It was a Thursday afternoon, July 14th. I remember because we lost power, and my life changed. Without the computer or television to entertain me, I became bored. Looking for something to do, I noticed the laundry basket full of Sis’s lingerie. To this day, I could not tell you why I was curious.
Curiosity Killed The Boy
My older sister always had more clothes than I. Her closet and dresser were full. The closet in the spare bedroom was packed with outfits that didn’t fit her or were deemed out of style. There were boxes of her old clothes on the floor of the closet. Since Monica took care of her clothes, Mom had a habit of saving her stuff. “You never know when they may come into use,” she would say.
It was the Summer of my twelfth birthday. Sis had a job in the pretzel store in the mall. Mom worked part-time at the fast-food restaurant. At times there shifts overlapped, and I was left home alone. Mom worried. She set many ground rules; no using the stove, no friends over, and don’t leave the house. I spent most of the time playing games on the computer.
It was a Thursday afternoon, July 14th. I remember because we lost power, and my life changed. Without the computer or television to entertain me, I became bored. Looking for something to do, I noticed the laundry basket full of Sis’s lingerie. To this day, I could not tell you why I was curious. All the colorful panties caught my attention. Wondering what they felt like, I picked up a red panty with lace trim. They were so light and smooth. I thought about trying them on when the power came back on.
I played games for about a half hour. All the time I kept thinking about the panties. I went back to the spare bedroom. In the dresser draw where some of her old delicates’. I pulled out a pink training bra. I saw the panties that went with the bra. I quickly undressed. I picked up the panties. I thought, what am I doing? My penis started to swell. This was something new for me. I discovered masturbation a few months back. When I wasn’t playing games, I liked to masturbate.
I slid the panties on. They had ruffled elastic trim. I became very stiff when I ran my thumbs along the edges adjusting the panties into the proper place. I decided to put the bra on. I was sure it would add the experience. It was erotic. I looked to see what else was in the dresser. I pulled out a white chemise with spaghetti straps. I didn’t hesitate to put it on. I could feel I was creaming my panties. I continued my search. I found a pair of red tights. I struggled a minute until I figured out how to don them.
I stood looking at myself in the dresser mirror. I couldn't see everything. I went into my sister’s room. She has full-length mirrors on her closet doors. I was amazed at how girlish I looked. I went back to the spare bedroom closet to look for a skirt. I wanted to wear a denim mini skirt. There were several to choose from. I picked a faded skirt with a fringed hem. I grabbed a red T top. I went back to my sister’s room.
I felt pretty. I could have been born a girl. It didn’t take long until I became fixated on masturbating. I started to rub myself. I went into the bathroom; I hiked up my skirt and pulled down my tights and panties. It didn’t take long. I found it strange. Once gratified, I was overcome with guilt. Part of me wanted to stay dressed because I loved how I looked. The guilt made me feel ashamed for wanting to stay dressed. The shame won out.
I put everything back the way it was and went back to playing computer games. The entire time I killed aliens, I thought about how pretty I looked. I started to wonder what it would be like to wear make-up. I thought, the next time.
Since the divorce things have changed. Sis and Mom work more, and the house isn’t as tidy. Mom is more stressed. She complains about money all the time, and my good-for-nothing father. Some changes have been for the better. Mom and I haven’t received a thrashing; her for being a whore, and me for being a dumb ass. I was growing my hair long.
It used to be a ritual with my father. Every June, after school let out, we would go to the barber and get buzz cuts. I didn’t go to the barber that often. I got a buzz cut in June and a trim before the holidays. Dad would say, “Now you look like a man; not some fucking sissy faggot." I was told I got my first thrashing over a haircut; my refusal to get one. I don’t remember. I just know I always hated hair cut day. However, I learned to heel. “Good boy,” He would tell me rubbing the peach fuzz on my scalp.
I sat in Sis’s room brushing my hair. I was wearing a white bra and panty set. I moved up from the training bra. It improved my image having budding breasts. I tried several technics for stuffing my bra over the week. I got the best results with cotton balls and a semi padded bra. As I brushed I thought about what I wanted to wear. I had already tried on most outfits in the closet. It was like I spent the week clothes shopping. I would put on an outfit. Step in from of the full-length mirror. Turn left, turn right, check out my butt and bust, and try on a new outfit. I liked miniskirts with a spaghetti strap T shirts the most.
