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I My Brother Is A Sissy In Dresses

Personal Stories, Advice, and Support 103 People

    My Brother Is A Sissy

    Look!My brother,What a sissy!Wearing those dresses!When will he ever learn?He's not a girl!
    lazycrazybasket lazycrazybasket 46-50, M 3 Responses Sep 27, 2011

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    I Am The Brother/sister

    my older sister didnt want a younger brother so she started dressing me mom thought it was cute then realized it was cheaper to just have me wear sisters 2nd hand stuff now i live full out as a sissy
    sissykrisb sissykrisb 51-55, T 1 Response Nov 26, 2012

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    My Sissy Cousin,.....and His Little Weewee,.....

    I am very much interested in Dom-Sub relationship. My cousin use me as her **** from my 12 year on wards. Sometimes she will give me spanking also. She made me call her Aunty really her mother is (my moms elder sis) and she disciplines me with Bare hand, slippers and belts. She...
    ambili ambili 22-25, F 12 Responses Oct 1, 2011

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    Related Experiences

    When I grew up I did at least in private and sometimes not so private wear short pleated skirts and the occasional pinafore style dress. This was not a punishment and indeed I am...
    littlegreyshorts littlegreyshorts 51-55, M 4 Responses Aug 1

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    You can never have too many Little Black Dresses in your closet. I am always searching for new ones because the truth of the matter is, you can wear them anywhere! With the holiday...
    kitty002 kitty002 31-35, F 1 Response Aug 4

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    My sissy and i put itchy powder in a VERY VERY sensitive place
    camitheboss camitheboss 13-15, F 8 Responses Aug 10

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    I am a sissy that wants to be taken and used by alpha males and turned into a sissy bimbo ****
    Sissyboitaylor Sissyboitaylor 18-21, T 7 Responses Aug 3

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    I love wearing all kinds of lingerie, and I especially like the kind that makes me feel like a sissy. I made this video when I was feeling a little sissyish. I hope you like it...
    VictoriaFredericks VictoriaFredericks 36-40, M 3 Responses Aug 12

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    Yesterday was the fist day i spent with by master. I loved being all dressed up in really cute sissy clothes (he even made me lock my boy **** in a cage) and he made me service...
    bottomslut1 bottomslut1 18-21, M 2 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 11 Responses Aug 1

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    Dressed my best friend in a dress today and he did not look gay he looked quite nice to be honest I hope he wears it more and more and I don't know why guys can't wear skirts or...
    honeypettle honeypettle 36-40, F 3 Responses Aug 3

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    Got to wear a dress an entire afternoon and evening after work on two days this past weekend... It was so nice. Since my family was out for the weekend I didn't have to worry about...
    Roccondil Roccondil 22-25, M 9 Responses Aug 7

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    OK... Google the phrase "shopping tunic", then click the "shopping" tab. You'll see that pretty much all the results are for "women's tunic dresses". Then search "gladiator sandals...
    steve66oh steve66oh 41-45, M 6 Responses Aug 11

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    I'm a proud sissy, and I want to play. Message me. Please. You won't regret it :p
    raelynnCD raelynnCD 18-21, T 6 Responses Jul 24

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    Gosh some of those online tests are absolutely worthless! LOL But, on the few that were actually worth the time to take... I passed the Sissy Test, with flying colors!
    curiositykillz805 curiositykillz805 46-50, M Aug 12

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    how can i become some ones sissy
    gerommino gerommino 66-70, M 3 Responses Aug 13

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    I am trying to find a way to be noticed as a sissy by women, last night I went out back to a main road, and I wore just panties and shoes, and stood by the road, so many cars drove...
    sissyslut4training19 sissyslut4training19 18-21, M 1 day ago

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    Likes to dress me beautiful. Already as a little girl I liked it, to wear lovely dresses and skirts and that's still the same. Of course I have pants, leggings and sweater but I'd...
    prettysybill prettysybill 22-25, F 5 Responses Jul 24

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    If I do find a dress that I like I'll get it I'm very picky when it comes to dresses But I love my birthday dress
    andreaespe andreaespe 18-21, F 2 Responses Jul 27

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    I have fallen in love with Maxi Dresses lately, what do you think of this one? I think it's absolutely beautiful :)
    LisaTG LisaTG 26-30, T 10 Responses Jul 31

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    I have worn dresses or skirts since i was 6 but i would love to live in a world where a boy can wear them openly instead of having to be called a cross dresser. i hope that day...
    jamie172 jamie172 46-50, T 9 Responses Aug 4

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    A little conversation with my 3 year old daughter the other day. She was wearing a pretty little dress, spinning round so the skirts puffed out. She looked so cute. She turned to...
    Heellover Heellover 36-40, M 8 Responses Aug 8

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    I love to wear my short dresses with thigh high boots :)
    PoojaTimberlake PoojaTimberlake 18-21, F 10 Responses Aug 8

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    I love to dress up and wear short dresses and skirts with a nice looking blouse or top. Also, I love to wear shorts and swimwear with hose and four inch high heels on.
    tammylynne tammylynne 41-45, F 8 Responses Aug 10

