Been Caught Dressing Since I Was 12!

by Christina Cox

 

Why did I do it? I do not know really why I had urges to dress in my sister's clothes.

I would come home from school before my older sister did in the afternoons. She was always involved in something (band, cheerleading or softball). She was always a good role model for me, being smart, strong, and caring. My mom worked late until dinnertime, so I had the run of the house until anyone got home. When did I start experimenting with my sister's clothes…well, I would have to say it was during one winter day. I was about 12.

Most of my friends would stay in and play videogames, watch MTV, or were active in sports during the winter. I would find myself alone and in the confines of my imagination and me. I would watch TV, do homework, and play video games too. If it were warm enough I would be outside. But eventually it just got too cold. I would be bored at home, and was walking by mom's room and saw a pair of high heel shoes outside the door. It seemed harmless enough; I decided to try them on. I was about the same shoe size as my mom. Now, I am a kid that has never dressed as a girl for Halloween or had fantasies of being a girl since birth…but I think my thoughts were going to change ever since this day forward. It was a strange feeling of height and power as I stood into my mom's shoes.

These were some basic 2-inch pumps, and despite the small heel I was a mess trying to walk in them. So I really started with my mom's stuff, even if it was just her shoes.

I looked at myself in the mirror and admired myself in the shoes. This got me thinking what I would be like if I was a girl. My mom's clothes were too big, but my sister's stuff was closer to my size. Julie, my sister, had some cooler teen clothes too. I had proceeded to her room and grabbed a pink dress that she had worn for Easter. Julie would kill me just for just being in her room, but I was looking to be girly the quickest way possible, so I picked out the pink dress. So I quickly changed and again admired myself in the mirror, now in my sister's room. So here I was in a pink dress and black shoes. I was starting to walk more comfortable in the shoes too. As I admired myself, I knew I was just a boy in a dress; I did not look like a girl. I was thinking now, how far or convincing could I become. My sister had tons of teen magazines with make up tips on the ground. I quickly saw the clock and I knew my sis would home soon, so now this would have to wait until tomorrow. I quickly put everything back the way it was, and decided to plan for more tomorrow. This is where my experiment all started to dress like a girl.

The next day to my delight was fabulous. I had now more time since I did not dilly-dally with TV or video games. I quickly rushed home and ran upstairs to find my mom's shoes, but her shoes were not there. She had returned them to her bedroom closet, where it was like I struck gold. My mom had all types of fancy shoes to pick and choose from. Even a pair of 4-inch high heels which I did not bother with. I picked out a pair of modest silver sandals. They simply wrapped my feet. They were very easy to walk in also! I quickly ran to my sis's room and picked out the pink dress. Now I began my make up lesson.

I quickly ran to my sister's desk where she had tons of make up accessories. I looked and just tried to apply lipstick (A simple pink shade). I was mesmerized by how it looked and I how I felt in the dress and heels. I knew I would have to do more in the days that followed to be more convincing. I played a lot in my sister's clothes. The weeks that followed before Christmas, it began to be a normal thing to dress for a few hours before dinner. All was good until one fatal day.

It was as usual; I came home, and quickly began to rummage for some clothes. I fancied the blue dress today, and found a pair of formal blue pumps; which were exquisite with my sister's blue shimmer dress. I got comfortable behind my sister's cosmetic desk, and began to apply the lipstick and now I have moved up to the eye shadow and cheek make up. I even started to wear some of her costume jewelry.

I was almost all done when; I heard the creak of the front door open!!!

"Oh shit", I exclaimed.

"Jesse, are you home?" questioned Julie.

"Hello?!", she yelled and questioned from the bottom of the stairs.

"Um, yeah, I will be down in a few minutes?" I answered.

"Okay, I am home early, school is not having afternoon activities, since it is almost Christmas!" she exclaimed.

"Are you okay up there?" Julie cried out.

"Um, yeah" I answered as I feverishly tried to get the jewelry off from me and kicked off the pumps.

Then I heard the thumping of the stairs, she was on her way up. Then it was too late, she opened the door. I was in a crouched position on my knees trying to pull the dress over my head and was stuck in the process. She saw me! I was caught!!

She was short winded and whispered in disbelief. "Oh my!?" She quickly turned her sight away from me almost to what I though was a shame, and said " Take it off now you f-ing sissy!" "Now I know what you really have been doing all this time, Amanda come quick!" she yelled down the stairs!

Oh my God, not only did I feel humiliated enough to be caught, now I am caught by sister and her friend, my school reputation is down the tubes now!!!

