Karen – I Dare You


I dare you. Those were the magic words to trigger Karen’s challenge button. All you had to do was to come up with an interesting challenge, and she was in. She was not doing it for the money, it was just for the fun of it, for the rush of adrenalin that comes with daring challenges.

But she was not stupid. To someone who dared her to jump off a bridge, she said:

“Hey, I might be crazy, but I’m not suicidal.”

She had a great personality and she was fun to be with, so she had many friends. Many challenges came from them, from climbing a mountain face bare handed to kissing the next guy turning the corner.

It was Friday night, and they were out dancing in some club. She was having a good time with three of her friends. Karen was wearing stretch jeans and shoes with a two inches high heel. Suddenly, Lynda looked at her, with those eyes which Karen knew there might be a challenge at the end of it.

“Say, Karen. Those jeans are quite pretty.” said Lynda.

“Thanks Lynda. I bought them today. Tight but comfortable.” She said as she rubbed her hand along her thigh.

“This? Tight?” said Lynda. “I have an aunt that was a teenager in the 80’s, and she showed me pictures and believe me, these are NOT tight.”

“Are you challenging me to wear tight jeans from the 80’s? That’s an easy one.” Said Karen.

Lynda smiled devilishly.

“Are you up to the challenge? Okay, here’s the deal. My aunt said that she bought her tight jeans by taking her measurements and going two sizes smaller. That’s how we’ll do it.”

“Ha! Don’t bother taking my measurements. Take the size of these jeans and remove two sizes.” Said Karen.

“Correct me if I’m wrong, but these are already smaller than your regular size.”

“ You got that right, Lynda.”

“We’re talking about non-stretch jeans here. Not average stretch ones.”

“Yes, I know. No big deal.”

It was getting better and better.

“Really? Okay, here’s the full deal: You will wear those jeans, three sizes smaller. You will wear four inches spiky heels with that. We have already something planned for the weekend: our white night. You will wear that outfit for the full 36 hours, and participate in all the activities we have already planned. Are you dare?”

“ That’s child play.” Said Karen. “You bet I’m in.”

The deal was sealed with a gulp of beer.  As with all her other challenges, the instigator of the challenge had to pay for all the fees, so Lynda had to buy the jeans and the shoes.

Saturday morning, the four of them all met at Karen’s place. There, Lynda put the bag of clothes on the table, along with some pliers, pretty weird looking.

“What the heck are these?” asked Karen, picking the pliers that had very long but narrow steel jaws, covered with tiny and sharp spikes.

“My aunt told me that to put jeans as tight as the ones you chose, you’re gonna need theses.?”

“Whatever. Shall we begin? I can’t wait to laugh in your face.” She said, confident to meet the challenge in a breeze.

Karen led the way to her bedroom. She removed her bathrobe to reveal her fine bright red satin underwear. Lynda got the first garment off the bag: it was a spandex bodysuit, white, with long sleeves.

Karen laughed as she put it on. It was very tight fitting and was struggling to put on, but it was stretchy.

Next came the jeans. Karen looked at them. They were Guess non-stretch slim fit jeans. A quick look at the label confirmed to her that they were in fact three sizes smaller than her regular size. Still smiling, she put her legs in them and started to pull, and slowly, she lost her smile.

“There’s no way I’m gonna fit in those. It’s way too small.” She said, the jeans apparently stuck at her hips.

“Are you chickening out?” said Lynda. “My aunt said that that’s what she wore back in those days. Three sizes smaller was the tightest she was ever able to put on.”

“Well,” said Karen, starting to jump in place, pulling on the jeans, “if your aunt did it, I can too.”

It was a heck of a struggle. She had to use all her crazy moves to pull the jeans on. At one point, two girls were pulling on the waistband, lifting her off the ground while she was wiggling to sink through.

Finally, with everybody exhausted, the crotch seam was as high as it could go.

“All that is left to do is to close them.” Said Lynda with not one, but two pairs of the strange pliers in her hands.

The pliers were ratchet-like. She first took a string and looped it into the zipper handle, and straightened the string upward. She then took the first pair and applied it at the base of the zipper, then took the second pair and applied it at the top of the zipper. That loosened somewhat the bottom end, which allowed the first pliers to be able to tighten more, then the top one, and so on, until the zipper was practically closed.

