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I Wear Little Boy Underwear

Personal Stories, Advice, and Support 45 People

    Boys Underpants

    I've always been obsessed with underwear ever since I was about 9 years old, I now own in excess of two hundred pairs and that's just male underwear, it doesn't include women's, girls, boys or fetish! Recently I was told to wear some little girls panties (Flickr dare thing) I...
    sazzer1 sazzer1 36-40, M 1 Response Jul 29, 2013

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    i wish i had gone through petticoating as a little boy as it would of been good to be dressed up in petticoats
    GirlyAndrea1987 GirlyAndrea1987 26-30, M 1 Response Sep 27

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    [Photo] I'm wearing them now, just going to go to the shops and no one will realise.
    SirEvilJebus SirEvilJebus 31-35, M 3 Responses Oct 11

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    I wanna touch them and be touched by them. I wanna suck their lil peepees
    diaperedsammy diaperedsammy 18-21, M 2 Responses Oct 2

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    okay so its a new school year im a freshman in high school and i go to a private school 60 kids and 8 kids in my class and should i wear little kids underwear under my boxers let...
    Mike12322xx Mike12322xx 13-15, M 2 Responses Sep 28

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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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    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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    Haha no undies... Except I had a little boy look up my skirt once. Awkwaaard...
    creativecat1 creativecat1 18-21, F 6 Responses Oct 15

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    I wear bra and underwear! :) !
    brookmay brookmay 18-21, F 4 Responses Oct 2

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    I am a guy who likes wearing women's underwear all the time
    Ajrbruleieneu Ajrbruleieneu 22-25 1 Response Oct 14

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    i would of loved the idea of having a mum putting me through petticoat discipline as a little boy, making me wear dresses & petticoats. perhaps modern day mums should start it...
    GirlyAndrea1987 GirlyAndrea1987 26-30, M 1 Response Oct 16

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    My heart is aching. My boyfriend was sentenced to 3 years in Prison. They took him away from me yesterday. I'm not sure how to react, where to turn. Our story is a bit different...
    nukeemhigh nukeemhigh 22-25, F 1 Response 1 hr ago

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    I always liked the feeling of going commando, but since I thought my parents disapproved, I only did it when I wouldn't be caught. One place I wouldn't be caught was away at...
    Triangulate Triangulate 22-25, M Oct 11

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    I always liked the feeling of going commando, but since I thought my parents disapproved, I only did it when I wouldn't be caught. One place I wouldn't be caught was away at...
    Triangulate Triangulate 22-25, M Oct 11

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    Once, when I was six, I was at the house of a friend my age. He and I were hanging out unsupervised in his basement. Earlier that year, I had seen two girls my age remove their...
    Triangulate Triangulate 22-25, M Oct 10

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    Once, when I was six, I was at the house of a friend my age. He and I were hanging out unsupervised in his basement. Earlier that year, I had seen two girls my age remove their...
    Triangulate Triangulate 22-25, M 1 Response Oct 10

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    I always liked the feeling of not wearing underwear, also known as free-balling or going commando. Since I thought my parents disapproved of my free-balling, I only did it when I...
    Triangulate Triangulate 22-25, M 1 Response Oct 11

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    I always liked the feeling of not wearing underwear, also known as free-balling or going commando. Since I thought my parents disapproved of my free-balling, I only did it when I...
    Triangulate Triangulate 22-25, M Oct 11

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    There are so many kinds of silk underwear for men and women in the online market these days that are very useful and compatible for those individuals who want to stay sexy and...
    edr567 edr567 26-30, M Oct 15

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    None of my friends or family have any idea but when I get home at night and if I have no prior plans the first thing I do is shower shave or wax if I need it then spend a glorious...
    Jimhes Jimhes 31-35, M 6 Responses Sep 30

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    ****BARE-LY THERE**** 1. With dresses. Decent, knee-length to ankle length ones. Not with mini dresses. Don't want any accidental flashing or advertising to the world that i'm...
    CandyxCane CandyxCane 36-40, F 16 Responses Oct 9

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    I was shopping online and came across a sale at Spanx. So I called my wife over and picked out a few items for her. She knows that I don't like mens underwear because of the pouch...
    LatentXD LatentXD 56-60, M 7 Responses Sep 28

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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 22 hrs ago

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    My apologies to all who share this experience. Some time ago I answered this question directly and honestly. I recently received a notice that my content had been removed. I...
    tpanty tpanty 46-50, M 2 Responses Sep 29

