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 14 766

You deserved it 54 380

May Day: Lily of the Valley and Misunderstandings
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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 32 544

You deserved it 16 552

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 47 161

You deserved it 5 107

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 19 509

You deserved it 34 826

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 1 511

You deserved it 545

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 37 461

You deserved it 4 157

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 21 575

You deserved it 41 566

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 29 629

You deserved it 7 275

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 53 025

You deserved it 10 075

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 29 096

You deserved it 5 177

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 3 009

You deserved it 196

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

Arikata 0

Tuesday 11 August 2009 20:35

Nothing wrong with this in the slightest. I've crossed dressed a number of my straight friends and they enjoy it. Most transvestites are actually straight, they're just better in touch with their feminine side. Putting on make up and a dress doesn't have to mean any thing. Though if you have been looking at men that way, there is nothing wrong with that either and the people on this site need to shut their homophobic asses the hell up. Though, if you just don't feel right in your own skin and you long for the "female role" in life maybe you should do some research into transgenderism. Though from the sound of this post I bet you're just a guy who enjoys delving into his feminine side now and then.

unhacked21 0

Wednesday 12 August 2009 0:34

okay...the bad part isnt being so willing to do it. under other circumstances, i'd say it wasnt gay, and ur just comfortable doing it knowing u wont find it nice to wear...but u do, so gay.

yowzerz 5

Wednesday 12 August 2009 2:54

Haha that's cute.

kaylaella 0

Wednesday 12 August 2009 9:52

LMFAOOOOOOO !!

lazorzpewpew 0

Wednesday 12 August 2009 19:38

I could dig a kilt - a nice breeze on my balls... mmm....

b_u_n_n_y 0

Thursday 13 August 2009 15:30

Had a friend crossdress for Halloween...He told me how much the costume cost and my jaw nearly hit the floor! He replies "Well, I couldn't go walking around like a CHEAP *****...and this Victoria's Secret stuff is comfy..." lol. Kudos to you! Women sure know how to dress comfy and still look daaaamn good :)