can be convincing as a girl, but that hardly seems to be suitable for a Halloween costume. What are you planning to wear?"

Planning to wear? Hell, I was just going to go as a girl - what more was needed? I was far too new at feminine dressing to realize that you had to put thought and planning into an outfit. Especially the outfit you wore to make your debut in the world as a girl.

All right, I was naive, no doubt about it, but I found I didn't have to answer. More accurately, I couldn't get a word in edgewise as the others in the room offered their opinions.

"A ballerina?"

"Mom!" replied Lexie, "It has to be something where she can wear a bra. No, uh, natural attributes, if you know what I mean."

Which of course led to a discussion of what was actually my bra and then the whole story of how we arrived at that solution had to be repeated. I thought Dad was just about to bust a gut laughing. Eventually they returned to the subject of what I would be wearing and the babble began anew.

"She could be a nurse."

"Nah, not Nurse Ratchet."

I had to look that one up - yucch!

How about a maid?"

"Too demeaning."

"And too sexy!"

I had to agree!

"A nun?"

"Where would we find a habit? They don't wear them anymore."

"A plumber?"

"Nah. Plumbers don't wear dresses at work."

"Besides, how could she show a butt crack in a dress?"

"If it was a really short dress…"

"A secretary?"

"No - we need something that has distinctive clothing."

"A bride!"

"Yes! A bride!"


"Wait a minute!" I cried. "Bridal gowns are expensive and I can't afford that much for a Halloween party!"

Dad just smiled. "Of course, the parents of the bride traditionally finance the wedding. Don't worry about it, Kayla. We have it covered."

"I've only been your part-time daughter a couple of weeks and now you're trying to marry me off?" I asked.

"You'd make a lovely bride, darling. There are lots of gowns in the thrift stores, we should be able to find something." Mom replied.

"In that case, will you marry me, Lexie?"

"I'm too young. You'd have to get my parent's permission, silly. Talk to them."

"How about it, Mrs McFee? You could be mother of the bride and a bridesmaid for me. You'll never get a better offer."

"I'd get dizzy trying to figure out which side of the aisle I was supposed to be on. Not that this whole conversation hasn't made me dizzy."

"Hey, Mom!" Lexie cried. "I still have my bridesmaid's dress from cousin June's wedding. I could wear that and you can make Donald wear a tux and play the groom!"

Donald is Lexie's big brother and Lexie was just full of ideas.

"I'm not about to marry someone who hasn't even taken me out on a date!"

"Donald doesn't date younger women."

"Thank heavens for that!" I replied fervently. "I don't want to marry him, I'll take Lexie."

"You say the sweetest things, Kayla!"

Then she gave me a big kiss, right there in front of everybody.

"Larissa? Did I just see our daughter kiss another woman?"

"Well, Kayla sure looks like another woman and she certainly did kiss her. Have you two been practicing?"

"Yup!" grinned Lexie. "Want to show them, Kayla?

So this time I kissed her.

"Maybe we'd better marry them off, and right quick!" Lexie's dad opined.

"I've heard of two bride ceremonies, I just never thought I'd see one. My little girl!" Mom crooned.

Mom had definitely lost her mind! Little did I know the strength of a mother's urge to dress her daughter in a wedding gown. Multiply that by two mothers and a grinning girlfriend and no mere male could resist the force, no matter what clothes he had on at the moment. My fate had been decided - I would be a bride at fifteen.


There's a school of art called Surrealism, which the dictionary defines as "a 20th-century avant-garde movement in art and literature that sought to release the creative potential of the unconscious mind, for example by the irrational juxtaposition of images." It's not going too far to say that my life had become completely surreal, the images that remain juxtaposed in my mind are truly irrational!

Take the whole shopping thing. We spent three whole evenings going to thrift stores looking for an affordable wedding gown that fit me. That meant my mother actually wanted me to dress up as Kayla to go out with her. Do you know how weird it was to go from hiding my passion for dresses to being practically required to wear a dress? In public?