I thought about wearing make-up. I tried my hand at it a few days back. The result bordered on comical. I looked like I was trying out for clown school. Since then I had been watching YouTube videos on male to female transformations. Sis didn’t have all the cosmetics they used in the videos. Instead of trying everything I decided to work on one feature at a time. I had on pink lipstick with gloss. The pink stood out against my white skin tone. I saw Sis had matching nail polish. I wanted, and was afraid to paint my nails. I worried it wouldn’t all clean off. Mom and Sis would see that I wore nail polish.
I continued to brush my hair. It covered my ears. I wondered how long I could let it grow before Mom said something. I wanted hair down to the middle of my back like Sis used to have. The only time I remember Dad getting mean with Sis was when she cut her hair. “What do you think?” she asked with a smile, modeling her new short blonde hair. “You look butch. You aint a lesbo are you?” Dad was series. The next day she had her hair curled so she would look more girly.
I parted my hair down the center. I brushed my bangs down. My hair looked terrible. I knew a stylist would be able to fashion what I had. The barber would ask, “number 3 or 4?” I brushed my hair back. I needed it to grow. It still wasn’t long enough to put in a ponytail. I would be pretty with a ponytail and bangs. I would be prettier as a blonde.
I gave up on my hair and decided on an outfit; a black flirty skirt with white dots and a grey T shirt. I put on black tights. I learned about tucking on the Internet. That trick helped my appearance. It is hard to look feminine with a boner. I slipped on my sister’s heels. I learned walking in heels takes practice. I wondered how girls danced in heels. I stepped in front of the mirror, my ankles wobbling. I stared at the pretty girl staring back. Looking pretty was a euphoric feeling, an overpowering feeling that I wanted all the time. I could feel myself becoming aroused. I didn’t want to be aroused. I couldn’t help myself. The only feeling stronger than the euphoria was the guilt I felt after masturbating. I wondered if the guilt came from the fact I knew if dad ever saw me like this he would beat me. I turned left then right. I was pretty, I knew it, and I was going to enjoy the time.
Three
I sat on my bed wearing an aqua baby-doll night gown and panty. The cotton balls were stuffed between my toes. I shook the bottle of red nail polish, thinking about the risks. I didn’t think it likely that Mom or Sis would ever see my painted toes. It would only be for a few days. I was confident I would never be caught. I found it exciting to have a secret. Like when I wore panties for the entire day. Mom and Sis never knew. I knew, every time I stood or sat I felt the panties caress my bottom. It made me feel naughty, and I found that exhilarating.
The nail polish felt cold as I applied it to my nail. I didn’t expect to feel anything. The feeling was yet another unexpected delight. What I thought would be a miserable lonely summer cooped up in the house, has turned out to be one full of enchanting experiences. I looked forward to each day. There were so many things I wanted to accomplish and experience each day. I spent the morning soaking in a warm bubble bath. I shaved my legs for the first time. My legs had a minimal amount of hair. Now they had none; silky-smooth skin. I finished the nails on my left foot. I sat admiring my work, waiting for the polish to dry before starting on my right foot.
The new look was amazing. The nail polish turned my dogs into sexy feet. I couldn’t stop looking down and admiring my feet as I walked through the house. I stopped at every mirror. I smiled. I was beautiful.
I had moments when I wondered if there was something wrong with me. I would think; Normal boys wouldn’t want to look pretty. Then I would think, What is wrong with wanting and enjoying looking pretty?
I spent the next hour playing video games. The need to masturbate had subsided over the week. I could enjoy playing games while wearing the baby doll. It was feeling right, normal. I doubted Mom or Sis would be happy if I wore it in the evening. It was close to lunch when I decided to get dressed. I tried on several outfits. It took time to determine what I wanted to wear. I settled on a red bra and panty set with a floral sundress. I thought the red rose buds complimented my nail polish. I finished my look with the red lipstick that matched the nail polish and a pair of red heels with an open toe.
I ate a salad for lunch. I quit eating fatty foods and drinking soda. I decided to watch my weight. I am slender, one hundred and twenty-five pounds. From the charts I saw on-line for girls; my weight should be closer to one hundred and ten pounds. I didn’t think I could lose the weight, but I was determined not to gain anymore pounds.
After lunch, I went into my sister’s room and practiced putting on lipstick. I wanted to try different technics. I used the liner pencil first. I then brushed on the red. I gently smeared my lips together. Then I applied a dab of gloss at the center. I liked the look. I cleaned the lipstick off and applied just the red. I liked how deep the red lipstick looked. However, I liked how the gloss sparkled better. I added the gloss.
