If the Shoe Fits… Ch. 01


This is a work of fiction. Names of people and products, characters, businesses, places, events and incidents are either the products of the author’s imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. All characters are over 18 when involved in sexual situations.

WARNING: This is a BDSM story that contains scenes depicting pain. This story could also have been posted in the Lesbian category so be forewarned that there are no men in this story.

NOTE TO READERS: I know that I have a lot of story lines already floating out there. But this story came to me and I had to capture it before it drifted away. Don’t despair. I’ll try to move them all along. As always comments and feedback are appreciated.

This story is dedicated to Nancy, Andy, Sue and Richard. Thank you for the inspiration. I hope your fantasies come true.



I love shoes.

They are my ever faithful companions. They are always at the ready in my closet. They make my clothes look good. They make my handbags look good. They make me look good. They never talk back. They never cheat on me.

Whenever I’m in the dumps it only takes a shoe shopping trip to lift my spirits. If you look in my closet you can quickly determine I’ve been down in the dumps many times over the past few years.

Thank God for shoes.

Chapter One

It was one absolutely shitty Friday in Manhattan. I finished up a marketing campaign for one of our firm’s largest clients and the lead from the client was absolutely hell on wheels pushing me to accommodate an expedited timeline so they could meet some arbitrary publication deadlines. I don’t like it when I’ve had more two cups of coffee in a day and that day I had four. My assistant was ready to murder me.

Here’s the topper. My soon to be ex’s lawyer was badgering my lawyer about finalizing a part of the property settlement. Even though we don’t have kids the property settlement was pretty complicated because of our respective retirement plans and the valuation of those plans. We’re both 42 and have already accumulated quite a bit of money in those plans. Anyway, there was a lot of bickering about the methods we used to value those plans and it put me on edge anytime I had to talk to my lawyer about it.

It was about 7 p.m. when I was finally able to extricate myself from my office and begin my unplanned weekend. I had one thing on my mind. No, it wasn’t sex. It was better. I was going to snag a pair of Stuart Weitzman’s that I’ve had my eye on. A pair of satin platform sandals with 5 inch heels. I’ve tried them on before and they made my legs and booty look just right. The only dilemma for me was the color. I took Lyft to Barneys and made the familiar weave through the store to the women’s shoe department.

There they were. On display. Like a beacon, calling me.

I flagged down a salesman and told him I wanted to see both the adobe and fuchsia in a size 6.

The department was humming and I located one of the few empty seats to await the arrival of my new babies. My pulse was pounding and this time for a good reason. I wanted these shoes. I needed these shoes.

It was only but a few minutes until the salesman arrived with a pile of boxes.

“Ma’am, I brought the fuschia in 5.5, 6 and 6.5 just to make sure you have a good fit. Try them on and let me know.”

Bless his soul. He was a cute guy, though too young for me. Honestly, if was appropriate, I would have pulled his pants down and given him a blowjob on the spot as a reward.

The salesman was kneeling in front of me. I tried the 5.5’s first. Too tight. No way those puppies were going on these feet. Then the 6.5’s. Too big. I waited with anticipation as he unwrapped the many layers of tissue paper to free the 6’s from their cardboard prison. He already knew my left foot was slightly bigger so he tried the left shoe first. Perfect. Just a bit snug but acceptable. Then the right shoe. Perfect again. Just right. He buckled the ankle straps and then it was time for the maiden voyage. I cruised around the carpeted floor like a queen. Blissful. I walked in front of the floor mounted mirror so I could admire my soon to be new shoes from three different angles. I was already thinking ahead to the outfits I had to match and what I wanted to buy.

I sat down and awaited his arrival with the adobe in a size 6. Now it was a matter of color choice. The obvious choice would be to buy both, but at $485 a pair that was not an option. It was already a ridiculous amount of money to pay for a pair of shoes, especially with my lawyer sucking up almost half of my take home pay.

To my surprise the salesman returned with a handful of boxes. “What’s up with all the boxes?”

“I have the Weitzman’s in adobe in a 6. But the lady over there (pointing to the next aisle) asked me to bring you these as well.”

I’ve had men buy me a drink at the bar, but shoes? I didn’t know otele gelen escort how to react. I looked over to the next aisle. A woman in the next aisle tipped her hand. She looked to be in her 30’s with stunning platinum blond hair up in a French twist wearing a 3/4 sleeve designer checked jacket and matching skirt. She had a proverbial mountain of shoe boxes in front of her.