Don't get me wrong, I loved it. With typical teenage enthusiasm I had embraced crossdressing with a passion. I would have happily worn a bra 24/7 if I hadn't known it would get me into deep trouble in places like gym class. For that matter, I did wear my panties on days when I didn't have gym. And yes, you can use a urinal quite handily while wearing panties and no one notices.

Despite all that I was really a fifteen-year-old boy. I liked doing typical boy things, like working on cars and mowing lawns, and I wasn't interested in giving that kind of thing up. But I liked wearing dresses and my mother and my girlfriend's mother and my girlfriend were all OK with that.

More than OK, they were enthusiastic!

I was confused, but I loved it, too.

Mom was right, there were quite a few bridal gowns in the thrift stores, but it wasn't so simple to find the right one. 'Thin and wiry' isn't a body type common for brides, so that limited the selection. It was on these expeditions I learned that an awful lot of brides wanted to display 90% of their boobage to the world as they walked down the aisle. Since I didn't have any boobs beyond a couple of bean bags we had to look for something with a high neckline. Hmmm. The phrase grow a set might be used here in an entirely different context from what I usually heard. I have to admit I wondered what it would be like to have real breasts, but not enough to actually find out!

So far, my trips in public as Kayla had been a comfortable distance from home near Grandma's place, I wasn't too worried that I'd find someone I knew who would spread the gossip far and wide. However, there weren't so many thrift stores over the river and through the woods, they were concentrated much closer to home.

The first night was a bust, but I did try on five different bridal gowns, none of which pleased the assembled fashionistas or me. I missed having Lexie help me dress, but no matter how enthusiastic our mothers were about finding me a dress, that enthusiasm would not extend to mutual undressing.

Mom did find a bridal gown for herself that first night. That's right, she and Dad had been invited to the party and she was going as the bride of Frankenstein. She was not constrained by the need to hide non-existent boobs, so she had a much easier time of it. The dress didn't have such an easy time - before she was done with it the poor thing was very artistically distressed.

Dad had an easier time, all he needed was an old suit, about a gallon of green face paint and a couple of bolts; those easily produced by a mechanic. Mom must have used about a gallon and a half of green to cover her exposed boobage. She was pretty good looking for and old broad, but I still have a faintly icky feeling talking about my mother's cleavage, even to this day.

See, I've distracted myself again. Now back to Kayla's story…

I suppose you can get used to anything if you do it often enough. By the second night I was dressed and waiting when Mom got home and we met Lexie and her mom for dinner at the China Buffet before hitting the Goodwill next door. No luck there, but there were three thrift stores in the adjoining strip mall. No luck again, but Mom saw me looking at a maroon formal gown with longing eyes. She just smiled and handed it to me.

"Go ahead, try it on, Kayla."

"Are you sure?"

"Why the heck not? You don't intend to stop dressing up after the party, do you?"

"Nope. Thanks, Mom!"

It fit perfectly.
The third night was the charm, proving once again that you will always find what you're looking for in the last place you look. Duh! We went to the High Fashion Goodwill in one of the trendier suburbs on the third night and there it was: a confection of white fluff, bare arms, a neckline that actually touched my neck and the sweetest red belt to hold it all together.

I adjourned to the changing room and put it on, but had to ask Mom to help zip the zipper in the back. Who says you don't need a ladies maid in these modern times? The fashionistas rendered their opinion: perfect but you need some hips, Kayla.

I have a perfectly good set of hips that have served me quite well for fifteen years, but looking in the mirror I could see what they meant. My hips zigged where Lexie's zagged. This led to a sotto voice discussion of what to do about it.

Remember a while back when I mentioned Grandma's girdle? I had to look up what she was talking about - I had never heard of a girdle before and was too embarrassed to ask Grandma to tell me what it was. I tried to look it up on the school's computer, but I got blocked. Did that mean a girdle was something to do with sex? I kind of doubted that Grandma would be telling me about sex toys.

Throwing caution to the winds, I asked Dad what a girdle was. He just started to laugh and told me to look in the Sears Catalog. I was beginning to despair of ever finding out when he told me what the Sears Catalog was and why every boy of his generation wanted to look at it.

"It's was the easiest place to see women half-nekkid, Kyle. It was a rite-of-passage for most boys, maybe that's why you decided you liked wearing girl's clothes - you just didn't get to see enough women in their underwear as you grew up. There was page after page of women in bras and girdles and even corsets.

