Walk a Crooked Milf Ch. 03

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 me 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 your 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 and 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.