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I Like Dressing My Boyfriend As A Woman

Personal Stories, Advice, and Support 166 People

    I'm damn jealous coz he is more ******* prettier

    and sexier than me. lol thank u for making my day.
    sexymommy2014 sexymommy2014 31-35, F 2 Responses Aug 4

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    sexymommy2014 sexymommy2014 31-35, F Aug 7

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    So I'm very new to this.

    I tried on my mom's bra/panties/pantyhose/dress for a dare and it felt pretty good. Don't misunderstand me, I'm not a crossdresser, but I am male. I posted a pic anon online (without my face) and had many guys over me. Some problems: hands not slender, shoulders too broad, hips...
    corneliousrodriguez corneliousrodriguez 22-25 1 Response Feb 3

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    My Best Friend

    Confessed to me that he likes to dress up, but never really had. He slept over one night and I set up the spare bedroom as a dressing room. I hung up at least 30 outfits and undergarments. And a makeup area and we wear the same shoe size so he walked in heels all night. When I...
    Beth4u Beth4u 36-40, F 9 Responses May 11, 2011

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    My cross dressing boyfriend

    and I are thinking about camming. I know there is a large audience for shemales, but I'm curious if there is an audience for crossdresser and female. What's your opinion?
    Lalalauli Lalalauli 31-35, F 8 Responses Dec 11, 2013

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    Related Experiences

    I love dressing up like a girl and using butt plugs x
    SluttyCP SluttyCP 18-21, M 5 Responses Aug 30

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    Bobby and the girl at a friends birthday party We watched music videos of Selena Gomez and Justin Timberlake and danced. Played truth or dare which was a lot of fun. We talked...
    bobbylee111 bobbylee111 36-40, T Aug 23

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    What girl doesn't like wearing nice clothes and looking amazing every once in a while? ;-) Sarah x
    SarahTheHooker SarahTheHooker 18-21, F 2 Responses Sep 9

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    Let me first start off by saying I am a natural worrier. By this, I mean my life wouldn't feel right or I would be bored if I didn't worry. Granted, it takes its' toll on me but I...
    Cherrybean84 Cherrybean84 26-30, F Sep 13

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    My boyfriends mom died about a week ago. We live together and thI go have been stressful since her passing. I didn't know her very well but I feel like her spirit is irritated at...
    KaitlynnW KaitlynnW 18-21, F Aug 22

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    My boyfriend and I have been together for 6 years. We have had the craziest rockiest most insane relationship ever. For four years it wasn't the best but we got through it and I...
    cutecrazy05 cutecrazy05 22-25 1 Response Sep 8

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    Would love any comments(: not to harsh please
    DoubleDirtyPanties DoubleDirtyPanties 18-21, M 9 Responses Aug 29

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    I bought a dress yesterday via online. Hopefully I will get it before saturday to wear to a party. :D Shyness be d***! :D
    FattyAndLovingMyself FattyAndLovingMyself 26-30, F 1 Response Sep 11

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    Today my job demands that I dress as Bane. 😁
    pappharry pappharry 31-35, M 2 Responses 3 days ago

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    Boys and girls riding motorcycles with their hair in 2 Long long long long ponytails
    2PrincessGirlsPonyTails24 2PrincessGirlsPonyTails24 46-50, F 1 Response 1 day ago

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    I received two letters today. It made the wait so earth while. I talked to my boyfriends best friend today also. He acts so much like my boyfriend does it isn't even funny. It's...
    armygirlfriend2007 armygirlfriend2007 18-21, F 2 days ago

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    I will maybe sound old-fashioned for some of you, but I am. I like a pregnant woman (and it is much better if I am who made her pregnant !). Pregnancy is something important for...
    FrenchBull FrenchBull 41-45 1 Response Aug 25

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    I'm 14, gay, and single and would like a boyfriend. About me: Im a bit chubby, I have red hair, and I'm about average height. Lastly, I want a boyfriend/friend who respectful...
    AidenPierce5584 AidenPierce5584 13-15, M 5 Responses Aug 27

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    So my story is a little different. It's a long one but please stay with me. He is married but I'm also engaged. I've been with my fiancé for 6 years now and I met my MM a little...
    AriLenni14 AriLenni14 22-25, F 5 Responses Sep 9

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    Im a gay 15 year-old and would like a boyfriend or/and have a gay experience. I do prefer blonde slim males from 13-19 years old so message me if your interested
    danfield1836 danfield1836 13-15, M 1 Response Sep 1

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    Today I am feeling like this for sure. It seems like no one wants to be around me. When I open my mouth, usually something stupid comes out, and then I get contradicted or...
    goldenbeginning goldenbeginning 31-35, F 1 Response Aug 26

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    My ex that I thought we were going to work it out. Change his mind, he hasn't called for two days and has been ignoring me and not being so nice. He texts me never calls dumps me...
    cara12345 cara12345 26-30, F 2 Responses 2 hrs ago

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    i don't know what it is but if I'm working and having a hard time with something, don't compare me to a woman working. such ignorance doesn't motivate me. when a woman supports...
    Storyboard0241 Storyboard0241 22-25, M 37 mins ago

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    i am almost 17 years old and have never had a boyfriend. it's better to say this... i gained a bunch of weight when i was 12, like a lot...about 25 pounds! idk what happened but i...
    KatieRosess KatieRosess 16-17, F 4 Responses 3 days ago

