Walk a Crooked Milf Ch. 02

"A final touch," she said spraying me liberally with perfume.

"Go over to the bed now and you will find that I have laid out some clothes for you. Put on the suspenders, stockings and knickers and I will help you with the rest," she patted me on the backside and sent me on my way.

I went through the usual ritual of putting on my stockings and knickers. I had become quite adept at this but the thrill of the garments against my flesh never dissipated and in fact was exaggerated now that my legs and pubis were freshly shaved.

"Ok now for something completely different, as our friends in Monty Python are want to say," Mrs Cashmore picked up an item of clothing off the bed.

"I know that you have always been captivated by my Sunday church attire so I think it's only fair that you get a chance to wear it yourself," she stated, holding up a pristine white, long-sleeved satin blouse.

"Put your arms in the armholes just like you are putting on a shirt. You might find buttoning the blouse is a little uncomfortable at first because it buttons the opposite way to a man's shirt," she explained.

She was right; I struggled to button the blouse but she assisted me. The feel of the cool satin on my skin was very pleasant. She picked up a navy blue skirt which she held open for me.

"Step into this. You may put a hand on my shoulder to steady yourself," she stipulated.

I carefully stepped into the skirt which she pulled up to my waist, tucked in the blouse and zipped closed. She smoothed it out and straightened the hem which rested six inches above my knees.

"This skirt has a kick-pleat in the rear which will help you walk as it is quite tight around the thighs," she explained.

What she didn't need to explain was how delightful the hem of the skirt ruffling around my stocking-sheathed thighs felt.

"Now. Sit on the bed and we will deal the most difficult part of your transformation," she gently pushed me back onto the four-poster.

"I took the liberty to look in your shoes and saw that you are a size eight. These are a ladies size nine and may be a little tight but we will see won't we?" she said as she pushed a black, patent leather high heel on my fright foot.

"Just as I thought; it fits perfectly but we won't really know until you walk in them," she said as she put the other shoe on my left foot.

"Now stand up carefully and let's have a look at you," she said.

I got shakily to my feet and had to put a hand on Mrs Cashmore's shoulder to stay upright. I took my first tentative steps in the four-inch heels, biding Mrs Cashmore's advice.

"Keep your spine straight and thrust your weight forward onto your toes. Allow your knees to bend and turn your feet out slightly so your inner thighs are turning to the front. Always lead with the ball of your foot so that it touches the ground just before the heel and place one foot in front of the other," she explained as she led me slowly around the room.

I felt awkward and stumbled a few times but with some encouragement and holding onto Mrs Cashmore when necessary I managed to complete two laps around the room.

"Good boy," she said as we stopped in front of the mirrored wall.

"Look how lovely you are," she pointed to my reflection in the mirror.

I saw myself completely transformed and feminised for the first time and I was amazed. I was captivated by my reflection. I didn't recognise myself.

What I saw in the mirror was a beautiful sexy young woman. She was flat-chested but other than that she was stunning.

"Say hello to Wendy," Mrs Cashmore whispered in my ear.

"Wendy?" I whispered, unable to look away from my reflection.

"Yes Wendy. When you are dressed like this, which will quite often from now on, you will be Wendy, not William," Mrs Cashmore said in a self-satisfied tone.

"Let's put on the jacket. We'll put something in a bra next time to give you some cleavage but let's see how you look fully dressed," she went to the bed and came back with the blazer that matched my skirt and held it out so I could put it on.

"There; perfect," she smiled as she pulled the jacket down and buttoned the front.

"I have to admit that I quite like being dressed like this Mrs Cashmore, it feels wonderful but I'm not sure I want to be dressed like this every time I come over," I replied.

"You ingrate!" she hissed.

Her pleasant demeanour disappeared and her face became angry and flushed.

She half dragged me across the room to the restraint table; I staggered on my heels and lost a shoe. She slammed my wrists into the restraints and raised the table as high as it would go, forcing me to bend over and push out my derrière. I had no time to make an apology before she hiked up my skirt and began to flail at my buttocks with a leather lash.

This was no playful spanking; it was a flogging and the pain was intense. I cried out in pain and begged her to stop but she didn't stop until I was crying like an errant schoolgirl.

Mrs Cashmore was breathless with exertion when she finally stopped and I lay prone on the table unable to move. My buttocks burned with intense pain.

