Walk A Crooked Milf - Chapter 1

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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 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 whips 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.”

“I know that you masturbated using that nylon stocking right there on the table and I strongly suspect that you were sniffing the semen-crusted knickers I found in my washing basket next to the stocking.”

“What else you did I can hardly imagine but I know that boys your age are often infatuated with mature women like me so I’m probably better off not knowing. Your depravity knows no bounds but I strongly suspect that you might have tried on some of my underwear,” Mrs Cashmore finished her diatribe and handed me a very strong gin and tonic before she sat back down across from me with her own drink.

Even though I was speechless and ready for an axe to fall on me from great height I couldn’t help but noticing a quick flash of pink panty as she sat down and adjusted her skirt.

I began to stammer and stutter, making no sense and Mrs Cashmore held up her hand to stop me.

I swallowed a mouthful of liquor and was barely able to keep it down as she kept talking.

“Did you really think I wouldn’t notice the semen soaked knickers and stocking at the bottom of my laundry basket?” she asked, sipping her drink.

I knew the question was rhetorical and just bowed my head.

“Did you really think that I wouldn’t figure out that you were the knicker-nicker taking my unmentionables from my washing line?” she smiled conspiratorially.

I remained silent, dreading Mrs Cashmore's wrath. I guessed that we would soon be adjourning to my house and confronting my mother.

“Ok. Enough for now. Take your time. Drink your drink, and here; have a cigarette,” she shook a packet of Benson and Hedges and offered it to me.

I took one and so did she. She picked up a silver table lighter and gave it to me.

“A gentleman offers to light a lady’s cigarette for her William. You have some manners to learn and I am just the lady to teach them to you,” she chided me.

I took the lighter and ignited it and offered it to her and she leaned forward and lit her cigarette. I noticed that the filter of the cigarette was stained by her red lipstick. I seldom smoked but I lit my cigarette and drew deeply on it.

“I'm sure your mother has done an excellent job raising you Jonathan, but there are some things that mothers can’t teach their sons. How do you think I should punish you for breaking into my home and invading my privacy?” she said, blowing smoke towards me.

“I, I don’t know,” I stammered.

“I bet you do. What you did with my unmentionables was degrading and disgusting. You’re an intelligent boy. Don’t you think that your punishment should be equally degrading and disgusting?” she took a long drag on her cigarette and so did I.

“I’ll take your silence as concurrence,” she smiled at me after a long pause.

“Pick up the stocking!” she growled, her pleasant tone suddenly changing to anger.

I was shaken from my reverie and I put down my cigarette and picked up the offending item. It felt familiar in my hand: cool, sleek, sensuous.

“Show me what you did with it. Show me the vile corruption you endowed on one of intimate possessions,” Mrs Cashmore demanded.

“Well I…” I began to explain what I did.

“Don’t tell me you idiot! Show me!” her face contorted with rage and I was genuinely scared.

“Show you?” I whimpered.

“Oh fuck it! Let’s just go next door and see your mother,” Mrs Cashmore was exasperated and she started to rise out of her chair.

“No, no, no, no! I’ll show you!” I beseeched her.

She sat back down and I fumbled with my belt buckle. I dropped my pants, unable to look at her I felt so ashamed.

“Go on,” she urged me, lighting another cigarette.

I dropped my underpants and stood there with my jeans and underwear bunched around my ankles, shaking like a coward. My hands were trembling as I reached for the stocking and opened the dark welt and put my flaccid penis inside it. Despite being very well endowed, my penis looked like a shrivelled snail to me.

I imagined that being in the presence of the woman I had always adorned with her stocking draped over my cock would have been the most exciting thing that could ever happen to me but I was simply mortified.

Mrs Cashmore sniggered and I felt totally ashamed.

“Does this help?” Mrs Cashmore opened her legs and exposed her stocking top and the V of her pink satin panties.

Now I was looking!

She looked so sexy with that sneer on her red lipsticked lips, her heaving breasts, her long gossamer-sheathed legs opened slightly and her tight skirt hiked up her thighs.

She took a long draw on her cigarette and eyes bore into mine.

I was instantly erect.

“Show me,” she whispered, a long finger snaked down to her pubis and circled her vulva through the pink satin.

