Michele Nylons' Stories Ch. 04

The next afternoon I could not get away from a working lunch with my colleagues which delayed my encounter with Lynn until mid afternoon. We met at my motel room and both dressed. Lynn wore only a little makeup in case she got an urgent call from work. She looked lovely in a full-length skirt with a side split, tight top, black hosiery and high heels. Her long blonde hair framed her elegant face.

For those of you now expecting the intimate details of two sexy Transvestites locking lipsticked lips together, sliding red nail-polished fingernails over bulging satin panties, intertwining sleek stockinged legs rubbing together and heavily madeup faces disappearing under skirts to swallow tumescent organs, I'm afraid I have to disappoint you; as much as I was disappointed myself. Despite my obvious desire to extend our platonic relationship further, Lynn was adamant that although there was the possibility of some intimacy in the future; it would not happen today. Lynn, honey I sure hope we will meet again and hopefully explore some that possibility.

We had another pleasant afternoon discussing all manner of subjects. It was lots of fun being dressed with another Transvestite but at the same time somewhat frustrating. Lynn left after about three hours, leaving me horny and frustrated. I was now determined that I would somehow arrange an encounter with someone. During the afternoon gabfest, Lynn had told me about how she often went out dressed as a woman and told me about some of the places that she had been to in drag. I have never been out in public dressed as Michele, but I plotted away in my devious mind and eventually hatched a plan that might work.

I showered, changed into drab, and went out for an early dinner. I did the rounds of the sex shop noticeboards and read the personals in the local papers but nothing had changed, there were no new contacts. I rang around my scant list of contacts with the same results as the day before; unanswered phones and answering machines. Ok, desperate times call for desperate measures!

I sat down and painstakingly painted my fingernails and toenails with the plumb coloured nailpolish. I let it dry while I sipped a glass of wine and watched the evening news then I opened the drawer and took out the three pairs of pantyhose that I had bought. I had stuffed two of them into the cups my brassiere when I had dressed yesterday and this afternoon. I could do better than that this evening though. I took the cheap pair of support hose and cut the legs from the panty. I filled the legs with rice, half a bag in each leg, and carefully knotted the stockings nice and tight. I kept pulling the stocking over itself and knotting it tight each time. When I had finished I had made a flesh-coloured ball that made a great substitute for a breastform. I did the same with the other stocking and now had two breastforms. (For you 'beginners' out there, this is a good way to make cheap but comparable breastforms.) I put them aside for later.

I shaved my face again very closely, showered and cleaned my teeth. I sat down to a really good job on my makeup. I applied a liberal amount of foundation and then coated my face and neck with finishing powder; the powder one shade darker than my foundation. I always do my eyeliner next. All of the makeup tips in books, magazines and online say you should do this later but I find, for me anyway, that this is the hardest part of applying my makeup and if I mess it up I can simply wipe it off, apply more foundation and start again without ruining my eye-shadow and mascara. I applied the eyeliner liberally to my upper and lower eyelids, from the inner corner of my eyes to the outer corners, gradually thickening the line.

I opened the small compact of eyeshadow and selected pale blue which I applied to my eyelids and then blended a shade of dark pink onto the upper part of my eye sockets and right up to my eyebrows. I could not pluck my eyebrows, but I shaved away a few rogue hairs; the fringe of my wig would come down to my eyebrows anyway. Next I rouged my cheeks to define the lines of my cheekbones. I always use more rouge and eye shadow than is the fashion nowadays but I like the 'heavy makeup' look and style of the eighties over the current subdued 'less is more' look.

I carefully brushed lashings of mascara onto my lower and upper eyelashes. I like to wear lots of mascara, and even though I was using a cheap generic brand, I managed to get my lashes thoroughly coated without clotting it. I took my time to apply the 'Lasting Colour' lipstick to my lips. I applied it carefully just outside of my lip-line so that my lips would seem fuller; the 'Raging Ruby' lipstick set off my plum red nail polish nicely. I finished with another coat of face powder.

