Michele Nylons' True StoriesbyMicheleNylons©
For those of you who only read fiction I suggest that you go directly to my autobiographical sex stories contained later on in this essay; but what I thought I would like to do is to take a break form my usual 'physically forced' and 'caught with consequences' Transvestite sex stories and write some of my musings about Transvestism and share with you some of my real life sexual experiences.
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 the KTM 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?
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. By the way my cell phone number in Australia is 0437298234 if anyone reading this article wants to call me. 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
Michele has had intimate meetings with men, women, Transvestites, Crossdressers and transsexuals in her 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.
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!
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!
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.
I post my stories in: Fictionmania, Crystal's Storysite, Literotica, and Sexstoriespost. I also post on my own website and a few other TG sites not specifically designed just for TG fiction (or non fiction, as this is).