Walk a Crooked Milf Ch. 05

"I'm glad that you like me Barry, I like you too," I snuggled up to his stocky body and nuzzled him under the neck.

I knew that Barry was fascinated with me so why not indulge him? I kissed him and when he tried to return the kiss with a sloppy open-mouth, thin-lipped smack I stopped him.

"Like this Barry. There's no need to be so impatient, I'm not going anywhere," I straddled him with a knee either side of his thigh.

He was naked and his cock was at attention and rubbing on my knickers.

I softly placed my lips on his and opened my mouth just a little.

"Now you do it," I whispered and he let his lips soften and opened his mouth partially.

I kissed him again and he duplicated my actions. When I put the tip of tongue into his mouth he did the same to me. When I kissed him a little harder, he did the same. He had stopped slobbering and trying to force his tongue down my throat, I had taught him how to kiss... and he liked it.

He put his arms around me and kissed me, bobbing me up and down in his lap. He slid his cock in the crevice between my buttocks and rubbed it on my gossamer-thin knickers. I became engorged myself and my cock distended the front of my knickers and rubbed on his belly.

Barry was getting excited again, thrusting against my bottom so I put a hand down there and slid the gusset of my knickers aside and guided his cock to the entrance of my anus which I had pre-lubricated. Barry stopped thrusting when his glans nestled in my sphincter. I smiled at him and he smiled back as I slowly lowered myself onto his long, thick hard cock.

"Mugh," I grunted when it was fully inside me.

It was in me so deep that it threatened to enter my bowel.

"Am I hurting you?" Barry said, concern evident on his face.

"No. It's lovely Barry," I smiled down at him and then lowered my face and kissed him deeply.

I began to ride his cock, letting it come almost all of the way out of me and then slowly impaling myself on it until it was buried to the hilt inside me. I wriggled my bottom to stimulate my prostate and then set about generating a slow and steady pace even though Barry was becoming insistent.

I kissed him passionately but refused to increase the pace of our lovemaking. I really liked having his engorged manhood inside me. I stroked his face and wiggled my buttocks while I kissed and fucked him. I could feel his cock fully bloated, pulsing inside me. It felt so wonderful that I was tempted fuck him hard and fast but I resisted the temptation until we were both close to extremis.

I drove my knickered buttocks into his lap and kissed him hard and fervently, writhing on his cock, evoking his climax and he held me tight as he spent himself deep inside me. I contracted my anal muscles and milked him of his semen and I felt his warm seed flood my back passage.

I filled my panties with my own ejaculate as I orgasmed with him.

We clung to each other and writhed and wriggled and kissed and fucked until I fell against him exhausted and panting.

"That was nice Wendy," he patted my back affectionately.

It turned out that Gladys was missing out on more than just Barry's long thick cock. He had quite the libido to go with it. After recovering quickly he took me over to the big bed and lay me on my back and fucked me long and hard. I was quite relieved when he finally climaxed because my anus was getting sore.

After a break for cigarettes and drinks he wanted to go again but I just didn't have it in me so I fellated him on the sofa and swallowed a healthy dose of creamy cum. He really liked me using my mouth on him because guess what? Gladys didn't do that either.

When I saw Barry to the door it was way past the allotted time he had paid for but I didn't mind because he was such a kind sweet man. He wanted to give me a tip but I refused.

"You're just a softy Wendy," Mrs Cashmore teased me after I had showered and changed into my babydoll pyjamas.

We were snuggled up on the lounge watching late-night TV.

"I'm an astute businesswoman Delores. He'll definitely be back because I looked after him so well," I replied.

I was lying on the couch with my face was on Delores thigh and she was stroking my hair.

"I suppose so but I hope he hasn't put that derriere of yours out of action, you have three customers tomorrow," she caressed my cheek with her long elegant finger.

"I'll survive," I stifled a yawn.

"Too bad you're tired, your face is right where I want it to be, my punter got me close a couple of times but didn't quite get me over before he came," she smiled down at me.

