Crossdress Vacation With Family.

i have always secretly loved crossdressing. my first name is Cole and my twin sister who looks almost identical to me is Sarah. i live with my mom because my dad died before i was born. i have shoulder length hair like my sister and i am only 7 years old at this moment.
So to start out, we were going on a vacation. i pack everything i need and as usual my sister overpacks. We are going to go to Disney Land and this is when it starts.
Mom: "Kids you done packing yet?"
Me: "i'm comming."
Sarah: "almost done just give me a minute."
a minute later my Sarah comes down in a pink shirt and skirt with her luggage. So we put our luggage into the back of our car and head off to the airport. when we arrive at the airport we put our stuff on the belt and head onto the plane.
When we land:

Mom: "come on Cole grab your stuff."
Me: "i can't find it."
Sarah: "he's probably missing it." comes over to help.
Mom: "you find it?"
Sarah: "Nope they lost his stuff."
Me: "How did they lose my stuff?"
Mom: "I'm going to have a word with these people."

We then go over to complain and they said that if they find it they will send it over to the hotel. and if they find it after we leave they will send it to our home. and if they dont they would compensate us.

Mom: "We need to get you some more clothes. you can't wear that for 2 weeks."
Sarah: "Why are all the stores closed here?"
Mom: " I don't know lets ask at the hotel."

at the hotel.

Mom: "excuse me, why are all the clothing stores closed?"
concierge: "There is a festival going on that no one seems to want to miss. so most of the stores are closed."

at our hotel room.

being 7 years old i'm crying cause i dont have any clothes.

Sarah: "Cole could wear some of my clothes. i have an extra swim suit and everything."
Mom: "Cole would you be alright with that?"
Me in a crying tone: "i don't care"

so then Sarah takes out a pair of pink floral panties and my mom puts them on me. she then gets a floral dress out as well and then i'm in that as well.

Me: "mom why do i have to wear this?"
Mom: "either that or naked your choice."
Me: "fine"

my mom then put a pink headband on me and put me infront of a mirror. i thought that i look just like my sister.

Mom: "So, What do you think?"
Me: "I look like Sarah."
Mom: "Sarah get your extra swim suit."
Sarah: "here he can have my yellow one."

it was a very bright yellow swimsuit. almost like her bright pink one that she loves so much.

mom then put it on me and i saw myself in the mirror. being young like this you couldn't see any of my boy parts.

Mom: "lets go."
Me: "Mom where are we going?"
Mom: "the hotel's pool."
Sarah: "YEAH swimming!"

so we swim for a while and go back to our room.

the next day i was in a yellow shirt with a pink skirt.
we went do disneyland that day.

i don't remember much about disneyland since that was the only time i was there and it has changed a lot since then. but we went on all the rides while there.

by the time we were about to return how we get a message that my bags have been found but they were sent to my house.

so the entire flight home i was in a pink shirt with a blue skirt and yellow flower panties. those were some of the best 2 weeks of my life.

nikki9000 nikki9000
18-21, F
7 Responses Feb 10, 2013

Great story! Thanks for sharing the story.

Great story. Sounds like fun

What did you do about using the bathroom and stuff?

That sounds like it was so nice and lucky to have happened

What a beautiful experience


Great story, Cole, and I guess you have the airline to thank ... though that is great that your mom and sister, Sarah, did to help. No wonder those were some of the best two weeks of your life.