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Crossdress Day

by Robin Diaz

Chapter One

 

I sat at the table eating dinner and listening to my parents talk about their day. I was waiting for the proper opening to ask my question. A question worried me to ask. I was not sure how my parents would react. I was not sure how I wanted them to react. Part of me wanted them to say no, to provide me with an excuse to my friends.

Mom turned to me, "How was your day?"

"What," I paused. I did not have the courage to ask "Ah, fine."

"What's wrong?" Mom always knew when I was holding something back.

"Nothing," I did not know how to ask, "Why?"

I think she knew I had something to ask. "Something is bothering you," She became the concerned, supportive parent. "Tell me."

I looked at her thoughtfully. "It's kind of weird". I considered not asking. I could not look at her, so I looked down at my food, "Tomorrow is cross dress day."

"What the hell is that?" Dad snapped, cutting me off. He set his utensils down giving me his full attention. He knew what I was talking about; however, he wanted to hear it from me.

I looked up from my plate, "Girls dress like boys and boys dress like girls." I said it hesitatingly, and then blurted out, "It's a school requirement." That was a small lie. Students were not required, but I made a pact with my best friends Kevin and Tim. I couldn't back down.

"You mean you're going to wear a God damn dress to school." Dad was not angry with me. He was angry over the concept. Dad though school was too easy, actually his term was woosy.

"John, don't yell at him," Mom raised her voice. Dad looked at her. "And don't curse at him." Dad paused to calm down. Mom in her way diffused the situation, "It's not his idea. It's a school activity."

Dad looked back at me. He wasn't happy but he knew Mom was right, "I still think it's a bullshit activity."

"John, I'm sure Lin will survive. You don't need to be making more out of it then its worth. And I asked you not to curse." I was surprised she did not slap his hand.

Mom looked back at me, "You said tomorrow?"

I nodded yes and then looked at her. I knew what she was thinking. I knew what she was going to ask. "When did you find out?" She had that 'you knew about this before today, yet you waited to tell me' tone. She tightened her lips and gave them a slight twist. She was annoyed.

I was hesitant to tell her, "Last week" Then I shrugged my shoulders, "I forgot".

It had been my plan to tell them the last minute. I did not want to give either of them time to talk to other parents. Dad would never agree if he did not believe it was mandatory. I decided if they discovered after the fact, I would just lie and say I did not know.

Mom shook her head in disgust. "How am I going to get you ready in one night?"

"Maybe, I can stay home sick?" Telling them that was a gamble, but I did not want Dad to think I was a sissy.

"There you go," Dad pointed his fork at me but looked at Mom, "Now the boy is using his head."

Mom sat thinking about my statement. I thought that maybe I should have kept silent. "I don't think we're going to be graded." The lies were just flowing out of me.

"You're not going to miss a day at school and ruin your perfect attendance, nor are you risking your straight A's. You are not going to spoil your academic career." I could always count on Mom to keep me on the straight and narrow.

"So he misses a day," Dad said with a mouth full of food.

Mom shook her head. I did not know if it was because she did not believe what Dad said, or that he said it with a mouth full of food. She straightened her shoulders and stated, "He's going. He will survive".

Mom had a way of ending conversations. Dad rolled his eyes. He did not agree with her but he was not going to argue. I could always count on Dad to keep the peace.

"After dinner get right on your homework. I'll take you shopping after I clear the table," Mom still had that, I am mad at you tone.

"Shopping?" I asked, truly not thinking.

"Do you have a dress hanging in your closet?" She was not asking. She was telling me to wake up and think. I shook my head no. That ended that conversation.

After dinner, Mom cleaned up after us. Dad opened a beer and went into the family room to watch the sports news. I went into the study to work on my homework. I had trouble concentrating on the math problems. I kept wondering about what Mom meant buy shopping. Where the clothes would come from was an oversight on my part. I wondered if she expected me to try them on in the store. I became anxious; maybe Dad was right. Maybe I should be sick; more as if I think I was going to be sick.

"Ok, are you ready to go?" Mom stood at the door with her car keys in hand.

"I'm not done with my homework," I realized I had not gotten very far with my homework.

"How much more time do you need?" Again, I could see she was not happy with my procrastination.

"I don't know. I got a lot more then usual, maybe a half-hour, maybe longer." Another lie, but I did not want her to know that I was not concentrating on my work; that I had spent the last half-hour thinking about tomorrow.

"We can't wait. The stores will close in a couple hours. You can finish it when we get home." Mom walked away. That was her way of telling me to move.

Mom made my ride to the mall as miserable as possible. She lectured me on how I needed to be responsible. She told me how I was becoming a young man. I was not a child anymore. I apologized and agreed to what ever she said. She continued the lecture across the parking lot. Just before I opened the door for her, I barked out at her, "Mom! I get it, Ok, can you give it a rest."

She glared at me, "You're not too old that I can't pull your britches down and spank your bottom."

I opened the door holding my head down, "Sorry."

She let me stand there a second holding the door. "Thank You" she then walked past me.

I followed her in. The mall was near empty; only a few people were shopping. I looked around. What we were about to do- hit me. Mom was taking me shopping for a dress. I became scared. My stomach cramped. I no longer cared about a silly pact with friends, "Mom I don't feel good. Maybe I should stay home sick tomorrow."

She looked at me. I was expecting her to yell at me, but she smiled. I guess she saw my discomfort, "Don't worry, this will be fun." I did not understand her attitude.

"Do you know what you want?" She asked me.

"I hadn't given it a thought." I told her another lie, but I was not about to tell her that her son has been thinking about wearing a mini-skirt.

"I know a store that carries some nice lines." Mom had a thing about buying quality. She did not waste money on cheap clothes, even if you were only going to wear it once.

We entered an upscale women's store. It had a highly polished wood floor. The place was so clean and polished all the glass and chrome sparkled. A sales girl walked up to us. Her high heals clicking on the wood floor. She looked college age. She wore black heals, black stockings, a pleated black skirt, a shear white blouse and a tiny black vest. I could see her bra through her blouse.

She smiled, "May I help you find what you are looking for?"

I knew mom would like her, "Yes. I am looking for a dress for my son."

I looked up from the girl's breasts. My face must have been fire engine red, because I could feel the heat. I could not believe Mom just told this beautiful girl that the dress was for me.

The girl did not blink, "Is the dress for a special occasion or for every day?"

Mom put her hand on my shoulder, "He needs it for school tomorrow."

I wanted to die. Mom could have explained why. She made it sound like I wear dresses to school all the time. I went to explain but they kept talking.

"You are in luck. We are having a fantastic sale; buy one get one free." The sales girl walked to the display. "It is our fall line, but since you need the dress for tomorrow he will still be in style." The sales girl stopped in front of a circular rack stuffed with dresses. She looked at me, "What is your dress size?"

I stood there with a blank look. I thought - how the hell should, I know. I looked at mom.

"He should be an eight, maybe a ten." Mom said.

The girl moved to the dresses in that size. "Do you know what you want?" She asked looking at me.

Again, I had a blank look. I could not tell if the girl was stupid or teasing me. Then I heard Mom. "Lin why don't you look through the rack and pick out what you want. I'll be right back." She turned to the sales girl and whispered something. I assumed she was asking where the toilet was located. The sales girl pointed and Mom walked towards the back of the store. I stood there, embarrassed. I wanted to explain why I was getting a dress, but was too intimidated by the girl to speak.

She smiled. "Do you need me to help you?" She did not wait for a response. She started looking through the rack. She pulled out a kaki bib-jumper. She then held it in front of her. "This is great. You can wear a blue blouse with it now. In the winter, you can wear it with a red or green turtleneck. And in the spring it looks great with a pink or yellow top." She handed me the dress, "What do you think?"

"What ever, I only need it for tomorrow." As I spoke, I relaxed. I told her the same lie I told my parents. "It's a mandatory school activity, cross-dress day." I felt better after defending my manhood.

