Stiletto Style

by LadynStFreknBed©

I work in a large accounting firm, so can you blame me for trying to make things interesting? Everyone in my office is practically robotic in carrying out their daily tasks. Even the air seems dull.

My mom always said that I know how to make life interesting. I try to live up to that opinion whenever I get a chance. I firmly believe that life is what you make it. Of course, I didn't want to disturb my peaceful, almost non-existent relationships with my coworkers. Even though the people here do not interact any more than necessary, I don't want to provide fuel for the beginning of a rumor mill or create any animosity.

I only started working here three months ago. Already, I feel a little out of place. I dress in a less-than-conservative way. My stilettos make a little more noise on the parquet floor than I would like, but I wouldn't leave home without them. My suits have more flair than what you might expect from an accountant. And though I knew that my outfits have raised a few eyebrows, my boss was the first to suggest that I may be raising something else entirely.

"Stacy, could I see you in my office?" Mr. Blake said as he walked past my cubicle and towards the door bearing his name.

He held the door open for me and gestured for me to take a seat. There were two leather chairs across from his desk. I watched him stare at my legs as I took my seat and crossed them. He seemed fixated on my red stilettos for a few seconds. He cleared his throat and looked into my eyes.

"How do you like it here?" he asked.

"It's a little quiet for my tastes, but I don't have any complaints," I answered.

"Um, yes... well," he said and shifted uneasily in his chair. "Some of your coworkers have questioned your attire as the right image for this firm. And, well, I think a few of the men are a little uncomfortable about it."

I self-consciously ran my finger along the plunging neckline of my silk blouse. I pulled my fitted jacked closed.

"But.. I.. I think I look nice. Don't you?" I stammered.

"Oh, well yes, of course you look nice. I would be flattered to have a woman such as yourself on my arm any evening. But, this is a very conservative office."

"I understand," I said as I felt the tears well up. I hated that I was so extremely sensitive. I just imagined that my coworkers had been standing around talking about me behind my back.

"Oh, now don't get upset. Please. Your work has been exceptional. You just need to dress a little more conservatively around the office as much as it pains me to have to ask you to do so."

"It pains you?" I asked.

"Well, I guess it is safe to say that I find you very attractive. I would never say or do anything to make you feel uncomfortable working here. I just don't want you to feel as though you did something wrong."

"So, all I need to do is wear boring clothes and shoes," I stated.

"Oh, the shoes? The shoes are fine. No need to change the shoes," he said rather quickly.

"Okay," I said, trying to figure out why his response seemed so odd.

"You seem like a very intelligent, exceptional woman. Would you be offended if I asked you out?" Mr. Blake asked. "I don't usually date employees, but something tells me that you could handle working with me and keep personal things separate. What do you think?"

Keep personal things separate? I almost cried just thinking about coworkers talking about me. Of course, dating the boss could be a little smack in the face to anyone who talked badly about me to him. Anyway, it would be nice to go out. It has been awhile since I have been out on a date.

"That would be fine," I said with a somewhat mischievous smile.

The rest of the work day had passed without incident. Mr. Blake, or "Bradley" as he asked me to call him, had asked if he could take me for drinks and dinner after work. I welcomed the opportunity to relax and get to know him.

Just before the workday officially ended, Bradley left his office and approached my cubicle. Unfortunately, he caught me massaging my achy feet. I love stilettos, but there is a price you pay for wearing them. My achiness and bunions were constant reminders of what a woman will do for the sake of fashion. When I caught sight of him, he had stopped and was watching me rub my feet. I quickly slipped my shoes back on. He finished his journey to my desk.

"You ready to get out of here?" he leaned in and said.

"Sure," I said as I stood up and grabbed my purse.

Ah, another perk of dating the boss, a slightly shorter workday. I tried not to smirk at the others as we left the office. My boss opened his car door for me. I began to relax in the comfort of the leather seat.

Bradley seated himself and drove us to a small restaurant with which I was familiar. It was known that the city's elite patronized this establishment. Bradley opened the car door for me and I took his arm. We were immediately seated at what the maitre d' referred to as his "usual table."

After we were seated, I was tempted to slip my feet out of my shoes under the table, but I was afraid someone would notice. We ordered drinks and discussed a variety of topics. I felt surprisingly at ease in his company.

We ate dinner while continuing to make pleasant conversation. Then, our conversation took an unusual turn.

"So, how often do you wear stilettos? I think you have worn them to the office every day," he said.

"Um, yes, I pretty much wear a pair of stilettos every time I leave the house. Why?"

"Don't they hurt your feet?" he asked.

"Well, yes, but I love the way they look," I replied.

"So do I," he said with a smile.

I returned the smile. I took note that with this last piece of conversation and our talk in his office, he seemed to be encouraging me to continue wearing stilettos. I wasn't sure what to think about that. Why did he care so much about my shoes?

After dinner, we sipped on our drinks and talked for at least another hour. He seemed genuinely interested in getting to know me. I couldn't have been more thrilled. Now that I was getting to know him, he seemed like a sincere, kind gentleman.

He asked if he could take me out again on Friday night. I readily agreed. He took me home and walked me to my door. He gave me a peck on the cheek before returning to his car. I went inside my apartment with my hand covering the spot on my cheek where he kissed me. I sighed and leaned against the back of my door for a second.

"Thank God!," I thought as I removed my shoes. My feet cramped as they adjusted to being barefooted. I carried my stilettos to my closet and returned them to their place among my collection.

I went to my bathroom and began to prepare my bubble bath. When the water was how I wanted it, I undressed and lowered myself into the bubble-laden water. Gradually, my feet relaxed in the warmth of the bath water.

