Karen – The First Story (With High Heels)


It’s the “first story” but with Karen having to struggle with high heels in addition to her tight jeans. Written/updated in 2012.

Part I

I’ve been with Karen for about a year. We moved together roughly 3 months ago. I was pretty proud of her. She was smart, had a great personality and a killer body.

Nevertheless, she didn’t dress provocatively, or very sexy. She had a couple of trim fit jeans and short skirts, but she was pretty much the “middle of the crowd” dresser. Nothing to draw attention to her physique.

The other day, she came home with a pair or snug fitting stretch jeans. A first for her. She put them on right after dinner, and let me have a look.

“What do you think?” she asked.

“Very nice,” I said, “but it would be even better if they weren’t stretched”.

She stared at me, startled.

“You really mean that?”


“Well,” I said, a little embarrassed, “I do like a woman’s butt in tight jeans”.

“Oh really,” she said with a smile. “I’ll think it over”.

We washed what was left of the dirty dishes, and the subject wasn’t brought back. I did manage to have a great look at her butt, taking great care to hand her pans that had to go in the bottom cabinets. I just loved to see her nice ass in that tight fabric… and she made her best to tease me with it…

The next day, when I came home from work, she called me as soon as I entered the house.

“Hi honey. I’m in the bedroom. Can you come, I think I need some help.”

So I went. I almost froze at the door. She was laying on her back, on the bed, a pair of blue jeans up to her hips. They looked very, and I mean very tight. I must have had a pretty funny look, because she started laughing.

“Don’t stand there, help me. I went back to the store today to pick a pair of tight, non-stretch jeans, like you said you liked. I tried one pair, and it was a little hard to put on, but I managed. I came back to the counter and paid, but I think the lady mixed up my jeans with someone else’s because those are much smaller than the one I tried.”

“If you can’t fit in them” I said “why don’t you simply go back and exchange them.” Of course, I was hoping for the answer she was about to give me.

“Well, ” she said with a wink, “you said you liked a woman’s butt in TIGHT jeans, so I think I’m gonna have a try. Wanna help?”

“Sure, of course”. I was having a hard on, just to think about the look that will be obtained.

I helped her get up from the bed, then grabbed the pants by the side, and pulled as hard as I could, while she was slowly “jumping” to help get up. When it seemed to stop, we rubbed up each leg, getting as much slack as possible, if there was such a thing left. Finally, the crotch reached the highest point, and came the process of zipping them. It was obvious that it wasn’t going to be easy. I came back with a pair of long nose pliers, and I lowered Karen on the floor. I told her to let out as much air as possible from her lungs, suck in her tummy and try to pull as hard as she could on each side or the zippers while I close it. It took four attempts to get the zipper fully closed. After that, closing the waist button was just a formality. Every seam wanted to rip apart.

“Boy, this is tight,” she said. “I have difficulty breathing”.

I helped her get up. By that time, I had a real hard on, and she noticed it, rubbing it gently with her hand.

“That really pleases you, hey?

“Yes it does!” I said, looking at her butt. 

She made a few steps. There wasn’t any wrinkle from just over the knee to the waist. Only a small crease under each bun as she walked. She actually had to rock her hips to get one leg in front of the other.

“Wow. That feeling is stupendous! I like it! But I don’t think I can go like that in public.”

“Why not?”

“Well, for one thing, I can’t sit, and I can’t go to the bathroom alone”.

“Like I said, you can get them back, and have a slightly less tight pair…”

“Oh, I’ll definitely get a less tight pair, but I’m keeping this one. It will be my around the house jeans.” 

I couldn’t be more pleased.

“So, now what?” I asked.

“I can’t eat, that’s for sure, so while you’re having dinner, I’ll find something to do.”

And she did find something to do. I fixed myself a quick sandwich. Not that I wasn’t able to make something more extensive, but because I didn’t want to miss any of the shows she was putting on.  She decided to do a little dusting, walking, turning, bending, all making sure I was on the front seat to see it all. She really seems to enjoy it… and seeing my face!

After a while, we both sat on the sofa for some TV watching. Well, I sat, she leaned on the couch. I slowly rubbed her thighs. I could feel the jeans, tensed to the breaking point. It was rigid. 

“You know what looks good with that?” I said.

“No, but I got the feeling you’ll tell me.”

“High heels”.

She raised her eyebrows.

“Really” I said. “Tight jeans and high heels go well together.”

