Chapter 4

This is a continuation of my True Stories series, where I tell my readers about my real life adventures as a part time Transvestite. In this instalment I will tell you about my most recent encounter; my first encounter for some time, and also for me a milestone; my first time out and about dressed as a Transvestite.

As most of my readers know, I live in Australia and used to travel extensively with my job. My work situation greatly assisted my life as a closet Transvestite because I maintained an apartment in a different city from where my family home was and used that apartment for Michele's girly activities. My circumstances had recently changed. Due to an upheaval at work, I was recalled to the head office. In short, I am now living back in my family home and this situation leaves me with few chances to dress up and scant chance to play.

I currently have all of my feminine clothing, wigs, makeup and lingerie in long term storage where it is not easily accessible. I had been in withdrawal from dressing for so long that I would have done almost anything to transform into Michele, even for a couple of hours; but I just couldn't arrange it!

You read all the time about Transvestites and Crossdressers who attempt to give up their lifestyle and vowing never to crossdress again, and then they are so overcome by the urge to dress that it becomes irresistible. I believe this 'urge' is the difference between the true Transvestite and the 'part-time panty wearer'. In the past, for various reasons, I have attempted to give up my life as a part time Transvestite but this time it was different, I was being forced to give up being a Transvestite when I didn't want to give it up! Then an opportunity to transform into Michele and play my seductive games came along. I have often found in my life that there is much truth in the axiom: "truth is stranger than fiction", and this was certainly the case last month.

For those of you who don't believe this story is true, I hope you enjoy it anyway. For those of you who know me, and there are a few readers out there with whom I have met; you will know that this is indeed one of Michele Nylons' – True Stories.

I received a phone call from my employer directing me to travel interstate to a large regional city to attend to some urgent business. I would be there over a few days and I figured I would have plenty of time to play at being Michele as well as meeting my work obligations. My dilemma was that because of the short notice I didn't have time to get hold of the clothes, wigs and makeup etc that I had hidden away in storage. I would just have to get hold of whatever I needed when I got to my destination.

When I arrived, I was pleasantly surprised at the accommodation that my firm had booked me. It was a self-contained unit in an up-market motel, quiet and inconspicuous with parking right outside my door; the perfect place for a closet Transvestite to ply her trade. I had rented a car, and as I had been in this city a few times before, I knew my way around. The first day I was there I attended to my business but my thoughts kept wandering off to what I was going to get up to after work. Declining offers from my business associates of going out for drinks and dinner later that evening, I departed the meeting as soon as possible early in the afternoon.

I had spied an 'Opportunity Shop' (second hand clothing shop) near my motel and drove there straight away. Being midafternoon on a weekday, there weren't many customers there and I pretty much had the place to myself. I have bought women's clothing in stores like these many times and have found out that rather than skulking around the ladies apparel or invoking implausible stories for the clerks, it is best to just be confident and brazen and mooch through the women's clothing section, selecting whatever takes your fancy and more importantly clothing will fit and will look good on you.

A lot of closet dressers just take larger size clothes off the rack, thinking that the clothes will fit them and they don't take into account what the clothes will look like on them. I have a definite 'look' that I like to achieve, it's sort of a slutty secretary look (you can see me dressed that way in my profile picture and on the many websites on which I post pictures of myself) and I try to get clothes that match my 'look'. There is no fun for me traipsing around in a frumpy patterned house-dress two sizes too big, wearing clunky shoes, a bad wig and a with a laughable makeup job. To me there is a lot more to crossdressing than just being a "bloke in a dress". I'm not knocking those out there who just like to play 'dress-up', but I have my own standards.

The other thing that makes me cringe is that a lot of the stories posted on this site describe how some middle-aged guy suddenly gets the desire to crossdress (or is forced to crossdress), and then just hops into some lingerie, stockings, high-heels, makeup and a wig, and transforms into a gorgeous looking femme-fatale; what a load of bullshit!!! Transvestites and crossdressers know that it takes quite some time and effort to transform from a man into a convincing looking woman. Anyway; I digress.