"Cross dress day?" I heard her say cross dress day but I felt like she said 'yeah right'. She held the jumper up to me. "I think you will look cute in this." I did not like how she said cute. She pulled the dress away, "I also have it in denim."

"No denim." I heard Mom tell her.

I saw mom was caring some undergarment, lingerie. "Are these also two for one?" Mom asked.

"Yes" The sales girl responded. I heard a slight tease in her tone.

"We'll take these." She handed the yellow set to the girl. "He will need the other set to wear while he tries on dresses." She went to hand me the pink set. I did not take the lingerie from her. I turned my back to the sales girl. In a near whisper I whined, "Mom!" She could see my embarrassment. "Oh, quit your whining. I'm sure," Mom glanced at the sale girl's nametag. "Cynthia has waited on plenty of boys wanting a dress." She then pushed the pink lingerie in my chest.

I did not like how mom stated, 'boys wanting a dress'. I was not like that. However, I took the lingerie from her. What else could I do? I had never felt lingerie before. I was surprised at how soft the fabric was. Getting a small amount of pleasure from feeling the lingerie embarrassed me further. Dejected, I turned back to Cynthia with my head down.

"Just so you know most girls his age are wearing an 'A' or 'B' cup." Cynthia told Mom.

"I think the training bra will do for his first bra." Mom then looked at me, "Unless, Lin would you like to have a bigger bust line?"

From Mom's tone, I realized what she was doing. She was making me suffer; pay in embarrassment for my procrastination and rebellious attitude. I thought of giving her a heart-felt apology. Maybe then, she would back off. Instead, I moved closer to her and shook my head no - while still staring at the floor. No boy could hold his head up through that kind of humiliation.

"Is that the dress you want?" Mom asked.

I felt like crying. What have I agreed to? I wanted to go home. I shrugged my shoulders.

Mom told Cynthia, "I guess this will do". I could hear mom was again annoyed with me. "You better go try your dress on, we don't have all night."

"I'll carry this for you." Cynthia said taking the dress to the changing room. I looked up at mom. She motioned for me to go. I started to follow Cynthia. I looked back at Mom. It was a weak attempt to plead, to say I changed my mind.

"Don't forget to put your bra on." Mom said in a loud voice. I turned back to Cynthia and kept walking with my head down.

Once in the changing room, I took off my T-shirt. The bra did not have any clasp. I determined that you slipped it on over your head; just like a T-shirt. It had a snug fit. I looked at myself in the mirror. Seeing me wearing a pink bra was an odd sight. I took my sneakers off, and then undressed. I hesitated, holding the panties, wondering. I should have never agreed to wearing girls clothes. I should have told Kevin to forget it.

"Do you need a hand?" Mom was standing outside the door.

"I'm fine"

"If you need me I'll be right here."

I pulled my underpants off and slipped the pink panties on. It was an odd feeling wearing the panties. It was nothing like the boxers I wore. They were soft and hugged my bottom. Again, I looked at my image in the mirror. It was strange and exciting seeing my body in a pink bra and panty set. I took the jumper off the hanger and slipped it on. I tried to zip the back but could not reach the zipper.

"Mom can you help me?" I opened the door.

Mom did not attempt to zip me, "Lin you can't walk around with just a bra on, put your T-shirt back on."

I bent over and picked my T-shirt up off the floor.

"Oh, I see you decided to wear your panties. Remember! Don't bend over like that while wearing a dress; you're showing your panties to the world. Bend at the knees."

I quickly straightened. More because of her tone, that something was wrong, then the idea that my panties were showing. I tried to put my T-shirt on while holding the jumper up. Mom thought I was comical; she started to giggle. In frustration, I let the jumper fall to the floor and slipped my T-shirt on. Mom laughed while I slipped the jumper back on. She then pulled the zipper up. Wearing the jumper was a different feeling. It was almost as if I was naked. I could feel the panty and bra on me, but the air flowed through the jumper.

When I turned and faced her, she shook her head, "I don't like this on you. It just hangs." She tugged at the sides, "This is not at all flattering."

Mom's words were an objective statement, however the way she said them, they sounded like a personal criticisms. I turned toward the mirror, "I don't know, I think it looks good." I did not really care about the jumper. I just wanted to disagree with her and end the shopping experience.

"You're not wearing that to school." She laid down the law.

I turned around to argue. However, before I could, I saw Kevin. He saw me, "Hey Lin. Hi Mrs. Troy." Kevin stopped outside our dressing room. He was holding the same jumper, but in pink. He was holding a cream-colored top with pink trim.

"Hi," I was shocked and surprised to see him.

Mom turned around, "Hi Kevin."

"Kevin who are you talking to?" Mrs. Harris asked. "We don't have much time." I could hear her walking towards Kevin as she spoke.

"Lin and Mrs. Troy," Kevin stated.

Kevin and I have been best friends since kindergarten. Our families have been friends for years. Mrs. Harris was our Cub Scout Den leader. My dad coached us in youth basketball. I never understood why our mom's were friends. Mom is always serious and thinking about our future. Mrs. Harris is easy going and only thinks about the moment. Mom likes things neat and organized. Mrs. Harris has a relaxed attitude about cleaning. However, when the two get together, they talk for hours.

Mrs. Harris appeared at the door, "Hi". She appeared truly glad to see us.

"Hi," Mom was happy for the company.

"So mine wasn't the only one who waited to the last minute," Mrs. Harris stated rolling her eyes. That look, that states, what are we going to do with these boys.

"I know. I could have bopped Lin," Mom added.

"Oh, I see Lin is going to wear a bra." My reaction to her words was to cover my chest with my arms. Both Mom and Mrs. Harris chuckled.

"Kevin sweetie would you like a bra?"

The situation was embarrassing for me, but at least Mom did not call me sweetie.

"And panty" Mom added. I could tell she was enjoying my humiliation. Both laughed. Kevin and I looked down at the floor. Moms have a knack for embarrassing their sons.

"Where did you get the bra?" Mrs. Harris asked.

"There is a table near the back." Mom motioned. "They are on sale, two for one."

"Kevin sweetie, is there a special color you would like?"

"Pink is nice," he didn't hesitate.

I looked to see their reaction. I do not think they were expecting an answer. Neither mom laughed. Mrs. Harris looked at Mom bewildered. She then shrugged her shoulders. I looked at Kevin, thinking are you serious? He looked at me with a devious smile. I thought way to go Kevin that shut them up. Mrs. Harris went to pick out Kevin's lingerie.

Mom turned to me. "Get out of that, we'll have to find something else." Mom then stepped out of the changing room. Before shutting the door, she told me; "Leave your bra and panty on."

I took the jumper off and put my pants and T-shirt on. My clothes felt different. They felt bigger and baggy. I left my shoes off. I stepped out of the changing room and looked around. I was self-conscious. Mom had walked away. I slowly walked to the entrance of the changing room area and looked for her. I did not want to step out into the open.

"Lin, here" Mom waved to me.

I walked to the rack; kind of using the jumper to hide behind. Cynthia came up to me. "I'll take that for you" I handed her the jumper. She stood there. Mom was looking at skirts. Cynthia looked at me and smiled. Then she gave her attention to mom. "That is a great skirt," she told Mom, "And very popular with the girls his age."

Mom pulled the grey skirt from the rack. It had a flat panel with a pleated skirt. It also had a faint red and light grey diamond pattern stitched into it. Like an argyle pattern. Cynthia was right; that was a popular skirt with the girls in school. Mom held it up to my waist.

"We have an off red t-top that goes great with that," Cynthia told Mom. She then stepped away and returned with the top.

"Oh, that is pretty," Mom, stated. She then held the skirt and top up to me, "I like this. What do you think Lin?"