I thought about working on eye make-up. I left her room and logged onto my computer. I watched several videos on how to create dark sultry eyes. I wished I could discuss this with Sis. She’s great at applying make-up. She knows how to look pretty with just a bit of make-up, and she knows how to use make-up to look sexy. I would learn so much if she walked me through step by step. One could only dream.
Four
It had been three weeks since the day I wore my first outfit. I’ve started making some minor modifications to my daily routine. I took baths, long hot bubble baths, instead of showers. I’ve been shaving my legs, armpits and private area. I started wearing panties. I slept in a night gown. Part of me thought I was making too many changes to fast. The joy I felt each day only encouraged me to go further.
“Mom. Did you use my lip stick?” Sis asked.
“No,” Mom looked at Sis. “Why?”
“I don’t know. I just thought somebody used my lipstick. I could be mistaken,” Sis didn’t stop to elaborate. “I got to go,” She kissed mom on the cheek and walked out twirling her keys.
Mom stood in the kitchen, thinking. She looked at me, “You didn’t have any friends over did you?”
“No,” I blurted.
She looked at me. She had a way of communicating without talking. Her look was asking, “Are you telling me the truth?”
I sighed, “I never let anybody in the house. I never leave, and I don’t use the stove. I follow the rules."
She was pondering what I told her. She asked, “What do you do all day?”
I wondered if she suspected. She couldn’t know. Whenever I went into Sis’s room, I have been very careful to put things back the way I found them. “I told you, I play video games and watch TV,” I felt the panty caress my bottom while adjusted my position.
“I’m thinking I should have been giving you chores for each day. You waste too much time on the computer and playing that Xbox."
“I have my chores. I mow the lawn on Saturday. I take the trash out and bring the cans up,” I complained.
“Your sister and I go to work each day. You can do more. I want you to do the dishes and clean the kitchen today.” She looked at me, “Before I get home."
“OK,” I didn’t think it was fair. However, I was happy the subject was changed.
“That includes mopping the floor,” She went to the closet and pulled out the Swiffer. “You can use this. It has the cleaner in the bottle."
“I’ll clean the kitchen."
After mom left I took my bath and got dressed. Since I had chores, I decided on a denim mini skirt with a pink T shirt. I thought it best to not to use Sis’s make up. Until then, I never went into Mom’s room. Both my parents had rules about their bedroom. There was no reason for us kids to be in their room. We were to stay out. If, for some reason, we needed one of them, like Sis was dying, we’re to knock and wait for one of them to answer. One time I broke the rule. Mom sounded like she was in pain. I opened the door. Dad gave me a thrashing. He called me a peeping Tom and pervert. I went into Mom’s room. I didn’t see what was so special about the room. I saw the make-up on her dresser. She had an extensive make-up kit. I went with a deep red lipstick. I decided on using mascara. She had several to choose from. I picked out the tube with fine bristles. My lashes looked fuller. I liked the effect.
It didn’t take long to do the chores. I spent an hour in Mom’s room looking through her dresser drawers. She had different lingerie than Sis. Sis liked the Victoria Secrets Pink line. Mom had more sheer and laced panties. Her bras were bigger. I wanted to try on some of her lingerie but decided not to. Her stuff was sexy. I didn’t think it was what a twelve-year-old girl would wear. Sis’s old clothes were sexy for twelve-year-old. That is how I wanted to be viewed.
Five
“Starting next week you have to spend two weeks with your father,” Mom stated as a fact.
“What, why?”
“It is part of the divorce settlement,” Another cold fact.
“Is Sis coming?”
“No,” I see her minor shake of the head with a frown. Her way of saying, I’m sorry when delivering bad news.
“Why not? Why do I have to go and not her?” I once again get screwed.
“I have a job. I can’t get off."
Sis looked happy stating that fact. “I don’t want to go,” I was afraid of him.
“I’m sorry kid-o. It is part of the settlement,” She looked sympathetic.
“You said he isn’t paying. If he doesn’t pay, why do I have to go?”
“I know it isn’t fair. If, I violate the agreement, that would give him ammunition in court. You have to go, sorry."
I get screwed again, “That sucks." I didn’t mean to sound angry at her.
“Try to make the best of it. He is your father. I’m sure he will have fun things planned for you,” She tried to avoid arguing.
I realized she waited to tell me. She knew, “But he lives in West Virginia, what am I going to do there?” I realized it would mean two weeks without dressing. Two weeks in West Virginia being his son. I thought; He will probably drag me out into the woods and try to make me kill something. I hated him.
