Michele Nylons' Stories Ch. 01

Story One - Shopping Day – Transsexual Professional Encounter – Michele's First Time

I live in Australia and, as a mid level executive, I travel a lot with my job; this assists me greatly because when I am away from home I can use the hotel room or apartment that I'm staying in for encounters and other fun activities. A few years ago I was in Sydney on business and took the opportunity to do some shopping for Michele's wardrobe. This was the period when I had made the decision to become a serious Crossdresser and acquire all the trappings I needed to lead my double life. I went to a shop in the suburbs called "Glamourworld" which specialises in providing clothing specifically for Transvestites and Crossdressers. The staff there was really helpful and I bought quite a few items including a fabulous suspender belt and matching bra set, a nice red Lycra miniskirt, and a pair of opera gloves. In a Surrey Hills church charity shop I acquired some nice second hand blouses and skirts, including a lovely white Carla Zampatti ® skirt which was my favourite for ages. (Unfortunately I threw the lot out a few years later when I had a hissy fit and vowed to give up crossdressing - but more of that later).

I then moved on to Oxford Street in the city, the gay Mecca of Sydney, and with the assistance of a wonderful understanding shop assistant bought a good quality wig; a shoulder length brunette . As it was only just after the gay Mardi Gras the shops were full of trashy tranny gear; at the Mardi Gras parade everyone wants to dress either as a Tranny or a nun for some reason! I purchased a nice pair of black high heels for only forty dollars in a shop called Pricilla's ® (closed down now I think) along with a waist cincher and some makeup. I headed back to my hotel room after a full day's shopping to check out my purchases and to dress as Michele in her own clothes for the first time.

I had been experimenting with makeup and had hit a number of transgender Internet sites for help with makeup and other crossdressing hints. I locked the door to my room, showered and shaved and went through my purchases which I had laid out on the bed. I went through what as now become my usual ritual in the transformation to become Michele. First I slid my legs into a pair of taupe sheer to the waist pantyhose; I love to wear them as a foundation garment as they do so much. Firstly they make my legs look better when I put stockings on over them; they give the tops of my thighs above my stocking-tops a nice tanned smooth look. Secondly they hold my penis out of the way and get rid of the telltale bulge without having to wear a gaff. Thirdly they just feel lovely; I think the best part of dressing is sliding sheer nylons onto my legs and pulling the gossamer panty tight so that it caresses my genitals and buttocks, I always get aroused at this point.

Next I pulled on my new black satin suspender belt and matching bra; I hadn't bought any breastforms (and still don't own any) but with my own tits (I was a bit plumper then) and some padding in the form of some bunched up stockings I had a nice chest. I opened a pair of black, seamed stockings and sat down on the bed to pull them on one at a time. As the sleek stockings slid up my pantyhosed legs the feel of the nylon on nylon sent little electric waves of pleasure into my member. I clipped the garters to the stocking tops: I loved that that suspender belt had three garter straps per leg; so much better than the cheaper two garters per leg version. I then slid on a pair of red nylon panties, becoming further excited as they snuggled against my pantyhosed arse and genitals. They contrasted nicely against the black satin suspender belt.

I sat in front of the mirror and commenced making myself up. I was still a novice in those days but using the Internet tips and the practice I had gained previously from using my wife's makeup I managed a half-decent job. After I had applied my makeup and tried on the wig; I have to say I looked quite nice.

I slipped into my white A-line skirt, a maroon top and into my high heels. By this time I was quite aroused and had troubles hiding the bulge in my panties from showing though the front of my skirt. I thought I looked pretty good as I stood in front of the mirror and of course after a while I couldn't help but start playing with myself. It was quite the sight; this heavily made up slut with her skirt rucked up and her cock in her hand, slowly masturbating herself as she rocked slowly back and forth on her high heels.

I then decided I wanted more than just a self administered hand-job and forced myself to stop. Being in the city of Sydney I knew there were plenty of Transsexual prostitutes available and decided that I would make one available for myself. As this is a true story, I have to tell you that I would love to have arranged for one to come to my hotel room and have her whilst I was dressed as I was; but the truth is that I was too scared that someone would see her come to my room. At this time, although I had been with Transsexuals occasionally before, I had never had sex with another person whilst dressed as Michele.

