I went to college in a mid-sized city, home of what was then a major technology firm surrounded by two post-secondary institutions. As a result, the area was a busy mix of students along with relatively wealthy individuals and families. While I had my fair share of women during my college years, there was always something lacking; the experience for me could never live up to my expectations. It was good, but never great. I had a very particular fetish - high heels. Not just any pair of high heels, I was mesmerized with Louboutins, Prada, Gucci, Chanel, etc. My fetish may have been somewhat on the extreme end as I found myself less interested in porn and instead, would rather browse the online boutiques. I am not sure how this fetish developed but it does tend to consume me. Needless to say, the women studying at my college were more or less in the same position as me – that is, in no position to drop over a thousand dollars on a pair of shoes.
To alleviate some of my financial difficulties of being a college student, I responded to an ad for a mathematics tutor in a popular local online forum. I figured this would be a simple and flexible enough job to make some money on the side as I would only be helping with elementary school level mathematics. I sent off my resume and began browsing other job postings.
By the next day, I had received an email in response for the tutoring position, inviting me to coffee so we could meet and discuss before anything was finalized. Even though I was more than qualified, I had been a tutor for a first-year mathematics course at my college, I was still a bit nervous and treated it like I would have for any professional job interview. I arrived at the coffee shop ten minutes early and took a seat at one of the more isolated tables despite the store being empty at the time. A few minutes later, I heard the door to the store open and in walked an absolutely stunning beauty. She was in her early thirties but could easily pass as someone in their mid-twenties. My eyes went head to toe of her five-foot six frame, eyeing her long wavy black hair, tight-fitting blue dress with a giant bow on the front, black silk pantyhose, and a pair of Louboutin Pigalles.
“You must be Mark. I’m Michelle, nice to meet you.”
I stood up to shake her hand and was a little taken aback as she was obviously well-off. I offered to buy her a coffee but she declined and went to order herself at the counter. She was the type of woman who obviously put a lot of effort into her presentation everyday. Perfectly manicured nails, form fitting dresses that hugged her petite Chinese frame, and salon styled hair. For me however, it was the heels that enthralled me. As we sat down to talk, I would always catch my eyes glancing at her cleavage, nestled between what I would later confirm to be C-cup breasts, and her heels. Despite having done interviews for internship positions at some well-known financial institutions over the summers, this informal meeting for a simple tutoring job would have to be the most difficult meeting I had in terms of keeping focus. Luckily for me however, she was extremely outgoing and easy to talk to despite my initial prejudices. She proposed that I could help her son weekly with his homework and we exchanged numbers so that I could contact her in the event I needed to reschedule. The position was simple enough, it was more of a baby-sitting type role so Michelle could spend her time on other errands, and she detested math (even elementary mathematics oddly). I made my way home beyond overjoyed as not only had I gotten the tutoring gig, but I had some mental masturbation material with Michelle.
Every week, I would make my way over to her house and get paid while getting an opportunity to eye fuck Michelle. She never dressed slutty, but always had on tops that accentuated her breasts and shorts or skirts that let her long smooth legs flow freely. The tutoring was simple enough for me that I could also work on some of my own projects simultaneously while stealing a glance at Michelle whenever she was in view from the living room. Being able to see her shoe rack at the foyer was also always a treat as I entered and exited her house.
It had been a couple weeks now and once again, I was in her living room tutoring when Michelle walked in to check on the progress. She wore a lacy black halter top paired with short ruffled skirt and covered herself in a shawl as the air conditioning was blasting.
“Mark, do you mind helping me put a box away in my walk-in closet?”
“Of course.” I think I would have done anything she requested.
She grabbed a box behind the armchair next to the sofa I was sitting on and handed it to me.
“Thanks so much,” she giggled, “I can’t reach the top shelf.”
“Wow, Louboutins!” I exclaimed out loud without thinking.
Michelle let out a chuckle. “You know what Louboutins are?” she asked inquisitively with a sly smile on her face.
I tried to play it cool and not sound like a pervert by saying, “Who doesn’t?”
In an effort to diffuse the awkward situation, I stood up to make my way upstairs despite having never been to the second floor of her house. Michelle immediately jumped up as well.
“Let me show you where the closet is.”
She led me up the steps into the guest bedroom where she informed me she had been using the closet to keep all her shoes. As she opened the door, it was like peering into my version of paradise. She must have had tens of thousands worth of designer heels.
“This is the shelf where I keep my Loubs,” she exclaimed with glee.
I could not bring myself to say anything as I was still processing what I was seeing. The heels I had spent hours online looking at, all right in front of me. It wasn’t until I saw the stunned expression on Michelle’s face and her hands covering her mouth when I realized I had a massive erection. The mirror against the wall verified my suspicions that it was very visible, and she had definitely noticed.
I had never been in such a situation and all I could blurt out was, “I’m … so sorry, … I have a thing for heels.”
