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 could afford 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 presume 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 hanging onto the 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 she was her desire was sapped 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 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 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 followed her inside, meekly following the two women.

“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 of 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

Chapter Three - Relax and Take What I Am Offering You

Three weeks of agony… that's what Mrs Cashmore put me through.

She didn’t invite me over and she refused to see me or to answer my calls. Worse, she seemed to spend more time outside than usual, deliberately teasing me; dressed provocatively and ensuring that I saw her. She knew I was watching her and she played me for it. Hotpants with pantyhose and heels! Who wears those to do the gardening? Mrs Cashmore, that’s who. Miniskirt, stockings and heels! Who wears those to hang out and bring in the washing? Mrs Cashmore, that’s who. Who wears a negligee suspenders, stockings and heels to put out the garbage bin? Mrs Cashmore, that’s who.

The stream of men visiting her house was endless and I was jealous of every one of them. She would linger in the doorway kissing the men when they arrived; letting them paw at her, knowing I was watching. I knew it was all done for me because before all this she would usher the men inside to keep the nosy neighbours from watching. But I was the nosiest of all her neighbours and she knew it.

I diligently practiced walking in the high heels she had bought me despite my solemn promise that I wouldn’t. I even bought a makeup palette and lipstick and practiced my makeup late into the night. Even though she refused to see me, she controlled me.

I stole a pair of her pantyhose and nylon boy-leg knickers from her washing line intending to masturbate with them and put them on her doorstep as an act of disobedience and rebelliousness. But instead I brushed my hair, made up my face and wore them with my heels. I put on a T-shirt so it looked like I was wearing a miniskirt and walked around my bedroom. I looked at myself in the mirror and saw a pretty teenage girl looking back. I masturbated several times a day but I never seemed to be satisfied.

When the summons finally came I vowed that wouldn’t answer it.

I was there exactly on time, meekly standing on her doorstep waiting to be let in; hoping that it wasn’t a tease and that she wouldn’t leave me out here begging to be let inside.

“You know where to go. Go and get changed Wendy,” she ordered, pointing down the corridor to the door to the cellar.

Mrs Cashmore stood steadfast and made me squeeze past her. She smelled delightful and the slinkiness of her skirt as I brushed past her felt wonderful. She was wearing her Sunday best: a tight figure-hugging navy blue suit with a short skirt moulded to her buttocks and a tight white satin blouse straining to contain her ample bosom. I glanced at her long, toned, legs sheathed in the sheerest shiny nylon and her feet shod in black four-inch pumps.

I had missed her so much and yearned to touch her. I wanted to take her in my arms and kiss her and tell her how much I adored her. But I didn’t. I obediently walked down the corridor to the door leading down into the cellar carrying my pathetic carry bag inside of which were my high heels.

I stripped naked and folded my clothes and sat down to do my makeup. I was continually amazed at the transition when I had completed this chore. Looking back at me from the mirror was not a teenage boy but a seductive, pretty girl. My new hairstyle feminised and softened my face. I slipped into the lingerie and hosiery that Mrs Cashmore had laid out for me but I noticed a new addition. There was a red satin and lace brassiere that matched the knickers I was wearing.

“One of the gifts I bought for you while you were having your hair styled by Mrs Bancroft. But it will look silly without breasts to fill the cups,” Mrs Cashmore explained.

She came over to where I was sitting and held out the garment for me to inspect.

“So I bought you these,” Mrs Cashmore handed me a shopping bag.

I put my hand in the bag and pulled out a silicone breast.

“They are called breastforms and are worn by women who have had a mastectomy or by men who crossdress. They can be attached to your chest using surgical tape or they can be glued to the skin. Today we will just sit them inside the cups,” Mrs Cashmore took the silicone breast from me.

She helped me put on the brassiere and showed me how to adjust it then she stuffed the cups with the breastforms and adjusted it again.

I looked at myself in the mirror and saw a well-endowed teenage girl looking back at me. When I put on my skirt, blouse and heels the transformation was complete. Mrs Cashmore had turned me from a skinny teenage boy into a sexy young woman.

“Now you really are Wendy,” she patted my bottom.

“What do you say?” she said sternly.

“Thank you Mrs Cashmore,” I said smartly.

I was so grateful to be in her presence once again after so long that I didn’t tell her that I was unnerved being transformed this way. Don’t get me wrong, the feel of the clothing on my skin, the taste and smell of the makeup was provocative but I also felt a sense of unease. Why did Mrs Cashmore go to such pains to transform me into a girl? Was it part of my training to be her submissive?

“Give me a turn around the room Wendy. Let’s see what you have learned,” she smiled at me and I obliged.

Three weeks of practice had netted results. I was adept at walking in the heels and I had mastered the feminine mannerisms she so wanted me to adopt. Even my speech had changed slightly and I spoke with a smoky effeminate voice which she complemented.

“I have succeeded Wendy. I have rid you of your boyish masculinity and turned you into a delightful young woman. Get used to it because this is how you are to present whenever you are here,” she gently smoothed her fingers through my hair.

If that was the price I had to pay to be in her presence then so be it, despite my unease.

“By the way. I noticed a pair of pantyhose and boy-leg knickers went missing from my clothesline Wendy and I know that you are the culprit,” her demeanour changed.

“I only took them so I could practice,” I replied sheepishly.

“Well there will be no more stealing from me. You may unwrap the rest of the packages I bought for you. There is hanging space set aside for you in the armoire and I have cleaned out a drawer for you to keep your lingerie and hosiery in. Be a good girl and pack away your presents and then join me at the cross,” she said.

I have to admit that it gave great delight to open the packages of lingerie and hosiery. There were also some skirts and blouses and she had even purchased me another pair of high heels: red with a five-inch heel and platform sole. I packed them away in the armoire as instructed and although I wasn’t particularly happy with having to present as Wendy from now on, having my own space allocated to me in Mrs Cashmore’s armoire meant that I was to become a regular visitor; why else would she do so?

I walked over to the saltire cross as instructed and awaited further instruction.

“Face the cross Wendy and assume the position,” Mrs Cashmore said as she made her way to where the whips and canes hung on the wall.

I trembled in anticipation of what was to be, my buttocks felt like they were burning already but I was also excited. My Pavlovian reflex produced an erection which painfully tented my knickers. I dropped my skirt and folded it carefully as I had been instructed to do and took up position facing the cross with my arms and legs extended.

Mrs Cashmore secured my ankles and wrists to the cross and the closeness of her body caused me to become further aroused.

The sting of the cane on my buttocks was painful as Mrs Cashmore gave me ten lashes. She stopped and pressed her body against me and put her hand between my legs and fondled my throbbing penis.

“Don’t you dare come yet Wendy,” she whispered in my ear as she teased me.

The feel of her body pressed against mine and her fingers featherlightly caressing my cock through my knickers contrasted with the throbbing pain in my buttocks and combined into a decadent feeling of satisfaction and delight.

Mrs Cashmore alternated between spanking me with her hand and lashing my behind with a whip. She fondled and caressed me after every ten strokes she applied to my panty-clad buttocks.

Mrs Cashmore stopped after a while and left me hanging on the cross. My arms and legs were aching and my bottom was burning and I hoped that she would soon be done with me and grant me release. Would she use her hand or her mouth on me? Would she let me shag her? The fantasy and expectation of what was to come made the pain tolerable; in fact the pain had become part of the ritual and was the price I paid for gratification.

She seemed to be gone an inordinate amount of time, fiddling with something she had taken from a drawer next to the bed. What new device for inflicting pain was she searching for? I turned my head but I couldn’t turn it far enough to see exactly what she was doing.

The click-clack of heels on the floor as she returned was encouraging and my cock throbbed in anticipation. When she ground her body against mine it felt wonderful. I realised that she had removed her skirt and I could feel her stocking-sheathed legs and panty-clad mound pressing against my legs and buttocks.

“Is that nice?” she taunted me.

“Yes,” I whispered.

She stood back from me a little and I heard the gurgle of the slippery lubricant she used to masturbate me as she expressed it from the tube. I shivered in anticipation.

I felt her breasts press against my back and her breath on my neck as she pressed herself against me again. She pulled my knickers down a little and took my cock in her greasy fingers. She slowly stroked it and I sighed.

Mrs Cashmore began to slowly masturbate me, her breasts pressed into my back with her hand reaching around my body so she could hold my quivering manhood. I just wished she’d press her lower body against me too so that I could feel her legs and pubis against me.

My wish was granted.

But not in the way I wanted it to be. I felt an object being pressed between my buttocks. It was coated with something slippery and it nudged my tight sphincter.

I screamed in pain as the strap-on dildo Mrs Cashmore was wearing slid inside my anus.

“Don’t be a sissy Wendy. Relax and take what I am offering you,” Mrs Cashmore nuzzled the back of my neck with her lips.

The situation was bizarre. Mrs Cashmore was pressing her body against me and the sensuality of the nylons, lace and satin that clad her body was delightful as were the soft kisses she was placing on my neck and cheeks, so was the delicious feeling of her fingers caressing my cock. The pain from my anus was excruciating however. I could feel the plastic cock buried deep inside me and my sphincter was stretched and my rectum filled.

I had stopped screaming and just hung from the cross emitting little sobs while Mrs Cashmore cooed into my ear and softly caressed my cock.

Then something amazing happened.

Mrs Cashmore began to slowly slide the strap-on dildo in and out of my behind keeping time with the soft slippery strokes of her hand on my cock. I was able to relax my anus and the cock buried inside me no longer caused the intense pain that it had when it had initially entered me. It actually began to feel quite pleasant and my sphincter tingled and deep inside me an exquisite sensuous sensation began to build.

“Good girl Wendy,” Mrs Cashmore cooed as she slowly fucked me.

“Yes. You are very good girl,” she snickered as she felt me begin to push back against the invading member assaulting my anus.

It was over quickly. The deep voluptuous feelings that I felt in my bowels built to a crescendo of highly concentrated pleasure, complemented by the sparks of delectation that radiated from my sphincter and the delightful gratification that issued from my cock, which Mrs Cashmore continued to strike.

My whole body shook and my knees gave way as the most intense orgasm I had ever experienced wracked my body, the pleasure emitted from both my anus and cock was so overwhelming that I thought I might pass out. Steaming ropes of semen shot forth from my penis and I pushed back hard against Mrs Cashmore’s plastic cock and ground my buttocks into her groin to illicit every scintilla of pleasure from the invading member.

I stood gasping, tied to the cross, only the bonds holding me onto the cross kept me upright when Mrs Cashmore finally stepped away from me.

“Lick your mess off the floor and then go and clean up Wendy,” Mrs Cashmore ordered, unstrapping the dildo from around her waist.

When she freed me from my bonds I was unable to stand and I fell to my knees and lapped up the puddles of warm semen off the floor then Mrs Cashmore handed me the instrument with which she had invaded my anus and pointed to the bathroom.

“Wash the dildo Wendy. Also you will find a douche in the bathroom. Fill it with warm soapy water and cleanse yourself. From now on it will part of your ritual. You will cleanse yourself before you come to my house, every time Wendy… every time,” she instructed.

I made my way over to the bathroom on my hands on knees, utterly degraded, my anus burned and my buttocks stung but I felt the most sexually fulfilled that I had ever felt in my life.

I pulled myself to my feet, hanging onto the sink for support. I washed the plastic cock that Mrs Cashmore had used to fuck me. I couldn’t look at it because I felt so ashamed at what had happened to me but more importantly I was appalled that I had liked it. I stripped naked and sat on the toilet using the douche as I had been directed to, then I washed myself using warm soapy water and a flannel. My cock was almost too sensitive to touch and my anus and buttocks still burned but I bore the pain to ensure I was spotlessly clean. I put my clothes back on and brushed my hair and fixed my makeup and came back out into the cellar on unsteady feet.

“You’ve been such a good girl Wendy, letting me fuck you. Now you can fuck me,” Mrs Cashmore called from where she was lying on the bed stripped down to her lingerie, hose and heels.

Any pain I felt quickly dissipated and I almost ran to the bed to fulfil my duties. It was wonderful fucking Mrs Cashmore while we were both dressed in our finery and my orgasm was almost but not quite as intense as the one experienced when she fucked me with the strap-on… but I would never admit that anyone.

When Mrs Cashmore ordered me to change back into William’s clothing and sent me home I was fully satisfied. She once again took the video cassette tape from the camera, labelled it and put it with the others. My anus ached for days after the assault but it wasn't an unpleasant ache, in fact I found it quite pleasant.

I counted the days until I was once again summoned to Mrs Cashmore’s house. It was the following Friday and I was ordered to report at 6pm. When I arrived I was delighted to find Mrs Bancroft in attendance. Mrs Bancroft gave me a cheery greeting, kissing my cheek but she looked at me a little strangely.

“How are you finding your new hairstyle William?” she asked.

“It’s wonderful Mrs Bancroft, it suits William and it suits Wendy,” I replied to her formally rather than calling her Felicity.

Mrs Cashmore was watching our interaction intently.

“Come with me Wendy, no time to dawdle here with Mrs Bancroft. We all have things to do,” she said fussily, directing me to the cellar door.

The cellar had undergone a transformation. The overhead lighting was subdued and a string of party lights hung around the walls giving the place a festive feel. The theme was continued with a table laid with finger food with a temporary bar beside it. The saltire cross was pushed against one wall beside the restraint table and another large bed had been set up in the middle of the room. Mood music drifted out of the speakers and the place exuded a party atmosphere that was bereft only the guests.

I knew better than to ask what it was all about.

Mrs Bancroft was dressed in a leather miniskirt with her stoking-tops showing. She was wearing a red satin blouse, opened to reveal her ample bosom, red high heels and her hair was styled, as one would expect, and her makeup heavy. I found my eyes drifting between her and Mrs Cashmore who was dressed similarly, only her blouse was blue and her heels black.

“Go and change Wendy. Please confirm that you performed you cleaning duties at home before you came?” I knew what she meant and yes I had douched prior to leaving home.

My mother had raged at me briefly when I told her where I was going but she was pretty much resigned to my fixation with Delores Cashmore and had given up trying to keep me away from her.

“I have a nice little surprise for you,” Mrs Cashmore led me to the armoire and reached into it.

She produced a black satin French maid’s uniform complete with white lace trim and a white satin and lace apron and matching cap.

“Black fully fashioned stockings and black heels please Wendy but you should be astute enough to know what goes with what by now,” she smoothed out the garment and handed it to me.

“Is there going to be some sort of party Mrs Cashmore?” I asked, hoping that I was going to be tended to by both women.

“Yes there is Wendy and you're invited,” she smiled sweetly at me.

“Oh thank you Mrs Cashmore,” I gushed.

“Oh you’re not invited as a guest; you’re the maid,” Mrs Cashmore said indignantly turned on her heels and left me to transform.

I came out of the ensuite half an hour later dressed in my maid’s uniform tottering on four-inch high heels. My waist was cinched by the costume which made my false breasts look bigger than they were and they pushed against the lustrous black satin of my dress. The apron was tied tightly around my waist. The dress was short as the hem rested high on my thighs displaying the welts of my black fully fashioned stockings. My makeup was heavy and hair perfect with the little white lace cap perched atop.

Another woman had arrived, dressed identical to Mrs Cashmore and Mrs Bancroft except her blouse was mauve.

“Come over and meet Mrs Blundell,” Mrs Cashmore instructed.

Mrs Blundell was younger than the other two women, in her mid-twenties I suspected, and she had long blonde hair. She too was not pretty in the true sense of the word but her looks were unique and alluring.

“Don’t gawp!” Mrs Cashmore said harshly to me.

“So this is your pet project? This is the Wendy you’ve told me so much about,” Mrs Blundell said looking me up and down.

“Yes. What do you think?” Mrs Cashmore replied.

“You’ve done a good job on her. She should fit in nicely,” Mrs Blundell responded to Mrs Cashmore, which caused me further unease.

“What does she mean Mrs Cashmore?” I asked.

Mrs Cashmore ignored my questions.

“I host these soirees occasionally Wendy. Mrs Bancroft, Mrs Blundell and I will entertain some of our gentlemen friends. Your task will be to ensure that they looked after,” Mrs Cashmore explained.

