The Summer of Bailey: Part 2

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Zachary's punishment stirs up some very confusing questions in his own mind.
His stepfather forces him to stay in Tiffany's clothes for the rest of the night.
As he trudges through the morning the next day,
he finds even more questions waiting to be answered...

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

 



Part 2

I was amazed at how one innocent afternoon of fun could put my stepfather, Tom, back on my case about being a sissy. Not only did he begin his berating comments again, but now he pressed the issue until it became a burden. I followed him and my brother, Justin, into our small house, stopping at the middle entryway area of our split level stairs to close the front door behind me. Part of me expected my stepfather to start slapping me around, though he had never done anything beyond a firm spanking. The other part of me feared the dynamic changing in my relationship with all parties involved.

For a moment I stood and watched Tom and Justin walk up the stairs to the living room. The air condition vent next to me blew my borrowed black tiered skirt around. I had been caught by my stepfather and Justin at my girlfriend Tiffany's house, playing dress up in her clothes. It was her skirt that swayed atop my bare and hairless legs. I stood in her black ballet flats and her hot pink t-shirt. Everything on me was hers, from the makeup and hot pink nail polish, to the matching white cotton panties and training bra I had on underneath.

All of the attire would have been agreeable to my stepfather, had it not been on a twelve year old boy. It had all started as a game with Tiffany, but turned out to be the beginning of a long punishment from my stepfather. The punishment began with the contents of the bag in my hand. They were things he forced me to buy.

When he started thinking up my punishment, he had me purchase my own panties. I bought an assorted pack of twelve, so I had thirteen in all with Tiffany's pair. He also had me purchase my own nail polish, which he claimed I would be wearing for the duration of the summer along with my new panties. I started to think of how I could live out the next two months, when I noticed my stepfather turning to face me at the top of the stairs.

"I don't want you changing before your mother gets home," he said. "She needs to see this."

"Well I can't help with fixing the dishwasher in these," I said. "I'll ruin Tiffany's clothes."

"Like I need a woman's help to fix something." Tom said. "Why don't you go wash your new panties?"

I knew it was a rhetorical question. Tom laughed as he turned to head into the kitchen. My brother walked back through as I was climbing the stairs. He looked at me with a confused smirk, and shook his head. It was one of those you're-up-shit-creek-without-a-scented-paddle looks. By the time I reached the top of the stairs, my brother and stepfather were busy at work in the kitchen. I started to head back to my room when I heard my stepfather yell.

"If you change your clothes I'll beat your ass to where you can't sit for a week."

I continued on down the hall to my room. Over the years I had learned not to take my stepfather's threats lightly. So I decided to do exactly what he suggested. I took the package of panties out of the bag, and tossed the rest of my purchase gently onto my bed. When I picked up the panties from the store, I was so nervous that I hardly looked at what was in the package. Faced now with ample time to investigate what I bought, I ripped the package open and spilled the contents onto my bed spread.

My eyes beheld the vibrant colors before me. Two pairs each of plain white and light pink, were quickly cast to the side. I held a red pair for a few seconds, running my fingers over the material. Though they all were one hundred percent cotton, they felt lighter and silkier than my plain old male briefs. They also had a bit of a lace design on the waistband. I tossed the red pair, along with a darker pink pair, on top of the white and light pink pile. Then I moved a pair of peach and a pair of lavender to the solids pile.

The other four pairs of panties consisted of an array of different patterns. One pair was royal blue and teal in horizontal stripes about an inch wide. Another pair was white with multicolored pencil thin horizontal stripes. There was a pair of light blue ones with light pink flowers all over them. The final pair were white with pink and lavender dots. I picked these up to read the instructions for washing them.

While I read the tag, it became increasingly obvious that I would have to hand wash each pair. Even though they said machine wash was okay, none of them really had like colors except for the dual pairs. I figured I could wash the whites with the pair of Tiffany's I was wearing, but the rest were gonna take a bit of time. At least I would have time to think of what I would say to my mother. Not to mention I would be alone, away from my stepfather and brother.

A few minutes later I was in the bathroom with my arms full of panties. I turned the water on at the sink, and quickly cleaned the basin. Then I switched the water over to cold, plugged the drain, and added some Woolite to the running water. I decided to put the red and dark pink pair in first, and let them soak.

While the first pairs soaked, I stared at myself in the mirror. Kate, Tiffany's older sister, had done an awesome job with my makeup. I looked about three years older, perhaps four. At any rate, I didn't look like someone about to start junior high, but someone well into high school. Not only that, but I looked extremely feminine. I really hadn't taken in the entire effect at Tiffany's house, as we had been having too much fun.

My almond shaped eyes seemed bigger, and their steely blue color really exploded beneath the smoky gray eye shadow. She had made my already thin eyebrows appear to taper off at the outer edges with the makeup pencil she used. My lips, which had always been a bit on the pouty side, appeared filled out more, and the natural bow shape I had on top looked more pronounced. Even my small bell-shaped nose looked different with blush on it. Combined with the blush on my cheeks I looked a bit flushed, almost blushing. The makeup and powder, she put on the rest of my face, made my face appear smooth.

I turned my face a bit. The clips Kate had put in my hair glittered in the light. Where she had placed them, turned my otherwise boring chin length hair, into something flirty and fun. My wavy hair fell in various spots all over, while it was lifted in other spots to give a bit of a layered look. Somehow my hair, along with the makeup, tricked my eyes into thinking my slightly square jaw line had been rounded out a tad.

Something about the way I looked and felt at that moment seemed right, but an overwhelming sense of trepidation came over me when I thought about what my entire punishment would be. My eyes dropped back down to look at my new panties soaking in the sink. These could be just the start. I felt certain that Tom had it in for me.

After watching the tiny bubbles pop and disappear for a few minutes, I reached down and pulled the plug from the drain. As the water ran out of the sink, I recalled the way my mom dried her own delicates. I reached under the sink and got an old dark brown towel out. I spread the towel out on the front of the sink. Then I rinsed both pairs of panties with cold water, until I felt the detergent had been sufficiently washed out.

