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I Like Dressing My Boyfriend As A Woman

Personal Stories, Advice, and Support 169 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 1 Response Aug 4, 2014

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    Give him this for a gift.

    http://www.amazon.com/Feminizing-Men-Achieve-Maximum-Feminization/dp/1502959674/
    AaronFel AaronFel 36-40 Nov 28, 2014

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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 Feb 3, 2014

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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 12 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 10 Responses Dec 11, 2013

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    sexymommy2014 sexymommy2014 31-35, F 1 Response Aug 7, 2014

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    Related Experiences

    Whether it's a simple collared shirt or a whole suit and tie, dressing up is awesome. There's no feeling like being dapper!
    Blue707 Blue707 16-17, M 2 Responses Mar 1

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    I can't stand lighter blue jeans. Ever. They have to be really dark (so they're almost formal-looking), or wear some other pants. Sweatpants I can NEVER wear out and about during...
    Makaidos8 Makaidos8 18-21, M 1 Response Mar 22

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    IHATE wearing make up! Hate it! But I cannot stand sweatpants or bad looking shirts (worn down old) unless i am building ir painting something...I have to be dressed good (semi...
    Mariferb86 Mariferb86 18-21, F 2 Responses 6 days ago

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    Built for enjoyment from a heavy top to a hefty bottom. Cute and sensual all wrapped up in a full-figure package.No worries about extra pounds or wearing lots of make up. Just be...
    AfanOfbigNaturals AfanOfbigNaturals 46-50, M 1 Response 1 day ago

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    It's true I do! Well then again I want to transition to a female completely! How do I look??
    LucyAshley LucyAshley 18-21, T 5 Responses Mar 3

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    Yea feeling ugly all day everyday
    LucyAshley LucyAshley 18-21, T Mar 12

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    I'm currently seeking out my Prince Charming. I neeeed a boy friend so badly
    LucyAshley LucyAshley 18-21, T 3 Responses Mar 16

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    Yea I'm one of those girls who looks terrible in both genders
    LucyAshley LucyAshley 18-21, T 7 Responses Mar 18

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    It makes me feel better about myself and helps me believe I look nice.
    planter715 planter715 51-55, M 2 Responses Mar 6

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    I've a slight obsession with high heels and dresses.
    bleuswain bleuswain 18-21, F 3 Responses Mar 10

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    One thing I dislike more than cheese is shopping for a formal dress. ( probably because I'm picky lol) Guys have it easy when it comes to clothes. We have to look for dresses in...
    Nottheaveragegirl Nottheaveragegirl 18-21, F 10 Responses Mar 20

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    I post my outfit almost everyday on my Instagram.. some pictures I'm wearing stockings, or sexy sleepwear/lingerie I love them ..
    sadwife82 sadwife82 31-35, F 5 Responses 5 days ago

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    what is your outfit for today ? I love checking outfit on Instagram and follow their hashtags, they gives me idea of my outfit..just being a typical girl ,love clothes and shoes.
    sadwife82 sadwife82 31-35, F 1 Response 4 days ago

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    I'm Harry, I'm aged 15. I'd like a boyfriend between ages 15-17, I don't care too much about looks. I would just like a boyfriend with a good personality and can make me laugh...
    attackonzombie attackonzombie 13-15, M 2 days ago

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    uh, I'm Jake. I'm 14 and id like a boyfriend. (obviously from the title ??) and yeah. I'd really like a guy to text all the time and everything... so message me!
    Jakes1 Jakes1 13-15, M Mar 11

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    Feeling quite anxious today. Can't quite pin point it though. Nearly 4 weeks since I've seen him, 2 since the last text. 10 days off facebook. Yesterday I went through a day of...
    ravenofthedark ravenofthedark 41-45, F 6 Responses Mar 15

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    THIS IS IT!! ok so a couple weeks into 'I'm leaving her', and everything is still the same. The weekend was horrendous as they spent it together for her birthday at his family home...
    foreverWantingMore foreverWantingMore 31-35, F 6 Responses Mar 16