I got to my knees and opened Delores' gown. I could make out the coral pink slit of her vulva through the transparent knickers she was wearing. Her scent drifted to my nostrils and I followed it. Delores opened her legs wide and gasped when I put my tongue on her. I lapped at her vulva through her knickers and was rewarded with the decadent tang of vaginal secretions as she became instantly wet.

I eased aside the gusset of her knickers and continued to lick her outer lips, teasing her and making her shudder. Delores tried to push my face into her sex but I resisted. I made her wait, licking and nipping at her labia majora until I opened the fleshy flaps and found her soft delicate coral-pink inner lips. I circled my tongue around them deliberately keeping away from her clitoris.

Delores was panting and had opened her legs as wide as possible and was pushing my face into her crotch.

"Come on Wendy, please... go there... do it... oh god!" she screamed and ensnared her fingers in my hair when my tongue lashed her clitoral hood.

I used my tongue in a gentle back and forth motion then small circular movements directly on her clitoris knowing it would drive her wild and Mrs Cashmore groaned with contentment. Her vagina secreted more aromatic fluid which I gratefully lapped up then went back to work on her clitoris.

Mrs Cashmore was writhing on the couch, her fingers entwined in my hair, pushing my face into vulva. I slid two fingers inside her vagina and found her G-spot and stimulated it as I licked and sucked her clitoris.

This had the desired result and Delores moaned like a slattern as her orgasm erupted. She held my face to her sex and I lapped at her clitoris and massaged her G-spot until it became too sensitive for her and she tore my face away from her pubis and lay back panting on the sofa.

"Come here," she whispered and smiled at me when she regained her composure.

I snuggled up to her and kissed her. She could taste her own secretions on my mouth which she explored with her tongue so she could lap up every vestige of her juices.

"You're a good girl Wendy. I've trained you well," she sighed.

We snuggled on the sofa until we were too sleepy to stay awake, then we trundled off to our respective beds. It was going to be another busy day and we both needed rest.

I settled into a steady routine performing household chores for Mrs Cashmore during the day, keeping the dungeon clean, the bar stocked and tending to punters in the evenings. William's psyche had totally disappeared and I seldom thought of him except when necessary such as when accessing his bank account which I had seconded. Although my mother lived next door I seldom saw her and she made no attempt to contact me. She was ashamed of me and I suppose she had a right to be.

It wasn't so much that I was living my life as a trans woman, although that would have been enough for her disown me, it was because I was prostituting myself and living with the woman she hated more than anyone in the world.

As my bank account swelled I gave more thought as to how I might continue my transformation. I knew that to be eligible for hormone therapy or reassignment surgery or any form of support I would have to undergo months or possibly years of therapy. It was not that long ago that gender dysphoria was still considered a psychological or psychiatric disorder and there were plenty in the medical profession who still felt that way.

Because I had come late to recognising that I wanted to live as a woman I doubted I would be an acceptable candidate, particularly as I had not presented any gender dysphoria prior to turning eighteen. I also suspected that when I told my story about how my need to transition had come about and how I was supporting myself through prostitution I would not be accepted as suitable for assisted gender reassignment.

The other issue I battled with was that I had no inclination to fully transition. I just wanted a feminine body inclusive of breasts but I did not want to change my genitalia. I wanted to live as a transsexual, transgender woman... whatever label suited. I didn't care what others called me. To me I was just Wendy who was a special girl who attracted men who liked special women like me... and there were plenty of them.

Delores Cashmore's client base had swelled significantly when word of my existence spread. Punters who had a penchant for me told friends they knew who liked the same thing. I still provided B&D and S&M services but most of the punters who came to see me simply wanted to spend time with a young pretty trans girl.

I knew that Mrs Cashmore trusted me fully when she showed me how to manage her booking services. She had a small office set up in a space under the stairs that wasn't much bigger than a closet. Both of us could just squeeze in. Bookings were still mainly made over the phone and she had an answering machine set up on a separate landline and also had dialup internet.

Most of the clients demanded secrecy and that's what made Mrs Cashmore, her two cohorts Felicity Bancroft, Amanda Blundell and myself attractive to the punters. Mrs Cashmore manned her business phone from one o'clock to three o'clock in the afternoon on weekdays and Saturdays or clients could leave messages on the answering machine outside of these times. She also had an email address and had Windows 2000 installed on her PC.