"We have a wide red belt with a matching purse that also goes very well with the outfit." Cynthia was selling. I wanted to stop her. The clothes were for one day, but I could see Mom was in her element. She was buying clothes. I don't think anything gave Mom pleasure like shopping for clothes.

"Let me see," Mom told Cynthia. She then looked at me again. "What do you think Lin? Is this not pretty? I just love the top". She pulled the outfit away and held it to her, so I could look at it.

"It looks fine" I wasn't sure what to say. I watched Mrs. Harris walk into the changing rooms. I wished Kevin were with me. Participating in cross-dressing day was his idea.

`"What do you think?" Cynthia returned with the purse and belt. "Now these aren't two for one, but the hose are," Cynthia also had a pair of red pantyhose that matched the top.

"Lets try this on" Mom said, ushering me along. She was excited about the outfit.

As we walked into the changing room, I saw Kevin stepping out. Seeing him in the pink jumper lifted my spirits. Mrs. Harris was saying the same thing to Kevin that Mom said to me. Mom followed me into my little room.

"What are you doing!"

"It will go quicker if I help you," She stood holding all the clothes.

"Mom I'm not changing in front of you"

"Don't be a baby," She was trying to push her will over me. I was not going to let her. We stood looking at each other, both being stubborn.

"I'll close my eyes while you put your skirt on," She conceded.

"Ok," I compromised.

I took my T-shirt off and pulled the top on. Like the bra, it was very soft. Mom had her eyes closed and her head tilted up. I dropped my pants. I took the skirt from her but could not figure out how to take it off the hanger. It was clipped on.

"Is it ok to open my eyes?" I knew Mom was wondering what was taking so long.

"I can't get the skirt off the hanger," As soon as I started talking she looked down at me. She took the skirt out of my hand. Before I could protest, she had the skirt free and was handing it back to me. She made me feel like a helpless little boy.

"First sit down and put your pantyhose on." Mom handed me the pantyhose, and took the skirt back. I started to slip them on as if they were pants. Mom shook her head, "Stop, stop, you will ruin them." She took the stockings out of my hand. "You scrunch them up, like so." She showed me. "Then you stick your foot in and slowly pull them up. Almost like unrolling them up your leg."

I did as she instructed. I started telling myself it is a lot easier being a boy. As I got near the top, I stood and pulled them on. Mom gave me the skirt back. I stepped into the skirt. She hung the empty hangers on the hook. The skirt was not as soft as the other fabrics but it slid over the pantyhose. Mom could see that I was not sure how to wear the skirt.

"Let me help. Turn around." She motioned with her finger.

I did as she asked. She turned the skirt so the zipper was in the back. She held the skirt and slowly pulled the zipper up. "Suck your stomach in" I did as she requested. The skirt was tight around my stomach. I looked at my reflection. The top did not fit into the skirt. There was about an inch gap that exposed my stomach. I now understood mom's earlier statement about the jumper not being flattering. The skirt had a slight flare. I looked like a young girl. I smiled. Which I quickly stopped before mom would see. I was surprised that looking like a girl made me fell better.

"Here put your belt on." Mom handed me the belt. I stood looking down holding the belt. A little dumbfounded, the skirt did not have loops.

Mom saw me searching for the loops. She took the belt from me and wrapped it around me. She started to buckle it. Mom instructed me, "You don't want to buckle it to tight. You need to let it rest at a slight angle." She adjusted the belt, "There that looks better." She tugged at the bottom of the top. The red belt pulled out the red diamond pattern in the skirt.

Mom then handed me the purse. It was a small, simple red purse. I held it in my hand. She took it from me and hung it on my shoulder, "That is how you carry your purse." Mom turned me around. She picked at the clothes, adjusting the alignment. She again tugged at the bottom of the top. I did not think she liked my stomach showing.

"What do you think?" She put her hands on my shoulder. "You look pretty."

I did not say a word. I admitted to myself that I looked like a girl. I was not going to tell that to mom. Mainly because I did not want her to think, her son was weird.

Mom started to fuss with my hair, "The make-up is easy to solve." I had wavy brown hair, which I combed to the side. She played with my hair some more, "I'm not sure what I can do with your hair."

"Mom, my hair is fine," I pushed her hand away.

"I'll deal with it later," She had to make one final adjustment. She always had to have the last word. "Let's pick out your second outfit." She said opening the door. "It will have to go with your purse and belt; I'm not buying you two." She told me that as if I wanted her to buy me two.

"I don't need a second outfit this one is fine" I stood gesturing with my hands.

"I'm glad you like your skirt." She tugged at the top. It was not going to stay down; she did not understand that the small gap was the fashion. "But the second one is free, why not get it? You never know what will happen," Mom and her words of wisdom. I knew better then to argue.

I followed her out. The feeling of dread came over me as we neared the exit. I looked for Kevin. He was with his mom looking at dresses. He was wearing the jumper and top. Seeing the two of them was watching a mother and daughter shopping. I wondered if I appeared as a daughter. Mom walked up to Mrs. Harris and Kevin.

"That looks a lot better on you then it did on Lin," Mom told Kevin.

"Thanks" was Kevin's response. "Mom doesn't like it."

I wondered about Kevin. The kid was getting weird. Then I heard Mrs. Harris, "Oh my, Lin you look very pretty."

I was raised to be polite. I smiled, "Thanks."

"See Kevin you would look much prettier in a skirt." Mrs. Harris told him. She pulled a denim mini skirt from the rack. The mini skirt is what most girls wore to school. I knew Mom would never let me wear denim, or a mini skirt. Kevin looked at me and grinned. I wanted to say don't be grinning at me dude, this is all your fault. He tells me, "You do look good in that."

I was trying to figure out if he meant it or was messing with my head. I told myself he was being a smart ass. I could play head games. In as sweet a voice I could make, I told him, "You look pretty in pink."

"I think pink is his color" Mrs. Harris took a pink top from the other rack.

Then I heard Cynthia behind me. "I see the boys are taking to their new clothes. Let me show you my idea for a second outfit. With the correct combination Lin can mix and match; turning two outfits into four." Her words resonated in my head. I wasn't taking to the clothes. I was being an ass to my friend. She needed to be set straight, but Mom spoke before I could, "Yes I like that; show me what you're thinking."

I could see the shopping gleam in Mom's eye. She followed Cynthia to the rack. Cynthia told her what she was thinking. I followed. My anger towards Kevin returned. I was annoyed with Cynthia for thinking I was enjoying myself. I was frustrated with mom for not listening to me. Moreover, I was aggravated with my accepting attitude. I should have been throwing a fit, being dragged, not following along. I thought to myself, 'resistance is futile; prepare to be assimilated'. Then I thought; I watch way too much television.

Cynthia pulled out a double-layered charcoal grey skirt. "This is the skirt I had in mind." She held the skirt in front of the skirt I was wearing. "Hold this" she told me handing me the skirt. "And this is the top" She pulled out a black camisole. "I just love this top," she told Mom. She then held it in front of me so Mom could see the top and skirt together.

"That is lovely, but a little more revealing then I like." Mom told Cynthia. "I'm not thrilled with the way his tummy shows now." Mom tugged at my top.

I didn't care about the clothes. Nevertheless, I did agree with Mom. I did not like how my stomach showed. I looked for Kevin. I wanted to shout at him, 'asshole'. He was with his mom over by the denim skirts. Mrs. Harris was holding different skirts and tops up to him. They were talking, laughing and joking around. Again, I felt like I was watching a mother and her daughter shopping.

I heard Cynthia tell mom, "I understand, but that is all the rage with the young girls." Cynthia did not want to lose a sale.

"I think it is inappropriate for a thirteen year old girl to show her midriff." Mom stated.

"You're not the first mother to have that concern. The way to solve that problem is with an outer layer, a blouse." Cynthia moved to another rack as she spoke. She showed mom a white blouse. "This will also help her stay a little warmer."

