Walk a Crooked Milf Ch. 05

Chapter Five - Can I Get A Passport?

After four weeks of being confined in Mrs Cashmore's house I desperately wanted to go out, the furthest I had been was the back garden to hang out the washing and assist with the gardening. Delores did the shopping on Saturday and went to church every Sunday. I quizzed her about that but her response was vague. She said that she had been bought up a Christian and despite her chosen profession she still practiced her faith on Sundays.

Most days of the week we entertained gentlemen callers. At first, most of them wanted the services offered by Mrs Cashmore but as the word got around about the young pretty transvestite living with Delores I started to become popular. Sometimes we would entertain gentlemen together down in the cellar and sometimes we would entertain them individually. Some of the punters wanted to engage in B&D or S&M but surprisingly most did not, they just wanted sex.

I became accustomed to providing sexual services daily and was jealous of Delores when my services were not required. Delores continued to feminise me, working on my gait, posture, mannerisms and voice and I was a willing pupil. For all intents and purposes William Baxter had disappeared. When I wasn't tending to the needs of customers or practicing my femininity I kept house for Mrs Cashmore sometimes joining her to tend to the garden.

My mother saw me outside in the garden on a number of occasions and I wondered how she felt about my chosen lifestyle and also wondered what she had told our acquaintances, which were admittedly few. Not that I cared. I was already wondering if it was possible for me transform from a man to woman. Mrs Cashmore had a personal computer which she used to manage her business and she also had a dialup modem. I found a few fledgling internet websites dealing with transgender issues but there was little information available about how to actually transition. It didn't help that transsexualism, as it was termed at the time, was still considered a mental illness in the UK in the year 2000.

I openly discussed the possibility with Delores who was sympathetic to my cause but advised me to take baby steps.

"There are quite a few transvestites getting around quite openly Wendy and some are so feminine that they are seldom clocked. You know what that term means right?" she asked me.

"Yes and that would suit me just fine," I replied.

"Then we need to get you out and about and build your confidence. I can honestly say that you are very passable. The first thing we need to do is get you a suitable wardrobe. Dressing provocatively will attract undue attention," she explained.

"But before that we need to discuss finances. I intend to take half of what you earn. I think that is fair as it not only covers my stipend as your Madame but includes your room and board. I'm prepared to right off the money that I already spent on your clothes and makeup but you will need to become self-sufficient," she continued.

"Wait! Does that mean that that I can stay? That the trail period is over?" I asked eagerly.

"You are performing your duties to a very satisfactory standard Wendy and I find you have a tolerable disposition. I quite like your company," Mrs Cashmore smiled at me.

I hugged her and kissed her enthusiastically until she peeled me off of her. Our relationship had changed significantly since I began to live with her. I still worshipped her and we sometimes had sex if we had a night without having to tend to punters but we had also become sisterly. I was still her pet project and she delighted in teaching me the nuances of femininity and she still occasionally disciplined me but we were companions and confidantes who lived and worked together.

"These are your monthly earnings after expenses," Mrs Cashmore laid out nearly two thousand pounds in cash on the table.

"Oh my god Mrs Cashmore, really!" I was stunned.

"You're averaging two to three punters a day Wendy. So over the last month you've earned a pretty penny. Our services don't come cheap," she picked up and fanned the bills.

"I take it you have a bank account in William's name that you can still use?" she asked.

"And a credit card," I replied.

"You will have to keep using that until we can establish Wendy Baxter's legal identity. Nothing you have in your wardrobe is really suitable for street wear. A matron like myself getting around in a business suit is de rigueur but a teenage girl dressed like that will attract attention. Let's see what I have in my wardrobe that might be suitable," Delores said.

"Time to go shopping Wendy," Delores smiled at my enthusiasm.

Driving to Brent Cross shopping centre I was both apprehensive and excited. I was apprehensive because it was my first foray into the world in my femme persona and I was terrified that I was going to be clocked and ridiculed and I was excited because... well it was my first foray into the world in my femme persona.