I quickly went to the ladies clothing section and after mooching through the racks of clothing I selected a nice navy-blue skirt and a mauve, long-sleeved blouse. It helps if you know your sizes (I am an Australian size 14 but can sometimes squeeze into 12 ... and no I'm not fat! I have a big frame; I take a size 10 ladies shoe) but as with any clothing, male or female, sizes vary. I couldn't try on the skirt in the shop but I checked it against my waist and it looked right; the blouse looked like it would fit but I slipped it on over my T-shirt to make sure. Next I needed shoes.

Another thing that I have found out about shopping at 'Op Shops', is that they do tend to carry a lot of larger sizes. I believe this is because the stores are there to cater for the less financially fortunate, and they often tend to be larger women. I'm not being in any way condescending, it's just a fact. Anyway I spied a lovely pair of faux crocodile skin high heels in my size and added them to my purchases and made my way to the counter.

The register was staffed by an elderly lady and I was forearmed with the usual bullshit story about how the clothing was for me for a fancy dress party, hardly believable and unlikely to convince her, but who gave a fuck? She was probably used to guys coming into the store and buying women's clothing anyway. As it turned out she didn't bat an eyelid and just rang up my purchases, gave me the change and wished me good day. I had made a good start on my forthcoming transformation, and at a bargain price.

The next step was easy; I dove to a large "Big W" Woolworth's department store to buy my lingerie. I would have loved to have gone to a specialty shop to buy a nice garter belt and matching underwear, but I had neither the time, inclination, nor the money; you can get good quality budget lingerie at department stores anyway. I selected a pair of peach coloured satin, boy-leg panties with the matching bra and two pairs of good quality, sheer to the waist, pantyhose and another cheaper pair of support pantyhose. Again I was forearmed with the usual bullshit story of "buying lingerie for my wife" if confronted by a salesperson or at the cash register, and again I didn't need it. Although I didn't know that many people in this city, I did scan the registers to make sure that none of my business colleagues were around and I made sure I got in a small queue at a register staffed by a middle-aged lady.

I dumped my purchases back in my hire car and went back into the shopping centre to a shop called "Loose Change". I have shopped in this chain store many times because they sell cheap makeup and the cosmetics section is unattended. It IS difficult trying to explain to some snotty, condescending cosmetics saleswomen why you are buying makeup and even harder to disguise your expertise when selecting cosmetics; so I tend not to buy my makeup at the well-known department or specialty stores unless I have to. Also I find that the makeup at department stores and chemists is overpriced.

I selected foundation, finishing powder, blusher, eyeliner, mascara and a small compact of eyeshadow containing several colours. I also picked up a makeup brush, some plumb coloured nailpolish, a bottle of cheap perfume (the generic sort of: "I can't believe it's not Poison" sort of product that these cheap stores specialise in), and a bottle of nailpolish remover and liquid moisturiser. I can rave on again about stories written where some guy just gets the urge to crossdress and sits in front of his sister's, mother's, or wife's (pick one) vanity mirror and manages to put on a magnificent sexy female face without any previous experience with makeup or any attempt to match the makeup to his complexion; but I won't!

I payed for the makeup at a cash register manned by a bored, gum-chewing, teenager who took absolutely no interest in my purchases and looked like she would rather be anywhere else in the world but at work. I dumped the makeup in my rental car and made my way to the supermarket. Why do I keep going back to the car with my purchases you ask? Well as much as I have no real fear of sales assistants asking me why I'm buying women's clothing and necessities (except for snooty cosmetics saleswomen of course); I do not want to be caught in the position at the checkout where I have to present my bags for inspection as most shops now require. I'd rather not explain to some officious bint with a superiority complex why I have in my possession bags full of lingerie and makeup; it's just fucking easier to not have the hassle!

At the supermarket, I bought some essentials and food and drink. I also purchased a half-kilo bag of rice and at the cosmetics section (again, unstaffed but outrageously expensive) I selected a tube of Max Factor, Lasting Colour Lipstick in 'Raging Ruby'. At twenty dollars, it was the most expensive single item I had purchased so far! Although I usually buy cheap makeup, I always buy expensive, good quality, long lasting lipstick (most of you can guess why). I payed for my purchases and made my way to my car to think about how I was going to solve my major problem; where the fuck was I going to get a decent wig?

