Kyle has purged and is trying to be "normal" - only to find it impossible. After two years of misery, his sister Christine dares him to put on their sister Taryn's dress. Can he resist? What happens to Kyle - and what does his mischievous sister have in store for him?

BUDDING LILLI

Chapter 1 — Sunday, May 16, 2010

“It’ll be okay. You’ll see.” My younger sister Christine gave me a big hug.

I stared at the landscape paintings on the cream-colored walls, wishing I could disappear into one of them, as we waited for our older sister Taryn to bring our mother downstairs to the basement.

“Of course it will!” My girlfriend, Mira, reassured me by squeezing my hand and gently touching my cheek.

The cushy, overstuffed couch we were sitting on was one of my favorite places in the house to relax. I had spent many hours lost in thought while ensconced in the embrace of the soft, burgundy upholstery.

Now, I was facing my own, personal hour of judgment. Nothing could ease the dread in my soul.

I looked down at my black skirt and tights, along with the black, leather ballet flats I was wearing. The black top and bold teal cardigan rounded out my outfit nicely. I couldn’t help smiling at the way those clothes made me feel so much like a girl - no easy feat for someone born biologically male.

Yet, I could feel the apprehension that tainted my smile, knowing that my mother had no idea I was dressed that way or why — and she was about to come down the stairs.

Uncomfortable with the thought of the imminent confrontation, my mind wandered as it searched for a safe harbor, my thoughts drifting to the experiences that had led up to this decisive moment in my life.

Chapter 2 — Friday, May 14, 2010

“How about this one?” Christine smirked.

She held up a denim skirt with beautiful embroidery on the back pockets, her coyly raised eyebrows silently suggesting that Taryn add it to the Goodwill bag.

“No!! Put that back! That’s my favorite!” Taryn gasped.

“I know. I’m just messing with you,” Christine smiled with playful menace.

I witnessed the exchange between my sisters with a giggle as they cleaned out Taryn’s closet. All three of us got along well but Christine was irrepressible. The little imp had a good sense of mischief and knew just what to do with it. Malice never had any role in her actions; her only objective was to get a good reaction. Still, it was best to be on guard with her around.

I looked around Taryn’s room, drinking in its femininity. The lilac walls gave it a nice ambiance, while the white, embroidered comforter lent the right amount of femininity without overdoing it.

My thoughts drowned out my reality as I wondered, not for the first time, why I felt so much more comfortable in her room than I did in my own.

Taryn laughed out loud, snapping my focus back to the cleaning out of her closet.

“Christine, give it a rest!” Taryn giggled covering her mouth with one hand.

“Oh, come on! You don’t think he would look cute in this dress?” Christine stared at her sister bug-eyed as she pushed back.

Oh shit! I hope they’re not talking about-

“I didn’t say that, sis! I just really don’t think he’d care to-”

“Hey Kyle!” Christine cheerfully spun around to face me, holding up the pretty lavender dress. “I dare you to put this on! In fact,” she smiled wickedly, “I dare you to completely dress up as a girl - again!”

“W-what?” I sputtered.

“Oh, Christine, don’t embarrass Kyle!” Taryn couldn’t help laughing. She held her sides as though they’d rupture.

“I’m not putting that on!” I balked as I felt my face burn.

Christine began to use her persuasive, irresistible, puppy stare — the one that always worked on me.

“Awwww, come on! If we were playing Truth or Dare, you’d do it! You’ve never been afraid of a dare before. Come on. Pleeeeeeease?”

“You know that’s true, Kyle,” Taryn chipped in. “You’re not usually afraid of a dare.”

Oh, Christ! Now Christine’s got Taryn on her side!

“Kyle, I double dare you to dress as a girl!” Christine upped the ante, making the dress dance as she held it up to taunt me.

I paused as I stared at her.

“No! No way!”

Christine stared right back at me.

“Boys aren’t supposed to refuse a dare, right Taryn? Isn’t that like one of the boys’ unwritten rules for being a man?” She made the word ‘man’ drip with sarcasm as she rolled her eyes. “Well, maybe you’re just not supposed to feel fear, but it’s the same thing. Come on, Kyle! Grow a pair!” She thrust the dress at me.

“A pair of what? Boobs?” I answered, glowering at her with my arms crossed.

“You know, she’s right Kyle. Guys are really not supposed to turn down a dare,” Taryn laughed. “And she double dared you.”

“Shut up! You just want to see me dress up as a girl!” I huffed.