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    I feel like my boyfriend doesn't love me anymore. He's starting to lie about stuff, he doesn't text me or tell me loves me that much anymore. We still have a very active sex life...
    nclo8907 nclo8907 26-30, F Mar 4

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    I feel dirty but I like reaaaally older woman like 65+
    pablolpz pablolpz 18-21, M 1 Response Mar 6

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    well I don't wear them, but I do like the way woman look in them. For some reason I find them very sexy on a female.
    peppit peppit 36-40, M Mar 8

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    I haven't been able to dress in quite a while. Ever since my wife found out about my desire to cross-dress, it is like the last 25 years have been for not. All that time I cross...
    marymary1966 marymary1966 46-50 1 Response 2 hrs ago

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    me and my boyfriend have been dating almost a year and I caught him cheating me over 6 times with 6 different people I only found out cause friends of mine told me he was deleting...
    DarkKnights10 DarkKnights10 16-17, F 1 Response 57 mins ago

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    Hello all, I have had a boyfriend that has be diagnosed with bipolar and is currently not on any medical treatment. He had a plan for a while but it seemed to not stick with his...
    kc248753 kc248753 22-25, F 2 Responses 6 hrs ago

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    I know this is rather dramatic but let me list why I feel this way: -Since moving to PA, I have yet to meet any friends. I moved out here with family 9 years ago -Scratch that, I...
    RoxannaM RoxannaM 22-25, F 3 hrs ago

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    At the weekend I am going to a costume party. Of course I am dressing as a woman in a pink dress as in the cover picture. I will have to walk in public to get there as it is not...
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 9 Responses Mar 18

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    Moving Closer to Authenticity.... Every Day i receive a Good morning message that simply Delights Me... It's made more marvelous by the fact that we live in different timezones...
    warriormama warriormama 41-45, F 7 Responses 18 hrs ago

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    I actually am not sure if he wants me back. He says he still loves me and cares about me but I truly can't see it. I'm so tired of being the man. I make the sacrifices, I have to...
    gummball gummball 18-21, F 2 Responses 19 hrs ago

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    Long time ago my wife desires, and she insist me to wear her bra and panties, She herself with her hand get me wear her bra and panties She adorns me like a female. I could not...
    MarthaPampers MarthaPampers 51-55 Mar 24

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    Wish I had a boyfriend, one that actually cared about me and be there for me and love me for me and wouldn't judge me and one that would be a good listener
    decemberfairytales decemberfairytales 26-30, F 5 Responses 19 hrs ago

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    I just broke up with my boyfriend 2 weeks ago. I realized I've made a mistake but it's too late...
    MusicMonst3r MusicMonst3r 13-15, F 1 Response 16 hrs ago

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    Im so sad. I feel like im going crazy right now. I havent heard from my fiance. He called me yesterday for 1 minute he said he only had 1 minute on the phone that they didnt clear...
    Ilovemyinmate101214 Ilovemyinmate101214 22-25, F 11 hrs ago

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    I don't want a boyfriend just someone to buy me food
    CantThinkOfAUserNameLol CantThinkOfAUserNameLol 18-21, F 6 Responses 10 hrs ago

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    My boyfriend of 1 year has been in jail for almost 2 months now. He got arrested because of something he did when he was a teen. He had 6 months left and I can't wait to hug him! I...
    lalitall lalitall 18-21, F 9 hrs ago

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    My man is amazing and I feel so bad when he tries to randomly text me telling me I'm beautiful and the first words out of my mouth are "are you high?" Or "are you drunk!" It's...
    Babygirl12296 Babygirl12296 18-21, F 2 Responses 7 hrs ago

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    I want to find a boyfriend
    peedro7890 peedro7890 13-15, M 1 Response 5 hrs ago

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    Frist time I walk in a women store it was VS and the lady I talk to help me out big I told her I was thinking of dressing up as woman I think she was turn on by it she pull me by...
    virginiacox virginiacox 46-50, T 1 Response 3 days ago

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