Sex, Awkward and Underwear: Knockout

Knockout

By hwat? - 09/05/2022 20:00 - United States - Denver

Today, my girlfriend and I were about to have sex for the first time when she revealed her underwear: boxer shorts. She said she wears them because they’re the only underwear that doesn’t ride up her ass crack. Completely killed the mood. FML

I agree, your life sucks 376

You deserved it 4 716

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Same thing different taste

By fruitoftheloom - 09/03/2015 05:13 - United States - Scottsdale

Today, my girlfriend took off my pants for the first time. She was more impressed by the pattern on my boxers than by my cock. FML

I agree, your life sucks 37 966

You deserved it 7 323

Why would you do that?

By HughGorgy - 20/03/2009 05:37 - Canada

Today, after sex with my girlfriend, I thought it would be sexy to wear her underwear until we saw each other again. I found a pair in her bathroom, but they definitely weren't her sexy ones. Her mom walked in on me to collect the laundry and screeched, "What are you doing with my panties!" FML

I agree, your life sucks 17 386

You deserved it 103 231

By captainocd - 19/08/2010 19:16 - United States

Today, my incredibly self conscious girlfriend decided to get over her fears and let me see her in her underwear. She did a short strip tease, crawled on top of me and asked what I thought. I couldn't think of anything to say besides, "Your bra and panties don't match." FML

I agree, your life sucks 11 650

You deserved it 85 112

Magic underwear

By Anonymous - 10/01/2022 22:59

Today, my date decided not to have sex with me after she saw I wear Y-fronts, Tighty Whities to some of you, instead of boxers, so she couldn’t take me seriously as a grown man wearing underwear normally worn by children under 10 years-old. FML

I agree, your life sucks 1 244

You deserved it 2 780

By Anonymous - 13/07/2011 05:02 - United States

Today, my girlfriend, who is very self conscious about her body, finally decided to have sex with me. She told me to wait a few minutes, so I did. I stripped and turned around to find her in a one-piece swimsuit, with a hole cut out of the crotch. FML

I agree, your life sucks 81 742

You deserved it 8 517

By Eddie - 07/08/2011 19:43 - Israel

Today, I took my clothes off in front of my girlfriend for the first time. She made a weird face for a moment, then burst into laughter. She couldn't stop laughing, no matter how hard she tried. FML

I agree, your life sucks 41 903

You deserved it 4 923

By Lovenem - 16/02/2011 17:51 - United States

Today, my girlfriend said "It's funny how every time we have sex I'm wearing these panties." We've been having sex every day for the last six days. FML

I agree, your life sucks 53 350

You deserved it 7 112

Dealbreaker

By Anonymous - 17/03/2015 07:46

Today, my girlfriend dumped me. Not for cheating or for flirting, but because I wear tighty whities. FML

I agree, your life sucks 34 270

You deserved it 22 924

Creepy thing to do, for sure

By Anonymous - 11/12/2023 16:00 - Canada - Toronto

Today, my wife told me she wanted to try something that would turn me on immediately. While I was in our bed, she came in, wearing only the underwear she took from our 13 year-old daughter's closet. Now she doesn't understand why I'm genuinely disgusted and don't want to have sex with her. FML

I agree, your life sucks 685

You deserved it 156

By shit.... - 08/11/2012 18:25 - Malaysia - Kuala Selangor

Today, I was making out with my girlfriend, and things started getting pretty hot. That is, until I tried to remove her shirt. Somehow, I managed to grab her pajama shorts and give her a violent wedgie. FML

I agree, your life sucks 19 636

You deserved it 31 360

TeaTimeAbyss 20

Tuesday 10 May 2022 4:03

You sound too immature to have sex

VintageReddress 13

Tuesday 10 May 2022 4:37

You don’t deserve to be having sex if you have a problem with her wearing boxers. First of all, they are incredibly comfortable, and second of all, her underwear absolutely does not need to turn you on. Please grow up.

Comments

Justkidding100 41

Tuesday 10 May 2022 15:46

you realize you take them off to have sex right?

wrenavery90 12

Tuesday 10 May 2022 21:56

Seriously? How could that possibly matter?

CowgirlWithHeart 15

Wednesday 11 May 2022 0:32

Why dont you get yourself a pair of ladies panties and wear them for a while and see how uncomfortable it is to have them riding up your butt. Somewhere out there is a guy who would remove those boxers with his teeth, and be happy to do so and if you're going to diss her for those boxers she can just go find him.

DanielleinDC 33

Wednesday 11 May 2022 0:45

You're upset because she wears comfortable underwear? How hard is it to take them off her and toss them to the side? YDI. Hopefully she can find someone more mature who doesn't care what underwear she wears.