Michelle let out another small chuckle followed by an, “oh my.” My erection was so strong it actually began to hurt a bit, so I just looked up and closed my eyes for a bit to compose myself. I stumbled back a bit onto the guest bed when I felt her hand had made its way down my sweatpants and began lightly caressing my cock. I was still at a loss for words and could not believe what was happening. Despite having fantasies about Michelle for several weeks now, I would have never acted upon anything, I knew she was married. My chest felt cold while the thumping of my heart reverberated through my body.
When I had stabilized myself sitting on the edge of the bed, she pulled my sweatpants and boxers off with one swift pull revealing my aching cock pointed straight in the air. She took hold of my cock with her left hand and began ever gently giving me a handjob. Steady and fully in control while I was still shell shocked. It felt surreal seeing Michelle, this trophy wife, sitting upright on the carpeted floor right in front of my tugging on my penis ever so lightly.
“So, what about heels?” She asked in a sly inquisitive tone.
With her right hand, she took the box I had been carrying and opened it taking out a pair Lady Peep Louboutins. These were a six inch heels with small platform and peep toe in patent black leather, of course, accented by the red sole. She hovered it over me almost as if teasing me on one hand, and forcing to admit my perverted thoughts on the other. While Michelle might be accused of depraved thoughts herself, I later learned not only did her husband suffer from erectile dysfunction, he also traveled a lot for work leaving her unsatisfied, unfulfilled, and frustrated.
I only managed to let out a deep groan as she positioned herself directly in front of me and began sucking on the tip of my cock before slowly and ever so sensuously taking my entire cock in her mouth. I watched her expertly glide my cock in and out of her mouth while her tongue caressed every inch of it.
“Could you put those heels on Michelle.” I finally managed to utter out a proper sentence after I had regained some composure.
She looked up at me still with my cock in her mouth, now with a wide grin. She got up and sat next to me on the bed and began putting the peep toe heels on in what I could only describe as an intentionally seductive manner. It was as if she discovered the kryptonite that could be used to control me, and to be truthful, she did. She stood up and lifted one leg into the air so her toes were right under my chin, then she began circling them around my chest. My heart was pounding and my cock was straining as I would have never imagined such a scenario ever playing out. Michelle got back down onto her knees and began sucking on my cock that had already been lathered in her saliva. She varied the rhythm and within moments, I could not hold it in any longer. I extended my left hand behind her silky wavy black hair at the base of her neck to hold her head securely in place against my cock as I ejaculated deep into her throat.
That was probably the most satisfying blowjob I had ever received in my life. I was still gathering my thoughts, trying to piece the events together from a dream like state when I heard the thump of a car door closing and I instinctively put my sweatpants back on and made my way back downstairs. Head in a daze, I packed my things and made my way out as fast as I could manage while trying to be calm when making my goodbyes.
Over the course of the week, I could not stop thinking about what had happened. Michelle and I had exchanged text as well, but nothing sexual and she seemed incredibly casual about everything. Thoughts circled my head and I was unable to focus in any of my classes. Was it just a one-time thing? Why did I not take things further and at least taken off her clothes so I could see her breasts and vagina? Was Michelle interested in more? I did begin to recall some interactions between us that I probably mistook for just friendly gestures, but were really flirtier in nature such as a hand on the thigh here and there.
Perhaps my expectations were a little skewed from porn and my expectations of her sending sexually suggestive texts constantly were unrealistic. The thought of her modeling her heels for me filled my thoughts and I no longer put any emphasis on the fact that she was married. I decided that the following week, I would head over to tutor just as I was expected to do but I would let her make the first move. If she was only interested in a one-time fling, then so be it, but if she was interested in more, I would happily oblige.
Friday had come around once again, and I got off at the bus stop and made my way over to Michelle’s house to ring the door bell. As the door opened, I was a little surprised to see her husband had answered, but nevertheless made my way in with a slight dejection realizing anytime alone with Michelle would not be possible. As I sat in the living room, I heard the distinctive click of high heels against the hardwood floor. She was clearly teasing me. I tried to shake it off and convince myself that it was a one-time romp and that would not happen again, despite the fact that my heart ached for more. She then sat at a table, visible to me, in another room, heels slightly off the ground, clearly mocking me. She had discovered my fetish, and now this outrageous display that she knew gave me an uncontrollable erection.
I made my way to the washroom hoping to masturbate, but Michelle stepped in front of my path knowing my plan.
“You gotta be kidding me.” I exclaimed.
She gave a mischievous smile and bit her lip, “You’ll thank me later, just go back.”
It was about time for me to head home when I noticed it was raining outside. I went into the kitchen to let Michelle and her husband know that I was leaving.
“Oh, let me drive you home Mark.” Michelle exclaimed.
I tried to decline politely, “There’s really no need. It’s just an intermittent light shower.”
“Don’t be silly, you live almost an hour away,” she shot back, despite both of us knowing that I was less than a ten-minute car ride away.