In many of the stories and articles I have posted online, I have emphasised the importance of wearing a good quality wig that matches your 'look'. When I first started dressing I went to Oxford Street in Sydney and sought the advice of a professional before trying on and then buying my first wig. (Oxford Street is the gay section of Sydney and home to the 'Gay Mardi Gras', hence it is not unusual for men to go there to buy wigs and other girly requisites) So; I knew what I wanted, but did not want to pay the two to three hundred dollars it costs for a decent wig; especially when I had a couple of good wigs in long-term storage.

I also didn't want to buy a cheap, fancy-dress wig that would look silly and unconvincing. I stopped at a drive-through liquor shop and bought some wine on the way back to the motel. I took my purchases inside, poured myself a glass of wine and ruminated on my problem. I looked through the Yellow Pages at the scant few advertisements for wig shops when a brainstorm hit me. On the same page which listed the only two specialty wig shops were advertisements for fancy dress and costume hire outlets. Fuck! What great idea!

I went back to my car armed with the page torn out of the phonebook and drove to the nearest costume hire place. As I had hoped there was a large selection of good quality ladies wigs for hire. This time I DID have to use my bullshit fancy dress story on the lady behind the counter. I paid twenty dollars for two days hire and left an additional twenty dollar deposit on a lovely brunette bob. Now I had everything I needed to transform into Michele; if only I could rustle up some company to spend some time with I would be in heaven!

The obvious place to look for short-term sexual contacts was the noticeboards in the few sex shops scattered around the city. As I had been to this city before I hit them one after the other, writing down the phone numbers of potential contacts on the slips of paper provided. The sex shops in this city ranged from a well-lit overpriced chain store called "The Adult Shop" to a small, dark and dingy, sticky carpeted edifice that was only three blocks from my motel. As well as collecting the contact phone numbers I also picked up a couple of pornographic magazines, just in case I couldn't arrange a meeting.

It was now late in the afternoon, too early to call the contact phone numbers I had collected so I decided to check my email and write up a report on the first day of my business meeting. I went back to the motel and took my time unwrapping all of my purchases. I was like a kid unwrapping Christmas presents. I laid out all of my toiletries near the washbasin in the bathroom and I put my makeup into the empty toiletry bag. I hung up the skirt and blouse and put the high heels below them in the wardrobe. I unwrapped the pantyhose and put them in my underwear drawer with the panties and bra. I brushed out the wig, draped it over an upended empty vase and put it away on the back of a wardrobe shelf and obscured it using a spare pillow. (The trick of using an empty vase as a wig-stand is one I have used for years). I put all of the packaging in a plastic bag and took it outside and dumped it into a large rubbish bin. The idea was to have all of my female accoutrements at hand but hidden from unexpected arrivals and the housemaid (hopefully if the housemaid finds any of the female attire except for the wig she will just think I have woman staying here ... but do I really give a fuck what the housemaid thinks!)

I poured myself another glass of wine, fired up my PC and went online. As usual, unless I am at work, the first thing I did was to log into msn messenger as michelenylons at msn dot com (see what I did there; I give you my msn email and messenger address without putting the URL in the text of this story). What happened next is the part of this that some of you will find hard to believe. I write a lot of TG fiction so there is no need for me to "invent" a storyline for my True Stories.

Lynn is a tall, slim, strikingly attractive mature TV. She is one of the few TVs over thirty I have met who can wear a long, straight-haired, blond wig and not only get away with it; but look absolutely stunning. I think this is because she is so tall and slim and because she makes the effort to wear clothes that fit her so well and takes advantage of her figure and height. Lynn was online. Lynn was willing to chat in Messenger. Lynn was in here in her home town!!!

I should explain that I have chatted to Lynn on numerous occasions and even though we have mutual TV friends (Tracy and Vanessa). I have, in the past, come here to her hometown and she has sometimes visited mine, but we have never been able to meet up for one reason or another. So there is the coincidence, which some will not believe, but is true regardless. Lynn and I are both in the same city, both online, and both prepared to meet.

