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I Lost A Bet And Had To Wear Girls Clothes

Personal Stories, Advice, and Support 143 People

    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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    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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    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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    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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    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 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 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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    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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    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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    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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    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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    Related Experiences

    Hi! I'm 13 y/o and I like to wear girl clothes. First time: It all begun when I was 8. My mom forgot her thong in the bathroom so I took the chance and tried them on. They felt...
    alexswe alexswe 13-15, M 4 Responses Jul 31

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    True....I remember when I wore my clothes but the day I tried girls clothes it feels so comfort to me....loving it
    jkmkjk jkmkjk 22-25 3 Responses Aug 7

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    yea girls clothes are just WOW when guys clothes are blah
    ashleysokolik ashleysokolik 13-15, F 5 Responses Aug 7

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    I love myself wearing men clothes! For example borrowing (or stealing lmao) a t-shirt or a hoodie and wearing it <3
    dropdeadwilma dropdeadwilma 13-15, F 10 Responses 1 day ago

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    It was the summer of 2013 i decided to spend the summer vacation at my friends house my friend only live with his mother and his two older sister Blair and Lisa his father left my...
    BoyGirlie BoyGirlie 18-21, M 1 Response Jul 31

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    I feel that I put on skit and bar and tight part I like it and feel that I not in the body I in I am a girl inside outside boy and I what to wear drees a blue drees make me hot in...
    jacobbarry12 jacobbarry12 13-15, M Aug 7

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    I'm sure most beginning crossdresser were all afraid of being seen dressed but wanted to be seen by someone. Sooner or later that desire will force us to stand by a window or...
    CdKimmi CdKimmi 61-65, M 1 Response Aug 15

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    I bond to my old clothes, they become an extension of me. It'll wear them until they're tattered. Tossing them out is like tossing out a part of me.
    Lifeisacaveat Lifeisacaveat 56-60, M 1 Response Aug 2

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    Fabulous date last night I felt so feminine.I decided to wear my new dress after thinking about wearing a pvc pencil skirt so I rang my sister up and she offered to do my hair...
    girlynicole girlynicole 36-40, T 3 Responses Aug 21

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    Today I'm wearing underwear that belonged to my friends girlfriend . Grey cotton g string white bra . They feel so good and just the thought that she had them on drives me insane...
    toesforme toesforme 36-40, M 6 Responses Aug 12

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    I just find them so comforting and exhilarating. As you can read in some of my other stories, it began with bras as a pre-teen and grew slowly over the years. Now that I live on...
    LockedDarius LockedDarius 26-30, M 2 Responses Aug 21

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    I will start this with the male misconception that woman have it easier the men in life. Females {F} & Males {M] wake up and get out of bed the same way, both feet on the floor but...
    CdKimmi CdKimmi 61-65, M 1 Response 1 day ago

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    Who doesn't?. Depend on the weather i have such a huge variety of clothing. Colorful to some extent i like to dress up in nice clothes i like to put together even if other disagree...
    NymNin NymNin 18-21, F Aug 4

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    Totally. Women's clothes are so much nicer and they fit and feel nicer. I love all the variety and styles.
    tiboi tiboi 22-25, M 2 Responses Aug 15

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    Love to be sat in a room with about 3 or 4 girls and me 2 be trying on loads of women's clothing and accessories even if it's just the once
    24chris24 24chris24 22-25, M 2 Responses Aug 21

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    Fashion industry doesn't thrive by the likes of me. Old, worn in clothing is my style. There's just no one in my life I am trying to impress by wearing something new :)
    Lifeisacaveat Lifeisacaveat 56-60, M Aug 2

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    If you will then give me links to what you will make me wear thanks
    Kyliethesissy Kyliethesissy 16-17, M Aug 6

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    My wife has me wearing matching satin Cacique bra and panties with black nylons, black flirty skirt, red top and my red 4" heels. Also all made up with a my brown curly wig and...
    nikkifemmdslave2 nikkifemmdslave2 36-40, M 4 Responses Aug 12

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    I wish my wife would let me wear women's long sleeve shirts to bed. I get so cold that I want one so badly.
    thestifmeister thestifmeister 22-25, M 2 Responses Aug 15

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    I'm building some new friendships with a couple of women and I had a wonderful time with them, just out talking around and outdoor table at a restaurant in town. Me in my tights...
    KatieTreat KatieTreat 51-55, T 8 Responses Aug 22

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    I am laying in bed feeling naughty wearing my Billabong tie side bandeau top costa blue scrunch butt bikini. Makes me happy and feels luxurious
    deleted deleted 26-30 1 Response Aug 10

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    Disclaimer: I left my digital camera card in the cottage, so I made use of my telephone for these images. Just so you recognize why some of them are a little bit blurry.The hiking...
    Rebekahumf Rebekahumf 31-35, M 1 Response 6 days ago

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    Our team of moderators has reviewed your photo, and found it to be in violation of our community guidelines. To see a complete list of EP Community Guidelines visit: EP Link...
    anrmilk4u anrmilk4u 36-40, F 4 Responses Jul 30

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    I look drees on tv and look so cute and at night all people in bead I hid drees colth girl in my room put it on I fell good and I what be a girl help me to be u and swap body to...
    jacobbarry12 jacobbarry12 13-15, M 3 Responses Aug 5

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    Yersterday I at the shore and I saw a hot sexy drees I what look hot and today but girl cloth I have some good
    jacobbarry12 jacobbarry12 13-15, M Aug 7

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    Me toi hornyhard I like to *** all the time I like ***
    chuck6004 chuck6004 51-55, M 1 Response Jul 30

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    Is there any one from the Sarasota/Bradenton Florida area please send me a letter would like to meet more people in my area
    estacie estacie 51-55, M 3 Responses Aug 3

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    When I stand on the bus, nobody could know that I am naked underneath my summer dress or skirt. When the winds play with the skirt and reveal my *** woke waiting outside. I love...
    Kirsebaera Kirsebaera 22-25, F 3 Responses Aug 3

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    Well my first adventure was going to be tonight but it turned out to be a wash. I got all dressed up and was going to go out, and walk down at the park by the bay and feel the...
    estacie estacie 51-55, M 2 Responses Aug 9

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    I have been dressing up in secret since the 6th grade. I would raid my mothers closet, dress up for a while, then put things back. I have always been straight (only attracted to...
    deleted deleted 26-30 1 Response Aug 13

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    finally ordered my breast forms they should be here by thrusday along with some other items i ordered. gonna try and make it out this weekend as Stacey and see how it goes wish...
    estacie estacie 51-55, M 6 Responses Aug 19

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    I didn't know it until later in life. When I was younger I used to borrow my mom and grandmothers pantyhose. From there it escalated to pantygirdles and panties. That was it...
    vanessacd5 vanessacd5 41-45 4 Responses Aug 22

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    Any guys out there hiding there secret
    ddavis16 ddavis16 18-21 Aug 18

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    I like these one. They feel good
    MaxSinner MaxSinner 31-35, M 3 Responses 5 days ago

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    I love wearing them! They are really comfortable, and hug your body so well, especially with their interesting fabrics. And of course the lower body freedom. I would not want to...
    Roccondil Roccondil 22-25, M 10 Responses Aug 1

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