Walk a Crooked Milf Ch. 02

Chapter Two - Don't Be a Sissy!

"I'm not sure I like you referring to me as a MILF," Mrs Cashmore said.

I had counted the hours until I was back in Mrs Cashmore's house. Much to my mother's regret I had not elected to go on to university and had taken a job in a hardware store to help my mother pay the bills. I had told her that I intended to continue my education when our finances allowed it.

The reality was that I was now so infatuated with Mrs Cashmore that I could hardly think of anything else.

She greeted me at the door as usual but she showed me no signs of affection. It would appear that intimacy was to be confined to the basement. One again we sat in the reception room drinking tea. As it was Monday Mrs Cashmore was not dressed for church but she was still dressed sophisticatedly: skirt, blouse, nylons, heels and full makeup. I noticed her nylons were fully-fashioned with seams running up the back of her legs.

I felt a tinge of jealousy knowing that she would be servicing clients later that evening after I had left. She had told me so. She said that I would stay until eight thirty but then I would have to leave as she had a gentleman caller arriving at nine.

"The MILF thing is American slang; I heard it in a movie but I'll stop using it now that I know you don't like it," I replied.

"You're a good boy sometimes William. Now we don't have much time so would you like to adjourn to the basement?" she put down her tea cup.

I nodded vigorously and she smiled at my enthusiasm.

"Come," she said and I followed her downstairs.

"You may undress. Put your clothes over there on the bed," she said without any preamble and I did as I was told.

Sitting naked across from her on the overstuffed sofa with my cock standing erect I felt vulnerable but also very excited.

"We still haven't dealt with the issue of you wearing my clothes have we William?" there was no need for me to respond; I knew the question was rhetorical.

"You showed me how you masturbated into my stocking last week and it was a very impressive demonstration too. Now I want to see what you did with my lingerie; how you wore it, how you felt when you wore it. Let's explore that today William," she said, studying her fingernails as if it was just a whimsy.

I couldn't help blushing even though we had already been through all the tawdry details.

"Don't be shy William. Go over to my armoire and select similar garments to those you took from my laundry basket and wore without my permission," Mrs Cashmore said curtly.

I walked over the armoire and opened it as I had been ordered to. My erect cock twitched as I looked at the lingerie, fetish clothing, high heels, boots and feminine attire on display. I would really like to see Mrs Cashmore dressed in some of the fetish clothes but I concentrated on the task at hand.

I selected a white satin and lace garter belt, matching full-cut nylon panties and a pair of black fully-fashioned stockings and returned to stand in front of Mrs Cashmore with my head bowed.

"Don't just stand there; put them on," she ordered.

I shimmied into the garter belt and once again the feel of the silky fabric on my waist and the garters tickling my thighs was unbelievably exciting. I sat down on the couch and carefully rolled one stocking onto my foot and slowly pulled the delicate garment up my leg and clipped the garters to the welt and then I did the same with the other. I shuddered at the feeling of indulgence as the knickers slid up my legs; my cock tented the front of them as I pulled them tight.

"You are very adept at that for a young man whom I assume has little experience wearing lingerie. I presumed that most of your experiences with such garments have been confined to pulling your pudding into them," Mrs Cashmore snipped.

"I used to watch my mother do it," I whispered in reply.

"And did you steal her unmentionables and wank into them you naughty boy?" she sneered.

"No! Of course not! She's my mother!" I spat back.

"Careful with your tone William; you will be punished for your impertinence," she said sternly.

"Now stand up for me please," her voice suddenly became calm and pleasant again.

"You might think you know how to wear these delicate items but you are lacking some finesse," Mrs Cashmore said getting up off the sofa.

She stood before me and hitched the garter belt higher up on my waist. The feel of her fingernails on my flanks was very arousing especially when she set about straightening the garters and smoothing out my knickers.

"You are correct in putting your knickers over your garters for obvious reasons; you can lower them without having to unclip the suspenders but the belt should be worn a little higher on the waist. This thing is spoiling the effect of your knickers but we will do something about that later," she said and squeezed my cock causing it to throb.

She dropped to her knees and I hoped beyond hope that she might do something with her mouth or her breasts like she had before but she didn't.