“Now that you mention it, yes I do,” she admitted. “So get on with it!”

Christine laughed as Taryn grabbed the dress from her and took a step toward me, holding out the dress in a manner that suggested she fully expected me to take it. I looked at her, my arms still firmly crossed, as though she were offering me a platter of steaming manure.

My sisters were ganging up on me - and Christine was one persistent little bugger when she really wanted something.

“Come on, Kyle!” She closed in on me. “Do it! We won’t tell anyone.”

She made a “zip-the-lip” gesture, twisting her hand as though locking her mouth shut.

“You have got to be shitting me!”

Christine rolled her eyes.

“Come on, Kyle, didn’t you grow your hair to your shoulders so you’d look like a girl when you dressed up?” She ran a finger through my hair before letting out a giggle.

I turned red as a stop sign as if Christine had thrown a switch.

“N-no!! That’s not why I grew my hair this long!”

Christine!! You’re not supposed to tell anyone, you little-

Taryn gasped, putting one hand briefly over her mouth before she spoke.

“Kyle, is that true?”

My eyes bugged out of my head at my sisters.

“No!!” I lied.

“Then you won’t mind dressing up for us!” Christine giggled at me as she folded her arms.

“Shut up, Christine!” I snapped.

“Only a coward refuses a double dare! You’re not a coward, are you?” She stuck her face right in mine.

Christine had pushed my last button. Suddenly, I put my fists on my hips and playfully glared at Christine. Then I rolled my eyes as I held out one hand toward Taryn.

“Give me the fucking dress.”

The girls guffawed at me, but Taryn tried to be nice.

“I am impressed, Kyle! Good man!”

“Not in a dress!” I stared at her.

We all erupted in laughter as I turned to head for the bathroom.

“Kyle, wait! The dare was to dress up completely!” Christine flashed a classic Cheshire grin.

I stopped and looked at Christine with annoyance.

“Thanks for reminding us, Christine,” I replied snarkily. “Fine. Bring it on.”

Christine giggled as she helped Taryn put the rest of my outfit on Taryn’s bed. I watched them pick out a white satin bra, matching panties, a white slip, a pair of white, leather flats, and a pair of white pantyhose.

“Oh, my God,” I groaned. I shook my head in resignation and sighed. “All right, fine, give me the stuff.”

I held out my free hand to receive the rest of the outfit, my sisters hastily filling it before I could change my mind. We giggled together as I headed to the bathroom in the hall to accept my fate.

Chapter 3 — Sunday, May 16, 2010

I gripped Mira’s hand as I waited for my mother to come downstairs. The uncertainty of not knowing how she would soon react was torture. I hoped that she would take it alright, but I had no idea what to think. I could only wait and find out what happened.

Mira shifted her position as she put one arm around me and resumed holding my hand with her other one.

“This will be over pretty soon and you’ll find that it’s all working out okay,” Mira smiled, trying valiantly to persuade me that I had nothing to worry about.

Each second seemed to last a week as I sat in the overstuffed couch huddled with Mira and Christine, awaiting my fate. My mind departed again in a desperate bout of escapism, gravitating back to what had led to the tense wait, picking up where it had left off.

Chapter 4 — Friday, May 14, 2010

I stepped into the powder blue bathroom, hanging the lavender dress on the back of the door. The white, tile counter next to the sink was large enough to accommodate everything but the shoes, which belonged on the floor anyway.

I removed my clothing and stepped into Taryn’s lingerie. A smile appeared on my face as I slipped on the white nylons. Once I had them on, I paused. I was sixteen and slow to mature; my limbs were still bare of hair. The feeling of the nylon on my bare legs was out of the masculine world. I felt very feminine - and I found myself enjoying that sensation, just as I always had.

Suddenly, I stopped what I was doing to stare at myself in the mirror.

What in the fuck am I doing? I gave this up two years ago! I made it two years without dressing as a girl! I was going to be normal! I made so much progress and I’m throwing it all away! Why am I doing this?

That was a question I could not yet answer. I looked at my reflection, staring into my own eyes, trying to find the answer somewhere within them.

The phone startled me as it rang, bringing me out of my reverie.

“I’ll get it!” Christine chirped.

I let out a long sigh.

Why did Christine tell Taryn that I grew my hair long to look like a girl? I stopped dressing as a girl two years ago - well, until now.

I ruefully looked at myself in the mirror as I considered pulling the plug on this dare of Christine’s . . . but part of me wanted to be dressed as a girl again, the part of me that had done it — and loved it - so many times before.

