True Stories

by

Michele Nylons

Part II

    

In part one of True Stories 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 to the present and tell you a true story that occurred only last week; that is 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 who 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 has 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 I met with on a number of occasions and had a wonderful time (see pictures in KTMgirls); 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 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 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, arse crack 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 (I trim but do not shave my underarms) 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 breast bone as 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 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 from 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, 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 breast bone (Notice I haven't yet applied mascara; because the face powder would stick to it, silly!) So now; lashings of black mascara to the undersides of my top eyelashes and the top of my bottom eyelashes (never try to put mascara on both the top and bottom of your eyelashes because when you blink the fucking stuff will end up all over your eyeshadow and also fall onto your cheeks). Anyway, as usual I had to gently lift a few flecks of mascara off my cheeks with a cotton bud. 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 bits and bum, giggle), 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 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 stocking carefully up my legs 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, giggle).

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. It's very tight and a few years ago I would have been too fat to wear something like it. 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! A 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 KTMGirls, TVChix or my new 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.

Lippy time! I took the applicator for the plum coloured basecoat and outlined my lip-line and then coloured in the rest of my lips, top and bottom, and pursed them together just like you see the women on the telly do; it works! I get a good natural lip-line over which I just have to put the second coat. Using long-lasting lippy you need to be careful not to fuck it up because that stuff is on to stay! I took my wig; a nice brunette, shoulder length, with lighter streaks through it, and brushed it out again and then pulled it on and adjusted it. I made sure it was a nice tight fit with the fringe nice and even just on my eyebrows; I brushed it in place, combing it around and over my shoulders.

I clipped on my earrings; nice silver clip-ons with three separate drops on each of the earrings, each drop ending in a small diamante. (Girls; you really have to shop around to find good quality clip-ons these days!) And next; the clear, top coat of lippy went on over the basecoat; it gives a nice shine that will last most of the evening. Finally I sprayed a liberal amount of perfume in my hair, on my cleavage and up under my skirt onto my thighs. Then I tottered into the bedroom to look in the full- length mirror; "Hello Michele; you look wonderful!" I say to myself. Back to the lounge to light up cigarette, sip some wine and do my nails with a nice nail polish which matches my lipstick. I check the time on my cell phone again; fifteen minutes to go, just enough time.

I paint my nails, finish my ciggie, and go to the bathroom and rinse with mouthwash again. I retrieve the charcoal grey suit jacket from off the back of the chair and slide my arms into the sleeves and button the jacket. I pull the sleeves of my top down and adjust them at my wrists and then readjust my bracelets. I flick my hair out from under the collar of my jacket and walk back to the bedroom to stand in front of the mirror. The fitted jacket has a small lapelled collar; open at the top and tight around my waist where I have fastened the two buttons. I brush my hair again and look at the end result; one hot, fuckable secretary!

I turn on the bedside lamps, spray a little perfume over the coverlet on the bed, and turn off the overhead light. I walk back to the lounge and turn on and dim a free-standing lamp and turn out the main lights; I put a nice easy listening CD into the deck and refill my wineglass. I take my wine and a freshly lit cigarette and stand near the breakfast bar and look longingly at my mobile phone; it's 8:05pm and I'm nervous. I can never sit and wait for a girl or guy to arrive; I have to stand for some reason. The phone gives out a familiar buzz and I look at the screen; it says "Vanessa calling!" I answer it and give Vanessa the address. She is only three blocks away and five nervous minutes later there is a knock on the door; it opens and in walks a handsome, slim dark haired man carrying a large valise. Vanessa had arrived!

Vanessa is petite, dark and about the same age as me; what I liked was that she came straight up to me and kissed me. I love to kiss and be kissed but I have met a few men how will not kiss Transvestites. I think it's ironic that these men will let me suck their cock and will even suck mine but won't kiss me because "it's not right to kiss a Trannie"; how fucked up is that? Anyway Vanessa is a great kisser and I soon had her seated and offered her a drink which she accepted.

We chatted for a while and got to know about each other; finally I couldn't wait any longer and offered to help her dress and to get made up, to which she eagerly agreed. Vanessa went into my bedroom and requested privacy whilst she started to dress; which of course consented to. She called me into the bedroom after a few minutes and I found her dressed in a black cocktail dress, black nylons and high heels.