Mom took the blouse off the hanger and handed it to me. "Lin put this on." I took the blouse. I realized I could not put the blouse on with the purse hanging from my shoulder. I handed mom my purse, and then slipped the blouse on. It looked like the white shirts I wore to church, except the buttons were backwards and the fabric was soft.

"Yes that is much better," Mom handed me the purse back.

"Why don't you try these on while I go help Kevin with his selection," Cynthia stated.

"I don't need to," I blurted out.

"Yes you do," Mom took the clothes from Cynthia.

We went back to the changing room. Cynthia went to increase her sales for the night. Mom had me change the skirt. The second skirt felt different. It was softer and lighter. The skirt had an inner liner that felt slick against the pantyhose and caressed my thighs when I moved.

After Mom made her adjustments, she had me look in the mirror. "What do you think?" She asked without waiting for a response, "I think this is very pretty on you."

I liked the feel of the skirt I had on, but preferred the look of the pleated skirt. I was not going to tell her, I shrugged my shoulder, "Whatever."

"You know you can be the horse's ass at times."

"What?"

She shrugged her shoulders, mocking me, "Whatever." She looked at me through the mirror. "You need to learn to loosen up. I believe this activity is supposed to teach you more about life then just wearing a skirt."

I could not believe what I was hearing; I need to loosen up! She's the one who is uptight. She is the one who cannot take a joke. I am happy go lucky compared to her.

"Do you think you look pretty?" she asked again.

The easiest way to get out of the conversation was to tell her what she wanted to hear. "Yes." She raised her eyebrows. I tried to sound sincere without making myself sound like a sissy. I then looked around to see if anyone could hear me, "Yes I look pretty."

Mom smiled and gave a loving squeeze to my shoulders, "Go ahead and put your other top on."

She held the blouse after I took it off. Then I pulled the red top off. I had to fix my bra, pull it back down, before putting the black top on. The black top looked terrible over the wide straps of the training bra.

I could tell from the face Mom made she was not happy, "Oh, that won't do at all."

I was glad she said that. I was not keen on the idea of the entire school knowing that I was wearing a bra. I started to take the top off when Mom stopped me. She told me to wait, and then left the room. A minute later, I heard a knock. It was Kevin. I opened the door. He was wearing a denim mini skirt with pink camisole and a slightly darker pink blouse.

I was amazed at his appearance. He was looking like a girl, "You done?" I asked.

"Almost, I didn't think our moms would be so enthused about shopping for a dress." He told me.

I shook my head in disbelief, "Tell me about it."

"Oh, you do look pretty," he winked at me and smiled.

He had heard me, "Fuck You."

"Kevin sweetie what do you think of this top?" Mrs. Harris asked.

Kevin rolled his eyes before turning. He looked at what his mother was holding and smiled, "I like that." I thought his response and tone was a little too quick and a little too sincere. Kevin stood with his hands on his hips just like a girl. Mrs. Harris stepped up to Kevin.

"Lin that," she hesitated, "that is beautiful skirt."

Mom came back, "We're in luck. I was able to trade the yellow bra and panty for a black set." Mom showed Mrs. Harris the black bra.

Mrs. Harris looked at Mom. "Oh my" By the way she was looking at Mom and her tone, I thought her statement was actually a question.

"Yes," Mom Said. "Don't you think he will look darling?"

The two women grinned. "Kevin I'll be right back," Mrs. Harris stated.

"Lin you better put your other top back on." Mom told me as she gathered up my clothes. I wondered what was going on.

Cynthia came to the door just as I was pulling the red top on, "So, how are we doing?"

"We'll take these. However, I'm not sure about the belt and purse. Do you have them in black?"

"Yes, I'll get them for you," She was being very helpful. Cynthia returned shortly with a black belt and purse. Mom had me change my skirt before putting the belt on.

"I like the black better. What do you think Lin?"

"The black is fine," I felt it necessary to elaborate for my own good. "I like how the black goes with the grey skirt better. They both go with this skirt." I could see Mom was delighted with my response.

Mom opened the door and asked Cynthia, "Is it ok if he wears the outfit out? We still need to buy shoes, nail polish, and maybe lipstick."

"That is fine. I can deactivate the security with the wand."

I stepped back into the changing room, "Mom! I can't wear this around the mall."

"Lin, you have been wearing it around the mall."

She was right. "But, not out there." I stated.

"Would you prefer to try girl's shoes on and have a sales lady put make-up on you while wearing your jeans looking like a boy?" I could hear the unstated - don't be stupid.

I stumped my foot down, "I don't need all that" I could not believe I stumped my foot like a little kid.

Mom looked a little shocked, "Now you're acting like a little baby."

"Mom, please."

"Lin, think of this as your dress rehearsal. This is how you're going to school tomorrow." She took that motherly tone - I know what is best.

Then I heard Mrs. Harris, "You won't be alone. Kevin will be with you."

Mom looked at me, tilted her head slightly and gestured see you have nothing to worry about.

Cynthia chimed in, "You two are so pretty. There is no reason for you to be embarrassed."

"See, now let's get going, we don't have all night." Mom handed the clothes we were buying to Cynthia. Then she gathered up my old clothes.

Cynthia folded the clothes over her arm, "The blouses are two for one; you still get a second blouse. I would suggest the red."

Both Kevin and I had to wear our old sneakers with our new outfits. We looked comical wearing old skateboarding shoes with skirts. While Mom and Mrs. Harris paid for the purchases, I positioned myself behind a rack out of view. Kevin stood in the open wanting to talk. He acted as if nothing was different. In a way, I wished I had his attitude, his self-confidence.

Mom handed me the bag. Kevin and I followed our Mom's to the shoe store. Luckily, it was just one store down and no one was around. Once there, Mom had to look at every shoe. The sales lady was older and foreign. She had one of those red dots on her forehead. She did not say anything or ask any questions; like why boys are wearing dresses. She looked at me in an odd, disapproving way. I felt uncomfortable. I wanted to hurry the process. Mom wanted to ensure the shoes fit well and were comfortable. I kept looking at the sale lady while Mom asked her questions, "How do they fit? Are they comfortable? Do you like them?" I did not want to answer that question with the sales lady staring at me, but I also did not want to make a seen, "They feel good." I ended up getting a simple low heel black paten leather pump. Kevin picked out a pair of pink and white tennis shoes. We each wore our shoes out.

I followed close behind Mom, using her as a screen to hide behind, as we walked to the next store. Mom and Mrs. Harris talked about what make-up would look best on us. I heard Mom say to Mrs. Harris, "to bad Lin's ears aren't pierced." Then the two talked about jewelry. I had the urge to act out, to remind Mom I was her son, not her daughter. However, I did not want to do anything that would bring attention to me. I thought Kevin was window-shopping as we walked. As we rode the escalator up, I felt on display. Kevin looked at the nightgowns on the racks below. At first, I thought it was good that the cosmetic counter was near the store entrance. Then I realized I could see down the entire mall. Anyone walking the mall could see me.

Two very beautiful women stood talking next to some stools. The older salesgirl was well tanned and had shoulder length black hair. The younger had paler skin and long blonde hair. Neither was shy with us.

"What do we have here?" The older asked.

I turned red. I could see the statement even made Kevin uncomfortable.

"So what are your daughter's names?" The younger asked. I heard the emphasis on daughters.

"These are our sons," Mom stated. Again, she did not make any effort to explain why we were dressed the way we were. "He needs lipstick and nail polish to go with his new outfit," Mom put her hand on my back to move me forward.

"And maybe a light eye liner," Mrs. Harris stated.

The older saleslady went into her sales pitch, "They are both very lovely. I have several nice shades of dark pink, almost a fuchsia; they would go nicely with her - his top." She motioned for Mom to follow. We went to the other end of the counter. She had me sit on a stool. I saw Mom shake her head, in that disapproving way. She then whispered in my ear, "Cross your legs dear."