“Walk around the room. Pass out canapés and finger-food, take drink orders and fill them. Clean as you go, pick up the plates, empty the ashtrays and so on. You’re astute enough to understand what duties a maid is required to perform,” she looked down her nose at me.

“Do not stare! Whatever happens in this room tonight stays in this room. Keep your eyes averted, mind your manners and attend to your duties and you will do fine. There may or may not be a reward for you at the end of the evening,” she whispered that last sentence into my ear and squeezed by buttocks firmly.

Not long after that a gaggle of men descended the steps down into the cellar. They all seemed to be middle-aged and were well dressed. There appeared to be eight of them but it was hard to tell as the group dissipated immediately and began to engage with the three women.

I had already poured champagne into flutes and put them on a tray and I walked amongst the men and women offering them the champagne and taking orders from those who wanted something else to drink. I went back to the bar and poured drinks and delivered them. Some of the men smiled at me and whispered crude comments to the women they were speaking to.

The men were very forward and lewd with the women and openly fondled them and spoke to them quite lasciviously. I tried to ignore the goings on and took around trays of canapés and more drinks. I cleaned up as I went as I had been directed to do.

After a short period the men began to disrobe. Some stripped down to their underwear and some stripped naked. As I had been ordered to do, I tried not to stare but I was becoming very excited. Undoubtedly there was about to be an orgy and I would be able to watch it.

One of the men took Mrs Blundell over to the four poster bed and they began to engage in sex while another man stood by watching and waiting his turn.

The remainder took Mrs Cashmore and Mrs Bancroft to the new bed and most began to engage in group sex with both women while one or two stood by watching until they replaced those who had sated themselves. That was how the evening progressed and I was kept busy providing food and drinks and cleaning up. Once the initial frenzy of debauchery died down the men and women took a break to reconstitute, sitting around drinking, smoking and talking. Some of the men left the party and I showed them to the front door. Now and then one of the remaining men would single out one of the women and take her over to one of the beds to have sex.

It is hard to imagine but after observing the frenzied debauchery and consequential coupling, watching the sex actually became boring and besides I was kept busy.

A few of the men made half-hearted passes at me but it was mostly just teasing and Mrs Cashmore directed the men away from me and they were more than happy to have their needs attended to by any one of the erotically presented women who were there specifically to tend to their needs. I was later to discover that the men had paid a premium to attend the party and expected to get full value for money.

In the early hours of the morning most of the attendees were drunk and just lazed around smoking and talking. One of the men took Mrs Cashmore aside and they had an in-depth discussion turning my way and gesturing. Mrs Cashmore nodded to the gentleman and then she came over to speak to me.

“Mr Smith, not his real name but it will serve the purpose for now, has offered me quite a lot of money to spend some time with you,” Mrs Cashmore explained.

I blanched and felt faint.

“You’ve got to be joking! I’m not doing anything more than carrying out my maid duties,” I replied angrily.

“Oh Wendy. You silly girl,” she laughed in my face.

“You will do whatever I tell you to do,” she said calmly.

“Hey everyone! Who wants to watch some home movies?” Mrs Cashmore shouted out to the remaining revellers.

Two prostitutes and four remaining men all enthusiastically replied that they would be delighted to do so.

Mrs Cashmore turned on the large-screen TV and put a tape in the VCR and took the remote. The tape was a composite spliced together from video that Mrs Cashmore, unbeknownst to me, had filmed during my visits to the basement. It was a tell-all tale that was degrading and explosive. There was footage of me being whipped and beaten, being transformed from a teenage boy to a teenage girl, begging for release, squealing while I was being punished and most incriminating, an extended scene of me dressed as a young woman, tied to the saltire cross being buggered by Mrs Cashmore.

This final scene was greeted by raucous applause.

I was cajoled and teased by the men and women as they dressed and got ready to leave. I busied myself cleaning up around them feeling embarrassed and utterly degraded. I burned with indignity and I intended to tell Mrs Cashmore that she had gone too far and that I would no longer be heeding her summonses.

Mrs Blundell and Mrs Bancroft changed into more appropriate attire and left. Mrs Bancroft came over and gave me an affectionate hug and told me not to worry about the video.

“It’s not like anyone in this audience can talk about it. All those men are married professionals whose lives would be ruined if anyone knew about their secret peccadilloes,” she explained.

The other men left too with the exception of the man who Mrs Cashmore had referred to as Mr Smith. He and Mrs Cashmore were once again involved in a heated exchange. Mrs Cashmore appeared to cede to whatever Mr Smith had proposed.

“Come over here Wendy,” she said to me quite tersely.

I didn’t want to. With all my heart and soul I didn’t want to surrender to Mrs Cashmore’s authority. I knew that nothing good was going to come of it. I had already decided that I would no longer remain under her spell.

I went over as ordered.

She was standing next to the restraint table which had been pushed against the wall. She told me to extend my wrists into the restraints which I could only do by bending over the table. With all my consciousness I refused to obey.

I bent over the table and put my wrists in the restraints.

Mrs Cashmore locked my wrists into the handcuff-like devices and I shivered with dread. She walked behind me and pulled my knickers down around my ankles.

“I’ll leave you two lovebirds to it. Enjoy yourself Mr Smith, you can pay me on the way out,” she said and I heard her footsteps receding up the stairs and the finality of the sound of the cellar door closing.

I was alone with Mr Smith, who was still naked and standing behind me. Bound to the table, bent over it with my knickers down, I felt vulnerable and was shivering with fear.

I felt Mr Smith position himself behind me and I winced in anticipation of the extreme pain and humiliation that he was about to inflict on me.

He lifted my dress up and I tensed with dread.

Then I felt my satin panties sliding up my stocking-clad legs and being pulled snuggly into place. Mr Smith came around to my side and unclasped the restraints and helped me to my feet.

He turned me to face him, his face only inches from mine. He wasn’t handsome but he had a pleasant face. His hair was thinning and he was a little pudgy but he looked at me with kindness and compassion. He brushed a stray lock of hair from my face.

“Not this way. I don’t want you this way,” he whispered.

“You are beautiful. Exquisite. You are to be slowly savoured not swiftly ravaged,” he said.

This was the first time that anyone had been kind to me whilst I inhabited Wendy’s persona. I could see the genuine affection and yes, to be honest, lust in his eyes. I felt special, I felt beautiful, I felt desired… I felt feminine.

When he pulled me closer and kissed me I melted in his arms. I wrapped my arms around him and pressed my body against him. The feel of the satin French maid’s uniform was sensual against my skin, especially where it grazed my knickers and stockings.

His lips were full and sensual and as much as I thought I would be repulsed by kissing a man the opposite was true. It felt delightful and it made me feel a little powerful knowing that this man found me attractive. I opened my lips a little when he offered his tongue and when he explored my mouth I felt myself becoming tumescent and I could feel his lips form a smile and so did mine.

I could feel his cock poking me in the belly and then he began to rub it on my white satin apron. I instructively wrapped the slinky apron around his turgid member and began to stroke it. He gasped and thrust his hand between our bodies and lifted my skirt and began to stroke my cock through my satin knickers and it was my turn to gasp.

Any inkling that I had that it was William in the basement dissipated at that moment; there was only Wendy. I became Wendy. I thought like Wendy, I felt like Wendy, I lusted like Wendy. I wanted Mr Smith to make me feel like a real woman.

I allowed him to guide me over to the bed where we broke our embrace. I started to undress but Mr Smith stopped me. He unbuttoned my bodice and put his hands in my bra and ripped out the breastforms.

“We don’t need those silly things,” he whispered as he buttoned up my bodice.

“I want you just like are. I’ve always had a fantasy about French maids and also about special ladies like yourself and now I get to experience them both in the same package so to speak,” he stroked my arms.

Then he pushed me and I fell back on the bed and he leapt on the bed and lay beside me, smiling at me. I stroked his face and he took my fingers and kissed them.

“You are exquisite,” he sighed and rolled on top of me and began to kiss me.

“There are so many things that I want to do to you and that I want you to do to me but its late so let’s enjoy the little time we have together to its fullest,” he whispered between kisses.

His hands were everywhere, stroking my legs, stroking my face, stroking my cock through my knickers and I reciprocated and took him in my hand. His cock felt meaty and powerful and not at all disgusting. I loved the feel of it, the latent power of it, the turgidity of it. I wanted to put it in my mouth and suckle it but Mr Smith had other ideas.

He forced my legs open and lifted them high and lay between them. He fumbled on the bedside table and then I felt him ease the crotch of my panties aside and a cool soothing gel being applied my sphincter and then I felt his glans pressing where his fingers had been.

“Are you ready?” he looked down at me lovingly.

I nodded and I put my hands around his neck and pulled his face to mine so that he was kissing me when he entered me.

He did so slowly and carefully, responding to my little winces of pain and sighs of pleasure. I relaxed my sphincter and made it easier for both of us as he pushed his manhood into me, one little infinitesimal fragment at a time. It hurt at first and I felt unbelievably full and stretched and then I felt unbelievable pleasure and I wrapped my silken-sheathed legs around his torso and impaled myself on him.

“There. Now fuck me Mr Smith,” I smiled up at him.

“I’d be delighted to Wendy,” he grinned down at me.

He lowered his face to mine and kissed me passionately as he began to slowly fuck me. The pleasure receptors in my sphincter and my prostate were super-energised and the feeling of his big cock filling my anus was euphoric. This was no rubber dildo but a real flesh and blood penis inside me and it made me feel simultaneously submissive and dominant.

I squirmed beneath Mr Smith and gasped between open-mouthed sloppy kisses as he held me down and vigorously fucked me, slamming his cock in and out of my anus as my heels and fingernails raked his back to encourage him. My whole body was electrified with the rapturous sensuality of it. I felt like a young woman. I felt like a slut. I loved it!

Mr Smith’s belly was rubbing on my cock still trapped inside my satin panties and I think that was the final provocation; the breaking point if you will, that tipped me over and triggered my orgasm.

I clung to Mr Smith and kissed him fervidly as I lifted my buttocks off the bed so that every scintilla of his turgid throbbing manhood was buried inside me. I felt his release. He groaned into my open mouth as his cock shuddered inside my anal sheath and flooded me with his scalding seed. I filled my panties with my sperm and rubbed against him to increase my pleasure.

We pawed at each other, kissed each other, ground against each other, we fucked each other, until we were both spent and satiated.

Mr Smith lay on top of me panting and gasping. He was heavy and I could feel his heart pounding. His erection began to diminish and his cock plopped out of my tight anus followed by a trickle of semen. My body was soaked with his sweat, my knickers were sodden with my semen, my lips were swollen from his kisses and my anus throbbed dully.

I had never felt so happy in my life.

Once he had his breathing under control Mr Smith lifted himself off me. I expected him to climb off the bed and leave me now that he had used me; I knew that he was in a hurry. But he didn’t. He lay beside me, kissing me affectionately and telling me how wonderful and beautiful I was. But I was right. It was very late and he had to go.

I lay on the bed and watched him dress. He bought me over a drink a cigarette and sat on the bed to put on his shoes and socks.

“You are wonderful Wendy. That’s what I’m going to call you… Wonderful Wendy,” he smiled down at me.

He smoothed my hair and kissed my forehead and rummaged in his inside pocket.

“I hope to see you again soon. Keep this. Don’t give it to Delores,” he dropped a fifty pound note on the bed and walked to the stairs.

I put down my drink and cigarette on the bedside table and lay on my back holding the fifty pound note up in front of my face.

I heard the clatter of Mrs Cashmore’s heels on the stairs and then on the floor as she approached.

“What do you have there Wendy? Who let you out of the restraints?” she said sharply.

I lowered the note and looked up at her.

Her face screwed up with anger.

“Get off the bed and clean this place up! Clean yourself up!” she screamed at me.

“Fuck that, I’m too tired. I’ll see you later this evening,” I gingerly lifted myself off the bed.

Mrs Cashmore stood there like a statute, incredulous that I had spoken to her that way.

I didn’t bother changing. I walked next door still dressed as Wendy. It was three in the morning and I doubted very much that mother would be awake to see me.

Too bad if she was.

To be continued

I slept in late. I was supposed to work at the hardware store but I was too tired and besides, I just didn’t want to. My mother pounded on the door but I refused to get out of bed and we had huge fight through the closed door.

She berated me for staying out all night at Mrs Cashmore’s and told that I was just like my father was before he finally left her: lazy and besotted with the whore next door. If I didn’t want to contribute to the household and abide by her rules, I wasn’t welcome under her roof.

The comment about my father being besotted with the whore next door piqued my interest but I was just too tired to argue any longer.

When I finally arose I realised that I had been so tired last night that I had not removed my makeup and had gone to bed wearing my panties, bra and stockings. The French maid’s uniform lay crumpled in the corner. Late in the afternoon I took a shower and returned to my room. My bottom was a little sore but the pain was pleasant rather than unpleasant. My cock began to harden as I recalled my adventures with Mr Smith and I was tempted to take care of my burgeoning erection but I resisted the temptation.

I had no intention of dressing as William. In fact William seemed to have abandoned my psyche, the only presence I felt was Wendy. I took out my meagre supply of makeup and did my face and brushed my hair. The lingerie and the French maid’s uniform were soaked with sweat and drying semen and quite frankly they reeked. I put on the pantyhose and boy-leg knickers that I had stolen from Mrs Cashmore’s clothes line, they would do for now.

I put on a large t-shirt and wore it as a makeshift shift-dress and then put on my high heels. I put the French maid’s uniform and the lingerie I had worn to the party into a pillowcase and took them with me.

“My god! What has that woman done to you?” my mother called after me as I walked out the front door.

I ignored her and sauntered next door to Mrs Cashmore’s house, uninvited and ready to face her ire. I pushed the doorbell and held my head high when Mrs Cashmore answered the door. I walked past her without saying a word. Mrs Cashmore seemed both bemused and amused at my behaviour.

“I need to change and I need to use your washing machine,” I said as I made my way inside.

“By all means Wendy. Join me in the lounge room when you’re ready,” Mrs Cashmore.

I made my way the little laundry and put my washing in a lingerie bag and tossed it in the washing machine along with some of Mrs Cashmore’s underwear. I set the machine to ‘delicates’ and turned it on. Then I went down to the armoire in the cellar and changed into a skirt and blouse and made my way up to the lounge room.

Mrs Cashmore was also dressed in a skirt and blouse, pantyhose and heels and sat smoking and sipping tea on the couch. Her flaming red hair was perfect; straight, shoulder length with a fringe, her makeup was heavy and exotic, as was her perfume. I was taken with her as usual but her spell over me was nowhere near as strong as it had been.

“You took quite a risk coming around here dressed as Wendy,” Mrs Cashmore said, pouring me a cup of tea.

I sat down beside her smoothing my skirt under me and took the preferred cup of tea.

“I really no longer care what other people think of me. I have no time for William at the moment I’m afraid,” I replied quite dispassionately.

“Besides which, you made it quite clear to me that I was to present as Wendy whenever I am in your home,” I continued.

“We need to discuss what happened last night,” Mrs Cashmore offered me a cigarette which I took.

“Well the way I recall it you made me wait on you and your guests while you hosted a sex party. Then you humiliated and degraded me by showing that video.”

“I’ve thought about it and decided that it really doesn’t matter. The people you showed it to were there participating in an orgy with three prostitutes and are unlikely to tell anyone what they saw.”

“Then you made a deal with Mr Smith. You basically sold me to him for his sexual gratification but it backfired on you really. Rather than ravishing me while I was bound to the table he took me to the bed and made love to me,” I crushed out my cigarette with some finality.

“Really? He made love to you?” Mrs Cashmore looked amused.

“Please don’t interrupt me Delores,” I persisted, deliberately using her first name.

“My hypothesis is that you have made it your mission to subjugate me… to make me your chattel. You knew I was infatuated with you and you used that fact to your advantage. Then you feminised me. At first I thought it was just another way for you to degrade and control me; but I have since decided you did it for other reasons,” I said.