I took her into the bathroom and applied her makeup for her, giving her a few of my tips and advice on what I thought would suit her. I made her up almost identical to me; using the same shades of makeup. I brushed out her wig and fitted it in place, it is black and suits her dark complexion and the black ensemble she had chosen to wear; she looked lovely. We moved back into the lounge and commenced kissing each other passionately, our tongues intertwining and lipsticked lips locked. I slid my hand up her stockinged leg and rubbed her nyloned thigh; I put my hand on her stocking top and stroked her there and also on the bare skin above her stocking.

I couldn't wait any longer and I slid my hand over panties and grasped her long thick cock, rubbing it through the sheer nylon of her panties. Vanessa responded by sliding her hand up my skirt and reciprocating the gesture, stroking my hardening member through my knickers.

I loved the feeling of her stroking my cock whilst I was stroking hers; our kisses became even more passionate and our tongues were slipping in out of each other's mouths in a frenzy. I opened Vanessa's knees and pulled up her skirt so that I could see her panties, they were white nylon briefs and my red painted fingernails looked so erotic as I slid my hand along per panty encased cock. I eased out of our embrace so I could watch as I freed her hard cock from the waistband of her panties. Vanessa's cock is about seven inches long, thick at the base, tapering to the shiny pink glans; I couldn't wait to get my mouth on it!

Vanessa helped me out of my jacket so we could be more comfortable; then she also lifted up my skirt and began to wank my hard cock. We looked like real sluts, two heavily made-up tarts with out skirts raised displaying our stocking tops and knickers as we wanked each other's cocks.

We started kissing again and embraced each other with our free hands. After kissing and wanking for about ten minutes I pushed myself away from her and she mewed in disappointment; but not for long. I dropped to my knees between her legs and started kissing her stocking tops. I kissed and licked her thighs and worked my way up to her cock which I greedily engulfed. I licked and sucked the weapon and settled into a steady rhythm; fellating Vanessa whilst I looked up into her pretty dark made-up eyes. I was on my stocking knees, my skirt up around my waist and my high heels kicked out behind me, my head bobbing up and down as I sucked her cock.

Vanessa put a hand on my head and pushed my face harder into her lap and started to lift her arse to thrust her penis in and out of my mouth. She looked lovely sitting there with her black mini cocktail dress pulled up to her waist, her black stocking legs spread wide, her high heels drumming on the floor with me kneeling between her legs sucking her hard cock which was standing upright outside the waistband of her pretty white panties. Vanessa finally pushed my head away, "I'm going to come if you keep that up," she said, "and I really want to fuck you Michele."

That was enough for me I stood up and reached out and took Vanessa's hand and led her into the bedroom. I lay Vanessa down on the bed and took out a package of condoms. I tore off the wrapper and put the slightly unwrapped condom in my mouth and went down on her hard cock, pushing the condom over the length of her penis with my red lipsticked lips. When I lifted my head, Vanessa's cock was sheathed with the condom.

I took out a tube of lubricant and applied a big dollop to her cock and smeared it up and down so that it was covered entirely with lube; Vanessa, the dirty bitch, fucked my hand as I lubed her up (and I loved her for doing it!). I smeared another dollop of the clear viscous liquid on her knob and then started rubbing lubricant around my opening. Vanessa got to her knees and pulled me onto my knees also.

"Let me do that," she said, much to my pleasure.

"Yes please," I said, lifting my skirt like a good whore.

Vanessa pulled my knickers down and left them draped over one ankle so that they were just hanging there just above my high heel and then she started lubing up my arse with the lubricant. The stuff was cold and sticky but I loved it when she finally eased a finger inside me and started to lubricate my back passage. She pumped more of the lubricant inside me,

"Use plenty," I said, "I'm really tight and I need lots of lube or it hurts," I explained.

Vanessa decided I was suitably lubricated and positioned herself behind me, between my shiny stockinged legs and nudged the head of her cock against my puckered bud.

"Gentle!" I insisted "Be gentle!"

Vanessa pushed forward and her glans forced itself inside my sphincter; fuck it hurt! It always does for me. Until my back passage is fully lubricated and full of cock the first insertion always hurts, but I'm used to it now and I know that the initial pain is well worth it. Vanessa pushed forward slowly and her hard lubricated member forced its was inside me until I felt her pelvis push against my buttocks. My arse was burning but very slowly that lovely full feeling of a hard cock deep inside me coupled with the divine sense of the head pressing against my prostate started to worm through my body.

