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.

 

True Stories

by

Michele Nylons

Part IV

      

This is the story of my latest encounter, which took place only last month. 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.

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.

"Come on; you can finish me off now and I'll be able to get another one in before I have to go," he pleaded.

I was as excited as he was and my penis was expanding inside my pantyhose and becoming quite uncomfortable. I had to put my free hand under my skirt and adjust it inside my panties. It had been so long since I had taken a cock in my mouth that I was as impatient as Robby to continue.

I stroked Robby harder now, my grip tightening on his hard phallus. I could feel his veins and through the sleek skin covering his rock-hard shaft contrasting with the spongy meat of his glans. A thin stream of clear pre-seminal fluid escaped the eye of his penis and I worked the lubricant into his cock as I masturbated him. Robby rocked back and forth on his heels and the hand he had placed on my head was pushing my face harder and harder towards his groin. I lifted my free hand to his scrotum and gently massaged his testes. Robby was groaning quite loud now.

"Come on Michele; suck it honey. Suck it before I come!" he pleaded.

I allowed him to guide my face onto his penis and I extended my tongue and licked the tumescent weapon just before it pushed against my lips. I opened my mouth and closed my lipsticked lips over Robby's cock and he pushed it further into my wet mouth. My nose came hard up against his groin as he filled my mouth with his cock. He bought his other hand down and placed both his hands on the sides of my face and held my head still and he began to fuck my mouth.

Robby's cock was not the biggest cock I had taken, but it was nice and thick and I had to time my breathing around his thrusts. The pungent aroma coming from his groin was nearly overpowering and the feel of his cock inside my mouth and his silky scrotum in my hand created contrasting sensations, which I savoured. I allowed Robby to fuck my face.

I looked up with my dark, mascaraed eyes and saw him looking down at me as he raped my face. He was staring intently at my heavily madeup face, watching as his cock slide in and out of my lipsticked lips. His gaze wandered to my stockinged calves and over my high heels and then back to my cock-filled face.

Robby smiled down at me and groaned.

"Oh fuck this is good, I love Trannies and it's been a while since I fucked one. Fuck I'm going to blow soon!"

As Robby pushed his cock faster and faster in and out of my mouth I had to concentrate on breathing. He was pushing my face right into his groin when he thrust forward, and I adjusted my breathing so that I could inhale on his backstroke. I knew he was about to orgasm and prepared myself for the flood of semen I was about to receive. The way he was pushing my face into his groin, I doubted he was going to pull out so I knew I would soon be swallowing his seed.

Contrary to most descriptions of fellatio, you can't actually feel the spurts of come as they erupt from the head of a penis inside your mouth. What you feel is your mouth fill up with warm musky fluid, the volume of which largely depends on when the donor had their last orgasm and how aroused they are at the time of climax.

I was not disappointed when Robby held my head in a vice like grip and thrust his hips back and forth, spewing a great flood of semen into my mouth. I swallowed his issue each time that he filled my mouth, and lashed my tongue around his member to coax the last drops of spunk out of his pulsing member. Robby was moaning and howling as his orgasm shook him and I hoped that the occupants of the adjoining rooms could not hear.

"Oh fuck yeah baby; of yeah, suck that cock, swallow that load. Oh fuck, suck me, suck me, suck me!" he screamed at the height of his climax.

Gradually, Robby released the grip on my head and I could breathe easier and I licked and suckled his deflating penis until he pushed my face away.

"Honey that was lovely; but it's too tender for you to suck on it any more."

Robby reached down and pulled me to my feet and took me in his arms and kissed me deeply. His hands clasped my buttocks and he pulled my lower body hard against him. He whispered in my ear.

"Mmmm I can feel your hard cock through your skirt so you must have liked it. Now if you finish undressing me and get me a drink and a smoke, I might get it up again soon and I can take care of you as well as me again," he eased me out of his embrace and sat on the edge of bed.

He reached down and started to remove his boots and then looked up at me.

"Well honey, don't just stand there; go and get the durries and the booze!" he laughed and smacked me playfully on the behind.

I went into the bathroom first and fixed my makeup. Robby's tempestuous face fucking had removed most of my lipstick, and makeup from around my mouth and nose. My wig was slightly slanted and I adjusted it to get it to sit right with the fringe straight. I reapplied foundation, powder and lipstick and quickly brushed my teeth. Although Robby had kissed me after fellatio, I know that some men don't like to kiss girls after they have ejaculated in their mouths.

I was delighted that Robby was being playful and showed a willingness to stay after he had climaxed. Some guys get 'post coital regret' after they come and can't wait to get away. They feel ashamed that they have had sex with a Transvestite and get all homophobic, but that definitely didn't seem to be the case here.

