Maid to Order Ch. 01

We came to a stop next to the fitting rooms. In this store they were unisex as the cubicles had floor to ceiling partitions and doors. She guided me inside past the counter where a bored looking assistant was sticking price tags on pairs of socks using one of those guns.

"No need to give the gentleman garment tags Miss Watson, I'm attending to him," she said officiously.

Karen Grayson, according to her nametag, was referring to the security tags that were issued to customers at the fitting rooms, one for each garment, to prevent shoplifting.

"This way sir," she guided my trolley to the far end cubicle.

Karen guided me inside the cubicle and handed me the black cocktail dress.

"One at a time sir, I'll pass them over to you," she smiled at me and pulled the door closed.

It finally dawned on me that Ms Grayson was helping me out. She was assisting me to try on my garments before I payed for them. I thanked the god of crossdressers and stripped to my briefs; I almost wish I had some knickers and a bra to put on before I tried on the clothes but I quickly realised I was being absurd.

Karen Grayson was true to her word and assisted me by passing the items over the door to me saving me untold embarrassing scenarios should I have attempted this by myself. I was going to be content with just taking them home and hoping they would fit; but being able to try them on in the store was a real windfall.

As it turned out everything fit perfectly, as best I could tell without foundation garments, except for the red gown.

"I think I need the next size up," I said in a hushed tone.

"Let me see?" she replied and brazenly opened the door and stepped inside.

It was cramped in the cubicles and although she wasn't fat; Ms Grayson was well built and her large breasts pressed against my back.

"Silly sausage, just stand still for me dear," she instructed.

Karen found the problem; I hadn't put the dress on properly and she pulled here and tugged there and suddenly the dress fell into place.

"Lovely; fits you perfectly," she slid her hands around my waist and smoothed out the fabric.

Then she pulled the hem down and smoothed it over my bottom. The feel of her breasts on my back, her fingers on my bum and the scent of her perfume was quite titillating and I began to become aroused and was glad I wasn't wearing panties after all. She turned me around and adjusted the bodice.

"It's supposed to be tight around here," she patted my chest.

"But once you put on your brassiere and fill the cups, and gaff this naughty fellow, it will fit perfectly," she gently squeezed by semi-erect penis through the dress and winked.

"Will that be all sir?" she smiled.

"I err, I err..." I stammered.

"You err would like my assistance at the checkout? Of course sir," she said and stepped out of the cubicle.

Dressed back in male attire she led me to the checkouts where she swiped a card that hung from a lanyard around her neck and opened a checkout just for me. She chatted about the weather while she scanned and bagged my purchases, ensuring the packaging was nondescript.

"Won't be needing these really will we sir?" she dropped the T-shirts into a large plastic bin marked 'returns'.

She swiped my credit card and I punched in the pin. She handed me my packages in a huge shopping bag.

"Thank you very much Ms Grayson," I beamed.

"You're welcome sir and its Karen," she winked at me and her fingers lingered and gently stroked mine as I shook her hand.

I floated back to my car and locked my purchases in the boot.

My last foray into the shipping centre was very successful. I purchased some lovely fully-fashioned stockings and three suspender belts at a specialty lingerie shop, explaining they were a present for my wife. Then using the same excuse I bought jewellery and other accessories at a costume jewellery shop and some perfume at a chemist. In the jewellery shop I had my right ear pierced; my left being already pierced in my youth. Last stop was a supermarket where I bought a good quality hairbrush, nailpolish remover, makeup wipes and other sundries, which I threw in with my weekly groceries so as not to draw any attention to myself.

I couldn't contain my exuberance and satisfaction on the long drive home; I must have looked like a lunatic, grinning behind the steering wheel.

As much I was tempted to play with my new purchases I locked them away, swearing to myself that I would stick religiously to my plan. When the rest of my packages were delivered to my post office box a few days later I was ecstatic; I couldn't wait for Friday!

When Friday afternoon arrived I raced home and closed up the house. I poured a hot bath and immersed myself in the bubbles and shaved my whole body from neck to toes and then I carefully shaved my face. My body tingled; I was not very hirsute in any event but the removal of all my body and leg hair felt so exhilarating.

