The Summer of Bailey: Part 4

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Zachary spends his first night away from home,
or at least his first night away as Bailey.
Through the course of the night,
he learns some hard truths about his relationship with Tiffany.
Thinking he has come to grips with the most complicated thing of the weekend,
Zach comes home to find things have gotten even more complicated...

The Summer of Bailey
by Taylor Ryan
Title image and story Copyright © 2010-2020 Taylor Ryan
All Rights Reserved.

 



Part 4

I could hardly sleep. Tiffany's arms held fast around me in a loving embrace. She felt so warm and so soft. The moon seeped through her window and lit up her angelic face. Her hazel eyes were shut in such a way where I knew there was contentment behind them. Every so often her smooth brow would twitch into a furrow, pulling her thin eyebrows down as she dreamed of things I could only guess about. Beneath her small straight nose, her pouty lips would part every once in awhile like she wanted to speak.

Several times I wanted to kiss those lips, but I feared waking her up. She obviously wasn't a light sleeper, as I had been running my fingers through her silky black hair for about an hour. At least she slept through that. I didn't want to wake her. Even though I had a ton of questions running through my mind, I simply wanted to watch her sleep. Her bare foot rubbed up my bare leg.

A few hours earlier we had returned from an all girl Fourth of July pool party. I managed to survive being Bailey for the party, with merely a swimsuit as my cover. In all honesty, nobody really paid much attention to Tiffany and I, as we hardly fit in with the older girls there. They were all Kate's crowd; Tiffany's older sister. The fireworks show at the high school was spectacular, and I enjoyed watching them with Tiffany. However, when we got back to her place, I started to feel a bit nervous about staying the night.

Tiffany took the first shower, giving me time to call my mother. I'd spoken to my mother twice that evening. Once to get permission to go to the party, and the other call to get permission to stay the night. Initially it had been my mother's idea to let me stay the night. When I called her back she seemed a bit reluctant, but still allowed me to stay. Her lecture on how to behave was nearly as long as Tiffany's shower.

I have to admit I was a bit shocked when Tiffany came back in the room wearing only her towel from the shower. She had the fluffy, dark red cotton rectangle wrapped tightly around her chest and dangling at her knees. Granted I had just spent the entire evening with her in less material, but it still shocked me. She closed the door to her room with the only audible sound being the click of her lock. Then she spun around to face me.

"Did your mom okay it?" she asked.

"Yeah," I said. "She gave me a long lecture about it, but she said it would be okay."

"I've been thinking all night of some way I could repay you," Tiffany said.

"You really don't have to," I said. "I had fun."

"I want to."

Tiffany moved her hands up toward the top of her towel. She pulled at the tight roll holding the towel on her body. After pulling it loose, she held the towel in place. Only her grip on the top of the towel kept it from cascading away from her body. She took a step forward. Her foot sank into the plush carpet. She took another step.

Each step she took toward me sent my heart racing more and more. I thought it would leap from my chest when she got within a step of me. She reached out and tugged at the white knit shorts around my waist. I took the hint and dropped them to the floor. Tiffany coaxed me to take a step forward out of the shorts. She reached up with her free hand, and pushed it gently onto my chest.

Do you think you can handle this?" she asked in a hushed voice.

I lifted both of my hands up to hers. Her hand was warm on top of the swimsuit material; the dark red swimsuit she had let me borrow to be Bailey. I placed my hands over her hand, and held it tightly against my chest. My heart pounded. I closed my eyes, and when I opened them I stared into her eyes. After a few calm breaths, I nodded.

"This only goes as far as I want it to," Tiffany said. "I want to do this, but if you step out of line, it's over." She lowered her eyebrows. "Understand?"

"I understand," I managed to choke out.

"I love you Zachary," she said.

"I love you too."

In all honesty, I didn't have a damn clue what love meant at the age of twelve. At least I didn't know what it meant on that level. I loved my mom and my brother. Tom could go trip into a dark hole for all I cared. I loved my goldfish when I was nine, but it died. Hell, I even loved some of my toys, and especially my bike. Yet this kind of love threw me for a loop. Maybe Tiffany knew more about what was going on than I did, but I still loved her with what I knew of love at that age.

Her towel slipped from her fingertips. It cascaded down her body into a pool at her feet. For a long moment I continued to stare straight ahead. The safest spot to look was at her face. She seemed timid, but also showed signs of the deepest sincerity. It was a look that eluded me at the time, but one I grew to understand completely as I grew older. When she reached out and pulled my right hand to her chest, I found her heart racing too. In fact, it was nearly beating with mine.

"Well?"

I continued to look into her eyes. "I'm not sure what to do," I said nervously.

Tiffany smiled, letting out a tense breath. "You can start by looking."

For some reason I felt like the only one not experienced in this area of life. My eyes drifted slowly away from their locked stare into Tiffany's eyes. I could see her tan starting to come in from the day. The area covered by her one piece swimsuit contrasted heavily with the darkened skin. Her breasts were pale white except for the dark pink areas around her nipples. I continued my exploratory gaze down past her belly button, which sat amidst smooth white flesh.

Half of me was scared to continue on down her body, but I felt a strong sense of curiosity weighing on the other half. Our "sex education class" in sixth grade was a somewhat informal half hour lecture by some doctor. We were split into two rooms with girls in one and boys in the other. So the entire lecture was about how boys would change on our side, leaving us clueless to anything else. While thinking about all of this, my eyes had settled on Tiffany's pubic area.

"You're beautiful," I said, as my eyes came back up slowly to meet hers.

"Thank you…" She took both of my hands in hers. "I was so scared to do this, but I wanted to show you." She hung her head down. "It sounds stupid doesn't it?"

"No," I said, "but you didn't have to…"

"I just wanted to show you something special," she said. "Because you've shown me something special about yourself."

"Well I think you're pretty special."

Tiffany's head shot upward. "Things like that," she said. "You're kind and sensitive. Not like the other boys our age." A smile grew on her face, which ended somewhere between cheery and content.

"I'm just being honest."

Tiffany threw her arms around me. As we held each other in a tight embrace, I felt a little uneasy. I could feel her warm body against mine, with only a thin piece of nylon and spandex between us. Instead of my hands holding some type of cloth, they held her naked flesh. I couldn't help, but to run my hands down her back. Before I could reach her bottom, she pulled away from me.

"Maybe we should get dressed," Tiffany said.

My hands jerked away from her. "I'm sorry."

"There's nothing to be sorry about," Tiffany said, assuring me with a kind smile. "I just don't know how much privacy we'll have. You can watch if you want."

"Watch you dress?"

"Sure," she said. "Why not? Women even used to help each other dress in the old days. How do you think they got each other into corsets?" She stepped over to her dresser. "Do you wanna help me dress?"

My mind was far from corsets and women helping other women dress. I stared at her smooth bottom bouncing as she walked. Somehow she had managed to get a little sun on it, so the lower part of her cheeks were tan. I figured she pulled her suit up a bit to get that effect. Then I realized she did that on me while I was first tanning. I made a mental note to check out the tan line damage in her bathroom mirror.

"It's not polite to stare," Tiffany said.

I looked up to notice her looking back at me over her shoulder. "Sorry," I said. "You're just cute back there too." My lips worked into a nervous smile.

"Well enjoy it while it lasts," she said, turning back to the dresser. "Might be awhile 'til I show it again." She started to rummage through the drawers. "Did you want to help me dress?"

"I guess so," I said, with the confidence of a ninety pound sumo wrestler.

She turned around abruptly. My eyes, which were fixated on her round bottom, now locked onto her pubic area. Something about it felt more forbidden. I decided that maybe it wasn't polite to stare after all, and my eyes started dancing around frantically. She noticed. Her hands fell to her hips.

"What?" She looked at me. "You can stare at my backside, but not the front?"

"I…" My eyes met hers. "It's just…"

"Have you ever seen one before?"

"No," I said. "I mean I've seen those weird diagrams at the doctor…"

"Weird?"

"Well, the area isn't weird." I glanced down again. "I meant the diagrams…" I looked back up at her. "You know what I mean."

"I do," she said, with a light giggle. She looked down. "It's called a vulva." She raised her head slightly. "And to be completely honest, I haven't seen… you know…" Her eyes hinted at my groin.

"Really?"

"Uh… yeah! Really! I wouldn't have said it if I had." Her sarcasm seemed distasteful, but lightened the mood.

"Do you want to?" I asked.

"Probably best if we didn't right now." She held up a pair of pale pink panties. "If you don't feel comfortable, you can watch."

"No," I choked out. "I can help you."

"Well come here then."

Tiffany enticed me to come to her with her index finger. After a few nervous steps forward, she stopped me. She pushed the panties into my hand. We both stood there in silence. Finally she gave a dramatic sigh and acted like her patience with me had run out. I didn't know what to do. She offered no suggestions either.

"What do you want me to do?" I asked quietly.

"Dress me!" she said.

I held out the panties in front of me at about waist level. Tiffany shook her head. She held out her hand with her palm facing out. I stood there ignorantly as she studied her nails. She glanced at me out of the corner of her eye. Then she turned her head to look at me straight on. She put her hand up to flip her hair out.

