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I Love Crossdressing For Halloween

Personal Stories, Advice, and Support 175 People

    " Dressin' Up " - Every Halloween I wanted to get dressed up as a woman, but my wife at the time wouldn't let me. Now my wife helps me get dressed up for Halloween. It wa...
    davis36a davis36a 61-65 2 Responses Jan 23, 2012

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    My Dream Costumes... - There are a couple of costumes that I would LOVE to wear for Halloween. One of them is a ballerina -- either a tutu and white or pink tights or maybe a...
    driver88 driver88 46-50, M Jun 24, 2012

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    Tonight's The Big Night! - OK tonight is the big night. Tonight I’m going out with my wife to a huge party in Houston. I’ll be in my panties, stockings, petticoat, heels and...
    2muchexp 2muchexp 51-55, M Oct 26, 2013

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    Going All-out This Year - I've crossdressed several times for Halloween, but this year I'm doing something I've never done before. Two friends of mine and I are going to dress up...
    jennyla73 jennyla73 36-40, F 4 Responses Sep 21, 2012

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    Finally Did It! - For as long as I can remember, I've always wished that I had the guts to be a girl for halloween. Even in elementary school, I remember there was always at least...
    wesleyd wesleyd 22-25 2 Responses Jun 7, 2012

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    Party III - Where we left off. Me and my wife are at a holloween party crossdresssed and the girls have cornered me about my sex life in he kitchen. Cindy asks "How big is Julie's...
    deleted deleted 26-30 7 Responses Nov 6, 2012

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    Party - wife has me practicing wearing 4 inch heels for Halloween this year she has me going as a **** in a minidress and she is going as my boyfriend even going to wear her...
    deleted deleted 26-30 5 Responses Sep 18, 2012

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    Did It! (Follow Up To: Tonight’S The Big Night) - The deed is done. I did it. WE did it. First my wife shaved every body hair I had from the neck down not including my arms...
    2muchexp 2muchexp 51-55, M Oct 28, 2013

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    My Wife went out to get us costumes for halloween i told her to suprise me , even tho we both knew it would be girl costumes. she came back with a coupla different costumes. but...
    Savannah907 Savannah907 46-50 1 Response Mar 22

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    My Wife Crossdressed Me Then Took Me to a Halloween Party. - About ten years ago we got invited to a last minute halloween party. I said we didn't have any costumes. The people...
    IMACD IMACD 56-60 9 Responses Feb 11, 2009

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    One Halloween At The Office. - Well first I'll give some background, at work we had a summer swim party several years back. I have long thin legs. They do look like girls' legs. So...
    JoanneF JoanneF 36-40, F 7 Responses Oct 25, 2010

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    Dressing Up For Halloween - Several times I have dressed up for halloween and me and my wife even dressed as playmate twins one year, it was fun and we got lots of attention for...
    pantiescouple pantiescouple 26-30 1 Response Oct 1, 2012

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    Transpire? - Silly idea. Could a cross dressing vampire be called a tranpire? Instead of sucking blood to survive, might a tranpire survive by sucking other fluids
    Officestyle Officestyle 36-40, T 4 Responses Oct 25, 2012

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    Party II - My wife has been training me for weeks to walk and dance in 4in stillettos. Now its time for the party well last night was, She started to get me ready early at three in...
    deleted deleted 26-30 5 Responses Nov 5, 2012

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    Seems To Be...... - the only time of year that I would have some excuse to give some one if I were to be caught, discovered or found dressed up or crossdressed. So every year...
    allyg allyg 41-45 Dec 5, 2010

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    Fem Sissy Boy is honestly searching for a masculine and protective boyfriend/husband and treat me as your princess wife! I am TG and would even love to dress for you and if you...
    FemGayBottom FemGayBottom 26-30, T Apr 4

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    Ford was one of the best. The Blackboard Jungle, The Big Heat, The Violent Men, Gilda and 3:10 to Yuma are essentials. If you like aviation try The Gallant Journey.
    johnny048 johnny048 46-50, M 9 hrs ago

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    Every Sunday Morning I prepare Breakfast for my four children, Wife, and Father. It is a tradition my dad started when I was a kid. I love to watch them enjoy breakfast as we all...
    Interstellartraveler Interstellartraveler 36-40, M 3 Responses Mar 21

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    I've never really tried or paid any attention to guys until this past year when one of my relatives asked me why I was still single... I had no answer besides that I was busy with...
    fgarci04 fgarci04 18-21, F Mar 25

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    Best online shopping for crossdressers is Glamour Boutique! GlamourBoutique.com Please check them out. Tell them Cami highly recommended it!! I LOVE the people at...
    Camilla2014 Camilla2014 46-50, T 2 Responses Mar 28

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    I have shoe shopping problems .. I buy all the shoes I want and obsessed with heels , when I was a teenager I used to wear them all the time and after my daughter was born I didn't...
    daisy92 daisy92 18-21, F 3 Responses Apr 2

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    Wabi Sabi: the ancient Japanese idea of illuminating the beauty in imperfection. Love. It’s right up there with air, food, and water as the most necessary of ingredients for...
    Luna47 Luna47 46-50, F 1 Response Apr 6

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    I remember I cooked an actual "romantic style" meal for my best friend whom i loved when I went to her house and I actually did a good job. I cooked her simple stuff like pasta...
    emilesfault emilesfault 16-17, M Apr 7

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    I love to drive for about an hour, explore the city and find new parks, it´s awesome how many new spots you can find while you drive at night.
    Zua95 Zua95 18-21, M 1 day ago