“Other reasons? And what are they?” Mrs Cashmore was nonplussed.

“Let me ask you a question or two Delores,” I said, amused by her ire when I used her first name again.

“You obviously have an extensive client list and I think that Mrs Bancroft and Mrs Blundell are associated with you. They too are prostitutes but you seem to be the boss or the director if you like.”

“I’m guessing that amongst your extensive clientele there will be some men who have a penchant for special ladies like me. It’s obvious that some of them are into S&M, otherwise why the dungeon?” I stipulated.

“Is there a question there Wendy?” Mrs Cashmore was becoming impatient.

“Did you feminise me and make me your chattel so that you could sell me to your clients?” I asked her directly.

“Well at first you amused me Wendy. Once I had total control over you I wondered if it would be possible for you to submit to being feminised and when you gladly submitted, then I thought well why not?” she answered.

“Now let me ask you a question. You obviously liked it when I fucked you with the strap-on. Did you like it when Mr Smith fucked you last night?” she arose and traipsed over to the bar and began to pour drinks.

“No I didn’t like it… I loved it,” I replied and Mrs Cashmore burst out laughing.

“So you did like it?” Mrs Cashmore offered me a gin and tonic which I took.

“Why don’t we cut to the chase Delores? I have a proposal for you,” I countered.

“I find myself in a dilemma. I enjoy being Wendy far more than I like being William. I’d like to spend all of my time as Wendy but that is impossible.”

“My mother saw me this morning so she knows. She’s about to throw me out so I need somewhere to live and I want to live as Wendy. So why don’t I live here? You can prostitute me out and garnish my wages and by that I mean the money I earn as a prostitute,” I sipped my drink and watched her over the rim of my glass.

“Oh you silly girl,” Mrs Cashmore sniggered.

“Not really. You have a spare room. You work from home so I can too. I’ll also be your housekeeper so you will make money from selling me and also have someone to do all your chores,” I countered.

“Why not give it a trial period? Let me stay here for a month under the conditions I stipulated. If it works out I stay and if not I move out,” I proposed.

“An intriguing proposal Wendy. What is your mother going to say?” she asked.

“I'm an adult. I can do what I like,” I replied.

“And your job at the hardware store?” she raised her eyebrows.

“Mr Smith gave me fifty quid last night. I don’t know how much a prostitute makes but I bet I will make more than enough to live on. I will be quite a novelty. A young pretty transvestite who likes sex; I bet I will be a welcome addition to your stable,” I said.

“My stable? Oh you're such a hoot Wendy,” Mrs Cashmore sipped her drink.

“Mrs Bancroft and Mrs Blundell,” I retorted.

“Felicity and Amanda work for themselves but yes they are associated with me. I have an extensive client list and send men their way and I also organise monthly sex parties for which they pay me a stipend,” she mused.

“Well it would be the same with me, except you would also have a live-in housekeeper,” I responded.

“Ok. Let’s try it out. We’ll give it a go for one month,” Mrs Cashmore finally agreed to my proposal.

“Wonderful!” I beamed and clapped my hands.

“Two more things. Is it ok if I call you Delores?” I asked.

“Of course Wendy; except when I restrain or discipline you,” she smiled back.

“What's the second?” she asked blithely.

“My Dad. Mother said he was infatuated with you,” I said.

Delores Cashmore laughed.

“Your father was weak willed and besotted with me, does that sound familiar? He knew what I was doing. I was a lot younger then and he spent as much time here as he could afford. I told him that he was spending too much money on me but he couldn’t get enough and I wasn’t going to let him fuck me for free,” Delores explained.

“Eventually he went broke and your mother threw him out in the street. She couldn’t take the humiliation of his constant infidelity and he was spending every penny he made on a prostitute so he was of no use to her. It’s that simple.”

I never knew why my father left home. I knew that his breakup with my mother was far from amicable, I remember the fighting and the shouting. Mother never told me why he left but now I knew. Now I also knew why my mother detested Mrs Cashmore.

That very afternoon I went home and took what I wanted from my old room and boxed up the rest and put it away in the cellar. To my relief my mother was out so we did not have a confrontation. I cleaned my bedroom and changed the linen. When I finally closed the door on my old room it was cold and sterile with nothing of William remaining.

I took my meagre belongings next door and Mrs Cashmore led me to her second bedroom which was now mine. I went down to the armoire and bought up most of my femme clothing and some makeup. I did what little I could to instil Wendy’s personality on my new room. There was nothing left of William except for some legal documents.

I went down to the laundry and hung out the French maid’s uniform and the other clothing I had washed on the clothes line. I saw the curtain twitch next door and briefly saw my mother’s face and then she dashed the curtains closed.

“I have two of my best clients coming this evening Wendy. I have explained to them my changed circumstances and they are intrigued. We will entertain them together so go and prepare yourself,” Delores said when I had finished my household chores.

I douched, showered, put on my makeup and dressed as Delores had insisted. She had loaned me a black satin bustier from which draped long red garters. She told me not worry about putting in the breastforms, from now on they wouldn’t be needed when I working. I knew immediately what she meant by working.

I put on the bustier and Delores tightened it, cinching it around my waist so that I had an hourglass figure. I slipped on my long, black fully fashioned stockings using the techniques that Mrs Cashmore had taught me and finally a pair of red satin full-cut knickers. I stepped into my four-inch black heels and followed her to her bedroom.

“We’ll buy you some jewellery using an advance on your wages but for now I’ll lend you a few pieces,” she said standing next to her vanity table and spraying me liberally with exotic perfume.

She put a silver necklace around my neck, matching silver bracelets on my wrists, and silver drop earrings in my ears. I’d had my ears pierced since I was fourteen.

“There. Now you look the part,” she led me over to the full-length mirror so I could see the results.

“They’re going to love you,” Delores whispered in my ear.

Mrs Cashmore was wearing her black leather catsuit with five-inch high heels and severe makeup. We actually both looked the part.

The closeness of her body, the scent of her perfume, her breath in my ear, the sound of her sultry voice caused me to become tumescent. Mrs Cashmore had told me not to tuck or gaff and my cock distended the front of my knickers.

“Be a good girl and wait for us in the dungeon,” Mrs Cashmore squeezed my swollen member briefly and patted me on the buttocks to send me on my way.

I waited patiently down in the cellar. Mood music was playing from the speakers and the lighting was softened. I noticed that the video camera was set up in the corner so that it had a field of view covering the whole cellar which had been rearranged back to its normal configuration after the party.

At exactly eight o’clock I poured four drinks as instructed and just as I had finished I heard the clack of high heels on the stairs and sound of men’s voices.

“Wendy, this is Steven and Anthony,” Mrs Cashmore introduced the two men to me as I handed out drinks.

“Steven, Anthony, this is Wendy, the little project I told you about,” Mrs Cashmore beamed.

“Delightful,” Anthony beamed and stroked my face.

“You’ve done a good job on her Delores. Give her a pair of tits and gaff that and she’d pass anywhere,” Steven roughly grabbed my penis.

“What’s the rules with her?” Steven circled me, looking me over carefully.

“No visible marks on the exposed parts of her body, other than that anything goes; she’s been well trained,” Mrs Cashmore replied.

“Fucking and that?” the man put his hand inside the back of my panties and roughly inserted a finger in my rectum.

“Same rules. Anything goes. She hasn’t been used much so she will still be tight,” Mrs Cashmore sipped her drink while Steven prodded and poked at me.

“I bags her then,” Steven spanked me on the bottom, marking his territory.

“And you Anthony?” Mrs Cashmore asked the other man.

“I’d like what we both agreed to and paid for but I’m happy for Steven to take Wendy first while I play with you. Then we swap over,” Steven seemed nonplussed.

“Then its agreed gentlemen, four hours premium service with the two of us swapping partners at half time. No visible marks to be left on the exposed body parts of anyone. The safeword is Red as usual. Shall we get started?” Mrs Cashmore pointed over to armoire.

The men disrobed and hung their clothes on the two valet clothes-stands and donned the black satin robes provided. Both men had been wearing expensive suits and exuded wealth and privilege, although all men are equal when naked. Anthony was tall, tanned, muscular and handsome if you liked men with Neapolitan features.

Steven was short, pasty-faced, pudgy and pale. His face was set in permanent scowl. He seemed like the kind of man who had grown up on the streets and acquired wealth the hard way. His language was coarse as was his demeanour. He was a man used to getting whatever he wanted.

I wondered how much these men were paying Delores for our company and what my share might be.

“Come over here luv,” Steven said.

He was standing next to the saltire cross his robe open over his expansive hairy belly, his penis poked out from under it; short, turgid and nasty looking. Not that I cared, this was to be my permanent employment from now and I had no say as to the presentation or appearance of the punters. Delores had explained to me that all that mattered was that they were clean, disease free, abided by the safeword and could pay.

“Give us bit of this then,” Steven pulled me to him roughly and kissed me.

He shoved his tongue into my mouth and worked it while his hands tweaked my nipples. At least his breath was fresh, his paunch prevented him from rubbing his cock on me so he guided my hand there. I took his small thick cock in my hand and began to stroke it. I returned his kisses and put my free hand around his shoulders to keep balance and hold myself close to him.

As much as the man might have looked repulsive, he gave off an essence of power and masculinity that I found intoxicating. I became tumescent myself and my penis pressed against his bulging belly through my knickers.

“You are the young and pretty one aren’t you but I don’t want to touch that,” he tried to push my penis away from his body but it sprang back.

“Let’s get you on the cross then and then I can have a go at that arse,” he grunted as he squeezed my buttocks roughly.

I stepped up to the cross, faced it and assumed the position: legs spread, arms high and wide, pressed against the X-shaped wooden frame. He had a little difficulty securing my wrists because he was so short and I giggled a little as he fumbled with the manacles.

I would learn never to laugh at a punter again.

“Did you think that was funny?” he barked in my ear once he had me secured.

“I’m sorry sir,” I replied as Mrs Cashmore had directed me to.

“You will be,” he growled, cruelly squeezing my buttocks.

He went over to the wall to select his corporal instruments and I was able to look in the mirrored wall and see that Delores had Anthony lying face down, strapped to the vinyl table and was applying a flail to his back none too gently. Anthony’s body tensed at each blow and he grimaced but he asked for more.

I screamed as a cane came down hard on my buttocks and felt the searing pain spread from the point of impact. Mrs Cashmore stopped whipping Anthony and looked over at me. I nodded to her that I was ok.

Tears filled my eyes and my heavy mascara began to run as Steven laid ten lashes into my buttocks. The intensity of the pain was such that I couldn’t do or think of anything to ignore it. The suffering and agony consumed me as the cane ripped into my buttocks, tormenting me as I writhed on the cross.

Then Steven stopped and I sagged against my bonds. My buttocks burned and slowly the pain began to dissipate until it became a throbbing ache… a throbbing ache that I found delightfully addictive. When Steven pressed himself against me and turned my face so he could kiss me I willingly accepted his kisses. My cock was rampant and leaking pre-cum into my knickers.

“What was that Wendy?” Steven pulled my hair, forcing my face close his.

“More please sir,” I whispered.

He sniggered and untangled his fingers from my hair. I sensed him walk away and tried to see what instrument of torture he was selecting.

I soon found out as the thong and fall of a leather whip snapped into my lower back. Had I not been wearing the bustier it might have drew blood. I tried to stifle a scream but I couldn’t. Steven grinned and lashed me again. This time the pain was far more intensified but the lashes weren’t as localised and concentrated like they were when he caned my bottom. Steven spread the lashes across my upper and lower back.

Each stroke was like a strand of fire, like small lava flows spreading across my torso. I was close to using the safeword when Steven stopped. He was bent over, his hands on his knees, panting with exertion.

I was in so much pain that I couldn’t speak. I hung from my bonds, my wrists burning my buttocks throbbing with a dull ache and my torso a sea of fire.

“Are you ok?” Delores appeared beside me.

I opened my eyes and saw that Anthony had been freed from his bonds and was waiting patiently for her at the restraint table. His erection stood out proudly from his toned body.

“I’m fine. Go tend to Anthony,” I smiled grimly at her.

“Be careful Steven,” Delores growled at my tormentor.

“She knows the safeword. Fuck off and suck some dick you trollop,” Steven snarled.

I nodded at Delores to indicate that I was alright and she stepped away from me.

“Ok Wendy. Enough of that. Let’s see how tight you really are,” Steven stepped in behind me.

He had a tube of lubricant that he pressed into the crevice of my buttocks. I only wished that he had a salve instead and would smear it on my throbbing bottom and burning back.

He could only get my knickers down to my thighs but that was all that was needed. Steven pressed his body against me and with some difficulty finally positioned his cock against my sphincter. He held my hips and pushed himself inside me.

I gasped but it wasn’t with pain it was with pleasure. Once again the burning pain in my body comingled and amplified the pleasure radiating from my sphincter and anus as Steven fucked me. The tip of his glans only just reached my prostate and not every stroke found its mark but the feel of his thick cock stretching my anus and the irregular provocation of his cock on my prostate gland induced a state of wantonness in me.

I pushed out my buttocks to encourage him and his belly rested on the small of my back permitting him to get everything inside me. I could see in the mirror that Anthony had Delores bent over the restraint bench and had opened the crotch of her catsuit and was fucking her vigorously which she seemed to be enjoying immensely.

“There’s a good girl,” Steven laughed and spanked my buttocks.

“Now let’s get to fuckin’” he chuckled.

He took hold of my hips and began to fuck me slowly at first and then built up the tempo as his pleasure intensified, as did mine. I pushed my buttocks out to meet his thrusts and gyrated them when he was fully inside me to maximise both our enjoyment.

“Oh, you are a good girl,” he sighed and plunged his stubby weapon all the way inside me and ejaculated.

I could feel his cock convulse and a river of semen expel from his engorged cock and I pressed back against him as hard as I could and ground against him as I also climaxed.
My semen spattered on the rubber matting and I groaned with lust. Steven held me tightly by the hips and mashed his groin into my buttocks as he spent himself inside me. He made a few insistent thrusts and then pulled out abruptly.

I felt his spunk dribble from my dilated sphincter and run down my thighs and soak into my nylons. He must have been carrying a considerable load because his issue continued to flow from me as he stood back admiring his work.

“Did you come you dirty bitch?” he bellowed when he saw the puddle of semen under the cross.

I could only nod. I was recovering from the beating and an intense orgasm and was trying to catch my breath.

“You dirty tranny whore!” Steven bellowed.

He picked up the cane and began to thrash my bare buttocks. The pain was unbearable and I began to scream.

“Red! Red! Red!” I shrieked.

Steven didn’t stop flailing me with the cane; in fact he hit me harder.

“Let’s see you giggle now you tranny cunt! You still think that it’s funny that I had difficulty lashing you to the cross?” he gasped as he continued to cane me.

He suddenly stopped and I saw that Anthony had dragged Steven away from me and was holding him at arm’s length, trying to settle him down.

“Not kosher Steven! You’ve been warned about this before. We have a safeword for a reason and you bloody-well know the rules,” Delores berated him while she unshackled me from the cross.

I refused to fall to my knees when I was freed from my bonds. Instead I pulled up my knickers and walked with as much dignity as possible to the bathroom. I found the salve and dropped my drawers and began to apply the soothing balm to my burning buttocks.

“Here, let me help you with that,” Anthony was wearing his black satin robe and he took the tube of lotion from me and applied it to the areas I couldn’t get to.

“May I?” he tugged gently at the laces of my bustier.

I nodded and he unlaced the corset and let it drop away from my torso.

“Jesus,” he whispered when he saw the red lashes across my upper and lower back.

“Steven is a bastard sometimes,” Anthony said as he gently applied more of the slave to my body.

The burning pain dissipated just like a raging storm at sea as it crosses over an isolated pinnacle.

“Thanks Anthony. Can you retie by bustier and then I’ll fix my makeup and join you all for drinks,” I said with as much decorum as I could muster.

Anthony retied my bustier and turned me around so that I was facing him. He looked down affectionately at me and gently stroked my cheek.

