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I Lost A Bet And Had To Wear Girls Clothes

Personal Stories, Advice, and Support 143 People

    Don't Make Bets

    My girlfriend and I were board and decided to make bets for fun but it was anything but. She said we should fight to see and knowing that I would go easy and not try she kicked me in the balls and after a few painful moves she pinned me and now I lost so now she chose to turn me...
    Smat2331 Smat2331 16-17, M 1 Response Dec 7, 2012

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    At My Cousins In Maryland

    I was visiting my cousins, Jimmy and Caroline in Maryland, about 35 miles north of Baltimore. We had gone there to see my Grandfather as he was staying with my Aunt Margret as my grandmother had passed away. It was raining outside in early June, school was out for the summer...
    Melodie13 Melodie13 61-65, M 7 Responses Mar 3, 2012

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    Mind

    The Mind when guided by the worldly intellect, guided by the previous spiritually inclined person who got inspiration from the good thoughts dominated in the cosmos. Thus it requires an infinite- passion, infinite wisdom, infinite and untiring selfless work for the betterment of...
    sowmyabeautiful sowmyabeautiful 22-25 Oct 24, 2012

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    I Recently Lost A Bet And Have To Dress Totally As A Woman...For Over A Year!

    Back during Basketball Season My Sister and I made a bet on which team would win. I was so sure that the Oklahoma Thunder would win that I got into a bet with Sis that stated the loser of the bet had to do whatever the winner said for a whole month. As the series began Sis and I...
    1trj 1trj 41-45, M 23 Responses Jan 4, 2013

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    My Cousins

    I was visiting my cousins, Jimmy and Caroline in Maryland, about 35 miles north of Baltimore. We had gone there to see my Grandfather as he was staying with my Aunt Margret as my grandmother had passed away. It was raining outside in early June, school was out for the summer and...
    great12345678910 great12345678910 22-25, M Jul 11, 2013

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    Lost A Bet And Dressed As A Girl

    Written on January 4th, 2013 Back during Basketball Season My Sister and I made a bet on which team would win. I was so sure that the Oklahoma Thunder would win that I got into a bet with Sis that stated the loser of the bet had to do whatever the winner said for a whole month...
    great12345678910 great12345678910 22-25, M 1 Response Jul 11, 2013

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    Wearing Panties

    My wife knows I wear panties and she loves seeing me wearing panties. Satin panties are both mine and my wifes favorite panties. My wife and I enjoy being playful so some bets we have made is if I loose I have to wear panties to get the mail, or to change the sprinkler, fun stuff...
    pantiescouple pantiescouple 26-30 Sep 10, 2012

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    Lost A Bet To My Older Sister

    Alright one day me and my sister were really bored and my sister asked me if I wanted to do a bet so I said yeah and asked what do u want to bet then she says who ever can hold their breath longer under water so we got our bathing suits on and went into our pool then I thought I...
    Coolguy24 Coolguy24 13-15, M 4 Responses Aug 27, 2012

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    I Lost A Bet To My Older Sister

    Alright one day me and my sister were really bored and my sister asked me if I wanted to do a bet so I said yeah and asked what do u want to bet then she says who ever can hold their breath longer under water so we got our bathing suits on and went into our pool then I thought I...
    great12345678910 great12345678910 22-25, M Jul 11, 2013

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    The Betting Dress

    My name is Patrick and I am going on a trip to visit my cousins for the week. I woke up in the morning has my mom was yellinng for me. I looked at the time and we were suppose to be leaving, so I jump out of bed and got dressed. I didn't care about going because I had only girl...
    great12345678910 great12345678910 22-25, M 1 Response Jul 11, 2013

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    The Betting Dress

    My name is Patrick and I am going on a trip to visit my cousins for the week. I woke up in the morning has my mom was yellinng for me. I looked at the time and we were suppose to be leaving, so I jump out of bed and got dressed. I didn't care about going because I had only girl...
    Jacklyn13 Jacklyn13 61-65, M 7 Responses May 1, 2012

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    Makeup Bet

    I made a bet with my sister that I could beat her in a race around my block the if I lost she got to put makeup all over my face everyday for a month if she lost I got to shave her head I lost so the first day she did the my makeup then she said you look like a girl why not...
    Flash123456 Flash123456 22-25, M Oct 15, 2013

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    The Sleepover

    It all started when I was invited to a girls sleepover. There was four girls and also my girlfriend. My girlfriend was properr fit. She had brown longhair and brown eyes. Anyway my mom was driving to the sleepover. It started at 2 and ended at 2 the next day. She was saying that...
    great12345678910 great12345678910 22-25, M 3 Responses Jun 1, 2013

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    Related Experiences

    I love to wear girls clothes. I feel so good in them
    Harryharry123 Harryharry123 22-25, M Oct 14

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    Well I'm a girl so yeah. I'm a "girly girl" for sure so I love it!
    gardengirl17 gardengirl17 22-25, F 1 Response Oct 14

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    I want to see cute pics of this add me
    Masterlicks Masterlicks 31-35, M 1 Response Oct 15

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    When I come home from high school my parents come home late from work everyday I always go into my mums room and wear her clothes. I simply love wearing girls clothes because they...
    girlyliam17 girlyliam17 16-17, M 4 Responses Oct 5

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    i really do think girls clothes are better than boys as from a male point of view i just look at ladies skirts, dresses, coats, etc and think to myself i want to be wearing them as...
    GirlyAndrea1987 GirlyAndrea1987 26-30, M 4 Responses Oct 3

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    My wife knows that I love for her to wear revealing clothes in public, and although she's not thrilled with the idea, she will accommodate my desires, provided that it is a safe...
    celtics11 celtics11 41-45 2 Responses 1 day ago