I gave both pairs a gentle squeeze and set them on the towel. Next I rinsed the sink basin a bit, and plugged the drain back up, being sure to add some more Woolite. I decided to put the light blue with flowers in with the blue and teal striped pair, and then added the lavender pair in, thinking those would be ok to wash with them. While the sink filled, I busied myself by rolling the red and dark pink pairs up in the towel. I turned the water off, and then gave the towel a gentle twist, leaving the first two pair to dry a bit, and the next load to soak, as I left the bathroom.

When I sneaked down the hall a bit, to check where my stepfather was, I overheard him talking to my brother about me. He mentioned something to the effect of my brother keeping an eye on me, and to tell him if I ever dressed in girl's things again. Great! Now I'd have that to worry about. It was bad enough we both had to worry about all his low-life buddies telling Tom when Justin and I did something wrong. I felt like I had no privacy even running around with my friends.

I walked back down the hallway to my room. There I picked up my bag from Wal-Mart, and pulled out all the nail polish I bought. My stepfather's punishment wouldn't be absolutely horrible, as I kind of enjoyed painting my nails. However, his promise to make me have them painted all the time, didn't sit well at all. It would be okay around Tiffany, if I ever got to see her again, but around my male friends was a different story. I carefully placed each bottle of nail polish on my dresser.

I pulled out my gum from the bag, and realized the gum in my mouth had lost all flavor. I spit it into the bag. Then I opened up another piece and put it into my mouth. Chomping into a fresh piece of strawberry bubble gum felt relaxing. I tossed the package up on my dresser, and tossed the wrapper in my bag. I wadded the bag up, pretending it was my stepfather's head, before tossing it into the garbage can on the way to check on my panties.

It took some getting used to, thinking about the panties being mine. At the time I bought them, I thought it would be a horrible punishment to wear panties for two months. However, the more I thought about it, the weirder it seemed that my stepfather had me purchase panties. If anything he would cut girly attire out completely as punishment, if he thought I was wearing it on purpose. I shook it all out of my head as I stepped into the bathroom.

My reflection in the mirror still shocked me. I was a pretty little lady, so far removed from the cute little boy. At least my mother always referred to me as the latter. Tiffany thought I was cute, and though I didn't have any self-esteem issues, I didn't think I was ruggedly handsome like all the other boys. Even Kate thought I was cute, but did they both think of me as cute in the effeminate way? That to me was the million dollar question. It was a question I didn't have an answer for at that time in my life.

I unrolled the old brown towel on the countertop, and removed my first two pair of panties. I set them aside. Then I pulled the plug from the drain, and rinsed the next three pairs out. Again, I gave them a quick squeeze, and placed them in the towel. Next I rinsed the sink again, and filled it for the last load of light colors. As the sink filled up, I rolled the panties in the towel, and gave it a gentle twist. Before leaving the room, I put the two light pink pairs in with the peach pair, and added the multi colored striped pair and pair with the dots.

After turning the water off, I exited the bathroom with my five clean pairs. I went to our small laundry room, and set them on the counter in there. While I was looking around for clothespins to hang them to dry, I heard my mother coming in the front door. She was a little late getting home, but way too early in my mind. I heard her not so subtle, but soothing, voice carry up the stairs.

"I need Zach or Justin to come help with the groceries."

"Zach go help your mom," my stepfather's voice came from the kitchen.

What a bastard! I was hoping for a subtle sit-down-and-bring-me-in type reveal, but now Tom had forced me into a shock and awe approach. I'd been so busy with laundry that I hadn't even formulated my side of the story in my head. What on earth would I say to her? I thought I better give her a little warning, something subtle. However, Tom took even that away from me, as he exited the kitchen and his next comment rang down the stairs.

"Your son wants to show you what he's been up to today."

I finished hanging my panties on the small clothesline. For a split second I thought about wrapping the plastic-coated wire around my stepfather's neck and holding on for the ride. Hell, who was I kidding? I wasn't a killer. He'd probably kill me first. When I stepped out of the laundry room, Tom was waiting at the end of the hall. He wiped his hands on a rag, as he stood near the top of the stairs. Maybe I could run and push him…

"Well go on and show her," Tom said. He looked down at my mother. "I don't think you can even guess this one Sue."

"What is it now?" my mother asked.

Tom turned to go back into the kitchen. I slowly walked down the hallway toward the corner. Right before I turned the corner, I took a long breath. When I stepped out of the hallway, and looked down the stairs, my mother's face changed about three times. At first she laughed, but quickly covered her mouth. Then she got this confused look on her face, like she was questioning every question she ever had about me. Her last look was just a subtle eyebrow raise with shake of her head.

"Looks like we have something to talk about," my mother said.

"It was Tiffany and Kate…" I looked behind me to see if Tom was there, and then looked back at my mom. "We were just goofing around, and Tom came by…"

My mother smiled, still shaking her head. "Well come on down and get the groceries out of the car." She started to walk up the stairs. "I'll have a look at you when you're done."

She put her keys in my hand, and brushed by me into the kitchen. I walked slowly down the stairs, and went outside to get the groceries. When I got outside, our nosey neighbor across the street had about twenty double-takes on my appearance. I quickly opened the trunk of her car, and grabbed the three bags inside. I heard the footsteps of someone coming down the sidewalk, and struggled to close the trunk with all three bags in my arms.

"You need some help miss?"

I turned partially to see a young man walking over to help me. He got over to me right before I dropped a bag of groceries all over the driveway. While I situated the other two bags in my arm, he held the third and closed the trunk for me. Now I had never taken interest in how guys looked, but this guy didn't look bad at all.

He had short dark hair, about an inch or two on top, which I couldn't tell if it was black or dark brown in the dusky light. His evenly spaced eyes were an absolutely gorgeous shade of chocolate brown. Not to mention he seemed pretty fit. He probably played some sport, most likely in high school by the looks of it.

"You got it?"

"Yeah," I said, having to shake myself out of staring at him. "Thanks."

"Not a problem. I'm Nathan Riley." He held his hand out, and I shook it with the two free fingers I had left. He smiled at this, and his smile seemed perfect. "I just moved in down on the corner."

"Well it's nice to meet you," I said, as I took the third bag from him. "I'm Bailey." I thought I had better give my girl name so as not to confuse the poor boy. Then I thought he might expect to see me again, and quickly cooked up a cover story. "I don't live here. I'm just visiting my cousins."