"You've been a very ungrateful and naughty girl Wendy and I'm very disappointed with you," she panted.

"Stay where you are," she hissed... as if I could actually go anywhere.

I heard her walk away to the bathroom but I couldn't turn my head far enough to see her. She came back forthrightly and pulled down my knickers. I winced and tensed in anticipation of another lashing but I was surprised when I felt her apply a soothing lotion to my buttocks.

The cooling salve immediately alleviated some of the pain and I sighed with gratitude.

"Is that better?" Mrs Cashmore cooed.

"Oh yes thank you Mrs Cashmore," I replied, my gratitude evident.

She poured more of the lotion on her hands and one of them returned to the task of gently massaging my buttocks while the other slipped inside my knickers began to massage my cock.

"What about that? Is that better?" she crooned.

"Oh god yes," I whimpered as I became immediately erect.

Being bound to the table with my legs spread, my skirt hitched up; the taste and smell of the makeup and perfume, the feel of the intimate garments against my flesh was delightfully carnal.

It took only a few seconds for me to erupt into Mrs Cashmore's lotion-coated fingers as she drained me into my knickers.

She wiped her hands and released me from my bonds and eased me to my feet and turned me to face her.

"My pretty girl. My pretty, pretty girl," she cooed and smoothed her fingers through my fringe and then stroked my cheek.

She leaned in and put her lips on mine and in that moment I forgave her everything.

Mrs Cashmore hadn't kissed me since that first visit, deliberately denying me the pleasure of it and the kiss felt wonderful. Our lipsticked lips pressed together and then her tongue tentatively slipped into my mouth and I reciprocated and extended my own tongue. Our kiss, at first soft and loving, became passionate and demanding. My bottom was still tender but the pain was provocative rather than hurtful. I became aware that I actually felt feminine; it was gratifying but at the same time terrifying.

"You know what to do Wendy," Mrs Cashmore said, putting downward pressure on my shoulders.

I dropped to my knees and Mrs Cashmore unzipped the crotch of her catsuit exposing her pubis. The delightful stench of her cunt assailed my nostrils as I leaned in to do my duty.

She came quickly; so quickly that although I was furiously beating myself I didn't have time to come before she lifted me to my feet.

"Come let's take to back to the bathroom and you can practice your makeup," she said, her demeanour now passive.

Mrs Cashmore spent the best part of an hour with me showing me how to apply the makeup and then she wiped it all away and had me shower. She sent me home with the high heels she had bought for me and told me to practice every day. If I was not proficient by the time we next met the consequences would be dire she informed me.

*****

I was not really happy with this new turn of events. As much as I liked wearing Mrs Cashmore's lingerie, I didn't like being forced to wear makeup, a skirt, blouse and heels. I had to admit that for a minute there I did feel very feminine but I did not like being called Wendy and I was definitely not going to get my hair styled. I liked my shoulder-length hair just as it was; at work I put it in a ponytail for safety.

"There! I am rebelling against you Mrs Cashmore!" I called out in my bedroom, fortified by several cans of lager.

That was what I said to myself petulantly as I paraded up and down my bedroom wearing my high heels. So much for rebellion. Mrs Cashmore had told me to practice and so I practiced for an hour every day and longed to once again be in her company. I think she was punishing me because it was over a week before I was invited over to her house again.

"Would you like to come for a drive with me Wendy?" Mrs Cashmore asked.

I cringed when she called Wendy.

We were sitting in her living room and she was dressed in her Sunday church clothes and I desperately wanted to have sex with her. I was of a mind that she was punishing me still. I didn't want to go for a drive I wanted to go down into the dungeon and shag her brains out. She could beat and paddle me senseless if she liked, as long as she got me off.

"I'd be delighted to come for a drive with you Mrs Cashmore," was my reply however.

Mrs Cashmore owned a late model 3-series black BMW which she kept in a detached garage at the side of the house. As well as envying her, I envied her car.

During the drive I kept my eyes on her skirt which crept up her thighs whenever she engaged the clutch or used the brake. She would pull it primly down those firm nylon-clad thighs whenever the car stopped but it would ride up again as soon she put the car in motion.

After about half an hour's driving we pulled into a small cottage and Mrs Cashmore applied the brake and told me to get out.

"Where are we? What are we doing here?" I asked as I alighted.

