Walk a Crooked Milf Ch. 01

Chapter One - I Don't Go To Church, Kneeling Bags My Nylons

For as long as I can remember, I've always loved watching Mrs Cashmore walk to church. To be fair, I've always loved watching Mrs Cashmore do almost anything. But Sundays were special because she dressed for church.

A tight figure-hugging suit with a skirt that was not immodest but it was moulded to her buttocks and thighs and a hem that flirted with being too short for church but wasn't quite, the kick-pleat in the back opened and closed as she walked. The jacket, cinched at the waist by a single button, the buttons on her blouse which was always white, sometimes silk -- sometimes satin, strained to contain her ample bosom.

Her flaming red hair, straight, shoulder length with a fringe, her makeup was heavy and exotic, as was her perfume. And her legs. Those glorious legs: long, toned, unblemished, and sheathed in the sheerest of sheer shiny nylon. Her hosiery glistened in the sun. Her feet were shod in four-inch pumps, always black.

She was not pretty in the true sense of the word but her face was interesting and when she smiled she looked beguiling. Delores Cashmore had a thing for red lipstick; she always wore it.

I'm guessing that she was in her mid-forties, she looked every day of her age but she looked alluring and she was stylish; always well dressed, only occasionally in jeans, but usually in a skirt or a dress and she always wore nylons and heels. She even wore hotpants with pantyhose with a designer t-shirt when she worked in the garden. I didn't know what she did for a living, she came and went at strange hours and at eighteen years old I wasn't about to ask.

She was what was commonly referred to as a MILF: Mother I'd Like to Fuck.

"I don't know how that woman can hold up her head in church; I'm surprised she's not struck by lightning at the doorway," my mother often said.

My mother never explained why; she just told me to stay away from Mrs Cashmore which was a funny thing to say because it's not as if I had anything to with her. I just worshipped her from afar.

On Sunday mornings I'd wait for her to leave for church and follow her at a discreet distance, staring at her bottom and legs, getting horny like only a teenage boy can and then I'd race home and masturbate thinking about her.

When I masturbated I would slip my cock into the leg of a stocking I had stolen from her clothesline and caress a pair of her knickers, similarly snowdropped. I replenished the nylons and knickers as necessary once they became too tattered and torn, about once every three months. I was confident that she didn't suspect that it was me snowdropping her laundry, at least she gave no indication on the rare occasions that I spoke to her.

I studied her from afar. I watched her working her small garden, collecting her mail, hanging out her washing, leaving and returning from shopping trips. Opening the door to gentlemen in the evening and farewelling them late at night; from my bedroom window I saw it all. Then late one afternoon she came home and rummaged in her purse. I saw a look of consternation cross her face. She had forgotten her keys; she had most likely left them inside and locked herself out. She scanned the street and saw that no one was looking and lifted a concrete gnome that adorned her front garden and took a key out from underneath it and used it to open her front door.

A few minutes later she returned the key to its hiding place.

I had a way into her house if I wanted to. The question was; would I be so bold?

****

The following Sunday I watched Mrs Cashmore leave her house and walk to church and I followed her partway. When I was sure that she wasn't returning I ran back to her house and checking that the coast was clear I took the key from under the gnome and let myself inside.

Almost immediately the scent of her perfume invaded my nostrils. It was something exotic; I had smelled it on her on the few occasions that we had spoken. The scent alone was enough to make me hard.

I knew that she had no pets or visitors because I had been spying her for so long that I thought I knew more about her than anyone else in the street. How naïve I was... how wrong... how stupid!

The house was neat. The ground floor consisted of a kitchen, a reception room and a small dining room. It mirrored the other houses on my street, all built by the same builders as part of an urban development. The rooms were expensively furnished; whatever Mrs Cashmore did for a living she was well paid for it or had more likely been the beneficiary of an endowment from a divorce or a deceased estate.

I cautiously made my way upstairs, my palms sweating. The scent of her perfume grew stronger as I approached her bedroom. There was a second bedroom and bathroom on the top floor. The silence was eerie.