"Dress me like you would a princess," Tiffany said, feigning dramatic disinterest in me. "Like you're my chambermaid." She then pointed down at her feet.

"Oh!" I finally caught on to the little game we were playing. "I'm sorry… your highness."

"That's better," she said with a pleasant smile. "Now attend to your duties."

Most people would think Tiffany and I were nuts, but I rather enjoyed the little make believe games we played. I was always slow to catch on to when Tiffany switched to role-playing mode, but never unwilling to participate. The first time I dressed as Bailey at her house, she acted like a fashionista during the photos. There were other times we'd just randomly pick a part to play and go with it. I think most of the time Tiffany used it in uncomfortable situations to take our minds away from the more serious surroundings.

My knees sank into the plush gray carpet. I moved the panties toward her feet, but didn't hold them out for her to step into. Instead, I lowered myself even more and hovered my lips over her feet. Then with all the consideration I could muster, I lowered my lips onto the top of her left foot. I left a lingering kiss on the top of her arch, and then repeated it on her right foot. Afterwards I pulled back, and held out the panties for her to step into.

"You please me chambermaid," Tiffany said above me. "Perhaps I shall allow you to warm my bed tonight."

I looked up at her, trying hard to sustain my composure. Tiffany on the other hand appeared to be fighting back laughter. She reached down and patted my head. I almost laughed, but then looked back to the task at hand. Carefully I lifted the panties up her legs. My fingers grazed gently against her soft skin. They passed her knees.

About the time I reached her upper thighs with the panties, she put her hand down to stop me. I tried to look back up at her, but she held my head to where I stared straight ahead at her vulva. The smooth mound between her legs seemed a bit puffy now. I really hadn't noticed it before, but then again hadn't been looking too intently. Now I became even more curious.

"Do you think it's cute too?" Tiffany asked.

"Very," I said. "Not like what I have."

"And do you find the backside to your liking as well?" Tiffany turned in front of me, pushing her bare bottom close to my face.

"Yes princess," I said.

"You may kiss it if you like."

Truthfully I hadn't even thought of kissing it. I thought I would sit and stare at it for awhile. Then when I had sufficiently burned a mental image into my brain, I could finish putting Tiffany's panties on. However, Tiffany asked me to kiss it. She wanted me to show it affection. I still couldn't process this all in my young mind, but I decided to fulfill her request.

Gracefully I let my head fall toward her, and my lips fell soundly upon the left cheek of her backside. I believe at that moment I thought this was the thing my mother told me not to engage in, though she hadn't come out and said it in exact terms. Tiffany let out a soft moan when I made contact. I pushed my lips gently against her soft, yet firm bottom, and gave her a lingering kiss.

In fact, she allowed me to plant several lingering kisses on her bottom. I must have covered her backside with around twenty kisses. Eventually she put her hands on mine, and helped me pull up her panties the rest of the way. They stretched nicely across her tight bottom. I instantly drew a comparison of her bottom to Kate's bottom. Tiffany was already growing into her sister.

While I knelt behind Tiffany, looking at her bottom, she pulled out a flimsy pair of sleep shorts from the dresser drawer. She carefully turned to face me, and handed the item of clothing down to me. The shorts were a deep green color, and made almost entirely of satin. When I lowered them to Tiffany's feet she wouldn't step into them. I instantly figured out what she wanted, and lowered my face to give her another kiss on each foot.

"You're learning fast," Tiffany said, with a hint of laughter in her voice.

She stepped her left foot into the shorts, and then her right. The satin material glided up her legs. Without stopping, she allowed me to pull them all the way up. The elastic band stretched snugly across her hips, about three inches below her bellybutton. She patted me on the head again, and I looked up at her. Then she coaxed me to stand. While I stood, Tiffany had turned back to the dresser.

She turned back quickly. Her small breasts settled in front of my eyes. Though I didn't know cup sizes at all back then, I clearly know now that she was about halfway to an A cup. There definitely seemed to be an evident display of growth. I thought I had noticed it the other day, but now I was absolutely sure of it. Some tiny little part of me envied her breasts growing. Before long I wouldn't be able to easily pass next to her. She put a slinky top in my hands, the same color as the shorts. Then she held her arms out in front of her.

"Maybe I can teach you to pick out my outfits for me, and I won't have to work at all."

"Right," I said. "I'm sure your parents wouldn't mind me coming over every day to dress you."

We both shared a small laugh as I slid the top over her arms. I lifted it over her head, and she braced herself by putting her arms on my shoulders. The top fell gently over her body. It nearly met the top of the shorts, but left a bit of skin showing with her arms up. Her clothes felt so slick and slippery. I wanted to rub up against her, but I contained myself.

Tiffany crossed her arms behind my head, and leaned closer to me. I put my hands on her waist. Then I put my lips on her lips. For a small moment we kissed. She playfully rubbed her nose against mine, and then embraced me in a light hug, trying not to get her clean clothes against my swimsuit. Her hair, half dry and half wet, felt soft against my cheek. I wanted to hold her forever, but she pulled away too soon for my taste.

"I put a new toothbrush in the bathroom. You can wear the clothes I left in there," she said. "They're like these only blue."

"What about this?" I pulled on the swimsuit.

"You can leave it over the shower." She walked over and collected her towel from the floor. "There's all kinds of soap and shampoo in there. Just find what you like." She pushed the towel into my hand. "Take this with you please. Act like it's yours if anyone stops you."

"Sure no problem," I said.

"When you're done, come to Kate's room."

"Why?"

"She has all of those pictures we took on her computer," Tiffany said. "Thought you might want to see them."

"Oh!" I said. "I would actually."

"Go!" Tiffany said, walking over to unlock the door. "I have to talk to Kate about something."

Tiffany opened the door and let me out. I could hear a few voices coming from the living room. Apparently some of the guests stayed a bit later than others. Probably they had drank a bit too much, and were waiting to sober up for the ride home.

After checking to see if the coast was clear, I stepped out into the hallway. I heard soft music coming from Kate's room, and a blow-dryer. Tiffany slipped into Kate's room, and shut the door. Suddenly I heard a loud voice behind me.

"You lost?"

I turned to see Tiffany's dad at the end of the hallway. "I was just getting a towel from Tiff," I managed to squeak out. "She gave me something to sleep in too."

"Ah okay," he said. "So you all set then?"

"All set." I smiled. The poor guy was drunk, but a happy drunk at least. I imagined him seeing double of me, one side Bailey and the other side Zachary. "How was your night?"

"Oh… great!" he bellowed. "You girls have fun at the pool?"

"We had a blast."

"I'm glad you girls had fun," he said. "The hot on the shower sticks sometimes. I dunno if they told you, but fair warning so you don't burn yourself."

"Thanks," I said. "They did mention it."

He nodded a moment after processing what I said. "Well have fun, but don't stay up too late." He turned to walk toward the living room.

"Goodnight Mr. Stewart."

"Night…" He turned to give me a confused look.

"Bailey," I said.

"Right Bailey," he said. "Like the drink." He laughed to himself. "Baileys Irish Cream?" He smiled as he turned and walked off.

I rushed into the bathroom before anyone else could stop me in the hallway. All I needed was someone sober to corner me into a conversation, and they'd eventually figure out I wasn't a little girl. My mind seemed a bit rattled at the moment anyway. I pushed the door closed, and locked it quickly. Tiffany's towel dropped from my hand into a hamper near the door.

Their bathroom dwarfed the one at my house. It had two sinks, side by side, and a large mirror as long as the countertop. The toilet even had it's own private area in the corner, sort of like a stall in a public restroom. I figured for two girls getting ready in the morning, the bathroom seemed ideal.

They kept everything decorated in a dark red, with large velvety bath rugs over the tile floor. My favorite feature of the entire room happened to be the shower. Though they didn't have a bathtub, they had a large tiled shower. It came complete with an area to sit, large enough to curl up on and read a book. Tiffany sometimes called it a steam room.

I saw a pink razor sitting on one of the ledges, and imagined Kate sitting in the shower and shaving her legs. Then I imagined Tiffany soon shaving hers. Hell, the shower was big enough that I could've stood in it and watched without getting wet. For some reason I even thought about shaving my own some day. I turned to the mirror.

No wonder their dad still thought I was a girl. What boy in their right mind would paint his nails, throw on a one piece swimsuit, and pretty their lips up with lipstick? Furthermore, that boy would have to be insane to sit out in the sun all day and tan in that swimsuit. I must've been insane, because I did all of it. Not to mention my tan had turned out incredibly dark.

So dark, in fact, I started to panic. Even if I tanned in the morning, it wasn't a usual tan for me. When I tanned, it was a farmers tan, and fairly light. I seldom had my shirt off unless I went swimming. Though I did go swimming, my stepfather didn't know. Tom would think something was up if all of me showed up tanned as well. He'd wonder why I would take my shirt off at a cookout.

Yet I had to tan. If I revealed the tan line of a swimsuit to Tom, he'd be madder than hell. The more I had to worry about him, the less enjoyable this all became for me. I reached up, prepared to pull the straps of the swimsuit away from my shoulders. Suddenly I felt nervous tension ball up inside of me. As I pulled the swimsuit off, I felt a bit of relief. The tan wasn't as bad as I built it up in my own mind. It was nothing another thirty minutes of sun wouldn't cure. I just had to be careful not to burn.