By then, Karen had wide eyes and was breathing in short gasps.

“That’s awfully tight. I’m afraid the jeans will rip in half.” She said.

“No way, Karen. These jeans are MADE to be worn tight.” Said Lynda, giving the pliers one more squeeze.

She easily took the string and pulled up the zipper, and finally attached the waist button, before releasing the pliers.

Karen could not believe how hot tight these jeans were. She already had wide eyes, and she had wider ones when she saw the footwear: white platform boots with a spiky 6 inches heel!

“What the heck are those for?” she asked.

“You agreed to wear four inches heels. The platform has 2 inches, and the heel 6, which resumed to a four inches heel.”

“Yeah, whatever, but why the boots?”

“For two things: First, sandals are skimpy, and you’re bound to break the ankle strap pretty fast, thus having an easy way out of it. Second, you’re gonna need all the support you can get, and the boots will provide that extra support at the ankles.” Said Lynda as she proceeded to lace the knee high kid leather boots.

Once done, she rolled down Karen’s tight jeans over the boots, and offered her a hand to get up the bed. She was stiff, and rose up pretty much like a wood plank.

She was panting, wide eyes. She was slowly rubbing her hands along her tightly encased legs, feeling the side seam, bursting out, ready to explode under the pressure. She felt the stitching with the tip of her nails. That sent strange vibrations. Disturbing vibrations.

“Okay, come on Karen, it’s time to go.” Said Lynda, picking up her purse.

 Karen followed. It was an all new experience. She never wore heels like that, and never wore anything as tight. She had to struggle just to get from her apartment down to the parking lot.

Getting into Lynda’s small car proved to be a challenge, even though she was sitting up front. She had incline the backrest, for the duration of the trip to the amusement park. That’s where they had planned to spend the weekend.

Once arrived, she had to stay put by the car for a good fifteen minutes for the feeling to get back to her legs, then she was up to the amusement rigs. It wasn’t long before the tight jeans, massaging her buns and crotch, got her to feel some disturbing sensations: she was getting aroused!

They walked the park, and chose rides. Karen preferably chose rides where she had to stay upright as much as possible. But the sensation was always the same: awesome. Especially when the restraint system involved a crotch strap! That was a blast.

Of course, she was looked at quite a lot. This was not exactly the perfect outfit to wear at an amusement park.

By the end of the day, she was exhausted, her feet were hurting, her hips were hurting, everything was screaming for release, but she had made a challenge, and she was not about to let go, especially for something as simple as tight jeans… sexy, arousing, astounding, extremely tight jeans.

They had dinner at the amusement park then it was off for more rides. Karen took as many as possible, secretly hoping that the jeans would give away, rip open, and give her some release, but they remain solid. Not that it was a really bad thing, she was really starting to appreciate them.

The amusement park closed by midnight. They headed for a nearby club, where they danced and partied the night away.

After a nice breakfast, it was the ride back home. To make sure Karen wouldn’t sleep it over, Lynda had the (brilliant) idea of making Karen drive. It was not easy, as tightly encased as she was, to work the clutch. Yes it was difficult, but each move of her leg, lifting the knee, was arousing as hell!

Finally, they were back home. Karen still had to spend a few hours in the tight jeans. They simply relaxed in Lynda’s backyard. Karen was quick to doze off, but the other watched in amazement as she unconsciously brought her hands to her crotch and started to make small circles.

End of the day Sunday. The dare had been met and Karen was glad to get out, so she let everyone believe.

The following week, they met regularly, and Karen was back into her stretch jeans, then by the end of the week, started to show up in non-stretch jeans that were rather tight, until finally, on the usual Friday night at the dance club, she showed up wearing the same tight jeans she used for the dare and of course, the high heels boots.

“Wow!” said Lynda. “Did someone else challenge you for the weekend?”

“Nope.” Said Karen. “I wear them for my own pleasure.”

And she did, for the whole weekend, and the one after that, and the one…

© Pete / monsterp63, August 2005

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