What is the worst mistake you've ever done wearing a skirt?

[Samantha31606]

Mine was wearing a flowly kinda above the knee skirt in 28 MPH winds.

[KrisPW]

Highschool boyfriend was always daring me to do the whole commando in a skirt date thing. We'd been naked together, and done the things one does when naked together. But I also try to stay out of trouble so always told him no. Fast forward a few months. "Hey, want to spend my birthday with me?" Of Course I did!

Getting dressed while he was coming to pick me up, I decided on a whim, now or never, and ditched the panties. Happy Birthday boyfriend!

I waited for him on the porch so he wouldn't be subjected to the harassment of my brothers before we could leave. Got all excited hearing a car coming up the road. Until... THEY turn in. To my horror, it wasn't going to be the birthday date I had expected. His entire family was with him. Parents, young brothers, grandparents to meet us there.

I tried to tell him I needed to step in for a minute but he insisted we had to go... I would have explained, but his mom would have heard, so I just got in the car and VERY carefully climbed in. Apparently the day would include breakfast with the grandparents, afternoon at the theme park, and dinner to top it off. OMFG... shoot me now.

Somehow I managed to make it through breakfast with no-one the wiser. I still couldn't get him alone to explain though, and then things took a turn. I don't know how much was seen for sure, but his brother must have gotten a peek of more than he expected as we got back in the car. He went from excited 12 yo that can't stop talking, to suddenly mute. He whispered to his brother in the back seats the rest of the way. I thought I would die and my boyfriend was just giving me funny looks the whole time. We get there, get through the lines, and into the park. Asked boyfriend to take me to the bathrooms and was finally able to explain my problem on the way. After laughing hysterically, and checking my credibility with a discrete feel, he said he would try to help, but didn't know what we could do. Parents still in the dark, boys following my every move. I don't know if they ever got their prize, but they sure seemed to be looking for every opportunity.

Suffered through half the park before we were in a gift shop and I found my salvation. Hallelujah! There were a pair of shorts on the rack. Bought them and made a dash to the bathroom to change. His dad didn't seem pleased, his mom didn't know why I had to wear them now when my skirt looked so cute, but I wasn't missing my chance. The boys, no longer hopeful, quickly wanted to go do other things, leaving with mom. Spent the next hour with boyfriend and his dad, but at least I was covered for it and was able to relax and have fun. The rest of the "date" was uneventful thankfully.

[Samantha31606]

At least your boyfriend helped! This is why I never in my life will do commando, too risky and who knows what will happen, little sad that your boyfriend never told you that he'll be bringing his family with him, but at least they'res a happy ending!

[pamela1]

The majority of my skirt wardrobe is flared, and there have been plenty of times it blew up in the wind. The embarrassing ones are when the wind is so strong that the whole thing goes up above the waistline 🤣. I think the worst mistake for me is when I was wearing a micro mini dress. Of course, I and my clumsy self decided to bend at the waist giving a full show to everyone behind me lol, but the worst was after I stood back up, I went to grab what I thought was the hem of my dress, but I pulled my panties from the leg band instead. I was like omg, so I had to lift my dress up and pull up my panties back into place 🤦‍♀️

[Samantha31606]

When my skirt goes above the waistline from the wind, I just give up trying to keep it down since you push it back down then 6 seconds later, it's flying back up, and I really don't like wearing any types of dresses, so I cannot relate at all to the dress and panties situation, but it's embarressing when you pull the wrong thing, that always sucks

[pamela1]

The mini dress that I was wearing was very popular in the 80s and 90s but I forget what it was called. The bottom was flared and gathered at the waistline. It was 10 inches from the waist, so it barely covered my butt, but yeah, lol. I laugh about it now and enjoy telling my mishaps 😂

[Samantha31606]

Ok, since it was barely covering your butt, that just spells disaster lol, at least you laugh about it now.

[FlyUnzipped]

Well let's hear some more lol yeah you gotta make sure your butt is covered haha oops!

[Wish4UrB00ty]

I feel for you girls!! Skirts are so fun and so sexy but they can bring such bad mistakes. I had a girlfriend how loved her skirts until I got it in my head that I could go up her skirt whenever I wanted… she stoped wearing skirts around me unless she wanted something from me.