She never wore high heels, saying that it was bad for the feet. To my surprise she answered:

“I’ll think about it.”

The next day, when I came home, she called me again in the bedroom, and we had that same exercise of putting the jeans on. After that was done, she went to the other side of the bed, then kind of stepped on her toes. She walked back wearing four inches heels pumps.

“That’s making walking all the more difficult. The stiffness of the jeans and the heels. Work with me if I don’t look very sexy while I get used to all this.”

“I’m not complaining at all. You’re gorgeous!”

The next few weeks went like that. She was wearing the tight jeans and heels all the time at home. She kept cleaning the house in them. She even helped me renovate the basement dressed like that. It was very hard for me to concentrate on the work while watching her struggle to get up the ladder. She was getting quite used to the heels, so much that she started to wear them to go shopping, while wearing one of the more “street wearable” tight jeans. 

Some of my friends came to me asking if I had a new girlfriend. They simply hadn’t noticed her before. And to her great pleasure, she was getting compliments on her figure! One more push to keep dressing like that. And I wasn’t complaining. No sir!

One day, I came home with a little package I had ordered from the internet. With a funny smile, I showed it to them. She went wide-eyed as she took the leather tubes from the box. They looked like lacing military boots, but the sole had a wedge platform of at least 5 inches including a sole of half an inch, making the “real heel height” 4.5 inches.

“What the heck are those?” she asked.

“Hiking boots.” I replied with a of course tone. “See, the sole is made of thick soft rubber and has a grippy thread to it.”

“Come on, this is unrealistic.” She said, but at the same time, she was kicking off her pumps and putting the boots on.

“Wow! Very cushiony. Comfortable. I may like them. Much more stable than my pumps.”

“So you would wear them for our hiking trip?”

“In your dreams!” she said, pushing me away and walking away, wiggling her butt in her tight jeans, enjoying her new heels.

Last weekend we went for the mentioned hiking in the mountains not far away. Of course, she wasn’t wearing her tightest pair of jeans, nor her heels, for obvious mobility reasons. She was wearing stretch snug fitting jeans and hiking boots. It was a two day trip. We go up the mountain, sleep in the tent, and come back the next day. 

The weather was splendid. We reached the higher point, set up the tent, and made a small campfire. We spent a romantic evening, talking about the future of our relationship. Once in the tent, we got undressed and ready to sleep, but she started to goof around, taking my stuff, and throwing it out of the tent. I played along, doing the same with her stuff. Then I stumbled on some heavy items.

“What the…” I said as she ripped the bag out of my hands.

“That’s nothing!” she said.

“Those are the high heel hiking boots. You bring them?”

“Well, yes. I don’t know why.”

“Put them on. It’s not like we’re going anywhere.” Showing with a broad gesture that we were half naked.

She put them on and saw my immediate hard-on. Well, the rest, you can imagine. By the end of it, we were too exhausted to pick everything we’ve thrown back out so we decided to leave everything outside, and go to sleep, taking care of it in the morning.

In my excitement, it seems that I had thrown stuff a little farther that I had planned. The result is that her jeans landed on the fireplace. Although the fire was out, it was at the time hot enough to ruin the jeans. 

“Bah, don’t bother” she answered my demand of forgiveness “That was the stretching ones anyway,” she said with a smile. “I have a spare one in my bags.”

She reached for her bag, opened it, made wide eyes, and I heard a distinctive “shit” coming out of her mouth.

“What’s wrong? Forgot to pack them?”

“No, I do have them. That’s the tight ones”

“So, not such a big deal. They’re just a wee bit tighter than the ones you had.”

“No” she said, “I have THE tight ones! And… Where are my hiking boots?”

They had rolled down a gentle slope to the left of the tent. I went to retrieve them.

“Uh-oh…” I said.

“What, what’s wrong?”

Obviously, some rodents had a ball with them, chewing them away in a way that was rendering them impossible to wear. All she had left was her heeled boots.

Now, although I fully understand what she was going to go through, I was almost pleased by the situation.

Part II

So, there we were, a 5 hours hike in the wood from civilization, and all Karen had to put on was her tightest pair of jeans and wedge high heels boots. I was delighted at what the scenery for me would be like, but she wasn’t that impressed, knowing what she was going to go through.

“Well, you can always go with your shorts and for your feet, we can probably rip the sole of the boots off and keep them on your feet with a few pairs of socks.”