"Oh," Nathan said. "Well nice to meet you. Glad I could help you out there." He flashed his gorgeous smile again. "Seems you were struggling a bit."

"Thanks again."

"You take care," he said, as he took off jogging down the street.

My heart was fluttering as I closed the door to the house. I didn't know if I was having a panic attack, or it was purely nervous tension. After gathering myself a bit, I proceeded up the stairs with the groceries. As I neared the kitchen, I could hear my mom and stepfather talking about my situation. I didn't like what I was hearing either.

"The panties are one thing, but you can't just make him go around with painted nails for two months,” my mother said. "What will his friends think?"

"Maybe it'll make him think," my stepfather replied. "I've tried my damnedest to get that kid to take on some manly responsibilities, but it's obviously not working."

"The kid is twelve Tom. He's just having fun with his girlfriend. What's the harm in that?"

"He needs to learn that certain things in life have consequences."

"Maybe if you'd quit running him down," my mother said. "You act like this is proof, or some reflection on all those degrading things you've been saying about him from the start."

"Well it sure as hell doesn't contradict what I think!"

"I used to dress up my little brother all the time in my things. It's just something girls do when they're bored, and to be quite honest, the boys are usually bored enough to go along with it."

"He can find something else to do if he's bored," Tom said. "I dish out twenty dollars a month for these kids to have an allowance. You would think they could use the damn money to find something entertaining to do."

"You honestly think your so called solution, is going to fix a problem?" my mother asked. "He probably doesn't even have a problem."

"Just let me handle this one," Tom said. "I think I've got it under control."

"Fine…" my mother said, "but you're paying the damn bill when the kid needs counseling from it."

"Then I'll make damn sure it's the kind of counseling he needs," Tom said. "Maybe I should take him to see my doctor, instead of that female one you drag him to."

"She's perfectly qualified."

"Whatever!" There came a long dramatic pause, before Tom added his final statement on the matter. "You leave him to me Sue."

"He's all yours Tom."

I waited a few moments to go into the kitchen. I figured if I came in a little slow, they might think I didn't hear the conversation. When I felt the time was right, I pushed open the door. I walked into the kitchen and looked at them both like I was clueless as to what had transpired. My mother looked at Tom, then shook her head as she walked over to help me with the bags. Tom walked over to me, and looked me over.

"Since he had so much fun playing a girl today," Tom said to my mom, "I'm sure he won't mind playing one the rest of the night." He looked me in the eyes until I lowered my head. "Help your mom cook supper, then you can do the dishes after." He brushed past me to exit the kitchen. "We got the wrong damn part for the dishwasher. So we're heading back to the store before it closes.” He stopped to yell down the stairs to my brother's room, as the door shut behind him. "Come on Justin! Let's go!"

My mother and I put the groceries away in silence. I handed her a couple of cans to put in the cupboard. She looked at me and smiled. It felt warm, and looked like she knew exactly what had transpired that day. She did mention she dressed her own brother up, so perhaps she understood all of this was done in fun. When I handed her a jar of pickles to be put in the refrigerator, I heard the front door slam shut. Mom turned to look at me again with a smile.

"You know…" she said. "You kind of look like me when I was in high school."

"Really?"

"Yeah." She reached out to take a carton of milk from me. "About the time I wanted to be a cheerleader." She giggled a bit.

"I don't think that will be happening," I said, with lowered eyebrows.

"Oh, I don't imagine so," she said. "But to be honest, I would support you if you did. And unlike Tom, I don't care what you do with your friends." She paused to think about her statement, and turned back to me with a raised eyebrow. "As long as it isn't drugs, drinking, or illegal."

I rolled my eyes. "I know…"

"I'm just saying I understand what happened today," she said. "Though I wouldn't go overboard with it like you did today."

"Or at least remember that Tom is coming to pick me up early," I said.

"That too."

"I just felt like I'd been keeping Tiffany from having fun this summer, so I agreed to let her do this. Then her sister got involved, and we did this whole fashion catalog shoot thing."

"Sounds like you all had fun."

"We did," I said. "Even though it cost me a summer in panties."

"Speaking of which," my mom said, "you better go put the ones in the sink up to dry."

"I almost forgot," I said as I started to exit the kitchen. Then I stopped and looked at my mom. "Do I really have to wear this all night?"

"Afraid so," she said. "I agreed to let Tom handle your punishment." She walked over to me. "But if you want my honest opinion." She put her hands on my shoulders and gave me a peck on the forehead. "Have fun with it, but don't show it."

"Thanks mom." I smiled and started to leave the room, but she stopped me.

"He wants you to put all your male underwear in this." My mother handed me a small white trash bag.

"I have to throw them away?"

"Heavens no!" she said. "He's just taking them away until you learn your lesson."

I sighed, and took the bag from her hand. Then I turned and pushed the kitchen door open. My mom went back to putting the rest of the groceries away, as I tromped down the hallway to my room. I opened the second drawer of my dresser, and then opened the white trash bag. It only took me a few seconds to gather up all my underwear and toss it in the bag. For some reason I thought maybe my stepfather had gone through this with his dad. I laughed at the thought of his six foot and two inch linebacker frame in a dress, as I tossed the bag down the hallway into his and mom's room.

No. My stepfather was a man's man. He constantly watched sports. Somehow he managed to have the knowledge to fix everything around the house. Apparently he could fix people too. He only dressed up for dress up occasions like funerals and the sort. Otherwise he'd be in some combination of grease-stained jeans and shirt. He smoked, thankfully outside, and drank, but I never saw him get drunk. On top of all of this, he tied it together with his burr haircut, which was about as out of style as his world view.

In the process of thinking about Tom, I'd made it into the bathroom. It only took me a few minutes to rinse my panties out in the sink. After doing so, I rinsed the sink out, and rolled up the remaining pairs in the brown towel. Then I picked up the towel and carried it off to the laundry room. When I walked into the laundry room, I twisted the towel gently, and then slapped it down on the countertop. I unrolled the towel, grabbed a few clothespins, and put the panties up next to my other pairs on the line. My mother walked in behind me.

"You sure picked out some cute ones," she said. "I figured you'd get all white, or some other solid color."

The thought never occurred to me to get plain white. "I just got the first package I saw that fit me."

"Wanted to get out of there as fast as possible?"