The main bedroom was furnished with a queen bed with matching side tables; a large vanity table with a chest of drawers built into it, an antique freestanding polished walnut full-length mirror and unlike my mother's bedroom, Mrs Cashmore had installed built-in wardrobes which ran the whole length of one wall.

I made my way over to the vanity. The surface was crowded with cosmetics, lotions, perfumes, a glass containing an assortment of makeup brushes, a box of tissues and a sachet of facial wipes. All similar to what my mother had on her vanity but in greater quantities, greater variety, and so much more expensive. I was no expert on makeup but I recognised the brands as being upmarket. There was also a hairbrush and a manicure set. A few strands of her flaming red hair were embedded in the bristles of the hairbrush and I bought the brush to my nose and sniffed them. I couldn't help myself and I pulled a few hairs from the brush and put them in my pocket. A little bit of her to keep for myself.

I opened the first drawer of the chest of drawers and I gasped. It was full of knickers and matching brassieres; all silk, satin or rayon. All the colours of the rainbow but also some black and some white ones. Some were hipster briefs, some were boy-leg, some were full-cut and there were even a couple of pairs of directoire knickers and cami-knickers.

I opened the second drawer and found an incredible amount hosiery. There were fully-fashioned stockings, hold-up stockings, and lots of pantyhose. They too came in many colours but the majority were black or flesh-toned, some were loose or balled together, most were still in their packages. Beside them were garter belts, suspenders and half a dozen wasp-waisted basques and corsets with garters attached. I ran my fingers across the silky hosiery and my cock engorged to full tumescence.

The bottom drawer contained full-slips, half-slips, petticoats, camisoles and chemises mainly in pastel colours and all constructed of shimmery satiny and diaphanous sheer fabrics. I lifted a satin slip to my face and rubbed it my cheek. It felt cool and delicate and a scintilla of Mrs Cashmore's scent remained on it. I carefully returned it to the drawer and then I did the same with a few pairs of knickers, where as well as rubbing them on my face, I sniffed the crotch and imagined I could smell her sex on them although I was sure I was imagining it.

I closed the drawers and opened the wardrobe. Inside it hung an array of expensive and stylish skirts, dresses, blouses and suits. Folded neatly on the shelves were some tight-jeans and hotpants, t-shirts and tops. There were some lycra tights and crop-tops that she wore when she exercised or went jogging. The multitude of high heels arranged on the shoe-racks was astounding; every colour and style one could think of. There were only two pairs of flats and two pairs of running shoes.

I checked the other rooms quickly but there wasn't much to see other than that in the bathroom, where her medicine cabinet contained oral contraceptives which made me surmise that she was sexually active. Then I spied a veritable treasure trove! Mrs Cashmore's washing basket was filled to the brim. I knew that she hung out her washing on Wednesday and Sunday afternoons so it must have held a half a week's worth of dirty laundry.

I impatiently emptied the basket on the tiled floor and was astounded by the amount of hosiery and lingerie that lay tangled amongst the other clothing. She must be changing her knickers, bras, stockings and pantyhose three times a day!

By now my cock was throbbing in my jeans and I sorely needed release. It would be so simple to select a stocking and drape it over my cock and put a pair of her knickers to my nose and just whack off. But this was an opportunity not to be missed and I wasn't sure I would ever get up the courage to break into her house again.

I checked my watch and figured that with a safe margin for error I had half an hour at least before Mrs Cashmore returned home.

I couldn't help myself. I quickly stripped naked and rummaged through the pile of laundry and selected several items and lay them out on the bathroom vanity. I had this unique opportunity and I wanted to feel Delores Cashmore's intimate apparel against my skin. I had often fantasised about making love to her while she wore her intimates and now I could at least feel and smell the delicate garments that I imagined she would wear when I fucked her.

I had sat fascinated watching my mother dress when I was young boy. There was nothing sexual involved, I was too young and mother always made sure that I never saw her naked but the ritual of putting on her foundation garments was to me sensual and exotic. I figured I wouldn't have too many problems trying them on for myself.

I picked out a red and black satin and lace garter belt. I was slim but not skinny and I was able to shimmy into it without too much difficulty. The feel of the silky fabric on my waist and the garters tickling my thighs was unbelievably prurient and naughty knowing that they had been worn by my favourite woman in the whole world. I carefully rolled up a stocking, just as I had watched my mother do a thousand times and stepped into it and slowly pulled the delicate garment up my leg.