"If you are going to wear fully-fashioned stockings you need to ensure that the seams are straight at all times," Mrs Cashmore unclipped the snaps on my garters, four on each side.

She rolled down my stockings and had me lift my feet one at a time to take them off.

"Now pay attention," she said, lifting my right foot off the floor.

I braced myself by leaning onthe arm of the couch.

"To put your nylons on, gather the length of the stocking and carefully put your toe in the end, pull the stocking over your foot and ensure the ankle is correctly in place. Then gradually pull the stocking up checking that the seam is straight," she explained as she pulled the gossamer garment up my right leg and fastened the garters to the welt.

"It's actually harder to put retro seamed stockings on straight as there is less of a guide for your finger to follow. Don't try and adjust the seam on the leg, but roll the nylon down as far as needed and try again," she demonstrated as she put the other stocking on my left leg.

"Now go and stand in front of the mirror and look for yourself," she patted my derriere and sent me on my way.

The stockings were perfect, the welts high on my thighs with just a little creamy white flesh showing between the welt and my knickers which were tightly cinched to my body except where my erect penis distended the front of them.

"Now come over here William and we will discuss what your punishment should be for wearing my lingerie when you broke into my house and also for using those harsh tones with me," she strode purposely over to the vinyl-covered restraint table.

"I thought we were done with that Mrs Cashmore. I was hoping that you'd invited me over for another shag," I said petulantly.

"Get over here!" Mrs Cashmore stamped her foot and looked angrily at me.

With my short stature and slim body she seemed to tower over me.

I didn't resist when she turned me to face the table and secured my hands into the restraints. I had to stand on my tiptoes to stay upright which pushed my bottom out.

I heard the muffled click-clack of her heels on the rubber matting as she angrily paced around the room.

"I thought I had taught you some manners William Baxter but you seem to have taken my kindness for granted. I can't have you doing that," she said.

I heard the swish of a cane and then a searing pain spread across my buttocks.

"Ow!" I cried out.

"Don't be a sissy!" Mrs Cashmore screeched and bought the cane down on my buttocks again.

I writhed and wriggled as the burning pain in my backside intensified.

Mrs Cashmore was standing beside me as she caned me and the closeness of her body and the scent of her perfume had a bizarre effect on me. Despite the agony I felt as the cane came down repeatedly on my bottom I remained aroused and fully erect, in fact I was trying without success to rub my panty-clad cock against the table.

"You're learning William. Not all pain is bad; sometimes it's exciting... it's delicious... it's addictive," Mrs Cashmore squeezed my cock through my panties and brought the cane down again on my bottom.

My bottom smarted like it had been stung by a wasp but the feeling of the cane coming down on my delicate flesh encased in the nylon knickers whilst Mrs Cashmore squeezed my cock through the diaphanous fabric contrived to bring about the most exquisite feeling, a combination of pleasure and pain. The sensation of the silky stockings on my legs added to the mixture of excitement and trepidation; the coalescence of lust and agony.

"There's a good boy William," Mrs Cashmore cooed as I stopped wriggling and offered her my buttocks willingly.

She stroked my cock harder and a globule of semen blossomed in the front of my knickers and began to spread as I ejaculated.

My testes ached and my scrotum contracted as Mrs Cashmore extracted every drop of my issue into my pristine white nylon knickers. The sensation was indescribably intense as she continued to cane my burning buttocks until I was spent.

I collapsed onto the table as my legs gave way and if it wasn't for the wrist restraints I would have fallen on the floor.

"Come on William, don't stop with a job half done," Mrs Cashmore said unbuckling my wrists.

As I sat on my haunches, panting and gasping Mrs Cashmore straddled me and pushed my head under her skirt.

"Go to work boy; you'll soon figure out what to do," she said as she pushed my face into her groin

Her translucent panties were soaked with her vaginal juices and the musky smell of her sex pervaded my nostrils which caused my shrinking penis to become instantly tumescent. I lapped at the delicate folds of her sex through the gossamer fabric and Mrs Cashmore moaned with desire. She pushed my face harder into her pubis and I eased aside the gusset of her knickers and licked and sucked the fleshy creases and crinkles of her vagina.

