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.
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