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I Mom And My Sisters Kept Me A Boy In Dresses Or Skirts

Personal Stories, Advice, and Support 66 People

    I can't stand being with my boyfriend any longer, but I don't know if I can leave him...I'm too afraid to let go. So this is our story: We're at a long distance relationship...
    Bitterlove Bitterlove 16-17, F Feb 10

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    Well, i recently split up with my girlfriend and decided no more dressing up so got rid of all my girly clothes. It didn't take long tho until i needed some new underwear...while...
    algina algina 36-40 7 Responses Feb 14

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    I don't think I have to admit I like wearing dresses and skirts! I dream, yearn, desire, and want to wear anything that a woman wears, dresses, skirts, skorts or short-shorts. I'm...
    Cassandrajoan Cassandrajoan 61-65, M 4 Responses Feb 6

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    My son is seriously the light of my life. After going through a horrible miscarriage, I never thought having a child was possible for me. But the day I found out I was pregnant...
    MamaBreaABDL MamaBreaABDL 18-21, F 3 Responses Feb 16

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    At this time, I had moved schools after the time of my first story when my footshyness was developed. I was 9 with size 6 feet. (BTW I'm now 20 with size 12 feet.) I went to my...
    JamesCarter2027 JamesCarter2027 22-25, M 3 hrs ago

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    while I now have my own clothes it was my sisters that got me hooked on dresses and hose I don't think she every knew but try as I might I could not always get every thing back in...
    jamie172 jamie172 46-50, T 4 Responses Feb 9

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    I've been getting all my step sister's old stuff for over 15 years that includes panties school uniforms mini skirts swimmers both one and two pieces my...
    subsissy1989 subsissy1989 26-30, M 3 Responses Feb 14

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    Many years ago, I used to live near ‘Windy Wellington’ in New Zealand. One day, I caught the overland rail to town. The city lived up to its nickname – the wind must have...
    Billowingskirts Billowingskirts 51-55, M 1 Response Feb 7

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    I had a co worker ask me why I wear dresses and skirts, she actually said to me why are you dressing so girly. I am a woman and I like to wear dresses and skirts, I don't know why...
    Welllaugh Welllaugh 36-40, F 14 Responses Feb 19

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    I finally told someone This is already my 4th story in this group but I have to say thank you to all of you! Your comments on my story encouraged me to tell someone about my...
    ToShareStories ToShareStories 22-25, M 8 Responses Feb 24

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    I typically wear the right clothes for the right situation, working out, beach wear, etc. But day to day activity in town, at work and about, I only wear dresses and skirts. They...
    freenakedcouple freenakedcouple 26-30, F 7 Responses Feb 21

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    My step mom dresses me and so does sister i love being there sissy boy sometimes sister has her friends over and let me join the fun
    Girlyboy34 Girlyboy34 31-35, T 1 Response a week ago

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    I'm a boy who wants to get dressed as a girl so bad I always wanted to do that I don't care what you put on me I don't care if u put makeup on me that's really hard to get of. I...
    flamered1248 flamered1248 18-21, T 1 Response Feb 21

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    As I wrote in my first story (found in I Dressing Boys as Girls), sometimes all we know is what others have told us. As you also know, even though I was a boy baby, my mother...
    SylviaJames SylviaJames 56-60 4 Responses Feb 22

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    Love to look up them skirts
    smallprick smallprick 22-25, M 1 day ago

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    Hey guys! So I'm new to this site and I am looking for gay boys to talk to ( Who knows, maybe become something more than just friends). I've been single for my entire life and...
    EmeraldBoy4 EmeraldBoy4 18-21, M 1 hr ago

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    I am 48 and was married 25 years and wore mostly only tee shirts and jeans. After my divorce I lost from size 14 to 8. I straightened my hair and went with high/low lights, added...
    Sharpi1 Sharpi1 46-50, F 7 Responses Feb 15

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    I have been wanting to vent for months about the situation I'm going through and I hope someone can lend me their genuine advice on this. I've been dating my boyfriend for 3 years...
    nlth20 nlth20 18-21, F Feb 15

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    Yes, its true! I love wearing dresses; short, to my knee's or way above them, or anywhere below my knees. Guess what? I'm a man and I've always felt comfortable and at ease wearing...
    Cassandrajoan Cassandrajoan 61-65, M 6 Responses Feb 6

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    Really want to get dresses for Valentine's Day. Won't but want too. If love to surprise my wife and be myself. She won't agree.
    shadowplt shadowplt 51-55, M 2 Responses Feb 13