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    I am a guy who loves wearing girls knickers and would love to talk to any girls that like guys wearing knickers
    Knickersboy14 Knickersboy14 18-21, M Sep 29

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    I love wearing womans clothes
    mickjag mickjag 66-70, T 1 Response Oct 16

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    I love to wear girls underwear. They are so sexy and that makes me feel good about myself
    Harryharry123 Harryharry123 22-25, M Oct 11

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    I always felt so jealous when I saw little girls wearing what I should have been wearing. I always wanted to wear dresses and frocks and skirts and nighties. I loved twirling in...
    Iamsasha Iamsasha 18-21, F 1 day ago

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    Last night, three of my friends and I went shopping at the mall. I, of course, wore my spandex pants, which the girls are use to. Also one of the girls also wore her spandex pamts...
    swimguy0812 swimguy0812 22-25, M 1 Response Oct 4

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    I'm not gunna lie. But girls do have wider clothes variety:D
    B2ST B2ST 16-17, M 1 Response Oct 4

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    Since I am 12 I wear swimsuits and I love it ! I started with my mom's one piece swimsuit which is verry tight and I felt incredibly good on it. Since, I bought two one piece...
    loveonepieceswimsuit loveonepieceswimsuit 18-21, M 1 Response Oct 13

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    It started a few months ago when I jokely put on a pair of my girlfriend's panties in bed. It slowly developed into me getting my own pair to me wearing other girl clothes. Today I...
    Csrummell Csrummell 18-21 Oct 10

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    my aunt was out at the doctors so i thought what a great time for me to dress for a while.i showered and shaved my whole body,then put on my black panties,black bra,my black cami...
    SISSYGUYMARIGAIL SISSYGUYMARIGAIL 46-50, M 1 Response 3 days ago

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    That would be a ultimate dream come true, just to be sat in a room with a few girls having a glass of wine and a chat, and trying on lingerie and clothes, and sharing opinions...
    xXSamanthaCDXx xXSamanthaCDXx 31-35, M 6 Responses Oct 7

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    What am I wearing today? I have purple toenails from my last pedicure. I just painted my fingers with Hard as Nails Cold as Ice. Is a barely there color that adds a wonderful sheen...
    Sharon03 Sharon03 56-60 3 Responses Oct 14

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    Yesterday my wife and I went and had a mani pedi together. She was okay with me getting my toes painted but would only allow clear coat on my fingers. They look so nice and i am so...
    Sharon03 Sharon03 56-60 3 Responses Oct 4

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    Due to my gender I prefer female clothes...
    ColourfulDreams ColourfulDreams 13-15, F 2 Responses Oct 5

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    Well let's be honest. There's only so much you can do with a shirt and pants!
    picklebobble picklebobble 46-50, M Oct 3

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    I always wanted my sister or someone to give me the most girly makeover anyone has ever seen so girly that people actually think I'm a girl I'm talking about make up,wig,bra...
    danny27619 danny27619 13-15, T 2 Responses Oct 4

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    I am an all star cheerleader and my friend Megan got me into it and she new I wanted to be a girl so she suggested I join as a girl, so I did and most of my teammates dont know my...
    Jaidenrachael Jaidenrachael 13-15, T 3 Responses 4 days ago

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    I haven't worn pink in ages. So today when I found my pinkish tie dye and pink shorts and put them on I went "woah. I look strange." :D
    SlowlyDrifting SlowlyDrifting 13-15, F 2 Responses Sep 29

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    oops :)
    katjalove katjalove 18-21, F 17 Responses Sep 29

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    airports n trainstations. love them!!!
    katjalove katjalove 18-21, F 16 Responses Sep 30

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    My wife likes 2 watch me dress up like a lady and take me out in public
    lookingforlotsoffun lookingforlotsoffun 18-21, M 1 Response Oct 4

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    Makes me look slim and pretty yes please
    ColourfulDreams ColourfulDreams 13-15, F 3 Responses Oct 16

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    When I was younger I used to steal my older sisters' clothes one was ten years older the other six years older than me. Until I was caught and got the belt and made ashamed by my...
    Hiddensissy69 Hiddensissy69 26-30, M 4 Responses Oct 1

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    Ok guys so hey first off, I wanna say that english isn't my mother language, but any way so yeah, Im a man that like to wear tights, I just wanna say, tights are the only women...
    pvpvohtgt123 pvpvohtgt123 31-35, M Sep 30

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    I found this on the internet - Hope it helps someone. 5 stages of grief - how it applies to infidelity Posting from another site. This will help you understand that the...
    NOWHealing NOWHealing 61-65, F 6 days ago

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    Ever since I was a little boy, around five. I was extremely curious, and had a lot of questions about girls. So one day during Pre Kindergarten. It was nap time. Every one else...
    GoldenDragon13 GoldenDragon13 13-15, M 4 Responses 1 day ago

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    when I was about 8 years old I invented a dress up game the rules were very simple- you had to bring a box of your clothing to play when everyone who wanted to play was...
    strawberrybutterfly strawberrybutterfly 13-15, M 2 Responses Oct 9

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    A few years back I tried dating websites to get someone intrested in me. My profile pic was not a nude or rude one, It was a good pic of me wearing good clothes. I tried several...
    Niko864 Niko864 41-45, M 1 Response Oct 4

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    I had to go out to the bank to make a deposit and get some gas. I really wanted to change into girl clothes to do that. But I waited until after I pumped the gas before I put on my...
    Sharon03 Sharon03 56-60 2 Responses 2 days ago

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    (i go to a boarding school)me and my friend were betting on the world cup semi finals. i bet for brazil. i lost i had to get naked and stay naked for the next three weeks(even if...
    alex2789 alex2789 18-21, F 1 Response 5 days ago

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