Punters could ask for specific services from specific women or just specify what their kink was and when they would like the service provided. Mrs Cashmore ran a spreadsheet in Excel and assigned punters to each of us. She advertised special events such as the orgy she ran once a month.

She would pass punters onto Mrs Bancroft and Mrs Blundell who worked from their own homes and also had their own smaller client lists.

It was a complicated system but it worked. We were all making good money and the clients usually got the services they requested when they wanted them. Mrs Cashmore of course was making the most money, taking a cut from each of us but for that she ran the booking service and paid protection to Steven Cottrell who passed a percentage onto his contacts in the Metropolitan Police's Clubs and Vice Unit to keep them at bay.

I was still wary when I was out on my own but my confidence grew with each foray I made out into the wider world. My main concern was that I didn't have any credentials in Wendy's name so in event I was asked to provide any form of ID I only had that of William Baxter. I used my credit card in cash vending machines and paid for everything in cash.

"Can I get a passport?" I asked Delores after I had been living with her for nearly a year.

"You mean a forgery? A good forgery?" she looked up from the Daily Mail and studied me.

"I want to go overseas and get breast implant surgery," I replied.

I had been taking black market female hormones and my body had changed somewhat. I hardly had to shave any longer, my thighs, hips and buttocks were bigger and my face was more feminine but my budding breasts had stopped at an 'A-cup' and all my research indicated that they would likely not get any bigger. It was a balancing act because if I upped my hormone dose I would lose my ability to maintain an erection which I still wanted to be able to do and so did most of my clients.

"You're impatient Wendy but I can understand your frustration," she put down her paper and patted the sofa beside her.

"I'll be up front with you, I have only one contact that I trust who could get you a passport that will pass scrutiny," she said and looked at me gravely.

"Steven Cottrell," I sighed.

"Exactly and I know he is not your favourite person," she sympathised.

I'd been requested to service Steven Cottrell a number of times and each time he had treated me brutally. I had become accustomed to being restrained and spanked, whipped and caned and provided it was done within the bounds set by Delores I usually enjoyed it. But Steven Cottrell was savage. He liked to punish me until I used the safeword and then take me roughly.

He paid a premium but if possible I preferred not to have to service him.

"Can you negotiate on my behalf? I really want proper breasts, other than that I'm happy with my body. I bet the punters will like it too if I have a decent pair of tits," I countered.

"We've had these conversations in depth Wendy and I know that you want to progress your transformation but I think you should really go and see a psychologist or at least talk to your mother," Delores took my hand and held it.

She saw the storm begin to build on my face.

"Alright, alright, I'll see what I can do for you but I hope you don't live to regret it," she relented.

"Thank you Delores," I kissed her on the mouth.

"Ok, go about your chores and join me in the office at one o'clock," she kissed me and sent me on my way.

*****

John Benstead was still running his forgery and counterfeit business even though his transgender wife Candy Pops earned a good wage working in a managerial position for Goldwing Airlines where she had started out as hostess back in the late 1970s. Candy had also worked as a drug mule for London gangster Tony Carlotta when she was working as a hostess on Goldwing's premier Skyliner service to and from Singapore.

John Benstead had been Tony Carlotta's counterfeiter and when Tony Carlotta had died Steven Cottrell had moved in and taken over Tony's criminal organisation. Now in his sixties and near retirement, John Benstead usually didn't do mundane counterfeiting or forgery work. He had a small team who he had personally trained who did it on his behalf passing on a percentage of the profits to Steven Cottrell.

His business still operated out of the dodgy dilapidated building in a back street of Moulsham near Chelmsford. It was the perfect front for a fraudster and forger to ply his trade.

As I made my way down the dark alley strewn with abandoned shopping trolleys, junk food wrappers, empty beer cans and bottles, cigarette butts and condom wrappers I shuddered. I was taken aback when I passed a doorway where a fat, middle-aged prostitute wearing a cheap vinyl miniskirt, faux leopardskin blouse and laddered fishnet stockings was being shagged against the wall by a man in a business suit.

