Michele Nylons' Stories Ch. 03

This is a continuation of my True Stories series, where I tell my readers about my real life adventures. In the next two instalments I will tell you about some of my encounters that were not particularly satisfactory. As most closet Transvestites will know, there are a lot of losers out there and some of them can even be a little scary.

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Story One - The Reluctant Stalker

As most of my readers know I live in Australia and travel a lot with my job; this assists me greatly as I can maintain an apartment in a different city from my family home and use it for Michele's encounters and other fun activities. At the time of this incident I had a nice little two-bedroom unit (town-house) in one of Australia's capital cities. It was located in a quiet street and was set well back from the street and quite secluded from the adjoining units; it was just the place for a closet Trannie to ply her trade.

I had been advertising my availability for casual meetings on the noticeboards of a couple of sex shops in the area (before any of you groan, read parts one and two of this series and you will see how I vet my punters; although in this case the vetting process wasn't hugely successful), and had enjoyed a number of pleasant casual encounters with admirers who had responded to my advertisement.

My 'Michele' cell phone rang one evening and a guy introduced himself to me calling himself Peter. He described himself and said he had never been with a Transvestite before but would really like to try it. I could tell by the way he kept calling me "mate" that he hadn't been with a TV or crossdresser but I was willing to talk to him and see if he might be acceptable as a potential admirer.

He was in his forties, large build, bearded and worked as a tradesman and wanted to meet discreetly during the day, mid-week as he was married. I said it would be difficult for me to meet during the day during the working week due to my work commitments but that I'm sure if he was really interested we could work something out.

Peter asked me to describe myself and my interests, which I did. He became particularly excited when I described how I wore miniskirts, stockings, high heels and lots of makeup; and again he expressed a strong desire to have his first encounter with a Transvestite.

I am always very wary of men who are first time admirers as they are often enamoured with the fantasy of being with a Transvestite and have masturbatory fantasies about what it would be like; and then they find they can't go through with the reality of the situation when they get the opportunity realise their fantasy. I told Peter this and he insisted he was genuine. I told him that if he really wanted to experience an encounter with me I'm sure he could find some excuse to get away one evening or maybe for a couple of hours on the weekend, and then I could attend to his needs. He said he didn't think so; so I thanked him for calling and wished him the best.

I thought that would be the end of it but over the next two weeks Peter kept calling me on my cell, mainly during the evenings and on weekends and expressed how much he really wanted to have an encounter with me but insisted that we could only meet during the day on a weekday. I suspected that on many of these occasions he was drunk but I told him that a meeting during the day midweek was highly unlikely. I probably should have just ignored him but he was genuine enough to leave his cell number (I definitely will NOT meet with a person who has suppressed their caller ID on their mobile phone when they call me) and he asked me to call him if there was ever an opportunity to meet midweek during the day.

As it turned out I was able to get a half day off from work one day and debated whether I should call Peter or not. I was feeling particularly horny as my regular boyfriend, Buster (more about him in a later instalment), had not been in town for a while. I debated the pros and cons of meeting with a 'first-timer' at my flat during the day and decided it would be safe enough. I sent a text a message to his cell "call MN if free to meet" and waited to see what would happen.

Five minutes later my Michele cell rang,

"Hello Michele Nylons speaking," I answered, knowing full well it was Peter from the caller ID.

"Well; can we meet then?" Peter's gruff voice responded.

"Yes we can meet; but there are a few ground rules," I responded, "I need an hour to get ready and then you call me from (a street close to where I live) and then I'll give you the address where I live ok? My place is only five minutes away from there by car."

"Fuck that!" Peter exclaimed, "I can only get away from the job for about half an hour and I don't want to waste most of my time sitting in a fucking car waiting to call you."

I should have called the meeting off then but I was quite horny and a little sympathetic to his plight. I went on to explain,

"Look honey, I rush things along I can be ready in half an hour ok?" I asked.

"Well I suppose I can get away long enough to spend half an hour with you," he sulked.

"Well look Peter, you're the one who has been calling me incessantly begging for a meeting. This is how I do it when I meet guys for the first time ok?" I responded.

