To set the scene, I am a middle-aged, 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 I 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".
Now; before I get all the feedback about most crossdressers being heterosexual and that they don't dress for sexual stimulation, I concede the point. I know a few crossdressers who don't dress for sex and belong to an organisation called "The Seahorse Club", a support group for crossdressers. I also know some of these individuals have "come out" to their wives, who tolerate, and in some cases, support their husband's crossdressing peccadilloes. I also know a couple of crossdressers who profess to be hetero card-carrying members of the Seahorse Club who secretly cant wait to get down on their knees and suck a nice juicy cock!
There! I said it!!! May my stockings forever ladder if I'm telling a lie!
Before I tell you of some of my encounters in the series of short stories I have written (surprisingly titled "True Stories"); 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.
So why do men prefer transvestites! Well; let me sum it up for you (if you are homophobic, now is the time for you to hit the return key or close your browser on this page — although most admirers don't consider themselves homosexual and neither do I — I'm just SEXUAL).
We like to wear sexy clothes and heavy makeup!
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. Most women's fashions today are not sexy at all; too many pantsuits, walk-shorts, midriff tops, and sensible shoes. Too much khaki, boring dresses; and what the fuck is going on with the bare-leg brigade! It's like there is a crusade against hosiery out there! I'm fed up of seeing women with lily-white legs with splotches and blemishes that would look stunning encased in a pair of sheer stockings or pantyhose! Women also wear bland makeup with natural skin tones. Well fuck natural! Transvestites wear ruby red lipstick, black eyeliner and mascara, bright-coloured eyeshadow and rouged cheek. We like short skirts, high heels, stockings, pantyhose and silky blouses; not jeans, shorts, long peasant skirts and pantsuits in boring shades of brown.
We keep our high-heels, stockings, lingerie and makeup on during sex!
I don't know how many times I've been out with an attractive woman dressed in sexy clothes, makeup, heels and hosiery; only to have her insist on coming to bed with her face scrubbed clean and then covered in moisturiser. Usually dressed in a frumpy cotton nightgown, bed-socks and with her hair tied up. What a turn off! If you ask a woman to leave on her stockings, heels and makeup she will usually accuse you of being a perv or treating her like a whore! Transvestites always leave on their makeup, heels and hose during sex.
We like to be groped and fondled!
Transvestites call Admirers, admirers because we like to be admired! This includes being groped, fondled, stroked and kissed. Unlike women who complain that men only want 'one thing' and see them only as sex objects; transvestites are exactly that — sex objects!
We really like to suck cock!
Now it's true that I have had the odd girlfriend who didn't mind giving me a bit of head; but it's not the same as having a heavily madeup, perfume-wearing, stocking-clad, mini-skirted, transvestite lovingly sucking on your cock like it's an all-day sucker!
We have the same sex drive as men!
I read somewhere that men think about sex about a hundred time an hour (or was that a day)? Anyway; men think about sex a lot and only have to glance at a nice set of legs, a tight arse, or set of big tits to get horny. Women on the other-hand mostly equate sex with romance and don't generally go around like randy baboons like men do. They have to fancy a guy before they will put out for him. Transvestites (being genetic males) think about sex all the time and as we have a nice set of legs, a tight arse of big tits we like men to take advantage of them and so long as they are clean and polite we generally don't care what they look like!
We like anal sex!
Well most of us anyway! Again, I have one girlfriend who really liked anal sex and a couple that would grudgingly allow it. Most (not all) TVs love to be anally fucked (its not like we can fuck any other way is it!). But really do enjoy it as long as the person fucking me is clean, gentle at first, and of course wears protection.
Now a few of my musings on being an amateur part-time transvestite
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, Gaydar, TVChix, 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 exciting transvestite 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 one of my true stories. 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 dressed as Michele, but for most crossdressers, unless they have a very understanding wife or girlfriend, their only chance to have sex with woman whilst dressed may be engage a professional lady.
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