[Samantha31606]

Skirts do have they're pros & cons, but why did you get the idea that you could go up her skirt whenever?

[Wish4UrB00ty]

Well that was the mistake that I’m still kicking my self for…

[Samantha31606]

Ah, at least you know that was a dumb idea.

[Wish4UrB00ty]

I do! And I learned a lot from that relationship.

[Samantha31606]

I wish you luck on further Relationships!

[Wish4UrB00ty]

@Samantha31606 thank you!!

[Samantha31606]

No problem!

[Pete671]

Answered the door to my neighbour in a pink tartan miscroskirt that I forgot I was wearing lol,,,

[Sour-rose]

wearing a thong on a windy day. Don't get me wrong, I crave a windy day so I can wear a skirt because my butt and legs are chisled. ;D But wearing a thong on such a day so everyone can get a real good show is not my intentions. I want folks to see how cute my underwear is, not how nice my ass is. :x

[Sirenboobzilla]

While on vacation, I had run out of clean underwear so I went commando in this skirt I really liked. Didn't realize how windy it was going to be. I beaved my boyfriend's family a few times. It was the first time meeting them 😵‍💫 luckily though that laughed... they still bring it up today >_>

[Samantha31606]

I wouldn't dare even going commando in a skirt ever, very brave of you! Wind does kinda do that sometimes, do you even like it when they bring it up from time to time?

[Sirenboobzilla]

I was completely out of underwear and didn't get to do laundry. One of those times when you're rushed and you forget to do stuff. We're at this hotel in Buffalo, NY so we're hours from home. It was all just the perfect recipe for an oops moment.

It doesn't really bother me. They more just pick on me a little bit, but it's all in good fun. It's given his mom an excuse to make beaver jokes

[Samantha31606]

That does make a huge oops moment, and I understand the rush thing, you think you got everything done besides 1 or 2 things, and being hours away makes it 500 times worst.

At least it's in good fun, and interesting that it gives your mother an excuse to make beaver jokes.

[FlyUnzipped]

Omg you flashed the vag to them hahaha damn

[susie22]

Wearing a very short pleated flippy miniskirt on a very windy night out with my boyfriend to an oceanfront restaurant going commando.

[Wish4UrB00ty]

Oh no!!! 😂😂😂 so fun and sexy until it went so wrong… 🤦‍♂️😊

[Samantha31606]

Honestly, wearing a miniskirt while being by the oceanfront just spells disaster, especially if your going commando, but was the restaurant at least good?

[susie22]

@Wish4UrB00ty Lol, my guy was with me, and he's a bit over 6'6", so I don't think I'd have any problems, besides, it was his idea!

[susie22]

Yes, it was REALLY good, we've been there a few more times since. Not cheap, but worth the $$$.

[pamela1]

@susie22 I’ve done that quite a bit back in the day every time I went to the boardwalk at a beach resort, except I had on my underwear. You would think I learned my lesson after it happened the first time, but nope, i just kept wearing them lol

[susie22]

@pamela1 My boyfriend loves it when I do that, I guess it kinda turns us both on, lol.

[Wish4UrB00ty]

@susie22 I think it is usually a fun turn on for most guys. It just depends on how the girl feels about that much exposures. If you enjoy it too then it sounds fun!!

[susie22]

@Wish4UrB00ty I do go braless most of the time (if not all) when we go out, but commando, not so much. I reserve that for "special occasions", lol.

[Wish4UrB00ty]

@susie22 😂😂 special occasions are fun!!

[Caramelpie]

Getting extremely wet and horny on a date with my boyfriend at one of the restaurants and well it was obvious for anyone to see when we left.

[Anonymous]

Fell off a bar stool. Not one of my most dignified moments.

[Samantha31606]

That's good

[ilovepinknipples]

Wearing skirts makes women look very noble.

[Samantha31606]

Not gonna lie, the word "Noble" makes my brain confused, explain it a little more?

[ilovepinknipples]

I mean they look feminine and cool

[Samantha31606]

Ah ok

[es20490446e]

Forgetting that only women can skip underwear.

[FlyUnzipped]

Haha I bet that skirt was all the way up over your waste lmao. What kind of panties were you wearing?

[Rathoreshivraj]

Then what happened 😁