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    I love sexy underwear... Yes, I know others can't see it but just knowing what I've got on makes me walk a little slower. Feel a bit more seductive and choose a top that enhances...
    kissablecurvez kissablecurvez 41-45, F 2 Responses Oct 7

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    Seeing someone had begun a conversation about the use of the word "Slip" as opposed to "Petticoat", stirred up some thoughts I have had on the matter for some time! Yes I have had...
    annettepansy annettepansy 51-55, T 2 Responses 5 days ago

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    I never wear underwear and haven't for a long time. Doesn't matter what I'm wearing, short skirts, dresses, jeans, etc. I wear nothing under them. I love the freedom and thought of...
    Ohionudist1965 Ohionudist1965 46-50 2 Responses Oct 1

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    Today I'm working a little overtime and thought I'd wear briefs again instead of the usual boxer briefs. I am wearing starter black briefs.
    dph2003 dph2003 26-30, M 1 Response Oct 4

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    Part 2 less mature content. After my mom left again. We went back in my room, i asked him to rub my crotch area because the inside of my pajamas were soft and felt good on my parts...
    zetreax zetreax 16-17, F 5 Responses Oct 8

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    Because I care more about not doing laundry than being fashionable. Also, not to be confused with not caring about hygiene. Clearly if I sweat in my clothes, have been in a smelly...
    SpilledSecrets SpilledSecrets 22-25, F 2 Responses Oct 15

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    I have always loved cartoon underwear. I like buying underwear with super heroes on them. I think they are fun and sexy.
    joshuaw94 joshuaw94 18-21, M 1 Response Sep 29

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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 find it very uncomfortable. I also don't like panty lines. I've tried different kinds of underwear: bikinis, boxers, thongs but I've never been able to find anything I like, so I...
    MadameAG MadameAG 16-17, F 8 Responses Oct 17

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    Even as a little girl I use to watch my mom, both of my grandmothers, aunts & older cousins put on makeup I hate it. Lol. You can say I'm a natural beauty outside & in. I believe...
    DaCreativeChild DaCreativeChild 22-25, F 1 Response Oct 15

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    How I became a shorts fanatic Part 2There was one afternoon at school when our teacher took the register and then told us that there was going to be a staff meeting that afternoon...
    shortsfanatic shortsfanatic 31-35, M Sep 25

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    I hate the feeling of underwear holding my jewels so I rather to never wear it
    goonteam goonteam 18-21, M 2 Responses Oct 2

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    I love smelling and wearing used (dirty) mens underwear and am always on the look out for a new addition to my collection. Does this make me a bad person??
    Messer3 Messer3 36-40, M 6 Responses Oct 4

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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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    Today I went out in jeans without underwear, it was a fun, gave me a lot of confidence. As far as I know, nobody noticed, but I did enjoy every sensation more, I suppose it...
    Taurusedi Taurusedi 31-35, M 2 Responses Oct 9

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    Not all boys necessarily , but in general, I think boys should be able to wear skirts and dresses and have it be fine. Girls wear pantsuits and they're perceived as powerful. Boys...
    laracomn laracomn 16-17, F 17 Responses 6 days ago

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    If it's hot in the summertime I'll just wear my underwear and nothing else. I'll just sleep on sheets. But in the spring, fall and winter, I sleep in pyjamas and socks. I have...
    Balloonboy33 Balloonboy33 26-30, M 2 Responses Oct 2

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    I always wear tank top and shorts or just underwear. And in the winter, I gotta space heater in my room so it's never cold. I hate wearing a bra to bed, it's so uncomfortable ^o^
    Selphira Selphira 16-17, F 8 Responses Oct 3

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    I do not hate it but I do not wear everytime that I can!!I wear briefs or male thong when I wear tight jeans
    GeorgeKazas GeorgeKazas 22-25, M 1 Response Oct 5

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    Is my boyfriend possessive? My boyfriend and I are both 18 and we started dating about half a year ago. I was his first girlfriend, kiss, and so on. I can clearly tell that he...
    sky817 sky817 18-21, F Sep 26

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    I've been measured and fitted professionally by a woman in a department store. I'm a little chubby so have some breast flesh and as a crossdresser I wanted to be comfortable when...
    ris9358 ris9358 51-55, M 2 Responses Oct 9

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    My babysitting I baby sit a boy named Joey every once in a while and all he want to do is be a knight and save me (the princess) Over the last few times I made it seem like I...
    MissAlanah MissAlanah 18-21, F 8 Responses 3 days ago

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