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    I really like this girl that is in my class. She used to like me around 8th grade but I guess I was trying to be cool so I ignored her. She moved on from me and then I realized I...
    jonvittori jonvittori 18-21, M 1 Response 2 hrs ago

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    I am a woman in my mid-30s and have Asperger Syndrome. Even with that, I completed my MBA in accounting after toying with the possibility of careers in healthcare and even law...
    nschulm nschulm 31-35, F 2 days ago

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    Can't take this :( no contact all day yesterday. Considering he said it was only space and we would never lose each other, why do I not even get a 'how are you' message? Am I that...
    foreverWantingMore foreverWantingMore 31-35, F 16 mins ago

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    I have been with the same man for 10 years and I have 3 kids with him, I love him and I can't imagine my life without him but there's this other part of me that I fight with every...
    IShouldBeSoLucky IShouldBeSoLucky 31-35, F 1 Response Aug 26

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    I go through many highs and lows with my desires to dress or to be feminine. One component of the self doubt is recognizing that there is a difference between the fantasy and...
    kope45 kope45 31-35, M 5 days ago

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    My boyfriends sister never gave me a chance and has burned her bridges for me ever giving her a chance. I am an American from Texas and I am currently living in Switzerland. I met...
    Roselipstick Roselipstick 22-25, F Aug 26

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    I am happy being the other woman because this is the choice I have made for me for now. I know my boyfriend loves me and he also loves his wife, for different reasons and in...
    mcmcintosh mcmcintosh 31-35, F 7 Responses Aug 31

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    Well, I can't decide if he's an idiot, a scumbag, or both. He's probably both. Intentional or not, his six-month rampage of inexcusable douchebaggery is coming to an end after...
    floyd228 floyd228 22-25 Sep 3

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    I am so very afraid of my boyfriend. It all started when I met him. I met him online. Yeah there is a lot of stigma against meeting people online but I had met other people and...
    naturlista10 naturlista10 31-35, F 2 days ago

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    Bobby and the girl at a friends birthday party Britney and Kathleen took me to a friends birthday party Saturday. I wore a printed knee length dress with a short net petticoat...
    bobbylee111 bobbylee111 36-40, T 1 Response Aug 23

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    Hi... My name is Autumn. Me n my boyfriend had been together almost 3 months we had dated wen I was 14 but it was bad timing bc he's 3 years older. So we gave it another shot bck...
    autumn977 autumn977 16-17, F 1 Response Aug 31

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    Last night was amazing with MM... So loving and sexy and wonderful. When I got home that sinking feeling started where I have to climb into bed without him. I miss him the second I...
    lostanddistraught lostanddistraught 22-25, F 4 Responses Sep 6

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    Lindsey is the 80 foot woman, she is a Giant and a Goddess.   Here is an experience:   As Lindsey neared the city she slowed down her walk and she walked into...
    BigCrow BigCrow 31-35, M Aug 24

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    Okay, so I have no problem what so ever with my boyfriend having a child with another woman, as a matter of fact I love his daughter as much as I love my own baby to be! I just...
    danielleLaB0 danielleLaB0 18-21, F Aug 27

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    I need to tell my story, just even for the sake of getting it off my chest and out in the open. I'm 25 and my boyfriend is 38--we met at work 7 years ago and quickly became very...
    SweetHeresy SweetHeresy 22-25, F 3 Responses Sep 3

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    I was cross dressed as an infant ??? During an extended stay with the sweetest human soul to that I have ever known (Gramma Minnie), I learned that my mother used to dress me as a...
    JessicaDale JessicaDale 51-55, T 2 Responses Sep 5

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    Yesterday, my niece called me to let me know she was going to the bar she first saw me dressed up as a woman. It is ladies' night on Wednesdays at this bar. She invited me, as...
    SweetRhonda SweetRhonda 51-55, T 1 Response Sep 11

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    Lindsey's boyfriend Max had gone to work in the city of Hamilton. It was a 35 min drive to Hamilton from his place. Max lived on a acreage about 4 miles from the nearest town. At...
    BigCrow BigCrow 31-35, M 6 days ago

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    The beauty of an Indian woman is best depicted when she adorns herself with bright and colorful traditional clothes For similar collection visit our Lehenga section at ...
    trivenisarees trivenisarees 26-30, M 1 day ago

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    My man rolled out the red carpet for my birthday today! Sorry kinda long but I had requests to provide updates. We met for my birthday breakfast then picked up my gift for his...
    saiyagyrl saiyagyrl 36-40, F 7 Responses Aug 24

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    I'm feeling really low. I just got another text from our female coworker asking if my boyfriend and I were going to MM and his wife's bbq tomorrow. Apparently his wife wanted to...
    lostanddistraught lostanddistraught 22-25, F 1 Response Aug 25

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    I would like to play dressing up. No naughty stuff. Just dressing up.
    Heellover Heellover 36-40, M 2 Responses 6 days ago

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    Reading all these stories of women who have stayed for 10+ years makes my heart ache. I don't want to put up with this emotional turmoil for that long. How did you ladies find the...
    Galaxystar25 Galaxystar25 22-25, F 1 day ago

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