Mrs Cashmore glowered at me and I knew better than to ask any more questions. Instead I meekly followed her to the front door of the cottage which was opened by a rather pretty buxom lady who I guessed to be in her late thirties or early forties. When we settled inside I noticed the similarity between Mrs Cashmore and the resident of the cottage. They were of similar ages and wore similar clothing and heavy makeup; the combination of their heady perfumes was distinctly exotic. I noticed that the woman was wearing seamed stockings as I meekly followed the two women inside.

"This is Mrs Felicity Bancroft... Felicity, this is William Baxter or sometimes she is Wendy if you know what I mean?" Mrs Cashmore made the introductions.

My face burned bright red when she referred to me as Wendy. Whoever Felicity Bancroft was, she was obviously trusted by Delores Cashmore.

"Pleased to meet you Mrs Bancroft," I shook her hand and sat on a lounge chair across from her and Mrs Cashmore.

You would think that I would be excited being the company of two sexy mature women but I was apprehensive because Mrs Cashmore had not explained our reason for being here.

"So this is your pet project," Mrs Bancroft said to Mrs Cashmore which once again led me to be both quizzical and nervous.

"Yes. As I explained to you over the phone I want you to give William a hairstyle that will suit him in both his male and feminine manifestations," Mrs Cashmore replied.

"I did not agree to this!" I cried and leapt from my chair.

"Behave yourself William! Sit down!" Mrs Cashmore glared at me.

"Now, now, William. I am a qualified hairdresser amongst other things. Despair not; I will give you a hairstyle that will be suitable and stylish however you present yourself," Mrs Bancroft interjected.

"I am very good friends with Delores and I'm quite excited to meet her protégé, she has exciting things planned for you," she continued.

"Enough Felicity! The boy will either do as I tell him to or I won't bother spending any more time on him," Mrs Cashmore said irrevocably.

"Oh come Delores; I know that you are teaching him to be your submissive but in his case I'm sure that you will catch more flies with honey," Mrs Bancroft countered.

"If you behave yourself while I cut and style your hair and I'll give you a little treat," Mrs Bancroft said to me.

The sparkle in her eye made me wonder what that treat might be and her provocative smile set my heart racing.

"Oh you pamper the boy too much Felicity but do whatever floats your boat. I'm off to do some shopping and I'll be back in an hour or two to pick him up," Mrs Cashmore arose and fumbled in her purse for her car keys.

"Be a good girl Wendy," Mrs Cashmore said snarkily and walked to the door.

Being left alone with Felicity Bancroft, a woman I had met only minutes ago, felt both bizarre and exciting.

"Delores tells me that you call her a MILF behind her back. Do I qualify as a MILF?" Mrs Bancroft said when she came back from seeing Mrs Cashmore to the door.

My face became flushed and I felt it difficult to meet Mrs Bancroft's gaze.

She pirouetted in front of me, lifting her skirt a little to reveal plump thighs and dark gauzy stocking-tops and then struck a seductive pose. My cock began to swell.

"You most certainly qualify Mrs Bancroft, but Mrs Cashmore does not approve of me using that term," I said eagerly.

Her pleasant demeanour was a relief after Mrs Cashmore belligerent behaviour. I studied her more closely and decided that this plump lady exuded a sexy seductiveness that matched that of Mrs Cashmore.

"Please, call me Felicity, my mother is Mrs Bancroft. Now come upstairs and we'll get started on your hair," she said and wiggled a finger at me.

I obediently followed Felicity upstairs, my eyes locked on the backseams of her stockings and her ample derriere; my cock throbbing in anticipation of what form my treat might take.

Felicity led me to a spare bedroom which she had fitted out as a hair salon.

"I work from home. Rents on commercial properties are appalling but even so it's hard to make ends meet. Lucky for me Delores introduced me into a secondary occupation that pays very nicely, thank you very much," she winked salaciously at me.

I was no idiot and it dawned on me that Felicity Bancroft also worked as a prostitute. I wondered how many of Mrs Cashmore's acquaintances worked in the same profession.

Felicity sat me in a stainless steel salon chair padded with black vinyl and tied a smock around me. I was grateful because the smock covered the tent in my trousers caused by the proximity of the delectable Mrs Baxter.

"Ok; here we go," Felicity said studying my head briefly before launching into a scissor-snipping dervish-like dance.

