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.
“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.
“Finish getting dressed and I’ll go down and let her in. That should give you enough time to put that away and look decent,” she smiled at me and patted my shrinking erection.
The banging on the door got louder as Mrs Bancroft paused to freshen her lipstick. She smoothed out her skirt and skittered down the stairs to let Mrs Cashmore into the house.
“Bloody hell Felicity don’t leave me out here on the doorstep like a vagrant,” I heard Mrs Cashmore’s shrill voice, followed by the clatter of her heels in the hallway and then the stairs.
“Sorry Delores I was just putting the finishing touches to the boy’s hair,” Mrs Bancroft explained as she followed Mrs Cashmore up the stairs.
I took the hint and hopped back into the salon chair, and only just in time. Mrs Cashmore was delighted with the results and fussed about me a little, complimenting Mrs Bancroft on a job well done.
“There; I don’t know what all the fuss was about William. Your hair looks wonderful and that hairstyle suits you and will also work perfectly when I dress you as Wendy,” she said as we drove back home.
“I have to say that Mrs Bancroft is a brilliant hairdresser and I’m very happy with my new hair,” I agreed with her.
“I’ve bought you a little present but you can’t have it until I next summon you to my house,” she replied.
“And when will that be Mrs Cashmore?” I asked.
She gave me a withering stare and I knew that I had overstepped the mark.
“You know the answer to that question don’t you William?” she responded sternly.
I nodded and remained silent.
The rest of the journey was conducted in stony silence. I wondered what purchases Mrs Cashmore had made, there were a number of packages on the back seat and they intrigued me but I knew better than to ask.
As we turned into my street Mrs Cashmore pulled to the curb and broke the silence.
“Don’t play me for a pillock William; that room reeked of cunt. Get out and walk home. I’ll summon you when I need you,” Mrs Cashmore stared out the window and drummed her fingers on the steering wheel as I sheepishly alighted from the car.
To be continued