Chapter 1

Introduction

To set the scene, I am a forty-something, married, businessman who also happens to be a part time Transvestite. That is I like to dress like a woman and experience sex with men, other Transvestites, Crossdressers and women. I do NOT want to be woman, I don't stay dressed as a woman all day every day, nor am I interested in sex with men unless I am dressed as a woman. I used to consider myself a 'Crossdresser' until a few years ago. To explain; that means I used to dress in female clothing, which I had acquired here and there, and wear a bit of makeup occasionally, but made no real effort to feminise myself when dressed. I started to really like what I was doing and got turned on and started to fantasise about having sex whilst dressed and I spent a lot of time looking at TG websites on the web. After a year or so I got serious and bought my own clothes, shoes, wigs, etcetera, and put some effort into learning to use makeup and to feminise myself whilst dressed and I also lost some weight. I now look quite passable (in my humble opinion) as a Transvestite, that is to say I no longer look like a bloke in his wife's clothes.

I have always had a fetish for nylon stockings, pantyhose and lingerie and this eventually grew into transvestism in my late thirties. I had had numerous sexual experiences with my nylon and lingerie fetish, including a few encounters with Transsexuals, but I never experienced sex with a man until I became the Transvestite, Michele. Before I tell you of some of my encounters; I thought I might share with you some musings and inspirations that I have. Even though I have only been 'active' as a Transvestite for a few years and am 'in the closet', I believe that some of the following is worthy of discussion and would welcome any responses to my email address.

Clothes & Makeup

I discuss clothes and makeup at some length in my Yahoo Group and provide some advice to beginners and closet TVs and CDs. One of the main things that I think attracts men to Transvestites is the way we dress and make ourselves up; we wear the sort of clothing and makeup that mature men find exciting. I have to say that most of the women's fashions today are not to my taste; too many pant suits, shorts, midriff tops, and sensible shoes. The makeup is bland and natural skin tones rule. Well fuck natural! Bring back ruby red lipstick, black eyeliner and mascara, coloured eyeshadow and high, rouged cheekbones; bring back the eighties makeup style I say!

Mature men (at least the type I fancy) like short skirts, high heels, stockings, pantyhose and silky blouses; not jeans, shorts, long peasant skirts and pant suits in boring shades of brown. Living in a hot climate like Australia makes it even harder to spot a girl dressed the way I like them because most of the women dress casually, if not downright daggy. I'm convinced the national dress for women in my country is becoming khaki shorts, tank tops and flat sandals.

My only advice in this essay to Crossdressers who are just starting out is to look at the pictures of Transvestites on such websites as KTMGirls, TVChix and other quality Transvestite places on the net. You will find that the better (more convincing) girls pay attention to detail and match their wardrobe and wear heavy makeup, but take the time to apply it so that it looks professional. There are some great websites with good advice on makeup but most advice in women's fashion magazines does not suit male skin types and again tends towards the more conservative natural look of today. It takes time and practice sure, but just go out and buy some cheap makeup and practice until you get a look that suits you. Except for lipstick (I use a two coat, Max Factor EverLites ®, because it stays on during heavy kissing and fellatio), otherwise all my makeup comes from the $2 shop. If you want to see my progression from tubby Crossdresser to sexy Transvestite look at my page in my Yahoo website; it took me about two years to get a look I'm really happy with.

I used to have a large wardrobe or clothes, makeup, shoes, lingerie and accessories until I threw it all out in a hissy fit and vowed never to crossdress again after a bad experience with an Admirer (which I will tell you about later). An Admirer for those of you who do not know is a man who finds Transvestites and Crossdressers to his taste. I now find that I can get by with a smaller wardrobe that I can mix and match and with the makeup and accessories that I find suit me best. I do occasionally buy clothes off the rack in department stores but I get most of them from Opportunity and charity shops.

Should A Girl Wear Pantyhose Or Stockings?

Both!

Arranging Encounters And Risk Management

The most exciting but also the most dangerous part of being a bisexual Transvestite is arranging meetings, especially when you first start 'playing the game'; for me it is doubly dangerous because I am married and 'in the closet'. I advertise my availability on transgender websites, matchmaking websites (such as ALT.com, Adult Matchmaker etc) and occasionally in local sex shops. I am contactable by email or cellular telephone. (God, how did trannies meet before the internet and mobile cellular phones?) I keep my hotmail account separate to my other email accounts and my 'Michele-phone' is never used for any other purpose; that way I can ensure that Michele never enters into my 'real' life. If I am contacted by email I prefer to exchange pictures and if possible to chat online before meeting. I always insist; I mean ALWAYS INSIST on talking to the potential playmate on the phone at some length before a meet. I have found that when talking to someone on the phone you can usually tell if they are sincere and more importantly if they might be dangerous or a potential loony. It's not foolproof, as I can testify, but it works for me more often than not.