I started to rock slowly back and forward on my knees feeling Vanessa's cock sliding in and out of me, Vanessa squeezed more lube on her cock and took me by the hips and began to fuck me. I loved the feeling of her hard cock filling me up and her pantied crotch smashing against my buttocks. Vanessa moved her hands to my thighs and grasped my suspender straps and pulled me back onto her cock, the suspenders were like reins on a horse as she fucked me, building the pace faster and faster.

I reciprocated and thrust back against her, wriggling my buttocks against her crotch as she fucked me like a whore. I looked into the mirror and became even more excited. Reflected in the full length wardrobe doors is a wonderful sight. I'm a heavily made up whore, on my knees, my hair framing her my face, eyes half closed in concentration and ecstasy as I buck and writhe, my skirt lifted up around my waist, the sleek taupe stockings encasing my legs with my high heels spread wide as I reach behind myself and grasp the thighs of the bitch dressed all in black who is between my knees, furiously fucking me. My jewellery glitters in the soft light and my knickers hanging from my ankle add to my whorishness.

Vanessa on her knees between my opened legs is holding my suspender straps like reins and she is slamming herself into me; thrusting and pushing against me as I wriggle my arse; impaled on her hard cock.

"I can't keep this up much longer; my knees hurt," Vanessa complained.

She pushed me forward and I felt her cock slide out of me and I voiced my disappointment.

"Please Vanessa; fuck me; it feels so good," I whined.

"It's ok Michele, I'm just changing positions," replied, and eased me down on the bed so I was lying sideways.

Vanessa moved behind me and got into the 'spoon' position; she lifted my leg and began probing at my passage with her hard member. Her cock found its mark and slowly slid deep inside me again; this time there was no pain as I had been well stretched and lubricated. Vanessa picked up the pace again and began to fuck me hard. I pushed back against her and felt her fill me and began to experience the thrill of her glans rubbing up against my prostate again. Vanessa reached around and slowly wanked my semi-hard cock (It never gets fully hard when I'm being fucked but I still love having it stroked and I have no problem coming this way).

Vanessa lifted my right leg up higher so she could get all of herself inside me and I loved the sight of my stockinged leg sticking up that way, my nylons and ankle bracelet glittering and my pink boy leg knickers hanging around my calf. Vanessa moved her free hand to my knickers and started rubbing them up and down my leg and I moaned with the added pleasure of the silky material rubbing on my stocking. I was close to coming and Vanessa could feel it as I thrust and wriggled beside her as her impaled cock jack-hammered in and out of my burning arse.

I moved her hand off my cock and began to wank it furiously myself as I felt my orgasm building. The sensations deep in my bowels built up to a crescendo and It felt like a thousand butterflies were fluttering inside me; my cock spasmed and streams of creamy white sperm shot out of my cock staining the coverlet. I moaned and mewed as my climax gripped me and I thrust back against Vanessa and bucked and wriggled as my back passage spasmed. It was delightful; I just wish Vanessa had come with me, but she was saving herself.

When my orgasm subsided, I got up from the bed and pulled up knickers and straightened my skirt. Vanessa got up off the bed her erect penis thrust out from under her dress; she went into my ensuite and disposed of the condom and took my hand and led me back into the lounge.

"You know what I want now," she demanded, and I took my place between her opened legs again and began to suck on her hard cock.

"Yes; yes! I'm close now! Play with my balls too; stroke them and stroke the base of my cock as you suck me," she insisted.

I did as she asked and swallowed as much of her phallus as I could as I played with her balls and shaft with my red nail-polished fingers whipping up and down her shaft as I moved my mouth back up her member so that I could lash her glans with my tongue. Vanessa was close now and she put both of her hands on my head and pushed my face hard into her crotch and I engulfed her penis with my mouth and worked my tongue around the shaft.

Her cock convulsed and she shot stream after stream of hot semen into my mouth and I felt my mouth fill with her spend. I swallowed the musty tasting offering and continued to suck and slaver her cock until it slowly started to deflate.

After licking her well and truly clean we sat together on the lounge for a while kissing and stroking each other tenderly. We chatted and smooched for the rest of the evening until it was time for her to go; when she showered and changed as once more became the dark skinned handsome man who had arrived at my door a few hours earlier.

Vanessa; if you read this essay I hope you realise how much pleasure I had with you and I hope that you will be passing through my city again sometime in the future. I'll keep in touch by email sweety, and keep you abreast of my latest adventures.

  

xxx

Michele

To be Continued.

  

  

  

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