I got into the passenger seat of her BMW and as she entered, she threw her sandals into my lap as she had already changed into flats to drive.
“You’re absolutely crazy,” I let out a chortle of a laugh as I moved my hands over the pink leather of her YSL Tributes. This was one pair I was absolutely crazy for, and here I was holding them, smelling them. The straps, the shape, it exuded sexiness.
She pulled out of her driveway and within minutes we had reached the parking lot of the low-rise condo I had been renting at for the term.
“Ok, carry me in,” she instructed me as she turned off the ignition.
“Lady, what?”
Her personality was always an enigma to me. She had an incredibly bubbly and inviting personality yet one was always a little on edge when talking to her.
“Well, you don’t expect me to get those dirty before going on your bed, do you?” I could not tell if that was said sarcastically or not, but regardless, I knew my reward was just around the corner. I let out an exasperated laugh, got out and made my way over to the driver side. I scooped her up into my arms, admiring her full chest in a simple white spaghetti strap top while the pink skirt she was wearing matched the heels I clutched onto. Michelle let out a laugh as I informed her that the elevator was broken and I had to carry her up three flights of steps. The realities of student living.
As I entered the unit, I was hoping my roommate would be out in the common living area to make him jealous of seeing a stunning woman in my arms, but alas, he was in his room. Upon entering my room, I lay Michelle onto my bed and immediately began work on getting her into the sandals I was holding onto. It seemed she always knew just what would get me going; these were over five inches high and accentuated her figure perfectly.
“You’re so sexy,” I exclaimed as I kissed and caressed her feet while working on putting the heels on her other foot.
I would not let the opportunity escape me this time as I pulled off her top and undid her lacy white bra revealing those perfect breasts with delightfully soft pink nipples. Next, I began to remove her skirt and pink thong simultaneously revealing her waxed pussy (I believe it’s called Brazilian wax, although I’ll admit I’m not familiar with the terminology). I immediately turned back and began sucking on her breasts while massaging around her clit before kissing her body all over head to toe.
“What was that you were doing walking around like that? Trying to tease me?” I inquired, “You need to be punished. You’re a bad whore aren’t you Michelle!”
I turned her over and gave her several firm spanks against her bare bottom. Perhaps it was the raging hormones of my youth, or my animalistic nature fully possessing my body, the intense desire to take Michelle overwhelmed me. With both my hands pressed against her ass, I spread her cheeks slightly to expose the insides of her moist pink vagina. I could not wait any longer and thrust my throbbing cock deep in her pussy, repeatedly thrusting in and out as I lay on top of her back, grabbing and massaging her breasts with my hands while kissing her neck.
It was not long until I flipped Michelle over so I could fuck her in my favorite position. I hooked my arms under her legs and pushed forwards towards her head so that her heels were now dangling right above her head. Once securely in place, I looked deeply in her large brown eyes as I began penetrating deep in her pussy again. Her squirms and my grunts would have certainly alerted my roommate providing another source of stimulus for me knowing my performance would be heard.
As I was fucking Michelle, my mind was consumed with all the fantasies I had with Michelle when she was just masturbation material. I had so many outfits, places and scenarios in which I wanted to ravage her. But the most pressing concern at the moment, where would I cum on Michelle in commemoration of the first-time fucking this trophy wife? Perhaps it was a desire to play out the fantasies I saw in porn, or my sudden deep urge to mark her as my property, I decided upon giving her a facial. When I felt my balls convulse and ready to shoot a hot stream of cum, I pulled out and sat on top of Michelle’s chest, pointing my rock-hard cock directly at her face and unloaded.
I collapsed back onto the bed next to her. I could say I have never felt so satisfied before. Sex is like pizza, it is always good, but the best is a surreal intoxication of emotions, lust and desire that leaves you longing for the next encounter.
We lay for there for a few moments, catching our breath and processing what had just happened.
“Carry me back to my car,” Michelle turned to me and said seductively.
Despite what I had just done, feeling like the most, for a lack of a better term, alpha male, she still managed to flip the situation and turned back into a lady with princess syndrome. Perhaps it was the mutual understanding we had of our situation, that I was able to dominate her sexually as she was cheating with me, but she could control and pull me along knowing that she was my fantasy.
“You’ll have to leave your heels here, come back again if you want to get them,” I said in as much of a masculine tone I could muster. I could guarantee another visit from Michelle, and while waiting, it was a trophy for me, the scent and sight of a conquest.
I would later come to the realization one of the best gifts Michelle gave me was confidence. Being with her gave me the courage to be more demanding of my wants sexually and to be more confident around women in general. Expressing what I wanted her to do, what I wanted her to wear and dirty talk just came out naturally around her.
After Michelle had gotten dressed and collected herself, I picked her up and made my way down the flights of stairs back to her car where I saw her off. Our afternoon frolic would play in my head for the rest of the day followed by a sleepless night of fantasizing about what I would do to her on our next escapade. I finally decided upon buying a leash and collar before dozing off.
