Leaf Man Part 1 10 min read

It’s an early workday morning and the usual crowd of well dressed, young professional women wait in a posh, upscale London neighborhood.   Just another Wednesday.  The bus stops here to take these lovelies directly to the City of London for their high flying careers.  These are pretty girls from wealthy families who would never even think to acknowledge me in real life.  See,  I’ve been homeless for the last year and a half.  Dressed in rags.  Probably smell worse than I realize.  Just in a very bad way.

I wasn’t always in such a decrepit state.  I used to be a highly paid vice president at a huge multinational corporation.  A man of wealth & power that these women would fawn all over.  But two years ago ago I was made redundant along with my entire department.  Now I’m a nobody.

To make matters worse, when my cash flow stopped, my confidence left me,  my girlfriend left me and I started drinking heavily.  Fast forward to today and I am utterly ashamed of myself.  I feel so low.  But I guess there is one silver lining to my fall from grace.  I now have nothing to lose so I can finally indulge my long hidden desire to be trampled unknowingly by these uppity women.

I spent countless business meetings with women like them, noticing their beautiful court shoes and boots.  How I longed to be under their long, thin, stiletto heels !!    But I could never reveal my fantasy to any of them for fear of losing my job.  At this point, however, I no longer have a job to lose.  I can finally try to experience what it’s like to be stepped on by the Louboutins and Jimmy Choos that these young beauties love to strut around in.  Why shouldn’t I indulge my greatest fantasy if I can?

The bus stop is right by a four-foot-high brick wall. In the summertime, a few women can sit on the wall, but now it’s the late fall and cold outside (about 45 degrees F, 7 C). I like this area since the street is narrow, so the women have really no place to stand apart from each other, just a narrow strip of concrete next to the curb.

I arrived today at 5:00 AM before anyone arrived and crawled along the ground to my favorite spot, just in the grass area at the side of the bus waiting line. There’s an old drainage ditch, and it’s been covered over with leaves and debris from years of neglect. The park’s department probably will never come and clean up this mess.

This position is best for me, it’s out of their view, under a deep pile of thick leaves, compost, and loose grass. This spot is just perfect, it’s almost like being invisible. The leaf pile covers the ditch which is just two feet from the small concrete walk making the bus stop.

I wait buried under the deep pile, dressed in my black sweat pants and black sweatshirt hopeful with anticipation that some woman’s leggy walk will land her attractive spike-heeled shoes on me. This stranger’s shoe or boot would crush down firmly on my body, so I could enjoy her hard, unknowing presence on me.

At last, my prayers are answered, when who comes along but my old girlfriend Cortney Armstrong. Little does she know I wait for her here. I have gone out with her about two years ago, for several months until my business failure. She’s not really seen the real me since then. I have always wanted her to step on me with the sexy shoes that she often wore.  Always designer brands with thin heels.  Courtney was totally the fashion plate.

I’m ashamed to admit it but our breakup was all due to me.  She got really  angry at me during that time and it was all deserved.  I cheated on her repeatedly (to salve my fading ego) even when I swore to her that I wasn’t.  Turn about is fair play so maybe Cortney will treat me how I deserve to be treated – as the the dirt under her boots.

Let me describe my sweet, angelic-looking Cortney to you. Cortney is 5’ 5” (1.65m) and really slender. She’s a slim, stylish woman in every way. She has brown sharp peering shiny eyes with long brown hair that she often wears in a pony tail. Her body weight is near 115 pounds (52 kg). This morning she’s the first to arrive at the bus stop near to where I lay hidden under the compost pile.

Cortney’s an accountant at a bank, so she always must look very fastidious in her clothing. She is so stern in her facial expression as her super slender legs make her sharp metal-tipped boot heels click and clack on the cold sidewalk. The soles of her boots, at the same time, make a soft-sounding muffled thud, that hides the hard inner firm thrust of her thin legs. (She does step aerobics) I wish her thudding soles were now pouncing forward on my chest. Cortney finally stops walking and comes to a standstill, grating her heels on the hard cement, near the leaf pile which I’m laying deep below.

