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I Lost A Bet And Had To Wear Girls Clothes

Personal Stories, Advice, and Support 139 People

    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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    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 8 Responses Mar 3, 2012

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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 Jul 11, 2013

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    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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    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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    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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    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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    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 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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    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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    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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    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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    Related Experiences

    Ever since I was 12 or 13 I've been cross dressing in secret. My mother caught me once when I was about 13 or 14. She was okay with it and asked me if I liked cross dressing. I...
    masspink masspink 18-21, M 3 Responses Jul 2

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    I've fantasized about wearing a pretty dress, makeup and cute shoes of some sort. Not sure what and I'm totally not qualified -- but the net is that I'd like to "be" the lady...
    bispike bispike 51-55, M 2 Responses Jul 4

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    Everyday that goes by I just want to say it! I want to shout it, but I don't, my parents would never understand and it kills me, I don't know what they would think, when I came out...
    thetimekeeper92 thetimekeeper92 22-25, M 3 Responses Jul 4

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    Hey I am new to wearing girls underwear and I must say I feel like a new person. The choices out there are incredible. My favourites are thongs and boyshorts. They are so much...
    knickersguy knickersguy 22-25, M 6 Responses Jul 7

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    Huh. You would think that there would me a lot more girls in this group. I look down the stories briefly and it's only boys and transgenders. Did I not notice that this was a...
    InternationalDarkness InternationalDarkness 13-15, F 2 Responses 4 days ago

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    I like to record every day I wear girls underwear by taking a photo of them
    knickersguy knickersguy 22-25, M 1 Response Jul 18

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    I love wearing girls pants it makes me feel like a girl, i wanna be a tranny
    manny67890 manny67890 16-17, M 2 Responses Jul 20

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    I can't stop myself from wanting to be a girl sometimes. I do believe I should have been born a girl, I truly feel that because this part of me gets so excited when wearing women's...
    Shadowhunter23 Shadowhunter23 18-21, M 6 Responses Jul 17

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    Cleaning out the closet IIAfter the wife left for work, I went and pulled out my oldest trash bag full of clothes and heels and then went and took a shower. I figured I better run...
    jamie50 jamie50 51-55 8 Responses Jul 4

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    I have far more female clothes than male clothes. I look forward to the day when I only have female clothes to wear. I find them so much more comfortable. There is so much more...
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 2 Responses Jul 3

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    One of my fondest memories was that of telling a friend I had to work.....when I did not, had to stay the nite at his house. Well, when the family left.....I put on his mother's...
    susanwarfie susanwarfie 41-45, M 2 Responses Jul 17

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    Reciently I came out of the closet after 30 years of hiding my love for wearing womens clothing. I had told my wife and she is taking it real good, what a trooper she is. This past...
    estacie estacie 51-55, M 11 Responses Jul 21

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    I love wearing women's clothes. I just feel so right. The problem is that my body type doesn't fit this obsession. I seriously sometimes feel like I should be a girl.
    c455muscle c455muscle 22-25, M 9 Responses 6 days ago

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    Cleaning Out the Closet I have been cross dressing for many many years and have acquired a collection big enough to fill a walk in closet. Some of the items I have date all the way...
    jamie50 jamie50 51-55 5 Responses Jul 3

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    I mostly wear thongs but love all styles of girls underwear. Sexy french knickers or a thong feel so great when you wear. My photos are open for anyone to view. You dont need to...
    knickersguy knickersguy 22-25, M 4 Responses 3 days ago

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    Now a days am wearing women's used nighties during nights and day time also I am wearing them under my pant and shirt
    lingarielover lingarielover 31-35, M 1 Response Jul 8

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    Bigger and better picture of what I just picked up and I LOVE IT!!!!
    wtbwoman wtbwoman 41-45 5 Responses Jul 8

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    Today I am wearing a dress to work... Well OK it is a mini dress under my "man" clothing. But how I wish I didn't need to wear the slacks... Also question for you all. I love lace...
    str8CD str8CD 36-40, M 7 Responses Jul 15

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    Love shopping for them for sure. I wear panties daily, and I have a few items of women's clothing I wear out in public. Makes me feel cute and sexy!!
    islands115 islands115 46-50, M 2 Responses 18 hrs ago

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    I most loved putting on the clothes of my friends' mothers
    susanwarfie susanwarfie 41-45, M 2 Responses Jul 17

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    Once I found my way to her bedroom......there really was no stopping me......could not wait to try on her clothes again.......could not stop me
    susanwarfie susanwarfie 41-45, M 2 Responses Jul 17

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    What happens when i wear jeans that dont fit me
    BigFatNick BigFatNick 13-15, M 1 Response Jul 14

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    I can stop to wear mycrox-d lingerie
    kamilatv kamilatv 46-50, M 2 Responses Jul 18

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    I'm wearing purple bikini style panties, black and white yoga shorts, cheetah bra, and a black tank top to bed 😏😍
    sammixdress sammixdress 18-21, M 3 Responses 3 days ago

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    Me toi hornyhard I like to *** all the time I like ***
    chuck6004 chuck6004 51-55, M 25 mins ago

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    Hello,my name is jacob but i like to go by zoey. I have spent the last seventeen years of my life alone because I am a girly-boy. Now I have the Internet and sites like this...
    zoey764 zoey764 18-21 a week ago

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    Hello,my name is jacob but i like to go by zoey. I have spent the last seventeen years of my life alone because I am a girly-boy. Now I have the Internet and sites like this...
    zoey764 zoey764 18-21 2 Responses a week ago

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    So a couple of months ago I told my sister I wanna crossdress ( she thinks this is my first time curiosity) she said she'd help me dress when she came home for the summer... Well...
    Marissatgsissy Marissatgsissy 18-21, T 2 Responses 3 days ago

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    I would love to own this, it is not offered at store pick up and I can not have it shipped to my home!!! I LOVE THIS SOOOOOOOOOOO MUCH!!!
    wtbwoman wtbwoman 41-45 6 Responses Jun 30

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    This is the back of what I posted a few days ago, I think the back is even more sexier than the front and so want this so bad, I LOVE IT soooooooooooooooooo much and want it really...
    wtbwoman wtbwoman 41-45 5 Responses Jul 2

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    Who doesn't love panties up on your junk!
    understateproject understateproject 36-40, M 1 Response Jul 3

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    I need sex bad! Can any one help me!
    understateproject understateproject 36-40, M 1 Response Jul 3

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    So just recently i got a few new pairs of Victorias Secret Yoga Pants xD one is all black and has the words pink in silver letters. The other two are both pink with the word pink...
    pantyboy94 pantyboy94 18-21, M 5 Responses Jul 3

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    I now own only womens knickers, womens jeans and womens shoes, also have tees and blouses
    fanniannii fanniannii 41-45, M Jul 8

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    This is what I bought because they did have store pick up!!! LOVE IT almost as much as my previous post!!!
    wtbwoman wtbwoman 41-45 2 Responses Jul 8

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