“Leave the makeup. I like the way your mascara is all smeared and smoky; it’s sexy. Just freshen your lipstick. Don’t forget I’m next if you are still up for it,” he smiled at me and lowered his face to mine.

He kissed me softly and I melted in his arms and fell against him. I could feel him turgid penis through his robe and to my amazement I also became engorged. I felt him smile through the kiss.

He gently disengaged from me and ran his fingers through my hair.

“Take as long as you need then come join us Wendy. I’m looking forward to it,” he smiled at me, turned and left the bathroom.

I brushed my hair and reapplied my lipstick, leaving my eye makeup smudged as Anthony had requested.

I re-joined the others who were sitting on the sofas nursing drinks and smoking. Delores was showing them the video of me that she had shown the others at the party. Steven was particularly taken with any scenes that involved me being punished or humiliated. I came to the conclusion that the man had a sadistic streak that he that he openly displayed, as if he was proud of it.

“Come on Delores I’m ready to go again. I didn’t pay good money to sit around smoking and drinking with a prossie slag and a tranny,” his robe was open and his stubby erection was poking out from under his belly.

Steven smacked Delores viciously on the bottom, half dragging her over to the cross.

“That man is no gentleman. He’s a sadistic boar and a cretin,” Anthony patted the seat beside him and I sat down gingerly.

“Are you still hurting?” he asked, looking at me with genuine compassion.

“It’s more a dull ache at the moment,” I replied.

“I'm surprised that Delores allows that arsehole to use her services after the all trouble he has caused her but I suppose the money is too good to refuse. Besides, I doubt she has any choice in the matter,” Anthony handed me a gin and tonic which I gratefully sipped.

“What do you mean by she has no choice in the matter?” I asked, reaching for a cigarette.

Anthony beat me to the cigarettes and took one and lit it for me. He studied me closely before he spoke.

“How old are you Wendy?” he asked.

“I’m nearly nineteen,” I replied.

“So young. So naïve,” he sighed.

“Steven Cottrell controls most of London’s illicit gambling and protection rackets. He runs it all through a legitimate security company but he has a reputation for being ruthless. He fosters that reputation. He’s a vicious bully and a real villain. If you’ll excuse my French he’s a right cunt.”

“You’re a bit young to know all this of course but at one time he was in the newspapers at least once a week but over the last few years he’s stayed away from the limelight and lets his lieutenants do the dirty work,” Anthony explained.

“So?” I asked, a little puzzled.

“So, you can bet Steven pays Delores a premium and provides her with protection. Other than Delores do you know how many Madames there are in London who operate their own businesses that aren’t controlled by organised crime? This many,” he answered his own question by holding up his fingers formed into a circle.

“She’s the only one I know of. He pays her a premium because even though everyone knows Steven Cottrell is a cunt, they don’t know about his predilection for sexual sadism or his liking for young men and transvestites and Delores keeps his secrets” Anthony paused to take a drink.

“How do you know all this?” I asked, intrigued.

“Because I’m the villain that controls everything that Steven doesn’t control. He takes the lion’s share and I take what’s left over. I’m happy with that arrangement, I make more than enough money and because we cooperate and mind our P’s and Q’s we don’t get any grief from the Old Bill,” Anthony explained.

“So on my very first day working officially for Delores Cashmore I’m to be shagged by the two of the biggest villains in London?” I gave him a mischievous smile.

“Just one Wendy. After what Steven has put you through I don’t intend to shag you,” Anthony smiled at me and finished his drink.

“What if told you I was disappointed?” I slipped my hand inside his robe.

“As you witnessed, if anything I’m a sub but I suppose the best way to describe me is versatile and as much as I’d dearly like to shag you Wendy, I don’t want to cause you any more pain,” he guided my hand to his long sleek erection.

“But that doesn’t mean I’m not going to insist that you satisfy me in other ways,” he leaned into me and kissed me.

I kissed him back and softly stroked his hard cock. He pulled me into his lap and kissed me a little more insistently and I could feel his penis pressing on my bruised bottom. I put my arms around him and snuggled up to him, relishing the feel of his hard body against mine. We kissed and caressed and I eased his cock from under me so I could stroke it lazily.

We could both hear Delores’ muffled cries as Steven laid into her with the lash but she never used the safeword so we ignored it and concentrated on pleasing each other.

Anthony surprised me when he began to stroke my cock through my knickers. The featherlight touch of his fingers through my satin panties felt almost comforting. I drove my tongue into his mouth and our kisses became more insistent.

“Be a good girl Wendy,” he whispered and eased me down onto the floor between his knees.

I fell to my knees and gazed at his long thick manhood standing proud, the glans glistening with precum.

I lowered my face to it and took it into my mouth. This was the first time I had performed fellatio and it was not the demeaning repulsive task I thought it would be. I again felt that sense of power as Anthony sighed and languished on the sofa, allowing me to suckle on his phallus.

It tasted lovely, the pre-ejaculate was quite sweet and the feel of his cock between my lips, the meatiness of it and the pulsing veins, was quite exciting and stimulating. My own cock was throbbing in my knickers. I soon learnt to use my lips on his shaft and my tongue on his glans, slowly bobbing up and down on the hard flesh, feeling it pulse and quiver whenever I fluttered my tongue on his fraenulum.

Anthony began to lift his groin insistently and he gently held my head and expressed to that he wanted me to go faster and suck harder and I was happy to comply. My head bobbed up and down in his groin as I suckled his member which was pulsing rhythmically indicating that he was not far away from climax.

“Can I come in your mouth?” he gasped, his orgasm imminent.

Without taking my face away from his cock I nodded my consent and found my own cock with my hand and began to stroke it.

Anthony let out a guttural passionate moan as he filled my mouth with his hot creamy issue. It spewed from his glans in a series of pulsing rhythmic spurts. It tasted musky and salty and absolutely delightful. I expressed my own seed into my knickers and a pleasant if not tumultuous wave of pleasure emanated from my shuddering penis.

Anthony held my head still and thrust his cock in and out of my mouth as I slavered at his phallus, sucking the last of his issue from the pulsing appendage. I swallowed every drop and was very content to do so.

Anthony surprised me when he lifted me back into his lap and held me close and kissed me tenderly. I thought that having just ejaculated into my mouth he would find it revolting but the opposite was true. His tongue seemed to investigate my mouth thoroughly, searching for any vestiges of his spend.

He rearranged my body so that I was sitting sideways in his lap, my legs stretch out on the sofa. I put my arm around him and rested my head on his shoulder feeling utterly content. He searched out my lips and kissed me softly as we both reposed and recovered from our climaxes.

Over his shoulder I could see that Steven had Delores lying on her back on the restraint lounge with her legs over his shoulder as he jackhammered his cock in and out of her. Delores face was strained with either lust or distress or possibly a mixture of the two. Steven cried out and pulled Delores hard against him as he emptied his semen into her.

I looked away and brought my face to Anthony’s so that I could kiss him; I had no interest in watching Steven defile Mrs Cashmore.

The two men were well satisfied and had a couple more drinks before they left. Anthony kept me cuddled up to him and we kissed and fondled each other lazily whilst Steven and Delores sat on the sofa across from us where they too kissed and petted. Steven seemed to delight in pinching or tweaking Delores in her delicate places, causing her to wince which obviously amused him.

When the evening came to a close we saw the two men to the door and said our farewells. We went to our respective bathrooms and showered and changed into negligees and fresh knickers. We met in the lounge room where Delores had a large tube of slave in her possession. We applied the soothing lotion to each other’s bodies where Steven had whipped and caned us.

“Is it always like that?” I asked.

“It depends. I specialise in B&D and S&M so it’s to be expected, but not as hard as you were treated tonight. I’m afraid when Steven Cottrell is present things always get taken to the extreme,” Mrs Cashmore sighed.

She surprised me when she came over to me and kissed me softly on the forehead.

“You did well today Wendy, I’m proud of you. Now let’s go to bed its late,” she whispered.

I followed her upstairs but when I turned towards my bedroom she took my hand and led me to her room. She turned out the lights and we snuggled up in bed and fell asleep spooning, content just to be in each other’s company.

To be continued

Chapter Five – Can I Get A Passport?

After four weeks of being confined in Mrs Cashmore’s house I desperately wanted to go out, the furthest I had been was the back garden to hang out the washing and assist with the gardening. Delores did the shopping on Saturday and went to church every Sunday. I quizzed her about that but her response was vague. She said that she had been bought up a Christian and despite her chosen profession she still practiced her faith on Sundays.

Most days of the week we entertained gentlemen callers. At first, most of them wanted the services offered by Mrs Cashmore but as the word got around about the young pretty transvestite living with Delores I started to become popular. Sometimes we would entertain gentlemen together down in the cellar and sometimes we would entertain them individually. Some of the punters wanted to engage in B&D or S&M but surprisingly most did not, they just wanted sex.

I became accustomed to providing sexual services daily and was jealous of Delores when my services were not required. Delores continued to feminise me, working on my gait, posture, mannerisms and voice and I was a willing pupil. For all intents and purposes William Baxter had disappeared. When I wasn’t tending to the needs of customers or practicing my femininity I kept house for Mrs Cashmore sometimes joining her to tend to the garden.

My mother saw me outside in the garden on a number of occasions and I wondered how she felt about my chosen lifestyle and also wondered what she had told our acquaintances, which were admittedly few. Not that I cared. I was already wondering if it was possible for me transform from a man to woman. Mrs Cashmore had a personal computer which she used to manage her business and she also had a dialup modem. I found a few fledgling internet websites dealing with transgender issues but there was little information available about how to actually transition. It didn’t help that transsexualism, as it was termed at the time, was still considered a mental illness in the UK in the year 2000.

I openly discussed the possibility with Delores who was sympathetic to my cause but advised me to take baby steps.

“There are quite a few transvestites getting around quite openly Wendy and some are so feminine that they are seldom clocked. You know what that term means right?” she asked me.

“Yes and that would suit me just fine,” I replied.

“Then we need to get you out and about and build your confidence. I can honestly say that you are very passable. The first thing we need to do is get you a suitable wardrobe. Dressing provocatively will attract undue attention,” she explained.

“But before that we need to discuss finances. I intend to take half of what you earn. I think that is fair as it not only covers my stipend as your Madame but includes your room and board. I’m prepared to right off the money that I already spent on your clothes and makeup but you will need to become self-sufficient,” she continued.

“Wait! Does that mean that that I can stay? That the trail period is over?” I asked eagerly.

“You are performing your duties to very satisfactory standard Wendy and I find you have a tolerable disposition. I quite like your company,” Mrs Cashmore smiled at me.

I hugged her and kissed her enthusiastically until she peeled me off of her. Our relationship had changed significantly since I began to live with her. I still worshipped her and we sometimes had sex if we had a night without having to tend to punters but we had also become sisterly. I was still her pet project and she delighted in teaching me the nuances of femininity and she still occasionally disciplined me but we were companions and confidantes who lived and worked together.

“These are your monthly earnings after expenses,” Mrs Cashmore laid out nearly two thousand pounds in cash on the table.

“Oh my god Mrs Cashmore, really!” I was stunned.

“You’re averaging two to three punters a day Wendy. So over the last month you’ve earned a pretty penny. Our services don’t come cheap,” she picked up and fanned the bills.

“I take it you have a bank account in William’s name that you can still use?” she asked.

“And a credit card,” I replied.

“You will have to keep using that until we can establish Wendy Baxter’s legal identity. Nothing you have in your wardrobe is really suitable for street wear. A matron like myself getting around in a business suit is de rigueur but a teenage girl dressed like that will attract attention. Let’s see what I have in my wardrobe that might be suitable,” Delores said.

“Time to go shopping Wendy,” Delores smiled at my enthusiasm.

Driving to Brent Cross shopping centre I was both apprehensive and excited. I was apprehensive because it was my first foray into the world in my femme persona and I was terrified that I was going to be clocked and ridiculed and I was excited because… well it was my first foray into the world in my femme persona.

Delores found a pair of black leggings and black long sleeve chiffon side-buttoned office blouse with a mandarin collar. It was stylish but not ostentatious and I wore the leggings and blouse with a pair of red three-inch high heels that Delores had bought for me as my other heels were outrageously high for everyday wear. She toned down my makeup and with my brown shoulder-length hair with the balayaged highlights I looked attractive without appearing trampy.

I was experienced at retracting my testes into my inguinal canals and tucking my penis under my perineum. I held the tuck in place by wearing a pair sheer to the waist pantyhose under my leggings and went sans panties so that there was no VPL on display. There was no tell-tale bulge in my crotch area just a smooth V. With my breastforms in the cups of my bra I had an almost perfect figure.

“The boys are going to go bonkers for you Wendy,” Delores teased.

“I don’t want them to go bonkers for me, I want them to leave me alone until I become less self-conscious,” I replied.

“Besides, they are just as likely to go bonkers for you Delores,” Mrs Cashmore was wearing her usual livery: a charcoal grey suit with a tight pencil skirt that rested three inches above her knees, white satin blouse, black heels, and shimmering tan hosiery.

Her makeup and hair were perfect and she was wearing her signature red lipstick.

“Nonsense! We’ll look like mother and daughter,” she smiled at me.

“I’ll keep an eye on you. Stay close and behave as normally as you can. You are beautiful and passable; nothing bad is going to happen, I want you to enjoy yourself,” she reached over and took my hand in hers and squeezed it affectionately.

My heart was in my mouth when we turned off Prince Charles Drive into the multi-story parking garage and got out of her BMW. It wasn’t too bad initially because there were few people in the car park and those that were there were coming and going to their vehicles taking little interest in two women out for a day’s shopping.

All that changed when we entered the open well-lit space of the shopping centre. I immediately felt that all eyes were on me and I clung to Mrs Cashmore for moral support.

“Be cool calm and confident Wendy. Look around carefully and you will see that hardly anyone is looking at you and the few that are, are giving you an admiring glance. People are here to shop not to play ‘clock the tranny’,” she made me halt at a bench near a set of escalators and allowed me to gather my wits.

My confidence built slowly as we made our way from shop to shop and my attention was diverted from the people around me to the wonderful goods on display. We concentrated our efforts on Fenwick, John Lewis and Marks & Spencer and I immersed myself in the shopping experience and thoroughly enjoyed selecting clothing, lingerie, hosiery, footwear, makeup and accessories.

Delores accompanied me to the fitting rooms when I needed to try on various items but I soon felt confident. At first I was very nervous interacting with the staff but I soon realised that their only interest in me was trying to sell me their products. I think one of the more mature shop assistants might have suspected that I was trans but she politely said nothing.

After spending a considerable amount of my stipend and making three trips to and from the BMW I was done. I had a complete wardrobe.

“When we get home I want you to move all of your fetish clothing down to the cellar and leave your daywear in your bedroom,” Wendy said as we sat sipping coffee in a food court.

“I need to go,” I whispered.

“To go where?” Delores frowned at me.

“I need a wee,” I iterated, crossing my legs in discomfort.

“Well go you silly girl,” Delores said patting my hand.

“Time for the butterfly to fly on her own,” she smiled and nodded at the sign for the toilets.

My nervousness returned as I approached the ladies loo. This would be my first time using a ladies convenience and I was very self-conscious. I knew that I needn’t be. I had not been clocked all day except perhaps by one shop assistant who had got up close and personal taking my measurements for a suit.

I set my resolve and opened the door to the loo. There were three young teenage girls hanging around the back corner near the vanities illegally smoking cigarettes.

“What are you looking at you stuck up bint,” a girl with frizzy blue and orange streaked blonde hair wearing black tights, pink hoody and hi-top trainers snarled.

She wore heavy dark eye makeup and pink lipstick and was smacking gum between dragging on her cigarette. Her friends were similarly dressed and they all exuded teenage angst disapproval and rebellion.

I ignored them and went into the closest cubicle and locked the door. My need to pee far exceeded my fear of any teen outrage and indignation. We were in a high-end shopping centre and the girls were hardly a street gang.

I pulled down my leggings and pantyhose and bunched them around my ankles and sat on the toilet. My penis dropped down and I sighed with relief as I unleashed a steady stream of urine into the bowl. I had been sitting down to pee ever since I had decided to live full-time as Wendy so it was not unnatural for me. When I finished I wiped and stood up to tuck, pulling up and smoothing out my pantyhose.