I phoned around (there are plenty of advertisements in the Sydney phone book) and eventually found a girl who lived at Woolloomooloo who was willing to have me come to her apartment and for me to dress up a little and have sex. As I was staying in hotel in Kings Cross and Woolloomooloo is just down the road, this was perfect, so I removed my clothes and makeup and had a shower in preparation for the night's events to follow. I decided that it was too risky for me take a full ensemble, wig, shoes and makeup with me (I was so chicken-shit in those days) but I did risk wearing pantyhose and panties under my jeans.

I arrived at the Transsexual's apartment about ten minutes after I exited my hotel. I knocked on the door and was greeted by a large, but well proportioned, caramel skinned lady in her late thirties or early forties. She was very passable and introduced herself as Tanya. She invited me into her apartment and led me straight to her bedroom apologising for not seating me in the lounge but her flatmate (another Transsexual) was home and did not like customers to linger in the rooms that they both shared in the flat. Tanya put me at me at ease very quickly; she had me seated and got me a drink and let me know it was ok to smoke as she did too. She explained to me how much she charged, that she was capable of topping or bottoming (lots of Transsexuals can't top because their hormone replacement therapy prevents them from maintaining an erection), and asked me what I would like to do and how long I would I like to stay?

I had already explained to Tanya that I liked to crossdress and went on to explain that I was wearing pantyhose and panties under my street clothes. She then went on to ask me about my crossdressing and how far had I gone with it. Tanya made me feel so relaxed that I explained my situation to her; that I had just been out that day buying all my own clothes, makeup, a wig, shoes etc. I further explained that I had never had sex whilst I was dressed as a woman but was so very much looking forward to it. Tanya said that I was silly not to bring around my purchases but that she could understand my reluctance being that I was new to the scene.

Now the next paragraph is going to sound like I made it up, but I promise you the account is factual; and if you don't believe me what do I care?

Tanya told me that she was quite excited about being with a novice Transvestite and that she was willing to do my makeup and lend me a wig; she would also provide me with a negligee and I could try on a pair of her shoes. She apologised for not being willing to lend me any other of her clothes, but of course I understood why. Tanya went on to explain that her day job was as a makeup artist and that she would make me look as good as she could make me. (I told you that you probably wouldn't believe that this part of the story is true; but I swear it is!) She also explained that it was lucky that it was her and not her flatmate who took the booking because her flatmate would have nothing to do with Transvestites or Crossdressers. I paid her for two hours of her time and got undressed feeling more excited than I had for a long time.

Tanya was bigger than me and appeared to be a mulatto of Islander descent; she had long flowing jet black hair and was wearing a dressing gown and slippers. She was wearing little makeup but quite attractive. I explained that I would like her to dress sexy for me and to wear some more makeup so that she would enhance my fantasy. She giggled and explained that my request was common and that of course she would be willing to just that; but first she wanted to feminise me.

I undressed so that I was naked except for my panties and hose; my excitement was obvious from my hard cock pushing out the gusset of my pantyhose and straining at the front of my panties. Tanya stroked me gently through my panties and pulled me to her and kissed me hard, pushing her tongue deep into my mouth. I groaned and pushed myself against her as I wrapped my arms around her ample body. She giggled and eased me away from her. Tanya realised I was close to coming already and teasingly chastised me to slow down and enjoy what lay ahead.

Tanya led me into her ensuite bathroom and sat me on a stool in front of the large mirror; she went back into the bedroom and returned with the largest makeup case I had ever seen (and have ever seen since for that matter). She started to make me up, explaining as she went what she was doing. As the case contained theatrical makeup she was able to apply a base coat of foundation that was perfect for my complexion; also it covered all of my blemishes. Next she applied a thin covering of another foundation that gave my skin a slightly tanned, even appearance. Over this she dusted on face powder which created a glowing, healthy look on my face.