I went back and sat on the bed and pulled on a pair of taupe sheer to the waist pantyhose. If I wear pantyhose instead of proper stockings I always wear them underneath my panties for a number of reasons. One: I like the look of panties over hosiery, two: pantyhose hold my genitals tight against my body and help prevent that tell tale bulge, and three: I love feel of sheer nylon on my genitals.

Next I pulled the peach coloured, boy-leg, panties up my legs and snugged them around my buttocks. The silky feel of the satin panties on my hosiery was exquisite and I couldn't help but gently stroke my satin encased member for a few seconds before I got back to the task at hand. I pulled on the brassier and stuffed my makeshift breastforms into the cups and adjusted it. I slid into the mauve satin blouse and buttoned it up. I steeped into the navy blue skirt and pulled it up, zipped up the side and adjusted it at the waist so that it sat properly. The hem came to about six inches above my knees and it had nice little split at the back that showed off more of my legs. Finally, I pulled at the satin lining off my legs where it had clung to my nylon stockings.

I sat back down on the bed and slipped on the faux crocodile skin high heels. I had been lucky and they were a good fit. They didn't exactly match my outfit; I would have preferred black pumps, but I had to get what I could take in my current circumstances. I opened the wardrobe and took out the wig from its makeshift wigstand. I brushed it out and moved in front of the full-length mirror. I always look a bid ridiculous fully made-up and dressed as a woman without a wig. but as soon as I put the wig on my head the transformation is amazing. I adjusted the brunette bob so that the fringe just covered my eyebrows and the hair was evenly distributed around my shoulders.

I wished I had thought to buy some cheap junk jewellery but I hadn't, so I took off my signet rings and necklace. I took the pendant off the neck-chain and then hung the gold necklace back around my neck; at least it was something. I checked myself in the mirror again. I sprayed perfume liberally on my décolletage and a also gave quick spray under my skirt.

And there I was. Michele Nylons in all her glory; a heavily made-up Transvestite tart looking for sex in the city!

So now I had to muster up the courage to do what I had never done before; go out into the world dressed as Michele.

It was now about 8:30pm and quite dark out. I looked at myself in the mirror and convinced myself that I could pass as a woman. To be fair I think I can pass as a woman from a distance, but up close, even though I think I'm attractive, it is still obvious that I'm a Transvestite. I picked up my keys, cell phone and wallet and then realised I didn't have a purse or any pockets to put them in. I put my cell phone and wallet in a plastic bag; it would have to do. I had parked the car right outside of my motel room door and I peeked out of the blinds to see that the coast was clear and then quickly went outside and got in behind the wheel of the car.

It was exhilarating just walking the few steps to my car. I loved the sound of the clatter of my heels on the parking lot and the feel of the cool evening on my body. I was still nervous as hell though and adjusted the switch on the dome light so that it stayed off when the door opened. I flicked off my high heels because the last thing I needed was for my heels to slip on the accelerator or brake. Although I would love to be rear-ended tonight (get the pun?); I did not want to get involved in a rear-end collision with another car. I threw the plastic bag containing my cell phone and wallet into the glove compartment and started the car.

I carefully navigated my way out of the driveway and onto the main road; God I was so nervous, but so excited! When I stopped at the traffic lights I was sure that someone was going to look at me and start laughing; but of course that didn't happen. I would like to think I actually got a few admiring glances from some of the male drivers but I was really too nervous to notice.

I pulled up outside of the dingy sex shop that I had reconnoitred the day before. So now you see my plan? I figured this was just the sort of place that a girl like me might be able to pick up a guy who might like a girl like me!

I took the keys out of the ignition and locked the glove compartment. I opened the car door and walked to the door of the sex shop; the street was deserted which actually disappointed me now that I had finally summoned up the courage to go out dressed. When I walked through the entranceway the bell went off to signal the clerk that someone had entered his store. I half expected to be greeted by a sea of enquiring faces when I walked into the shop but was again disappointed to find that the shop was deserted except for the clerk.

The clerk gave me a quizzical stare and then a look of recognition crossed his face. I had been 'clocked' (a term used by transvestites who pass themselves off as a woman when they are found out to be a man). He smiled and said,

"Good evening," and then went back to his TV show.

