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I Went On Vacation Dressed As A Girl

Personal Stories, Advice, and Support 332 People

    We Call Them Girl Trips

    We've gone on girl trips where I only bring womens clothes and shoes. To fill part of my desire to dress more often, I have women's clothes that blur the gender line. Tops, jeans, shorts, and shoes. I don't cross completely but am dressed in womens clothing the entire time...
    VickieBonne VickieBonne 41-45, M 20 Responses Jan 12, 2012

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    Early Days

    In late 70s,I spent my school holidays with my friend Billy and his mother Mrs P at a caravan site in the south of Scotland .Part of the deal was that we would work in the kitchen of the site cafe.It started OK and we washed dishes for two hours twice a day,then the owner came...
    paulapetticoat paulapetticoat 41-45 6 Responses Jan 27, 2011

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    Vacation With My Sister

    I posted this In a different group but thought it would be more appropriate here Hey everybody this is my 1st story on here and so i thought I would share this experience so me and my sister was going on a vacation to Florida but when we got of the plane the bag that had my...
    NickW1 NickW1 18-21, M 2 Responses Apr 29, 2013

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    At My Other Aunts House

    My older brother had gotten into a car crash out of state. A friend of my mother had offered to watch my younger siblings and I was to go to my Aunts home. My mother packed up the other siblings suitcases and sent them to her friends home. They had gone there because she had...
    great12345678910 great12345678910 22-25, M Jul 11, 2013

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    Girlie Trips!

    My wife & I have taken many vacation trips together...some short & others longer...in which I dressed entirely from skin out in feminine attire. We've found that my ladies slacks, a pretty top & suitable footwear do not place us in any jeopardy. It may raise eyebrows or bring...
    janusatv janusatv 61-65, T 2 Responses Feb 22, 2012

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    I was caught by my Aunt

    when I was 12 or 13. Shes only about 6 years older than me. I was dressed in her room in her things. She flipped out at first and tried to embarrass me out of it but her friends she invited over started to talk and comfort me. Finally she understood and started to help...
    sissyjolene sissyjolene 46-50, M 21 Responses Apr 3

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    Girls Vacation

    Still a teen and i been on vacations as a girl. Mom would lay out outfits and pack my suit case and only have one change of boy clothes. The rest was all girl clothes and the ones i was wearing. With my hair long and no showing adams apple, i pass as any girl. Always loved going...
    great12345678910 great12345678910 22-25, M 1 Response Jul 11, 2013

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    When You Least Expect It, You Get It

    i got all dressed up last week to go out shopping. i had on a short red gauge skirt, a red tank top and a black sweater.and sandles. i was not looking for any action, just shopping. i went into Tractor Supply and was looking at some tires for my trailer when this guy starts...
    closet36 closet36 61-65, T Apr 20, 2012

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    Being on vacation is the best time to be a girl

    24/7 for multiple days at a go.
    glassesfriendcy glassesfriendcy 26-30, T 4 Responses Sep 9

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    Wrong Luggage

    My mom told me and my brother we were goining to California.So we packed everything we would need for the trip. We got the the airport went through airport secuirty and I accidently grabbed the wrong luggage and went on the plane I went into the luggage to grab my ipod to listen...
    great12345678910 great12345678910 22-25, M Jul 11, 2013

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    Getting Air To My Body

    As some of you may know, when I was young my mother used to send me out to play wearing a girl's dress and no knickers. She said that I should get some air to my body. This became quite a regular thing when the weather was fine. Looking back I can now follow at least some of her...
    crikeymoses crikeymoses 70+ 2 Responses Dec 13, 2011

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    Drove A Crossdressing Friend To Virginia Dressed In Women's Clothes

    A crossdressing friend that I knew for a while, we exchanged some emails over a post on a web site called Life's A Draag a crossdressers forum (not on the internet any longer). We met in person and went out dressed shopping or to clubs. We did not have intimate relations though...
    deleted deleted 26-30 4 Responses Sep 25, 2011

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    A Little Later

    Some people have asked me to tell what happened at the wedding,so here goes........Neither Mrs P nor I told my parents about the fact that I had spent time during summer vacation dressed as a girl and working as a waitress,and when we got home everything went back to normal.Billy...
    paulapetticoat paulapetticoat 41-45 2 Responses Jan 25, 2012

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    Aunt Jane

    It was summer vacation and my parents had to go to Australia with work. So I stayed with my aunt Jane and my two girl cousins, Millie and Annie. Millie was 12 same age as me and Annie was 13. Millie the same height and weight to me. I was taking the bus to Washington where they...
    great12345678910 great12345678910 22-25, M 3 Responses Jun 2, 2013

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    A Week In The Prairies *not Done)

    It was after school for Spring Break and my Aunt Karen had asked if I could come up to Manitoba to visit her for the week. Her husband had gone on a business trip for 2 weeks and she needed some light work done around the house. My Aunt Karen lives with my cousins Samantha and...
    Jacklyn13 Jacklyn13 61-65, M 3 Responses May 2, 2012

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    I Love Being A Girl

    when i was born i was a boy, but i had and older brother,by 4 years. my father was an over the road trucker and was never home. my mother wanted a girl, not another son, so she raised me as a girl. from the day i was born all i knew was being a girl. i played with the girls and...
    closet36 closet36 61-65, T 3 Responses May 1, 2011

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    I Spent 2 Weeks As A Girl

    Well it was about a year ago and my gf offered me to spend the holiday with her at the time and her mum wasn't keen on the idea as I am almost 2 years older than her. She could get me somewhere to stay for a week but I had nowhere for the second week. Then she suggested the idea...
    deleted deleted 26-30 4 Responses Nov 21, 2010

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    Going To The Smoky Mountains As A Little Girl. . .