Chapter 5 — May 2008

“Hey, Christine! Can we dress up Kyle as a girl again?” Sara asked excitedly.

“Yeah, that is so much fun!” Jill agreed.

I couldn’t help overhearing from where I was sitting — in the overstuffed couch six feet away from the table where Christine and her friends sat, waiting for their freshly done nails to dry.

I was watching a rerun of CSI: New York. I wouldn’t admit it to myself at the time, but I loved the cute tops that the character Stella was always wearing.

“Oh, I bet we can arrange that!” Christine smirked.

“Cool! He really does look pretty as a girl!” Sara smiled as she blew on her nails.

I peered over my shoulder at the girls as they giggled at me, throwing glances my way, anticipating my answer to their request.

Christine stood up and the three twelve-year-old girls approached me from behind, all of them smiling at me eagerly.

This kind of attention from girls does not suck — even if they are two years younger!

“So, Kyle. You obviously overheard. So how about it? I’ve got just the dress!” Christine began.

“Dammit.” I sighed dramatically. “Well, we all know that you’re going to bug me until I do this, so let’s just get it over with.”

I turned off the television, using the remote as I rose, the girls cheering at my decision.

They brought me to Christine’s pastel yellow room, where they wasted no time getting started. A few minutes later, I was wearing a knee-length, sleeveless, pink dress with a white floral pattern on it. My outfit was completed with white sandals over a pair of white anklets.

Normally, the girls put all of this over my normal underwear, but this time, Christine declared that I should wear female underwear. Seconds later, she held up a white pair of panties and a matching bra. Sara laughed hysterically. Jill’s reaction was more subdued but she thought it was funny, too.

I pretended to refuse to wear them, but Christine was persistent as ever, and I gave in. I soon found that wearing the bra and panties under the rest of it made me feel like a real girl.

My hair was already down to just past my chin. Naturally, the girls used this to their advantage. They brushed it straight, giving it an inward bob along the bottom with a hair curler.

“Aw, Kyle you look so cute as a girl! Are you sure you’re not one? You definitely should have been!” Christine gibed, setting off a round of giggling.

I chortled along with everyone else, but Christine’s little joke troubled me.

Before I could figure out what was bothering me, Christine's cell phone rang, wafting through the laughter, and Christine went to answer it. I spent a minute or two posing for the girls as Christine chatted with another of her friends.

“Um, girls? Well, not Kyle, just girls, I mean,” Christine joked as her friends laughed at her.

I chuckled half-heartedly as well, but my sister’s remark had left me feeling excluded. I thought that was strange, but I dismissed it.

“It’s Jen on the phone and she can’t make it after all. She wants to have some quick girl talk on speakerphone, so Kyle, please get comfortable in here while we take this call in the basement. I doubt we’ll be that long. Oh, and no changing back, okay?” Christine playfully warned me.

“Okay. I’ll stay a girl,” I smiled at them.

The girls left the room, taking the ambiance with them. Having the room to myself, I walked over to Christine’s full-length mirror. I smiled at my reflection, daydreaming that the girl in the reflection was all-girl, mentally and physically. My thoughts drifted to imagining that I was that girl.

A good look at the girl in the mirror revealed that something didn’t look right. Soon, I realized what it was: I had always felt that tights or pantyhose looked much nicer with a dress than ankle socks.

I had always wished that the girls would dress me in a pair of hose. They looked so beautiful on a girl and I had always wanted to try them. When the girls convinced me to wear the lingerie beneath the dress I thought sure they would add a pair of hose, but they had selected the ankle socks.

Bleah!! Ankle socks look better on little girls! I’m sixteen! If I’m going to wear a dress, I should be wearing pantyhose, not ankle socks!

I sighed as I glanced at the clock on Christine’s nightstand, wondering how long the girls would be. I figured that I had enough time to slip on a pair of hose for a minute and put them back — just long enough to see what it was like.

What the hell.

I walked over to Christine’s closet, looked at her shoes and picked out her white, leather flats with a one-inch heel. I put them on the floor next to the dresser, where I slid open the top drawer. That one seemed to be for lingerie. I slid open the next one to find Christine’s socks, leggings, tights and pantyhose.

I picked out a pair of semi-sheer white pantyhose, absent-mindedly closing the drawer. Eagerly anticipating the feel of the nylons, I removed my sandals and socks. I carefully slipped the hose on just as I had seen a woman do on TV a few times, thanking my lucky stars I had no hair on my legs.