I was disappointed that the store was empty, but reality seldom lives up to the expectations of a vivid imagination; I don't even know why I thought this dingy shop would be full of sex starved Admirers. I decided that I would stick around and see what eventuated and wandered up and down the aisles browsing looking at the pornography and sex aids. The clerk looked up from his television every now and then but didn't seem too interested in me. I was toying with the idea of trying to engage the clerk in conversation when I heard the doorbell go off.

A couple walked in and browsed the DVD display before selecting one and taking it to the cashier. They glanced over at me a couple of times, whispering and giggling occasionally. I reddened and began wondering what the fuck I thought I was doing being out dressed in drag but I held my resolve and I stayed in the store after they had left. A couple of minutes later two men came into the shop and made their way to the magazine stand and chatted away as they perused the selection. They looked over at me but neither made comment or made any attempt to engage me in conversation.

The clerk looked over at me again and I was considering moving on; I had been in the shop for about twenty minutes now and I thought that before long I was going to be asked to buy something or leave. Then a single man entered the shop. He looked around and did a double take when he saw me. He smiled and walked over to the contacts noticeboard. I didn't know if his smile was one of appreciation or disapproval. There was only one way to find out.

I walked over to the noticeboard and stood close to the man. He looked to be in his early fifties and was dressed in denim jeans, a western shirt and scuffed boots; he smelled faintly of tobacco. The man was about two inches taller than me and a small hard beer-gut strained the buttons of his shirt. His thin sandy hair was shoulder length and needed washing and styling. Hardly a great catch but he was what some would call 'rough trade'.

He continued looking up at the noticeboard and murmured,

"Seen anything here that interests you?"

"I've tried to phone the contacts up there who interest me and I've done no good," I responded.

I do not have a feminine voice and I have not tried to develop a phoney feminine whine. When I'm playing at being Michele I try to make my voice sound raspy and put on a bit of a phoney British accent. It is not a very feminie voice, but it sounds sexy and sort of smoky, at least to me. Regardless of the sound of my voice or how I looked it must have been obvious to him that I was Transvestite.

The man turned his head away from the noticeboard and looked me up and down and then replied,

"You take MY interest," and smiled.

The man was not handsome not ugly either; he was rugged and a bit loutish; he was "Mr Average"; the sort of man that I sometimes find myself quite partial to. I smiled back and picked up one of the pieces of paper off the shelf fitted to the bottom of the noticeboard. I wrote my cell phone number on it and handed it to him. He glanced down at the note and then looked up at me.

"When?" he asked, raising his eyebrows.

"Tonight; now if you like?" I responded nervously.

"Ok," he responded and nodded towards the door.

"I'll leave now and wait for you outside," and then he walked away and out the door and into the night.

My heart was beating like a trip hammer; I was nervous, scared and excited all at once. So far I had only given the guy my phone number; I could still get out of this. But my excitement overcame my fear. I looked around and I saw the other two customers talking to the clerk at the counter; they looked my way, said something to the clerk, and then they all started laughing.

I set my resolve, spun on my high heels and walked outside into the night.

I walked straight to my car and got in, my heart pounding. As I fumbled with the lock on the glove compartment my mobile phone started ringing.

"Fuck!" I mumbled, springing the catch on the glove box, snatching my phone out of the plastic bag and I looked at the number on the display. It was a cell number that I didn't recognise; I hoped it was him.

"Hello," I whispered into the handset.

"You sitting in a white Ford Taurus outside of the sex shop?" a male voice asked.

"Yes; my name's Michele," I answered.

"Nice name love; mine's Robby; are we on?" he asked.

"Yes, you can see me sitting in my car I take it?" I answered.

A beat up utility (pickup truck) parked diagonally cross the road from me flashed its lights twice.

"You see me?" Robby asked.

"Yes honey; I have a motel room just down the road (I gave him the name of the hotel but not the room number), you want to meet me there?" I responded.

"Sure. Now?" he replied.

"Yes if you want to. Just give me fifteen minutes and then park on the street near the motel. Call my cell and I'll give you my room number ok?" I told him.

"Sounds good; just one thing though?" Robby sounded excited now.

"What?" I enquired

"How much?" he asked.

I laughed into the phone and then stopped myself. I didn't want to scare him away.