I turned the game off, stood up and tossed the controller on the floor, “This fucking sucks." I walked out of the room. I could see Mom wanted to say something. I assumed she was going to reprimand me for cussing. She didn’t say a word.
I went back to my room and flopped on my bed. Tears started to flow. It wasn’t fair. I just started enjoying life. I thought about changing. I thought about showing them how pretty I looked. I could hear Mom and Sis were talking, but I didn’t understand what they were saying. I got off the bed and slid my hand between the mattresses. I pulled out the baby-doll night gown. I felt around for the panty. I usually waited for them to go to bed before changing. That night I didn’t care about being caught.
My chore for the day was to clean my room and strip my bed. I was in a funky mood. I wore the baby-doll night gown with a white padded bra, and red high heel. I used Mom’s red lip stick. I applied mascara and black eye shadow. The look came off more Goth then sultry. I did a thorough job cleaning. Everything was put away; I dusted and vacuumed. After I was done I cleaned the nail polish off my toes. It was Friday. I could go to Dad’s like that and I didn’t think I would have the opportunity during the weekend.
Six
Dad was late arriving on Saturday. He was supposed to pick me up by noon, he didn’t show until three. He took one look at me and stated, “What’s with the hair?” I told him I was letting it grow out. Mom saw an opening, “If you sent the money you owed maybe I could afford to get him a haircut." Dad shook his head and told me to go. Mom wanted the last word, “See if you can have him back on time."
Dad spent the first thirty minutes of the drive asking me questions. How’s the summer going? Are you trying out for any sports? How’s your mother treating you? Is your mother seeing anyone? After the interrogation, he told me we were driving down to Lake Cumberland. He rented a houseboat on the lake. We were meeting his girlfriend Kimberly and her two sons Jake and Kyle. Mom always referred to Kimberly her kids as his whore and her two bastards.
Dad didn’t have a problem getting me home in time. I didn’t like Jake or Kyle from the moment, I met them. They were loud and obnoxious. They were always wrestling and hitting each other. They assumed I would enjoy the rough housing. They soon learned I wasn’t like them. Tossing me into the lake whenever I was outside became their little game. Dad started to join in. It was his way of encouraging me to lighten up. I tried to stay in my room as much as possible. As Dad put it, “You know how to kill all the fun in a vacation."
He didn’t get out of the car. He popped the trunk, so I could get my suitcase. I didn’t wave good bye. I walked into the house. Mom opened the door, “You’re father’s not coming in?”
“No,” I walked past her.
“Is everything OK?”
“Fine,” I continued to walk back to my room. I had spent most of the week and the ride home thinking about what I could have been doing. I thought about different outfits I could have been wearing. It would have been nice to have had a bikini for the lake. Instead, I got, “Don’t worry about getting dressed, wear your swim trunks. Kimberly isn’t here to do laundry."
Mom followed me back to my room, “What’s wrong, what happened?”
“Nothing,” I put my suitcase on the bed.
“Tell me what happened,” She sounded concerned.
“Nothing. Kyle and Jake are jerks,” I didn’t feel like telling her that Dad preferred them over me.
“What happened, what did they do?”
“Nothing,”
Mom came in and gave me a hug, “I’m sorry you had a miserable time."
Her hug was comforting. Without thinking I put my arms around her, rested my head on her shoulder and started crying. She stroked my hair, “it’s OK."
I pushed away from her and wiped the tears, “sorry."
“I’ll tell you what I’ll put your things away. You go ahead and play your games. Your sister will be back from the store shortly. We can all go out for a nice lunch.”
“OK,” I smiled. It was good to be home.
The day went as expected. Mom and Sis asked about the week. Mom wanted information about the whore. She wanted to know how much Dad had spent. I made it sound as terrible as I could in hopes I would never have to go again.
Mom didn’t work that day. Sis went in for the late shift, four to close. I wanted to go back into the spare bedroom and change. Being so close and not being able to indulge my desire was aggravating, and frustrating. Mom kept wanting to talk.
Before Sis got home, I decided to go to bed. Mom said good night and smiled. I went back to my room. I undressed. I didn’t want to wait until Mom, and Sis went to bed to wear my night gown. I knelt down and reached between the mattresses. I didn’t find the gown. I ran my hands in large sweeps searching. I became stricken with fear.
