Walk a Crooked Milf Ch. 01

"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 William, 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 my most 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 a 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 to 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.