As I leaned down to smooth out my leggings I heard a snigger above my head.

“Hey girls, she’s a tranny,” the rainbow-haired girl was standing on the toilet in the adjacent cubicle peering over the top of the partition.

I opened the door to the cubicle and the other two girls were standing against the bank of sinks opposite looking menacingly at me.

“Excuse me, I need to wash my hands,” I said not making eye contact.

The rainbow haired girl kicked open the door to the cubicle in which she had been spying on me and joined her colleagues, preventing me from approaching the sinks.

“You fucking freak. You shouldn’t be in here you fucking perv,” she snarled.

“I’m just using the facilities and now I’d like to wash my hands and leave,” I replied indignantly.

“You’re a fucking bloke dressed as a woman, you shouldn’t be in here,” one of the other girls retorted.

I decided that the best course of action was to leave the lavatory and wash my hands somewhere else but the girls formed a phalanx in front of me preventing me from leaving.

“You're a fucking nonce and we don’t like nonces do we girls?” the teenage witch looked at me, her rage evident in her stance and on her face.

“You know what we do with pervs with you? We kick their fucking arses don’t we girls?” she looked at her two compatriots for support and they nodded their agreement.

“Are those tits even real?” one of the girls pointed at my chest.

The girls must have been fifteen or sixteen at the most and I could easily take them on individually but with them fighting as a pack I was about to be overwhelmed.

“Ok you bitches, come and kick my arse but at least one of you going to get seriously hurt,” I prepared for the assault.

The girls looked at each other a little unsure if they should proceed but the rainbow-haired witch gritted her teeth and leapt at me. I lashed out with my three-inch heels and caught the rainbow warrior right in the crotch and she came to an abrupt stop and curled up on the tiled floor holding her hands to her cunt.

I knew that a kick pleat is an inverted pleat used at the base of a narrow skirt to allow the wearer more freedom of movement. But it was the first time I ever saw it used to actually allow someone wearing a tight pencil skirt to kick someone which was exactly what Mrs Cashmore did as she came through the door to the lavatory. She kicked one of the teenage girls so hard in the arse that she went sliding across the tiled floor and joined her rainbow-haired friend.

“Would you like a bit of slap and tickle too luv?” Delores glared at the remaining girl who was trembling in her boots.

She scooted past Mrs Cashmore and ran out into the shopping centre.

“Let’s go Wendy, I think we’re done here,” she smiled at me.

I smiled back at her and made to leave.

“Wash your hands first, there’s a good girl,” she admonished me.

I washed my hands looking at the two sorry looking teenage girls curled on the floor, one nursing her twat the other her arse.

“I’m telling my brother!” rainbow whined petulantly.

“Tell him. I’ve probably got a bigger dick than him anyway,” I retorted and left the lavatory to join Delores who was retrieving the last of our shopping bags and parcels from the shopping centre help desk.

We made it all the way to her BMW before we both cracked up. We hugged each other as tears of laughter ran down our cheeks and then the laughing stopped and we kissed.

“Shouldn’t be allowed!” an old crone remarked as she walked past dragging along her two grandchildren who were both staring at us open mouthed.

That remark cracked us up again and we howled with laughter and clung to each other.

At that moment in time I was never more in love with Delores Cashmore.

We both had customers that evening and I was grateful that the man who wanted my company did not want any bondage and discipline play; he just wanted to spend an hour with me.

He was a nice married man in his fifties and Delores explained that the man’s wife was frigid and he’d developed a thing for transsexual and transvestite women. The fact that I was so young had emboldened him to hand over nearly the equivalent of a week’s wages to Delores so that he could spend some time with me.

Delores was entertaining one of her trusted regulars and she took him up to her bedroom allowing me and my punter to use the four-poster in the cellar dungeon.

“Would you like a drink?” I said to the man who was visibly shaking with excitement.

I was wearing a red leather miniskirt, a white satin blouse, tan nylon stockings and the same red heels I had worn to the shopping centre earlier in the day. My makeup was heavy and I was doused in perfume.

The man was speechless when Delores introduced him to me; all he could do was stare at me so I took his hand and I led him down to the cellar.

“I’m Barry,” the man offered me his hand.

“Oh come on Barry, give a girl a kiss,” I sidled up to him and pressed by body against him and kissed him.

He was not a very good kisser, all open mouth and sloppy tongue but I let him kiss and grope me. His hands went straight to my skirt and he squeezed me quite hard and then he hiked up my skirt and groped my knicker-clad buttocks and silken-sheathed thighs.

“I wish Gladys would wear stockings for me. I just wish Gladys would let me touch her,” the man mouthed around squooshy kisses.

Gladys was obviously Barry’s wife.

Barry was getting overexcited and I managed to untangle myself from his grasp.

“Let me get us both a drink Barry. We’ve got plenty of time and you don’t want to come in your trousers do you?” I turned my back on him and was about to pour us drinks when he sidled up to me.

“I’m sorry Wendy. I’ve never been with anyone as young and as pretty as you and I can’t keep my hands off you,” he sighed.

“Maybe I should let you have a quick one and then you can recover and take your time with me,” I turned and smiled at him.

“Would you luv? I think I’m going to cream my jockeys just looking at you,” he gave me a pathetic smile.

“Oh course you can Barry. You know what they say? The customer is always right,” I smiled at him and closed the gap between us.

I let him kiss me, his tongue seemed too big for my mouth, it was wet and fleshy and he moved it around inside me like a snail retracting into its shell. His lips were thin, damp and unyielding and he pressed them to mine, urgently sucking and lapping at me as he held me in a vice-like grip.

I knew that it was just excitement, inexperience and awkwardness on his part and I did not judge him harshly for it. Delores had trained me well. I was here to please the men who paid for my company and it was my job to make sure that they had the best experience possible.

I was wearing tight, white, full-cut translucent knickers and Barry had my skirt up again and was pawing at my buttocks, holding me close against him. I put my arms around him and returned his kisses as best I could, I could feel the heat and hardness of his manhood pressing against me, his need for release was almost palpable.

I was able to slide a hand between our bodies and unzip his flies and free his erection. Gladys, whoever she was, was missing out on a rather useful penis. Barry might be older and clumsy but his cock was a magnificent specimen. Long thick and smooth, it throbbed in my fingers.

I guided it between my legs and closed them tight so that the meaty weapon was clamped between my stocking-tops. I rocked back and forth as Barry began to fuck my legs and my diaphanous nylon-clad thighs massaged his engorged cock. He gasped into my mouth and pulled me even tighter as I felt his cock quiver and palpitate and then his scalding semen spattered down the back of my legs soaking into my stockings.

“Oh god, I’m sorry,” he began to cry.

“It’s fine Barry. I like it. It means that you find me really attractive and sexy if I can elicit such a tremendous response like that from you so quickly,” I clung to him and kissed his neck softly.

He held on to me, sobbing quietly, his semen cooling on my legs. I whispered endearments into his ear and placed soft kisses on his cheeks and his mouth until he calmed down. Eventually he issued a huge sigh of contentment and I disengaged from him. I cleaned my legs with some tissues.

“I’m sorry,” he had his head down like a chastened schoolboy.

I lifted his chin and kissed him quickly.

“Did you enjoy it?” I asked.

Barry nodded his head bashfully.

“Then all is well in the world Barry. Let me fix us a drink and we can go and sit down if you like,” I smiled at him and he grinned back at me and nodded.

He self-consciously tucked his trunk-like appendage into his underpants and zipped up his trousers and took the drink I offered him. We adjourned to the couch and I deliberately sat close to him so that our thighs were touching.

“So Barry, do you like special girls like me specifically?” I asked, stroking his forearm.

“Yes I do but there aren’t that many of you. When I was a young man I used to go to Chelmsford and see a girl called Charlie who worked under the railway overpass but she moved on. She was a victim of the Chelmsford Slasher but that was way before your time,” Barry sighed.

“It’s risky picking girls up off the street so I save up my money and when I have enough I come here to see Delores. When she told me that she had taken you in and that you were available I raided the bank account and booked a night with you. Gladys is going to be pissed when she finds the money missing but you are worth it,” he smiled at me cheekily.

“I’m glad that you like me Barry, I like you too,” I snuggled up to his stocky body and nuzzled him under the neck.

I knew that Barry was fascinated with me so why not indulge him? I kissed him and when he tried to return the kiss with a sloppy open-mouth, thin-lipped smack I stopped him.

“Like this Barry. There’s no need to be so impatient, I’m not going anywhere,” I straddled him with a knee either side of his thigh.

He was naked and his cock was at attention and rubbing on my knickers.

I softly placed my lips on his and opened my mouth just a little.

“Now you do it,” I whispered and he let his lips soften and opened his mouth partially.

I kissed him again and he duplicated my actions. When I put the tip of tongue into his mouth he did the same to me. When I kissed him a little harder, he did the same. He had stopped slobbering and trying to force his tongue down my throat, I had taught him how to kiss… and he liked it.

He put his arms around me and kissed me, bobbing me up and down in his lap. He slid his cock in the crevice between my buttocks and rubbed it on my gossamer-thin knickers. I became engorged myself and my cock distended the front of my knickers and rubbed on his belly.

Barry was getting excited again, thrusting against my bottom so I put a hand down there and slid the gusset of my knickers aside and guided his cock to the entrance of my anus which I had pre-lubricated. Barry stopped thrusting when his glans nestled in my sphincter. I smiled at him and he smiled back as I slowly lowered myself onto his long, thick hard cock.

“Mugh,” I grunted when it was fully inside me.

It was in me so deep that it threatened to enter my bowel.

“Am I hurting you?” Barry said, concern evident on his face.

“No. It’s lovely Barry,” I smiled down at him and then lowered my face and kissed him deeply.

I began to ride his cock, letting it come almost all of the way out of me and then slowly impaling myself on it until it was buried to the hilt inside me. I wriggled my bottom to stimulate my prostate and then set about generating a slow and steady pace even though Barry was becoming insistent.

I kissed him passionately but refused to increase the pace of our lovemaking. I really liked having his engorged manhood inside me. I stroked his face and wiggled my buttocks while I kissed and fucked him. I could feel his cock fully bloated, pulsing inside me. It felt so wonderful that I was tempted fuck him hard and fast but I resisted the temptation until we were both close to extremis.

I drove my knickered buttocks into his lap and kissed him hard and fervently, writhing on his cock, evoking his climax and he held me tight as he spent himself deep inside me. I contracted my anal muscles and milked him of his semen and I felt his warm seed flood my back passage.

I filled my panties with my own ejaculate as I orgasmed with him.

We clung to each other and writhed and wriggled and kissed and fucked until I fell against him exhausted and panting.

“That was nice Wendy,” he patted my back affectionately.

It turned out that Gladys was missing out on more than just Barry’s long thick cock. He had quite the libido to go with it. After recovering quickly he took me over to the big bed and lay me on my back and fucked me long and hard. I was quite relieved when he finally climaxed because my anus was getting sore.

After a break for cigarettes and drinks he wanted to go again but I just didn’t have it in me so I fellated him on the sofa and swallowed a healthy dose of creamy cum. He really liked me using my mouth on him because guess what? Gladys didn’t do that either.

When I saw Barry to the door it was way past the allotted time he had paid for but I didn’t mind because he was such a kind sweet man. He wanted to give me a tip but I refused.

“You’re just a softy Wendy,” Mrs Cashmore teased me after I had showered and changed into my babydoll pyjamas.

We were snuggled up on the lounge watching late-night TV.

“I’m an astute businesswoman Delores. He’ll definitely be back because I looked after him so well,” I replied.

I was lying on the couch with my face was on Delores thigh and she was stroking my hair.

“I suppose so but I hope he hasn’t put that derriere of yours out of action, you have three customers tomorrow,” she caressed my cheek with her long elegant finger.

“I’ll survive,” I stifled a yawn.

“Too bad you're tired, your face is right where I want it to be, my punter got me close a couple of times but didn’t quite get me over before he came,” she smiled down at me.

I got to my knees and opened Delores’ gown. I could make out the coral pink slit of her vulva through the transparent knickers she was wearing. Her scent drifted to my nostrils and I followed it. Delores opened her legs wide and gasped when I put my tongue on her. I lapped at her vulva through her knickers and was rewarded with the decadent tang of vaginal secretions as she became instantly wet.

I eased aside the gusset of her knickers and continued to lick her outer lips, teasing her and making her shudder. Delores tried to push my face into her sex but I resisted. I made her wait, licking and nipping at her labia majora until I opened the fleshy flaps and found her soft delicate coral-pink inner lips. I circled my tongue around them deliberately keeping away from her clitoris.

Delores was panting and had opened her legs as wide as possible and was pushing my face into her crotch.

“Come on Wendy, please… go there… do it… oh god!” she screamed and ensnared her fingers in my hair when my tongue lashed her clitoral hood.

I used my tongue in a gentle back and forth motion then small circular movements directly on her clitoris ensuring that I engaged the clitoral hood knowing it would drive her wild and Mrs Cashmore groaned with contentment. Her vagina secreted more aromatic fluid which I gratefully lapped up then went back to work on her clitoris.

Mrs Cashmore was writhing on the couch, her fingers entwined in my hair, pushing my face into vulva. I slid two fingers inside her vagina and found her G-spot and stimulated it as I licked and sucked her clitoris.

This had the desired result and Delores moaned like a slattern as her orgasm erupted. She held my face to her sex and I lapped at her clitoris and massaged her G-spot until it became too sensitive for her and she tore my face away from her pubis and lay back panting on the sofa.

“Come here,” she whispered and smiled at me when she regained her composure.

I snuggled up to her and kissed her. She could taste her own secretions on my mouth which she explored with her tongue so she could lap up every vestige of her juices.

“You’re a good girl Wendy. I’ve trained you well,” she sighed.

We snuggled on the sofa until we were too sleepy to stay awake, then we trundled off to our respective beds. It was going to be another busy day and we both needed rest.

I settled into a steady routine performing household chores for Mrs Cashmore during the day, keeping the dungeon clean, the bar stocked and tending to punters in the evenings. William's psyche had totally disappeared and I seldom thought of him except when necessary such as when accessing his bank account which I had seconded. Although my mother lived next door I seldom saw her and she made no attempt to contact me. She was ashamed of me and I suppose she had a right to be.

It wasn't so much that I was living my life as a trans woman, although that would have been enough for her disown me, it was because I was prostituting myself and living with the woman she hated more than anyone in the world.

As my bank account swelled I gave more thought as to how I might continue my transformation. I knew that to be eligible for hormone therapy or reassignment surgery or any form of support I would have to undergo months or possibly years of therapy. It was not that long ago that gender dysphoria was still considered a psychological or psychiatric disorder and there were plenty in the medical profession who still felt that way.

Because I had come late to recognising that I wanted to live as a woman I doubted I would be an acceptable candidate, particularly as I had not presented any gender dysphoria prior to turning eighteen. I also suspected that when I told my story about how my need to transition had come about and how I was supporting myself through prostitution I would not be accepted as suitable for assisted gender reassignment.

The other issue I battled with was that I had no inclination to fully transition. I just wanted a feminine body inclusive of breasts but I did not want to change my genitalia. I wanted to live as a transsexual, transgender woman… whatever label suited. I didn’t care what others called me. To me I was just Wendy who was a special girl who attracted men who liked special women like me… and there were plenty of them.

Delores Cashmore’s client base had swelled significantly when word of my existence spread. Punters who had a penchant for me told friends they knew who that liked the same thing. I still provided B&D and S&M services but most of the punters who came to see me simply wanted to spend time with a young pretty trans girl.

I knew that Mrs Cashmore trusted me fully when she showed me how to manage her booking services. She had a small office set up in a space under the stairs that wasn’t much bigger than a closet. Both of us could just squeeze in. Bookings were still mainly made over the phone and she had an answering machine set up on a separate landline and also had dialup internet.