"Ok, I'll call you in a half hour Michele. I hope this is worth it," he replied and hung up.

Again I debated whether to meet this guy, but my excitement and the anticipation of meeting an admirer overcame my caution and I sauntered off to the bathroom to make my transformation.

I shaved my face very closely, showered and cleaned my teeth but did not worry about douching. Being a first timer, and only having half an hour to play, I decided that Peter was not going to fuck me this afternoon; if I liked him I might let him on another occasion I giggled to myself. I went to the spare bedroom and closed the curtains, sprayed some air freshener around, cranked up the air-conditioner and opened the walk-in closet where my Michele accoutrements were kept. I rummaged through my makeup and took what I needed back into the bathroom to fix my face.

I applied a few dots of bright red lipstick to my cheeks, chin and neck and rubbed the lipstick in with a damp makeup sponge. This is a trick I had learned to hide any dark patches caused by facial hair follicles (sometimes called five o'clock shadow). I then applied a liberal amount of foundation and set it with an application of face powder. I did my eyeliner as usual before I did anything else, then applied some turquoise and pink eyeshadow and some blush on my cheeks. I applied a liberal amount of mascara to my lashes and then applied a final coat of glossy face powder all over and then carefully applied two coats of lipstick and bit down on a tissue to set the lippy. There, my face was done; hurried but acceptable.

I went back to the spare bedroom and rummaged amongst my lingerie collection. As I hadn't shaved my legs for a few days and had no time to do so now I decided to wear a pair of sheer to the waist, taupe pantyhose as a foundation garment. As I wouldn't be letting Peter fuck me the gusset wouldn't be a problem (besides plenty of men have ripped open the gusset of my pantyhose to get access to my bottom before). I slid them up my legs and smoothed the sheer nylon along each leg and around my buttocks and crotch. The tingle of the nylon against my skin and genitals and the anticipation of the forthcoming encounter caused me to become turgid. I tucked my semi-hard penis between my legs and slipped on a pair of bright red, full-cut, nylon panties.

Next I stepped into a white lace suspender belt. Again, if I was meeting someone who needed to remove my panties for access to my bottom I would have put the panties on over the suspender belt to allow my panties to be pulled down without getting caught on the garter straps, but today this was not necessary. I slipped on a pair of black nylon, fully-fashioned, stockings over my pantyhose and up my legs and fastened them to the garter clips. I was going for look and feel here rather than the practicality of permitting access to my genitalia. I figured that having only half an hour to play, a first-timer could make do with my hands and mouth.

I slipped on a pair of black high-heeled court shoes and wriggled into my favourite red Lycra miniskirt. I pulled on a white brassiere and stuffed the cups with old nylon stockings; I was going for speed, not authenticity. I buttoned up a white nylon blouse and tucked the tails into my skirt. I grabbed a wig, a brunette bob with lighter highlights, and went back to the mirror in the bathroom. I pulled on the wig, adjusted it and gave it brushing. I went back into the bedroom and found a nice pair of silver drop earrings and clipped them to my ears; I put matching necklace around my neck. There! I was done! From man to Michele in a little over twenty minutes!

I tottered downstairs to the lounge, my high-heels clicking on the wooden stairs and tiled floor, and poured myself a glass of red wine, lit a cigarette and put my cell phone on the coffee table next to my wine glass, and started painting my nails. I didn't think I'd have time, but if I painted my fingernails with just one coat of nail-polish and wasn't too fussy about the finish I could probably get them done before Peter arrived. Men love painted fingernails.

I had only one fingernail left to paint when my phone rang; the dial displayed 'Peter', so I picked it up and answered,

"Hi honey, you ready for a good time," I cooed in my sexiest imitation sotto femme.

"What's the address!" Peter practically growled into the phone.

For one last time I considered whether I should meet this guy or not; then I gave him the address.

"The front door will be unlocked but closed," I instructed, "let yourself in and lock the door behind you; I'll be in the lounge out of sight of the open door just in case some nosey neighbour is looking," I said.

"Yeah, ok Michele. See you soon," Peter said and rang off.