"Yeah," I said. "I still can't believe he made me do it."

"Tom's just a typical man," she said. "He gets an idea and there is no way to change his mind about it." She leaned against the dryer behind me. "I'm hoping you don't turn out like that in all honesty. I'd like to see you be more open-minded and mindful of other people's emotions."

"Tiffany and Kate liked my openness today," I admitted.

"You see?" My mother smiled. "Girls like that. A guy doesn't have to always be so macho and strut around like he's in charge."

"Maybe I'm too open." I looked at my panties hanging next to me. "I should've gotten all white," I said with a chuckle.

"Probably would've been better," my mother said with a half-hearted smile. Her face turned serious for a moment. "Do you like dressing as a girl?"

I thought about it for a moment before answering. I couldn't really say I liked dressing in girl's clothing, but I did have a lot of fun doing it today. This could be the fact that I was hanging around Tiffany way too much, and not spending enough time with the other boys. I decided to be honest with myself and my mother. She seemed like she could understand this better than Tom could.

"Honestly…" I looked at my mother. "I like it when Tiffany paints my nails."

"She's done it before?"

"For almost a year," I admitted. "And for a few months I've been keeping my toenails painted."

"I see," she said. "That would explain the sudden lack of being barefoot."

"Today was the first time she did my fingernails."

"Did you like that too?"

I looked at my hot pink fingernails. "I liked her painting them. I don't know if I'd like them painted all the time."

"Well you'll have two months to get that all sorted out in your head." She folded her arms beneath her breasts. "What about the dressing, and the makeup?"

"I loved the attention I got with the makeup," I said without hesitation. "Kate did it, and her and Tiffany were having so much fun…" My thoughts trailed off on me.

"But how did it make you feel?"

"I liked how I looked after," I said. "When I got home and looked in the mirror, I felt… I dunno…"

"Have you ever had thoughts of wanting to be a girl?"

"No!" I said, getting a bit confrontational and emphasizing it by shaking my head. "I just felt different. In a good way. But I don't want to be a girl."

"I just need to make sure," my mother said. "I thought we would have a little honest conversation before Tom got his hands all over it." She unfolded her arms. "What about the clothes?"

I looked down at the floor. "I like them."

"Because of how you look in them, or because of how they feel?"

"How they feel."

"I see," she said. "Well I'm not going to tell you to stop what you're doing. Honestly I don't see how you've done anything wrong. However, I would suggest you cool your jets around Tom, and at least pretend like it's a punishment." She stood up straight. "If he sees you enjoying it, he might try to get more involved." She flashed me a knowing smile. "Men always try to fix everything, but sometimes what they try to fix isn't broken."

"Thanks for understanding mom."

She held her arms open. "Promise me you'll talk to me about this if your feelings change."

"I will," I said with a smile.

I pushed forward from the counter and gave my mother a hug. She held me for a few moments before I broke the embrace. After a moment of her playing with my hair, she brushed past me toward the door. I looked at my panties hanging on the line. Perhaps this wouldn't be so bad after all. Tom had practically given me free reign to do what I'd been doing for months. Only now I wouldn't have to hide my painted nails. Though I still wasn't sure about doing it all in front of my other friends. At least maybe I could explain my feelings about it all better after the ordeal.

"Should've gotten white," I mumbled, as I turned the light off and walked out the door.

My mother and I finished cooking dinner by the time Tom and Justin got home. We all ate at the table without much talking. An air of tension about the day's events floated around us all. Justin, still wearing his silver down-to-the-knee shorts and gray shirt with the sleeves cut off from practice, talked a bit about football with Tom and mother. I swear he was turning into the typical jock, with nothing to talk about except sports and how he played them. Tom had rubbed off on him entirely too much. Every so often I got a glimpse of Justin and Tom looking at me with a bit of disgust. Mom didn't treat me any differently.

Justin didn't say a single word to me. He ate, got up, put his plate on the counter, and left the kitchen. After Justin was gone, my stepfather reevaluated my punishment. He set ground rules that I had to follow until school started. The first being that I was to wear panties day and night, regardless of where I went or what I did.

Secondly I had to keep my toenails painted all the time, and fingernails unless I was going to be around certain people. Mainly this meant all of Tom's friends, or going places with him. The downside to this rule was I had to wear nail polish around even my male friends. He lifted the restriction on colors, but told me nothing a guy would wear. This led to a five minute discussion on goth people and their black nail polish.

When I saw Tiffany next, Tom said I had to wear her clothes back over there. He also stated that if I was caught dressing again, he'd find new ways to get me to stop. Tom made it a point to emphasize that the entire punishment was designed to make me realize real men don't do girly things without consequences. To try and drive this point home, he asked my mother to lend me something to sleep in that night. She told him she would give me a night shirt to wear. Tom abruptly excused himself from the table afterwards.

"Do the dishes," he said, "then go to your room."

Mom waited until he grabbed a beer from the refrigerator and left the room. Then she patted my hand and gave me a wink. She stood, and gathered up the dishes. I relinquished mine. Truth be told, I wasn't all that hungry to begin with, and random Hamburger Helper with corn didn't suit me.

I still couldn't believe a simple game earlier in the day could turn into a major episode. All I wanted to do was have fun with my girlfriend. I started to think of Tiffany, hoping she wasn't beating herself up over all of this. Everything seemed fine in the grand scheme of things. My mother walked over to me. She put her hands on my shoulders and leaned down close to me.

"Put those clothes in the laundry room, and I'll wash them for you."

"Thank you," I mumbled. "If I ever get to see Tiffany again, I can give them back to her."

"Aren't you going to see her Friday for the fourth?"

"I assumed I was grounded," I said.

"He didn't say you were. I think you should call her tomorrow though, and explain the situation." She put her arms around me. "That will give her time if she needs to adjust her plans for…" She paused and looked at me. "Did you have a girl name?"

"We all decided on Bailey," I said, almost reluctant to divulge that information.

"Well that will give her time to include Bailey in her plans."

"I don't know if I'll be doing the Bailey thing anymore."

"Well you'll already be dressed as her," mom said.

"That's true…"

"I'll put some things in your room for you." She kissed the top of my head. "Wash the dishes. Then get some sleep. You had a long day."

"Goodnight mom," I said, still staring at the table.

