Miscellaneous: Today, as a joke, my friends and I decided to put me in a dress...

By twitch01 - 09/08/2009 07:31 - United States

Today, as a joke, my friends and I decided to put me in a dress and makeup, to creep out a friend. I'm a guy. I'm not sure which is worse, the fact that I so willingly volunteered to wear the dress and the makeup, or the fact that I thought it was comfy and made me look slim. FML

I agree, your life sucks 14 772

You deserved it 54 386

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Same thing different taste

By Anonymous - 01/11/2014 05:47 - United States - Queen Creek

Today, I dressed up as my friend for Halloween. He has a very distinct style and I thought my costume was pretty clever. When he saw me, he said he had never been so offended in his entire life, and now I feel like a complete asshole. FML

I agree, your life sucks 32 547

You deserved it 16 564

By Allycat - 09/10/2013 01:19 - United States - Ronkonkoma

Today, I was working a kid's birthday party dressed as a clown. The child's mother made me change because he was scared of clowns. The only thing I had in my car was a princess costume that was owned by a girl co-worker. So for 4 hours I had to entertain in a tight pink dress. I'm a guy. FML

I agree, your life sucks 47 167

You deserved it 5 114

By Apple - 12/06/2011 17:54 - United States

Today, I was at my friend's house, and I asked if I could try on one of her dresses. It was a little snug, but I got it on. When it came time to take it off though, it wouldn't budge. My friend and her mom had to cut it off me. FML

I agree, your life sucks 19 513

You deserved it 34 843

Be careful what you wish for…

By Sady_Ct - 15/05/2019 12:12

Today, I caught my husband trying on the sexy bra I bought to wear just for him. For shits and giggles, I made him try on my dress too. He looked better in it than I do. FML

I agree, your life sucks 1 540

You deserved it 561

By what - 26/11/2010 19:17 - United States

Today, while shopping, a few giggling girls came up to me and asked why I was wearing a dress in public. Highly confused, I didn't answer. When they walked away laughing, I realized they thought I was a man. I'm a woman. FML

I agree, your life sucks 37 473

You deserved it 4 165

Nostalgia

By Fatty - 06/05/2009 15:04 - United States

Today, I was excited about my friend going wedding dress shopping, so before I went to go work out, I decided to try on a prom dress from high school to remember what it felt like to get dressed up. It was too tight, I broke the zipper, and spent 45 minutes trapped before I cut myself out. FML

I agree, your life sucks 21 579

You deserved it 41 582

By preggersmcgee - 22/10/2012 16:09 - United States - Nixa

Today, I finally found a cute dress that hugged my curves and hid my imperfections. I wore it to my friend's house, and was feeling pretty good about myself, until some pregnant woman walked into the room wearing the exact same thing. It was a maternity dress. FML

I agree, your life sucks 29 643

You deserved it 7 281

By bride - 14/02/2011 06:24 - United States

Today, I dreamed I was getting married. I was wearing a white dress, had incredible cleavage and perfectly done makeup. Just one problem. I'm a guy. FML

I agree, your life sucks 53 032

You deserved it 10 079

By ssondik - 22/06/2015 00:50 - United States - Hebron

Today, I was invited to a fancy-shmancy charity event, and the host - my friend - told me to wear a long, ballroom, fancy gown. Turns out my friend was just being a dick and it was a pool party. I spent $200 on my hair and makeup alone. FML

I agree, your life sucks 29 109

You deserved it 5 182

By matish - 20/09/2018 13:30

Today, despite having long hair and wearing makeup and a dress, I was still mistaken for a man several times. I'm a girl and I was born a girl. FML

I agree, your life sucks 3 013

You deserved it 198

jmeg_fml 0

Sunday 9 August 2009 15:56

i never understood why girls could wear guys' clothes but guys couldn't wear girls' clothes

dralligator 1

Sunday 9 August 2009 16:00

I once had to cross dress as part of a play. I felt so comfy in the dress. XD Most guys just won't understand.

Comments

love21_fml 0

Monday 10 August 2009 8:46

Lmfao. Fyl.

jw987654321 0

Monday 10 August 2009 9:02

don't worry about it man, so long as it doesnt become a habit...i mean, at my graduation after party thing we had a drag contest and me and all the other guys got pretty into it...like, makeup, stuffed shirts, everything...it was pretty hilarious, and definitely didnt mean that any of us are gay

zargon 1

Monday 10 August 2009 11:34

And what if he does make a habit out of it? Do you think that'd be a problem? Because you certainly imply as much....

kellster 2

Monday 10 August 2009 10:01

Omg, these answers are all so stupid!! OP: everyone looks better in make-up. We just have a huge taboo about only letting women and gay men wear it (and even then, the latter get weird looks, too). And if it was a comfortable dress that made you look slim, why wouldn't you like it? This has nothing to do with your sexuality. Women's clothing (and make-up) is more varied and therefore mysterious to the half of the population that don't get to wear/use it. Obviously it's intriguing. If it turns out you want to wear it more often, so be it. If it turns out that you also discover that you like having sex with men, fine, but that has nothing to do with this. Meanwhile, everyone take a pill and relax. :)

charmedlife 0

Monday 10 August 2009 11:58

ah... the thrill of crossdressing... sounds like you've been wanting to try this for the longest time... ;)

My_averageFML 0

Monday 10 August 2009 13:27

I agree with #111.

Deemon_Cat 0

Monday 10 August 2009 13:46

lol What's so bad about this?? You looked slim and it was comfy, so what if you're a dude??

fortywhacks 0

Monday 10 August 2009 17:36

I agree with #113. Not an FML. But FYL that you've been raised to be so narrow-minded you consider this an FML. It's hot when guys wear clothes that look good without giving a damn about whether they're "male" or "female" clothes. Like Noel Fielding.

wroteyouoff 0

Monday 10 August 2009 19:16

I'm a girl, and I feel great in guy clothes. It's not a crime.

Rho_fml 0

Monday 10 August 2009 23:46

It's lots of fun, you should try it more often, you obviously liked it at least a little, now you can explore something most people are too cowardly to ever do. =)