    I was a girl, part time at least, until around the age of 11 or so. My parents sent me to my grandmother for me to live as often as they could. This meant I spent my summer break from school with my grandma from a couple of days after the end of school until a few days before...
    ThomasCarroll ThomasCarroll 36-40 5 Responses Nov 30, 2013

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    At My Aunts House

         My older brother had gotten into a car crash out of state.   A friend of my mother had offered to watch my younger siblings and I was to go to my Aunts home. My mother packed up the other siblings suitcases and sent them to her friends...
    bobbie13 bobbie13 56-60, T 11 Responses Sep 8, 2010

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    More Stories?

    I wish there were more stories in this group.  I also wish I had a story to contribute.
    AFeminineGuy AFeminineGuy 41-45, M 2 Responses Jan 11, 2012

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    Sure Sounds Like Fun

    I'm not sure I could ever get up the nerve to do it. At least not alone. Maybe with another crossdresser or two. I've always been a different person when I put on female clothes, and it would really be fun to get away to a different place that way.
    RayanneA RayanneA 56-60, M 2 Responses Apr 16, 2012

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    Still Early Days

    Very gradually but very quickly my new friends not only accepted me as another girl,but recognizing that I only had my waitress uniform of a skirt and blouse,and one dress,helped me become more feminine by subtle touches,wearing bracelets or a necklace,or a silky scarf with my...
    paulapetticoat paulapetticoat 41-45 3 Responses Feb 2, 2011

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    A Sexy Weekend

    My wife planed a weekend away we booked a room in a hotel 100 mile from home. we packed and she said she would pick my clothes, she didn't pick any male clothes. I don't have any male undies or jeans or shorts. she added some of her tops and pink flip flops . she made sher the i...
    laciebottoms laciebottoms 56-60, T 8 Responses Apr 23, 2012

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    My Aunt Mary

    When I was thirteen my Aunt Mary called my mother and asked if I could spend a few weeks with her and my girl cousins, Connie and Wilma. My Uncle Pug was being deployed to Vietnam and she said she needed some help around the house. I loved my Aunt Mary. She ws extremely nice to...
    great12345678910 great12345678910 22-25, M Jul 11, 2013

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    Car Crash While Dressed

    I was all dressed up to the nines and was in down town Washington DC. going shopping. I was at a red light looking at the people walking by when i looked in the rear view mirrow and saw a big truck coming at me and not slowing down. Then he hit me so hard that the car shot...
    closet36 closet36 61-65, T Jun 4, 2013

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    Beaumont Society

    do great hotels weekends where you can dress stay in or go out but mainly you can be you dressed as girly as you like with all the other girls for the whole weekend
    christinemelody christinemelody 56-60, T Apr 30, 2013

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    Family Planning On "forcing" Me To Do This? :o

    My family is going to florida this june, andI have been noticing that my mom has bought a lot of new clothes. The clothes are my size though! One is a one piece bathing suite with an attached cover up like thing kind of like a short dress over the bathing suite that hangs down...
    AlexisKrasivyy AlexisKrasivyy 18-21, T 7 Responses Jun 11, 2011

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    Weekend

    I was working like a crazy person for 1 year and had accumulated enough vacation I had to take it or I was going to loose it, so I decided I was going to hit the beach and since everyone was busy, had no money or coudent go with me I decided I was going to take all my clothing...
    vsxmark vsxmark 22-25, M 1 Response Jul 18, 2012

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    I Went On A Cruse As A Girl By Myself.

    i have always wanted to take a cruse. so i booked the cruse as a girl, and i did not take 1 piece of male clothing with me, not even shorts. just skirts and dresses. everything was going great until i had to go through the metal detector at the airport. it went off. too much...
    closet36 closet36 61-65, T 11 Responses Apr 19, 2012

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    My Aunt Mary Part 2

    I had been at my Aunt Marys for a couple of weeks by now. I had pretty much gotten used to wearing my cousin Wilma's clothing. Everyother day I would either be wearing one of here short sets, a dress or one of her skirts. As you remember I was there to help my Aunt because my...
    great12345678910 great12345678910 22-25, M Jul 11, 2013

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    The Big Day

    I didn't think there was a great deal of interest in my earlier stories but have now had a few requests to complete the tale,so well......On the day of the wedding,Mrs P and I got up early with Billy staying in bed.His mother told him to make sure he got up soon,showered and...
    paulapetticoat paulapetticoat 41-45 2 Responses Jun 26, 2012

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