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My Brother/sister

This did not happen to me but I have a similar story that happened earlier this year I have a brother that is only  1 year younger than me I am 15 so he is 14.One friday night I was getting up to go get me something to drink it was around 12:00 and I thought I would go check on him.When I opened the door to my surprise he was sleeping in my lingerie I took a picture and woke him up and he started crying.Once I finally calmed him down I said I would not tell our parents under I condition. The condition was I would not tell if in the morning he would be my little sister for the rest of the day and he said OK!! I was so exited I was Finally going to have a little Sis I was so exited I   didn't even  go back to sleep after I got my water I just went in my room and though what I was going to have him do. When the sun came up I woke him up we went downstairs and our parent said they were leaving for the WEEK FOR 7 WHOLE DAYS. So guess what I did I said I changed my mind and would tell unless he was my Sis for 24/7 and he still said OK!! So after our parents left I took him up to the bathroom and told him to put something on his body and get in the shower and wash it off. When he saw the hair coming off his body he got scared and he calmed down after I told him it was supposed to do that.  After all the hair was off I gave him my shampoo,conditioner and soap when he got out I gave him a pink towel and told him to put it around him like I put my towel around me and gave him another pink towel and told him to put his hair in it which is LONG after he blow dried it. It was about 20 min after it was almost dry but before he took the towels off I gave him a rag and dry off his face,hands and feet I found what I was looking for in my bathroom. When I went back in I told him to be still and let me do what I want since that was the agreement we made he said OK I pulled my cart FULL of makeup,fingernail polish and toenail polish when I looked at the fingernails and toenails they were long like mine so I was going to have fun. I put some DARK PINK SPARKLY lipstick,mascara,blush,eyeliner and the other stuff on him I found some purple fingernail polish and toenail polish and put that on him and painted a little pink hart on them after I filed them. He was REALLY starting to 1ook like a SHE now. We then went to my closet and found this pink sparkly dress and put it on the bed in the draws I found a matching set of pink bra and panties and told him to close his eyes I put a pad in the panties so it was not so noticeable that SHE was actually a he  and I stuffed the bra so he  would look like a real girl I put them on him and he opened his eyes he was shocked he started looking like a real girl I told him to lift his arms and I put the dress on him and he sat down and I put him in some pantyhose and 5 in high heels he walk in them pretty well to. Now all was left was the hair I had him have bangs  and put the back in a ponytail. It was then of walking to the mall which is around 2 blocks away I had him go shopping with me and bought him a pink purse then we met a guy in my class who is HOT and his brother the same age as mine he said who is this I said that he was my sister Jamie(his real name is James) and he said his brother thought my "sister" was EXTREMELY HOT and wanted to go on a date with "her" but said that he wanted to go on a double date with is brother so his brother asked ME OUT!! I said YES without giving it a second thought it was all set up for the next day we would go eat then to the movies after they left I told my "sister" that was the least of "her" worries I then told him to follow me "she" didn't know where we were going I told him to set down in a chair while I go talk to a "friends" the next thing "she" knew was there was two cold feelings on his ears then a stinging felling "she" didn't know "she" just got "her" ears pierced we then went to the hair place and got "her" a perm  and bangs that go over one eye. We went to the bathroom because "she" had to pee "she" was about to go in the men's I said no and pulled "her" in the woman's she
Went to a stall and started to pee I said girls don't pee standing up they seat down she then pulled down the panties and sat down on the toilet I told her don't forget to wipe she said OK I went to the other stall and went to pee we got done and went home to sleep after I told her to go get in the tub 

day 2 
We was getting ready for our date today she had a purple dress. We got to the food place and met them there  then we went a watched a movie this continued for the next 5 days and both of us got really close to our new boyfriends  we got home I told her to get her guy cloths on and SHE said NO I knew I was going to get in trouble. My sister then said she would not tell our parents that I had her dress up and said she will tell them that it was her choice I said OK. Sure enough that's what she told them my mom wasn't so happy but my dad said he always wanted another daughter so now my sister will get changed into a real girl when she can so she can continue her relationship with Daniel. Now we go out shopping everyday it is so much fun to have a Sis I love my little sis
Me and Dave are still together I don't have the heart to tell them the truth but it won't matter in the future I guess. 
123kellyw123 123kellyw123 18-21, F 11 Responses Dec 5, 2011

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Ooooh just a beautiful story. I guess lot of boys do like to dress up as girl. As I am now girl with small boy thing dress nearly 100%. Beautiful to be girl.

What happened with your brothers date. are they still dating and does his date know he is really a boy.

Yes they still are darting he has recently done "the big change" and the boy never knew what he was they also one most likely to get married award and prom queen/king of there class :) :)

WTF

Would you give some picture of your sister?

My sister has been a great support to me over the years.

Can you do the same for me plz i am 17 male but i would love to be like your sis in a way plzz tell me what you did

Can you do the same for me plz i am 17 but i would love to be like your sis in a way plzz

Can you do the same for me plz i am 17 but i would love to be like your bro

Can you do the same for me plz

What a great story. and now you two have bonded in a way i bet you never thought. You just may be the best big sister ever.

That was possibly the coolest/touching story I've read on here.

It is great that you helped your brother to quit hiding his feminine side. Also with getting your parents to allow him to dress further as well. I am sure he loves all you have done for him. There are a lot of boys who would love to have their sisters dressed them and treat them as any other girl. I'd bet even some boys in your classes at school go home and slip into some of their sisters or moms clothing. Maybe you and your girlfriends can start dressing other boys from your school as well.