Chapter 2

In part one of True Stories Part I discussed how my transition from part time panty wearer to part time transvestite came about. I also told the true story of my first time with a transsexual prostitute. In this instalment I have decided to leap ahead and tell you a true story that occurred only in July 2006.

I am a part time transvestite who has had many adventures and who regularly entertains other men, women, transvestites and crossdressers who enjoy our special secret world. I travel extensively with my work and am therefore able to have many lovely encounters in discreet meeting places; either hotels, my own apartment and sometimes but rarely, at other people's homes. My latest encounter occurred in a capital city on mainland Australia. It was with a transvestite whom I have been in contact with for a few months via email, and who I was finally able to meet up only recently.

Vanessa had seen my profile at TVChix and contacted me via email and we began a dialogue that had gone on for several weeks. Finally the stars aligned and we were able to meet when she happened to be in the same city where I maintain an apartment.

This Vanessa is not to be confused with the Vanessa who used to live in Townsville who have I met with on a number of occasions; I even had the odd orgy with her, Tracy, Mandy and an admirer; but that's for a later instalment.

This Vanessa is from Melbourne, and I arrived at my apartment one afternoon after flying in from interstate to find that she had left a message on my cell phone answering service. She was in town and looking forward to a meeting!

Meeting someone new for the first time is always exciting and I have to say a little unnerving; when you are a closet transvestite, discretion is always an overriding factor when arranging a meet.

As it turned out I called Vanessa on her mobile phone and she was very happy to hear that I was in town and also keen to meet. She was staying at a hotel but when I explained to her that I had my own place she was very keen to meet here rather than at her hotel. I have to say I felt better about that too. I would rather meet at my place when meeting for the first time. The obvious disadvantage is that once a person knows where you live, you give up some of your anonymity, but the advantages are many.

For a start, I prefer to meet others when I am dressed and fully made-up as Michele rather than have them see me as my male day to day self. When I am Michele I look nothing like my male alter ego so the chances of later meeting someone with whom I have had a sexual interlude and being recognised in my male alter ego is virtually impossible. This is important to me when meeting for the first time (I'll tell you a true story later about a very unpleasant experience I had with an admirer who stalked me for a little while.) I also like the fact that being on my own ground I have better control of the situation and have my entire wardrobe, toys and accessories available to me.

I never have to worry about being chucked out in the street dressed as Michele; highly unlikely, but some first-timers can react very strange during or after their first experience with a transvestite. I'll tell you a true story or two about my experiences with a couple of first-timers and their reactions in later instalments.

So anyway; I arranged a meeting with Vanessa at 8:00pm at my place and gave her the general location of the meet, with directions for her to call me when she was near to where I live and then I would give her the street name and apartment number. I have learnt not to give out my address until the person I am meeting with calls me a few minutes before the meeting. It is very disturbing knowing that some stranger has your address and then doesn't turn up for the meeting. The practice of not giving out my address until it is actually time to meet also discourages timewasters; although there have been few occasions when I have been all dressed up and waiting in anticipation for a new admirer to call and they never did; but it's better than the alternative.

Oh the trials and tribulations we girls go through for you admirers! Vanessa had to come to my place in drab and dress here. She told me she had plenty of clothes and her own makeup, wig and shoes in a valise which she would bring with her. She also told me that she had met with other transvestites before and so she was not new to the 'game', but a little inexperienced with makeup. Like myself she is also married and 'in the closet'.

I allowed myself an hour and a half to get ready for the meet and started my preparations early. I know I have described my transformation in great detail a number of times in previous stories but I also know a that lot of my readers like to read about how an everyday bloke transforms into an attractive (well I think I'm attractive anyway) transvestite. For those of you who can't be bothered, skip the next few paragraphs and go straight to the sex!

As I normally do when meeting in the evening, I poured myself a glass of wine and considered in what order I would transform. If I have plenty of time, I sometimes like to do my nails first if I don't have too much shaving to do; but tonight I felt like painting my nails last thing; that way I could sit and have a glass of wine and a cigarette whilst doing my nails and appreciate the building anticipation of the meeting.