Tanya went to work on my eyes applying eyeliner, eyeshadow, and mascara. I couldn't see exactly how she applied these cosmetics because she was in front of me and for most of the time she had me half-close my eyes. Tanya did explain what she was doing though, and I did learn a few makeup tricks from her. She was so adept with her various brushes and sponges and she also sometimes blended colours with her fingers; it was so obvious that this girl was an expert.

Next Tanya rouged my cheeks and put on a two-coat lipstick after first applying lip-liner. She explained how to go outside of my lip-line to make my lips look fuller; but not to go too far otherwise it looked silly; like a clown's makeup. It has taken me a long time to get even close to the way she did my lips. (You think it would be easy wouldn't you? But the only thing I find harder is putting on eyeliner.) She finished with a final careful dusting of face powder and made me close my eyes whilst she went into the bedroom again. Tanya told me open my eyes and she was standing in front of me brushing out a long, blonde curly wig. She explained that long blonde curly hair wouldn't suit me too well but that it was the only wig she had here at home. I told her about the brunette bob I had bought that afternoon and she agreed that I had made a wise choice. (See my earlier pictures at the websites in the links in above paragraphs to see if you agree; as I explained I have since lost that particular wig and now have a slightly longer and lighter wig that suits my thinner face as you can see in the more recent photos.)

Tanya positioned the wig on my head, brushed it in place and adjusted the locks over my forehead; she explained that with a long fringe, I needn't worry too much about my eyebrows and to this day I still I have never used an eyebrow pencil. Then she moved out the way and told me to look in the mirror. The transformation was amazing; I looked downright sexy with my hazel eyes glittering out the dark eye makeup, perfectly matched eyeshadow; my rouged cheeks and ruby red lipstick (still my favourite colour). The blonde curls and the longish fringe framed my face perfectly (although I agree blonde is definitely not my colour). I remember my exact words: "God I look so good; do you know what? I'd fuck me!"

Tanya laughed and said something about that not being necessary tonight and led me back into the bedroom. She mooched in her closet and came out with a pair of shiny black high heeled sandals and a black nylon long-sleeved negligee. I sat down and she helped me put on the heels which were a little big, but she joked that I wouldn't be doing too much walking in them tonight. I stood up and she eased the negligee over my head and arms and pulled it down my body; she readjusted the wig and gave it a final brushing. Tanya walked me over to her full length mirror and turned up the light so I could see myself. I was flat-chested without a bra and my tummy was too big for my liking but I still looked pretty good; as good as many of the Transvestites I had lusted over on the may websites I frequented.

Tanya told me to relax whilst she looked after herself and went out of the room briefly, returning with a drink for both of us. I sat down, lit a cigarette and practiced sitting with my legs crossed. The feel of my nylon hosiery against the negligee was working its usual magic and my semi-hard penis began to become fully aroused; I couldn't help looking in the mirror and thinking about what was about to happen tonight. I attempted to settle down and drink my drink, smoke my ciggie, and wait patiently for my first sexual encounter as Michele.

Tanya came out of the bathroom about fifteen minutes later looking absolutely stunning in her heavy, but expertly applied makeup. She winked at me and sat on the bed. She rummaged around in her bedside drawers and produced a white basque and a pair of sheer flesh toned stockings. Tanya dropped her robe and I saw that she was quite a big girl with a roll of fat around her girth and large firm breasts (of course they were firm; they were silicon). Her dark skin and her large proportions were such that the extra weight she carried did not detract from her sexiness. She was wearing only gauzy white panties which were almost see-through, and when I caught a glimpse of her large thick cock through her panties I had my first feelings of trepidation, but I was also very excited. Tanya wasn't even hard yet and her cock looked menacing!

Tanya pushed and pulled herself into the basque and expertly slid the stockings up her legs; she clipped her reinforced stocking-tops to the garters hanging from the basque and went to the wardrobe again where she emerged with a pair of white high heeled court shoes (pumps for you yanks). She sat back down on the bed and put on her shoes and then stood up and adjusted the bed-lamps to that room was infused with a soft glow. She walked over and posed in front of me with one hip thrust out and said "Is this what you're looking for?" (A line I now use with Admirers when they walk into the room to meet me for the first time.)