I peeled the swimsuit down to my hips. Curiosity made me turn to look at my back. It looked like a mirror image of the front, but the back scooped in a lot lower. I was glad I moved my hair out of the way like Tiffany did. At least I got the tan up my neck. This could be fixed. I turned back around. It could all be fixed.

The sun did a number on my hair as well. I started the day with my normal dirty blonde hair. Now it had turned about three shades lighter. It did that any time I was outside in the sun for awhile. Not that I minded. I liked the unique quality of my hair. However, with my tan and the way my hair stood, I looked like one of those beach bunnies who sat for hours by the surf.

I pushed the swimsuit down past my knees, and stepped out of it. My tan resembled Tiffany's almost exactly. In fact, I looked like a girl with the exception of the male genitalia now falling back into place. Soreness crept into my scrotum along with the area Tiffany had banged up against in the shower earlier. I ran my hands over the area and found a slight bruise starting. When I rubbed my testes gently, I felt a dulling pain spread up my abdomen. I decided not to touch them again.

I removed myself from the passive gaze of the mirror. Scooping up the swimsuit, I walked to the shower and flipped it over the top. After a quick trip to the stool to relieve myself, I stepped into the shower. I closed the large fake glass door of the shower. The water came on warm. My head drooped, and my eyes closed as the water rolled down my body.

They had a ton of body washes in the shower, but the only bar of soap I found was Dove. It smelled alright, so I decided to use it. I instantly loved the silky feel it gave my skin. Growing up in a house of three guys and one woman, the only soap I knew was Dial. I recall in fourth grade we did some soap carving in art, and I begged to get Irish Spring. I thought it would be neat to carve green soap. Well, I got my request for art class, but was still stuck with Dial at home.

My thoughts on soap carried me through the mundane tasks of lathering up and rinsing. Then I stood and stared at the vast array of shampoos. They had everything from Nexus to Herbal Essence. I chose Nexus, as it had a sweet coconut smell. It left me in the mood in which my body and hair reflected. I felt like a girl who had been stranded on a deserted island.

After shutting the shower off, I stepped out into the colder room. Goosebumps lined my body, and I quickly reached for a towel. As I toweled myself dry, my eyes wandered over the outfit Tiffany left for me. It did indeed resemble the one I helped her into earlier. Though it had the same silkiness to its satin material, the color was a pale blue. Along with it were a pair of pale blue panties.

"Am I ever going to not wear panties?" I mumbled to myself.

I tossed the towel over to the hamper. My hands reached for the panties. I lowered them to the floor and put my right foot through one leg hole, and repeated the same with my left foot. They glided slowly up my legs, stopping when I reached my mid thigh. The soreness returned to my abdomen, as I began to handle my testes. I pushed through the pain, deciding I wanted them back up in my body again.

Finally they settled into the cavity above my penis. The pain slowly subsided. I pushed my penis back between my legs, and pulled the panties up the rest of the way. Instantly I noticed they were different. They weren't bikini style like I had bought, and they weren't the full brief like Tiffany's other pair. Instead they sat on my hips, not coming up fully to my waist. The feeling was different, unusual, but not displeasing. I think I still preferred bikini style.

I ran my fingers across the satin shorts. Then I gathered some of the material and rubbed it between my fingers. It felt so soft and slick. I'd never worn anything close to it in my life, and here I was about to sleep in it. I slowly removed the shorts from the towel rack. Stooping over, I held them low enough to step into. I took my time dragging them up my legs.

They felt fantastic. The satin felt cool and fluid, almost like liquid sliding up my legs. When they reached my hips I could feel them gently brush my upper thighs. They had the feeling of covering, but yet not being there. I ran my hands over them. My hands slid across them, gliding from my hips to my backside. I had to wear more.

Luckily the matching top hung delicately within my grasp. It slipped over my head with ease, and flowed down my upper body. Now I felt the full effect of the outfit. The material felt light, slick and soft all at the same time. It didn't cling like cotton. Instead it slid when I moved, gliding across my skin, which was now silky itself from the soap I used.

While I could have stood there all night rubbing myself, I thought maybe Tiffany would miss me. I gathered myself together, and stepped over to the mirror. The small straps of the top failed to cover the inch wide area of white the swimsuit left. I picked up the toothbrush Tiffany had left for me.

As I brushed my teeth I noticed with the lipstick gone, I looked too much like my former self again. Even if I managed to get past a few drunk people tonight, I still might have to deal with their parents in the morning. Granted with my tan and hair lighter, I did slightly look like a different person. If anything, the shock of them realizing it was Zachary, would give me enough time to get a running start.

I spit the toothpaste out. Maybe they wouldn't notice. Maybe, like my mom, they wouldn't care if I was Bailey. I filled up a small Dixie cup with water, and rinsed my mouth out. Then I drank a couple of glasses full of water. With one final look in the mirror, I worked up the courage to exit the bathroom.

The hallway was quiet, and I had no problem slipping into Kate's room. Kate stared intently at her computer monitor. Tiffany, on the other hand, showed her enthusiasm at me walking into the room. She waved me over to them, and patted an empty chair. I walked over and sat down quietly. My back faced the door.

Very few times had I seen Kate not personify femininity. This happened to be one of those times. Her nails were plain. She had no makeup on. Her attire was something my brother would wear to sleep in. It consisted of gray jersey shorts about knee length, and a plain white tank top. The scene honestly surprised me.

"I like this one," Kate said.

Tiffany scooted up to the edge of her chair. I looked at the monitor. The picture on the screen surprised me. It was me. I mean it was me as Bailey, in a white blouse with a Peter Pan collar, a light blue skirt, white tights and strappy white sandals. The makeup Kate had applied to my face, exploded in the picture. It created an image of a young teenage girl, with a sultry look.

"It's about the time Bailey here started to relax and be herself."

I couldn't argue. The next few pictures Kate flicked through, amplified her statement. She wasn't aiming to be cruel, but I literally became Bailey in those pictures. I not only looked like a girl, but my poses were extremely feminine. It worried me a bit. Either I embraced the character of Bailey for the moment, or…

"She really broke out in that last one," Tiffany said.

Kate clicked back one picture. I sat and stared at myself in the monitor. The stance wasn't inspired by anything. Kate hardly gave direction for the photos. I was just being silly that day. My left foot was planted firmly on the floor, barely angled inward at the toe. With my right leg I had turned the knee inward, and kicked my foot up and out sideways. The toe of my right foot dangled about an inch above the floor.

I continued to look at the picture. My left hand tugged down at the hem of the skirt, while my right hand had somehow twirled a lock of hair around two fingers. As I pulled down on the skirt and my hair, my face contorted into a very effeminate pout. What in the world was I thinking at that moment?

"Keep going," Tiffany said.

"They get really good when she starts changing outfits," Kate said.

The pictures got worse, at least for me. They might have seemed to get better if you were looking for keepers. However, from my point of view, they showed a story of a boy slowly turning into a girl. Through each wardrobe change, I became more and more comfortable as Bailey. By the time we reached the outside pictures, you would be hard pressed to find an objective audience to say it wasn't two girls being photographed. No wonder Tom flipped when he saw us running around. He saw me not only dressed as Bailey, but acting as Bailey.

"Wow!" I said quietly.

Kate and Tiffany both turned to look at me.

"What?" Kate asked.

"I'm such a girl…"

Tiffany started laughing.

"I'm serious!" I said, as I turned my head to face them. "I didn't realize how girly I was being that day."

"That's why I was confident you could pull tonight off," Tiffany said.

"Not to sound cruel," Kate said, "but you're really good at being Bailey,"

"I don't think I can do this anymore," I said.

"Why?" Tiffany asked.

"What if I got used to acting like that?"

"Again, not to sound cruel," Kate said, "but you have certain… quirks as Zach."

"Certain quirks?"

"I've been watching you for awhile," Kate said. "You're kind of…"

"Sissy?" I started to became a little belligerent.

"No!" Tiffany said.

"Not at all," Kate said. "There's just some feminine qualities to you."

"And so what if it is sissy," Tiffany said. "It's totally not a bad thing to be that way."

"Yeah," Kate said. "It's hardly a negative thing in my opinion. I mean I personally think it's great." She paused. "It's refreshing."

"Totally!" Tiffany said. "It's what I love about you."

I focused on Tiffany "Are you into girls?"

Kate chuckled, while Tiffany's face got bright red.

"It's okay if you are," I said. "You seem into this though."

"I guess you could say I'm curious," Tiffany said. Her voice got lower. "I've never… you know…" She looked down at the floor. "I thought if I could find some kind of middle ground…"

"Are you serious?" Kate asked, as her laughter slowly subsided.

Tiffany glanced at Kate, and then looked straight at me. "I'm sorry if you feel I dragged you into it."

My thoughts trailed off. I had no place to look. Between the two girls and the monitor, I felt ashamed to look at any of them. I had a girlfriend that loved me, but now I felt I had to be another part of me to be loved. Kate seemed like a counselor on the other side, knowing intimate details about our relationship, but not partaking in it. Then here I was as Bailey, not even able to stand up for myself as a man, or at least a boy. It all felt so humiliating.