I had no idea what I was doing but I seemed to be doing it well because Mrs Cashmore's legs were quivering and she was moaning like a slattern as she mashed my face into her sopping maw. My tongue found her clitoral hood and the delicate little bud inside it and as soon as I lapped at it I knew I had found the epicentre of her desire because she actually screamed.

I took my cock out of my knickers and put my hand on my throbbing member and stroked it vigorously as Mrs Cashmore writhed and wriggled on her heels until she fell against the restraint table in order to stay on her feet. Her legs were buckling and her heels jittering on the floor and I flickered my tongue on her clitoris and stroked her legs with my free hand, the other busy stroking my cock.

Mrs Cashmore howled and pushed my face against her sex and a fresh efflux of vaginal secretions drenched my face. I suspected that I had bought her to extremis and the notion caused me to orgasm along with her. I knew that my semen was splashing on her ankles, soaking into her stockings and I would likely be punished for it but I didn't care.

The warm glutinous spattering of my spunk on Mrs Cashmore's legs seemed to heighten her climax and she writhed and shuddered and held my face so tightly to her sex that I thought I would suffocate but I knew better than to struggle. I continued to lap at her sopping sex until her orgasm abated and she pushed my face from under her skirt and I fell to the floor.

We both took some time to regain our composure.

"You seem to have cheekily enjoyed yourself at my expense young Mr Baxter," Mrs Cashmore straightened her leg and pointed it at me.

Thick gobbets of semen were stuck to her calves, darkening her stockings and beginning to dribble down her ankles.

"You know what to do," she shook her leg at me.

This time I was not repulsed at having to lick up my own semen. In fact sucking my spend out of Mrs Cashmore's stockings whilst they still sheathed her legs was quite pleasurable. Any opportunity to touch Mrs Cashmore was a blessing and I took my time lapping at her calves and ankles until she became impatient and shook me off.

"You wretched lad; I can't believe that you are concupiscent again," she pointed the toe of her high heel at my erect penis.

"Well you can take care of yourself at home. I have a gentleman caller to prepare myself for. Now take off my underwear, take it upstairs and put it in the washing basket in bathroom and don't play with any of my unmentionables!" she warned.

I carefully undressed and padded upstairs and dropped the knickers, stockings and garter belt into the hamper and raced back downstairs to the dungeon.

Mrs Cashmore was undressed and sitting on the sofa wearing a silk robe, sipping a gin and tonic; a cigarette smouldering in the ashtray.

"Get dressed and leave. I have left a present for you on the restraint table," she said dismissively.

I gathered my clothes off the bed and quickly dressed. Lying on the restraint table were Mrs Cashmore's stockings, the ones I have spunked over. I snatched them up and stuffed them in my pocket and made my way up the stairs. I could tell that Mrs Cashmore was impatient for me to be gone.

When I left she went over to the video camera, removed the cassette tape and wrote the particulars on the label. I had no idea that she was recording our every meeting... but I would find out eventually.

*****

My fascination and compulsion with Mrs Cashmore consumed me. I became distracted both at work and at home; all I could think about was when I would get to see her again and what we do when we met. I was in an almost constant state of sexual arousal and found myself regularly relieving my frustrations, usually into one of Mrs Cashmore's stockings.

My mother became exasperated with me. When I was home I spent most of my time in my bedroom watching Mrs Cashmore's house, hoping to catch a glimpse of her. Mrs Cashmore teased me. Whenever she was outside she would show off her breasts, legs and bottom, never looking up at me but knowing I was there watching. She would adjust a garter on a stocking that didn't need adjusting or straighten a seam that didn't need straightening and once she even hiked her skirt up all the way around her waist and adjusted her pantyhose gusset.

"I don't understand your fascination with that wretched woman," my mother whined.

"You don't know her. She's a very nice lady," I defended the woman of my dreams.

"She's a whore and a slattern. I don't want you going around there anymore!" my mother screeched at me.

Of course I ignored her.

What made me even more frustrated and jealous was the stream of gentleman callers who came and went during the evenings. I knew why they were visiting Mrs Cashmore and in my mind I conjured up visages of the men enjoying the delights of Mrs Cashmore's body. This drove me insane with envy and I would find relief with my hoard of stockings and knickers.