I quickly struggled to get it off, but it was stuck.

"Better yet, leave it on faggot!" she ordered.

I fell to the ground and began to whimper.

"Humph, you dress like a girl, now you are fitting the part by crying like one…Now I know why all of my clothes is always in disarray when I come from school, she male!!"

Then Amanda entered the room. Amanda was in shock.

She exclaimed several times turning her head, "Oh my God, Oh my God!!!"

Amanda quickly grabbed Julie and took her outside the hallway and they began to whisper and talk of some options they have. I could not hear all of it.

Then Julie brutishly popped her head in the room and told me to sit on her bed and stop crying.

"The damage is done" Julie said disgustingly "You are so in deep shit!"

Then Amanda shrugged Julie, and Julie said to Amanda, "Okay, and Okay."

Both girls entered the room. Amanda handed me some toilet paper and told me to wipe the tears from my makeup.

"Stand up", ordered my sister to me.

"Huh", and then I stood up.

The two girls walked around me in amazement and took good looks at me.

"You know, Jesse, if you wanted to be a girl for Halloween, all you had to do was ask, not be some closet cross dresser" said Amanda as she giggled with her statement.

"Do you like this Jesse" asked my sister. I did not answer her right away, but then I just told her how I was experimenting.

"You know mom has to know about this" said Julie.

Then I started to whimper, " No, no please don't tell mom, please I'll do anything, she doesn't need to know!"

"She doesn't need to know that you were in my clothes, in my room, invading my space!" exclaimed Julie.

Then Amanda held up a blue pump and stated, "Ahem, who do these belong too?"

"Well, that's not my shoe, they are a size bigger, hah, mom's!" answered Julie.

Then Julie was holding the pump and then a twinkle was in her eye.

"Well, maybe she doesn't need to know. Mom doesn't need to know on one standing condition" paused Julie.

" You like to experiment in girl's clothes don't you, well, mom doesn't need to know, if you agree to allow me help you experiment being in girls' clothes for the next couple of weeks of Christmas break." Julie explained.

"Ooo, ooo, let me help, I can help too!" jumped Amanda.

"Yes, Amanda is part of the deal too!" explained Julie.

I looked down in shame and nodded no to it.

"Awe don't you want to be pretty, look at you, you have a nice figure, in an alluring blue dress, and pretty colored shoes, hell you haven't even tried stockings, underwear, and a bra!" explained Amanda.

"Oh my God, I can give my brother boobs!" yelled Julie excitedly.

"Look, get this straight, you will do it, do my chores, be my very own life size Barbie and you are going to like being my baby sister for a few weeks! Or I will tell Mom, then tell all your friends at school how you like dresses and how you like to be rammed up the ass!" she commanded.

I had no choice but to agree.

"Don't worry," said Amanda comforting me, "we are going to take good care of you!"

"It won't be all day, just when I want, and when mom isn't around, and besides this will be fun! When we get through with you, you will be dancing in stilettos before me, ha ha ha ha ha!" Julie stated.

"Well, until tomorrow, play around with this get up you have on, then when mom leaves, the fun begins my new cute little sister", as Julie said in a baby talk tone.

"You are going to be so pretty, Jesse…hmmm…. Do you like Jesse, or would you like Jessica! Ha!" said Amanda.

"MMMMM, Jessica, Jessica " the girls taunted me. "Oh maybe", as Amanda picked up a teen magazine, "Brittany, Christina, nah, Jessica, like Jessica Simpson!"

I had nothing to say, but I was in the hands of my older sister who I once adored, now I feared. I was frustrated. But maybe this is what I needed, maybe I can stop if she just showed me how close I can be to being a girl.

"Well we'll have to see what tomorrow brings, and don't try to run off or I'll mom and your friends, now get out of those clothes, put back all of the things, and shower up before mom gets home—FREAK!" commanded Julie. "I am home and running things now" she said.

Mom came home and we all had dinner like nothing ever happened. Later that night, when mom was asleep, my sister jumped into my room and passed off a silk gown to me.

"Here, I want you to sleep in this tonight, I think you are going to like it, do it now, so I know you have it on", she said optimistically.

I got out of bed and slowly changed into the slip silk gown. It was cold and covered most of my body. It felt sensational against my body.

"You like that, most men love silk, and now you get to wear silk every night, sleep tight little sis', we are going to have so much fun tomorrow!", she said so happily.

And so I slept with a silk gown, and it gave me my first erection that I could not control. It was such an incredible experience; I could only imagine now what my sister had in store!

To be continued

  

  

  

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