Walk a Crooked Milf Ch. 04

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

"There's a good girl," Steven laughed and spanked my buttocks.

"Now let's get to fuckin'" he chuckled.

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

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

I could feel his cock convulse and a river of semen expel from his engorged cock and I pressed back against him as hard as I could and ground against him as I also climaxed.

My semen spattered on the rubber matting and I groaned with lust. Steven held me tightly by the hips and mashed his groin into my buttocks as he spent himself inside me. He made a few insistent thrusts and then pulled out abruptly.

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

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

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

"You dirty tranny whore!" Steven bellowed.

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

"Red! Red! Red!" I shrieked.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

"It's more a dull ache at the moment," I replied.

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

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

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

"How old are you Wendy?" he asked.

"I'm nearly nineteen," I replied.

"So young. So naïve," he sighed.

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

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

"So?" I asked, a little puzzled.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

"Is it always like that?" I asked.

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

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

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

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

To be continued