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    My mom made me go with her and i brought 10 pink dresses all of different length the shortest barely covers my little penis and the longest goes to my ankles...
    subsissy1989 subsissy1989 26-30, M 3 Responses Feb 14

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    And most of her friends, too. With a burning passion. They harass me, staring, pointing, whispering about me. I tried telling my mom, and she dismissed the behavior, and found...
    Smolderous Smolderous 16-17, F Feb 14

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    When I was 16, my parents separated. It was devastating for my 2 sisters and I (let alone our mom). From the day our parents sat us down and told us, we made a pact that we will...
    Yankeegurl1216 Yankeegurl1216 41-45, F 1 Response a week ago

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    I'm a stay at home mom with a 2 year old daughter and a 1 month old son and i love being able to spend every second with my babies. but i miss having just a simple adult...
    ashleynichole25 ashleynichole25 22-25, F 3 hrs ago

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    I just love wearing short babydolls and fit and flare dresses. It has to be short, it is all about the legs !
    Plugslave Plugslave 31-35 11 Responses Feb 15

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    So today I had my makeover. It was awesome. I tried on lots of outfits, and we chose a blue skater dress with daisies on it, opaque tights, wedge ankle boots with fur trim , and...
    donnaka donnaka 36-40 9 Responses Feb 23

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    I am a 14 year old girl who doesn't get along with my mum. Me and my mum would get along maybe 10% of the time, the other 90% we fight or don't talk to each other. I really want...
    coolgirl2112 coolgirl2112 13-15, F 1 Response Feb 10

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    I know, I know. I talk about my kids too much. Don't care. These girls are a hoot. LOL They talk to me. Sometimes without breathing. Sometimes so much that I threaten to change my...
    justNIK justNIK 41-45, F Feb 17

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    Where and how does it all begin? At an older age we may not remember possibly the best we can do is to go on what our elders have told us through the years. Thinking back on some...
    SylviaJames SylviaJames 56-60 4 Responses Feb 21

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    Hey, I'm Savannah. I turned 18 years old last month, I am a mommy of 2 little girls and a little boy on the way and this is my story. My story started when I had my first...
    SavannahLily SavannahLily 18-21, F a week ago

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    He busted my lip several nights ago. He hit me hard when he was drunk and stoned. He promised me he would no longer get drunk and stoned because of his volatile nonsensical...
    Calmclarity Calmclarity 26-30 Feb 24

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    Hi All ! I want to know if I am seeing this situation for what it really is or if my judgement is being clouded by my own insecurities and fear or imagined.. or there is a genuine...
    lolitaloa lolitaloa 26-30, F 1 day ago

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    I grew up in a small town in the Upper Peninsula of Mich. in the 60's and 70's. My "mom" came from a family of 13 brothers and sisters of Polish decent. During family meals my dad...
    yooper01 yooper01 56-60, F Feb 8

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    My little sister has autism sometimes ( like you would do with any sibling ) I yell at her then my mom hers me and yells at me the reason I yell at my sister is because she tried...
    cutekyrabear cutekyrabear 13-15, F 2 Responses Feb 23

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    my mom had a rough upbringing. rape, abuse, etc with about 13 other brothers and sisters. she had 3 kids. I'm the baby. as kids, we had a horrible childhood as well. she made sure...
    niafiend niafiend 18-21, F 5 Responses Feb 24

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    I haven't lived with my mom since I was 7, so about 10 yrs now. She has come in&out of my life for all these years, she runs away to go back to my abusive step dad and takes my...
    lexilove43012 lexilove43012 16-17, F 1 Response 4 days ago

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    Yes, its true! I love wearing dresses; short, to my knee's or way above them, or anywhere below my knees. Guess what? I'm a man and I've always felt comfortable and at ease wearing...
    Cassandrajoan Cassandrajoan 61-65, M 1 Response Feb 6

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    It feels good to type everything down here.. I have been keeping everything to myself and it is getting harder to manage but I am sure that I can seek advises from other persons...
    Zenalia Zenalia 18-21, F Feb 23

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    So I've been dating this guy for almost two years and he's really amazing and we love each other. What makes things difficult is that he plays rugby, and his high school, and now...
    ShioriVO ShioriVO 18-21, F a week ago

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    Apparently he "didn't feel the same anymore". For four weeks he kept this from me, he told everyone but me. He made me live a lie for an entire month. He said "when I started...
    Sharebare519 Sharebare519 13-15, F 5 days ago

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    It was rather hot today and to be comfortable I wore one of short demin skirts, not that fashionable but comfy
    paula3198 paula3198 46-50, F 2 Responses Feb 7

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