"I'm not a professional honey; I do this for fun," I used my smokiest voice, trying to sound sexy and alluring.

"Even better; see you in fifteen then," he hung up.

I kicked off my heels and drove back to the motel and parked as close to my room as possible. I made my way inside exhilarated by my accomplishments. Not only had I been out for the first time dressed as Michele; I had picked up an Admirer. I quickly went into the bathroom and fixed my makeup; a bit more blush and powder and another coat of lipstick. I sprayed more perfume on my neck and another quick spray under my skirt and then went out and adjusted the lights so that the room was dim. As I poured myself a glass of wine my phone rang. The call originated from the same number that had called my in the car.

"Room eleven ok?" I murmured into the handset.

"See you soon," Robby answered and broke the connection.

There was a soft knocking on my door about thirty seconds later, Robby was wasting no time. I pulled the blind aside a smidge and looked out; it was him. I opened the door and he walked inside and stood awkwardly in the centre of the room. I locked the door and walked over to where my wine glass sat on the glass-topped table and sat down. Robby sat down opposite me and looked around nervously. He reached into his shirt pocket and took out a packet of cigarettes.

"Do you mind?" he inquired, holding out the cigarette packet.

"No. Not at all. Can I have one?" I countered.

He offered me a cigarette and I saw him staring at my nailpolished fingernails as he lit it for me.

"I like girls who wear nailpolish and lots of makeup," he muttered around his cigarette.

I decided to break the ice.

"Have you been with a Transvestite before Robby?" I asked.

"A couple in Sydney; mainly pros, I also picked up one at a bar in Kings Cross when I was younger and she took me home and I spent the night. I like trannies but we don't get them around here much," he went on.

"Well, what about if I tell you about what I will and won't do and then we can take it from there ok?" I replied.

"First off; I love to kiss and cuddle. You can touch me anywhere you like but tonight you can't penetrate me. I like oral and will go all the way to completion; you can pull out if that's what you like but I do swallow. I'm pretty much up for anything tonight except you can't fuck me; and I remain dressed at all times ok?" I decided to be frank and get the ground rules out of the way.

"Sounds good to me; can we start now; I've only got a couple of hours before I have to be home," he answered.

"Sure," I replied stubbing out my cigarette and draining my glass.

I stood up as he butted out his smoke. He walked around the table and grabbed hold of me, wrapping me in his strong arms and kissed me forcefully, his tongue snaked into my mouth and I felt his cock harden against me through his tight denim jeans. I slid my hand down and rubbed the hard bulge in his trousers and he groaned in my mouth. Robby was rough, but he was just what I wanted after being without a man for so long.

I pulled my face away from his.

"Let's got over to the bed," I said, taking his hand and leading him towards the queen sized bed.

Robby walked slightly behind me and he slipped his free hand under my skirt and stroked my buttocks.

"You naughty boy," I joked, and pulled him back towards me and I kissed him again and as my tongue slid into his hot wet mouth I lifted my leg and crooked it around his and rubbed it up and down.

"Fuck you're a horny slut aren't you?" he joked, "Lets me get undressed to I can enjoy this properly."

I eased out of his embrace and unbuttoned and removed his shirt. I kissed and licked his nipples briefly and reached down and unbuckled his belt and undid his fly. I dropped to my knees in front of him and reached up and pulled his jeans down around his ankles. I reached up again and pulled down his jockey shorts. A musky aroma escaped his groin and filled my nostrils. His cock was thick veiny and uncircumcised. He was aroused but not yet fully erect. I would fix that!

Still on my knees I reached out and lightly took hold of Robby's semi-hard penis and slowly stroked it. I let my fingers slide feather-soft along the shaft and then when they got to the end of his manhood; I eased his foreskin back exposing the shiny purple knob, and I gasped at the strong musky odour that was released from his exposed glans. Robby groaned and pushed his groin out from his body, encouraging me to keep up my ministrations. I looked up to see him looking down at my painted face; he was smiling.

"You know what I want," he moaned encouragingly and reached out and placed a hand on my head and pulled my face towards his groin.

"What about getting undressed?" I teased and held my face inches short of his now rampant cock.