I gripped my cock encased in the sheer stocking… her stocking… the woman sitting in front of me with her legs open… the woman lewdly circling her finger on her panty-clad sex… that woman… the love of my life… Mrs Cashmore.

She gasped when my cock quivered and a gobbet of steamy semen erupted from my penis. Another followed, ropes of musty viscous spend spattered on the table and on then on the floor.

I was so overwhelmed with the power of my orgasm that I had to hold onto the coffee table so I didn’t fall over.

When I had finally finished ejaculating I was able to stand tall, my long thick cock standing proud with the sheer stocking still encasing it, a pool of white semen clinging to the fabric stuck to my glands.

Mrs Cashmore closed her legs and demurely straightened the hem of her skirt and then she started to slowly clap.

“Bravo! Bravo!” she cheered but I felt the sting in her voice.

“Now clean it up!” she snapped.

I leant down to pick up a napkin off the coffee table.

“Not with that you silly boy!” she berated me.

I pulled the stocking of my slowly deflating penis and began to ball it up.

“Definitely not with that you fool!” she hissed.

“With what then?” I snapped back at her, instantly regretting it.

She just glared at me and I suddenly knew what she meant.

I had never felt so degraded as I did that day when I got to my knees and licked up my own semen. It wasn’t the taste; of course I had tasted my own semen before; what teenage boy hadn't? It was the humiliation of having to kneel down with my trousers and underpants around my ankles in front of this beautiful elegantly dressed woman and lick my seed off the table and then off the floor.

The final insult was that she made me suck my semen out of the stocking. I felt hopelessly degraded and useless.

But why was my cock so hard? It had returned to full tumescence.

Mrs Cashmore chuckled.

“Give me the stocking you silly boy,” she held out her hand and I gave it to her.

“Now stand in front of me,” she ordered.

I lasted all of thirty seconds when Mrs Cashmore draped that stocking over my quivering cock and gently stroked it.

“Good boy,” she cooed as she milked every last drop of my seed from my throbbing organ.

My knees trembled and Mrs Cashmore let go of my phallus.

“You may wipe up your mess with my stocking this time. Keep it as a souvenir. Lock the front door on your way out and be here next Sunday at two PM sharp. Do not be late!” she called over her shoulder.

I listened to the click of her high heels as she ascended the stairs to her bedroom and from that moment on I was Delores Cashmore’s chattel. I would do anything for her.

*****

I don’t know how I managed to wait a full week until I could once again visit Mrs Cashmore. I was in agony, the agitation and suspense actually made me physically sick. Mrs Cashmore was right their next door. I could see her from my bedroom window when she came outside, which she did quite often to potter in her neat garden or to hang up her washing.

She knew that I watching her and she knew that I knew she knew. She deliberately straightened a seam of her stocking or hiked up her skirt to adjust a garter or if she was wearing pantyhose she might ‘accidently’ have caught the back of her skirt in the waistband so I could see her knickers over the diaphanous sheer-to-the-waist gusset. The stocking that she had given me was a cum-soaked tattered ruin within three days.

My mother asked me what was wrong. Was I coming down with something? Did I feel alright? Yes I was coming down with something… infatuation with Mrs Cashmore and no… I wouldn’t feel alright again until I was inside Mrs Cashmore’s house.

I watched Mrs Cashmore return from church the following Sunday with both trepidation and excitement. She was wearing a tight fitting navy blue suit, white satin blouse, sheer tan hosiery and black high heels. Her flaming red hair and signature bright-red lipstick were like beacons calling me like a moth to a flame.

At exactly two PM I knocked on the door and she answered immediately.

She said nothing as I followed her inside, my eyes locked on her buttocks and those long shapely legs. She gestured for me to sit across from her, demurely pulling her skirt under her legs and crossing her ankles. But there was nothing demure about Delores Cashmore; she radiated sexuality.

“I see you are pleased to see me,” she pointed at the bulge in the front of my trousers.

I just nodded stupidly.

“Plenty of time for that; let’s have tea,” she poured English Breakfast from a hand-painted teapot which matched the service laid out on the coffee table between us.

I was so nervous that the cup rattled in the saucer when I picked it up.