I padded to the bedroom where I had laid out, but not opened all my purchases, displaying formidable constraint. I so wanted to slip into lingerie and try on one of my new dresses but I had made a pact with myself and kept it. I opened the cosmetics case and laid out the items I needed, carefully preselected once again using online advice. I opened a printed sheet of paper headed 'Makeup 101' and went to work.

I practiced applying makeup for the next three hours, using my online primmer and a few pictures of makeup models as my instruction book. This time my patience was rewarded and after a few miserable attempts I got better at it until I did a half-decent job. It was good enough for now anyway. I sprayed myself liberally with perfume.

I carefully applied red nailpolish to my toenails and fingernails and drank a glass of wine while it dried. Then I opened the boxes that had been delivered to my post office box and selected a black bob from the three wigs I had purchased. I was tempted to try them all on, one after the other, but I was getting impatient and I figured the black bob would work best with how I wanted to dress.

I opened the package containing my breastforms and was amazed at how realistic they looked and felt. They should do given the cost! The package contained surgical tape and theatrical glue and after fucking about for nearly an hour and after many failed attempts I finally had them attached to my chest and inside the C-cups of my red satin brassiere. It fitted me perfectly once I adjusted the clasps and straps.

Stepping into the red lacy suspender belt my cock had begun to harden I wished I'd remembered to purchase a gaff but I soldiered on (pun intended) and slid my freshly shaved legs into a pair of black fully-fashioned stockings. The sensation as I pulled them up my tingling flesh was indescribably decadent and my cock was now rampant. Pulling on my red satin panties and smoothing them snugly around my buttocks and groin was an experience beyond my wildest expectations; the satin caressed my freshly shaved scrotum and I used the tight panties to hold my engorged penis against my flat tummy. A little wet stain appeared in the front of my panties.

"Oh dear," I giggled, trying to sound effeminate.

Now came the part of the evening I had been looking forward to the most. I pulled on the red cotton-lycra blend, long-sleeved dress with less difficulty than I had in the changing room having been educated by the matronly Ms Grayson.

I made some adjustments and it looked stunning; it clung to my torso, my false tits giving it the perfect shape, flared at the waist with the hem coming to just above my knees. It felt absolutely wicked against my freshly shaved body and nylon-clad legs.

I accessorised with my jewellery, selecting gold rather the sliver as I had plenty of both.

Now the really difficult part.

I slipped my feet into a pair of high-heeled pumps, holding onto the dressing table for support. I brushed my hair again and carefully tottered over to the full-length mirror.

I was amazed at my reflection.

An attractive, tall, slender woman with fantastic breasts and legs stared back at me. The black bob, her eyes smoky with eyeshadow, eyeliner and mascara, her cheeks rouged and her lips ruby-red with glossy lipstick, framed her pretty face. The red dress clung to her body and then flared slightly at her trim waist, the hem caressed her stunning legs clad in sheer black fully-fashioned stockings and her feet shod in black patent-leather high-heeled pumps. The gold earrings, necklace, bracelets and rings perfectly accessorised the outfit.

"Oh my god Mick, you're fucking stunning," I blurted out.

"Nah, I'm not Mick, I'm Michele," I said in a falsetto voice that was going to take some work.

I paraded and posed in the mirror as long as I could before my arousal overcame my fascination at how good I looked. I relieved myself into one of my old stockings being careful not to stain my dress as I held the hem up and away from my groin, masturbating to my own reflection.

I spent the whole weekend locked in the house experimenting with makeup, trying on my various outfits and wigs, practicing walking in high-heels and talking in a smoky feminine voice. Oh and there was wanking, lots of wanking.

That was it! I was no longer a hairy panty-wearer. Michele had arrived!

Across town my father-in-law sat in his darkened study with the door locked, furiously masturbating to a streaming online video. In the video an attractive crossdresser was being rogered doggy-style by a fat middle-aged man and she was obviously enjoying it. The tranny and the admirer in the video and Bill in his den with trousers round his ankles all came together.

To be continued...