I picked up a bottle of perfume, my favourite Poison ®, and sprayed a liberal amount on my neck, wrists and under my skirt. The curtains were already drawn so I dimmed the lights and stood up to greet my guest. I moved into position where Peter would see me as soon as he came through the door but where I would be out of the sight line of the street and adjoining flats.

A couple of minutes later there was a loud rap at my front door. 'Fuck,' I thought, 'I told him to come in and lock the door after he entered.' So was this Peter? or was it someone else? What a dilemma! Should I answer the door, or will there be someone there besides my prospective admirer?

Then the door opened and Peter strode into my flat slamming the door behind him. He stood there in the entry and surveyed my flat, casting a critical eye around the place. He was a big man with a solid paunch that hung over his belt; he had dark curly hair and piercing eyes. He wore tailored work shorts and a golf shirt. An Alpha male to be sure, he exuded arrogance. I actually found his maleness attractive I must say. I moved to the centre of the lounge room and pirouetted.

"Well do you think," I asked.

"At least you like a woman even if you sound like a bloke," he responded and strode across the lounge to stand in front of me.

"Do we do it here or in the bedroom?" he asked.

I was a little baulked but aware that he was probably nervous as this was his first time with a Transvestite. He was probably using arrogance to cover up his nervousness.

"I have a spare bedroom upstairs that I like to use," I said.

"Well what are we waiting for, lets go Michele, time is running out," he replied, looking at his watch.

I led the way upstairs and he followed closely behind me. As I started to climb the stairs ahead of him his rough hands ran up my thighs and onto my buttocks, his fingers rasping on the sheer nylon of my stockings and panties.

"Fuck that feels good," he groaned, "Women today never wear stockings any more; I love the feel of stockings."

He continued to rub my legs and bottom all the way to the bedroom. When we were finally standing next to the bed I turned and faced him. He looked me up and down and steadied his gaze on my face.

"You like a real fucking woman you know; pity you'll have to get that shit off your mouth," he said, and reached out and wiped most of my lipstick off my lips with his thumb.

"If I get any of that shit on clothes or face my wife will fucking kill me and if the guys at work see it they will guess what I've been up to."

I was quite taken aback by what he had just said and done, wiping my lippy away like that.

"Well Peter, I told you I am discreet. I would never get makeup on your clothes and you can always use my shower to remove any traces I leave on you," I said, a little angry at his actions.

"I suppose I could get naked, couldn't I," he answered, as if he had had an epiphany.

"Well why don't you do that while I put my lipstick back on. I'm sure you would prefer me to look as feminine as possible?" I replied and went into the bathroom and applied two coats of lipstick with a slightly shaking hand.

I was beginning to wonder again if I had done the right thing letting this guy come to my flat. 'At least with him naked in my bedroom I should be able to keep some control of the situation,' I thought.

I tottered back into the bedroom and found him standing naked, his clothes neatly folded at the end of the bed. His was quite hairy and his large gut was hard like a basketball and hung out over his genitals. His short stubby penis was hard and stood proud of the thick thatch of his pubic hair. I moved close to him and reached up and kissed him. He took my hand and put it straight down onto his stumpy cock, slipped his tongue between my lips and pulled me close; his other hand going under my skirt, firmly squeezing my pantied buttocks.

His beard tickled my face and his mouth tasted of his lunch and cigarettes but I immediately became aroused and responded to his kisses and rubbed my body against him whilst my painted fingernails fluttered up and down his penis. His little pink muscle was rock hard and quivering in my hand.

"Easy, I don't wanna come yet," Peter whispered, and he slapped my hand away from his manhood.

He held me in a bear hug, squashing me against his big body, his lips crushing mine and his tongue quivering in my mouth. Peter's hand slipped back under my skirt and began to roughly stroke my stoking tops, his breath was gasping as his hand his pulled at my suspender strap and buried itself in the nylon sheath between my stocking top and my pantyhosed thigh. As one hand massaged my nylon encased thighs the other slipped around from my buttocks to the front of my panties.

By this time I was quite aroused and erect in my nylon knickers; Peter's hand slid across the sleek nylon front panel of my panties tracing the outline of my cock. I shuddered and groaned and pushed myself harder against him. Suddenly Peter whipped his hands from under my skirt and gripped my shoulders and pushed me back out of his embrace.

