My guy has been hinting that he might like to dress up as a lady for Halloween! It sounds like fun but I don’t?




know, it also sounds kind of wierd!
I mean he in nice shape and not very big so he might actually be able to pull this off!

Any thoughts or experiences with this ?
Any dos or don'ts as far as what he shouldn't wear or not wear? LoL!

Thanks for your thoughts

And your nephew borrowed all your disco clothes mmmmm you might want to keep a eye on those two, You won't have any clothes left for your son


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18 Responses to “My guy has been hinting that he might like to dress up as a lady for Halloween! It sounds like fun but I don’t?”

  1. Please…. there is no boyfriend. You are a guy, playing out a little fantasy you have. I am amazed at how often this happens here.
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  2. Just Joyce says:

    Ok Maria. . . don’t let it throw you ! ! LOL LOL It is only Halloween. . . and if he does turn into a cross dresser, look at the clothes you can share! LOL LOL LOL
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  3. doofus says:

    I have done it, not a big deal. Help him with the make up and jewelry and have fun.
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  4. Jackie Blue says:

    It’s Halloween. No big deal. Heck as a joke, my dad and some other men in the family dressed up as females for some adult parties and they all were a hoot. Dress him up like Dolly Parton. lol
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  5. Jan says:

    And your nephew borrowed all your disco clothes mmmmm you might want to keep a eye on those two, You won’t have any clothes left for your son
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  6. mamad says:

    my husband dressed up as a female one year for halloween, and it was hilarious. He was the ugliest woman I have ever seen! lol He wore a curly red hair wig, one of my dresses and cowboy boots. He had bright red lipstick, and very pink cheeks. He scared the men at our party half to death. It was a lot of fun.
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  7. dummymummy says:

    As long as he does not want to wear your good clothes, what is the harm. Have fun, help him have fun as well.
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  8. safety dawg says:

    guys do that for halloween quite often. and most people have a lot of fun with it. so let him do it and enjoy the laughs.
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  9. Sew What? says:

    It’s Halloween.

    My husband did this for a costume party many years ago. He won first prize.
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  10. WELL…. LET’S SEE NOW….

    One halloween, my girlfriend and I went to a party in our
    "cross-dressed-best" outfits. It was alot of fun…. except
    for those dang "HI-HEELS"…. whoever invented that CRAP
    must have been a real "woman-hater" from WAY-BACK !!!
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  11. shadylane says:

    just remember if you wear your boxer shorts under the dress it’s a halloween costume if you wear panties well you know
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  12. Cleo says:

    Years ago my husband dressed up as a lady and I went as a man. No one knew who we were when we arrived complete with mask and we remained non verbal.
    I might add that he is very much a man’s man. You know, all the man stuff, hunting, fishing, 4 wheeling, mechanic, you name it.
    Hey, if your guy is comfortable with it go for it.
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  13. joanaporter says:

    It’s great if you dress in a tuxedo and top hat.
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  14. Davey says:

    I approve only if he wears a placard that says "No on prop 8". Why doesn’t he go in black face? I think you know my thoughts. I wouldn’t do anything to get a reaction from others, especially if there will be drinking.
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  15. thinking says:

    ask him if he wants to do it
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  16. 'ol Geezer says:

    What the heck Maria, Why not ? Sounds like fun.(are you afraid he’ll look better than you ? Don’t worry, I seriously DOUBT that will happen.)
    And just imagine the looks on the drunks that reach under "her" skirt, and find something they just didn’t bargain for.

    "woooo, HAAAAAA ! ,,,,,,WTF’S THAT" ?

    As far as suggestions go, you might caution him to wear clean underwear, there might be a "stiff breeze" that night.

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  17. yammee says:

    Here in he U.K. halloween(if it exsists at all) is for the under 5s.No wonder you are in such a mess.
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  18. Cat Lady says:

    When we were first married, my husband said there was going to be a contest at work for the best Halloween costume. I had a trunk of costumes, and we fixed him up as a slightly PG bride. I did his make-up really nice, plenty of eye shadow, even a garterbelt and nylons worn with tennis shoes. I made this awful 1920’s veil, and a wig, and he wore this monstrous "diamond" ring. He won the prize!! It was a lot of fun for both of us!
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