Delores found a pair of black leggings and black long sleeve chiffon side-buttoned office blouse with a mandarin collar. It was stylish but not ostentatious and I wore the leggings and blouse with a pair of red three-inch high heels that Delores had bought for me as my other heels were outrageously high for everyday wear. She toned down my makeup and with my brown shoulder-length hair with the balayaged highlights I looked attractive without appearing trampy.

I was experienced at retracting my testes into my inguinal canals and tucking my penis under my perineum. I held the tuck in place by wearing a pair sheer to the waist pantyhose under my leggings and went sans panties so that there was no VPL on display. There was no tell-tale bulge in my crotch area just a smooth V. With my breastforms in the cups of my bra I had an almost perfect figure.

"The boys are going to go bonkers for you Wendy," Delores teased.

"I don't want them to go bonkers for me, I want them to leave me alone until I become less self-conscious," I replied.

"Besides, they are just as likely to go bonkers for you Delores," Mrs Cashmore was wearing her usual livery: a charcoal grey suit with a tight pencil skirt that rested three inches above her knees, white satin blouse, black heels, and shimmering tan hosiery.

Her makeup and hair were perfect and she was wearing her signature red lipstick.

"Nonsense! We'll look like mother and daughter," she smiled at me.

"I'll keep an eye on you. Stay close and behave as normally as you can. You are beautiful and passable; nothing bad is going to happen, I want you to enjoy yourself," she reached over and took my hand in hers and squeezed it affectionately.

My heart was in my mouth when we turned off Prince Charles Drive into the multi-story parking garage and got out of her BMW. It wasn't too bad initially because there were few people in the car park and those who were there were coming and going to their vehicles taking little interest in two women out for a day's shopping.

All that changed when we entered the open well-lit space of the shopping centre. I immediately felt that all eyes were on me and I clung to Mrs Cashmore for moral support.

"Be cool calm and confident Wendy. Look around carefully and you will see that hardly anyone is looking at you and the few that are, are giving you an admiring glance. People are here to shop not to play 'clock the tranny'," she made me halt at a bench near a set of escalators and allowed me to gather my wits.

My confidence built slowly as we made our way from shop to shop and my attention was diverted from the people around me to the wonderful goods on display. We concentrated our efforts on Fenwick, John Lewis and Marks & Spencer and I immersed myself in the shopping experience and thoroughly enjoyed selecting clothing, lingerie, hosiery, footwear, makeup and accessories.

Delores accompanied me to the fitting rooms when I needed to try on various items but I soon felt confident. At first I was very nervous interacting with the staff but I soon realised that their only interest in me was trying to sell me their products. I think one of the more mature shop assistants might have suspected that I was trans but she politely said nothing.

After spending a considerable amount of my stipend and making three trips to and from the BMW I was done. I had a complete wardrobe.

"When we get home I want you to move all of your fetish clothing down to the cellar and leave your daywear in your bedroom," Wendy said as we sat sipping coffee in the food court.

"I need to go," I whispered.

"To go where?" Delores frowned at me.

"I need a wee," I iterated, crossing my legs in discomfort.

"Well go you silly girl," Delores said patting my hand.

"Time for the butterfly to fly on her own," she smiled and nodded at the sign for the toilets.

My nervousness returned as I approached the ladies loo. This would be my first time using a ladies convenience and I was very self-conscious. I knew that I needn't be. I had not been clocked all day except perhaps by one shop assistant who had got up close and personal taking my measurements for a suit.

I set my resolve and opened the door to the loo. There were three young teenage girls hanging around the back corner near the vanities illegally smoking cigarettes.

"What are you looking at you stuck up bint," a girl with frizzy blue and orange streaked blonde hair wearing black tights, pink hoody and hi-top trainers snarled.

She wore heavy dark eye makeup and pink lipstick and was smacking gum between dragging on her cigarette. Her friends were similarly dressed and they all exuded teenage angst disapproval and rebellion.

I ignored them and went into the closest cubicle and locked the door. My need to pee far exceeded my fear of any teen outrage and indignation. We were in a high-end shopping centre and the girls were hardly a street gang.

I pulled down my leggings and pantyhose and bunched them around my ankles and sat on the toilet. My penis dropped down and I sighed with relief as I unleashed a steady stream of urine into the bowl. I had been sitting down to pee ever since I had decided to live full-time as Wendy so it was not unnatural for me. When I finished I wiped and stood up to tuck, pulling up and smoothing out my pantyhose.