"Night night sugar."

With those words, my mother left the room. I got up a few minutes later, walked to the sink, and quietly did the dishes. After drying them and putting them away, I exited the kitchen. I saw mom and Tom in the front room watching the evening news, so I figured it was close to eleven o'clock. Pissed at my stepfather, I didn't care to say goodnight to him, so I quietly went down the hall to my room.

I stepped into my room and shut the door behind me. As I leaned back against my door, I noticed some new additions to my belongings. First, there were several more bottles of nail polish on my dresser. There were a few bottles in shades of pink, one in true blue, one in laser red, and then another half bottle of dark red. Then I saw used bottles of top coat and base coat polishes. Next to all of that was a bottle of nail polish remover, cotton balls, files and pink toe separators. Apparently if I was going to be doing this, my mother was going to make sure I was doing it right.

I walked over to my bed and found a few more surprises. My two new pairs of white panties were missing. She probably planned to wash them with the ones I had on. The pair of dark pink panties I'd bought earlier were on my bed with a light pink shirt, which probably would've come down to the knees on me.

Next to the ensemble were a pair of pink ankle socks, about the same color as the shirt, and a few pairs of white ankle socks. Perhaps my mother got the wrong impression when I said I liked wearing girl's things. I didn't mean I wanted to wear them all the time. Now I feared I would soon have my own collection of feminine attire.

For the first time that night, I decided to go with my mom's advice. I was going to have fun, but not let Tom think I was having fun. I kicked off my borrowed ballet flats, gathered up the shirt and panties, and headed for the bathroom. After closing and locking the door, I stripped down to Tiffany's white cotton panties. Something in me wanted to wear them to sleep in, but some other part of me wanted to try the other pair. They were my own pair after all.

I painstakingly scrubbed the makeup off of my face. Then I took the barrettes out of my hair. Though I was pretty much back to boring Zachary, I still had the image of Bailey in my mind. I saw her as I gazed in the mirror. As I brushed my teeth, I saw Bailey brushing her teeth. Somewhere along the line I think I crossed a wire in my brain. Something seemed totally off to me. I figured it would go away with sleep, or perhaps I'd wake from a bad dream. Or was it a good dream?

I dropped Tiffany's panties to the floor and stepped out of them. Then I slowly replaced them with the pair of dark pink panties. They felt so light sliding up my legs. It gave me a sense of doing something so wrong, but it felt so right. As they settled over my bottom and hips, they fit perfectly. I instantly fell in love with the bikini cut, and they looked better than Tiffany's; which I found out later to be full briefs. I quickly put the sleep shirt on, which fell to just above my knees. Then I gathered up everything I discarded, including my sock boobs, and exited the room.

After dropping off Tiffany's clothes in the laundry room, I sneaked down the hallway to my bedroom. I closed the door, instantly wishing I had a lock, and walked over to my bed. As I looked at the socks on the bed, I decided to forgo them. For months I had been hiding my painted toenails, but tonight I didn't have to do that.

I put the pink socks on the table next to my bed, and the other pairs in my dresser. Part of me wanted to even paint my nails tonight, but I knew there would be plenty of time in the months ahead. I flipped off my light, and slipped into bed. Before long I couldn't fight the sleepiness, and dozed off.

I had a fitful sleep, and woke up pretty late in the morning. Tom had already left for work. He had a mindless job in the city cleaning semi trucks. I remember going down with my brother once, and helping him clean the shop. That is if you wanted to call it a shop. Most people would call it an abandoned warehouse big enough to drive semi trucks through. My brother and I got paid decent enough, so it wasn't terrible. Had Tom been the boss, I'm sure it would've been volunteer work.

Usually I was left with Justin to watch over me, but he had football practices until Wednesday. The house seemed unusually quiet. I slipped out from under the covers. The night before wasn't a dream. This became obvious when I looked down and saw my hot pink toenails. My fingernails were still hot pink, and I had on the pink sleep shirt my mother had given to me the night before.

I looked over to my clock. The time, displayed in bright red numbers, read nine twenty three. Next to the clock sat a pair of pink ankle socks. I again passed up putting the socks on. It would be nice to go barefoot for a while with painted toenails. Ever since Tiffany started painting them for me, I had been forced to hide them with socks.

The beige plush carpet beneath me felt familiar, yet strange. My feet sank into it when I stood up. I could feel it pushing up into the spaces between my toes. The individual fibers tickled the sides of my feet. It felt like I was walking on fuzzy pillows as I took the few steps to my door. My hand wrapped around the handle.

All of the lights were out upstairs. My mother was most likely gone too, as she seldom slept past eight o'clock. The few times she did, it would be on a weekend. I started to turn back into my room, when I caught a glimpse of something on my door. When I turned to look, I found a sheet of paper with a list of chores on it. I sighed, and pulled the list from the door.

I walked back into my room. The first item on the list was to empty the dishwasher. Apparently Tom had fixed it by himself last night. I carried the list over to my curtains. After taking a few minutes to throw my curtains back and let some light in, I realized mom's car was gone. She was probably hard at work by now at her office job across town. That meant I had about five hours to myself, until my brother came home. I held the list back up to look it over. It really wasn't all that bad.

"Dishes," I said to myself. "Mop the kitchen floor, clean bathroom mirror, and put the laundry away."

I wadded the list up and tossed it in my garbage can. All of the chores were things Tom considered jobs for women. Honestly, I never saw the difference if the things needed to be done. What the hell did he do while living on his own? Have his sister or girlfriend do them? The whole idea seemed stupid to me, and I didn't mind helping my mother out. Usually I was the only one who did. Not to mention the hall bathroom was mine for the most part.

My eyes wandered down to look at my attire. The pink shirt my mother loaned me to sleep in came down to almost my knees. There was maybe an inch or two from the bottom hem to the top of my knees. It seemed suitable to do chores in. I decided to keep it on. Not like anyone would see me in it. If someone came to the door, I didn't have to answer. I hurried out of my room toward the kitchen.

The dishes took very little time to put away. I guess Tom had only loaded it with a few to make sure it worked, and then ran it again with the morning dishes. My feet stuck to the linoleum floor in the area directly in front of the dishwasher. Now I realized why I had to mop the floor. Tom's lazy ass never cleaned up after himself.