“We need to address the rest of your indiscretions William,” she announced, sipping her tea.

I had no idea what she was talking about.

“You really are a stupid boy; I don’t know why I allow you in my presence,” she sounded exasperated.

I began to panic. The last thing in the world I wanted was to be dismissed by this woman.

“Yes I am stupid Mrs Cashmore and once again I apologise for breaking into your house but please don’t send me away,” I beseeched her.

“And more specifically what else did you do while you were unlawfully in my house?” she glared at me.

“I wanked… I mean I masturbated with your… your unmentionables,” I stammered.

She smiled at me, amused that I had used her grandmother's word for lingerie.

“And what else did you do that was very, very wrong,” she looked at me over the rim of her teacup.

I was flummoxed; I had no idea what she meant.

“What else did you do with my knickers and stockings?” she asked.

I was still dumbfounded.

“Didn’t you try some of them on?” she smiled at me sweetly but her eyes were cold and they drilled into me.

“Yes,” I whispered, barely audible.

“What did you say?” she growled angrily.

“Yes Mrs Cashmore I tried them on,” I spoke up so she could hear me.

“When you were in my house, did you go down into my cellar?” she changed tack completely and I was thrown.

“No Ma’am I didn’t go down to your cellar; why would I?” I still didn’t know why she was asking me.

The cellar in my mother’s house was dark, cold and uninviting. Years ago it had been used to hold coal for the fire and stove, the coal was dumped down a sluice and stored in a large wooden coffer. Remnants of the dust sometimes stained my hands when I went down there which wasn’t often. It was filled with old furniture and mouldy old clothes and smelled of mildew and mouse turds.

“Follow me,” she said without any preamble as she got out of chair and strode down the small hallway to the cellar door.

I followed her like a faithful puppy.

“Open the door and go down the stairs. I’ll follow and don’t turn around so you can look up my skirt. If you’re a good boy you will get to see what’s under there in due course,” she smiled at me and my cock quivered at thought of whatever delights Mrs Cashmore kept under her skirt.

Mrs Cashmore’s cellar was the antithesis of my mother’s. It was bright and freshly painted, the floors carpeted and the furniture ornate. It even smelled nice, just like Mrs Cashmore’s perfume.

“Take a look around and tell me what you think,” she said casually.

There was a small bar and a mini-fridge set up on one wall and she strode over to pour us both a drink.

There were two overstuffed lounges facing each other with a small table between them and on a purpose-built cabinet was a large-screened television with a video player and recorder under it on a shelf. There was a movie camera mounted on tripod plugged into the recorder. That was where the semblance of anything normal ceased.

One half of the room was not carpeted; it was fitted with rubber matting. On one wall hung a variety of whips, riding crops, canes and lashes. Alongside them hung metal restraints, spreader-bars, handcuffs and leather straps. There was a vinyl-covered table fitted with leg and hand restraints and beside it an X-shaped saltire cross with restraining points for ankles, wrists, and waist. The wall opposite these devices was mirrored from floor to ceiling

In another corner was huge four-poster bed fitted with satin sheets. Beside it on the bedside table were a number of sex toys, some of which I had no idea how they would be used. There was a small ensuite bathroom with a shower in one corner and a huge armoire took almost the whole of one wall.

I was both fascinated and disturbed.

“Your mother doesn’t think much of me, does she William?” she once again segued way off topic.

She was seated on one of the overstuffed lounges and she patted the cushion beside her indicating that I should sit. She had made two gin and tonics and she gave me one when I sat down.

“I’m sorry?” I was disoriented by her segue and our surroundings.

It was surreal sitting in the comfortable lounge whilst across the room was a fully-fitted dungeon.

“Do pay attention William, I said that your mother doesn’t like me,” she sipped her drink and studied me, waiting for a response.

“She says she’s surprised that you are not struck by lightning at the doorway when you go into the church,” I finally answered her.

“Oh my god that’s funny!” she guffawed and patted my knee.

She regained her composure and patted my knee again and removed her hand.

“Do you know why?” she took another sip of her drink.

“She won’t tell me,” I replied.

“You really are a stupid boy sometimes. You spy on me endlessly but you haven’t wondered why there are so many men coming and going from my house in the evenings and late at night,” she put down her drink and took my hand.