Tanya looked perfect, a large girl yes; but well proportioned. Being dark-skinned and wearing white lingerie, flesh-toned nylons and white high heels she seemed to glow slightly in the subdued lighting. Tanya's perfectly made up face and luscious big red lips were framed by her dark locks; I couldn't wait to kiss her again! I put down my drink and stood before her and she took me in her arms and kissed me again. She was strong yet soft; her kisses demanding, crushing her lips against mine and her tongue probing incessantly, deeply into my mouth. She pushed her body hard against mine and I felt the delicious feel of feminine lingerie rubbing together for the first time. My cock became erect in my panties and I could feel her thicker, longer member rub against mine through the layers of silky nylon and I knew that this was exactly what I had dreamt of for so long.

It was obvious from the start that Tanya was going to top; to take the lead and guide me through my first 'Tansbian' encounter. She pushed me back onto the bed and lay on top of me continuing to kiss me and hold me tight. Then she extricated one hand and slid it down my body until it rested over my member, gently caressing it through the layers of negligee, panties and pantyhose; I groaned as she squeezed it firmly. I was running my hands over Tanya's back, luxuriating in the feel of her satin basque; she sensed what I wanted to do and eased herself off me so that she lay beside me, her hand still caressing my genitals through my lingerie.

I moved my hand to the front of her body and stroked her tits through the basque, feeling her nipples harden; but I didn't linger there. I could play with breasts anytime I wanted to; I wanted to explore between her legs. I slid my hand further down her body until I was stroking the top of her nyloned thigh; god it was so exciting, then I couldn't wait any longer and I pressed my hand against the package she had trapped inside her panties. I stroked her thickening member through her gauzy panties and felt the coiled snake begin to stiffen and its girth expand; this was the first time I had felt another cock and I was thrilled; my own penis hardened.

Tanya rolled onto her back and lifted her hand to my head and firmly began to push my head down her body; I knew what she wanted me to do and I was excited at the prospect of sucking my first cock. I kneeled on the bed and moved my head down her body, kissing her ample form as I went. We ended up top and tail on the bed with Tanya lying on her back and me kneeling over her. I moved my lips down to her groin and a musky but pleasant scent invaded my nostrils. I kissed her tumescent penis through her sheer panties and my excitement mounted further. Tanya groaned "Suck it baby," and I eased her panties aside and confronted my first ever hard cock.

Tanya's cock was considerably bigger than mine; it was about eight inches long but the girth of her weapon was what impressed me the most. It was thick, veiny and the glans were bulbous and a deep purple colour. I lowered my lips to the exposed member and licked along the shaft, slurping my tongue around the sensitive spot at the base of the glans. Although I was experiencing my first head job; I knew what I liked and mimicked what women had done to me. It seemed to be working ok because she groaned and again took my head in one hand and her cock in the other and pressed my lips to her manhood. Again she uttered "Suck it for me honey," and who was I to argue. I wrapped my lips around the swollen head and sucked about three inches of her penis into my mouth.

The member felt spongy and alive, it was warm and tactile; I loved the taste and feel of it in my mouth; I knew then that I was a born cock sucker and that I had not been mistaken when I fantasised that sucking cock would be wonderful. I moved my mouth up and down on Tanya's cock, sucking it and lashing my tongue around the head as I did so. I kept this up for a few minutes and she groaned and writhed as I did so; I knew from her response that I was doing ok for my first effort at fellatio.

Tanya then placed both her hands on my head and began to force my head further and further down on her cock as she fucked my mouth. The rampant member filled my mouth and I had trouble breathing through my nose and when it struck the back of my throat I started to gag and had to quickly move my head away as I choked and sputtered. I apologised and reminded Tanya that it was my first time; Tanya apologised also and told me to take a break and then to start again when I was ready and to just take as much cock as I could comfortably suck on. She was definitely in control but very considerate. Then she reached out and pushed my panties aside and slid a sharp fingernail into the crotch of my pantyhose and ripped a gaping hole.