My only dilemma of the day seemed to be what order I would do my chores. To most people this wouldn't seem like a big deal. However, after the ordeal I had yesterday, I was unsure if I could make decisions for my own good. I decided to leave the kitchen floor for last, and made my way to the bathroom. I had no idea how I was going to adjust my regular life for the next two months.

After using the facilities, I brought up the Windex from under the sink. I tried my hardest to clean the mirror without any streaks. As I finished the last few inches of the three foot, square-shaped mirror, I stared at my reflection in it. I missed the makeup from the night before. Everything I felt made me beautiful had been washed away. My lips fell into a pout, which started gears going somewhere in my brain.

I put the bottle of Windex down, and dropped the paper towel I'd been using in the toilet. Next to the sink were Tiffany's barrettes. I picked one up. Then I slid it in my hair on the side, and clipped it over my ear. It pulled my hair back, pulling my wavy strands away from my face, and allowing them to cascade down the side. I took another barrette and did the same on the other side.

For the next few minutes I stood at the mirror. I must have tried a hundred different combinations with the other two barrettes, but I couldn't get it to match the style Kate gave me. The two I had on each side looked cute. They gave me a sort of wavy bob cut look. I finally gave up on where to put the other two, and double clipped both sides. My eyes fell upon my lips in the mirror, which had somehow contorted into a disappointed half frown. Then I smiled.

I exited the bathroom, and quickly went down the hall to the master bedroom. After double checking to make sure Tom wasn't secretly hiding out in his room, I went in and made my way to my mom's dresser. On the top were random assortments of nail polish, lipstick and a ton of makeup. I scanned her lipsticks. Finally I picked a light pink shade.

Gleefully I ran back to the bathroom. I stood in front of the mirror. My hands trembled as I popped the cap from the lipstick. Within a few split seconds I had the waxy substance twisted up out of the tube, and had it inches from my lips. I thought of how Kate had shown me to put it on, and I went for it.

The lipstick slid across my bottom lip. It stuck and pulled gently as I took it back the other way. I moved it back and forth several times until it slid easily. My lips grew brighter pink with each pass. I carefully put it on my upper lip, making sure to even get it on the top points of the bow. Then I set the tube down and pushed my lips together. Perfect!

I pulled out a tissue from the box on the counter. I blotted. Then my fingers instantly wrapped around the tube of lipstick again. I reached up and spread another lighter coat on my lips. Afterwards I pushed my lips together and rocked them gently back and forth. When I opened my lips I loved what I saw. I puckered up like I could kiss myself. After tossing the tissue in the toilet and flushing it, I closed up mom's lipstick and headed to the laundry room.

The only things left on my list were mopping the floor and putting the laundry away. If I finished fast enough, I might have time to do my nails before Justin got home. My plans changed slightly when I entered the laundry room. Mom had washed Tiffany's clothes. Her shirt, skirt and socks all sat neatly on the dryer, while her panties and bra were hung up with my panties. All of those panties hanging up seemed so inviting. I stared at Tiffany's bra for a few minutes.

Before I knew it, I had pulled the pink sleep shirt off. I found myself unclipping Tiffany's bra from the wire, and slipping my arms through it. I fidgeted with the back until it was hooked firmly around my chest. Then I walked over to the dryer and picked up her socks, one at a time, and rolled them up. In a matter of moments I had my breasts back from the night before.

I gathered up the pink sleep shirt and pulled it back over my head. In a few seconds I was back at the bathroom mirror. I adjusted the bra and fake breasts until I felt they looked natural. Convinced that nobody could tell the difference, I exited the bathroom and headed back to the laundry room.

There really wasn't much laundry to speak of, as far as I could tell. Tom had a t-shirt, which mom had set aside with stain remover all over it. My things, along with Tiffany's clothes were there of course. Justin had a basket full of mostly gym shorts and cut-off t-shirts. I decided to leave his until I finished mopping. Mom seldom let her clothes stay in the laundry room. For the most part she put everyone's away, but the times she didn't, she almost always took care of her own.

Mom always had nice clothes. I mean they weren't fancy with designer labels or anything, but they were nice. She mostly wore knee length skirts and pretty blouses. Nothing over-the-top, but stuff you'd see a nicely dressed corporate secretary wearing. Usually she would alternate between black pantyhose and tan pantyhose. She seldom wore less than a three inch heel pair of shoes to work.

Justin and I shared looks, as my wardrobe consisted of probably fifty percent hand-me-downs. We both liked baggy jeans from Fall to Spring. I liked jean shorts in the summer, but he liked gym shorts. They had to be the baggy down-to-the-knee ones too. Justin wore a hat ninety percent of the time, where I maybe wore one nine percent of the time. The most common thing between us, was that we liked t-shirts and baggy hooded sweatshirts.

The one thing I never got handed down to me, was shoes. My feet were just too small to fit into his shoes. By the time I caught up to the size he used to wear, my mom would deem them "unsuitable" to wear. So I usually got a new pair of shoes to start the school year. I used the old ones to work or play in until I outgrew them. Then of course I had random situational shoes, but they were usually cheap ones from Wal-Mart.

As I thought about my clothes, I had subconsciously brought mine and Tiffany's back to my room. It took me a few minutes to decide how I wanted my panties folded. The little things like this confused the hell out of me. I decided to fold them like guys briefs. I'm sure I didn't panic some woman on the other side of the world who taught panty folding techniques. My mom had put Tiffany's skirt on one of her hangers with the clips on the bottom. So I hung it up in my closet along with her shirt.

After mopping the kitchen floor with one of those cheap sponge mops, I returned it to the laundry room, and grabbed the basket of Justin's clothes. I stood at the top of the stairs with the basket under one arm. The house seemed so quiet. Ever since I was four or five, I was scared to death of the basement. My fear seemed to alleviate itself over time, but it never went away completely. It was especially worse when I got stuck at home alone.

I started down the stairs. Thinking back on why the basement frightened me, I thought of a time when I had just turned six. My brother and I were running through the house and sword fighting. I think we were playing pirates or something. When we ran downstairs to the middle level, the one with the door to the outside, we heard a thud. We both turned to look down the rest of the stairs, and witnessed the garage door open and close. Then Justin's door opened and closed.