I went into the bathroom and brushed my teeth and rinsed with mouthwash. Next I gave my face a really close shave; shaving some areas two or three times until they were as smooth as a baby's bottom (or as close as possible anyway). Girls; I can't tell you how important this is if you are meeting an admirer, crossdresser or transvestite with romance on your mind. There is nothing worse than meeting with a stunningly dressed and made-up transvestite or crossdresser, only to feel the rasp of 5 o'clock shadow when you kiss her.

Next I ran my electric shaver over my arms, legs, chest and pubic region. I shaved from the tops of my knees to the tops of my thighs with a blade razor and shaving gel and then my chest and hands. I had earlier smeared hair removal cream over my buttocks, around my anus and crotch; I also put hair remover on the small of my back. After about twenty minutes of shaving, it was into the shower. I showered all over, washed away the hair remover and shampooed my hair. Whilst I was there I also gave my back passage a good douche.

Some of you may think that I am providing more detail than is necessary; but the girls out there who actually meet up and have sexual encounters with others will recognise these basic preparations. This is the real world us transvestites live in; it's not like in many of the stories you read here where some guy just throws on some lingerie, a wig and makeup and suddenly becomes a stunning woman who the guys just can't keep their hands off; that's just bullshit; I wish it was that easy!

Now I had what I call the blank canvass from which I can create Michele. I can be a whore, a naughty secretary or whoever I want to be, depending on who I am meeting with and my mood at the time. I no longer have an extensive wardrobe (I found I never wore half of it anyway) but I have a nice selection of clothes that mix and match, a good quality wig that suits my face (If you are over 40 please don't go out and buy an expensive wig with long curly blonde locks like so many first timers do, not many girls over thirty can really carry it off! stick to a nice bob!) and good quality high heels. I stick to my favourite foundation and use two face powders; I do have lots of shades of rouge and eyeshadow and a few lipsticks. I wear expensive two-coat long lasting lipstick when I am dressing for a meet (for obvious reasons, giggle). Let's face it, when it comes to eyeliner and mascara; why not just stick to black?

I laid out my makeup on the vanity; sprayed a liberal amount of nice anti-perspirant deodorant under my arms and started my usual ritual. I had acquired a nice two-piece, charcoal grey, business suit that very day (only $20 at the Op Shop and it is a good Australian label!) and wanted to go for the naughty secretary look.

I applied dots of cheap pink lipstick over my face and neck along my 'beard-line' and smoothed it out with a damp makeup sponge. This is a trick I acquired off the web and it works well. I don't have a dark beard but it does stop that 'blue' look that can develop when you are made up after a while. I used to use a heavy foundation specifically designed for girls like us, but this trick works just as well, if not better, and its heaps cheaper. I then applied my foundation; it's about one shade darker than my skin. I set the foundation with matching face powder from a compact using a large brush; that's the basecoat done. I spread the foundation and powder from the very top of my forehead all the way down my neck to my breastbone because I like to wear vee or scallop neck tops and open neck blouses.

Next I started on my eyeliner; I always do this next because it's the hardest skill to master and if I fuck it up I can clean it away with moisturiser, reapply foundation and powder to my eyes and start again. I like to line all along the edge of my eyelids along the lash-line, from the very inner corners of my eyes right out to the very outer corners where I take the line on the top lid to just outside my eyelid and I try to thicken the line as I work from the inside to the outsides of my face. This is the most frustrating part of applying makeup for me and once I had achieved the look I wanted I took a quick break and had a drink of wine; the rest is easy!

I did my eyeshadow next; tonight two shades; turquoise and pink. I applied the turquoise to my eyelids and then blended the pink right up to my eyebrows and then added more turquoise to bring the eye shadow out past my eye socket a little. I used a damp applicator then smoothed and blended the colours with a fine brush and finally the tip of my little finger. Next I rouged my cheeks; I used a dark peach colour, and brushed it on my cheeks in line of the centre of each eye working out and up slightly. I left it reasonably dark as I still had the final coat of face powder to blend over it.