Most of the clients demanded secrecy and that’s what made Mrs Cashmore, her two cohorts Felicity Bancroft, Amanda Blundell and myself attractive to the punters. Mrs Cashmore manned her business phone from one o’clock to three o’clock in the afternoon on weekdays and Saturdays or clients could leave messages on the answering machine outside of these times. She also had an email address and had Windows 2000 installed on her PC.

Punters could ask for specific services from specific women or just specify what their kink was and when they would like the service provided. Mrs Cashmore ran a spreadsheet in Excel and assigned punters to each of us. She advertised special events such as the orgy she ran once a month.

She would pass punters onto Mrs Bancroft and Mrs Blundell who worked from their own homes and also had their own smaller client lists.

It was a complicated system but it worked. We were all making good money and the clients usually got the services they requested when they wanted them. Mrs Cashmore of course was making the most money, taking a cut from each of us but for that she ran the booking service and paid protection to Steven Cottrell who passed a percentage onto his contacts in the Metropolitan Police’s Clubs and Vice Unit to keep them at bay.

I was still wary when I was out on my own but my confidence grew with each foray I made out into the wider world. My main concern was that I didn’t have any credentials in Wendy’s name so in event I was asked to provide any form of ID I only had that of William Baxter. I used my credit card in cash vending machines and paid for everything in cash.

“Can I get a passport?” I asked Delores after I had been living with her for nearly a year.

“You mean a forgery? A good forgery?” she looked up from the Daily Mail and studied me.

“I want to go overseas and get breast implant surgery,” I replied.

I had been taking black market female hormones and my body had changed somewhat. I hardly had to shave any longer, my thighs, hips and buttocks were bigger and my face was more feminine but my budding breasts had stopped at an ‘A-cup’ and all my research indicated that they would likely not get any bigger. It was a balancing act because if I upped my hormone dose I would lose my ability to maintain an erection which I still wanted to be able to do and so did most of my clients.

“You’re impatient Wendy but I can understand your frustration,” she put down her paper and patted the sofa beside her.

“I’ll be up front with you, I have only one contact that I trust who could get you a passport that will pass scrutiny,” she said and looked at me gravely.

“Steven Cottrell,” I sighed.

“Exactly and I know he is not your favourite person,” she sympathised.

I’d been requested to service Steven Cottrell a number of times and each time he had treated me brutally. I had become accustomed to being restrained and spanked, whipped and caned and provided it was done within the bounds set by Delores I usually enjoyed it. But Steven Cottrell was savage. He liked to punish me until I used the safeword and then take me roughly.

He paid a premium but if possible I preferred not to have to service him.

“Can you negotiate on my behalf? I really want proper breasts, other than that I’m happy with my body. I bet the punters will like it too if I have a decent pair of tits,” I countered.

“We’ve had these conversations in depth Wendy and I know that you want to progress your transformation but I think you should really go and see a psychologist or at least talk to your mother,” Delores took my hand and held it.

She saw the storm begin to build on my face.

“Alright, alright, I’ll see what I can do for you but I hope you don’t live to regret it,” she relented.

“Thank you Delores,” I kissed her on the mouth.

“Ok, go about your chores and join me in the office at one o’clock,” she kissed me back and sent me on my way.

*****

John Benstead was still running his forgery and counterfeit business even though his transgender wife Candy Pops earned a good wage working in a managerial position for Goldwing Airlines where she had started out as hostess back in the 1970s. Candy had also worked as a drug mule for London gangster Tony Carlotta when she was working as a hostess on Goldwing’s premier Skyliner service to and from Singapore.

John Benstead had been Tony Carlotta’s counterfeiter and when Tony Carlotta had died Steven Cottrell had moved in and taken over Tony’s criminal organisation. Now in his sixties and near retirement, John Benstead usually didn’t do mundane counterfeiting or forgery work. He had a small team who he had personally trained who did it on his behalf passing on a percentage of the profits to Steven Cottrell.

His business still operated out of the dodgy dilapidated building in a back street of Moulsham near Chelmsford. It was the perfect front for a fraudster and forger to ply his trade.

As I made my way down the dark alley strewn with abandoned shopping trolleys, junk food wrappers, empty beer cans and bottles, cigarette butts and condom wrappers I shuddered. I was taken aback when I passed a doorway where a fat, middle-aged prostitute wearing a cheap vinyl miniskirt, faux leopardskin blouse and laddered fishnet stockings was being shagged against the wall by a man in a business suit.

I deliberately looked away and continued down the alley until I came to an innocuous looking door with peeling blue paint. The door was actually solid steel and almost impenetrable. I knocked on the door and it opened just enough for me to enter; before me stood a man of indiscernible age but probably in his sixties. His handsome face had had some work done and he was still lean, fit and tanned and he was wearing tight jeans and a Transvixen t-shirt circa 1975.

“What is it about me that I seem to attract girls of your type?” he smiled, the smoke from the cigarette dangling from his lips curling up around his eyes.

“What’s that?” I was bemused by the ultra-modern interior of the building that contrasted completely with its shabby exterior.

There were long tables with gleaming machines, myriad cameras of various types set on tripods or mounted over document tables. There were copiers and printers and reams of paper everywhere.

“I met my Missus, Candace or Candy as she prefers right here in this workshop where I made her first passport before she legally changed her gender and got a kosher one. I made a passport for Valerie Swindon who ran a finishing school right down the road in Chelmsford and believe it or not I made one for Michelle Murphy formally known as Cherri Pops, the lead guitarist of Transvixen. Michelle actually introduced me to Candy,” John grinned at me and put out his cigarette in an overflowing ashtray.

“All before your time dear but if you Ask Jeeves you’ll find them all,” his smile widened.

“Don’t forget Charlie Ringwald, the only survivor of the Essex Slasher, I’ve done my homework,” I smiled back at him.

“So, Steven Cottrell told me I was to handle this as a personal favour for him,” John became serious.

“How’s a nice young girl like you got herself involved with that sadistic cunt?” John opened a drawer and took out some paperwork.

“Does it matter?” I replied.

“Not really. Mister Cottrell is the boss and whatever he wants he gets,” John laid out a number of passport stencils on the table.

“You can go and stand over there next to the wall where that canvass is hanging,” John instructed me.

I put down my bag and stood with my back to the canvass. I was wearing a short-skirted navy blue business suit, black high heels and tan pantyhose. I’d had my hair styled and paid particular attention to my makeup for the passport photo.

My youthful good looks, curvaceous figure and long shapely legs were not lost on John Benstead who ogled me through the camera lens.

“You’re too young and pretty to be a brass but I can’t figure out what other connection you might have to Steve Cottrell,” John said as he fiddled with the camera.

“Delores Cashmore warned me about you,” I replied, nonplussed by John’s probing.

“That explains it then. You’re one of Delores’ brasses. I never knew that she’d branched out into girls of your type or I might have availed myself of her services,” John lifted his head and smiled at me.

“And what about your wife Candy? What would she think of you using Mrs Cashmore’s services?” I replied satirically.

John burst out laughing.

“The missus would likely want to tag along. We’re both getting long in the tooth but we still like a bit of variety in our sex life,” John grinned.

“Just take the photographs please Mister Benstead,” I huffed.

John shrugged his shoulders and took the pictures. When he finished he offered me a drink.

“I’m driving Mrs Cashmore’s car and I don’t have a licence in my name so if I get pulled over I’m a goner,” I replied, turning down my mouth.

“That’s all right luv, I’ll make you a driver’s licence too,” John smiled back.

“It’s a piece of piss and I can do that for you now if you’d like to wait,” John patted an overstuffed lounge chair.

I considered my options and realised that I should have asked for the licence as well as the passport.

“Can you do me a birth certificate too?” I asked.

“Now you’re pushing it,” John smiled at me.

I ignored the lounge chair and sidled up to John Benstead.

“I can make it worth your while,” I whispered and nibbled his earlobe.

“I bet you can,” John grinned at me.

He fiddled with some paperwork and then had me sign a specimen signature on the blank driver’s licence. It was the first time that I had actually signed my name as Wendy Baxter and I was thrilled to do it. I gave him another signature for the passport.

He put the document into machine and a few seconds later a plasticised driving licence with my picture and signature on it emerged. John walked over and showed it to me.

“Lovely,” I said excitedly.

John snatched it away from me when I reached for it. He hid it behind his back and I rubbed up against him playfully and attempted to retrieve it.

John pulled me against him and kissed me and I responded. I returned his kisses and reached for the bulge in his jeans. John gasped when I unzipped him and dropped to my knees.

I took his phallus into my mouth and suckled it, running my tongue along the shaft and tickling his fraenulum with the tip of it. Then I swallowed his cock and began to suck on it earnestly.

“Oh god that’s great luv,” John guided my head up and down on his shaft.

“Only thing is I’m gonna come I don’t want to yet,” he gently pushed my face out of his groin.

“Well I'm in a rush luv so you better take what you want right now,” I leaned over the back of the chair and dropped my knickers.

John moved in behind me and lifted my skirt out of the way and pulled my pantyhose below my buttocks and slid his cock inside me.

“Oh my, that’s quite a big one,” I beamed.

John took hold of my hips and began to fuck me slowly, driving himself all the way inside me, feeling me contract and relax my anus around his throbbing cock as I had learned how to do.

“For a young girl you know a few tricks,” John gasped and fucked me a little faster.

I reached under my skirt and freed my penis from my pantyhose began to stroke it in time with John’s thrusts. As John fucked me harder and faster I masturbated myself harder and faster.

“Oh jeez I’m gonna cum!” John cried and pulled my soft white buttocks had against him and ejaculated deep in my anus.

I wriggled my bottom appreciatively and pushed back against him and ejaculated onto the floor taking care to keep my skirt out of the way.

John’s cock remained buried in my anus and he turned my head and kissed me until his erection began to subside and then it fell out of my puckered sphincter. John reached for some tissues and gave them to me so I could wipe up. I adjusted my nylons, pulled up my knickers and straightened my skirt.

“Mrs Cashmore was right about you,” I smiled at him, dropping my new driver’s licence into my purse.

“You can pick up the passport and birth certificate next week,” John said, leading me to the door.

I kissed him goodbye and made my way back up the narrow alley to the main street where I had parked Mrs Cashmore’s BMW. The brass in the doorway was on her knees fellating another punter.

To be continued

Author's note: I notice this story is not popular and has received very few reviews. Some of my work doesn't do well in 'The Closet'. Never mind, only one chapter to go

Chapter Six – I Have a Proposal for You

Delores Cashmore stood by her husband’s gravesite and dabbed at her crocodile tears with her handkerchief. Jeremy Cashmore had treated her badly and left her poor and she was glad to see him gone. She didn’t know how she was going to survive but survive she would. She was a housewife who had no skills whatsoever but she decided then and there that she would no longer live her life doing menial work for men; she would be her own woman.

“How can you dress like a slut at your own husband’s funeral!” her mother hissed as they walked back to the little church.

Delores’ mother was a little harridan of a woman and was one of the reasons Delores had married Jeremy and left home as soon as she could.

Delores was wearing a black short-skirted suit with a white satin blouse, black fully-fashioned stockings and black four-inch high heels. Her makeup was heavy and she was wearing her favourite red lipstick.

“This is how Jeremy liked me to dress mother. On the rare days that he actually went to work, because most of them were spent in the pub, he liked to come home and find me dressed like this and bend me over the kitchen table,” Delores spat her response.

“Don’t talk like that! Not in church!” her mother squawked.

Ada Robinson, Delores’ mother, was one of those women who was content to live a hard life dominated by a brutal controlling husband and thanked God every Sunday for allowing her to exist. She insisted that her daughter attend church every Sunday with her and Delores had been unable to break the habit even after she had moved out of the family home. What she didn’t tell Ada was that God had finally answered her prayers when Jeremy Cashmore had walked out of the pub in a drunken stupor and fell under a number ten double-decker bus.

Nor did she tell her mother that when she lived at home she only accompanied her mother to church so that she wouldn’t be left alone with her father who liked to feel her up while she sat squirming in his lap. Ada Robinson thought that her husband and daughter were just playing a stupid game and chose to ignore the spunk stains on the back of her daughter’s knickers.

Ada and Delores went back inside the little church to thank the Vicar for officiating at the service. There were few mourners at Jeremy Cashmore’s funeral and those who had attended had left quickly. Delores cringed as her mother fawned over the Vicar, expressing her undying gratitude for what Delores thought of as just the Vicar performing his duty. Delores was very much a ‘births, deaths and marriages’ person when it came to religion, she attended church only to hide from her father and her husband.

“There is one other matter I’d like to discuss with you Mrs Cashmore, if you wouldn’t mind remaining behind,” the Vicar said as he walked the women to the big wooden doors of the church.

Ada Robinson once again thanked the Vicar and toddled off down the road.

“Please accompany to the vestry,” the Vicar pointed to the door set into the side of the little church’s rendered walls.

Delores walked ahead of the Vicar who appraised her bottom and long legs. Publicly he would say that he didn’t approve of the way Mrs Cashmore dressed for church but privately he’d played with his erection under his vestments on many a Sunday when Delores Cashmore had sat in the front row of pews next to her mother with her legs unintentionally parted showing a glimpse of her knickers.

The little vestry was gloomy and sparsely furnished with a wooden desk and cabinets that held the church's meagre sacraments. The Vicar took off his vestments and hung them on a coat rack.

“There that’s better. Please take a seat Mrs Cashmore,” the Vicar sat at his desk and indicated a plain wooden chair beside him.

Delores sat down and primly crossed her ankles but her skirt rode up her thighs and she tugged at it and blushed.

“Thank you again for the service today Vicar,” Delores said, although she didn’t really mean it.

As far as she was concerned the Vicar had merely performed the funeral rights that he was bound to do by his position. He confirmed that in his reply.

“Merely performing my God given duties Mrs Cashmore and glad to do so, which is possibly a good segue into the reason I wanted to talk to you,” he smiled at her through yellowed teeth.

“The funeral service comes free of charge of course, although some parishioners like to donate a little something to the church fund,” the Vicar said.

Delores blushed. She didn’t have a penny to donate and she was sure the Vicar was aware of it.

“That brings us to the matter of the grave plot. Unfortunately that doesn’t come free of charge,” the Vicar said gravely.

“Oh my, I didn’t realise,” Delores’ face fell.

“I know things are tough for you right now Delores, I can guess that Jeremy didn’t leave you with much,” he reached out and patted her knee.

“Pardon my French Vicar but he didn’t so much as leave me a pot to piss in. All I have left is the house which he inherited from his uncle,” Delores shook her head.

“Do you mind me calling you Delores?” the Vicar had not removed his hand from her knee.

“Of course not Vicar,” Delores smiled grimly.

The Vicar got out of his chair and walked to the vestry’s old wooden door and turned the ancient doorlock. He looked at Delores intently and smiled through his tobacco-stained teeth.

“There are of course other ways one could pay for a burial plot. It’s not really cheap Delores, around five hundred pounds plus the annual upkeep charges,” The Vicar came back and stood before her.

Delores felt very uncomfortable being eyelevel with the Vicar's crotch.

“Do you understand what I mean by other ways?” he leered at her.

Delores was bemused at first and then she saw the bulge in the Vicar’s black trousers. If Delores had any faith at all it left her right then as did any respect she had for men in general.

Her husband was a drunkard who beat her and would bend her over whenever the urge took him demanding his conjugal rights. Her father had held her squirming in his lap while he pressed his erect penis against her knickered buttocks until he ejaculated while her mother had feigned ignorance. Now the one man she should be able to trust above all others was making a pass at her.

“I understand Vicar,” Delores sighed.

“Then shall we make the first instalment now?” the sound of theVicar unzipping his fly in the silent vestry was ominous.

The Vicar’s penis was quite big and knobbly with pulsing veins and an angry-looking distended purple glans. For some reason Delores thought of the Vicar’s wife who was a short mousy looking woman who always seemed to be wearing a pinafore, thick brown tights and scuffed flat shoes. Delores couldn’t imagine her tending to the Vicar’s needs but she obviously did because they had three children.

