Caught Trying On A Skirt By My Sister

I did cross dressing for a few years now, but never understood how girls wear the stuff. I was curious how girls wore those mini skirts, dresses, blouses, and whatever else. So I figured to try it when nobody was home.

So, my mom had to bring my sister to a softball game, and I had already wore her clothes during it quite a few times. So as soon as they left, I ran into her room and pulled out a black skirt 'ra-ra' style, about 3 inches above my knee. So I put it on, and it felt exhilarating. I was not nervous, knowing that they would be gone for about 2 hours. So I put it on, and then put a gauzy black blouse on. I went into her makeup kit and put on red lipstick, then felt good like always. But then I heard footsteps coming up the stairs after a while. I knew it was my sister, because she walks up the stairs loudly (her name is Natalie) so I tried to hide in the closet, but she walked through the door.

She stared at me, and there was silence in the room for about a minute. Then, she asked, "What are you doing in my clothes?" As being a boy I didn't want to say I loved wearing her clothes (which I didn't much, I did it to understand how they wore it), so I said, "I wanted to try on girly stuff to see how it feels." But in a very shaky voice. My legs were trembling, and she just smiled at me. She started laughing and said I looked cute and pretty, and that she didn't know she had a sister! I blushed, then rage filled me. I said, "What are you doing here, you should be at practice!" She said that she forgot her glove, so I felt embarrassed so much. She said she had to get going, wouldn't tell mom, and would take care of me later. "For now," she said, "take off all that stuff and get to bed. I will deal with you tomorrow." So she left, and the next day came. I didn't think that my sister would ever do this to me.

She said that if I wanted to dress like a girl, she would make me a girl. When mom went out on a business trip (gone for about a day) she told me to come in her room. She had a whole bunch of girly clothes layed out on her bed. "If you want to dress like a girl, I will show you how to BE a girl." She said in a loud voice. She giggled and grabbed me. She tied me to a chair and duck taped my mouth. First, she put a cinnamon colored wig on me, long, down to my shoulder blades. Then, she put pink blushings on my cheeks. Then pulled me out of the chair and took the duck tape off. She then grabbed me, flipped me onto her bed, and pulled my jeans off. She pulled my boxers off, and put pink flowery silky panties on me. At that point I was so scared of what else she would do. Then, Natalie pulled out a very short pink dress with a flowery pattern on it. She put it on me, then took my shirt off. She put on a bright pink blouse on me, then put very pink lipstick on me. She got me into her pink sandals, and laughed.

"There, take that you little brat!" She shouted. "Aaaahhh... I feel so... Girly..." I said in a shaky and low voice. "Good, you better. I gave you the perfect makeover to look like a gorgeous girl!" She wailed. Then she started to crack up laughing in a light laugh. She tied me up to the chair, and took about 20 pictures. She promised not to send them, but use them against me. Once that was all over, she told me to NEVER wear her stuff again. She made me take it off, but I couldn't, so she laughed and kicked me out of her room, looking like a girly girl, smelling like flowers. I felt SO embarrassed, but the panties felt pretty soft on me, so I decided I looked and felt so girly, I would stay in it to see what girls were like. But it got much worse after that.

A week later, my mom had to go out to another state for something for her work. She said she would be gone for a few days, and that my sister would watch us. So I felt pretty confident to have fun while she was gone. But as I was about to call a friend to go over, my sister, Natalie grabbed me and pulled me into her room. "Time for the ULTIMATE makeover!" She shouted. She put the same stuff on me, pink mini skirt, 3 inches above my knee, a pink blouse, cinnamon wig down to my shoulders and past, pink lipstick, all the same. But she decided it would be fun to take me outside of the house. She told me to go along with it and walk and talk like a girl or I would be in deep trouble, text my friends the pictures, and tell mom. I said in a very desperate voice, "Fine... Whatever you say to release me, no matter what." We walked about 2 miles to the mall. I felt so embarrassed with everybody watching us walk, but I think I looked like a real girl. I started walking funny, and my sisters pinched me and said to walk girly. So I had to move my hips side to side as I walked, and she giggled so hard she started to cry. I frowned, but kept on going. Then I had to talk in a high voice, so girly, I could have passed as a girl's voice. My sister said I looked very sexy hot and said I talked like a true girly girl. So we entered the mall.

As I walked in, there were hundreds of people with bags in their hands, running by. Nobody really stared at me, so I guess I really did look like a cute girl (according to my sister) so we went to the girls area, got our nails done, and bought panties, short skirts, dresses,  bras, and more. "Oh, I forgot!" My sister said out loud, with a few people staring. "Come with me into the girls room." She whispered. I went in, and she gave me a bra to wear. I put on the newly bought bra, and she stuffed it with tissue. Now I looked really like a girl. We walked around for a while, and went home.

"So, have you learned your lesson?" She asked. "Yeah, I guess I have." I said in a happy voice. "So, I could take this garbage off now?" I asked excitedly. "HA! You think you will get off THAT EASILY?! I will make you dress like this for the next year, when mom is out for at LEAST 4 hours. How does THAT SOUND?!" She shouted. "Ugh... What if I don't?" I asked nervously. "Well, lets see... If you don't want to, I will tell mom, and make her have you dress up like that to SCHOOL." She said happily. "Oh, jeez... Fine, as long as nobody sees me." So for the next year, whenever my mom went out, she made me dress all girly like she did before. But every time, it got more girly and girly. Then, she made me wear panties EVERY day for the next year, and every night when my mom went to bed, she had us play "dress up" to dress like a girl. But of course, I never stopped. :P

Well, that's my story. Comment if you think I should tell another one, because I have about 3 more. Also, tell me how it was. :) (My first story)

FishExplosion FishExplosion
18-21, M
20 Responses Oct 21, 2010

How old were you and how old was your sister when this happened?

I loved it, please post more !

How old were you when this happened

oh you have such a good sister. if it is possible sent us some pic

One of the best stories I've read on here.
Is it true?
Loved it, how old were you when this happened?

Please do tell more i loved it !! :)

Great story do tell more please.

Love it wish I had the same experience, I love being girly

tell more storys! add me!

very nice and long please more

Dude that's not even close as bad as what happened to me but if u want your sister to tell someone u better not tell someone

I wish my sister would dress me up like that again

i love ur story btw so could u make more n send me it 2 my profile plz thanx

OMG i love dressing up as a girl it seems so sexy

great story!! would love to be you rfriend!!

great story!! would love to be you rfriend!!

loved the story tell us more

P.S. I like the story keep them coming...Angie..xoxoxo

I could only wish to have had a sister old enough to have clothes that may have a chance to fit.<br />
I only had my mothers things,which made it pretty hap hazard at best...sigh..Angie.

OMG The same thing happened to me! My sister Holly did that too! I got caught wearing pink silk underwear and a bra. My sister did the same thing too! Although the panties felt pretty well each time