Cortney then stands in a very business-like manner. She’s not swinging her briefcase side to side as the other women often do. I love what she’s wearing her black, shinny slender, up to the calf, high heel boots today. Since Cortney is not so tall, she always wants to wear heels to make her look taller and more commanding. As I look at her boots from just below the ground level I notice that Cortney’s boots have dark brown discolored leather soles, which show off her brown leather boot bottoms, as I closely watch her standing, maybe two feet from me. I would love to lick her boot bottom’s clean. I wish only that she would be standing on top of my chest. I want to feel her total weight crushing down on me as she rests her feet on me through the thick thigh muscles of her strong shapely legs.

It would be also so good if Cortney might then rest one foot with her boot’s pointed toes against the side of my face, I would go into euphoria if that ever happened. My sweet Cortney has a habit of standing still with her full weight on just one of her boots’ high heels wobbly thin shafts.

Now I see her not so clearly, I dare only poke one eye through the tangled mess of the leaf pile.

Cortney has angled one foot up on her pointed heel. If she stood on my body with her boot’s heel poked on my chest, I would surely die under her hot-tempered, heavy stepping, pose. But that’s one of the risks I’m willing to take to get the most suffering I can get from this sexy and slim female. Cortney presently does not seem to notice the mound of leaves that I’m buried under.

I get excited just looking at her blackened and soiled leather boots grinding on the ground so very close, yet so far from me. I know that I’m stealing a look at her. But I’m now thinking that someday she could be grating her scented foot’s seductive heels down on my chest out of hatred of me for when we parted our ways, it was a very messy deal.

Oh, how I’m throbbing at the scent of Cortney’s Monday morning shower fresh perfume, as it wafts over the ground towards me. I now see her scrap one of her alluring boot’s metal heel tips through the pile of debris. Her raised pointed toe moves are aimed at my face as she wiggles her foot side to side, tipped up on her right boot’s mean-looking, thin high heels. Her metal-tipped boot heel makes mild marks in the concrete.

Cortney does this too I think, to relieve the boredom of standing in one spot for almost 5 minutes with no one to talk to before the bus arrives each day. She effortlessly pivots her full body weight on her one slender shinny heel.

She looks so attractive while poised on the sleek cosmopolitan styled black leather boots as the wobbly backs of her erotic high heels show off her sexy-looking leggy profile.

I hesitantly place my hand through the leaves near to where I think Cortney will angle the sole of her sleek foot down next. The sole of her size seven boot is just the right size to crush me under her rigid strong standing poise.

Just think, if Cortney’s heels were on me now, her slender black heel shafts would dig into me as her dainty legs made her pointy heels grind deep and sink down. After a few slow passing minutes, Cortney then shifts her foot and again places most of her weight on one of her soles quickly down.

Cortney’s foot lands with a soft thud in the leaf pile, but to have made that much noise her foot and thigh must be very solid. Cortney still has not stepped on my hand. I have judged wrong once more. Cortney places the sole of her foot this time close nearby the pile where my hand is. I watch to see how she angles her foot by pivoting her weight once more on her slender heel.

I crave that she was now standing on me. Cortney’s soft sun-tanned skin gets tense as she stands firmly again on only her one nearby and visible, thin alluring black heel. I am so close to her legs that now, I can now smell her tempting body’s fruity perfume, mixed in with the strong leather scent of her boots.

I feel the slight warmth radiating from her body heat, under her winter coat, as it streams towards me through the crisp morning air. I get excited with anticipation.

I press my rod, which is now a stiff member, solidly against the ground, in order to help me imagine, my dear sweet Cortney is now standing solidly on top of my dick. I still long for that she would sink one of her slender black shinny heels deep into my stomach.

To think that such a luscious woman is so close to me, yet in reality so far. Such a simple thing as her black leather boot can get me so very excited. Cortney’s beautiful body and with her hidden manicured toes inside her strong-looking black boots, which she herself, probably does not spend much time thinking of.

Yet to me, if I am lucky enough, she will step on with her foot me for maybe a moment, or perhaps even for a few seconds. What joy it would be if just for a few moments she would place her pointy toe on my hand.

I watch her seductive boots embrace the cold ground and wish that my hand was under her body’s powerful weight focused through her feet. I then move my hand hesitantly forward, once more, though to the soft earth area near to where one of Cortney’s hard boot’s sole is anchored. I then slide myself along the ground, pressing my stomach flatter, to be closer to her shinny rock-hard sculptured stance.