I did not see what was wrong with the way I was sitting. It was how I always sat. However, to avoid a public argument I did as Mom requested. I crossed my legs and straightened my skirt. The salesgirl smiled. "That's better," she said then winked at me.

"Which would you like to see first?" She asked me holding up three tubes of lipstick.

I looked at Mom.

She was no help, "Pick what you would like dear."

I looked back at the tubes. It did not really matter to me. I did not want lipstick. I wondered why Mom thought I needed lipstick. It struck me that they thought I was trying to choose the correct lipstick, the lipstick I desired, not pondering the need for lipstick. I quickly picked the center tube.

"That's the color I would have chosen," The salesgirl said. She then looked at Mom, "Your son has good taste, an eye for fashion."

"Lin," I heard a familiar voice. We all looked over to the two girls standing next to Mom.

"Sue said it was you." Gail stated.

"Ah," I was stunned, "Hi."

"Wow, is that what you are wearing tomorrow?" Sue asked.

"Who are your young friends?" Mom asked giving Sue and Gail the once over.

"Mom, this is Gail and Sue." I usually avoided mentioning girl's names around Mom. She has a tendency to get goofy, asking a lot of dumb questions.

"Hi, it is nice to meet you," Mom turned on the charm. "If he had given me more time we could have done more. This will have to do for the last minute."

"Lin you look pretty," Sue stated.

"Yeah, you do," Gail added.

It was a confusing moment. I was embarrassed to be seen. I was glad that they did not laugh, but thought I looked pretty. I also felt the need to redeem myself. "Kevin is here. He's over there, the one wearing the mini-skirt." The girls looked in the direction I motioned.

"Lin can you look at me so I can apply your lipstick" The saleslady asked. Her statement did not leave any doubt about me being a sissy. Red faced, I did as she asked. I looked at the saleslady, but focused my attention over at the girls. The saleslady kept asking me to adjust my lips, form an 'O', curl them in, and pucker. She explained what the lip liner was, and the brush, and lip-gloss. While I was getting my lipstick applied Mom pulled the girls away to talk. I couldn't hear everything but I heard her ask questions. I wished mom would leave my friends alone. It was bad enough that I would be wearing a skirt to school; I did not need talk of me being a momma's boy.

"There" the sales girl stated. She handed me a mirror. "Do you like?"

Mom, Gail and Sue stepped up next to the sales girl.

"That is a nice shade on you," Sue stated.

"I wish my lips were as full as yours," Gail stated.

"He does have full lips. He's lucky; women are paying good money for collagen injections to have lips as full as his." Mom always finds a way to embarrass me further. She wasn't always like that. She used to be a cool mom. Now, I don't know what happened but she changed. It is as if all she wants to do is embarrass me, I do not like being with her.

"I like that color. Do you like the color Lin?" Mom asked, not waiting for my reply. "I also think he needs a little eyeliner." Mom stated. "What do you think girls?"

"Oh yes definitely," Gail stated.

"Maybe some mascara, to darken his lashes." Sue stated.

"Yes I think you girls are right," Mom said. "It is good to have you two girls here. He hasn't been much of a help. I hoped he would take a greater interest in his appearance."

The saleslady took a container off the counter. "I need you to tilt your head up and close your eyes. It helps if you look down, but keep your eyes closed." I did as she asked. As the saleslady worked on my eyes she explained to Mom and Gail the new properties of the lipstick. How the lipstick I chose actually gives a girl fuller lips. They all talked about what would look good on Gail. I wondered how long I would be stuck in the chair. I wondered what was happening to Kevin. I opened my eyes when instructed, so she could apply the mascara to my lashes.

"Lin, you are looking very pretty," Gail told me.

"You sure are," Sue added.

I wished they quit telling me that. Mom held the mirror for me. They were right. I looked like a girl, not a Tomboy, but a girly girl. "Those are your colors. Well take everything and the nail polish." Mom told the saleslady.

Just then, Kevin and his Mom walked up. Kevin was wearing a lighter shade of pink lipstick, but he had on more make-up around his eyes. He looked liked a pretty girl. I realized that was a good thing.

"Hi Gail, Hi Sue," Kevin said striking a pose; asking for a complement.

"Kevin," Gail got excited. "Wow, you look hot."

"Wow, Kevin you do," Sue said and then hugged him.

Mom turned around, "Kevin! You are very pretty."

I could see that Kevin enjoyed being the center of attention. We all stood in a group. Mom broke the silence. "Lin, put your make-up in your purse." She handed me the package. I blushed. I looked at the girls to see if they were silently laughing at me. Only Gail was looking at me.

"I promised Kevin ice cream," Mrs. Harris stated. "You are all invited to join us; my treat."

The girls jumped on the invitation. Kevin has always been a better friend with the girls then me. I did not want to go; I wanted to go home. I wanted to get out of the clothes. Mom accepted for us. Kevin and the girls started to walk away. Mom pushed me to catch up. She and Mrs. Harris followed behind. Kevin and the girls talked. I felt like a tag along. The fear of being seen was inhibiting me from having a good time. I occupied the time looking around the mall, curious if anybody was watching me. When we passed by another clothes store I saw a kid from my history class shopping with his mother. She was holding a denim skirt up to him. It was comforting knowing that Kevin and I would not be the only boys wearing a skirt to school tomorrow.

We never got the ice cream. We were half way there when it was announced the mall would be closing in ten minutes. That saved me from any further embarrassments.

Even though I was wearing a skirt, I still opened the door for my Mom. When we were all outside Mrs. Harris stated. "I owe you girls a rain check on the ice cream."

At first, I assumed she meant the girls, but she corrected herself, "Oops, you kids." I blushed, a deep red, only because Kevin and the girls giggled. I could see Mom also thought it was funny. To make matters worse Mrs. Harris apologized to me. "Lin I'm sorry. But you look so pretty; I forgot you're a boy." I guess there is a red deeper and brighter then fire engine red; it is called Lin's embarrassment red. I could see Mrs. Harris felt bad about embarrassing me.

The ride home was worse then the ride to the mall. Mom asked her questions about the girls. The number one question, which one do I like? After telling her we are just friends, she told me how Gail was nice and Sue was cute. She asked why I never mentioned them before. She asked why I never asked either one over, or to a dance. She told me if I ever wanted to ask one of them to a movie she would be happy to drive.

I started to get annoyed. To shut her up I asked my own question, "Do I look like a boy who can ask them out?" I was being flipped.

She looked over at me. She was silent for a moment. Then she asked me, "So the girls told me this isn't required. The whole dressing like a girl is optional. Is there something you would like to tell me?" Mom was not angry. She was being serious.

The question stunned me. I needed her to know that her son was her son and there was nothing wrong with me. "It was Kevin's idea. I didn't want to. I only agreed because Kevin asked and Tim agreed." She had to believe me, "Mom I swear it was not my idea to dress in girl's clothes. I wish I had never let Kevin talk me into it, I've been regretting it all night."

"I don't appreciate being lied to." I could not tell if she was upset with me or disappointed with me. "You should have been honest."

"I didn't think dad would have agreed, and I felt obligated since I gave the guys my word." I held my head down, "I'm sorry."

"You're right. Your father would never let you go to school the way you are dressed now if he didn't think it was required," Her voice was calm.

I felt guilty about lying, "I don't have to go to school." I saw an opening to redeem myself, "If you remember I asked to stay home sick. Dad said it was ok, you said I had to go to school."

"Don't blame this on me. This was your doing." The calmness left her, "And don't even think about staying home. I just spent well over a hundred dollars on those outfits. You are wearing them," She ended the discussion.

After a few minutes of silence, she asked me, "So if Kevin and Tim smoke pot are you going to?"

"No! That would be stupid," She was working the guilt, "I'm sorry. I won't lie to you again." I was being sincere, but not truthful. I would lie again if needed.