Curiosity certainly got the best of me. I went over to her and sat in the seat next to her.

“Nancy Anderson,” I said, holding out my hand.

The woman turned to me, flashed a million dollar smile and said “Cassandra Moreau at your service” as she extended her hand to me and gave me a firm handshake.

“I understand you asked my salesman to bring me a stack of shoes.”

“Of course I did. I saw you making love to those Stuart Weitzman’s, which by the way look fabulous on you. You should buy the fuchsia. They looks most becoming on a brunette with blue eyes.”

I was overwhelmed by the presence of this woman. She clearly had command of this conversation. I felt like a paper boat floating down a stream.

“I asked your salesman to show you a few other shoes I thought that would look great on you. I wish I had legs as beautiful as yours.”

Well that wasn’t true. Her legs were amazing but I felt a soft glow as the heartfelt compliment touched me.

“Try them on. Pick a pair. It’s on me.” She flashed her AMEX Black Card at me.

I was quick to react. “No, I certainly couldn’t accept a gift from you. I don’t even know you.”

“But you will. And I would be insulted if you didn’t accept my gift. I’ve got more money than I know what to do with and it would give me the greatest pleasure to see a person so in love with shoes wearing a pair that truly flatters her.”

“Well, I can’t accept your gift. It’s really thoughtful.”

“At least try them on for me please.” She said it politely but there was a clear subtext of forcefulness behind this request.

“Sure, there’s no harm in trying them on.” I walked back to my seat. The salesman spotted me sitting down again and opened the first box. It was a pair of Jimmy Choo’s. Hitch caged suede in black with 4 inch heels. Stunning. I’ve never tried on a pair of shoes like these. Maybe because they were $995. If there was a shoe heaven then certainly the Gods had smiled upon me. I walked on a cushion of air to the floor mounted mirror. Paradise in three dimensions. I felt glamorous, pampered, entitled. Yes, I wanted these shoes. I was just thinking about who I would have to kill to possess them. I looked over to Cassandra. Her look of approval said volumes.

I returned to my seat. I reluctantly let the salesman take them off my feet. He returned them to their cardboard box and I watched with regret as he put the lid on them.

But there was more. I didn’t know there were various levels of heaven. I had heard about the levels of hell (that I was resigned to visit in my afterlife), but I didn’t know the same existed for heaven. He pulled the lid off a pair of Manolo Blahniks. Classic black leather pumps with 4 inch heels. I wanted to cry. The salesman effortlessly slipped them on my feet. I knew it would be bad form to finger myself to an orgasm with these shoes on so instead I walked around the shoe department making it a point to walk by Cassandra. As I Iooked into her eyes there was a clear connection made that momentarily distracted me. I stumbled on a wrinkle in the carpet and was caught by another shoe salesman before I suffered a highly embarrassing fall. I saw out of the corner of my eye Cassandra chuckling at my misstep.

I sheepishly returned to my seat while all eyes in the shoe department were on me. My embarrassment quickly melted when the shoe salesman unwrapped the final pair of shoes. A pair of Christian Louboutin black patent leather open toe platform pumps with 5 inch heels. And a bargain at $795. I had reached the promised land of the red soles. I was one of the chosen few. I thanked Jesus that I had a pedicure done earlier that week so my toenails had a perfect polish of Dior Pandore red. This time I took a tour around the shoe department with my eyes on the carpet so I didn’t trip again. Cassandra gave me a “thumbs up.” I couldn’t have agreed more. All I had to figure out was whether I was going to go without eating or without electricity and cable so I could pay for them.

As I sat down to ponder my shoe future Cassandra walked over and stood before me. She was wearing her own pair of new Christian Louboutin’s with five inch heels so she simply towered over me. I was bedazzled by her aura of self-confidence and outright glamour.

“You know and I know that those Louboutin’s were made for you.”

“I know,” I admitted.

“I’ve already paid for them,” she said, handing the receipt to me. “I knew they were the right ones for you before you even tried them on. I won’t take no for an answer.”

There was no way those shoes were coming mecidiyeköy escort off my feet, absent a loaded gun to my temple. “I can’t accept them,” I said with little conviction in my voice.