I looked at her quizzically and she seemed amused at my confusion. She nodded her head at the apparatus on the other side of room.

It suddenly dawned on me!

She was a prostitute. A prostitute who specialises in bondage and discipline by the look of it. My jaw dropped and Mrs Cashmore reached out and closed my mouth.

“Try not look too stupid,” she said sarcastically and offered me my drink which I gulped down.

“I bet you’re very expensive,” I said when I had regained my composure and immediately regretted saying it.

“I’m sorry,” I said before she could reply.

“Oh no William. You are quite correct I am very expensive. Men who have special needs will pay a premium price to get what they want,” she answered.

I just sat there staring at the dungeon on the other side of the room, fascinated by the apparatus.

“Aren’t you curious? Don’t you want to know how it all works? Don’t you want to know what’s in the armoire?” she goaded me.

“Of course I’m curious Mrs Cashmore,” I replied finally.

“Well get up and come over to my playroom and I’ll show you around,” she got up off the lounge exposing most of her thighs which confirmed that she was indeed wearing pantyhose.

She led me to the armoire first and opened it up. It was full of lingerie, fetish clothing, high heels, boots and some nice feminine attire too. The small bathroom was fully stocked with cosmetics, perfumes and other feminine requisites.

Then she led me onto the rubber matted dungeon area.

“You know what these are for, or you can at least imagine I suppose,” she pointed to the canes, whips and lashes hanging on the wall.

I nodded.

“And these?” she pointed to the saltire cross and the table.

“I can guess,” I replied.

“Notice that the table is fitted with a swivel. I can restrain a person on the table and have them standing upright or splayed out horizontally on their back or any position in between,” she lovingly ran her fingers along the vinyl table top.

“And men pay you to be restrained and to be whipped? To be punished?” I reached out and touched the saltire cross.

“Most but not all. Some just want to shag a beautiful mature woman, that’s what that is for,” she pointed her chin at the huge four-poster.

“Ok,” I said softly.

“Isn’t that what you want William? Don’t you want to shag me? Do you think about shagging me when you put my stocking on your cock and sniff my panties?” Mrs Cashmore smiled conspiratorially.

“Yes,” I whispered.

“But not naked William? You yourself want to be naked of course but you want me to keep on my lingerie and my high heels don’t you?” my discomfort pleased her.

“Fully-clothed. Dressed like you are now. Very sophisticated but very sexy,” I surprised myself by even being able to articulate how I felt about her.

“Would you like to do that now William? Would you like to fuck me?” she softly stroked my cheek.

I nodded. I couldn’t speak.

“Well get undressed William, I don’t have all day,” she said and I almost creamed my jeans.

“Really?” I was dumbfounded.

“I’m not going to make the offer again William,” she said curtly.

I was not going to antagonise Mrs Cashmore any further. I raced over to the bed and took off all my clothes and lay down on the coverlet, my cock standing proud like a periscope.

Mrs Cashmore came over and studied my trim pale body. She stroked my face and then ran her fingers across my chest and then down my legs, deliberately staying away from my groin, teasing me.

“I know many a girl who would be jealous of your skin William, it’s smooth, soft and unblemished. You have a narrow waist but wide hips and plump buttocks. You’re quite effeminate aren’t you?” she removed her hand from my body.

“I wasn't particularly sporty at school. I was the last to be picked for football and I was teased about being unmasculine if that’s what you mean,” I answered.

“I bet you were; but this isn’t what I had in mind,” she said pointing to the bed.

“Come over here,” she walked over to the saltire cross.

She rubbed up against the cross like it was living being; like she adored it.

“Wouldn’t you like me to do that to you?” she teased.

“Oh god yes,” I sighed.

“Then come here. Put your back against the cross, open your legs wide and put your hands up,” she gave me a devilish smile.

The wooden cross felt smooth and cool against my flesh as Mrs Cashmore secured my ankles in the restraints and then my wrists. I was pinned to the wooden cross, my arms high and wide and my legs wide open.

“How does that feel?” she asked; her body only millimetres from mine, her lips almost but not quite touching mine.

“Strange. Not too uncomfortable but I bet it would be if I was restrained like this for any period of time,” I answered.