When I came out of the bathroom to go the kitchen-diner to get the cigarettes, ashtray and the wine I had to squeeze past Robby who was standing naked just outside the bathroom door. He grabbed me as I walked past and pulled me roughly into his arms. He kissed me hard, his tongue slithering around in my mouth. His hand went under my skirt and slid over my satin encased cock and it slowly hardened in my panties. I humped against his hand and he laughed and pushed me gently away.

Robby's harsh face softened when he smiled and he spun me around and patted me on the buttocks as he guided me towards the kitchen-diner.

"Get going and get the drinks and ciggies Michele; before you get me all fired up again," he laughed.

While I poured wine into two glasses and lit two cigarettes I heard Robby pissing into the toilet bowl, followed by a flush and the sound of running water in the hand basin. When I returned to the bedroom I found that Robby had hung his jeans and shirt over the back of a chair and he was lying under the covers in the bed with his head propped up on a couple of pillows. He had turned on the TV and was watching a cop show.

Robby smiled up at me and patted the bed beside him. 'I could really get to like this guy,' I thought; he reminded me a lot of Buster, a 'regular' of mine who used to visit me when I had my own apartment.

I walked over to the bed carrying two glasses of wine; one in each hand; and the now clean ashtray tucked under my arm. To save a trip back to the kitchen-diner I had put both lighted cigarettes in my mouth.

"You look like a real trollop with those fags hanging out of your mouth," Robby laughed.

"Well after what I just did for you, you know I am," I mumbled around the cigarettes.

Robby reached out and took one of the cigarettes and a glass of wine and leaned back against his pillows. I put the ashtray and my glass on the nightstand and scooted onto the bed so that I was lying on next to him top of the covers. My heel caught the coverlet and as I kicked it free my skirt rode up. I attempted to pull the hem down when Robby reached out and smacked my hand.

"Leave it; I like what I see," he ordered, and smoothed his palm along my nyloned thigh.

"Ok," I laughed and reached out and took my glass, sipping my wine and smoking my cigarette.

Robby smoked his cigarette and sipped at his wine, intent on the cop show on TV. His hand continued to stroke my thigh and I was slowly becoming aroused. When I had finished my wine and cigarette I turned sideways and snuggled against Robby. His hand stayed on my thigh and continued to absently stroke my gauzy pantyhosed legs as he watched TV. I reached out stroked his hairy chest with my red nailpolished fingers.

We lay like that for about fifteen minutes until the cop show finished and then Robby abruptly turned off the TV with the remote and turned to me and said,

"Now where was I? About here if I remember rightly," and his hand slid over my tight, panty-encased cock.

I moved against him and kissed him deeply and slid my hand under the coverlet to find his hardening penis. Our kisses became hotter and harder and his hand stroked and grasped at my thighs, crotch and buttocks. He pulled at my panties until his fingers got under the waistband and found my pantyhosed encased cock. He wanked it though the sheer nylon and I moaned in his mouth and reciprocated by pulling on his now fully erect manhood.

Robby rolled out of the coverlet and deftly climbed over my prone body so that he was straddling me. He pushed my shoulders down into the bed and raised his body up over mine and looked deeply into my eyes.

"Fuck you look good," he groaned as his eyes looked up and down my body, retuning once more to meet my gaze.

Then he lowered himself on top of me, resting on his elbows; he kissed me hard, pushing his lower body down into mine. I wrapped my arms around him and kissed him back and pushed my body up against him. Robby stroked my face as he kissed me and then I felt his hand move away and push between our bodies.

Robby hitched up the front of my skirt and he wriggled on top of me until his hard cock rested against mine. Through the material of my satin panties and my pantyhose I could feel the heat of his member against mine. Robby rubbed and pushed against me, dry humping me. The friction of the satin and nylon against my penis was exquisite and I bucked up against him to increase the stimulation. I knew I would come soon if I didn't control myself.

I reached down between our bodies and took hold of Robby's tumescent member and opening my legs slightly, I pushed it down so that it was trapped between my silky hosed thighs and the satin gusset of my panties. Robby responded by pushing himself in and out of the gossamer love tunnel that I had created for him between my legs. The feeling of his hard cock on my thighs and crotch was stimulating, but not orgasm inducing. Robby smiled into my face.

"You know a few tricks, you dirty whore," he giggled.