"I am so sorry," Tiffany said, while placing her hand on my knee.

"I don't know what to say," I said.

"Well…" Kate spoke up. "We can start with this. Do you like Tiff?"

"Of course!" I took Tiffany's hand in mine. "I love her."

Tiffany smiled, though a tear streamed down her left cheek.

Kate looked at her sister. "Now how do you feel?"

"I…" Tiffany closed her eyes and took a deep breath. Her pretty hazel eyes opened. "I think I'm in love with Bailey."

There it was again. That empty feeling filled my stomach. I felt sick, but couldn't act upon it physically. Tiffany held my hand tightly. I could feel the edges of her fingernails in my skin. Fingernails I had painted, and where they led eventually was to this moment right now.

No. I looked down at her feet. This moment started building from the first time I painted her toenails. I knew it for a fact now. Painting a girl's toenails is not something little boys do. It eventually led to them dressing up as little girls. That was the truth I made up in my own mind. I looked at the monitor. Something still had to be said.

"I can't be Bailey," I said, turning to face Tiffany. "Not all the time."

"I think we all know that," Tiffany said with a half smile.

"Well there is a way," Kate said.

"How?" I asked, stunned by her statement.

"What's your stepfather's email address?" She gave me a wicked grin.

"That's not even funny," I said.

"Sorry," Kate said. "Just trying to lighten the mood."

"Look… I don't know how long this all can last," I said. "Maybe there's little pieces of Bailey in me all the time, but I know I can't be her all the time."

"Then I'll take the little pieces," Tiffany said. "I'll take whatever you want to give me."

"I hope you're planning on waiting a long time for that," Kate said.

Tiffany turned to talk over her shoulder. "I wasn't talking about sex."

"Good!" She turned back to the computer. "The way you two were all over each other tonight, I'm surprised you haven't done it already."

"We're way too young," Tiffany said.

"Honestly," I spoke up, "I'm scared to death of sex."

"Really?" Tiffany asked.

"Yes!" I looked around, unable to focus on anything. "I'm not sure what to do. It scares me."

"You seemed pretty comfortable tonight in the shower," Kate said.

"How did you know about that?" Tiffany asked.

"Oh come on," Kate said, turning to face us. "Two girls disappearing for half an hour is nothing to most people." She turned back to the computer. "But I knew what was up, and I saw you coming out of the shower."

"Not like we went all the way," Tiffany said.

Kate spun around in her chair to face us. "So how far did you go?"

"Well I don't know," Tiffany said. "Quite a ways?"

"Don't look at me," I said. "I have no idea."

"Define quite a ways," Kate said.

Kate laughed at our confusion. Though the entire scene felt completely embarrassing, I felt more comfortable discussing it after. I started to wonder if this is how typical girl chat went. If so, it was a lot more interesting than the conversations I'd had with boys my age. The only problem was, I really had no basis to judge it all on. I was as new to discussing sex, as I was to having it.

"We just made out," I blurted out.

"Well that's not very special," Kate said. "That's something a guy would say."

"I don't know what else to say," I admitted.

"How did it feel?" Kate asked.

Tiffany looked at me. I suppose she expected me to get a crash course in this type of conversation. Maybe she was embarrassed. Then I started to think maybe she didn't know how to engage in this conversation either. I'd thought earlier she maybe had a mature educated view on all of this, but now I wasn't so sure. I decided to take a stab at it.

"It was warm," I said, "and wet." I spoke to Kate, but focused on Tiffany. "The water from the shower made everything so smooth." I tried to recapture the moment in my mind. "Every second of it was exciting. Slow kisses with water cascading down our faces." I closed my eyes. "Everything seemed slow and methodic. Like the shower controlled it all." I opened my eyes again to look at Tiffany. "Gentle, calm… moving together."

"I just got a chill," Tiffany said, letting go of my hand.

"That was really good," Kate said. "A lot better than what you said before."

"Ladies," their mother's voice came from behind me. "I think you all should be getting to bed."

"A few more minutes?" Tiffany pleaded.

"Okay," their mother said, "but only a few."

"I'll get them to sleep," Kate said. "Goodnight mom."

"Goodnight," Tiffany said.

"Goodnight Misses Stewart," I said over my shoulder.

"Goodnight Bailey," she paused. "Girls, I mean it. Not too late."

Kate waited until their mother left, then she tapped my knee. "Tiffany told me about your little dilemma," she said. I watched her get up and go to her dresser. "We have a bit of a dilemma too." She pulled a bundle of material, with a mess of straps hanging from it, out of her middle drawer.

"Dad goes in to work at about nine," Tiffany said. "Mom leaves around ten."

"I have to be at work at three," Kate said. "Which means I need to leave here before two-thirty to drop you off across town."

"So we'll have plenty of time to get you tanned," Tiffany said.

"Right," Kate said. "I think we can get a modest amount of privacy in our backyard."

"So what's the problem?" I asked.

"I desperately want you to tan in a two-piece," Tiffany said.

"What?!" I straightened up. "Why?"

"I think it would look so cute, with the tan lines and all."

Kate held a strappy two-piece swimsuit up.

"See!" Tiffany said. "The thin little straps would look adorable."

"But it would completely defeat the purpose of hiding the fact I tanned in a bikini."

"She's kidding," Kate said, unable to hold back her laughter. "She wanted to see what you'd say."

"I'd say no!"

"This is mine," Kate said. "We'll be tanning with you."

"This one is yours," Tiffany said.

She took another swimsuit bottom from her sister and handed it to me. No surprise, but it happened to be bright neon pink. I unfolded the small bundle of material. They were tiny, and not from lack of material. Though they had very little material to speak of, they looked to be two to three sizes too small. When I pulled on them, however, they had a lot of stretch in them.

"Trust me. They'll fit," Kate said, as if reading my mind. "They're going to be snug, but they're perfect for your situation."

"And just incase someone does happen to stop by," Tiffany said. "Here's the top."

She handed me the other piece. It was bright neon pink as well, but looked like one continuous loop of material. Kate called it a tube top, but I honestly wasn't up to speed on the lingo of female attire at the time. I put the two pieces together, and draped them over my lap. Tiffany got up, took the swimsuit from me, and walked to the door.

"Kate wanted to discuss something with you," Tiffany said. "So I'm going to go finish getting ready for bed, and I'll see you when you're done."

"Okay," I said, with a fair amount of reserve in my voice.

"It won't take long," Kate said to Tiffany.

She closed the door behind her sister. I watched her wander around the room collecting things. My mind tried to find some kind of earthly answer why the door would need to be closed for just talking. Kate didn't seem to be doing anything out of the ordinary either. She finally came over, adjusted her chair, and sat down facing me. When she pulled herself closer to me, I shifted uncomfortably. She placed her hands firmly on my knees. Then she gave me a pleasant smile. I relaxed a little bit.

"Tiff and I had a little wager."

"Oh?"

"I bet her if I dressed like this, you would pay more attention to her."

"I take it you won?" I asked.

"You're a smart little girl," Kate said.

I ignored being called a girl. "What did you win?"

"Well, let's just say you got your little fantasy," Kate said. "I kind of promised the other day, but then your stepfather came and all that."

Kate leaned back and put her left foot up. She squeezed it into the space between my thighs. It finally rested firmly against my trapped penis. Her toes wiggled back and forth. I could hardly sustain my composure. Kate seemed laid-back about the scene. She shook a bottle of clear basecoat, and eventually handed it to me.

"You totally have a foot fetish," Kate said. She was smiling. "It's really not all that uncommon." She put a box full of various shades of polish in Tiffany's vacant chair. "So take your time, and enjoy." Kate leaned back in her chair to relax. "Choose whatever color you want." She leaned forward again. "I expect a kiss on each foot when you're done." She smiled, and then leaned back again.

I busied myself with applying the basecoat. Kate busied herself with relaxing and being pampered. Truth be told, I really enjoyed doing it for her. It was sort of a reward for both of us, from a bet between her and Tiffany. I started to wonder what Tiffany would've wanted for winning. Then I decided to not think about it, and enjoy what I had. I was so busy with what I was doing, that I didn't notice Kate had leaned back up to watch.

"Would you let me style your hair tomorrow?" she asked.

"As long as you don't cut it," I said.

"No, nothing like that," Kate said. "I was thinking maybe curl it after you tan."

"Sure," I said. "Sounds like fun."

"Cool," she said. "You know… you're really a lot of fun Bailey."

"Thanks," I said. "Wish I could trade you for Justin."

"He's not so bad," Kate said. "Just needs to get off his jock ego trip."

"Yeah… football really changed him." I started to rummage through the colors of nail polish. "I think maybe he feels pressured by Tom to do it."

"Maybe he needs to take a break from hanging around Tom all the time?"

"I don't know," I said. "I wish Tom would take a break from life."

Kate and I talked almost the entire time I painted her toenails. We really got to know each other. She even dragged it out longer and let me do her fingernails. By the time we finished, my hair had dried completely. I knew Tiffany was missing me, so I rushed to put everything away for Kate. She knew I wanted to get out of the room, but she wouldn't let me until I got down on my knees and kissed her feet. Then she thanked me, and ushered me from her room.