To start with I refuse to meet with anyone under 35, most Admirers and other TVs tend to be older anyway but young men are often still confused about their sexuality and are usually the ones who waste my time. Being a Transvestite (I'm sure other 'active' girls reading this will agree), the reality is that you are plagued by timewasters; men who send you emails or call you up on the phone looking for a meet but never show. They either chicken out or just get excited looking at your pictures and talking to you. Nothing pisses me off more than getting all dressed up and sitting there waiting for the phone to ring to pass on the address where we will meet and then ending up being stood up. It takes me from one, to one and half hours to transform into Michele (read my stories to see the ritual I go through to transform — the ritual is pretty much the same in all of my stories and that's what I do in real life) so to all you timewasters out there; go to any of the websites listed above, look at my pictures and have a wank; don't call me for a meet unless you really want to!

Once I have established trust I will then arrange a first meeting; always at a place of my choosing. I am fortunate enough to have a discreet address that I can sometimes use, or I may use a hotel room. I never meet at an Admirer's place for the first meeting. I also never give out the address of the meet until I am dressed and ready to receive the punter; I have the suitor call me to arrange the meet, get dressed, and then provide the address by phone when I am ready to receive him. Another thing that some of you Admirers need to get into your heads, is that I do not sit around 24 hours a day dressed as Michele waiting to satisfy your sexual fantasies; I lead a busy life and Michele's antics have to be fitted in around it, and then only when I am in the mood. So many punters ring up out of the blue and expect you to meet them right there and then!

I always insist on a return phone number too. If the caller rings on a 'Private Number' cell phone or from a public phone box he is shit out of luck as it's just too risky. I don't want to know too much about a punter or another TV (except that they are clean and disease free), they can use false names if they like; but I at least want to know that I can call them to call off the meet if necessary and it's also another way to verify their bonafides.

Some Transvestites and punters like to meet in a public place like a bar or café first and I can understand why; but I never meet Admirers unless I am fully dressed and made up. I am lucky that when I am Michele I look nothing like my male counterpart. I never ever, ever, ever, meet Admirers whilst I am dressed in drab (as a man), as I do not want to meet a punter at a social or business function and be recognised. I will, and have met other Transvestites at their place though, and of course I have to go there in drab and dress at the venue. In this case the other Transvestite is taking most of the risk initially so I don't mind. My advice to closet TVs and CDs who are yet to meet 'playmates' but yearning to so, is to do the best you can to ensure your safety, and the discretion and sincerity of the other party before you meet; especially when meeting male Admirers for the first time.

Sex With Men Women Transvestites and Transsexuals

I have had intimate meetings with men, women, Transvestites, Crossdressers and transsexuals in my short but exciting career. There is nothing more erotic than kissing another Transvestite; as your soft lipsticked lips mesh and your hands disappear under each other's skirts and slide up stockinged thighs; it's just the best. So sex with another Transvestite is my favourite; although I also love to be treated as a woman by mature male Admirers. I think the other reason men like Transvestites is the old adage that "men know what men like" is true. Transvestites dress and wear makeup the way men fantasise that women should, and also Transvestites know exactly how men like to be turned on and how to satisfy them; well in my humble opinion anyway.

I have been with transsexuals, but only 'professionals' (prostitutes) and in my experience, except for prostitutes, transsexuals really don't have much time for Transvestites anyway. I have included an encounter I had with a transsexual in the true stories section later in this essay. Michele has also been with a woman; again a prostitute, and again I have included the interlude later in this essay. I do like having sex with women whilst I am Michele, but as a Crossdresser, unless you have an understanding wife or girlfriend your only recourse to have sex with woman whilst you are dressed may be a professional lady.

Top or Bottom?

When meeting someone for the first time I always ask if they prefer to top or bottom. I prefer to bottom and I do have an opinion as to general rules of thumb based on my experiences. Transvestites usually like to bottom, but when together are usually very compatible and will often change roles from top to bottom and back again during a sexual encounter. I have one Transvestite girlfriend who prefers to remain the top or bottom throughout an encounter and then we change roles when we next meet. I have only been with a couple of women, but they were also willing to bottom or top; I prefer women to top as I can always have a woman bottom in my male alter ego. Most men that I have been with start out topping and some prefer to top only; but increasingly I find that they like to get a good fucking and are seldom averse to sucking my cock (I refuse to refer to my sex organs as a "my man clitty" or "my ass pussy" and other such nonsense). When men play the submissive role they will tend to 'top from the bottom' if you know what I mean (that is they remain the dominant partner) even when being fucked or performing fellatio.

Professional Care

I have had satisfactory sex with prostitutes; both transsexual and female, but my one encounter with a male prostitute was a disaster. He wanted me to undress and couldn't understand that I only like sex with men whilst I am dressed as a woman. He couldn't keep hard because I was a woman as far as he was concerned, and as he was gay, he could only have satisfactory sex with other men. Although flattered that I was woman enough to turn off a gay man; it didn't do much for my sexual frustration. For those girls out there still in the closet and that are yet to have their first sexual encounter as a Crossdresser, an understanding Transsexual or Transvestite prostitute is probably your safest bet; also there is less worry about discretion or safety.