"You are stuck with this lie, I'm not telling your father. He doesn't need to know that his son wants to dress like a girl," I heard her threat. I was stunned; she was blackmail me.

When we got home, I went to change. Mom stopped me. She told me to finish my homework. She explained how there was not enough time for me to change. It would be quicker to clean-up before bed. I did as she requested. I had to; she had me. After Mom put my clothes away, she came into the study. She wanted to paint my nails while I did my homework. I protested, but it did not do any good. As I worked on my homework, Mom painted my nails. Dad stopped by the door and looked in. I looked up at him. I felt like I needed to say something that would assure him that his son was not a girly-boy. However, sitting there wearing a skirt, bra and panty, and mom painting my nails, nothing came to me. He shook his head, mumbled something, and then walked away.

After I finished with my homework, I got ready for bed. Mom had hung my new skirt and top in my closet. She put my new lingerie in my top draw. My purse was on top of my dresser.

Mom came into my room "I'll put your skirt and top in the laundry."

"Ok" I tried to sound happier. It hurt me that I lied to her. I wanted her to be able to trust me.

"Set your alarm a half hour early. I'll need time to get you ready."

"Mom thanks." She was a sucker for common courtesies.

Mom gave me a hug. "You can wear your panties to bed."

By her tone, I did not know if she was giving me permission or telling me to wear them. I was not sure how to answer, so I avoided the statement. "Goodnight."

She did not leave. She waited for me to undress. I knew then that I was going to wear the panties to bed. She tucked me in bed, and then she kissed me on the forehead like when I was little. She left my room turning the lights off and shutting my door. It was easy to wake up early, because I couldn't sleep. I spent the night worrying about school. What sleep I did get was troubled by a weird dream. I dreamt I was a girl and boys were chasing after me.

 

* * * * * * * *

 

Mom came into my room a minute after my alarm sounded, "Time to wake up; we have a lot to do to get you ready. You need to get a move on"

I did not want to walk around her wearing the panties, "Mom can I have some privacy?"

"Not today dear," She thought for a moment, "Think of yourself as a daughter not a son."

"Mom, that's nuts," She was into the cross-dressing day much more then I was. She was acting weirder then normal.

"Now get moving. Come on, out of the bed," I moved slowly. "Let me see your armpits," I raised my arms. "You'll need to shave."

"Mom I don't need to shave," She did not understand what she was asking.

"You don't have much hair, but you have too much. We're not European. Now do as I tell you. And you better run the razor over our legs."

I was going to be laughed at, and picked on, "You're kidding?"

"No." She did not look like she was joking, "Now move it. I still have to figure out what I'm going to do with your hair."

"What do you mean?" I was not expecting anything to be done with my hair. She went to the closet and started to take my clothes out. "Hurry"

I did not move fast. I stood in the bathroom, thinking about my options. I thought of sticking my fingers down my throat to induce vomiting. Mom would have to let me stay home if I was truly sick. I looked at my reflection. At the pink panties, I was wearing and the pink nail polish. I wondered what possessed me to agree to this.

Mom knocked on the door. "Don't waist time," She said to push me along.

I had promised my friends. I had to follow through, "Mom, where's the razor?"

"I'll get you one, brush your teeth," She said walking to her room.

While I brushed, she came into the bathroom. I brought some things you will need. She turned the water on and started filling the tub. She dumped her bubble bath in. I tried to talk to her while brushing. She understood what I was asking. "The bath beads will make it easier for you to shave. You don't have time to soak, but you should enjoy the hot bath. Use my shampoo on your hair." She took my shampoo and set it on the toilet tank. I brushed, and brushed, leaning up against the sink. I wanted her to leave before turning around. Moreover, I was not going to step into the bath with her in the room. Know matter what she said, I was not her daughter.

"I'll get the rest of your clothes ready," She left me alone.

I quickly spit the toothpaste out, stepped out of the panties and sat in the tub. The water was hotter then I expected. After a minute, my body adjusted. It felt good. The hot bubble bath was relaxing.

Mom walked in without knocking, "Mom! What are you doing?" I covered my privates.

"I brought you a robe," Mom hung a pink terry cloth robe on the door hook. "Put it on when you're done. Call me when you're out, I'll fix your hair." Mom smiled at me, "Remember no soaking."

After she left I shaved. I did not have more then a half dozen hairs in my armpits. Because the hair on my legs where blonde and barely visible it was hard to tell where I shaved. The only way I could tell was by feeling them. My legs had become silky smooth. This did give me a feminine feeling. I would never admit that to anyone. I drained the tub and rinsed the bubbles off. After donning the robe, I called for Mom.

Mom came in caring scissors, a comb and some gel. She told me to sit on the toilet. She started combing my hair. When she picked up the scissors, I started to argue with her. She was in no mood to argue. She became authoritative and I became obedient. She combed my hair with a one-third part. Then she started trimming it so that my hair was long on top and short on the bottom. She complained that she should have used some highlights on my hair night before. I sat in silence, my hands folded on my lap, glad that she didn't.

After she finished cutting my hair, she worked on it with a blow dryer and brush. She kept teasing it out, trying to make my hair look fuller. She brushed some strands forward. She wanted them to hang down to my eye. When my hair was dry, she worked a lotion into it. My hair started to become stiff. She then told me she would finish it after I was dressed. I looked in the mirror before going into my room.

"What do you think?" I could hear the pride in her voice.

My hair was interesting. It was a feminine style, but somewhat wild. My hair looked messy and at the same time styled. Mom amazed me; I was surprised Mom gave me such a wild style. I knew several girls who will probably be jealous; their mothers would never let them out of the house with this hairstyle. Again, I was caught between being nice to Mom and telling her the truth. What she had done looked great for a girl, but it was not for me.

"I never would have suspected you could do this." I tried not to sound negative.

She made a strange comment, "We should have been doing this all along." She saw I was questioning her statement, "The doctors promised me girl. You were supposed to be Katelyn Marie." I could see she was thinking back, "Your father and I were both surprised; we didn't even have a boys name picked out." She went back to thinking about the past, "He was a very proud man that day. Deep down I think he wanted a son." She sounded hurt. I thought 'And I am letting him down'.

I asked a question I often wondered about, "Why didn't you have a girl, another baby?"

We sat in silence for a minute before she answered, "Your birth was a difficult one." I thought she was going to tear-up, "You're all joy we need."

My first thought from her comment was 'All these years Mom had been thinking about what could have been'. It was kind of sad and sick. I now understood why Mom was enjoying all of this, the shopping, talking fashion and just having a daughter to dote over. I felt torn between my parents, as if I had to choose who should be happy. I decided I could give Mom a day. I would survive and Dad would get over it in time.

"I better get dressed," I told Mom feeling a little more excited about the day.

"Call me if you need help," She forced a smile.

Everything was laid out on my bed. I dropped the robe and slipped on the black panty. It was a different style. They were made of lace and cut like a very short cut shorts. Like the pink panty, they felt very sexy against my skin. I quickly slipped on the black pantyhose as Mom showed me. I went to put the bra on but it was different then the pink one from the night before. It had padded cups, thin straps and it hooked on. I tossed it back on the bed and put my skirt on.

"Mom can you help me with my bra?" I asked her partly because I needed help and partly because I thought it would make her happy. Mom must have been waiting in the hall; she appeared a second after the words left my mouth. "Sure dear." She was delighted to help me.

I picked the bra up and handed it to her. She instructed me on how to put a bra on. She then adjusted the straps for a proper fit. Looking down and seeing budding breasts was a strange sight for me. I wondered how kids in school would react to them. It is one thing to dress in girls clothes. It is entirely different statement to present yourself as a girl. I started to protest, "Mom," was all I said when she started talking.

"Wait to see the difference this bra makes with the top. I realized my error last night when you first tried the top on. A girl your age would have certain assets." She held up the black top for me. "I'm sorry I cut you off. Did you want to ask me something?"