“Nonsense. My guess is that you’d break my arm if I tried to take them off you.”

I had completely softened by this point and at least tried to even the score. Besides, I was becoming besotted with her bewitching manner. “I’ll grant you that. How about you let me take you to dinner and we’ll order an expensive bottle of wine? My treat?”

She smiled. “Now that sounds like a fair exchange. I’ve got to run back to my place and take care of a few things. There’s a wonderful French bistro at 33rd and Third. I’ve got a standing reservation there. How about we say 9:30 p.m.? She took my hand in hers and covered it with her other hand. We looked at each other for about five seconds, then I pulled my hand away. I paid for the Weitzman’s (in fuschia) and left the store with precious cargo of over $1,000 of shoes that weighed all of about one pound.

I rushed to my apartment to tackle my next challenge. What to wear with my new shoes? And which pair? I only had an hour to get ready. And was this a date? I’ve never dated a woman. I’m sure it’s just a “get acquainted” dinner with my new best shoe friend. This was NOT sexual in nature. But then . . . . . why was I stressing over what to wear?

I did what I always do when I need to clear my head. I took a shower. After the hot spray hit my body it all became clear to me – – I really didn’t know what the fuck I was getting into. So I was going to hedge my bets. First I shaved carefully. My underarms and legs of course. Then around my pubes, not clean shaven but neat. Then a nice long hot shower. Refreshed, I tackled my wardrobe challenge. I picked out something sexy, but safe. My favorite navy blue dress, black lace bra and panties and my new Louboutin open toe pumps. My diamonds studs for sure. Pearls? Nope, too conservative. I’d go without a necklace. I jumped into a cab and got there ten minutes early.

She must have gotten there fifteen minutes early. She was sitting at the bar wearing a black sleeveless halter dress with yellow suede Louboutin pumps with 5 inch heels. Dressed to kill. Dripping with seduction. What was I saying about this dinner not being sexual in nature? I threw that assumption out the window.

“Nice shoes,” was her opening foray.

“I like yours too. Mine were professionally shopped,” I countered.

The dinner was uneventful. I played it safe with my two favorites – – French onion soup and the mussels and fries. Cassandra had the steak, rare of course, and the fries. When it came to picking the wine we both looked at each other to see who was the most wine knowledgeable. I deferred to Cassandra. She decided to split the difference with my getting mussels and her getting a steak. A Rochioli Pinot Noir, a world class Russian River Pinot and a not too shabby $175 on the list. It was delicious. We polished off the bottle halfway through the meal and decided not to be piggish by ordering another bottle. I told Cassandra about my divorce, how my husband cheated on me, and my college years at Vassar through my current position as a senior account manager with a major ad agency. Cassandra told me about her college years at Yale followed by an MBA at Wharton. She was never married and was pretty much exclusively dating women. Now I knew that I might be the dessert course. I have to say I was flattered by that thought, given that Cassandra was a knockout 30 something woman who could have her pick of the litter. I still wondered why she picked me and I also wondered if she was really my destiny or just a sidebar dalliance.

She of course invited me back to her apartment and I accepted. We took an Uber together to her place in the West Village. Her apartment was as stunning as she was. It was a large two bedroom apartment with a formal living room and dining room. It had a patio that ran the full length of the apartment with a view of the Hudson River and New Jersey beyond. It was a perfect moonlit night. As I was standing on the patio admiring the view I heard her yell from the kitchen, “Chardonnay?”

“Yes please.” I stepped back in the living room.

“Flowers, Sonoma Coast?”


Cassandra glided into the living room with two glasses of chardonnay. She handed me one.

As I was surveying her surroundings I not so subtly asked, “What do you do for a living?”

Cassandra, one I was to learn was always one step ahead of me replied, “Do you mean how did I get my money?”

“Well, that question did occur to me. You look so young.”

“I went to Wharton Business School. One of my classmates had an idea for a medical device and I jumped on the bandwagon early. I worked for eight years until the company went public and was able to sell half of my shares. I don’t have to work anymore.”

“So you now just pick up strange women in shoe departments?”

She türkmen escort gave a hearty laugh. “Of course not. I usually go to fine chocolate shops to pick up women.”

It was my turn to laugh. “Seriously, why me and why at Barneys?”