Kissing Sucking and Fucking

I love kissing; it is just so much the best foreplay! I have yet to have an encounter where I didn't get involved in heavy petting and kissing before engaging in sexual activity. Even those men I have met who were having their first time with a Transvestite have enjoyed kissing me. A word of warning here to beginners, always ensure you shave as close as possible before applying your makeup when you are about to have a meet. Nothing is more off-putting than kissing a Crossdresser with a 5 o'clock shadow; make sure that you get every skerrick of hair removed off your face, especially around lips; run your fingers all around your face and if there is any rasping at all, shave again. And for god sake trim your nose hair!

Fellatio is probably the stock-in-trade for most Transvestites; I won't bore you with techniques as most of you will have your own tricks. I like to 69 of course but I sometimes find that being fellated interferes with my concentration when I am sucking. My favourite position is, like any good girl, on my knees sucking a hard cock and looking lovingly up into my lover's eyes. Most Admirers love this and will reward you with a mouthful. Another position Admirers like, is them lying on their back whilst you straddle them top to tail so that they can look up your skirt whilst you fellate them. When I am with another Transvestite I prefer to take turns fellating each other rather than 69.

I love it when the other person comes! Yes I swallow; if you haven't tried it don't knock it! I also love it when my partner comes on me; I love it over my face and love to see semen spattered on my skirt and stockings. Just one thing for those of you who have never swallowed; yes it's true that just like in my stories the penis you are sucking on will throb just prior to and during ejaculation; but when he comes in your mouth it feels like your mouth is just flooding with come, you can't actually feel the individual spurts in your mouth as I describe in detail in my stories. Also semen is not salty; as it is so often described in fiction, it is actually a bit starchy but quite pleasant to taste. Obviously the subtleties of taste vary from man to man.

Ok the truth; fucking hurts! The first time I let myself be fucked it took me ages to get relaxed enough to get a cock inside me and then it was only achieved with a little pain and lots of lube. Ok the truth; fucking is ecstasy! Once I get a cock into me and I am suitably lubricated I just love being fucked; I can come whilst being fucked without even being touched down there; in fact sometimes I come almost straight away and then again a second time if the fucking lasts a while; I don't even have to be hard! The advice I offer here is make sure you take it slowly, especially the first time (I don't care if you regularly ram a dildo up your arse; the real thing invokes a different mindset and you will have to concentrate on relaxing) and use as much lube as possible. Always make sure you are clean down there and of course: "If it's not on; it's not on"! My preferred position is on my back looking him or her in the eyes, although a good dose of 'doggy' in front of a mirror is also a real turn on. I also like to ride him sitting down or to be taken from behind whilst standing and leaning over a chair or table. Oh lets just face it; I just love to be fucked any way I can get it!

Group Sex

I have had the pleasure of several group sex encounters at both Transvestites only, and also Transvestites and Admirers parties. Group sex parties are not easily arranged but are well worth the effort. The good thing about having many people engaging in sex is that you can experience all those fantasises that us girls dream of: sucking two cocks at once, sucking a cock whilst wanking another, giving and receiving oral pleasure etc; the list goes on and is limited only by your imagination. You will note that in just about all my stories (Be Careful In The Park, Lady In The House, Michele And The Predator, My Brother My Sister, etc) contain at least one group sex scene.

Another good thing about group sex is that most of the participants will be at various stages of stimulation ranging from arousal to orgasm to recovery and on to arousal again; this usually ensures there are enough hard cocks to keep everyone satisfied. This is particularly the case when there are several Transvestites who usually prefer to bottom; it is to the satisfaction of all participants when roles can be shared, reversed. Also once you achieve orgasm, you can take a rest whilst someone else satisfies the person who just satisfied you without feeling guilty.

The only drawback I can think of at a group sex party was when there was a Transvestite present who was more attractive and feminine than the others, and initially most of the punters wanted to be with her and were not as attentive to the other girls present. The situation soon resolves itself though; as men being men, their sexual desires overrode their patience and soon everyone was happily servicing or being serviced.

Of course there are some risks involved in group sex, especially when meeting Admirers for the first time, but the risks are mitigated when there is more than one Transvestite present (there is safety in numbers girls). My preference is to meet in a nice big hotel room and for the girls to get there first. That way I can dress, makeup (again you note my rule of never meeting Admirers unless I am dressed and made up), ensure I look as feminine as possible and have a drink and a natter with the other girls before the Admirers arrive. I find this is more relaxing, far less risky, and of course better for the Admirer who does not need to see 'Steven' transform into 'Stephanie' before his eyes; far better for Admirers not to know all of our secrets girls!

True Stories

I will now go on to tell you about a few of my (Michele's) experiences, encounters and adventures. I'll break them up into small vignettes and set the scene at the beginning of each short story; I hope you enjoy reading about them as much as I enjoyed having them (well most of them). They are all factual, true experiences; of course some (not all) of the names and places have been changed to protect both my male identity and the identities of the participants. Anyone who reads these stories and recognises themselves (they are all set in Australia so if you are not an Aussie; sorry hun, it didn't happen to you) and not happy with the way you were portrayed can contact me by email or phone and I will remove the story from its parent site or correct the story as appropriate.

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 and panty 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 bob. 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 used to love to wear them as a foundation garment as they do so much. Firstly they made 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 trouble 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. 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.