Soon after I left Kate's room, I found myself in Tiffany's bed. All things considered, it wasn't that horrible being Bailey. Only Tom really put a damper on it all. Since Justin hardly talked to me, I really had very little resistance. My mom seemed far from against it, even encouraging it to some level. Kate treated me like a sister. Tiffany loved Bailey. As I drifted to sleep in her arms, I started to wonder if I could stay Bailey.

I awoke, somewhat late in the morning, to Tiffany's soft lips leaving playful kisses on my face. As I came more aware of my surroundings, I started to kiss back. She scooted toward me, and I moved closer to her. Before long we were rubbing our hands on each other, over the satin material of our clothes. Our bare legs rubbed together.

When I started to kiss down her neck, she pushed me away. I watched her slip out of bed. She pulled the sheets off of me, and then retrieved something from her dresser. A sly and mischievous smile spread across her face as she crawled back onto the bed. In her right hand she held what I made out to be the neon pink bikini bottoms.

"Since you helped me dress last night," Tiffany said, "I thought maybe I'd help you."

I started to scoot away from her. "I'm not so sure."

"Please?" She tugged at my borrowed shorts.

"Do you really think we should?"

"Are you nervous?"

"A little," I said.

Tiffany straddled my lower legs. She tugged back and forth on the sides of the satin shorts until they were down to my knees. I put my hands on her thighs, in an attempt to get away from her. As I squirmed beneath her, she pulled the top up and over my head. She slipped it down my arms, and managed to pull it off when I lifted my hands away from her.

By this time it had become more of a playful attempt to get away from Tiffany. While I felt uncomfortable about the whole ordeal, I honestly didn't put up much of a fight. Tiffany pushed me back down onto the pillows. She started planting gentle kisses on my shoulders and neck. As she continued to kiss down my chest, she wiggled out of her own top.

I wiggled as well, still pretending I wanted to get away. Yet as she continued to kiss me, I lost the will to fight after awhile. I moved my hands up to her waist. My fingers hooked in behind the elastic band of her shorts. In a matter of seconds I had pulled them down her tan thighs. She rose up on her knees to let the shorts go down further. After a lot of squirming and worming around, our shorts finally slipped from our feet.

Tiffany moved up to lay on top of me. She pushed her body into mine. I started kissing her neck on the left side, and she returned the affection on my own neck. Her hands slid into my hair, and pulled at it gently. Then she started rubbing her pelvis into mine. She shifted to where our left thighs ended up rubbing between each others' thighs.

She continued to slide up and down my body. I moved my hands up and down her bare back. Eventually I pushed them under her panties. Tiffany moaned as I squeezed her bottom. It felt so smooth and firm. She kept rubbing against me until her panties had shifted down to her thighs. Then she pushed into me, continuing to rub against me harder.

Her breathing became ragged. She pulled at my hair a little harder. Soon she had stopped kissing me, and just continued to slide up and down my body. I couldn't resist kissing her neck. Her skin had the faint smell of pear and raspberry. I figured it was one of the body washes they had in their shower. She moaned, and I kissed her more.

After a few more minutes, Tiffany began to tremble. She pulled her upper body away from me, and held my head down with her grip on my hair. Her hips grinded into mine a few more times, and then she stopped completely. I watched her for a few minutes hold her position. Then she gently collapsed on top of me. Her grip loosened from around my hair, and she lowered her hands to run them up and down my upper arms.

I ran my fingers up her back. Several minutes passed in silence. Then I felt Tiffany's thigh start to rock forward between my legs. Her head tilted back. She pushed her lips up against the bottom of my chin. As she continued to rock her leg against my groin, she kissed down my neck.

Before long, Tiffany had me softly moaning. She kept rocking her thigh against me. At one point she grabbed onto my shoulders for leverage. Her kissing became as relentless as her rubbing against my entrapped penis. I felt it twitch inside my borrowed panties. She kept going.

The whole time Tiffany rocked against me, I could feel her body sliding against mine. Her whole body was warm, but her pelvic area felt warmer and wet. It started to glide in the area above the top of my panties. Tiffany pushed up, bracing herself with her forearms. She looked into my eyes and grinded her thigh into me a little harder.

After several more thrusts, I started to breathe harder. My penis twitched several times, and then started to convulse. Soon it was convulsing with each thrust of her thigh. I moaned loudly, causing her to push her lips into mine. She kissed me hard. When I'd calmed down a bit, she pulled away from the kiss. Then, after a few more kisses on my lips and cheeks, Tiffany slid down my body.

She took my panties off as she went, pulling them slowly down my legs. When she had pulled them completely off, she knelt next to me on the bed with them in her hands. Slowly and methodically she wiped my penis off. Apparently it amused her to see an actual penis for the first time. She took great care in cleaning it off, and studied it carefully. Eventually she finished, and dropped the panties next to her bed with the rest of my clothes.

"Did we just have sex?" I asked, nervous about even talking to her.

"I'm not sure," Tiffany said, "but I think we just had lesbian sex."

I stared at the pleased expression and smile she had on her face. Then I smiled too. She was so cute, and neither one of us really knew what happened. I even felt like Bailey at the moment, and that seemed fine with me. It obviously felt fine with Tiffany. She had moved down to my feet and started to pull on my swimsuit bottoms.

Kate had said they'd be snug, but that seemed to be an understatement. When they had reached my thighs, Tiffany had to pull hard on both sides to keep them going up. She nudged me to raise my bottom in the air. Then she pulled them up almost all the way. I helped her by adjusting my genitals, and then she finished pulling them on.

They were tight. In fact, they were almost too tight. As I lowered my bottom back down on the bed, the bikini bottoms pulled in every direction. My groin felt extremely constricted. I shifted around, and I could feel them pull up on the bottoms of my cheeks. Tiffany ran her hand over the front of them.

"I can't even tell you're a boy," she said.

"That is the idea."

"The pink looks so good with your tan legs. I can't wait to see the rest of you tanned."

Tiffany leapt from the bed. She dropped her panties to the floor. I rolled over to sit on the edge of her bed. The clock read twelve o'clock. Their parents had to be long gone. I watched Tiffany slide into a pair of dark blue bottoms. She smiled at me, apparently not caring that I watched her. After putting on the matching top, she opened her door, checked to see if the coast was clear, and then we set out to go tan in her backyard.

Tanning wasn't as exciting as it had been the day before. At the party I had been secretly hiding my identity. Now it just felt like tanning. Even though I sat between Tiffany and Kate, it came nothing close to last night. It even felt like I was Zachary again, wearing only bikini bottoms. I enjoyed being Bailey at the party and even afterwards. I think I even would have enjoyed being Bailey now.

After tanning, and taking a quick shower, Tiffany led me into her room. Like Tiffany had done the night before, I now only wore a towel. As Kate setup what she needed to style my hair, Tiffany had me get dressed. To my surprise she had picked out a pair of hot pink panties in a bikini style. I watched her walk them over to me. She pulled the towel from around my waist.

"I picked these especially for you," Tiffany said.

"I was hoping you'd have my own underwear," I said.

"These are," she said. "I mean, I'm giving them to you. I want you to have them."

"You want me to wear panties too?"

"Well, I thought since you have to and all…"

"I could've left my male underwear here to change into," I said.

She shook her head. "If my parents found them, they'd ask way too many questions. Besides, it'll keep you out of trouble with your step dad."

"I guess you're right."

"I know I'm right," she said, handing me the panties. "Now put them on." She turned back to her closet. "I have the rest of your stuff here. Unless you want to go home as Bailey?"

"I better not," I said.

I pulled on the pair of hot pink panties. Tiffany met me just as I settled into them. She handed me my jean shorts from the other day. After slipping them on and fastening them, Tiffany helped me put on my t-shirt. Then I sat on her bed and slipped my shoes and socks on. I stood, and Tiffany gave me a quick kiss.

"I'm glad to see you again," she said.

"But wish Bailey could stay?"

"Yes, and no," Tiffany said. "I love your girly side, but I think having it be a secret is more exciting."

"It's not much of a secret," I said. "If Tom had his way, I would probably be Bailey all the time."

"Have you ever thought of letting him catch you?" Tiffany asked as she opened her door.

I stepped out into the hallway. "I never wanted him to catch me in the first place."

"Well he said if you did it again, he'd make you wear more," Tiffany said. "I was just wondering if he got you to wear enough, you could just be Bailey all the time."

"I think there's a lot more to it than clothes," Kate said. She stood at her door. "Now come in here and let me do your hair."

"This will go away with a shower right?"

"Right," Kate said. "I'm just going to curl it."

She brought me into her room. I sat in the chair at her computer desk. Tiffany walked over and sat on her sister's bed. Kate had put out an assortment of things on her desk. There were a couple of brushes, a long comb, a box of hairpins, and a round contraption with steam coming out of it. She walked over and picked up the hairdryer and turned it on.

As Kate dried my hair, she brushed it out. She kept going until my hair was nearly dry. While she did this, she explained she wanted to use hot rollers, and wet hair could make them possibly burn me. In the small mirror I could see Tiffany smiling behind me. She seemed excited to see the outcome.

Kate put the hairdryer down and brought the comb up to my hair. She started by parting my hair into three sections. First she gathered the entire top of my hair and clipped it together for one section. Next she took the sides together and clipped them together. The last section, the back of my hair, she started dividing into several smaller sections.