As my wig has a long fringe and my eyebrows are fine and well trimmed anyway, I never use an eyebrow pencil so next I applied a liberal coat of finishing powder over my face. It's a shade lighter than my compact face powder, it's finer and leaves a nice glow without making my face look shiny. I use a big brush for this and apply plenty all over my face and all the way down my neck to my breastbone (Notice I haven't yet applied mascara yet; because the face powder would stick to it, silly!) So now I put lashings of black mascara on my eyelashes. So now, except for my lipstick, I was done!

I went into the bedroom where I had laid out my clothes for the evening. I always pick out what I want to wear and lay out only those items; because if I lay out all of my clothes, like most women, I will fuck around for ages until I finally decide what I want to wear. Often I will put on a pair of sheer to the waist pantyhose as a foundation garment (ok, and because I like the feel of the sheer nylon on my body), but because I had freshly shaved my legs tonight I decided that stockings alone would be fine. By now I was becoming aroused as I always do when I'm making myself up and especially when anticipating a meeting. I wasn't hard but I had a little dribble of clear pre-come on the eye of my penis. I had to wipe it away otherwise it would stain the front of my panties (which will end up stained soon enough anyway!).

I clipped my white lace garter belt together and stepped into it, pulling it up and adjusting it just below my waist. I untangled the garter straps and sat on the bed and pulled a pair of sheer flesh-toned, high sheen, lace-top stockings up my legs, carefully clipping the garters to the stocking tops. I stood and carefully smoothed out the nylons and adjusted the stocking tops in my full length mirror so they sat evenly at the tops of my thighs. I stepped into a pair of pink lace, boy-leg knickers which sat comfortably snug on my buttocks and I adjusted my penis in the front panel of the knickers so that the bulge was not too noticeable. Girls; panties and knickers always go over your garter belt when you are expecting company; that way, later, your lover can slide them down your legs without having to unclip your garters from your stockings (that's if your lover want's you with your panties off of course).

I selected the white full cup brassiere which matched my garter belt; I don't use breastforms so it's pointless me wearing a half-cup bra. I have a little natural cleavage (no I am not fat!) which I augmented with some rolled up nylons to fill the cups (sometimes I use a nylons filled with rice - never water like I have heard some girls use!!!); and adjusted them into a nice shape. I sometimes wear a half or full slip but as my suit skirt is lined; tonight I didn't bother.

I pulled on a nice tight, longsleeved, metallic blue, scallop necked top. It's a sheer lacy manmade fabric, which is slightly see-through with a little glitter in the weave. I pulled it down and adjusted the wide neck so that it covered my bra but showed my natural cleavage and long neck.

Next I stepped into the skirt which is charcoal grey with a pleat either the side at the front; the hem comes to about four inches above my knees. I zipped up the skirt and straightened the hem and waist; I reached under and un-snagged the nylon liner from where it had caught on a garter clip. The lined skirt on my stockinged legs and tight knickers felt absolutely wonderful! I had a quick check of the time on my cell phone to see that I had about half an hour before Vanessa called.

I grabbed the suit jacket, my jewellery and high heels and went into the lounge. I hung the jacket over the back of a chair; refilled my wine and sat down to put on my shoes and jewellery. I have recently acquired two lovely bracelets; one black, the other turquoise. They are about two inches wide and made of polished stone beads strung together with antique metal fittings; and they are an absolute cunt to put on! Because they are fastened by a chain and spring clip, and I was by myself, I had to put each of my wrists on the table and drape the bracelets one at a time over each wrist and try to clip the catch through the chain with the other hand. After much swearing I had them on and then I slipped a large silver ring onto my right ring finger.

My current favourite shoes are a pair of black, strappy, high heeled sandals that have a small rhinestone flower on the top and straps that wrap around my ankles (see them in my pictures at TVChix or my Yahoo website). I slid them on, buckled the straps, and then put a silver ankle chain around each ankle; one of which has a small drop diamante. (I know a girl should only wear one anklet; but with us trannies, more is more, not less is more!) Next I went back to the vanity with the remaining jewellery. I put a choker of small turquoise faux pearls around my neck and then hung a silver necklace with three small drop pendants consisting of tiny pearls in silver settings around my neck; the centre drop coming to just above my cleavage.