I watched her intently, not sure that it was possible to create a hairstyle that suited both a man and a woman. She cut and styled my brown shoulder-length hair and used a balayage technique to put in some lighter highlights. She washed and conditioned it and used a blow dryer and hairbrush to finish the task creating wavy curled tendrils parted just off centre.

It looked amazing.

The whole procedure took just over an hour and it looked very modern and professional.

"That is fantastic," I said when Felicity turned the chair to face the salon mirror and held a hand mirror behind my head so I could see the full effect.

"I'm glad you like it. As you can see it will suit both William and Wendy," she grinned, pleased with herself.

"Do you know why Mrs Cashmore has this fixation for dressing me like a woman?" I asked.

"That's a question best put to her by you. She has told me what you have been getting up to and I have to admit I'm a little jealous. I wouldn't mind having my own toy-boy," she smiled mischievously.

"Which is a perfect segue into me giving you your treat. Delores will be back soon so we better be quick about it; I don't want her finding us in flagrante delicto, she's likely to get angry or jealous," Felicity whipped the smock from me and helped me out of the salon chair.

"What does in flagrante delicto mean?" I asked.

"This," Felicity Bancroft dragged me over to a single bed pushed against the wall and pulled me down on top of her.

I required little encouragement as she wriggled and giggled underneath me. I kissed her when she let me and it was wonderful but she was intent on tugging on my trousers and pushing them down so she could get her hands on what was inside them.

"It's so nice to have a nice young gentleman lying on top of me instead of some middle-aged bloke who can't get it fully hard reeking of beer and fags. You certainly have no problems in that department William," she chuckled, extracting my engorged phallus from my underpants.

"We'll have to be quick. Let me get my knickers off," Felicity pushed me off her briefly to perform the task.

Watching the matronly woman hitch up her skirt and pull her lacy satin bloomers down those shapely legs adorned in her fully-fashioned black stockings was a sight to behold and my cock began to leak pre-ejaculate. I quickly kicked off my shoes and shucked out of my trousers.

When she opened her arms and legs and smiled up at me invitingly I did not hesitate and leapt on her. Her pleasingly plump body felt so different to that of Mrs Cashmore, it was comforting and exhilarating when she wrapped her arms around me pulling me close and placing sloppy kisses on my lips.

I could have lain there for hours in her warm soft embrace but I knew that we had little time before Mrs Cashmore returned. My cock sought out the fleshy folds of her sex. Her cunt was steamy and moist and my cock slid into it until it was fully enfolded by the velvety flesh of her vagina. She was not as tight as Mrs Cashmore but when she locked her legs around me and began to rise to meet my thrusts it was heavenly.

"There's a good boy now give aunty Felicity a good shagging," she chuckled and I obliged.

I kissed her red lipsticked lips and put my tongue in her fresh minty mouth and drove my cock into her moist fleshy slit delighting in the feel of her warm spongy canal clinging to my manhood as I fucked her with long slow strokes. I would have loved to have taken my time and protracted our carnal coupling but even if I wanted to I couldn't. Felicity did something with her vagina that caused it to undulate, caressing my shaft and releasing it, expressing the ejaculate from my cock in one continuous eruption.

The sensation was astonishing; both comforting and lecherous. She increased my pleasure by rubbing her stocking-swathed legs on my bottom and thighs, kissing me with her luscious lips and sensuous tongue and writhing beneath me as she squealed into my mouth at the intensity of her own orgasm. Her cloying sex became wetter and the pungent smell of her vaginal secretions and the musty stench of my semen assaulted my nostrils.

I tried to thrust in and out of her spongy maw but she held me tight as she expressed the last of my seed deep inside her. I gave up and held onto her, cherishing the satisfaction and comfort I experienced lying atop this lovely plump matron.

I felt so comforted and satisfied that I nearly fell asleep in her arms in the afterglow of our lovemaking.

"Come on luv; climb off aunty Felicity, Delores will be here any minute," Felicity lowered her legs and unwrapped her arms from around my body.

It was a timely warning as we heard the rattle of the front door being tried followed by an impatient knocking. We scrambled to get dressed, Mrs Bancroft pulling up her knickers and me stumbling around on one foot trying to get into my trousers.

Felicity held me still and wiped her lipstick off my face and brushed my hair back into place.