I responded by humping myself harder against him, increasing the sensations for him. Robby continued to rub his cock against my thighs and crotch for a few minutes to raining hot kisses on me, and with his free hand he stroked my legs and the front of my panty. Then he placed both his hands under my thighs and opened my legs and lifted them up until they were wide open. He fumbled around and I felt him move his cock and inside the leg opening of my boy-leg panties and nestled it against the crack of my arse. The only thing protecting my anal opening was the thinly stretched nylon of my pantyhose gusset.

"Careful!" I whispered into his ear as I felt him stabbing against my pantyhose, his cock driving the translucent material against my sphincter bud.

"You can't fuck me; I'm sorry," I whimpered into his ear, "I'm just not ready down there ok?" I pleaded.

"Ok Michele, I just couldn't resist trying that's all," he whispered back.

I felt Robby move his body again so that his cock came to rest against mine, only the nylon of my pantyhose separated our phalluses; he adjusted the satin gusset of my panties so that it encased the top of his shaft. He gripped my buttocks and started 'cock fucking' me; our rampant members, only gossamer pantyhose separating them, rubbed against each other.

I bucked up against him, my stockinged legs locked around his bare waist, and got into the rhythm, fucking him back. We got into sync with each other and humped and grinded against each other as we kissed and stroked and fondled, and moaned and groaned and sighed.

"Fuck me,' I hissed into Robby's ear.

"Fuck me! Fuck me!" I seethed, as I felt my orgasm approaching.

Robby pushed his cock hard against mine and squeezed my pantied buttocks and he bucked and forced his member hard against me. As his rampant cock stroked against mine I could feel that my pantyhose gusset was soaked with our pre-come. I felt him push his body down hard so that the pressure from my nylon encased cock and my satin panty panel increased his pleasure and the intensified his pleasure. I pushed up against him, my legs locked around his torso and my arms around his neck, and I writhed and wriggled underneath him as my orgasm approached.

I forced my tongue deep inside his mouth and clung to him as my body spasmed. Great jets of sperm erupted from my throbbing cock and soaked the pantyhose and the panty material surrounding our melded penises. Robby's cock shuddered and pulsed and spat forth his hot issue, mixing with mine as our cocks continued to rub together. We clung to each other, moaning and wailing; kissing and stroking as our orgasms rocked us. Robby's hands clutched my pantied buttocks and his fingers grasped the gauzy material so tightly that he tore open the rear of my pantyhose gusset.

Robby writhed and slithered on top of me as our hot secretions combined and our come-slicked cocks rubbed together, draining the last of the fluid from our bodies. We slowly came down from our respective orgasms, gently kissing and fondling each other until Robby gently lifted himself up off me.

"That was great Michele; but I gotta go," he said.

His deflated penis hung underneath his slight beer-gut, a string of clear fluid leaked from the eye of his glans and drooled onto my leg. I smiled up at him.

"Ok Robby thanks for the lovely evening."

Robby showered first and then dressed. When he came out of the bathroom I went in and tried to clean myself up as best I could. Fixing my makeup was easy but my skirt was wrinkled was splashed here and there with silvery sperm stains and my panties and pantyhose were soaked with semen. I wiped as much of the semen away as I could with a towel. My nylons were laddered all the way down the back of my legs and my pantyhose gusset was torn to shreds. 'Never mind' I smiled to myself; 'I can always buy pantyhose'.

Robby was dressed when I came out of the bathroom. He was standing in the centre of the kitchen-diner smoking a cigarette looking anxious to leave. I tottered over to him and he kissed me softly, the taste of fresh tobacco on his breath.

"I really wanted to fuck you, you know; how often do you come to town?" he asked.

"Not very often I'm afraid. But if I ever do I'll be better prepared; and it's not very often I that say no to a good fucking," I joked.

"Here is my e-mail address; keep in touch and if it looks like I'll be coming this way we can arrange something," I said handing him a card with my msn e-mail address on it.

"Of course you know better than to call my mobile number unless we have an arrangement," I went on.

"Of course Michele; discretion is my middle name!" he smiled.

"Any chance we can meet tomorrow? It's my last night in town and I'm free," I pleaded.

"Sorry hun; not a chance. Got a previous engagement I'm afraid," he smiled back.

We said our final goodbye with a tender kiss and Robby sidled out of the door and into the night.

Robby still hasn't e-mailled me yet and I am still yet to e-mail Lynn. I feel a little guilty about Lynn somehow; so once this story is published I will contact her and tell her all about my naughty expedition in her hometown.

10 November 2007.

Postscript:

I will continue to write my True Stories because I love to share my real life experiences. But first I want to write a couple more chapters of "Lady in the House" as I have some good plot lines developing in my head and I think they are worth exploring.

  

  

  

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