I know from my many exchanges with Lynn that she is a very cautious TV, but once she gets know and trust other TVs and CDs she will meet up with them and will even go out socially with them whilst dressed. She is not into Admirers and seldom has sexual encounters, even with other TVs.

We chatted online for a while, both delighted that we were in a position where we could finally meet. It was particularly fortuitus that I had my motel room and that I was travelling alone. She was willing to meet me and I agreed to a rarity for me; I agreed to meet in drab! I hardly ever meet in drab, and certainly have never, nor would ever, meet an Admirer in drab. By necessity I have often met up with other TVs in drab, but we have quickly changed into our female alter-egos. Today I would be meeting Lynn in drab and remaining in drab. She just wanted to meet and talk to see how we got on before taking the relationship any further. See what I mean about her being cautious! We exchanged cell phone numbers and I called her and gave her my address.

We met in my motel room later that afternoon, drank coffee, and talked about our lives as closet TVs. Lynn also has a partner and has to very discreet. Unlike me, who is cautious but at the same time promiscuous, Lynn is vary careful about not only who she meets, she seldom gets involved in sexual activity. We discussed all manner of TV related topics and it was pleasant, if unusual to be dressed in drab, to talk to another TV about cosmetics, other TVs, sex, clothes, snotty cosmetic saleswomen and other TV related gossip. We agreed to meet again the next afternoon as we could both get off work after lunch.

Being the way I am, I couldn't wait for tomorrow to dress up and hopefully have some girly fun; I wanted some action tonight! After Lynn left I tried calling the half dozen contact numbers I had got from the notice boards in the sex shops. They were either not connected or rang out and one went to voicemail. I had struck out! I debated calling a male prostitute or a Transsexual escort as I have used their services in the past with various degrees of satisfaction. There were only two Transsexual escorts listed in the personal section the local paper and I decided to give them a try. I have had some wonderful experiences with Transsexual prostitutes, but a lot of Transsexuals (the majority?) don't have much time for Transvestites. Again I struck out; one call went to voicemail where I was informed "Amanda is out of town for two weeks," and the other girl wanted nothing to do with a Transvestite; I could only make an appointment to see her if I came to see her as a male.

Fuck it! I decided I would dress as Michele and have some solitary fun tonight and hopefully I could have some girl on girl action with Lynn tomorrow.

I closed the curtains, hung the 'Do Not Disturb' sign on the door, stripped naked, turned on the lights and looked at myself in the full-length mirror. I had certainly let myself go as far as keeping myself free of hair body. Because I hadn't dressed for so long and because I didn't think I would get the opportunity to dress for some time I hadn't kept up my strict depilatory regime. I hadn't bought my beard trimmer (an essential tool for any part time Trannie) so I would have to make do with what I had.

I got the shower running nice and hot and soaked by body for a few minutes to get my skin supple. Shaving my legs was easy but time consuming, I had to rinse the razor continually to clean away the hairs. I couldn't do too much with my genitalia except to trim back my pubic hairs; as for my buttocks and arse crevice, they would have to remain hairy as I had not bought depilatory cream (I didn't really think I would get myself fucked anyway so it wasn't that important). I shaved my hands, fingers and wrists. My arms only have light hairs on them and I always wear long sleeves anyway. My chest and neck got a shave as far down as my décolletage (Curly hairs protruding from a blouse is unsightly and decidedly unfeminine). That was the best I could do for now; but at least all of my exposed body parts would be hair free when I was dressed en-femme.

I won't bore you with the details of the rest of the evening except to say that finally dressing up as Michele again was exhilarating. The silken feel of my lingerie, the whisper of my skirt hem against my stockings, the clatter of my high heels on the tiled floor and the taste and smell of my makeup and perfume were memories well recovered. By the end of the evening I had put my recently purchased pornography to good use even though the most intense climax I experienced that night was while I masturbated looking at myself in the full length mirror. After a pleasing but not particularly satisfying evening of self gratification I cleaned off my makeup, put away my feminine attire and showered before going to bed and dreaming of Lynn.

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.