I Like Dressing Up Like A Girl

Personal Stories, Advice, and Support 2,507 People

    I am 15 year old sissy boy

    who likes to wear his 18 year old sisters bikini bra panties gowns Lingirie dresses skirts tights leggings and definitely her make up and it's a secret amd I secretly like tough Men and masculine ones
    deleted deleted
    26-30
    1 Response Sep 20, 2015

    One Of My Favorite Things

    I had a chance to do one of my favorite things today i got all dressed up and went outside to take some photos. i had a cute outfit some nice jeans and a cute tank top with a sports bra under it. the pictures came out really good please check them out.
    ashley2o2 ashley2o2
    22-25, F
    4 Responses May 15, 2013

    Crossdressing :)

    So not so long ago i told a girl i crossdress and she supports me so she gave me some clothes :) Yesterday my mom went to run sone errands so i started crossdressing. I wore my friend clothes (short shorts and a top) and my moms underwear and bra. I knew she was gonna be gone so...
    MrMumboE3 MrMumboE3
    18-21, M
    4 Responses Oct 13, 2012

    Boys and girls riding motorcycles with their

    hair in 2 Long long long long ponytails
    2PrincessGirlsPonyTails24 2PrincessGirlsPonyTails24
    46-50, F
    3 Responses Sep 20, 2014

    Yea I'm one of those girls

    who looks terrible in both genders
    LucyAshley LucyAshley
    18-21, T
    9 Responses Mar 18, 2015

    I wish it was summer I wanna go swimming!

    How do I even look in this anyway?
    LucyAshley LucyAshley
    18-21, T
    4 Responses Feb 17, 2015

    FantasyLand! My little red riding hood outfit.

    I need a man to keep the big bad wolf away from this girly girl
    deleted deleted
    26-30
    6 Responses Jan 23
    DildoSniper DildoSniper
    22-25, M
    Aug 19, 2015

    Always have, always will,

    that **** never gets old.
    Shannongirlyboy Shannongirlyboy
    46-50, T
    5 Responses Sep 23, 2014

    Its All I Think About 24/7

    I STARTED DRESSING UP WHEN I WAS 5. I HATED BEING A BOY AND WOULD STEAL MY SISTERS PANTYS AND NYLONS. BY THE TIME I HIT PUBERTY MY DESIRES WENT OFF THE CHART AND HONESTLY FELT I WAS GOING TO TURN IN TO A WOMAN.i WAS ALWAYS WANTED AND OLDER WPMAN TO CATCH ME AND TURN ME IN TO HER...
    nylongirl12 nylongirl12
    36-40, T
    2 Responses Feb 25, 2013

    I Like Crossdressing

    I like dressing up in girl 's clothing.  I like it a lot and have been doing it now for many years.  It is really  a lot of fun to dress in dresses and skirts and girls tops or blouses.   I  feel I am who i am when dressed as a girl.  Girls clothes provide the...
    jml2000 jml2000
    61-65, M
    3 Responses Sep 9, 2012

    Thinking about changing my hair debating on

    going blonde or a purple to pink hombre
    LucyAshley LucyAshley
    18-21, T
    3 Responses Jan 14, 2015

    Yep I also want to be a girl

    so I mean that's why haha
    LucyAshley LucyAshley
    18-21, T
    4 Responses Feb 3, 2015

    My First Crossdressing (;

    last night my sister forced me to dress up as her little sister haha. i wore a bra and top and her prom dress, it was a mini pink poofy dress(: she did my make up she put pink lipgloss on my lips and black eyeshadow long eyeliner and planty of mascara. and some blush.. she...
    SHAY8877 SHAY8877
    16-17, M
    1 Response Sep 28, 2012

    The most wonderful thing has happened my wife

    and I relocated to sw Florida moved into our dream home and are really loving it here😃 However that's not why I'm writing it's about a side effect that happened during the hole relocation process. You see my wife moved down in April w me to follow in a month well a month...
    Tammi5157 Tammi5157
    51-55, M
    7 Responses Dec 23, 2014

    The first time I ever really felt like a girl

    was went I was 14. My mother had been dieting and lost some weight. She wanted to hem some of her dresses, so she asked me if I would wear some for her .I said no way but then she offered 10 bucks if I would. I agreed and we went into her room where she prosceded to dress me in...
    julieasner12 julieasner12
    26-30, F
    9 Responses Sep 6, 2015

    I'm currently seeking out my Prince Charming.

    I neeeed a boy friend so badly
    LucyAshley LucyAshley
    18-21, T
    3 Responses Mar 16, 2015

    I am a 15 year old girlyboy

    who secretly wears his 18 year old sisters lingerie gowns bikini bras panties skirts shirts leggings and make up and I'm attracted to tough men it's all a secret
    deleted deleted
    26-30
    1 Response Aug 20, 2015
    daya55 daya55
    31-35, M
    1 Response Jan 16, 2015

    I don't know why but I'm beginning to like

    dressing like a girl and feeling like one..the only thing is I like doing it sometimes not all the time and I'm straight..what's wrong with me please help
    Heaven21 Heaven21
    22-25, M
    8 Responses Jul 24, 2014

    I just love dressing up

    and being the girl I feel like inside. It feels so good on so many levels, physically and emotionally, to slip on my panties, pull up my stockings, clip on a pretty bra, and slip on a cute dress. With my hair hanging down and ticking my neck and shoulders, my dress blowing in...
    bethanngirl bethanngirl
    56-60, M
    13 Responses Mar 1, 2014