I stopped with my back to the front door and looked down at Justin's door. That episode in my past never wandered far from my memory. There were other times I heard sounds in Justin's room when he wasn't home. I always imagined it was my dead father coming back to the house for something. Maybe he didn't like Tom and wanted to kill him. That was okay with me, as long as I didn't get caught in the crossfire.

I smiled to myself. Then I continued down the stairs to my brother's room. The ceiling crackled a bit as I opened his door. My father had finished the rather large room right before he passed away. He started putting it together slowly when he found out my mom was pregnant with me. They wanted us both to be upstairs, but Justin apparently had thrown one tremendous fit about sharing rooms. So he got his own room downstairs. It was a converted living room, complete with fireplace and his own bathroom.

I snooped a bit as I put his laundry away. Part of me was a bit jealous that Justin got a cool room. The other side of me was relieved he got the creepy haunted room. I always liked fireplaces though. On several occasions I sat by the one upstairs, in the Winter, and read a book. Tom always made fun of me, saying it was a sissy thing to do. Then again, Tom could stand to pick up a book some time. All he ever did was watch television and bitch about what he saw on it.

I put a few clean towels in Justin's bathroom. Figuring I'd go the extra mile for mom, I gathered up his dirty towels and put them in the basket. This would at least save her a trip downstairs, even if I didn't decide to wash them for her. After taking one more quick look around Justin's room, I decided nothing in there interested me. I exited the room and closed the door behind me.

I think I was on maybe the fifth step up when the doorbell rang. Crap! If I had been anywhere else in the house, I could've ignored it. I froze, hoping whoever it was wouldn't lean over to look through the window on the side of the door. Crap again! They did.

On the other side of the door stood Nathan Riley. His lips turned up into a big smile when he saw me. He held up his hand to wave me to the door. Part of me didn't have the will to do this simple request. Some other part of me took over, and drove me up the stairs. I stood before the front door and took a deep breath.

I reached for the deadbolt on the door and unlocked it. Why the hell was I opening the door for him? I grabbed the handle and turned it. What the hell would I say to him? The door swung open. I placed the basket in front of me. Perhaps it would cause enough space between us. Perhaps it would give him the message that I'm busy. Perhaps he would say two words and go away!

"Hey!" Nathan said. "Bailey right?"

I thought for a split second. Thank goodness I put the bra on. "Yes… Nathan was it?"

"Yeah," he said. "I don't wanna bug you." He looked down at the basket. "You seem a little busy."

"Sort of," I lied.

"Cute feet."

"Thanks," I said, feeling a blush come on. A blush? Weird…

His eyes came back up to meet mine. "Well I was just wondering if Justin was home?"

"I'm afraid not," I said. "He's at practice until two or so."

"Oh…" Nathan looked puzzled. "He said we could go over some plays today." He looked up at me with his gorgeous brown eyes. "Maybe he meant next Tuesday…"

"Probably?" I glimpsed down at the basket. "He has practice tomorrow too." My eyes rose back up to his. "You want me to tell him you stopped by?"

"Nah," he said. "I can just come back next week."

"So I take it you play football with him?" Why the hell did I just drag the conversation out?

"Yeah." Nathan smiled. "Freshman camp isn't until the fourteenth, but I talked to him earlier. He said we could go over some of the offense."

"Oh, so you're a freshman?" Why did I care?

"Yeah…" He gave me another strange look. "I assumed you were older than me last night, but looking at you today…" His hand reached up to comb through his black hair. It was definitely black. "You look younger."

"I'm starting seventh grade this Fall," I said.

"Ah." He dropped his hand to his side. "Well I don't want to bore you with football talk."

"Oh, you're not boring me at all," I said. "Besides, I'm used to it with Justin. He goes on and on about it everyday." Why was I still talking?

"You stay here a lot?"

"Not a lot."

"Sorry. You just made it sound like you're here all the time."

For a few seconds I tried to conjure up some excuse as to why I was here. Several times I came up with blanks. The easy thing to do would be to lie. However, if Nathan would be hanging around Justin a lot, he would know in no time flat. Even a moron could connect the dots on this charade. After all, I had to wear nail polish for two months. How could I explain myself next Tuesday if Nathan saw me? The lying was eating at me anyway. I had to tell him before he found out.

"Can you keep a secret?"

"Well I don't know you that well," Nathan said, "but I can keep my mouth shut."

"My name really isn't Bailey," I said. "This is a sick and twisted punishment my stepfather is making me go through for the rest of the summer."

"I don't get it."

"He caught me messing around with my girlfriend yesterday." I looked around the street, and then back at Nathan. "We were goofing around and she had me dress up in those clothes you saw me in yesterday."

"Wait so you're a guy?" Nathan said, with raised eyebrows.

"Yes," I looked down at the basket full of towels. "My name is Zach. I'm Justin's younger brother. My stepfather is making me wear girl things for the rest of the summer." I was greeted with silence. So I looked up at Nathan with pleading eyes. "Please don't tell anyone."

"I…" Nathan scratched his head. "Who would I tell?"

"If this gets out…" I said. "I'll never live it down."

"So you have to dress like a girl?"

"So far it's only panties and painted nails," I said. "I'm hoping he doesn't add to it."

"Well, I understand that stepfather's can be pricks," Nathan said. "My own stepfather tries to overcompensate to prove he can handle the job of my dad. He's pretty much an asshole." He looked down at my feet, and scanned up my entire body. "But I don't get this. I mean, if you don't want someone to dress as a girl, why dress them as a girl for a punishment?"

"I don't get it either," I said. "I'm hoping he drops it after a week or two."

"Wait!" Nathan cocked his head to the left. "If it's just panties and nails… what's with the lipstick and tits?"

"I…" My mind drew a total blank.

"And you even did your hair." Nathan smiled. "You don't like it do you?"

"I..." Again a blank! Think dammit!

"Look," Nathan said. "It's okay if you do or don't. It really doesn't bother me one way or the other." He dropped his smile. "But it looks like you're in over your head."

"I am!" I pouted.

"To be honest," Nathan said, "you could go either way."

"Huh?"

"Just saying you make a cute girl. You have the features for it." He shrugged. "I never would've known the difference if you didn't tell me."

"Thanks… I think."

"Just be careful with whatever you do, okay?"

"Sure."