As I leaned down to smooth out my leggings I heard a snigger above my head.

"Hey girls, she's a tranny," the rainbow-haired girl was standing on the toilet seat in the adjacent cubicle peering over the top of the partition.

I opened the door to the cubicle and the other two girls were standing against the bank of sinks opposite looking menacingly at me.

"Excuse me, I need to wash my hands," I said not making eye contact.

The rainbow haired girl kicked open the door to the cubicle in which she had been spying on me and joined her colleagues, preventing me from approaching the sinks.

"You fucking freak. You shouldn't be in here you fucking perv," she snarled.

"I'm just using the facilities and now I'd like to wash my hands and leave," I replied indignantly.

"You're a fucking bloke dressed as a woman, you shouldn't be in here," one of the other girls retorted.

I decided that the best course of action was to leave the lavatory and wash my hands somewhere else but the girls formed a phalanx in front of me preventing me from leaving.

"You're a fucking nonce and we don't like nonces do we girls?" the teenage witch looked at me, her rage evident in her stance and on her face.

"You know what we do with pervs with you? We kick their fucking arses don't we girls?" she looked at her two compatriots for support and they nodded their agreement.

"Are those tits even real?" one of the girls pointed at my chest.

The girls must have been fifteen or sixteen at the most and I could easily take them on individually but with them fighting as a pack I was about to be overwhelmed.

"Ok you bitches, come and kick my arse but at least one of you going to get seriously hurt," I prepared for the assault.

The girls looked at each other a little unsure if they should proceed but the rainbow-haired witch gritted her teeth and leapt at me. I lashed out with my three-inch heels and caught the rainbow warrior right in the crotch and she came to an abrupt stop and curled up on the tiled floor holding her hands to her cunt.

I knew that a kick pleat is an inverted pleat used at the base of a narrow skirt to allow the wearer more freedom of movement. But it was the first time I ever saw it used to actually allow someone wearing a tight pencil skirt to kick someone which was exactly what Mrs Cashmore did as she came through the door to the lavatory. She kicked one of the teenage girls in the arse so hard that she went sliding across the tiled floor and joined her rainbow-haired friend.

"Would you like a bit of slap and tickle too luv?" Delores glared at the remaining girl who was trembling in her boots.

She scooted past Mrs Cashmore and ran out into the shopping centre.

"Let's go Wendy, I think we're done here," she smiled at me.

I smiled back at her and made to leave.

"Wash your hands first, there's a good girl," she admonished me.

I washed my hands looking at the two sorry looking teenage girls curled on the floor, one nursing her twat the other her arse.

"I'm telling my brother!" rainbow whined petulantly.

"Tell him. I've probably got a bigger dick than him anyway," I retorted and left the lavatory to join Delores who was retrieving the last of our shopping bags and parcels from the shopping centre help desk.

We made it all the way to her BMW before we both cracked up. We hugged each other as tears of laughter ran down our cheeks and then the laughing stopped and we kissed.

"Shouldn't be allowed!" an old crone remarked as she walked past dragging along her two grandchildren who were both staring at us open mouthed.

That remark cracked us up again and we howled with laughter and clung to each other.

At that moment in time I was never more in love with Delores Cashmore.

We both had customers that evening and I was grateful that the man who wanted my company did not want any bondage and discipline play; he just wanted to spend an hour with me.

He was a nice married man in his fifties and Delores explained that the man's wife was frigid and he'd developed a thing for transsexual and transvestite women. The fact that I was so young had emboldened him to hand over nearly the equivalent of a week's wages to Delores so that he could spend some time with me.

Delores was entertaining one of her trusted regulars and she took him up to her bedroom allowing me and my punter to use the four-poster in the cellar dungeon.

"Would you like a drink?" I said to the man who was visibly shaking with excitement.

I was wearing a red leather miniskirt, a white satin blouse, tan nylon stockings and the same red heels I had worn to the shopping centre earlier in the day. My makeup was heavy and I was doused in perfume.