After my bath, I tried myself off and put on a robe. From my bathroom shelves, I grabbed my basket of foot care products and returned to my bedroom. I sat on my bed and began to rub my feet with a pumice stone. This helped to control the calluses that tended to build up. I wiped my feet with a towel and ran my fingers over the treated surfaces of my feet. When I felt they were smooth enough, I massaged a thick moisturizing lotion all over my feet. There was nothing I could do about the protruding bunions. They were beginning to affect the alignment of my toes. Only a doctor would be able to treat them now, I thought.

The last two days of the work week went smoothly. I wore a simple, tailored black suit and black stilettos to the office on Friday. I thought about wearing black lace stockings under my suit. Those stockings look incredible with these stilettos and would do wonders to thrust this boring suit into any sense of sensuality. But, I knew that my coworkers would have hissy fits.

Late Friday afternoon, my boss slipped me a note on his way out of the office. I quickly unfolded the note. It read:

"I dare you to meet me at your door wearing only your stilettos at 8 PM."

I blushed. I could never do that. There's no way. I laughed it off as some kind of joke. I left the office at the appropriate time and hurried home to prepare for my date. After showering and shaving, I selected a simple, short, black cocktail dress and black stilettos.

I anxiously waited for Bradley's arrival. At 8PM, the knock on my front door announced his arrival. I welcomed him into my apartment.

"Awe, I am disappointed in you," he said looking me.

"What? Why?" I asked.

"You were supposed to meet me at your front door in only your stilettos."

"I couldn't do that!"

"Why not? You're beautiful. Aren't you ready to show me more? Do you know how much appreciation I would show you in return?"

"I just don't feel comfortable yet," I said.

"What if I helped you feel comfortable?" he suggested.

I craved to be intimate with him. I was curious as to how he would make me comfortable. I also wondered about that appreciation he mentioned.

"How would you do that?" I asked.

"Close your eyes."

I looked at him questioningly. I wasn't sure I wanted this so soon. My body was yelling, "Do it!"

"Trust me. Close your eyes. Anytime you feel uncomfortable, tell me to stop and I will. Just make sure that you mean it."

I closed my eyes. I felt him walk behind me. He stood behind me and kissed my neck. It felt so good. It had been too long since I had been with a man. Bradley continued to kiss my neck as he unzipped my dress. He lowered the straps off my shoulders, allowing the dress to fall to the floor. He kissed me between my shoulder blades. He wrapped his arms around my waist while kissing my shoulders and neck. He pulled me close.

He slipped his fingers inside my panties. I held my breath. He slid my panties to the floor. He felt him rub the tops of my feet with my panties. Then, he gently caressed the arches of my feet just above the stilettos. It tickled.

He helped me step out of my panties. There I stood, naked except for my stilettos. He stood in front of me, teasing one nipple while sucking on the other. I moaned. I could feel myself start to get damp.

Bradley pulled me close and kissed me deeply. My breasts and erect nipples were pressed against him. As he kissed me, he ran his hand down between my breasts and across my stomach. He rubbed the small strip of hair and slipped a finger into my moist slit. I gasped as his fingertip massaged my clit. I began to whimper. I opened my eyes to see him smiling at me.

I was too caught up to worry about being naked in front of him. In fact, the look in his eyes made me feel beautiful. He kissed me as he continued to tease my clit. I broke the kiss several times when overcome with moans. I subconsciously clenched my thighs against his hand. My wetness increased as I felt myself tighten. With a series of whimpers, I succumbed to his finger with a pulsing orgasm. Bradley practically had to hold me up as my legs trembled.

I took his hand and led him to my bedroom. He asked me to lie down on my bed. He took my leg and kissed it from the top of my thigh to my stilettos. He spent several minutes kissing my legs and feet.

He undressed and lifted my legs to his shoulders. I attempted to take off my stilettos.

"Leave them," he said.

He kneeled with my butt against his thighs and my legs against his stomach and chest. He turned repeatedly to each foot, moaning as he licked along the insides of my feet. I could tell he was getting very excited. He parted my legs and slowly pushed his hard cock into me.

"Wrap your legs around my waist and try to scratch my back with your stilettos. Don't worry. You won't hurt me," he said.

I did as he said. He continued to pound my pussy. Whenever I scratched his back with my heels, he moaned loudly and thrust his cock into me harder. I was spurring him on with my scratches. I was enjoying my ability to turn him on in this way. My moans grew louder. The more he moaned and thrust under the power of my stilettos, the more turned on I got.

He kneeled again, and held my legs against his chest. He moved up so that he could continue to thrust into me while his thighs supported my butt. His thrusts were slow and seemed to be only to maintain his excitement. Then, he reached up and removed my stilettos.

I was embarrassed to have him so close to my disfigured feet. But, the bunions did not seem to bother him one bit. He started thrusting into me with surprising depth and fierceness as he licked and sucked at my feet and toes. I had never before had my toes sucked. He let one leg down and guided me to slightly bend my knee so that my toes were in his face as he leaned forward. He sucked on my toes as he pounded my pussy. He seemed like a man possessed. His tongue played with and massaged my toes in his mouth.

His cock was unrelenting. He was hitting me so deeply now that it almost hurt. My wetness tightly hugged his punishing cock. I whimpered as an orgasm shook my body. He sucked on my toes harder. I felt his teeth graze across my toes. He groaned and rapidly thrust into me until I felt him throbbing inside me.

This was the first time I had ever had a man pay so much attention to my feet while having sex. I was truly embarrassed about my bunions.

"I'm sorry that my feet are in such bad shape. It's the stilettos," I explained.

"Shhh..." he whispered into my ear as he put one finger over my mouth. "You are perfect in every way," he whispered while wrapping his arms around me.