The stocking was black and fully fashioned and it felt incredibly sensual on my skin. I clipped the garters to the welt and straightened the seam as best I could. I was not very hirsute, in fact I had hardly any body hair at all, just a few whisps and you couldn't see them through the nylon. My leg looked very sexy in the stocking, even if I did say so myself and I slipped the matching nylon on my other leg and admired the result in the mirror.

My cock was hard and aching and dribbling pre-seminal fluid; I was too scared to touch it and I almost came when I slipped on a pair of Mrs Cashmore's red nylon hipster panties and pulled them tight. The feeling was astoundingly carnal. I snatched another pair of full-cut knickers and a nylon stocking out of the pile and raced to Mrs Cashmore's bedroom and stood before the full-length mirror.

I pulled the front of the knickers I was wearing down a little to free my penis and slipped it inside the nylon stocking and bought the crotch of the full-cut knickers to my nose and inhaled whilst looking at myself in the mirror and relishing the lecherous satiny sensual feel of the lingerie and stockings against my sensitive skin.

I took myself in hand and orgasmed almost immediately. My climax was so earth-shattering that I fell to my knees.

Ropes of steaming semen blasted through the delicate stocking and spattered on the polished wooden floor as waves of intense pleasure emanated from my throbbing phallus and coursed through my body. I inhaled the musty lewd stink of Delores Cashmore's cunt deposited in the gusset of her knickers and imagined it was her tight steamy vagina gripping my cock in place of my fingers.

I don't know how long I languished in the surreal salaciousness before I descended from my orgasmic pinnacle but when I did I realised that I had taken more time that I should have to enjoy the delights of Mrs Cashmore's laundry basket.

I took the knickers from my face and wiped up my slimy issue from the floor and dabbed at the pool of semen stuck to the stocking covering my cock. I raced back to the bathroom and shucked out of the knickers, stockings and garter belt. I put the semen-soaked knickers and stocking in the bottom of the laundry basket followed by the garters, stocking and panties that I had worn, then I stuffed the remainder of the clothes I had dumped on the floor back in the basket, but not before I pilfered a pair black satin knickers as a trophy.

I quickly dressed and checked my watch. I was cutting it fine. I took a quick look around and everything seemed like it was where it had been when I'd entered the house. I left through the front door, locked it behind me and put the key back under the gnome.

I bolted home and raced up to my bedroom, locked the door behind me and stationed myself at the window where I could see down the street, waiting for Mrs Cashmore to come home.

As it turned out, I needn't have rushed. She didn't return home for another hour; after church she had taken tea at a tea house on the high street.

*****

The following Sunday as usual I followed Mrs Cashmore to church. I was not about to press my luck and enter her house again, I would enjoy the sight of her walking down the street and then race home and masturbate sniffing the black satin knickers I had stolen for her laundry basket. She was about halfway to church when she suddenly turned around and started walking back towards me. I guessed she had forgotten something and was returning home to get it. Whatever the reason I knew I needed to keep my wits about me so I just kept ambling along; a teenager out and about, probably heading to the high street shops to pick up the Sunday papers for his mother. That was the cover story I had concocted in case of just such an eventuality.

I had my hands in my pockets; my shoulders hunched over and I was dragging my feet with my head down. I did not want to make eye contact with her and I was trying to manoeuvre the erection in my jeans so that it was not so obvious.

"Young man why are you following me?" Mrs Cashmore had come to a complete stop in front of me, blocking my way.

I had to stop too and I mumbled my reply.

"I'm not following you. I'm going to the newsagent to get the papers," I replied still looking down at my shoes.

"Look at me when I'm talking to you boy. Show some respect," she admonished me.

I looked up at her and was immediately taken with her beauty. Her eyes were green and her flaming red hair framed her face which was heavily made up and my eyes were drawn to her red lipsticked lips. I breathed in her perfume and my cock which had been deflating began to harden again at the memory of sniffing her intimates in her house.