She would comb one of these smaller sections out, and then roll it up with a small roller from the steaming contraption I'd seen earlier. When she got it all rolled, she'd put a clip in it to hold, and then move to the next smaller section. Kate put about six rollers in the back section, and then moved on to the next section; my sides.

Again she divided this larger section into smaller sections. Going the opposite way as the last section, she put several more rollers in. One by one, the small rollers left the steaming round contraption. The girls made comments back and forth to each other about how cute I'd look after. Tiffany claimed I looked cute before they started. Kate mentioned I looked cute the other day. A huge part of me wished I was dressed as Bailey at the moment, but even the lack of clothing didn't stop me from feeling like Bailey inside.

When Kate had finished putting rollers in my hair, she began checking it all, fidgeting here and there. I think I ended up with a total of sixteen small rollers in my hair. Kate continued to fuss over it a little more, and then told me she had to get a shower for work. She told Tiffany to take me into the other room. Then she mentioned she'd take the rollers out and finish up before she took me home.

While Tiffany and I waited on Kate, we had some watermelon in the kitchen. I still swear to this day that Tiffany lived on the stuff. She ate a ton of it. We made small chat, the whole time listening for Kate to call us back in. Time seemed to tick away slower than molasses, but eventually we heard Kate call from the other room.

We stepped into Kate's room as she was finishing up putting her uniform on for work. She pointed to the chair for me to sit down. I quietly sat and watched her put her makeup on. She fixed her own hair into a quick ponytail, and I felt a bit ashamed she had spent all the time on my hair and not her own. After stepping into her shoes, she came back over to me.

She quickly started taking pins and rollers out of my hair. With each one removed, she would comb out my hair with her fingers. After taking out the entire back section, she combed it all together with her fingers, making it blend a bit. Then she repeated the process with the next section. Once she got done with the top section, I had a ton of small bouncy curls.

"She looks adorable," Tiffany said.

"Yeah," Kate said. "It turned out better than I thought it would." She leaned over me. "If you wanted it to stay longer, I would've put hairspray in it to hold." I felt her hands on my shoulders. "You might get in trouble though if you can't make it go away quickly."

"It's a shame it has to go away at all," I said. "I really like it."

"I love it," Tiffany said, walking up to kiss me on the cheek. "It's so Bailey."

"Well…" Kate looked at her watch. "Bailey has to go be Zach now." She turned to her sister. "So say your goodbyes quickly." She removed her hands from my shoulder and started wandering around getting her keys and stuff.

Tiffany pulled me to stand up. "You look amazing," she said, running her hand on my cheek. "I wish you could stay longer, maybe do something with me."

"I wish I could too," I said. "Mom wanted me home at a reasonable time though."

"I understand." She leaned in and gave me a tender kiss on the lips. "I'll miss you."

"I'll miss you too."

"Let me know if you wanna do that party," Tiffany said. "We can plan ahead and set it all up for you to go as Bailey."

"I'll think about it," I said. "I'm not so sure how much longer this Bailey thing will go."

"I hope it can continue for awhile," Kate said. "I'm having fun practicing looks on you."

"Bye Zach," Tiffany said, giving me another kiss. "And Bailey." She gave me a hug.

"Bye Tiffany," I said as we broke the embrace. "I'll call you later."

"Let's go girly boy," Kate said with a wink. She ushered me out of her room, and eventually out of their house.

About fifteen minutes later, Kate dropped me off at my house. The entire ride from her place to mine, she had glanced at my hair countless times. If I didn't know any better, I'd say she was extremely proud of her work. I had to be honest. She did a good job. I loved how my hair looked, but I wished I could wear it like it was permanently. We also had an interesting conversation about me taking the berating comments from Tom as compliments. Kate even revealed to me that she thought the term sissy was cute.

I thanked Kate for the ride. Then I thanked her for my hairstyle. She mentioned she would do it again anytime I'd let her. I kept this offer in the back of my mind. I'm sure I would take her up on it. I pushed open the car door, and hopped out. After closing her door, and giving her a quick wave goodbye, I climbed the stairs to my front door and let myself inside. My mother's voice carried down the stairs as soon as I closed the door.

"Zach is that you?"

"Yes," I shouted back.

"I didn't expect you so soon."

"Where are you?" I started to carry myself up the stairs.

"I'm in your room," my mother said. "I have something to show you."

"What?"

"Just come here."

I shuffled up the rest of the stairs. She probably had more nail polish to give me or something of the sort. My mother always read into stuff way too much. In fact, she seemed to be more interested in Bailey than Tiffany or I combined. Maybe it stemmed from her not having a daughter. It was hard to tell what she even thought of the entire situation. I stepped into my room and was greeted by a large pile of clothing on my bed.

"Oh my!" my mother said. "Somebody got some sun." She walked over to check me out, reaching for my hair. "And a new hairstyle I see."

"Kate did it," I said. "Do you like it?"

"I love it," my mother said. "It looks darling." She continued to play with the small curls. "It's a shame you can't keep it like this. I think she did an excellent job."

I looked to my bed. "What's all this?"

She turned to the bed. "After our little conversation the other night, I took the liberty to get you a few things."

"Clothes?"

"Now before you get excited, some of it is fairly old," she said. "I tried to get some stylish things, but there isn't much selection at a consignment shop."

"A what?" I asked.

"A consignment shop honey," she said. "It's a place where you can buy second hand stuff."

"Like Goodwill?"

"Not exactly the same, but close." She stepped over to the pile of clothing. "The clothes at consignment shops usually aren't worn out as much as a thrift store."

"Why?"

"Because they're usually clothes that were outgrown quickly, or worn for one season, and only accepted in good condition."

"No… I mean why did you buy all of this?"

"Oh!" She chuckled a bit. "Well I thought you…" She gave me a solemn look. "I thought if you wanted to explore Bailey a bit more, this would be the cheaper option without being the cheapest."

"I can't be Bailey."

"Can't be, or don't want to be?"

"I don't even know if I want to be," I said. "It was fun this past week, but I can't do it all the time."

"Well, unlike Tom, I'm not forcing you," she said. "But right now you have a window of opportunity to explore your options. At least until you outgrow it."

"With Tom around?"

"Tom's not always around. He's even thinking about getting a night job," she said. "If you want to be Bailey around me I won't say a word."

"What about Justin? He'll tell on me any chance he gets."

"I'll be having a long talk with him if you choose to continue with this," she said. "But he has two-a-day practices soon, and then he'll be staying after school until football is over."

"That's true…"

"Look, it's up to you kiddo. Whatever you want to do." She put her fists on her hips. "You got the hair right now to play around with. Besides… wouldn't you like to wear your own clothes to that birthday party?"

"I don't know if I'm going to that," I said. "Tiffany only mentioned it."

"Well you sounded excited about it on the phone last night."

"I think it was just because she was excited about it."

"Were you officially invited?"

"Bailey was, but I think they'd all flip if they found out the truth."

"Look," my mother said. "You've been out in public twice as Bailey. Once under the extreme scrutiny of other girls, and they couldn't tell the difference."

"That's true…"

"I'd say after what you did last night, and if your hair is any indication…" She folded her arms across her chest. "Actually by the hair alone, I think you would like to explore this further."

"I do," I said, glancing at the floor. "But Tom…"

"Screw Tom," she said. "This is about you. I'm not going to force you into these clothes, and I'm not going to berate you for wearing them. You have to decide if you want to be Bailey, Zachary, or even both."

"I suppose I could at least think about it," I said, looking up at her. "You did go to the trouble after all."

"It wasn't much trouble." She gestured with her hands. "It can always go back, or I can donate it elsewhere if you don't want to do this."

My voice trembled. "Can I try it on?"

"Of course," she said. "I'd like you to try it all on, but even just trying on what you like suits me." She sorted the top of the pile into shirts and bottoms. "At any rate, could you at least go through these and see if you like any of it?"

"I'll try them on."

"It's settled then." She pointed at the floor in front of my closet. "Shoes too. I got a few pairs, but we can get you some different ones if you want. If you'd feel comfortable going as Bailey to try things on, we can do that too. There are a few bras in here." She picked up a small bra from the bed, and dropped it again like she was scared to hold it. "If you decide to continue this, I would prefer we buy your undergarments new. Panties, bras, even tights and pantyhose later. We can get all of that." From the corner of my eye I could see her mulling over the clothes. "If you need my help for something, don't be embarrassed to ask."

She had lost me at the word shoes, and she didn't even know it. "Thanks mom," I said, as I stared at the shoes. They captivated me.

"I'll leave you to it then," she said, as she brushed past me into the hallway.

My door was shut in about ten seconds. What was it about shoes that interested me? Kate had to be right. I definitely had a fetish, as she called it, for feet. Maybe I had a fetish for shoes as well? I kicked off my sneakers, and nearly ran over to the shoes. Everything on the bed seemed like second favorite to me at the moment. It could've all been on fire screaming for me to save it, and I still would've run over to the shoes to rescue them.