I pulled my dress back down and stepped in front of the mirror again, marveling at the difference. The pantyhose looked and felt wonderful.

That is so much better!

I loved seeing my fully feminized reflection in the mirror, but I wanted to walk around a bit to feel the hose on my legs. Without thinking, I put the sandals back in Christine’s closet and put her ankle socks in her bathroom hamper as an excuse to walk around, enjoying the sensations along the way.

The nylons made me feel like a girl in a visceral way. That feeling was exhilarating, like nothing I had experienced before. I admired myself as long as I dared to - soon absorbed enough to lose all track of time.

Well, I’d better take these tights off before – oh shit!!

The girls’ voice echoed down the hall as they headed for Christine’s room. I frantically looked around for the ankle socks and shoes, but . . .

Shit!! I put the other stuff away!!

I started for the bathroom, but I only made it two steps before the girls walked into the room, took one look at me, stopped in their tracks and dropped their jaws.

Jill stared at me so intently that she didn’t notice the other two girls stopping right in front of her — until she bumped right into Sara.

“Sorry!”

“That’s okay.”

Neither girl took her eyes off of me.

The room was glaringly quiet for a few moments. It was Christine who broke the silence with an uncharacteristically serious tone.

“Kyle, you, um . . . y-you touched up your look.”

I nodded, too afraid to speak.

“Kyle, do you . . . do you like being dressed as a girl?” Christine asked me as I looked down, studying my feet in the leather flats and hose. “I mean, I know you never exactly resisted being dressed up, but we thought that you were only doing it because we were making you do it — that and maybe because it got you attention from girls,” she giggled nervously.

I sat on Christine’s bed, carefully tending to my dress, before closing my eyes and taking a breath.

“I do like dressing as a girl. I hope you don’t think I’m weird or anything. It’s not like that. It’s just . . . it just . . . feels nice,” I murmured as I looked at my feet again.

Nobody spoke for a few moments.

“Okay . . . can you tell us more about why you like to dress as a girl?”

Christine sat down next to me and the other girls took it as their cue to sit as well. I looked at her while I tried to understand my own feelings.

“Well, it’s kind of hard to explain, Christine. I know that I like dressing as a girl and I know that I think of myself as a girl when I do.”

“Wow. What do you think it means?” Christine prompted.

“I’m not sure. What I do know is that when you dress me up I always really want to. I mean . . . it’s almost like I need to for some reason. It’s like . . . well, it’s like walking around barefoot when it’s below freezing outside, and dressing as a girl gives me relief like putting thick socks and boots on my freezing feet. I-I don’t know . . . I just . . . I feel . . . better like this. It . . . just . . . feels . . . right.”

As the last word left my lips, something stirred within me. It was a feeling that something about what I had just said was extremely important and I was missing it. However, I pushed that thought away. I figured I was just nervous about revealing that I liked dressing as a girl.

Christine put her arm around me, gently squeezing it as she reassured me.

“Well, Kyle, this is all okay with me. I don’t see any wrong in it.”

Christine and I looked at her friends for support but we didn’t like what we saw. Christine asked — which was helpful because I couldn’t.

“Are you two okay?”

“I don’t know.”

“Me either.”

Sara looked alarmed. She hesitated for a moment and spoke her mind.

“Kyle, in that analogy about the freezing feet, if the person keeps walking around barefoot in those temperatures, the consequences are severe and potentially lethal if he can’t warm up his feet at some point. Are you saying that if you don’t dress as a girl sometimes that there could be severe and potentially lethal consequences? I mean . . . is there . . . somehow . . . a serious danger to . . . I-I don’t know . . . your well-being, maybe . . . if you can’t be a girl at least sometimes?”

I looked at her blankly.

“I don’t know. Maybe. I admit I haven’t thought about that. Maybe I haven’t needed to because I dress as a girl from time to time and have some relief . . .” There’s that feeling again like I just said something cosmically important. But what, damn it? “Well, to answer your question, until I know one way or the other, I think we’d better assume that my well-being is at stake if I don’t dress as a girl at least sometimes.”

“Holy shit!” Christine looked very worried.

“It’s only a possibility, though, not . . . an eventuality. Anyway, like I said, I haven’t had any problems yet and as long as I can dress as a girl sometimes, I don’t think we have to worry about that.”

“Well, I definitely support you dressing as a girl sometimes,” Christine resolved.