"It's quite coincidental that you leave home at exactly the same time that I do and walk to a newsagent that is further away from one the one closest to your house," she said in a matronly voice that was dusky and exotic.

"We have an account there," I answered and my face blushed at the lie.

Delores Cashmore glared at me as if she knew I was lying.

"So if I asked your mother the same question she would give me the same answer?" a wry smile crossed her face.

"Yes Mrs Cashmore," my face became redder.

"Well I'm not convinced that you are telling the truth but I have to get going to be on time for the service. I'd like you to come around this afternoon so we can discuss this further," she said.

My heart flew into my mouth. The possibility of being in Mrs Cashmore's house again was incredibly exciting. I was so stunned that I didn't know what to say.

"Be there at two PM sharp; I have no time for malingerers," she quipped.

Then she looked down directly at my crotch where my erection was bulging the front of my jeans.

"Teenagers today," she huffed, turned on her heels and walked away back in the direction of the church.

*****

"Have you ever seen the 1951 film Ace In The Hole starring Jan Sterling?" Mrs Cashmore asked.

I was sitting on the couch across from her in her lounge room.

I had spent the time between when she confronted me on the street that morning and two PM that afternoon wondering what she wanted. She was cordial when she met me at the door, still wearing her church clothes: charcoal grey suit with a skirt that rested three inches above her knees, white satin blouse, black heels, and shimmering tan hosiery. Her makeup and hair were perfect as usual and her perfume drifted across the room to my nose.

I guessed I had followed her once too often and she wanted an explanation. I thought my newspaper anecdote would still hold water. She left for church the same time that I went for the newspapers; it was all a coincidence. My story would ring true as long as she didn't ask my mother. Mrs Cashmore had been correct in assuming that we actually got our Sunday newspapers from a newsagent around the corner from our house, not on the high street near her church.

Her question about the old movie threw me. It also didn't help that she had crossed her legs and her skirt had drifted up her thigh another few inches.

"No Mrs Cashmore I have never seen that movie," I replied a little petulantly.

"Jan Sterling made a classic line in the movie oft quoted back then. She said 'I don't go to church. Kneeling bags my nylons.' Any idea what that might mean?" she asked, sipping the tea she had made for us both.

"I've no idea Mrs Cashmore and I still don't understand why you wanted me to come to your house," I replied indignantly, even though I was both thrilled and terrified to be in her house and in her presence.

"Bear with me William," Mrs Cashmore said, calling me by my Christian name for the first time.

"Do you know what Jan Sterling meant by bagging her nylons?" she sipped her tea and looked at me over the rim of her cup like a school teacher looking at an errant pupil.

I shook my head.

"Fully fashioned stockings are made from sheer nylon and are sized to the height and shoe size of the wearer and have no stretch in them as there is no lycra contained in the yarn," Mrs Cashmore said very matter-of-factly.

I looked at her quizzically.

She put her tea cup down in the saucer, straightened the hem of her skirt primly, and glared at me.

"So if one were to put undue pressure on the yarn it will become misshapen... like this!" Mrs Cashmore dramatically pulled a stocking stuffed down the side of her seat cushion and tossed it on the coffee table between us.

She leaned down and straightened the stocking out on the table.

There was an obvious bulge in the nylon near the calf which was stained with a silvery discolouration that I knew was dried semen.

"Is it possible the imperfection in this stocking might fit your erect penis William?" she sneered at me.

I blushed and I felt faint. My head was spinning and my ears were filled with white noise. I couldn't think; I definitely couldn't answer her.

"You don't look well. Let me get you something stronger," she said getting up out of her chair and walking to the small bar she had laid out on sideboard.

"You think you know a lot about me William but you don't. But I know a lot about you," she said with her back to me pouring a liberal amount of gin into two crystal glasses.

"I know that you have been snowdropping my knickers and nylons off my washing line."

"I know that you follow me to church every Sunday and that you ogle my bottom and legs."

"I know that you broke into my house last Sunday using the spare key I keep hidden under the garden gnome in my front yard."

"I know that you rifled through my lingerie in my bedroom. You really should have paid more attention when you replaced my delicates back into the drawers. We women are very particular about how we arrange our, what did my grandmother call them, unmentionables."