Almost all crossdressers start by dressing in the complete privacy of their own homes. Many are happy to stay that way, but others want to venture further afield, stepping out into the wide world of everyday life.
That first outing can be a terrifying, but exhilarating, experience. Are you going to be read, and if so, what could the result be? Where should you go, and what should you do?
Your very first time cross-dressed in a normal, everyday environment will be like no other, and once you have done it successfully you will have the courage to do it again and again. It will open up a completely new world.
For this reason it is worth going to special lengths to make sure your dream doesn’t turn into a nightmare. You will have enough to worry about without getting lost.
1. Plan out where you are going to go, how you are going to get there, and how you are going to get back.
Going Out In Daylight…
Fledgling TVs often making the mistake of choosing places where there are few people around, while in fact there is more safety in numbers. You are less likely to cause attention in a busy shopping street than in a quiet park, where mothers with children could misunderstand your motives.
If your first outing is to be in daylight, head if you can to a city centre and choose the more affluent shopping areas. Here you are more likely to be amongst people who are too polite to mention your appearance even if they spot something amiss. Avoid areas that are frequented by gangs of bored teenagers looking for something to do – or someone to jeer at.
It’s well worth rehearsing your trip before you make it. Going by car, if you have one, is obviously favourite as buses and trains can add to the strain, but if you have to go by public transport find out the times so you’re not stranded for 20 minutes in the rain. This can play havoc with your wig, your make-up and your nerves.
Unless you want to chat with a car park attendant, go for pay and display or an automatic multi- storey. Its worth queuing for the right spot and never take any risks with parking – you won’t be the first transvestite to have to go to the car pound to pay the towing-away charge, but believe me, it’s not fun.
Parking is obviously easier in small towns, but here you run greater risks of embarrassment. Seasoned TVs might get a buzz out of shocking Chipping Sudbury, but provincial policeman may take more notice of you than the city forces who have seen it all.
…Or After Dark
Some TVs I know just enjoy driving around in their cars, but this just seems an extension of the closet. If you are going out, you want to head somewhere and do something. But what?
Whatever you do, don’t hit your neighbourhood streets for a stroll at two o’ clock in the morning. This may be tempting, you’re all dressed up and it’s just out there, but it really is the silliest plan of all. If you look good, patrolling policeman are going to wonder what a woman is doing out alone at that time of night. Passable at first first glance, you could be still be done for soliciting.
There are various transvestite groups who meet here and there about the country, in venues ranging from someone’s front room to the upstairs of a gay pub, but again it very much depends on where you live. However most large towns nowadays have a gay pub or club, somewhere. It’s well worth sussing out the local scene first, as a man, to see how the land lies.
Transgender Resources…Into The World As A Woman, By Annie Clarke
2. If you want to pass successfully as a woman, make sure you look the part
When you’re dressing up in your dimly lit bedroom, it’s easy to think that the more make-up you apply, the greater the transformation. Inch thick panstick, bright blue eye-shadow and a wide swathe of red lipstick and Bob’s yer Auntie, you’re away. You might look like your own perfect little fantasy in the mirror, but on the street you’ll appear ridiculous.
Dress as other women will be doing around you. Wear light make-up during the day, but always enough to cover your beard shadow, and you can afford to go heavier on the eyes at night.
Your make-up is all-important. It takes practice to get it right and it’s always worth getting a second opinion. You will get good advice and help from the girls at Transformation shops nationwide.
Choosing Your Outfit
Do try to blend in with your surroundings, unless outright exhibitionism is really your game. If the average woman in Debenhams wore a tight pvc mini skirt and six inch heels, you could as well. But they don’t.
Dress your age. You can be chic as you like, but a middle-age woman tarted up as a teenager attracts sniggering without the added incentive that she is also a man.
Remember, the mast majority of people won’t even notice you unless you’re of an unusually large build. Those that do will seldom give you a second glance if there is nothing that particulary strikes their eye.
3. Things to avoid
Ladies loos – the one place you really are risking trouble if you’re read. You’ll get away with it in gay pubs, but the best advice is to avoid them whenever possible.
Breaking the law – don’t drink and drive, or do anything which could bring you into conflict with the police. If you behave yourself, you should have no problem at all from the boys in blue, and especially their female colleagues. Don’t give them any reason for taking you down to the station, because there you could find their liberal attitude is just skin deep.
Kids – Children are the worst challenge you will face. Young ones lack their parents’ social inhibitions and can call a spade a spade, or in your case, a man a man. Their parents will also be in protective mode, and could over-react to a “pervert” being near their kids. Places like McDonalds are not recommended. Older children, especially in gangs, are even worse and can easily take it upon themselves to follow you for something to do. A TV aquaintance of mine recently had to seek help from a policeman because a pack of 15 year olds chased him through Manchester’s Arndale Centre on a saturday afternoon. It does happen, and he always thought he was totally convincing.
Acting like a man – remember you’re a lady, and don’t let your inner masculine self dominate your commonsense. Ladies don’t walk the street at night on their own, and may be thankful if a police car stops and asks them if they O.K.. You won’t be so glad of it. Ladies on their own may eat in restaurants or drink in bars nowadays, but they are still few and far between and are likely to attract unwelcome attention. Unless you want to be chatted up by amorous waiters, stick to the gay areas of town for eating and drinking if you can.
Above all – take care and you should enjoy yourself. Once you have done it once, and felt the breeze waft your skirts, you’ll want to do it again. It’s a free country and why shouldn’t you – so long as you don’t upset other people, they shouldn’t trouble you. The rest is all down to confidence, which only experience will bring. Go for it, and have fun!