“The question was rhetorical really, but thanks for your frank and honest answer,” she stroked my cheek again.

“So if I were to leave the room now and turn out the lights you would be uncomfortable would you?” she chuckled and quickly squeezed my cock and then let it go.

I panicked for a second and strained against my bonds but I couldn’t move.

“So you want to fuck me while I’m fully clothed in my church clothes,” Mrs Cashmore stepped close to me.

“You're what I call a MILF,” I answered truthfully.

“A vile Americanism; but I suppose it’s an adequate label,” she sniffed.

She was so close to me that the very tip of my cock was rubbing on her leg, her sweet breath was on my face, her lips were nearly touching mine.

“Oh god yes,” I groaned.

“Well as you have been a good boy this week I think I might grant your wish,” she took a step back and my disappointment showed.

“So maybe you would like to look first. Sort of get a peek at what’s on offer so to speak,” she unbuttoned her blazer and the slowly began to unbutton her blouse.

I stared at her fascinated as she unbuttoned her blouse so that she could reach inside it and undo the catch on her brassiere. It was the type that had the clasp at the front between the cups and her soft ripe full breasts fell from the cups and she hefted them in her hands.

“Do you like them? I know that you're a leg and bum man but you have to admit that they are impressive,” she goaded me, bringing the milky orbs close to me and rubbing them on my body.

Her flesh was warm and soft and her nipples hardened as she circled her breasts on my naked chest.

“I have one punter who is a real tit man William. He just loves to play with my breasts and nothing else. He will suckle on them like a baby for hours if I let him,” she continued to press her breasts against my naked flesh.

“You know how I get him off? I do this,” she smiled whimsically at me and dropped to her knees.

She nestled my cock between her breasts and began to knead it between them.

“Oh my god!” I groaned.

It felt amazing. I felt my scrotum contract as my orgasm approached. I didn’t want to come so soon but there was nothing I could do about it being trussed to the cross as I was. Globules of pre-ejaculate dribbled from my cock and smeared on Mrs Cashmore’s milky orbs.

“Ok enough of that,” Mrs Cashmore said in an unaffected tone and removed my penis from between her breasts and got to her feet.

My body was contorted and my cock literally twitching I was so close to climax.

“Please Mrs Cashmore. Please finish it,” I begged.

“Patience William; I thought you wanted to shag me. Wouldn’t you rather wait a while so you can put it here,” she hiked up her skirt and revealed a pair of tight black bikini panties over sheer-to-the-waist pantyhose.

She pointed a finger to her pubic mound.

“Oh god yes,” I whimpered.

“Well, just have a little patience my boy,” she said pulling down and smoothing her skirt.

“I’m not a boy! I’m eighteen years old!” I rallied, and strained against my bonds.

“Besides, you told me you didn’t have all day!” I shouted at her.

Mrs Cashmore stood dead still and studied me for a moment and then she suddenly slapped me across my cheek.

“Don’t be insolent William. I don’t have all day. I have things to do. But you have as long as I say you have,” she turned her back on me and walked over to the staircase and ascended the stairs.

She opened the door, turned out the lights and closed the door behind her leaving me alone and bound to the saltire cross.

I don’t know how long she left me like that alone in the dark. It was probably no more than thirty or forty minutes but it seemed like an eternity. The cellar was well insulated so I wasn’t cold but that also meant that I couldn’t hear Mrs Cashmore above me in the house. Was she even still there or had she gone out?

I began to doze fitfully when suddenly the fluorescent lights flickered on and I heard her heels descending the stairs. She walked up to me and without a word she pressed her body against me and kissed me. My cock immediately sprang to attention. The feel of her body against mine, the sensation of her cotton skirt and satin blouse against my skin was quite carnal, her soft lips pressed to mine was breathtaking, she slipped her tongue into my mouth briefly and squeezed my cock and I thought I would explode but she stepped away from me as suddenly as she had embraced me.

“I just wanted to make sure you were comfortable,” she smiled at me and ran a fingernail down my hairless chest.

“I’m far from comfortable,” I snapped.

My wrists were sore and my legs were aching.

“The statement was rhetorical William. I’ve finished my washing now I’m going to hang it out to dry. Clothing feels and smells so much better when it’s dried out in the sun,” she turned away from me walked towards the stairs.