"So what was a girdle?"

"A torture device made of elastic that squeezed a woman's body into the shape that fashion decreed all women must have, even if they didn't start out with a body that conformed with fashion. Especially if the woman had a few more pounds than fashion dictated. Up until the sixties a woman was considered to be the next best thing to a prostitute if any part of her body from neck to hips moved in the way nature intended. Just be glad nosecone bras aren't still in fashion!"

"What kind of bra?"

"Would you believe for a little while the fashionable woman squeezed her breasts into a point like the nosecone of a rocket? Seriously! I kid you not!"

"That's sick!"

"And eight inch stiletto heels aren't? Fashion is its own master and not accountable to anything faintly related to reality. Just remember that if you keep up with the crossdressing."

See - I got distracted again with telling you about girdles. Anyway, I pretty easily figured out if bags full of beans could stand in for breasts, then a girdle full of something (I wasn't sure just what!) could give me some more feminine hips. I had no idea how complicated this was going to get when I got up the nerve to buy that first dress!

Dad implied that girdles went out with the sixties - a good forty years ago. Given Grandma's opinion of them, there certainly wouldn't be one in a box in her attic, and Mom heartily agreed with her mother on the subject. I certainly hadn't seen anything resembling one in the thrift stores. Where was I going to find one?

That's where my fashionistas came to the rescue. It appears JC Penney is retro enough to actually stock girdles in their bigger stores. Not many, certainly not sexy enough for a bride on her wedding day, but they were plain white and looked just as bad as Dad had told me.

I had to try it on. Do you know how embarrassing it is to put on an obsolete piece of shapewear with your mother, girlfriend and girlfriend's mother waiting to see if it fit?

It fit snugly around my tummy and loosely below my waist, pretty much like I was told it should. No, I did not leave the dressing room to have the fit evaluated, there are some things a girl just won't do!

Fat lot of good it did me - I had to have Mom help tailor the stuffing so she got to see me in just my panties and bra after all. She tried to be cool about it and almost succeeded. When everything was finished she gave me a kiss on the forehead and we both broke down in giggles that lasted for a very long time.
So, Lexie my dear, I have complied with your wishes to tell the whole story. See why I was reluctant to put this part down? Now, can we get back to the Halloween Party?


Well, the Halloween party was a bit of an anticlimax. After weeks of being Kayla just as soon as I got home from school until bedtime I was almost blasé about the whole thing. Amazing how the fantastic becomes normal so quickly, isn't it?

Dad was so taken by his daughter the bride he made me sit for a photo session before the party. He blew a whole roll of film; remember, this was back when digital photography was still new and expensive. My favorite is still the one of me in the tree in the back yard, with my pink bouquet and one pink flower in my hair. The dappled light through the leaves of the tree really makes the shot pop. You'll notice that Mom did my makeup, very understated and appropriate. I wasn't anywhere near that good with makeup after only a couple of months of trying. Thanks, Mom!

Mom and Dad got all the attention; her in her green skin and acres of cleavage, him with his rusty bolts. Me - I was a young lady in a fancy dress, nothing so remarkable for a Halloween party. Actually, that suited me fine; I was happy to be taken for a young lady and had a good time flirting with her cousins who didn't have a clue. The Devil made me do it - at least that's what I claim when Kayla does something outrageous. Old Nick is a great one to blame, he has very wide shoulders.

Lexie was smashing as my bridesmaid, but she looked even better a few years later as my bride. No, it was a single bride ceremony and she was it. Not that we didn't toss the idea around, but I wore a monkey suit and just dreamed of being the bride. I wasn't going to hog the limelight from my love at our wedding.

We did wear matching bras and undies under the fancy clothes, however.


So, that's how it all began - from running under the clothes racks to occasional weekends as a lesbian couple when we can get the grands to take the kids. We do speculate what will happen when our son reaches fifteen, but as he's just started kindergarten that's comfortably in the future. You'll have to wait a decade or so if you want to know the answer.

Once again, thanks to Alys for her help with this story!

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