Bad to Worse

by A person
(Free Contry, USA)

I always had trouble making guy friends, so in high school many of my friends were girls. One night, we'd had dinner at Beth's house, and were hanging in her basement, when she suggested truth or dare. Most of the girls were enthusiastic, so I got pulled in.


The game was pretty tame for a while, but as the evening wore on they got more and more adventurous. At one point, I got dared to let Amy put makeup on me. I consented, and the game paused briefly for them to all watch as I was seated on a small stool for Amy to work her magic. I was told to hold still, and couldn't really tell what was happening.

A few minutes in, another girl (Beth, I think) asked me to stretch out my right hand. I absent-mindedly complied, and felt something cold on my finger, and realized she was polishing my nails. I protested, but the girls unanimously (surprise) decided that nail polish was part of getting a makeover.

Amy kept up her work on my face, and Beth managed to paint all my finger and toenails bright pink. Somewhere along the way, someone had found a wig (blonde), placed it on my head, and did some tugging which I couldn't really see.

At long last, Amy declared her work done. I was ordered to close my eyes as I was lead to a full-length mirror. I opened my eyes to find myself looking, well, maybe not quite like a girl, but definitely not like a boy. My face looked...softer. I was wearing bright pink lipstick the same shade as my nails, and "my hair" was done in two bunches held in place with small pink bows.

The girls giggled like they'd never stop, telling me how cute I looked and how pink really was my color. They kept cajoling me to thank Amy for what a good job she did. I tried to salvage some bravado from the situation, and tried to pull off some heavy sarcasm "Thanks, Amy. My makeup looks really cute, and I'm sure the pink will really go with my dress for the dance."

Mistake. They all looked at each other, and after a few whispered conversations Beth and two others raced upstairs, while the others held me gently on my stool and grinned silently.. I tried to get something out of them, but got nothing until Beth returned, grinning ear to ear with a garment bag.

She smiled at me, and Amy thanked me for the compliment, but just to be sure I should try my dress on to see. I looked puzzled until Beth pulled a pink chiffon party dress out of the bag. I struggled quickly to get away, but the girls held me down.

I pointed out that wearing girls' clothes wasn't part of the dare. They laughed, and pointed out that wearing a dress had been my idea - they were (they claimed) just helping me make sure the makeup would "go with my dress" as I'd wanted.

I pointed out it wasn't "my" dress, so it didn't count. Beth countered that it was part of a set of hand-me-downs passed on by an older cousin, and it didn't fit her right, so she was giving it to me. It was clear to me there was no getting out of this, as I was badly outnumbered and they were very determined.

As you've probably guessed, I spent the rest of the night in "my" frilly pink dress, tights, and borrowed girl's undies. After I was dressed and christened "Sara," the game resumed mostly as normal.

At the end of the night, I told them they'd had their fun, and asked for my clothes back. Grinning, they told me that I was wearing my clothes, as the dress had been given to me and so was now "my clothes."

Eventually, I convinced them to give me back by boy clothes so I could go home, but they demanded in exchange that I'd agree to be "Sara" and wear my dress for the Halloween dance (4 weeks away). But that's another story.

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Dec 01, 2014
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Cute
by: Anonymous

Sounds like you enjoyed yourself, Sara. Hope you had fun at the dance!

Dec 20, 2014
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So good. So evil. Great fun!
by: Francis

Absolutely loved the way you told your story! At the point where you were sarcastic I was all like "no, you didn't go there!"

Well you did.

And mad props for following through with the dare! I mean, you could have just run away. But I am 100% sure it was more fun this way.

And it doesn't even have to do anything with you not being manly or such nonsense. You have fun. You were true to your words (well those that were a bit forced on to you).

And if you pull off the dance and stay cool about it, perhaps even trick a few people into thinking you really are a girl... Well, I could imagine this being pretty impressive.

Just be sure to return the favor with a similarly heavy handed dare to the girls next time.

I am thinking wet T-shirt contest, having them obediently serve you (drinks and other things) and the like!

Honestly, you are more courageous than I am! (Not that I didn't already have my share of makeover, but that is also for another time ;))

Mar 18, 2015
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Tempting Fate
by: Anonymous

You should have decided cut your losses when you were "just" in a ponytail and makeup. That's what you get for tempting fate! You deserved everything you got, *Miss* Sarah.

Did you wear the same dress to the dance, or did they put you in a girlie costume?

Apr 23, 2015
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Such a cute story!
by: Anonymous

You're a good friend and a brave boy for going through with all that. I think it was a little mean of them to make you dress up for the dance, though. Unless you were enjoying yourself, anyways ;)

I'm a little jealous of your friends. The closest I've come to this is getting a guy to wear lipstick for half an hour. There's no way I'd ever get one of them into a party dress and full makeup.

Hope you came up with something really evil to get them back with!


Jul 13, 2015
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I wish!
by: Anonymous

Gosh, I wish a girl would do that to me!

I think most boys would love an excuse to try wearing a pretty dress some time if they'd just admit it.

How did the experience make you feel, Sara? Did you go through with the dance?

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