I deliberately looked away and continued down the alley until I came to an innocuous looking door with peeling blue paint. The door was actually solid steel and almost impenetrable. I knocked on the door and it opened just enough for me to enter; before me stood a man of indiscernible age but probably in his sixties. His handsome face had had some work done and he was still lean, fit and tanned and he was wearing tight jeans and a Transvixen t-shirt circa 1975.

"What is it about me that I seem to attract girls of your type?" he smiled, the smoke from the cigarette dangling from his lips curling up around his eyes.

"What's that?" I was bemused by the ultra-modern interior of the building that contrasted completely with its shabby exterior.

There were long tables with gleaming machines, myriad cameras of various types set on tripods or mounted over document tables. There were copiers and printers and reams of paper everywhere.

"I met my Missus, Candace or Candy as she prefers right here in this workshop where I made her first passport before she legally changed her gender and got a kosher one. I made a passport for Valerie Swindon who ran a finishing school right down the road in Chelmsford and believe it or not I made one for Michelle Murphy formally known as Cherri Pops, the lead guitarist of Transvixen. Michelle actually introduced me to Candy," John grinned at me and put out his cigarette in an overflowing ashtray.

"All before your time dear but if you Ask Jeeves you'll find them all," his smile widened.

"Don't forget Charlie Ringwald, the only survivor of the Essex Slasher, I've done my homework," I smiled back at him.

"So, Steven Cottrell told me I was to handle this as a personal favour for him," John became serious.

"How's a nice young girl like you got herself involved with that sadistic cunt?" John opened a drawer and took out some paperwork.

"Does it matter?" I replied.

"Not really. Mister Cottrell is the boss and whatever he wants he gets," John laid out a number of passport stencils on the table.

"You can go and stand over there next to the wall where that canvass screen is hanging," John instructed me.

I put down my bag and stood with my back to the canvass screen. I was wearing a short-skirted navy blue business suit, black high heels and tan pantyhose. I'd had my hair styled and paid particular attention to my makeup for the passport photo.

My youthful good looks, curvaceous figure and long shapely legs were not lost on John Benstead who ogled me through the camera lens.

"You're too young and pretty to be a brass but I can't figure out what other connection you might have to Steve Cottrell," John said as he fiddled with the camera.

"Delores Cashmore warned me about you," I replied, nonplussed by John's probing.

"That explains it then. You're one of Delores' brasses. I never knew that she'd branched out into girls of your type or I might have availed myself of her services," John lifted his head and smiled at me.

"And what about your wife Candy? What would she think of you using Mrs Cashmore's services?" I replied satirically.

John burst out laughing.

"The missus would likely want to tag along. We're both getting long in the tooth but we still like a bit of variety in our sex life," John grinned.

"Just take the photographs please Mister Benstead," I huffed.

John shrugged his shoulders and took the pictures. When he finished he offered me a drink.

"I'm driving Mrs Cashmore's car and I don't have a licence in my name so if I get pulled over I'm a goner," I replied, turning down my mouth.

"That's all right luv, I'll make you a driver's licence too," John smiled back.

"It's a piece of piss and I can do that for you now if you'd like to wait," John patted an overstuffed lounge chair.

I considered my options and realised that I should have asked for the licence as well as the passport.

"Can you do me a birth certificate too?" I asked.

"Now you're pushing it," John smiled at me.

I ignored the lounge chair and sidled up to John Benstead.

"I can make it worth your while," I whispered and nibbled his earlobe.

"I bet you can," John grinned at me.

He fiddled with some paperwork and then had me sign a specimen signature on the blank driver's licence. It was the first time that I had actually signed my name as Wendy Baxter and I was thrilled to do it. I gave him another signature for the passport.

He put the document into machine and a few seconds later a plasticised driving licence with my picture and signature on it emerged. John walked over and showed it to me.

"Lovely," I said excitedly.

John snatched it away from me when I reached for it. He hid it behind his back and I rubbed up against him playfully and attempted to retrieve it.

John pulled me against him and kissed me and I responded. I returned his kisses and reached for the bulge in his jeans. John gasped when I unzipped him and dropped to my knees.