Seven
I checked my closet. The bra and panty I hid in a bag on the closet shelf were still there. I wanted to go into the spare bedroom and look in the dresser drawer for the night gown. Either Mom or Sis changed the sheets. Neither acted unusual nor treated me different. I assumed it had to be Sis; Mom would have said something to me. I paced the room wondering what I should do.
There was a knock at the door.
“Yeah,” I didn’t open the door.
“If you are looking for the night gown, I put it in the top drawer."
I could tell by her voice, she felt uncomfortable. I didn’t know what to say. Should I just say thanks, and acknowledge I laid claim to the night gown? Should I act as if I didn’t know what she was talking about? Should I be silent?
“Is it OK if I come in?”
“Just a second,” I slipped my pants back on. “Come in”.
She opened the door and peeked in, “Do you want to talk?”
Being face to face with mom changed how I felt, “About what?” Playing stupid was silly.
“About you wearing a night gown and putting on your sister’s make-up,” She looked at me questioning, am I right. “Not to mention it looked like you tried on almost every outfit in the spare bedroom,” again that look.
I didn’t plan to cry. A tear ran down my cheek, “I’m sorry."
“For what?” She walked over and hugged me.
“I don’t know. I shouldn't, I’m a boy; I shouldn’t wear girl’s clothes,” I wiped my tears away.
“Do you know why you did?” She looked at my face. I saw a concerned mother.
“I don’t know why I did. I was curious,” I shrugged my shoulders. "After I started I couldn’t stop. Being a girl makes feel good."
“Interesting."
“What,” I expected a different reaction.
“You said being a girl, not dressing like a girl."
I thought she was splitting hairs, “Same thing."
She smiled, “I’m not sure how I would have reacted if I caught you in your sister’s clothes. I think I would have been upset. Since I discovered the hidden night gown I had time to do some reading." She brushed my hair back behind my ear, “From what I read there is a difference."
“What’s the difference?”
“A person who enjoys wearing the clothes is different from the person who enjoys being a female,” She motioned for me to sit.
I sat on the bed.
She went to the dresser and pulled out the night gown and handed it to me. I didn’t take it right away. She motioned for me to take it from her. I set it on the bed. “Why don’t you change; I’ll come back in a few minutes, then we can talk.”
Eight
All week I thought about sleeping in the night gown. Now it lay next to me on the bed. Mom knowing what I liked to do, and being OK about it, should have been a relief. I should be embracing her acceptance. Instead, I sat hesitant. What if I want to go back? What if I never want to go back? I thought about what she said. Do I enjoy wearing girl’s clothes? Yes. Do I enjoy pretending to be a girl? Is it pretending? I know I am a boy. Correction I have a boy’s body. I had many questions and no real answers.
I changed into the night gown and panty. I sat on the bed waiting for Mom. Looking down at my body, I felt self-conscious and embarrassed. I thought about sliding under the covers. Instead, I got up and walked to the family room.
I could feel myself blushing when Mom turned and looked at me. I gave her a weak smile. She appeared to be delighted. I felt better.
“Come sit,” She motioned for me to sit next to her.
I sat.
“You look very pretty,” She brushed my hair behind my ear. “Maybe tomorrow we can do something with your hair. Would you like that?”
I nodded, smiled, “Yes."
“Your sister and I went through everything in the spare bedroom. She is happy to give you what you want in the room,” Mom looked at me.
“Thanks. That ‘s great,” I already was wearing what I wanted.
“I bought you some panties and bras. They are in your top draw,” Again, she paused.
“Thanks,” I wanted to go see what she got me.
While in the house you can dress how you like. We just ask that you don’t barrow our stuff or go in our rooms."
She wanted my acknowledgement, “OK."
“You’ll find some make-up on the dresser in the spare bedroom. That is yours to use."
I couldn’t believe everything she was telling me. I hugged her, “Thank you."
After hugging she got serious, “For now, I don’t want you leaving the house as a girl. In no way should you take that as your sister, or I are embarrassed of you. I just think it would be safer for you if nobody knew until you decide what you want."
I looked at her. I was fine with that. I didn’t want anybody else to know. I thought about what she said, until I decide, “What do you mean?”
“Like all young people, you need to think about your future. In your case, you have more options to consider."
I thought about what she said.
“Would you like to see a counselor?”
“I don’t know." I never thought about that.
"It may be good to talk to somebody, not family."
“If you think I should,” It would be nice to discuss how I felt. Maybe they could give me some insight or direction.
“I think it couldn’t hurt,” she smiled.
I hugged her again, “Thanks. I love you."
“I love you,” Mom rubbed my back.