I looked at her. She looked so happy. I thought, what the hell, it is only for a day. "I was just going to thank you."

She smiled, "Finish getting dressed."

She helped me with my top. Having breasts, even small ones, changed how the top fit me. It was snug and looked sexier. I wanted to put my blouse on to try to hide the breasts. I wondered if girls became embarrassed or proud when their breasts started to develop. I assumed proud, but that did not change how I felt. I wanted to hide them.

After I sat on the bed to put my shoes on, Mom gave me my second lesson on being a girl, "Dear when you sit, you need to tuck your skirt." She told me as she illustrated, "Now you try." I stood, and then sat again tucking my skirt. I looked at her for her approval.

"And never spread you legs. That is not proper. Cross your legs," She said crossing her legs. "Or you can cross them at your ankles and keep your knees together," I did both as she told me.

"Remember," She rested her had on my lap, "never spread your legs. You don't want to show your panties to the boys. And you don't want them to get the wrong idea about you."

"Mom!" that was embarrassing.

She kissed me on the cheek, "Sorry dear."

I sat on the bed and bent to the floor to slip my shoes on. I had a hard time slipping them on. Once I had the shoes on, I stood. "What do you think?"

"First you need your belt," I slipped the belt on. "When you stand, stand straight. Don't slouch." I straightened. "Don't fold your arms across your chest."

"How is this?" I dropped my arms and tried to be confident.

She stood there looking at me.

"What's wrong?" I thought she was going to cry.

"Nothing; let's get your make-up on." She turned away.

She had me follower her into their bedroom. She told me to sit at her dresser. I sat tucking my skirt. Then I crossed my ankles and pulled then under the stool. I set my hands on my lap. It was a comfortable position. "I'm all yours."

Mom smiled. "You know we would have more time if I drove you to school."

I did not need to ponder the offer. "Ok," It was a relief not having to walk or ride the bus. "Oh wait, Kevin. I promised him I would ride the bus with him. I hate to leave him alone. I knew I wouldn't want to be ditched dressed like this."

"We can pick him up." Mom handed me my purse. "You try putting your lipstick on while I make the call." I took the lipstick out of my purse. I remembered what the saleslady did last night. I leaned in close to the mirror and applied my lipstick. After I applied my lipstick, I took out the small brush. I followed the edge of my lips. Appling make-up was easier then I expected.

"You're a natural," Mom said. "We will take Kevin; Mrs. Harris will pick the two of you up after school."

"Thanks Mom." This was one time I did not mind having Mom give me a ride.

"Honey, don't you like the way you look?" I could not tell from her tone if she was asking - do you like how I dressed you, or was she asking - do you like dressing like a girl. I felt like she was asking a trick question. I had to be careful how I answered. "I like what you bought me."

I never got the 'but' statement out, "I'm so glad you like your outfit. I worried." She paused, "That doesn't matter. I think you'll be the prettiest boy in school today."

I was glad she did not call me a girl. I tried to stay the fear that was starting to come over me. Being the prettiest boy was not a good thing, "Thanks Mom." I only had a few more hours to go and my life would be back to normal. I told myself, 'I can do this'. I sat in the chair while Mom worked on my face. She had me try my hand at putting the highlighter and mascara on. Applying make-up to my eyes was more of an art form then doing my lips. Mom had to fix everything I had done. Once she was finished, she had me repack my purse. Then she walked me over to her full-length mirror. She stood behind me, a proud mother. I saw what she saw; the daughter she never had.

"I'm glad you decided to participate in the day's activity." She set her hands on my shoulders and gave me a small squeeze with a smile.

I thought what the hell. I did what any daughter would do. I turned and gave Mom a hug. It had been some time since I hugged Mom. Hugging is not something teenage boys are supposed to do. It's required that you hug your aunts and grandmother, but not your Mom. I sensed my action delighted her. I felt the warmth and love in her hug. I wondered why I quit hugging her.

Mom did all the talking driving over to Kevin's house. I was not ignoring her, I was nervous. I am usually quiet, and in school, I am often nervous. Not a fidgety nervous, where you bounce your knee constantly, but an untrusting nervous. I learned early on that most kids are cruel. There were only a few kids like Kevin, nice kids. Kids you would want as a friend.

We pulled into their driveway. Mrs. Harris hugged and kissed Kevin at the door. He was wearing the denim mini skirt with a pink top and white blouse. I was relieved to see that he was also wearing a padded bra. I did not want to be the only boy sporting boobies. Watching him walk to the car was like watch a girl walk. It was a strange, but I saw a girl. Kevin had long blonde hair that he parted in the middle. He usually tucked his hair behind his ears, now he had bangs and it curled in slightly. Mom rolled down the window and waved to Mrs. Harris. Kevin looked back. When he turned back around, he flipped his hair like a girl. I wondered how people would see me, would they see a girl or would they see a boy in drag.

"Hi Mrs. Troy, hi Lin" Kevin's voice sounded soft and innocent.

"Hey" I stated.

"Hi Kevin, you look pretty today" Mom was also taken back by how girl like Kevin was.

Kevin beamed a smile. "Thank You."

He opened the door. When he sat, he tucked his skirt then swung his legs in the car. His knees never parted. After he shut the door, he flipped his hair again. I could not help thinking it the dude was a girl, a cute girl. The ride was different then usual. We all talked. However, Mom did not ask questions. She complimented Kevin on his hair and his make-up. Kevin complemented her on what she did with my hair. I felt I should throw out a compliment, but that felt awkward.

Mom pulled up to the drop-off zone. I saw Gail and Sue waiting for us. I suddenly became very scared. I did not want to leave the car. Kevin got out and waved to the girls. They each gave high-pitched screams and ran over to him. I looked to see how many kids where now looking our way. Sue and Kevin hugged. Gail looked at me still sitting in the car.

Mom put her hand on my shoulder, "go ahead dear."

"I can't do this."

"Your friends are waiting. You'll be fine."

Gail opened the car door, "Hi Mrs. Troy, Hi Lin."

"Hey"

"You coming" Gail held her hand out to help me out of the car.

"Don't forget Mrs. Harris will pick you boys up after school," Mom reminded me as I got out of the car.

Gail hugged me when I stood. Then she held my hand and stepped back to look at me, "Wow! You look hot."

Sue then complimented us on our appearance. I did not think the girls looked any different then usual. They were wearing jeans and T-shirt. I did notice Gail was not letting go of my hand.

I looked around, "Have you seen Tim?"

"He's inside." Sue said.

"What is he wearing?" Kevin asked. "We kind of left him on his own." Kevin sounded apologetic.

"Don't worry about him. He is in jeans and a t-shirt. He chickened out." Gail stated.

I thought now he is going to think I am a sissy. I don't know why that mattered but I did not want people to think I was a sissy. It was ok if Kevin was a sissy, but I wasn't.

Gail tugged my hand, "Come on lets go."

It was comforting to have Gail hold my hand. We walked together into the building. Gail, Sue and Kevin chatted. I think everyone saw that Kevin was a natural at being a girl. I hoped since Gail and I were holding hands kids would see me as her boyfriend. I saw Tim talking with some of the football players. They all chuckled when they looked over at us.

Tim walked up to us. "Look at the girly boys."

"I thought we had a pact." My annoyance was obvious.

"My Dad said that only sissy fags would wear girl's clothes. I'm no sissy fag," He laughed.

His words hurt. His cruel laugh hurt more; I thought we were friends. Gail urged me to walk away. I wanted to lash out at him. I made a fist. Tim saw that and took a confrontational stance, "You got something to say sissy?" I did, but was not dressed for fighting. I was angry, but I turned and walked away with Gail. I did not look back. I heard Tim, everybody heard Tim, "That's what I thought, faggot." The last thing I wanted was to be seen crying. It was not the time to act like a sissy; I needed to be tough.