“No! Please! Come back!” I begged her, but she didn’t answer and soon I was back in darkness and silence.

This time it seemed like she had been gone an hour before she returned. I had learned my lesson and said nothing as she approached me, still dressed in her church clothes.

“Do you have a girlfriend William? If you do has she ever done this?” unexpectedly Mrs Cashmore dropped to her knees and took my flaccid penis in her mouth.

I became instantly erect as she used her lips and tongue on me, brining me to full tumescence. Her warm wet mouth on my throbbing appendage felt like nothing I had ever felt before. She used her lips to suckle my shaft whilst her tongue circled my glans.

When I was close to extremis she stopped and got to her feet.

“Did that feel nice William?” her lips brushed my earlobe as she whispered.

I just nodded.

I was close to orgasm and had been bought to so close to climax so many times that my testes ached and my cock yearned for release.

“Not long now William and you will have what I have promised you,” she bit my earlobe.

This time it came as no surprise when she left me alone in the dark.

Time passed slowly and became interminable. I sagged against my bonds. I didn’t know what I wanted more, release from unrequited sexual arousal or release from my bonds.

The lights suddenly came on and Mrs Cashmore strode purposefully over to the saltire and stopped in front of me. She didn’t say anything but her eyes were lit with excitement and she was breathing heavily. She hiked up her skirt and put her hand in her knickers and I heard the sound of rending nylon. Mrs Cashmore had torn a hole in the crotch of her pantyhose.

She put her feet wide apart and approached me with a waddling gait. When she was directly in front of me she took my hard cock and nestled it inside her knickers, through the hole in her pantyhose and placed at the entrance to her sopping wet vagina. She put her arms around my neck, closed her legs a little and impaled herself on my cock, driving it inside her all the way to the hilt.

The feel of her hot, moist sheath encasing my bloated aching manhood was indescribable. She put her mouth on mine and drove her tongue into me as she began to fuck me, grinding her sopping minge against my pubic bone to enhance her pleasure.

I wanted to hold her, to put my arms around her, to pull her body against mine but she was in total control. She must have read my thoughts because she put her arms around my body and rubbed her thighs against mine and began to grind as she kissed me harder and more passionately.

We orgasmed simultaneously; my cock pulsing and quivering as I spurted stream after stream of scalding ejaculate deep inside her. I felt her cunt contract and convulse as she hung onto me, crying out into my mouth. Her fingernails raked my flesh eliciting a stinging and burning sensation that melded with my orgasm and brought me to a higher peak.

The tremendous feelings of pleasure and release as I climaxed contrasted with my inability to move and the sharp biting pain of her fingernails scouring my flesh was astoundingly lascivious, almost overpowering.

When we were both done Mrs Cashmore clung onto me, gasping and shuddering until she was able to stand. When she extricated herself from me I saw a trickle of my spend dribble from her cunt and soak into her nylons.

She stepped away from me and keeping her skirt hitched up out of the way she stepped out of her high heels and pulled off her nylons and panties, bunching them around her ankles. She picked the tangled mess of pantyhose and knickers and draped them over my still erect cock.

“You can keep these too,” she said, still a little breathless.

“Get dressed. Let yourself out. Be back here at seven PM tomorrow; I have more to teach you,” she reached up and released my wrists and when she did so I tried to kiss her but she pulled her face out of the way and scowled.

“You can unshackle your own ankles,” she said and walked away carrying her heels.

*****
The curtain tweaked as Mrs Cashmore watched me walk down the path and then she went back down to the cellar. She turned off the movie camera and removed the tape from the video recorder. She wrote the details on the spine of the cassette tape and opened the cupboard built into the TV cabinet and placed the tape carefully on the shelf alongside a multitude of others.

To be continued

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Comments

Glorious Humiliation

joannebarbarella's picture

What teenage boy has not dreamed of being "educated" by a sexy mature woman with no scruples?

I won't speculate as to where this is going but William is going to be utterly degraded.

I'm curious.

Where did the expression 'Snowdropping' come from for nicking washing of the clothesline. Seventy-four years trans and I've never encountered it before.
Beverly.
xx

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