    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
    6 Responses Mar 3, 2015

    Well I like to dress up girly

    and practice some mannerisms. So a couple of weeks ago we had some snow and I had to go out and clear the driveway and sidewalks. I was wearing a black pushup bra, black garter, black thigh highs and brite blue silk panties and painted red toenails so i threw on some sweatpants...
    deleted deleted
    26-30
    7 Responses Dec 29, 2013
    LucyAshley LucyAshley
    18-21, T
    9 Responses Feb 4, 2015

    I Like To Be Pinknprettyyy

    dressing up like a girl is alot of fun for me i feel so cute and i feel i am who i want to be when i am dressed. weather im wearing the heels the panties nylons or the bras they all give me the feeling of being free to my self and pretty on the inside and PinknPrettyyy on the...
    AlliHastings AlliHastings
    26-30
    10 Responses Aug 18, 2012
    LucyAshley LucyAshley
    18-21, T
    2 Responses Feb 27, 2015

    Maybe this is the wrong group

    but it seems appropriate. I have been a "in the closet" cross-dresser for a long time and I was very confused about why I liked to dress as a woman my family was very disapproving (get to more on that later) but I still wanted nothing less but to embrace the feminine side of my...
    shadownexus3299695 shadownexus3299695
    26-30, F
    6 Responses Jan 28

    Yay Me!

    I am the proud new owner of two new pairs of heels, a halter top, a mini skirt, a cocktail dress and a cami!!! I can't believe I actually Bought them today. But it was such a great feeling, and I can't wait to get them on.
    NvPantieLVR NvPantieLVR
    26-30, M
    2 Responses Apr 14, 2013

    Cross Dressing

    I was 14 when I first put a girls swimsuit on...I felt normal then.
    BlueNight99 BlueNight99
    36-40, M
    9 Responses Jun 7, 2012

    I am a weirdo and I don't care.

    I like to wear crops and expose my bellybutton.
    Profweird Profweird
    22-25, M
    2 Responses Oct 1, 2014

    I used to dress up as a girl 4 times a week.

    Haven't gotten a chance since Rocky Horror in October. I hate being a man 24/7
    Foxanne Foxanne
    22-25, T
    6 Responses Dec 7, 2015

    Wearing a bombshell bra

    and panties, black pullover, red plaid mini skirt, fishnet stockings and MaryJane shoes, foundation, black eye shadow, red lipstick and my Cleopatra wig. It feels so right.
    Foxanne Foxanne
    22-25, T
    4 Responses Aug 27, 2015

    Whilst The Wife's Away

    ...I got to dress and play. I've spent most of the time in the apartment this weekend in women's clothes. I did venture out to walk the dog in the dark before dawn. This morning, I was more bold than ever. I took trash down into the garage beneath the apartment building...
    JosetteLaRoc JosetteLaRoc
    36-40
    4 Responses Jun 10, 2012

    My Girl Is Me

    I absolutly love dressing like a girl. I could live like that the rest of my life. I do most of the time now but not enought. I want to all of the time.
    Veronicatwo Veronicatwo
    61-65, T
    5 Responses Nov 27, 2012

    Love the feel of all the sexy lingerie under my

    silk blouse and girls low rise jeans..pumps..also wearing my silicone breast forms large size..love to jog just a bit to get the big bouncing of my ****...
    kysatinman kysatinman
    46-50, T
    2 Responses Dec 31, 2013

    i am wearing panty for my work its

    so soft and so comfortable..........
    daya55 daya55
    31-35, M
    1 Response Jan 15, 2015

    i really want to walk around outside in cute

    clothes and go to the mall and go shopping, but im scared people will know im a boy, i really dont like being a boy ive always wanted to be a girl since i started remembering
    ChrissychrisSa ChrissychrisSa
    18-21, M
    4 Responses Jan 5

    You guys asked for other pictures

    so here you go ❤️
    LucyAshley LucyAshley
    18-21, T
    5 Responses Feb 18, 2015

    Expressing Myself.

    When you are a petite 5'3" 118 lb. like me, it's hard to be mocho. I've always been very attracted to women and their femininity. I've also always had a desire to immolate them.I have a passive, sensitive personality and I love pretty feminine clothing. I'm also very fortunate to...
    silkydrawers silkydrawers
    46-50
    8 Responses Dec 1, 2013

    I'm really just looking

    for friends, other crossdressers for a support system and really just to hang out and dress up together. I'm not looking for anything sexual so please don't message me asking.
    hchris992 hchris992
    26-30, M
    4 Responses Mar 18
    LucyAshley LucyAshley
    18-21, T
    Mar 12, 2015

    From my profile: I am a psychologist named

    Julie Wilson. My chief interest is teaching boys respect for women. The most effective psychological technique for accomplishing this is called role playing. Role playing consists in putting a person in the role of another so that they will gain insights into what it means to be...
    TeachingRespect TeachingRespect
    51-55, F
    1 Response Mar 12

    I'm in a lace pink thong push up bra

    and yoga pants. Anybody want to talk?
    yuyu0079 yuyu0079
    18-21, M
    2 Responses Dec 24, 2014

    I'm a 15 year old sissyboy

    who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings thongs dresses skirts tank tops gowns skinny jeans heels and definetly make up and I also secretly am attracted to masculine tough and hairy men
    deleted deleted
    26-30
    1 Response Dec 5, 2015
    LucyAshley LucyAshley
    18-21, T
    1 Response Feb 18, 2015
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