Delores set her resolve and reached out and took the Vicar's penis in her hand and began to stroke it. The Vicar gasped as he watched Delores’ slim fingers with those bright-red long fingernails grasp his manhood and begin to caress it. She gripped it tighter and felt the meaty thickness of it pulse in her hand.

She felt utterly disgusted and demeaned as she sat in the wooden chair masturbating the man who had christened her. But she couldn’t deny that she also felt something else. She felt power. Delores realised that she could blackmail the Vicar should she chose to do so. It would be her word against his but surely a bereaved widow would attract sympathy and even if the Church didn’t believe her the Vicar’s name would be besmirched for ever.

Instead of letting go of the Vicar’s erect penis she lowered her mouth to it and began to suckle it. Her husband had demanded this service and she was quite adept. When she closed her lips around the shaft and used her tongue on the bloated glans the Vicar’s knees gave way and he fell into his chair.

Delores followed him with her mouth, getting down on her knees so that she could pay full attention to his cock with her mouth.

“Oh my Delores; no one has ever done that to me before,” the Vicar sighed watching the woman with flaming red hair, heavy makeup, exuding a miasma of perfume bob up and down on his phallus.

Delores worked her mouth on the Vicar’s cock and as she did she gradually realised that not only did she feel powerful, she was also becoming sexually aroused. Her knickers were damp and she felt a tingling in her vulva that she seldom felt when Jeremy fucked her.

The Vicar unbuckled his trousers and pushed them down around his ankles with his underpants and placed his hands on Delores’ head and guided her mouth up and down on his cock but she shook him off. She didn’t like being handled like that, it reminded her too much of her dead husband who had often choked her when she fellated him.

She could feel the Vicar’s cock begin to throb insistently and her quim becoming wetter. She needed something inside her to satiate her lust.

When Delores spat out the Vicar’s cock just as he was about to climax he cried out with dismay but when Delores bent over the desk and raised her skirt he was delighted. She tried to pull down her red satin knickers but the Vicar impatiently slapped her hand away eased the gusset aside and drove his cock all the way inside her.

He smiled when he realised how wet this woman was. He’d always fancied her and regretted having not made a pass at her before now. He gripped Delores’ hips and began to fuck her and she obligingly pressed back against him and wriggled her buttocks appreciatively.

The Vicar’s cock was bigger than Jeremy’s and also Jeremy had seldom been able to maintain a durable erection because he was usually drunk. The Vicar might be a manipulative adulterous cad but he certainly had a great cock and knew how to use it. Delores began to moan as her orgasm germinated and began to grow. It began deep in her vagina where the Vicar’s cock pounded on her G-spot and blossomed into delightful sprigs of pleasure that radiated from her tingling clitoris.

The Vicar felt Delores’ cunt contract around his cock as she orgasmed. She was shaking on her heels and pushing her pillowy buttocks back into him as he gripped her tightly by the hips and drove himself all the way inside her and ejaculated.

The Vicar gasped and stifled the moan that he so wished to howl at full volume as he discharged his semen deep inside Delores Cashmore’s quivering vagina. The aroma of her sex drifted from under her skirt as her juices flowed freely. Delores bit her lip to supress a scream as she writhed and wriggled with lust. This was what sex was supposed to feel like. She might be being coerced into giving the Vicar what he wanted but she had to admit that she liked what he was doing to her. She hated him for violating her when she was most vulnerable but she absolutely adored the pleasure he wrung from her.

Suddenly there was banging on the vestry door.

“Are you in there Vicar?” called Dorothy Clinton, one of the volunteer helpers, as she rattled the doorknob.

“Just a minute Mrs Clinton, I’m changing out of my vestments and mourning suit into something more comfortable,” the Vicar called out.

He pulled his cock out Delores’ vagina and a flood of semen and vaginal secretions soaked into her knickers as the Vicar pulled the gusset back in place over her puffy labia.

Delores pushed herself up from the desk, adjusted her knickers and pulled down and straightened her skirt while the Vicar pulled up his underpants and trousers.

Delores reached into her handbag and found a compact and her lipstick and fixed her face.

“That was an excellent first instalment Mrs Cashmore,” the Vicar grinned at her.

“I’ll make regular payments Vicar, every Sunday after church,” Delores picked up her handbag ready to leave.

The Vicar walked her to the other vestry door, the one that opened onto the church grounds.

“I’ll want a nice marble headstone installed and fresh flowers placed on my husband’s grave every week Vicar,” she leaned into the Vicar and nibbled his ear.

“Now, now Delores, I didn’t agree to any of that,” the Vicar’s yellowed teeth repulsed her when he smiled condescendingly at her.

“Oh you’ll do it Vicar. You’ll do it gladly for your weekly stipend. Either that or I’ll open the other door and call in Dorothy Clinton. Even a muppet like Dorothy will know what’s been going on in here. The place stinks of perfume and cunt,” Delores smiled and the Vicar’s grin soured at the use of such vulgarity in his church.

“See you next Sunday then, shall I Vicar?” Delores smiled sweetly and let herself outside onto the gravel path that cut through the centre of the church’s lush green lawn.

Her knickers were squidgy and uncomfortable but she was smiling to herself. She knew now how she was going to make a living. Men had always fancied her and some of them had used her but from now on she would be using them.

*****

Delores had been using her house as a brothel for six months before Steven Cottrell paid her a visit. She had no idea who he was and thought he was just another punter who had found one of her ‘tart cards’ that she had distributed in all of the public phone boxes in the area.

“You must be the delightful Delores Cashmore,” Steven smiled as he entered her house one Thursday evening.

Delores had not yet converted her cellar into a dungeon but she had renovated it and she led Steven down the stairs to what she called her workroom.

“This is a nice big space you have here,” Steven looked around at the newly painted and carpeted room.

The the four-poster bed and the armoire were in place but the clothing in the armoire was very vanilla: sexy lingerie, a nurse’s uniform, French maid’s uniform, and extremely high heels.

Delores currently had no need for the rubber and leather fetish clothing or the whips, canes and restraints that would eventually be required.

Steven sat on the bed and started to undress.

“You should put in a bar and lounge area where the punters can relax, you know, provide a few extras so you can charge them more,” he was down to his underpants and vest.

Delores thought that her new punter was a little forward giving her unsolicited business advice.

“Also, I forgot to mention when I phoned you. Do you do any S&M or B&D?” Steven stripped off the last vestiges of his clothing and lay naked on the bed.

Delores was wearing a black transparent negligée, matching knickers, black stockings and high heels.

“Sometimes clients ask me to spank them,” Delores said as she approached the bed.

“Yes but what about yourself? There’s a lot of money in that lark. Would you be prepared to take a spanking or a bit of a caning?” Steven propped himself up on one elbow.

“I’ve never thought about it,” Delores sat down on the edge of the bed.

“If I doubled what you're asking could I give you a spanking?” Steven smiled at her.

Delores considered the short, pasty-faced, pudgy, pale-skinned, piggy-eyed man. He had arrived wearing an expensive suit but he was coarse and spoke with a common cockney accent.

“You would pay me double?” Delores’ business was performing moderately well but she was only just making ends meet, especially as she had outlaid a substantial amount to renovate her cellar.

“Yeah I’ll pay you double. Call it a special service,” Steven’s grin widened.

“Sure, ok, why not?” Delores was a little apprehensive but she could use the money.

Steven joined her on the edge of the bed and began to kiss her. Delores didn’t usually let her clients kiss her and she turned her head away.

“I don’t kiss,” she said evenly.

“Look love, if you want to make this a going concern you’re going to have to offer what the other girls don’t,” Steven said, his voice gravelly.

“But…” Delores never got to finish her sentence because Steven grabbed her and forced her down on the bed.

He might have been short and podgy but Steven was strong and he held her down and pressed his face to hers. Delores turned away again and Steven tweaked a nipple until she screamed.

“There we go,” he grinned when she stopped struggling and faced him.

He lowered his face to hers and began to kiss her. He had wanted to kiss those full red lipsticked lips ever since he had laid eyes on her. Delores refused to open her mouth and Steven pinched her hard until she acquiesced and opened her mouth a little. Steve drove his tongue into her mouth and kissed her passionately.

Her husband had liked to use his hands on Delores and often hit her but this was different. The pain was part of the foreplay and Delores wouldn’t admit it but she found it stimulating. She returned Steven’s kisses and used her tongue. She squealed when Steven tweaked her nipples but it was a squeal of both pain and delight.

“That’s good girl,” Steven hissed and kissed her again.

He suddenly sprang off her and dragged her onto his lap and began to spank her buttocks. At first it was just a few painful slaps and then he began to lay into her until Delores’ buttocks were red and burning with pain. He slipped a finger inside her panties and opened her labia and circled her clitoris, whilst still slapping her bottom.

Steven smiled. Delores was wet and although she squirmed with pain she was also squirming with pleasure.

“Oh my god stop! Please stop!” Delores cried and Steven did.

He threw her on the bed and dived on top of her, his stubby penis probing between her legs. He slipped his cock inside the leg-hole of her knickers and found her sex swollen and wet and he drove his cock into her. Delores wrapped her legs around him. Her buttocks were burning and her nipples ached but the pain amalgamated with the pleasure that was radiating from her cunt and forged an intense decadent sensuality that she had never experienced before. Who would have thought that pleasure and pain could coexist and illicit such divine rapture?

Delores lifted her buttocks off the bed to meet Steven’s frantic thrusts. His stubby appendage didn’t quite hit her G-spot with every stroke but his pubis ground against her clitoris and she could feel an intense orgasm blossoming.

She felt Steven’s cock begin to convulse has he discharged his semen in her quivering cunt and she kissed him fervently and raked her heels on his back and held him close and rode her orgasm as Steven’s climax peaked.

When they finished they were sweating, scratched and bruised. Steven lay on top of her panting.

Steven leapt off the bed with surprising agility for a little fat man.

“Clean yourself up luv and we can talk business,” he called over his shoulder as he headed for the bathroom.

Delores lay panting on the bed. Her body was sore, her buttocks burned, her nipples ached but she felt surprisingly contented and when Steven came out of bathroom she went in there and cleaned herself up and fixed her makeup.

When she came out Steven was gone. Delores was angry because he hadn't paid her the extra money he promised.

She became even angrier when she found a besuited Steven Cottrell sitting in her lounge room having helped himself to a healthy dram of her whisky.

“Hey! What the fuck?” Delores was about to berate him.

Steven Cottrell held up his hand.

“Don’t get your knickers in a twist luv. Come and sit down and let me tell you who I am and put to you a new business model for your consideration,” Steven waved his drink at Delores.

“Well it’s not really for consideration, let’s say I’m making you an offer you can’t refuse,” Steven gave her a shark-like grin.

Delores suddenly realised that Steven Cottrell was no ordinary punter.

So Delores entered into a business arrangement with Steven Cottrell whereby she was allowed to operate her own brothel paying Steven a premium for protection from other criminal elements and from the Metropolitan Police Force. She was to provide bespoke services maintaining confidentiality for her clients.

Her business flourished and she was soon overwhelmed so she recruited Felicity Bancroft and Amanda Blundell after vetting them both to ensure that they were willing to provide the unique services she offered to her clients and to maintain confidentiality. Over the ensuing years she made a very good living and her business arrangement with Steven Cottrell proved lucrative for both of them. The feminisation of William Baxter had started out as a whim but once she realised Wendy’s earning potential and her willingness to participate, Wendy joined Delores’ stable of prostitutes and Delores was able to offer Wendy’s special services for those who requested them.

*****

My trip to Bangkok to undergo breast augmentation surgery went surprisingly smooth. I spent only one day in hospital under observation and then five days in a hotel recovering before my surgeon cleared me for the return journey and warned me to take it easy for four to six weeks until I was completely healed.

I was very anxious when I went through immigration on departure from Heathrow but both Delores and John Benstead had told me to remain calm and not to draw any undue attention to myself and assured me that my passport would hold up under scrutiny which it did.

It helped that I was attired in leggings, a longsleeved t-shirt and heels and was wearing full makeup. The customs and immigration officers paid more attention to my pretty face, long legs and shapely derriere than they did to my documentation and Delores had sprung for a Club Class upgrade which also meant I had access to the British Airways departure lounges. I was more confident on my return journey especially knowing that I now had shapely C-cup breasts filling my bra rather than silicon breastforms.

I didn’t venture out of my hotel in Bangkok except to undertake surgery but I wasn’t there for a holiday and I enjoyed an Executive Suite. The airfares, surgery and accommodation had taken a healthy chunk of my savings but as I was only just about to turn twenty I had plenty of time to make up the loss and build my bank account, which was now in Wendy’s name.

When I returned home Delores gushed and fawned over me and refused to let me work until I had fully recovered.

“I can still work Delores, the punters will just have to stay away from my tits,” I said indignantly.

“Oh Wendy. All of your clients know that you’ve had breast augmentation and they are clamouring to see you again; do you really think they will stay away from your news tits?” Delores replied.

“You can’t perform any B&D in your current state and Steven Cottrell has been pestering me about you and so have the other punters on your client list. You will return to work when I say you can,” Delores put her foot down.

My first clients when I returned to work were Steven Cottrell and Anthony Edwards who had paid for a foursome with Delores and I.

“I once again remind you that the safeword is Red gentlemen and ask that you are not too rough with Wendy given her recent surgery,” Delores explained.

Delores was wearing her leather catsuit and handing out drinks in the lounge area of the cellar dungeon. Steven and Anthony were naked under their black satin robes.

“Come off it Delores, she’s only had her tits done. It’s not like she’s had lifesaving surgery,” Steven snatched the offered drink and took a long draught.

“Come on Wendy. Show us your new tits then, that’s what I’m paying for,” Steven growled and reached for me.

I was dressed similarly to when the gentlemen had last visited us: black satin bustier with red garters clipped to long, black fully fashioned stockings, a pair of red satin full-cut knickers and four-inch black high heels. My makeup and hair were perfect and the bustier gave me an hourglass figure with new creamy white breasts filling the cups. I had accessorised with silver jewellery from my growing collection.

Steven roughly extracted my breasts from my bustier and I winced. It didn’t hurt much but the scars underneath my breasts were still tender. Steven hefted my breasts in his hands and inspected them and Anthony joined him.

“They are lovely Wendy,” Anthony smiled at me.

“The scars will fade eventually and will be hardly noticeable after a year,” I smiled at the two men.

“Well I bags first dibs at her,” Steven grabbed my wrist and led me over to the saltire cross.

I had mode love with Delores many times since my return but this would be my first time having sex with a man and I was looking forward to it. I knew that Steven was going to treat me rough but I had to admit that I was longing for it. My cock was already fully erect but I kept it in my knickers as I knew that Steven did not like to see it or touch it.

Steven was a strange man. He liked to kiss me, caress me, whip me, beat me and of course fuck me but he didn’t want to touch my penis. Now that I had breasts for him to play with I knew that he would enjoy playing with them. I always wore full-cut panties when I was with him so that my erect penis was covered and after my first session with him I always made sure that if I ejaculated I did so into my knickers so that he wouldn’t have to see that either.

“Put your back to the cross this time Wendy,” Steven said as we approached the apparatus.

I took position on the cross with my legs spread wide and my arms extended in the X position. I knew the consequences of displaying any amusement when Steven struggled to secure my wrists to the cross. He pressed his body against mine as he did so and his stubby penis rubbed on my thigh. He kissed me and I responded accordingly, slipping my tongue into his mouth.

I felt his cock grow to full tumescence as he kissed me languidly. I quite liked being kissed whilst I was restrained. My usual response was to put my arms around my clients and hold them close and cosset them while we kissed but the impediment of being restrained and the frustration of not being able to fully respond actually added to the excitement and expectation.

Steven secured my ankles and stood back to admire his work.

Previously when we used the cross Steven secured me face first to it so he could punish me and then pull down my knickers and fuck me from behind. It was strange being able to see him and watch what else was happening in the dungeon.

Delores had Anthony bent over the restraint table with his wrists firmly secured. She was laying the cane into his already reddening buttocks and he gave a little yelp of pleasure and pain as she did so. After a few strokes of the cane she would reach under him and squeeze his cock and testes and then stroke him until he mewed and then remove her hand and begin to punish him again. I had seen Anthony endure this for hours with Delores, Amanda and Felicity taking over from each other as they tired.