The selection confused me at first. I didn't know what my mother was thinking when she picked out the shoes. Then I realized she had quickly covered several occasions with her choices. A cute pair of white mule sneakers covered anything casual. I could even wear them to Tracy's party. Wait! Did I really want to go to her party?

I picked up a pair of black ballet flats. They looked almost exactly like Tiffany's pair of flats, only they had a decorative flower cutout on the toes. I figured I could wear them casually, if I didn't want sneakers, or for slightly more dressy occasions. The next pair I picked up were a pewter color. They were a dress sandal, with thin straps running everywhere, and a chunky two inch heel.

When I picked up the fourth pair, I started to think of all the situations where I would be wearing these shoes. Then I started to wonder why I was thinking about dressing as Bailey for those situations. The shoes were cute, and a big pull for me dressing. This pair in particular happened to be black Oxfords, with two and a half inch tapered heels. They were probably the cutest ones in the bunch.

The last two pairs of shoes interested me the most. While the other four pairs were a size four and a half, Tiffany's size, these two pairs weren't. My mother had bought me a pair of really dark gray leather boots in a size five. They were almost black, but looked sort of faded. The block heel on them was a modest inch, maybe slightly over, and they looked like they would come to mid-calf on me. I think they were my favorite pair, perhaps because they looked comfortable.

Looking at the last pair, I noticed they were a size five and a half. The size didn't intrigue me as much as the style of the shoe. Even Tiffany didn't have anything like them, but I knew for a fact my mother did. She wore them to work all the time, and called them pumps. I'm not sure why they were called this, but it didn't seem to bother me much. I studied the four inch heel. It tapered down into a half circle about three quarters of an inch wide at the bottom.

I wondered why my mother decided I needed this pair. Perhaps she thought I might want to dress up like she does for work. They were a nice pair of shoes. The sole and heel were a light tan color, while the rest were a dark navy blue. I'm sure I could find something to wear with them in the pile my mother bought. However, I wasn't so sure I could walk in them.

All of the ideas about outfits, and thinking about what to wear each pair with, got me excited enough to check out the clothes. It couldn't be put it off any longer. I had to see what my mother got me. Tossing the pump down into the pile of shoes, I pulled myself away from them. In a matter of seconds I had pushed myself from the floor to stand. I turned toward my bed.

The clothes confused the hell out of me. When I arrived at my bed, and started to dig through the pile of clothing, I was shocked at the sizes. They didn't make any sense to me at all. Some of them had size twelve, while others had size seven to eight. I still couldn't figure out how the large could be the same size as the small. There were even a pair of extra small jeans with a glittery design on the right leg. I decided to try them on first.

Though I had only dressed as Bailey a few times, it seemed to bother me less each time. In fact, I could probably handle going back and forth to her at will. I could be like a cross-dressing superhero, or heroine. It wasn't exactly clear in my mind which one of those it would be. Perhaps I'd let my admirers choose my true identity. Maybe the confusion could be one of my special powers?

I shook my head. With a slightly amused smile on my face, I pushed off my shorts. Tiffany's hot pink panties greeted me. Actually they were mine now. She had given them to me. The unusual circumstances to which they were obtained still disturbed me. In some weird way I felt like she was going along with my stepfather's punishment.

She could have at least kept one pair of my male underwear over there. I could've worn them as a backup, and even taken my nail polish off at her place. Instead she threw them away, claiming it would keep me out of trouble with Tom, and keep her from being questioned by her parents. However, it still seemed like she wanted to go along with Tom's idea. She didn't show any signs of pity or remorse for putting me back into panties.

I kicked my shorts off to the side. After stooping to lower the jeans to the floor, I put my right foot in one leg. Then I put my left foot in the other leg. The jeans slid up my calves and past my knees. When I got to my hips they seemed a bit snug. I kept going, pulling at the waistband. Finally they slipped over my hips and fell into place at the waist.

The first thing I noticed after I fastened them, was the fit. They weren't tight, but they were snug. In fact they hugged my bottom, and continued to be snug down to the top of my knees. This is where they started flaring out toward the bottom. Examining the bottom of the right leg led me to the second thing I noticed. The glittery design was a pinkish trail of soft loops, which led ultimately to a butterfly in full flight on the thigh.

"How cute," I said to myself.

My shirt flew from my body. I dug my hands into the pile of clothes. After about a minute of randomly tossing articles of clothing aside, I realized I only had three choices in bras. There was a light gray sports bra, a white training bra like Tiffany's, and then a beige bra with some sort of padding in it. For some reason I had to experience this one.

On the tag another size confused me. It read thirty-two A. I needed to ask my mother or Tiffany what all of these sizes meant. However, it could wait. I slipped the bra over my arms. With a little effort I managed to get it hooked closed in the back. After a few moments of adjustments, I had the bra fitting me snugly. Now I just had to decide on a top. There was a light knock at my door.

"Come in," I said, still digging through the pile of clothing.

My door slid open. "How's it coming?"

I turned to face my mother. "Okay I guess."

"What's wrong?"

"Nothing's wrong," I said. "I just…" I looked at the clothes. "I'm a little confused by sizes is all."

"Oh." My mother chuckled. "Don't worry about that. I'm forty-two, and I still don't get it sometimes." She walked over closer to me. "Some of them are girls sizes, and some are juniors." She started to rummage through the clothes. "I took the sizes from Tiffany's clothes the other day, but a lot of it has been guess work."

"So they go to a certain size and start over?"

"Sort of," she said. "I'm not going to bore you with the details." She pulled a shirt from the pile. "Try this one."

I took the shirt from her. The shirt was simple, with no design, but had a nice tan color. It also had what I later learned were cap sleeves. As I slipped it on, my mother went to open my curtains. Light poured into the room. I tugged at the shirt, but couldn't manage to pull it down past my belly button. My mother smiled as she walked over to me. I, however, continued to tug on the shirt.

"It's a crop top," she said, as she pulled my hands away from the hem of the shirt. "They're supposed to be like that."

"I just thought it was too short."

My mother chuckled. "You got a nice tan," she said, running her hand lightly across my navel. "The color of the shirt really brings it out, and this style shows it off."

"The jeans might be a bit too small," I said.

She put a couple of fingers behind the waistband and gave it a few tugs. "Turn around."

I did as she requested. My mother tugged at the waistband in the back. She checked how much the pockets gave in the back. Then I felt her hand gently slide over my bottom. When she nudged me to turn back around, she brushed her hands down the thighs like she was smoothing the jeans out. I watched her evaluate the front for a moment.

"They look perfect to me," she said.

"They're a little tight."

"Well they're not the baggy old jeans you're used to wearing," she said. "You'll get adjusted to them."

"What if I don't?"

"Then you can just wear them until you do," she said with a wink. "It'll be nice, for a change, to see you in something besides baggy seconds from your brother." She walked over to my dresser. "I hope you don't mind, but I replaced your socks. White for now, but we can add other colors if you want." She pulled a pair from the top drawer. "They're also lighter material, and they'll barely cover your heel, but I think they'll be easier to go back and forth in."

I took the small pair of socks from her. "Always thinking ahead."

"Speaking of thinking ahead," she said. "Is there a particular reason you chose the push-up bra?"

I shifted uncomfortably. "I thought it would look better if I had… you know…"

"I thought so," she said, with a wink. "In that case would you like me to get you a few more like that?"

I sat down on my bed. "Don't you think you've gotten me enough?" I asked, gesturing at the clothes.

"Well we can wait on it." She waited for me to take my old socks off, and then she took them from me and tossed them in the trash can. "I thought maybe you'd like to get some of it out of the way before school starts."

"I'm not going to school as Bailey," I said.

"Oh heavens no!" my mother said. "I just meant you'd probably be busier then." She walked over and sat on my bed. "Junior high is hard enough to adjust to as it is."

I sat down on my bed next to my mother. She busied herself with continuing to sort my "new" clothes. I brought my right foot up to me, and slipped one of the socks on over it. At first I thought they were too small, but realized they were supposed to fit like they did. While my regular old ones came up and covered my ankle, these didn't even reach my ankle. They came about halfway up my heel as well.

"Those go great with the mule sneakers I got you," my mother said. "If you want to wear socks with them, the socks won't show as much." She continued to mess with the pile of clothes. "They also have ones that show less than that."

"Think it'll take a while to get used to them," I said, as I slipped the other one on my left foot. "But I like them." I stood up, ready to go put on my shoes.

"You have a lot of things to get used to," she said, holding up another pair of pants. "Try these." She sat for a moment staring at me. "Would you like me to leave the room?"

I recalled Tiffany's mention of women helping other women dress. "You're fine," I said.

I reached for the button on my jeans and unfastened them. As I wiggled them down over my hips, my mother smiled at me. They slid down my legs, and I stooped over to pull them off of my feet. Then I folded them neatly and walked over to the bed. My mother continued to give me a pleasant smile as I exchanged the pants.

"Cute panties," she said.

"Tiffany gave them to me," I said. "To keep."

"Oh?" My mother raised her eyebrows. "Does she like it when you're Bailey?"

"More than when I'm Zach, I'm afraid."

"Do you like being Bailey when you're with her?"

"She makes it more fun I think," I said. "But I'm starting to just like being Bailey."

"Are you saying you want to be her more?"

