Walk a Crooked Milf Ch. 06

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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 into 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.