Steven selected a slim leather flail from the rack on the wall and I tensed in anticipation of its use on my body. Delores’ rule was that customers were not to leave marks on any exposed parts of our bodies which usually meant being thrashed on the back and buttocks. This was the first time that I was to be punished standing face-on to my disciplinarian.

Steven whipped me across my belly. To my relief he didn’t hit me as hard as he did when he thrashed my back or buttocks but I still cried out as the searing pain lit across my tummy.

“What out for her tits!” Delores called from across the room.

“You just keep whipping your Nancy-boy and leave me to my business you old harlot. The tranny knows the safeword,” Steven snapped back at her.

After ten strokes, each which was harder than the previous one, Steven stopped and approached me. He kissed me again and to my shame I became erect. The burning in my stomach and the carnality of Steven’s passionate kisses merged into an intense feeling of rapture over which I had no control. It had been so long since I had been restrained and punished that I forgot how stimulating it was or how much I craved it despite the fact that I despised the man who was administering it to me.

Steven pulled down the bodice of my bustier and exposed my breasts and lowered his face to them. He used his lips to suckle my nipples and when I sighed with contentment as wondrous feelings emanated from my tender teats he suddenly nipped them causing me to squeal. I found myself once again intoxicated by the amalgam of pleasure and pain.

Steven squeezed my breasts and rubbed against me, driving his tongue into my mouth. He must have been able to feel my hard cock against his belly even though it was constrained by my full-cut panties, I could certainly feel his rubbing against my thighs. He had a way of sensing when I was experiencing pleasure and immediately applied pain in one form or another by biting, slapping or tweaking some tender part of my body. He seemed fixated with new breasts and alternately lapped and suckled my nipples then twisted, bit or pinched them. He stroked my milky globes gently and then he kneaded them coarsely.

He kissed me hard, driving and wriggling his tongue in my mouth and he ground his rampant cock against me. He suddenly stopped attending to me and laid into me with the flail making me scream with pain but I refused to use the safeword. For some reason being punished by the man I hated most in the world caused me to become extremely concupiscent, in fact Steven could evoke a satyric lechery in me that no one else seemed to be able to. I often wondered if my loathing for him juxtaposed to the licentiousness that he engendered in me was the reason I responded as I did.

My cock was throbbing, the front of my knickers were soaked in pre-ejaculate, I wanted him inside me. I wanted him to drive that stubby, gnarled monstrosity of a penis into my anus and fuck me hard and violently. I wanted him to violate me!

And that’s just what he did.

Steven grappled with the bonds holding me to the cross and I fell to knees. He knitted his hands in my hair and forced my face into his crotch and I instinctively opened my mouth. He pushed his stumpy appendage into my mouth and I suckled it using my lips and tongue, gratefully accepting the pulsing phallus which was leaking droplets of dewy precum. I tried to use my hand to stroke the shaft and he slapped it away.

“Suck on it you tranny whore!” he put his hands on either side of my face.

He face fucked me, making me gag and choke and I tried to prise his hands from my face. I hated it when men did that to me. But if I hated it so much why was my cock so hard?

I sucked and slavered at Steven’s cock and felt it pulse and throb and I expected to receive a mouthful of semen but Steven pushed my face away. He reached for the flail and whipped me as I scampered across the floor, the blows falling on my back and my rump. Then he entwined his fingers in my hair and dragged me to the bed where he trussed me over it so that my buttocks were raised and my head buried in the duvet.

He pulled down my knickers and thrashed my buttocks. The pain was indescribably and magically spectacular. When my buttocks were red raw he gripped my hips and drove his cock into my tight anus.

I mewled with pain and delight as he gripped my hips and pounded his cock in and out of my back passage. My nipples ached, my back smarted, my buttocks burned and my anus was being ravaged but I felt the most intense pleasure.

My cock strained against my silky knickers pressing against the bed linen, my anus was afire with lustful decadence and I pushed my buttocks back into his groin to ensure that his glans pressed against my prostate.

I ejaculated into my knickers the exact moment Steven ejaculated in my anus. I felt the warm flood of his seed fill me as he gripped my hips and drove his cock all the way inside me and ground against my stinging buttocks. My orgasm was astoundingly powerful and my cock erupted. The spurts of ejaculate that spewed from my pulsating penis burned and tingled and filled my knickers.

Steven pressed against my scoured buttocks, grinding his pubis and eliciting every scintilla of pleasure from me as his cock continued to pulsate and ejaculate his load deep inside me.

Steven pushed me down onto the bed and ripped his cock from my anus. His spend poured from my sphincter and ran down my thighs. He laughed.

“Now that’s how you fuck a tranny!” he guffawed.

I was nearly exhausted, every part of my body ached but I felt exhilarated and deeply satisfied. I rolled onto my back and crawled onto the bed panting with exhaustion.

“Did you come? You dirty tranny whore!” Steven pointed at my sodden knickers.

I stupidly smiled up at him and nodded.

His face filled with rage and he snatched up the flail and began to beat me ferociously all over my body.

“Red! Red! Red!” I screamed but he ignored me and continued to lash me.

I covered my face and rolled onto my back to protect my breasts.

“Stop! Stop! Stop!” Delores ran across the room and grabbed at Steven’s wrist.

He pushed her away and kicked her when she fell. He thrashed her with the flail and then turned his attention back to me and began beating me again. The pain was indescribable. It raged through my body like fire. I cringed and curled up in a ball as Steve rained blows down on my body. The pain exploded with a blinding whiteness. It made me dizzy, almost faint I reeled with it, it was like molten metal being spattered on my skin, like electricity wired straight onto my flesh.

Anthony Edwards was restrained over the table and he struggled to break free. His wrists bled with his efforts and eventually he was able to slide his hands through the cuffs. He dashed across the room and crash tackled Steven Cottrell to the floor. Steven struggled to get up and lashed out at Anthony who had no choice but to defend himself. He punched Steven repeatedly until he stopped struggling.

Anthony helped Delores to her feet while Steven grovelled on the floor attempting to stand. Delores and Anthony crawled onto the bed to tend to me. I was sobbing and incoherent and Delores gently stroked my face and comforted me.

“I’m so sorry Wendy. What Steven did was unspeakable and unforgivable, you are such a lovely and caring young woman and do not deserve in any way to be treated like this,” Anthony leant down and softly kissed my forehead.

“Don’t apologise for me to that tranny whore! She got what she deserved, strutting around like she’s something special!” Steven spat as he struggled to his feet.

“She’s a wonderful young woman Steven, why would say that? Why treat her like that?” Anthony leapt off the bed and confronted Steven.

“You’re no longer welcome here, get out!” Delores screeched.

“Fuck you, you harlot! Fuck that tranny cunt too! And fuck you Anthony,” Steven raged.

“I’m shutting this whorehouse down. You’re finished Delores, you won’t work again and you better watch your back!” Steven strutted across to the valet clothes stand and began to dress.

“And you watch your back too Anthony. You just put your hands on me and you're going to pay for that,” Steven struggled into his trousers.

Delores and Anthony ignored him and tended to me. Anthony went to the bathroom and snatched up a towel which he filled with ice at the bar and brought it over to bed. Delores took it and placed it on my wounds.

“You're all fucked; all of you! You’ll pay for this! She’s a worthless tranny whore and I’m the boss of both of you, so fuck you! I fucking own you!” Steven stormed up the stairs dressed only in his shoes and trousers, carrying his shirt and jacket in his clenched fist.

*****

I recovered quickly but once again I had to take some time off from work.

Four days after the incident in the basement I heard Delores talking to some people downstairs and it definitely didn’t sound like they were punters.

I snuck down the staircase and saw Delores being interviewed by two policemen, one in uniform and one in plain clothes. I couldn’t hear what they were saying but it seemed serious. I guessed that Steven Cottrell had fulfilled his promise to shut us down.

Delores came upstairs when they left and smiled at me as I lay in bed.

“I heard you on the stairs you sneaky possum,” she grinned.

“So the Old Bill is shutting us down at the behest of Steven Cottrell,” I sighed.

“That’s not what they were here for,” Delores approached the bed.

She had her hands behind her back and she smiled at me again and dropped a copy of The Daily Mail on the bed.

‘London Gangster Missing’ the headlines read.

‘Long-time underworld thug and criminal kingpin Steve Cottrell is missing under suspicious circumstances. His car was found abandoned on the M1 motorway outside of Leeds. SOCO officers found blood spatter in the vehicle which matches Cottrell’s DNA which police have on file. No body has been found but the incident is being investigated as a potential murder by the Serious Crime Squad.’

‘The vacancy created at the top of London’s criminal hierarchy caused by Steven Cottrell’s disappearance will likely be filled by Brendan Bourke, Steven Cottrell's deputy or by Anthony Edwards, the head of an associated criminal organisation. It has not been ruled out that Steven Cottrell was assassinated by members of his own criminal organisation following the disclosure of pornographic tapes which portrayed Steven Cottrell as a sexual deviant.’

The article continued but I read no further.

“The tapes?” I looked up at Delores who had a thin smile on her face.

She just gave me a knowing look.

“And Anthony? Where does he sit in all this?” I asked.

“Ah… perfect segue into another conversation. Anthony and I are well… well we’ve decided to make it more of a permanent thing,” Delores patted her hair nervously.

I looked at her quizzically.

“I’m moving in with him,” she murmured, not looking at me.

“You're what?” I was clearly astonished.

“Anthony has moved up in the world. He’s going to be looking after all of Steven Cottrell’s business interests now that he’s gone and he wants a permanent partner.”

“Someone attractive who can tend to his special needs and wants, someone who can be discreet but is intelligent,” she said in a gentle tone.

“But not a brass? The head of London’s biggest crime organisation can’t have a brass as his partner,” I said as the ramifications of what Delores was telling me dawned on me.

“Well technically I’ll be an ex-brass I suppose but yes I won’t be working here any longer,” Delores said softly.

“This has all happened so fast,” I was incredulous.

“Well things went quite off the rails the night Steven went crazy but Anthony seized the moment. Steven Cottrell is no more and he is not missed by anyone,” Delores sat down and crossed her legs demurely.

“The tapes. You released the tapes so that people in his organisation would realise how perverted he was so that there would be no reprisals over his disappearance,” I said.

“I'm on them aren’t I? I’m the reason why that the papers are calling him a sexual deviant,” I was incredulous.

Delores didn't reply she just looked away.

“Like I said it all happened so fast Wendy,” Delores sighed.

“So what happens to me now?” I was still in a state of shock.

“I have a proposal for you. You’re only young but you have an old head on your shoulders. What if you take over the business? I’ve spoken to Felicity Bancroft and Amanda Blundell and they are happy for the arrangements to remain in place with you running the shop,” Delores reached out and took my hand.

I was incredulous, speechless.

“What about you?” I muttered.

“I’ll go live with Anthony and help him with his business interests. I’ll be the perfect wife: a cook in the kitchen, a lady in the parlour and a whore in the bedroom,” Delores smiled at me.

“What about us?” I asked.

“Oh Wendy there will always be us. You know you are special to me and always will be. You’re like the daughter I never had but more than that. You are my lover and my confidant, my pupil and my friend. Things will change but we will still see each other, we will still be close,” Delores climbed onto the bed and snuggled up beside me.

“Amanda Blundell had agreed to move in here with you but you will run the business. She will tend to my clients and be your assistant,” Delores stroked my cheek.

“I’m handing the business over to you… if you want it. If not, Anthony and I are prepared to set you up wherever you want in whatever endeavour you choose,” she looked at me meaningfully.

“I can do whatever I want and you’ll pay for it?” I looked at her incredulously.

“Yes, whatever you want Wendy,” she kissed my cheek.

I moved my lips to Delores mouth and kissed her.

“How soon can Amanda move in? I’ll take the master bedroom of course and I’d like you to help me find a car like yours; I quite like the Beemer,” I said.

“Oh you little ferret! Here I was worrying that I was abandoning you and all the time you’re pondering what it’s going to be like running your own brothel at twenty years of age!” Delores leapt on me and began to tickle me.

The tickling turned to cuddling and then Delores took off her skirt, heels and blouse and joined me under the covers.

“You’re going to be ok. I’ll still be around to help you. You’re strong. You’ll thrive,” she whispered to me between kisses.

“Promise me that you will still be around,” I pulled her close and kissed her.

“Of course I will. You’ll be sick and tired of having me visit and tell me to piss off and go home to Anthony,” she chuckled.

“Ok then. Let’s do it,” I said as I climbed on top of her.

I was wearing satin and lace babydoll pyjamas and my cock was straining at the front of my knickers. I kissed Delores and pressed my breasts against her and my cock into her silken-clad cunt. She lifted her legs and wrapped her stocking-sheathed legs around me.

I gazed into her beautiful eyes and smiled.

“You’re beautiful,” I whispered.

“You’re beautiful,” she returned the compliment.

I prised her breasts from the cups of her bra and suckled on them, lapping at her nipples as they hardened like berries in my mouth. Delores found my breasts with her hands and stroked and tweaked my teats until they became hard and tender and then we kissed again.

Delores reached for me and found me engorged and throbbing in my knickers. She freed my phallus and guided it to her sex. She pulled aside her knickers and the scent of her cunt wafted to my nostrils and when she pressed my glans to her labia they were warm and wet. I resisted the temptation to plunge myself inside her, instead I sopped her when just as my meatus was inside her tight quivering cunt.

“Don’t be mean,” she looked up at me sulkily.

She lifted her groin up and impaled herself on my steely cock which slid into her hot buttery cunt. I fucked Delores slowly and tenderly, kissing her and stroking her. We whispered endearments and cossetted and caressed each other, luxuriating in the feel of satin and nylon on our tender flesh as we ground and rubbed against each other.

When we were both reached climax we clung to each other and kissed each other with such passion that we both sobbed. I kept myself inside her and lay on top of her and Mrs Cashmore hugged me to her body and kissed my hair and told me that everything was going to be alright.

She told me that she loved me and I began to cry.

*****

Jayden Watson and his mother had moved into the house next door to Wendy Baxter’s nearly a year ago. Neither of them knew that their property had once belonged to their next door neighbour’s mother and had been inherited and immediately sold by Wendy Baxter through a real estate broker.

At twenty years of age Jayden was a quiet unassuming lonely young man who worked as a bricklayer but was studying at night to get an MBA.

Ever since he had moved in next door to her, Jayden Watson loved watching Wendy Baxter walk to church. To be fair, he loved watching Wendy Baxter do almost anything. But Sundays were special because she dressed for church where she sat with Mrs Delores Edwards and endured the liturgy just so they could go for tea together after the service.

Wendy Baxter always wore a tight figure-hugging suit with a skirt that was not immodest but it was moulded to her buttocks and thighs with a hem that flirted with being too short for church but wasn't quite, the kick-pleat in the back opened and closed as she walked. The jacket, cinched at the waist by a single button, the buttons on her blouse which was always white, sometimes silk – sometimes satin, strained to contain her bosom.

Her brunette hair, straight, shoulder length with highlights, her makeup was heavy and exotic, as was her perfume. And her legs. Those glorious legs: long, toned, unblemished, and sheathed in the sheerest of sheer shiny nylon. Her hosiery glistened in the sun. Her feet were shod in four-inch pumps, always black.

She was not just pretty she was beautiful, her face was interesting and when she smiled she looked beguiling. Wendy Baxter had a thing for red lipstick; she always wore it.

Jayden Watson guessed that Wendy was in her thirties. She looked alluring and she was stylish; always well dressed, only occasionally in jeans, but usually in a skirt or a dress and she always wore nylons and heels. She even wore hotpants with pantyhose with a designer t-shirt when she worked in the garden. Jayden didn’t know what she did for a living, she came and went at strange hours and Jayden wasn’t about to ask but he was keen to know.

Jayden Watson referred to Wendy Baxter as a MILF: Mother I’d Like to Fuck.

The End

Author's Request: I know this story wasn't everyone's cup of tea but if you took the time to read it, please take the time to leave a comment