“Sometimes I’m impulsive. I was truthful when I told you that you looked extremely attractive in those Stuart Weitzman’s and it occurred to me that you would look even better in what I picked out for you. I really didn’t plan on picking you up, but all the better that it worked out that way.”

“I’m glad I met you. I’ve never known anyone like you. There’s something about you that I find alluring but I can’t put my finger on it. You’re so self-confident, so self-assured . . .”

“So in control . . .?” Cassandra added.

“Yes . . . that’s it.”

“You’re right about that. I like to be in control. Do you like to surrender control to others?” She was certainly forward.

I thought about that question for a moment. “Not really. At work I like to be in control. I get frustrated when I lose control. That’s why I was shoe shopping today. My client was trying to upend my carefully constructed calendar for their product rollout and my soon to be ex’s lawyer was trying to badger me about the property settlement when I wasn’t ready to discuss it.”

“Ahhh. But that’s precisely my point. Trying to stay in control is an exercise in futility. It’s not satisfying. It’s exasperating. Wouldn’t it be nice to surrender control so you don’t have to think. You can just feel?”

“Yes. That does sound appealing. I’m looked upon to make so many decisions. It would be nice to take away the pressure of making decisions and just focus on my feelings. I never get to do that.”

“And that’s what I see in you as well. Someone who can surrender control and can learn to feel again. Would you like to try with me?”

I took a long draw on my glass of chardonnay. “Yes, I would.”

“Let’s finish our wine and I’ll give you a short lesson. You can decide if you want to go further.”

We stepped out onto the patio to enjoy the view and the rest of our chardonnay. Both were perfect. Cassandra then took my hand and led me into her bedroom. It looked like it was out of a Restoration Hardware catalog. Muted grays and off whites. Very tasteful and very spacious.

“Wear this.”

She handed me a blindfold.

“It will help you focus on what you feel.”

“Now take off as much as your clothing as you feel comfortable. The more the better. But leave your shoes on. They look far too sexy on you for you to take them off.”

I decided to go all the way. I took off all of my clothes.

“Excellent. Nancy, you have a beautiful body. And I’m sure you don’t hear that enough.”

That was true. I felt so vulnerable standing naked in a strange bedroom with someone I just met today but I also felt comfortable knowing that Cassandra was so clearly experienced being in control.

“Your breasts are gorgeous. 34D?” she inquired.

“Close. 34DD. I should be a 34D but it’s those last pesky five pounds.”

“Don’t bother. You look perfect just as you are.”

I heard Cassandra step out of the room. I relaxed a bit, but her absence wasn’t long. When she returned she gently guided me until I was laying on my back on the bed with my legs hanging over the edge of the bed. She rubbed what felt like a Q-tip against one nipple and then the other. I smelled cinnamon. There was a warming sensation that started to get more intense.

“I smell cinnamon.”

“Very good my love. It’s cinnamon oil. Just a dab on the end of the Q-tip. So what do you feel?”

“I feel a warmth in my nipples; almost a glow.”

I could feel Cassandra’s hot breath on my chest. She then gently sucked one of my nipples in her mouth and rolled the other one between her fingers.

“Cassandra, this feels sensational. Please don’t stop.” The combination of the warmth and the stimulation was an irresistible combination. Without thinking my right hand went down to rub my moist pussy. Cassandra batted my hand to the side.

She pulled her head up. “Uh, uhhh,” she admonished me. “Who’s in control here?” She stopped playing with my nipple as well.

“You are.”

“That’s right. Did I tell you that you could touch yourself?”


“I should punish you for being a bad girl.”

I paused. So we were playing that game. “I am a naughty girl. What are you going to do about it?”

I felt the bed move as she sat next to me. She pulled me by the hair and guided my head until I was laying across her lap with my bottom facing sunny side up. I could tell that she had removed her clothes as I laid on her bare legs and could feel the smooth skin of her tummy. I was pretty sure what was going to happen next. I was wrong.

She pushed her hand between my legs and gathered the moisture from my sopping wet pussy and pulled it across my anus. My husband had never been into anal play so this was relatively uncharted waters for me. I clenched my cheeks together in response to the stimulation.

“Relax my love.”

I unclenched my cheeks. She slowly circled my anus with her slippery fingers.

“It feels like a low voltage electric current, but in a very good way. No one’s ever played with my ass before.”