“I do, too,” Sara concluded. “That was the only thing bothering me.”

Sara relaxed, but Jill didn’t. She had her arms crossed in what looked like a defensive posture.

“You two are okay with this?” She responded.

Sara nodded and Christine concurred.

Jill momentarily covered her eyes with one hand.

“I-I’m sorry, Kyle. My parents are pretty conservative and, well . . .” she hesitated to say it. “They don’t say very good things about people like you. They think it’s wrong for a boy to wear girls’ clothes, like Biblically wrong.”

Oh, please not that! I inwardly groaned.

“But I don’t believe that. I mean, the Bible says that someone who commits adultery should be stoned to death but my parents would never support that. I mean, if we’re going to ignore the rules that we think are wrong, then . . . if dressing as a girl really is this serious a need for people like you, then I think that whoever spoke against it in the Bible made a big mistake,” she managed, pausing to take a breath.

“B-but . . . I’m still not comfortable with this," she continued. "It might just be because I haven’t met anyone like you before. I think I will probably get over it, but . . . not right now. I didn’t mind at all when I thought it was just a joke, but now . . . I don’t know. It’s so weird! It’s like . . . on the one hand I don’t really, truly see a problem with this, but it’s like . . . well, it’s like I’m brainwashed to think it’s wrong and so it’s scaring me anyway. I’m really sorry, Kyle. I don’t mean to hurt your feelings.”

“It’s okay, Jill. Finding me in nylons was probably not the best way for you to find out.”

“Maybe. I don’t know.”

“Well, Jill, um . . . Kyle needs this,” Christine put her arm around me again, “and so I want him to stay dressed as a girl while he has a chance.”

Although I could not explain why, I felt relief upon hearing her say that. Judging from the facial expressions of Sara and Jill, they noticed and felt at least some empathy.

“Is that . . . going to cause a problem?” Christine finished.

Jill thought for a moment, a crestfallen look appearing on her face.

“I-I . . . m-maybe I should go. I think I just need to let this digest for a while and that I will get over it, b-but . . .” She shook her head helplessly. “I just need some time to straighten myself out. I should go.”

Christine looked at her friend.

“Okay. If you feel it’s best.”

“Kyle, I’m sorry, I . . .” she shook her head again, clearly at a loss for words.

I stood up, making an effort to keep the peace.

“It’s okay, Jill. At least, you’re honestly trying to conquer your fears.”

“Yeah, I guess,” she half-whispered, nodding weakly before taking a strained breath. “I guess I'll . . . I’ll see you later, girls.”

She turned to leave, but stopped at the sound of laughter behind her. Without turning around, she put one hand on her head and hastily left.

Chapter 6 — Sunday, May 16, 2010

It had hurt when Jill had needed to leave, but I had had so much fun with the girls that I still felt good whenever I remembered the times they dressed me up.

“Hey, look who’s smiling!” Mira gently squeezed my hand as she grinned.

“Yeah, I was just thinking about the times when Christine and her friends used to dress me up. It’s funny, because it seemed so . . . harmless back then, but now . . . waiting for Mom to come down here . . . I feel like my life is at stake!”

My smile disappeared as my heart rate climbed steadily skyward the more I thought about it. Before I was aware of it, I was on my feet, heading toward the basement stairs.

“This was a mistake! Mom can’t see me like this; she’ll freak — and then she’ll have a shit fit! I can’t do this. I-I can’t!” I chattered nervously as I approached the stairs.

Mira was already on her feet, darting toward me.

“Honey, wait. Please.”

Mira closed the distance and took me warmly in her arms.

“I know you’re feeling afraid right now of how your mother’s going to take all of this,” she began, as she pulled back and looked me in the eyes. “But your mother has seen you in a dress before. More than once, right?” She glanced at Christine in time to see her nod.

“B-but she was the one who made me start leaving the house whenever Christine had her friends over.”

“Well . . . yeah. But it’s not necessarily because she doesn’t like you dressing as a girl. It could be anything! We just have to . . .” Christine trailed off.

“Wait and see?” I muttered.

“Yeah,” Christine agreed apologetically.

“What the hell’s taking them so long anyway?” I groused.

“I don’t know,” Christine admitted. “Knowing Mom, she’s probably on her goddamned cell phone!” She rolled her eyes. “But don’t worry. I’m sure she’ll be down soon!”

“Great!” I uttered.

With that, my mind fled the room.

PART TWO IS COMING SOON!

[ Other Stories By Mona Lisa ]