The day was filled with mixed emotions. There was only a hand full of boys who cross-dressed. I had thought, hoped, many boys would have participated. Since such a small number cross-dressed, I started to wonder if I was different. I did turn heads walking down the corridor. I questioned if that was a good thing or a bad thing. When kids called me names, I found myself wanting to agree with them. When I received compliments, I felt good about what I was doing and myself. It was always comforting when Gail, Sue or Kevin was with me. When alone I tried to keep my head up, but it was hard to resist the urge to want to just disappear.

At one point, I became ashamed of my actions; I should say lack of action. I saw the boy from the mall. He was wearing a flowery dress. Some boys had him cornered and were teasing him. I thought of helping him. I knew it would be the right thing to do, but fear of becoming their second victim stopped me. I walked past, head down, doing nothing.

Every time I saw Kevin, he was walking, talking or giggling like a girl. If I did not know it was Kevin, I would never suspect he was a boy. I wondered how others were seeing me. I wished I could see myself as they did, for I did not want them to see me as a girl.

 

Mrs. Harris picked us up as planned. I thought she was going to take me home, but I went to their house. Mrs. Harris told me that my mom would pick me up later. When we got to their house, she told Kevin not to change; it would not be fair to me. I don't think Kevin minded. We spent the time in his room playing video games. It did not matter how we were dressed, we were still Kevin and Lin, best friends playing video games. I did notice that when Kevin returned from the bathroom, his lipstick was freshened.

Mom picked me up late. She and Mrs. Harris talked for almost an hour. Kevin and I watched television. I tried to ease drop on their conversation but they were talking softly.

"Time to go," Mom, announced.

I picked up my book bag; remembering to bend at the knees. I was almost to the door when I realized I was forgetting my purse, "Just a second I forgot my purse." As I turned it dawned on me what I had just said. I felt like I should qualify my statement. Kevin handed me my purse and walked me to the door. We said our good byes. Mom asked me questions as we walked to the car. I told her that Tim did not dress. I was not going to mention his comments but she kept prying. Finally, she told me that I was better off with true friends like Kevin, Sue and Gail.

Dad was not home when we arrived. Mom told me to change and be quick about it, that we were all going out for dinner. As I hurried to my room, she told me to wear something nice, and to put my clothes in the laundry. Once in my room I studied my image in the mirror. I thought of my day. I thought of Mom's question, "Did you have fun?" I answered her by shrugging my shoulders, "I guess." I looked at the girl in the mirror, "Did you have fun?"

That night we went to a five star restaurant. Dad announced that he had been promoted to vice president of sales. He was now responsible the entire Midwest. The promotion meant a big raise, and that he would have to travel more. He would be gone three to four days a week. He told me because of all the traveling he would not be able to coach the basketball team, which he apologized. I told him that it was ok. It actually was a relief, because I did not want to play basketball. Mom appeared happy for dad but she also seamed a little distant. Neither one of them mentioned my day.

 

Chapter Two

 

As far as I knew my parents had forgotten about cross-dress day. I did nothing but think about that day. It sounds silly but I wondered if I had changed. The reason I worried about if I changed was because; Kevin had changed. It is as if he went girl. He dresses like Kevin but his mannerisms had become more feminine. Tim and his friends have taken to calling him Sissy. I did not want to be nicknamed Sissy.

My skirts and blouses were hanging in my closet. My bra and panty sets were in my dresser drawer. When I saw the clothes, I thought of that day. Thinking of that day always gave me a feeling of delight. The feeling of delight confused me and brought on a feeling of guilt. I became curious. Not about how I would look, I knew I looked cute. I wondered how I would feel. If, I were alone, not around Gail and the others, would dressing like a girl give me that joyous feeling? I worried that if I wore the clothes again it would change me.

I did not have to wait but a few days to find out the answer to my question. On Saturday, my parents had decided to go out to diner and a movie. Mom was a little concerned about excluding me, but I told them to go and have fun, I would be fine. I had my own plans and their date night was what I needed.

I waited a half-hour before putting my plan in action. Since it was only few days since I lasted shaved, I did not need to shave again. I went to my room and stripped out of my slacks and shirt. I pulled out my black panty. I then hesitated. I guess part of me did not want to know how dressing like a girl was going to make me feel, or I was afraid I would not like how it made me feel. What if that calming feeling, the feeling of wellness that I remembered was real and not imagined.

I slipped the panties on. Wearing the panties gave me a joyous feeling, but it was not that feeling I remembered. I tucked myself so as not to have a bulge. I took my padded bra out of the drawer and slipped it on just as mom taught me. I looked at my image in the mirror. I felt a tingle of pride at seeing my small breasts. Feeling some pride at seeing imaginary breasts worried me. I started to doubt what I was doing. I thought that maybe I found the answer to my question. I decided the only way I would truly know how cross-dressing made me fell was to continue. I slipped on my black pantyhose. I put on my favorite skirt, the pleated skirt. I decided to wear the off red top with the white blouse.

I went back to the mirror. I was disappointed with how loose the red top fit. I changed into my black top. I liked how it hugged my torso and showed my breast. The nervous feelings I usually have disappeared. It was replaced with the feeling I had the other day. It is hard to explain the feeling; it is a combination of a calming and giddy feelings. I wondered if Kevin got the same feeling.

Determined to finish what I started, a total transformation, I went into my parent's room to apply my make. I guess it was being in my parent's room that brought on the guilt. I sat staring in the mirror. I pondered life's questions. Who am I? What am I? What am I doing? I never applied make-up. I felt I was becoming a person dad could never be proud of. Coming to that conclusion was disappointing. Feeling disappointment worried me. Dejected, I went back into my room and changed back into my normal clothes. I vowed then that I would never wear girl's clothes again.

The Monday scout meeting was at Kevin's house. After the meeting, mom and Mrs. Troy chatted. That gave Kevin and I time to play video games. While playing, I saw Kevin still had his girl clothes hanging in his closet. I thought about the fact that we never discussed that day. I wanted to say something, tell him that I did not care if he liked to dress like a girl, but how do you start that conversation.

"You still have your clothes?" Kevin asked.

"What?"

"Do you still have your skirts and stuff?" His voice got softer as he spoke.

"Ah, yeah, the kidney people haven't come yet."

I could see he did not understand my statement, "the Kidney Foundation, they raise money selling second hand clothes, you set your clothes out, then they pick them up and sell them in their store."

"Oh, right," He paused, "So you're giving yours away?"

"Yeah," I hesitated. "You, are you keeping yours?"

"Why ?"

"I just thought," I felt the conversation was getting to personal, "I thought that you might keep yours."

"Why do you think that?" He wasn't being defensive.

"You were, I don't know, I thought you had fun - as a - girl."

He sat there staring at me. I knew he wanted to tell me something. The video game had ended. Neither of us attempted to restart the game. We sat in silence. It was an awkward moment.

Kevin broke the silence, "Gail and Sue thought you really enjoyed being a girl. They asked me to ask you if you would want to go as a girl for Halloween. The two of us, you and me, with them, so what do you think?"

My first thought was of the promise I made, "I don't know."

"I was just asking. It could be fun," I could see the hope in his face.

"I don't know. I don't think my Mom would let me," I did not want him to think that I thought he was weird.

"Let you do what?" Mom asked standing in the doorway.

"We were discussing going as girls for Halloween," Kevin told her.

"That is a great idea," Mom got excited.

I wanted to protest but it was too late. I should have said my Dad wouldn't let me. I did not know what to do. Mom did not understand. She did not know how I felt about dressing like a girl. She did not understand had I feared dressing like a girl. She just kept suggesting ideas for costumes.

It looked like I was going to go as a girl for Halloween, "A Goth girl, I like that, it sounds in." I looked at Kevin.

"Yeah, I like that, thanks Mrs. Troy."

 

The End.  

  

  

 

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