"I don't know if I'm ready to touch you down there; I'm not a poofter or anything," he whimpered.

I was taken aback a little. As I have explained (and most Transvestites know), admirers often choke or panic during their first sexual encounter with a Transvestite or Crossdresser. Peter seemed to have gotten over his initial reservations and was certainly enjoying himself with me up until then. It was probably the first time he had touched another penis and the reality of the situation had probably just hit him. I went into damage control.

"Never mind honey, just lie back here on the bed and let Michele look after you," I cooed.

Peter lay down on the bed; his hairy body was rigid but his tiny cock had become flaccid and had almost disappeared in the tangled thatch of his pubic hair. I sat down next to him and began to run my hands over his body; my red nailed fingers stroking and fondling. He started to relax again and he extended a hand and stroked my face.

"Fuck you are pretty good looking for a guy; that makeup and shit you wear really makes you look like a woman," he said.

I didn't know wether to be complimented or insulted but I decided that Peter was having real problems coming to terms with the fact that he was having a pleasurable encounter with a Transvestite.

"Peter honey, if it helps, just think of me as a woman and enjoy what you see and feel. You don't have to touch me anywhere you don't want to. You don't have to do anything you don't want to," I whispered trying to put him at ease.

I bent over and gently brushed my lipsticked lips on his. He responded by pulling me to him and plunging his tongue deep into my mouth. I lay on my side against him and continued to kiss him and stroke his fat hairy belly and upper body. I slid a stockinged leg over his and slowly rubbed my nyloned calf against his groin. Peter started to push up with his lower body rubbing his hardening cock against my leg. I kissed him harder and scraped my fingernails gently all over his body, occasionally cupping his testicles and gently fondling them while my stockinged leg rubbed against his tumescent penis. I felt a wet patch develop through the double layer of nylon of my pantyhose and stocking on my right ankle and calf where my leg was rubbing against his cock. Peter was groaning now and close to coming.

He was certainly in a rush that's for sure; he grabbed my hand and pushed it down into his groin and I circled his throbbing little member with my fingers and began to gently stroke him whilst at the same time kissing him deeply and rubbing my leg against his belly and thighs.

Peter abruptly pushed me away and at the same time I felt a scalding hot stream of semen erupt from his cock and shoot over my hand, landing on my leg where it glistened and soaked into my nylons, the secretions drenched through the two layers of nylon and warmed my skin.

I quickly moved my head down and placed my lips over Peter's squat pulsing cock and slavered at his member with my tongue. Steam after stream of hot viscous semen erupted from his cock and I was forced to swallow as my mouth flooded with his spend; some of it escaped my mouth and spilled over my lips and ran down my chin. Peter's hands went to the back of my head and pulled me down on him with such force that my wig began to slip forward. He was groaning and thrashing as he orgasmed and eventually he calmed and became still, releasing his grip on my head. I was cleaning up, licking the sticky fluid that had matted in his pubes, when his hand came down again and pushed me away.

"Ok that's enough thanks," he said matter-of-factly.

"Fuck I needed that, the missus hasn't given me a root for months; fuck I came like a train. Now where's the fucking shower!" Peter demanded hardly looking at me.

"Through the door and across the landing," I answered as he lifted his large body off the bed.

"Are you ok," I asked, "some guys get 'post coital regret' after there first time with a Transvestite."

"It doesn't mean you are gay or anything," I said sympathetically.

"You fucking bet I'm not a poof; I just got my cock sucked by a Trannie that's all. I didn't fucking suck yours or anything!" he growled and stormed off to the bathroom.

I sat on the bed very disappointed. Not only was I sexually frustrated, this arsehole wouldn't even acknowledge my presence now that he had finished with me; he wouldn't even look at me!

I heard the toilet flush and then the shower run for only a few minutes and Peter reappeared at the doorway, my towel wrapped around his girth.

"Didn't have time for proper shower; just washed me cock and that.........hey get off me fuckin' clothes you dumb cunt!" he growled.

I had inadvertently sat on his shirt and shorts that were folded on the end of the bed. I quickly stood up as he swaggered over to the bed and grabbed his clothes.