The man was speechless when Delores introduced him to me; all he could do was stare at me so I took his hand and I led him down to the cellar.

"I'm Barry," the man offered me his hand.

"Oh come on Barry, give a girl a kiss," I sidled up to him and pressed by body against him and kissed him.

He was not a very good kisser, all open mouth and sloppy tongue but I let him kiss and grope me. His hands went straight to my skirt and he squeezed me quite hard and then he hiked up my skirt and groped my knicker-clad buttocks and silken-sheathed thighs.

"I wish Gladys would wear stockings for me. I just wish Gladys would let me touch her," the man mouthed around squooshy kisses.

Gladys was obviously Barry's wife.

Barry was getting overexcited and I managed to untangle myself from his grasp.

"Let me get us both a drink Barry. We've got plenty of time and you don't want to come in your trousers do you?" I turned my back on him and was about to pour us drinks when he sidled up to me.

"I'm sorry Wendy. I've never been with anyone as young and as pretty as you and I can't keep my hands off you," he sighed.

"Maybe I should let you have a quick one and then you can recover and take your time with me," I turned and smiled at him.

"Would you luv? I think I'm going to cream my jockeys just looking at you," he gave me a pathetic smile.

"Oh course you can Barry. You know what they say? The customer is always right," I smiled at him and closed the gap between us.

I let him kiss me, his tongue seemed too big for my mouth, it was wet and fleshy and he moved it around inside me like a snail retracting into its shell. His lips were thin, damp and unyielding and he pressed them to mine, urgently sucking and lapping at me as he held me in a vice-like grip.

I knew that it was just excitement, inexperience and awkwardness on his part and I did not judge him harshly for it. Delores had trained me well. I was here to please the men who paid for my company and it was my job to make sure that they had the best experience possible.

I was wearing tight, white, full-cut translucent knickers and Barry had my skirt up again and was pawing at my buttocks, holding me close against him. I put my arms around him and returned his kisses as best I could, I could feel the heat and hardness of his manhood pressing against me, his need for release was almost palpable.

I was able to slide a hand between our bodies and unzip his flies and free his erection. Gladys, whoever she was, was missing out on a rather useful penis. Barry might be older and clumsy but his cock was a magnificent specimen. Long thick and smooth, it throbbed in my fingers.

I guided it between my legs and closed them tight so that the meaty weapon was clamped between my stocking-tops. I rocked back and forth as Barry began to fuck my legs and my diaphanous nylon-clad thighs massaged his engorged cock. He gasped into my mouth and pulled me even tighter as I felt his cock quiver and palpitate and then his scalding semen spattered down the back of my legs soaking into my stockings.

"Oh god, I'm sorry," he began to cry.

"It's fine Barry. I like it. It means that you find me really attractive and sexy if I can elicit such a tremendous response like that from you so quickly," I clung to him and kissed his neck softly.

He held on to me, sobbing quietly, his semen cooling on my legs. I whispered endearments into his ear and placed soft kisses on his cheeks and his mouth until he calmed down. Eventually he issued a huge sigh of contentment and I disengaged from him. I cleaned my legs with some tissues.

"I'm sorry," he had his head down like a chastened schoolboy.

I lifted his chin and kissed him quickly.

"Did you enjoy it?" I asked.

Barry nodded his head bashfully.

"Then all is well with the world Barry. Let me fix us a drink and we can go and sit down if you like," I smiled at him and he grinned back at me and nodded.

He self-consciously tucked his trunk-like appendage into his underpants and zipped up his trousers and took the drink I offered him. We adjourned to the couch and I deliberately sat close to him so that our thighs were touching.

"So Barry, do you like special girls like me specifically?" I asked, stroking his forearm.

"Yes I do but there aren't that many of you. When I was a young man I used to go to Chelmsford and see a girl called Charlie who worked under the railway overpass but she moved on. She was a victim of the Chelmsford Slasher but that was way before your time," Barry sighed.

"It's risky picking girls up off the street so I save up my money and when I have enough I come here to see Delores. When she told me that she had taken you in and that you were available I raided the bank account and booked a night with you. Gladys is going to be pissed when she finds the money missing but you are worth it," he smiled at me cheekily.