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    Wearing dresses make me feel more feminine
    KinkyKatieLouise KinkyKatieLouise 41-45 6 Responses Aug 13

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    I'm Pentecostal so I have my reasons. Besides my religion, I enjoy wearing dresses and skirts instead of pants. Pants are so uncomfortable.
    PeaceBatman PeaceBatman 22-25, F 5 Responses 6 days ago

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    because I didn't do well in my school report and grades that my stepdad decided I need more discipline and has now decided to make me wear dresses after my punishment to humiliate...
    tony2014 tony2014 13-15, M 1 Response 6 days ago

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    I wear a dress as often as possible. It's such a free feeling. You don't have to wear underwear if it's not see thru. I love the way they look, especially the long ones that are...
    jaylow13 jaylow13 36-40, F 2 Responses 3 days ago

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    I like to wear dresses or skirts - and preferably short ones - as often as I can. Partly because I like to feel - and look - feminine - and because my husbands loves to see me that...
    Susanna3 Susanna3 31-35, F 2 Responses 1 day ago

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    So, to day was my last picture day, and I decided to wear a pretty white dress it's so cute, and perfect for summer! I never wear dresses but, I love them I really want more.
    Vannarose Vannarose 16-17, F 1 Response 1 day ago

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    Apart from shorts, I have only been wearing dresses or skirts since I was 8 or something. And apart from the fact that my husband does not want to see me in trousers, I like...
    Susanna3 Susanna3 31-35, F 2 Responses 23 hrs ago

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    I live at home with my parents and two brothers since I am only fourteen, I know brothers are "suposed" to be annoying but what I am experiencing is close to rape. My little...
    illusionarytheory illusionarytheory 18-21, F 1 Response Aug 3

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    Okay, so I've noticed this within the past year or so. My mom is always going around treating my brother (middle child) better, and she acts like she likes him more, even though...
    whyphy whyphy 13-15, F 1 Response 4 days ago

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    Ever since my older brother started living with me I have grown to hate him so much. I know that hate is a strong word and that you should never hate someone but with him, I do. My...
    supernovaChic supernovaChic 22-25, F 4 Responses Jul 23

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    My brothers gone...sorry if this is long but it's what happend. My names Nevada and I'm 14. I'm the only girl my parents have, I have four older brothers. Declan is 21, Jackson is...
    VadaDrewSeventh VadaDrewSeventh 16-17, F 1 Response Jul 25

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    I been in a relationship with my boyfriend for about four years. I love him, I really do. He's sweet but also has his dark side. He's hit me before and also cheated. I've forgave...
    unspokenwords14 unspokenwords14 18-21, F 2 Responses Jul 28

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    When I was 11 my brother who was 14 wanted to have his own room for once, so my parents gave him the guest room, I was sad as I really have like a special bond with him, that night...
    1993george 1993george 18-21, M 2 Responses Aug 5

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    So my brother come out gay when he was 13 and people always say to me isn't it weird or creepy and how can you trust your son around him. But what really annoys me is that when I...
    cparker7789 cparker7789 31-35, M Aug 7

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    (sorry about all the grammar and language mistakes, my english is not perfect but i'm trying to improve)   I wanted to tell you about my relationship with my brother...It was...
    Macaronz Macaronz 22-25, F 2 days ago

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    So my mom had me, and since neither her nor my dad could take care of me I was put in the custody of my grandparents. 5 years later she got knocked up by another man and had my...
    fryktus fryktus 16-17, M 1 Response Jul 25

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    i loved my brother, he was 5 years older than me.. he used to take me out to theme parks n treat me ice cream =D whenever i'm sad n crying, he would hug me n pat my head saying...
    Jasmile Jasmile 22-25, F 3 Responses Jul 26

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    Blazingdragon, is my ep brother. I will not give out his name because I don't know if he wants me too. I'm wrighting this for him. Me and him met around a year ago. We didn't talk...
    crazyhyperkid crazyhyperkid 13-15, M 5 Responses Aug 1

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    Oh my... My brother he is 23 and she is 19 I am only 17 so this girl he met her in June my brother andI are also close! Well... Were.. So my brother has been seeing this girl for a...
    lostboysmarko4 lostboysmarko4 16-17, F 1 Response Aug 2

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    I have a older brother I have not heard from him in over 6 months to a year since my mom passed be 4 years this November he has not been in contact much last time he was between...
    sunnyday55 sunnyday55 46-50, F 1 Response Aug 9

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    I was raised my 2 older brothers who are 25 and 30. They are really over protective and they dont believe in corporal punishment and dont believe in hitting me. A few years ago I...
    17kabarb 17kabarb 13-15, F Aug 10

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    It was a month ago that I became mad on my brother he was sleeping I picked up a rubber sleeper and started spanking my brother I am 13 while he is 25 after three swats he get up...
    ahmadiscrazy ahmadiscrazy 13-15, M Aug 13

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    I can't stand my brother's girlfriend. She is disrespectful and rude. She is spoiled and stupid. She won't stay at a job for longer than a couple of months because she doesn't like...
    aj2456 aj2456 22-25, F Jul 24

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