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    All I want is a girl that wants me for me, if you want to know what kind of girls I like read my other experiences.
    shaunrain shaunrain 16-17, M 1 Response Mar 16

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    Tonight is comfort food . Spaghetti with meatballs for the meat eaters and garlic bread , salad and for dessert brownies with homemade gelato .
    Dancemomisme Dancemomisme 46-50, F 2 Responses Mar 24

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    Man stuck in a dress. I had gone dress shopping at a department store wile out of town. I chose four or five dresses to try on. I found the dressing rooms and went in. I tried on...
    mat2Robin43 mat2Robin43 51-55, M 1 Response Mar 27

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    I am looking to go on a foraging adventure. Have you ever gone out for a few days and just survived with what you found?
    odyssey13 odyssey13 36-40, M Mar 27

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    I dont know if this post is still working, but I want/need to share my story. I was married to a guy who was a psycho when I was not even 18. Coming from India, thats like a death...
    kindredspirit75 kindredspirit75 36-40, F 1 Response Apr 5

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    It's great fun to just get in the car and drive with nowhere in mind. I once ended up 400miles away from my house before I stopped for the night and went home in the morning.
    SalinNY SalinNY 46-50, F 4 Responses 1 day ago

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    Part two. Remember in the last one when I told you AJ and I saw girls from are grade. On Sunday AJ and I stayed over Ashley's house. She had Brianna and Jordyn over. AJ and...
    Sarahismygirlname Sarahismygirlname 13-15, T Mar 17

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    It's extremely agitating comparing myself to others. It's almost an unwanted obsession that ceases to stop. I'm at the breaking point about to tear these walls down. I cannot...
    Allissaxxx Allissaxxx 22-25, F 1 Response Mar 28

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    Seattle pizza sucks! But N.Y.'s pizza rulz!! Btw the pic is of cheese!!
    Awesome5790 Awesome5790 13-15, M 1 Response Mar 28

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    I'm all ready..who's coming with me? #ladiesnight #wednesday
    dreamprinc3ss dreamprinc3ss 31-35, F 5 Responses Apr 2

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    Just received a gift card to DSW! I know where my money is running off to! 👠👠👠👠👠👠❤️❤️❤️❤️❤️
    Zacarabear Zacarabear 18-21, F 1 Response Apr 2

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    I picked up my 2nd pair of 40th anniversary L'eggs pantyhose in the Limited Edition Classic 'EGG' packaging on Sat. have been trying to find what colors they are coming in. So...
    krisyca krisyca 41-45, T 3 Responses Apr 7

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    Gotta eat them all!! Pizzamon!!! :3
    Oti91 Oti91 22-25, M 1 Response 5 days ago

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    It is such a stress reliever!
    kelgurl kelgurl 31-35, F 1 Response 4 days ago

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    totally gonna be elsa for halloween/comic con!! going to have to make my own dress though/:
    heartslob heartslob 16-17, F 1 Response 14 hrs ago

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    I've been pretty much a halloween person for all my life as I do enjoy dressing up. I've dressed up as so many things for halloween it's hard to list them all but my recent ones...
    Monstermaster13 Monstermaster13 22-25, M Mar 19

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    Hi. Im a male 18 at college. Ive been crossdressing for a while but am looking for a female to talk with about it and whatever..message me on here
    Zxi19 Zxi19 18-21, M Mar 30

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    If you'd like to explore a new album, check out Forever Halloween by The Maine. It's just not your usual rock album. Plus, it was released independently and recorded straight to...
    graxaxa graxaxa 22-25, F Mar 21

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    For the longest time, I thought being born on Valentine’s day, sucked. Yeah, it’s a holiday full of love and for those without a partner or sweetheart… it sucks...
    bemyvalentine bemyvalentine 51-55, F 1 Response 2 hrs ago

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    I had the most amazing experience regarding a Lunar eclipse that happened in the very early morning of this world. For those who have been down or worried, if this isn't a message...
    BelleGold BelleGold 16-17, F 1 hr ago

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    You're absolutely perfect in every way to me. You're so sweet and kind, you're the only one in my entire life who ever loved me for me..my mother nor father even loved me, but you...
    SarahBear907 SarahBear907 16-17, F Mar 15

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    Usually I'll listen to love songs like the sad ones and cry it out, since I don't feel like I deserve love thanks to my extremely abusive past, but my boyfriend/fiancé knows all...
    SkitLaberge SkitLaberge 18-21, F Mar 17

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    I cant explain how much i love him you will get sleepy. Im going to meet him in a couple days and that feeling with butterfiles i love it and hate it. But im slow i cant show love...
    missunperfectly missunperfectly 13-15, F Mar 21

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    I found the guy that loves me for my personality and not just my body. I found the guy who loves the idea of spending a Friday night in with me, watching movies. I found the guy...
    krorenae krorenae 18-21, F 2 Responses Mar 25

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    I Love vacations near the sea as sea atract me,love swimming love bikini,love Greece for this.
    blackweirdcat blackweirdcat 46-50, F Apr 1

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    My hubby called me into the study last night to listen to a song which he said is perfect for us. So I sat down and watched the video with him. Needless to say, I loved it!I love...
    littleAnonyMOUSE littleAnonyMOUSE 41-45, F Mar 15

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    I love my teacher.... I just need to get this off my cheast.I love her. I just love her. I love how her eyes shine in the sun,her beautiful eyes. Her eyes change colour you know...
    screwthem8 screwthem8 22-25, F Mar 15