"I think I am…"

I held the pants down low enough to step into. My right foot slipped into one leg hole, quickly followed by my left foot in the other. As I pulled the pants up my leg, I realized they were tighter than the jeans. However, the black material they were made of stretched quite a bit. They slipped up over my hips and settled at my waist.

These pants were definitely different than the jeans. First, they were snug, all the way to my knees. For some reason they ended two inches after that. Second, there were no zippers or buttons on the front, but instead there was one zipper on the right side. I pulled the zipper up, making them sink in at the waist.

"Those are called Capri pants," my mother said. "Sort of an in between of jeans and shorts."

"I like them," I said.

"Put on the Oxfords with them," my mother said. "They should look good with them."

I did as she asked, and stepped over to get the pair of Oxfords. As I walked back over to the bed, it appeared my mother seemed to be enjoying having a daughter for the moment. She watched me slip on the shoes, which fit perfectly. Then she smiled as I tied them and took a few paces around the room. I stopped to look at her.

"What's next?" I asked.

She handed me a tube of lipstick. Nothing in my mind even gave me pause to question it. I took the tube, and headed to the mirror. The tube said Toast of New York on it. Apparently my mother was up to speed on the fashions for younger girls. I quickly applied the lipstick, blotted it, and then applied a second coat. Lipstick application seemed like the easiest thing to master.

"Well…" I spun around to face my mother. "What do you think?"

"I think I was right all along."

My mother and I both jumped, and turned to see Tom standing outside of my door. He had this sort of pissed off, but victorious look on his face. I stood frozen, unable to throw any excuse out there to justify my situation. My mother sat on my bed in silence. The pleasant smile had been wiped from her face.

"I've been saying it for years," Tom said. "You're nothing more than a little sissy faggot."

"I…" Tears formed in my eyes.

"You have proven it time and time again." Tom put his hand on my doorframe. "You know it's funny… I called the Stewarts' asking for Zachary the other night. Apparently he never showed up." He glared at me. "Then I called back a bit later and asked if Bailey made it there okay." He slammed his fist against my doorframe. "Wouldn't you know it? Bailey was out at a damn all girl pool party!"

"Tom," my mother said.

"Shut up," Tom said to my mother. He turned to face me. "From now on, forget the rules. Do whatever the hell you want to do, since you do it anyway. Hell… you can do it as Bailey for all I care. In fact… you can just stay Bailey the rest of the summer." He glanced at my mother and then focused on me again. "But I'm taking you to see someone about it."

"See someone?" I asked.

"Yeah," Tom said. "A specialist who deals with little sissies like you." He looked at my mother, who seemed like she was about to argue. "End of discussion!" Tom nearly yelled.

He turned and walked down the hallway. Before long he was yelling at Justin to bring in the rest of the gear from their fishing trip. I walked over and sat on my bed. Tears started to stream down my face. My mother sat next to me in silence. She put her arm around my shoulder and held me close. For the next several minutes I sat there, unwilling to speak, thinking of what could be and what would be. I could be Bailey, but would it ruin me?


 
 
To Be Continued...
 

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Bailey

ALISON

'will prevail and Tom is going to be a sore loser.What a peanut!

ALISON

I'm still of a mind that

I'm still of a mind that Bailey's Mom needs to tell Tom to F***off and take a hike. He is the very type of person whom I believe would actually become physical with both the Mother and Bailey if they don't bend to his will. He is a bigoted, narrow minded, intolerant person who is most likely dangerous to boot. Sadly, he is trying to raise Justin to be just like him and it already shows, as Kate mentioned earlier to Bailey. WHY would Tom be checking up on Zach/Bailey if he was not a control freak? Guess you could say I really don't like this man at all.

The Summer of Bailey: Part 4

If that turd tom knew what Baily did, turd tom might not be such a turd. And I do apologize to all the turds even excrement deserves respect.

    Stanman
May Your Light Forever Shine
    Stanman
May Your Light Forever Shine

For some reason I see Tom

For some reason I see Tom being told to go take a long walk off a short pier... And If he's actually around long enough to take Bailey to 'see someone', that the someone will diagnose Bailey with Gender Identity Disorder (or Gender Dysphoria, which ever we're calling it now...) and his plans will be busted.

Sorry Tom, but I believe that Bailey is here to stay...

Samantha

Unfortunately

Tom is the type to take Zach/Bailey to see someone who claims to be able to, "cure the gay," out of someone. Like the church that Ted Haggard was head of that later claimed he was all "better" and straight now.

wow

wow, where is is this going? is zachs mom going to stand up to tom? what kind of doctor is he thinking about? and poor zach through this. good story. keep up the good work.
robert

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Zach or Bailey?

What is interesting about this story is that the internal
turmoil that this young man is going through is being displayed.
It appears his girlfriend, and her sister may have issues.
That the mother may have a desire for a daughter and she may
add to the pressure that pushes Zach to be Bailey more than
is healthy for him. Tom is not a bad guy he is just trying to
to keep his son on the right track. His methods may be primitive
but that could be the result of his up bringing. The question is
what is right for Zach. Being Bailey on a long term basis may not
be right for him.

Interesting story about the stresses facing a young boy.

Not a bad guy?!?

Edeyn ANY adult who derides or berates a child just because they are not small clones of the adults around them is a bad person. You said, "... he is just trying to keep his son on the right track," but he is NOT Zach's father, he's his stepfathead, and why is forcing him to be the close-minded, homophobic, transphobic type, "on the right track," at all? Society needs less people like this guy.
More than just his methods are primitive, so is his way of thinking that men must be large and muscular. Some men are simply not able to be the large and musclebound types, but they're still men. Why is being the kind of man that is afraid to show any kind of emotion a desirable thing? I do agree that being Bailey for good may not be right for Zach, but it is up to ZACH to decide that without being forced one way or the other. His mother encouraging him is fine because she's made it clear that she's not going to force him -- it's clear she would enjoy having Bailey around to be her daughter, but it is also clear that she loves her son for who he is and not because he is that potential daughter. Tom is an asshat, and the worst kind of guy, whether he gets physically violent or not.

Edeyn Hannah Blackeney
The Infamous Intersex Transgender Asian Lesbian Atheist Chick of the Ozarks
Wasn't it Jim Henson who said, "Without faith, I am nothing," after all? No, wait, that was God... Sorry, common mistake to make...

Feeling...

I'm getting a feeling that Tom is slowly changing. He wasn't so angry this time. He seems worried about Zach in his own way. He even remembered the name Bailey. :)

Krista

A lot of anger there

Wonder what caused it. What happened in Tom's past that makes him so angry? And I noticed he suggested help, but of what kind? I would definitely be a little wary of any help he might be suggesting...
Great story as always :)
Hugs
Diana

Nope, IMHO Tom is high ..

... or should that be 'low' on the list of people to be avoided. Loud, aggressive, controlling - probably frightened of any feminine characteristics in himself.
Way back at the beginning of this tale, we are told that Tom died in his prison cell, so methinks Tom is gonna do something criminal.

Global_warming_proof.jpg

Just double checked ....

... Tom "took his own life in prison". J.

I'm addicted to this

Just as I was thinking that I wish my mom had been like Zach's mother, Tom came in and spoiled everything. The way that Zach's mom just sat there and let Tom shoot his mouth off, in spite of the fact that the entire situation was her doing... well, let's just say that my opinion of her went down a notch. I certainly hope she redeems herself in an upcoming chapter.

Bailey's girl friend and

Bailey's girl friend and Mother are all right..Think his step dad needs an attitude adjustment..

alissa

Two kids need a long talk

Jamie Lee's picture

Zach wasn't sure about nail polish, but let it happen. Zach wasn't sure about makeup, but let it happen. Zach wasn't sure about being dressed by Tiffany and Kate, but let it happen. And Zach wasn't sure about the swimsuit, but let it happen.

Each time Zach has offered token resistance to the activities. And each time he's had fun, and felt at ease. Zach says he's not sure about being Bailey but his action say something else. Kate, Tiffany, and his mom can see he enjoys being Bailey. Zach does want to be Bailey but he's afraid of losing Zach in the process. So he tries to convince himself he doesn't want to do something he is doing with glee.

Someone soon, needs to sit both Tiffany and Zach/Bailey down and have a very frank talk with them, before they do something which will really be a big problem. While they've had a talk with limited information, they really need specific information before things get out of hand.

The way Tom is handling the entire situation makes him out to be the biggest booger on the planet. As long as he doesn't become violent, verbal rants can be tolerated. They may not be liked, but can be tolerated.

Another thought about Tom's anger. While he could have grown up being taught to act as he does, he could also be frightened. And acting angry is the only way he knows how to exhibit his fear. He may have known someone like Zach who ended up being physically harmed because that person didn't measure up to the standard of bigger boys. And he's afraid the same thing will happen to Zach.

Without knowing anything about Tom's past, the only thing that can be said about him is that he's egotistical jerk. And is in the process of ruining his marriage.

Others have feelings too.

I think that Tom

and my mother would have deserved each other. This is very nice.

Sad but hopefull

I think it is sad to make such a choice forced ar that age (or any age). I really hope she will be alright in the end.

A bit confused about the mom. She is supportive but when Tom is there, well, she isn't there to protect her son. That is so sad....