"I'll see you later," Nathan said. "Kinda curious as to whether I'll see Zach or Bailey, but I'll see you regardless."

"Thanks for being cool with it."

"Eh, I know how it is." He turned to walk down the steps. Then he stopped, and held his hand up as he did so. "You still have cute feet."

I was definitely blushing now. I could feel the heat. "Thanks." I smiled at him as I shook my head.

Nathan started down the stairs again. "Take care," he said behind him.

"You too."

I leaned back against the door as I closed it behind me. For the third time in two days, I had this weird and unfamiliar feeling inside. Once it had happened when Kate put makeup on me. Twice it had happened after talking to Nathan. Was I giddy? Did I like being Bailey? My thoughts wandered to the moment Bailey had been "born" in Tiffany's bedroom. I was giddy then! I'd been giddy for the past twenty four hours!

I mindlessly locked the front door, and carried myself up the stairs. Without even looking at where I put it, I dropped the basket in the laundry room. I had to think about this. My "cute" feet carried me into my room, and there I sat on my bed. After a few minutes of recalling the past two days, I started to weigh facts.

I put my hands on my bare knees and put my feet out. My eyes danced back and forth between my toenails and my fingernails. The hot pink left an imprint in my mind when I shut my eyes. I opened them. In my own head I finally reached a conclusion on my nails. I liked them painted. The fact wasn't that I liked Tiffany to paint them, but that I actually liked having them painted.

My hands rubbed over my knees. I barely had any peach fuzz on my legs. While I loved seeing girls with smooth and hairless legs, I still wanted hair on mine. I actually looked forward to it, like it was a right of passage. So that little fact told me I still wanted to have a guy's body, with hair and all. It felt like the natural thing.

Muscle? I didn't have much to speak of, but I knew I wanted some. Not like my brother's, as he was starting to look like those big bulky athletes on television, but at least enough to show I was a boy. Maybe I could start lifting weights? No, that wasn't like me. So far I had two facts weighing on the male side of my brain.

The female side fought back. I liked makeup. Maybe part of it was because it made me look like another person yesterday. Some other part of me liked the way it felt. Combined with the way I felt with it on, and the way I looked, I came to the ultimate conclusion that I liked wearing it. Even if it was only lipstick, it still appealed to me.

The issue of clothing is were I hit a double-edged sword. When I wore my own clothes, I liked baggy stuff. It felt comfortable. When I wore Tiffany's clothes, I liked her tights and form-fitting shirts. That felt comfortable as well, but a different kind of comfortable. I would never wear tight clothing as a guy, because even I thought that looked sissy. I had mixed feelings on the issue. After a few minutes of thinking, I decided I liked both. Maybe I was becoming a guy that liked to crossdress occasionally?

However, I couldn't do that. Tom would either kill me, or utterly humiliate me. I'd probably have to dress as a punishment, which would mean when he wanted me to do it. It wouldn't be fun then, and I wouldn't feel comfortable. I started to wonder if Tiffany would let me dress at her place. She would at least have fun along with me. Then I remembered I had to call her. I picked up the phone.


 
 
To Be Continued...
 

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The Summer of Bailey: Part 2

Glad she found a friend in Nathan.

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

So I'm guessing that Nathan

So I'm guessing that Nathan just might come to Bailey's rescue at some point in time, such as being against her brother if he gets "stupid" as brother's are known to do on occasions. My feelings are that it is way past time for Mom to step up to the plate and start protecting Zach/Bailey, as she definitely seems to have abrogated her role to Tom. Tom is a huge jerk in capital letters and Tom needs to grow up himself. He is, by his actions, speech and so-called parenting skills simply turning Justin into a clone and definitely turning Zach against him.

It'd Serve His Father Right...

...if that paper towel Zach threw down the toilet backed the whole thing up. (Though I'm not sure I'd want to read about the details.)

Anyway, good job describing Zach's confusion. There are still several ways this could come out, and it should be interesting seeing which one gets chosen.

Eric

Reaction to Nathan

His reaction to Nathan says a lot about what side of the gender
fence this boy is at.

It seems to me that Tom is the kind of man, like most men

that if they don't get their way, or somebody doesn't act the way they do, they not only get angry, they get violent. I am supposing that Tom is going to do just that. Of course, the mother only seems to have enough guts to take a stand when she and Zach are alone, because she gave in way too easily to Tom to let Tom handle Zach's punishment. That tells me that the mother is afraid of Tom. Dying to see the next chapter.

"With confidence and forbearance, we will have the strength to move forward."

Love & hugs,
Barbara

"If I have to be this girl in me, Then I have the right to be."

"With confidence and forbearance, we will have the strength to move forward."

Love & hugs,
Barbara

"If I have to be this girl in me, Then I have the right to be."

Bailey/Zach

Yoy have done a neat job of moving the story along as well as how things play on Zach's mind.
I look forward to reading more.

JessieC

Jessica E. Connors

Jessica Connors

Nathan said it all

Jamie Lee's picture

Tom makes a box of rocks look intelligent. Did the guy ever go to school? College even? If he had, surely he would have learned even the head of a pin amount of psychology.

Zack resisted Tiffany painting his toenails for some time. He finally relented and kept it a secret for over a year. Now, had Zack not ever wanted his toenails painted, he never would have relented. Same goes with his fingernails, the makeup, and clothes. What he allowed has him confused and happy at the same time.

So, the macho knuckle dragger thinks kitchen work is only for woman. That cleaning the house is only for woman. That the way to break Zack from further dressing in girls clothing is to dress him in clothing no one will see. And have his nails painted. Nathan is so right, someone who enjoys something shouldn't be punished by doing that which he likes. But who ever said knuckle dragging AH pigs were intelligent?

Zack's mom is the intelligent adult in the house. As she said, Tom is a typical man who has his mind set on how to punish Zack. It's made up and won't be changed, unlike a diaper, which Tom needs. By stepping back and letting Tom have his way, she's letting the outcome prove Tom wrong.

Mom is actually in Zack's corner, or she wouldn't have put all those items in Zack's room. Or chide him to act like he's being punished. Mom knows Bailey is in the house, it's just a matter of letting her exist.

Others have feelings too.

I am re-reading this

Angharad's picture

and enjoying it all over again.

Angharad