Walk a Crooked Milf Ch. 04

Chapter Four - That Man Is No Gentleman

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 profferred 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 a 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 Steven 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.