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I Lost A Bet And Had To Wear Girls Clothes

Personal Stories, Advice, and Support 143 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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    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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    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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    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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    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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    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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    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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    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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    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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    Related Experiences

    Ok I was just playing a game of rugby then 3 girls come up and say you want to bet and I say yes.so the bet is if my team wins I can do whatever I want but if they win well they...
    Dryraxyes Dryraxyes 13-15, M 4 days ago

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    Can a women try to talk to my wife about me wearing girls clothes?
    thestifmeister thestifmeister 22-25, M 4 Responses Sep 2

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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 16-17, F 10 Responses Aug 29

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    I remember the first time I experienced the feel of a girls 2 piece swimsuit. A girlfriend of mine left hers behind in our car when I was about 15. I just could not resist. The...
    wet2wet wet2wet 51-55 5 Responses Sep 9

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    This was not always true for me. In fact in the beginning it would have been one of the scariest of ideas for cross dressing me. Having lived for so long in fear of being...
    cdsubalice cdsubalice 56-60, M 4 Responses Sep 4

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    Panties, thongs, jeans, t-shirts. With my slight build I finding women's clothes fit better and more comfortable. Also more fun it wear. Sexy!
    NaziWarSurplus1945 NaziWarSurplus1945 51-55, M 4 days ago

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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, F 3 Responses Aug 21

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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 Aug 29

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    I love when women wear slightly or very revealing clothing, flaunting their figure and assets ;) But what i do not get is this. 1. Women are proud to be seen in a bikini yet freak...
    Anth9012 Anth9012 22-25, M 4 days ago

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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 3 Responses Aug 21

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    My favorite kind of clothes is whatever reveals the most cleavage on top, usually spaghetti strap. Then an inch or two of midriff and a short skirt or short shorts. I don't mind...
    YellowGirl225 YellowGirl225 22-25, F 18 Responses 5 days ago

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    So I got out my stash and was about to begin dressing but I fell asleep. I woke up this morning and realised I forgot to lock the door with all my clothes layed put in the floor.
    sissylaura09 sissylaura09 16-17, M 1 Response 2 days ago

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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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    Well! Friday night, I made my first night out fully dressed up and it was great, I took a walk down on the baywalk and walked out on the pier, then took a ride down to the jetty...
    estacie estacie 51-55, M 3 Responses Sep 1

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    Went to work yesterday dressed Felt great walking into the office in a skirt and tights.Most people accept me as a woman apart from old bag who made nasty comments. (I put it down...
    girlynicole girlynicole 36-40, F 9 Responses 4 days ago

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    I often buy pantygirdles on-line and love to wear them under very tight slacks
    kayleena kayleena 56-60, T Sep 2

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    I want a girl to force me to dress as a ballerina and take me out. Then take me home and teach me ballet.
    lovepink1998 lovepink1998 18-21, M 3 Responses Sep 1

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    I have just started writing a new blog chronicling the slow feminization and sissification of my partner by myself. This blog is not a work of fiction, nor is it in any way the...
    deleted deleted 26-30 2 Responses Sep 5

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    i would love the idea of a group of women having me model different girly outfits for them
    girlyAndrea1987 girlyAndrea1987 26-30, M 2 Responses 20 hrs ago

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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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    Partner at work leggings are on till 6 ish b4 I pick her up
    24chris24 24chris24 22-25, M Sep 4

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    i went downstairs to go outside to smoke,i thought my aunt was asleep in her room.im out smoking when i see the front room light come on.i start to get real nervous,then the front...
    SISSYGUYMARIGAIL SISSYGUYMARIGAIL 46-50, M 3 Responses Sep 9

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    it gives me thrills feeling exposed...
    katjalove katjalove 18-21, F 15 Responses Sep 10

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    I love when guys stare at my big *** in my tight dresses!
    Milfnificent Milfnificent 31-35, F 2 Responses 6 days ago

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    Just to the extent of being barely legal! :D
    PoojaTimberlake PoojaTimberlake 18-21, F 9 Responses 3 days ago

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    katjalove katjalove 18-21, F 7 Responses 3 days ago

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    Real **** though. Movie time. 😍
    haleyhaley haleyhaley 18-21, F 1 Response 11 hrs ago

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    I like these one. They feel good
    MaxSinner MaxSinner 31-35, M 3 Responses Aug 25

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    2 weeks ago, my mother had went on holiday with her boyfriend. So I had to stay at my cousins for a whole 2 weeks, everything was normal there until I overheard my cousin (15) on...
    Anddyyy Anddyyy 16-17, M 1 Response 4 days ago

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    I had an ex-gf and she broke my heart. She was everything to me. She was a Texan Mexican gorgeous chick and I was just an Asian New Yorker who never fell in love with anyone before...
    Awu0225 Awu0225 22-25, F 7 Responses Sep 7

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    When i was 14 i didnt really have any luck with guys. I was really shy. I figured i would have better luck with girls. There was a girl in my class that was cute and we became...
    Sierra1993 Sierra1993 18-21, F 1 Response 3 days ago

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    hehehe you wouldn't believe this...but look down at the story I wrote on August 14th. I'm still wearing those clothes!!!! Still! That is 23 days without changing clothes! It is...
    TotTotTotTot TotTotTotTot 18-21, F 2 Responses Sep 6

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    I love to treat myself and wear girls knickers from time to time. I have a couple of teenage lovers (17yo to 19yo) and I always get them to leave their knickers here as a treat for...
    spankwire spankwire 46-50, M 2 Responses Sep 1

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    Um wtf a man should be manly unless he's fully transsexual or should I say she...he should be wearing the clothes for him...just my opinion
    xlovelybutterflyx xlovelybutterflyx 18-21, F 2 Responses Aug 27

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