“With all those bushes? I would be scorched to the bone half way down, and I’m not thinking about my feet. And you know, the more I think about it, the more I think it could actually be fun.”

To my wide eyes expression, all she had to answer is:

“Come on, get your pliers.”

So we went through the usual routine of tugging, pulling, until the zipper was finally closed. I laced her boots, because she was unable to bend enough to do it. We gathered the tent and the rest of the stuff. It was a blast for me to watch her struggle with her extreme tight jeans and her heels. I was surprised by the fact that she was wobbling a lot less than I had imagined.

Finally, we were all packed and ready to go.

“You go first,” I said. 

She looked at me, and winked. 

“I knew you were going to say that!”

And down the hill we went. She was walking in small steps. Going downhill was the easy part for the jeans but the hard part for her heels, forcing her to walk sideways, but a mountain being a mountain, we had to go uphill a few times, and that’s where it became hard for her with the jeans although it seemed easier with the heels.

“I can barely lift my leg enough to climb, ” she said. “My hips are beginning to ache. And I’m not saying anything about my feet”

“There’s about 100ft more to go. We’ll take a break up there.”

On top of the hill, she sat down on a big rock, panting.

“You okay?”

“Yeah, she said. I can manage. It’s hard, but the feeling I get from the rubbing between the legs is awesome. I’m almost turned on. I feel I could just burst.” she said, while rubbing her hands on the stiff and tense fabric over her thighs and crotch. She stretched her legs and wiggled her feet.

“Now you got me turned on!”

“I’m sure of that,” she said laughing, “but it’s not the place to do it, and I’m afraid that, once out of the jeans, I won’t be able to put them back right away. I’m perspiring, and they’re kinda damp.”

“We’ll be at the creek in one hour, top. There we could relax a bit more. It’s all downhill from here to there anyway.”

“Yeah, great idea. A little refreshment is in order. Let’s go.”

She took the lead again. I was following, watching and appreciating all the moves her butt was making to walk in those tight jeans and high heels, and for a moment, I wondered if the seams would stand the ride.

We reached the creek about three hours after we left the camping site. There was a clear area on the other side of the waterway. There was no bridge, only a few logs that we had to use to hop on the other side. We went together, holding our hands. Her balancing was not easy with the heeled boots but the sole had a firm grip. Everything was going well until I slipped and ended up sitting in the water, wet up to my waist. Karen laughed so hard that she lost foot and went down in the water too. It was refreshing anyway. The usual I will splash you more than you did thing went on for a few minutes, after which we got out, soaking wet.

“Ooo, that cooling was needed, she said.”

“And now, your jeans are all wet.”

“So, yours too.”

“Yeah, but mine are not tight like yours.”

“Bah. I’ll live with it. As a matter of fact, that bath loosen them a little. Come on, in an hour we’ll be home, and I’ll be out of them.”

The rest of the trail was pretty flat, and mostly out of the trees’ shadow. The sun was bright and strong. And what do wet jeans expose to direct heat do? SHRINK!

When we finally got to the car, Karen was panting her lungs out, she could barely walk because her hips were aching more than ever, and the now tighter than ever jeans were compressing her legs even more, restricting the blood flow to the muscles, which was not helping her aching feet. She pulled down the zipper so she could sit in the car, and she took a long breath. Her stomach almost sprung out. Once home, I had to use scissors to remove the jeans. We could see all the seams imprinted on her legs and thighs. We both took a shower and a little rest. She wore loose sweatpants and flat shoes for the rest of the day. 

The next day, we both went back to work. The tight jeans adventure was not brought up. When I got home after work, Karen was already there, as usual, since she leaves her job one hour before I do. When I entered the house, I heard:

“Honey, is that you? Can you come to the bedroom? I need some help.”

I went to it, and to my surprise, she was waiting for me to close the jeans zipper again. I looked puzzled, but happy at the same time. Even more, she was wearing the wedge hiking boots.

“Well, the other pair was ruined, and I needed another one. But it seems I took the wrong size again. I have your pliers right here.”

The end. (for now?)

Author note: This story is purely fictional. If for some reason that happened to you or one you know… please, write to me with the details!! Also, I must point out that my primary language is French, so forgive the inevitable grammatical errors.. Anyway, I don’t think grammar is the main point here… unless it could be made out of denim, tight and wearable!

© Pete / monsterp63, April 1998

Re-written with more high heels, Feb 2012.

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