Mrs Cashmore seemed to deliberately taunt me. Sometimes she would invite me around two days in succession and sometimes she would make me wait a week between visits. I knew that this sporadic pattern was deliberately contrived to ensure that I didn't become complacent. Whenever she allowed me to see her I was so grateful that I would do anything she asked.

I was always humiliated, made to wear knickers and stockings, caned, whipped and beaten; teased until I begged for release and I was so beholden to her when she finally gave me the satisfaction I craved I was at her mercy. She usually made me service her with my mouth and I became good at it under her tuition.

I have to say that despite the longing, the pain, the teasing, the continual deferment of release, I came to crave it.

Mrs Cashmore had turned me into her willing slave; a hostage to her whimsy... and I loved it.

"I think it's time to move forward William we seem to be stuck in a rut," Mrs Cashmore said one Sunday afternoon.

She was sitting across from me wearing a black leather catsuit with five-inch high heels and severe makeup. She had refused my continued requests for her to wear the fetish clothing that she kept in armoire until I finally stopped begging. Only then did she decide to wear the dominatrix inspired attire, subtly letting me know that she would make such decisions.

I nodded vigorously. Whatever Mrs Cashmore wanted do, I wanted to do it with her.

"Follow me," she demanded and I did as I was told.

I followed her to the small bathroom, my eyes locked on her tight buttocks swathed in the tight black leather.

"Stand here," she stopped me directly in front of the mirror, under the bright overhead light.

I was naked and erect as I almost always was in her presence, and she studied my body carefully.

"Ok. Keep perfectly still and have some patience," she said as she sorted through the grooming implements laid out on the vanity.

She filled the sink with hot water and dipped a badger-hair shaving brush into it. She took a stick of shaving soap and whipped up a hot creamy lather which she applied to my face.

"You don't really have any facial hair to speak of just light fluff but we need it gone," she said as she carefully shaved me with a safety razor.

It felt quite pleasant being shaved by Mrs Cashmore, rather decadent.

She lathered and shaved away the few sparse hairs on my chest and legs.

"Now make sure you don't move," she said and surprised me by lathering my pubic hair.

Mrs Cashmore shaved away the little coils of hair in my groin and then carefully shaved my genitals. My penis obligingly remained erect and out of the way to facilitate her endeavours. She gave it a friendly little tug when she finished.

"Ok, let me see," she studied my face for a while and then picked up a pair tweezers.

Mrs Cashmore plucked my eyebrows, shaping them to her satisfaction then she gave me a hot towel to wipe away any remaining lather.

"Are you ready?" Mrs Cashmore asked.

"For what?" I asked; the trepidation evident in my voice.

"For whatever I want to do to you silly," she giggled.

I nodded my compliance.

"Don't worry you silly boy. This won't hurt... in fact I think you'll like it," she stroked my face.

"Just keep standing still for a little while longer," she whispered in my ear.

I was surprised when Mrs Cashmore opened a drawer in the vanity and began to take out cosmetics which she placed in the order that she intended to use them.

"I'll do this today but you will have to learn to it yourself eventually," she muttered as she began what would soon become a commonplace ritual.

She applied liquid foundation to my face with a small sponge and then a layer of finishing powder with a makeup brush.

"We have created a blank palette on which to work," she explained.

She applied some shading and blush to my cheeks and spent some time putting eyeshadow on my eyelids and used an eyebrow pencil on my freshly shaped eyebrows. She then applied a thick line of black eyeliner to my upper eyelids and a thinner line to my lower lids and then a heavy coating of black mascara to my eyelashes. She finished the task by applying ruby-red liquid lipstick to my lips, taking time to shape them, letting the colour coat dry and then applying the clear topcoat.

Because she had to work so close to me she continually brushed against me, her sweet breath fluttered on my face and her perfume assailed my nostrils. The feel, smell and taste of the cosmetics that she was applying to me was also decadent and titillating. My cock was so hard that it hurt.

Mrs Cashmore hadn't finished preparing me yet. She brushed out my shoulder length hair, parting it in the middle and combing the front into a fringe which she straightened as best she could with her manicure scissors.

"You will need to go to a hairdresser and get something done," she tutted.

I had no intention of doing so but I remained silent. I would allow Mrs Cashmore to dress me in female undergarments and had even succumb to her feminising my face but there was no way that I was going to get an effeminate hairstyle.