A crossdresser's first night out is an important rite of passage. But it's a daunting step to take. It should be a wonderful occasion, but it can be quite stressful if things go a little wrong. So it's important to plan carefully and not be too ambitious.
As a crossdresser who has made that first trip out, I thought I would give out some advice to those girls who are planning their first steps out.
Where To Go?
a. Transgender Meetings
I would strongly recommend looking for a transgender event or meeting to attend for your first night out. There are many of these taking place up and down the country. They offer a safe and welcoming environment where transgender people can meet and socialise.
Some of these are discos or dances, and some are events where you can just sit and chat with other transgender people and sometimes their partners. These events are usually held on a monthly basis. Usually they are held in community centres, village halls or function rooms. You will be well looked after at these events. Especially as a first timer. These kind of events don't allow admirers to attend, so you're not going to be pestered by men demanding your attention if you're a trans woman or crossdresser, or vice versa if you're a trans man. You can find these events by searching on Google for trans friendly groups or support in your area.
Do make sure you check what kind of trans people they cater for though. Some are aimed just at trans women and/or men, rather than crossdressers. Others are more inclusive and cater for anyone on the transgender spectrum who dresses and presents as the opposite gender.
Be sure to check out what kind of clothes you can wear. Some frown on or forbid the wearing of fetish clothes. Others are fine with any clothing. Some might even allow you to attend in your usual gender attire for a first night, so you can gain confidence before attending in your preferred gender expression on future attendances.
Please don't attend these kind of events in the hope of finding any sexual encounters or hook ups. That's not what these events are about.
Some of these events have a dressing and clothes storage area, so you can turn up in your usual gender clothes, and then change and do your make-up etc, at the venue, which is ideal for those in the closet, or those who don't feel confident enough to travel to the venue dressed in their preferred gender expression.
My first time out was at a monthly event held near Southampton, called the Totton Disco. It catered for anyone who was transgender and dressed fully in the clothes of opposite sex, so trans women and crossdressers were welcome, along with their partners if they wanted to attend. It had facilities to change and do your make-up and store your drab clothes for the evening. No admirers were allowed in. It was a very safe environment to enjoy an evening dressed en-femme in the company of others doing the same.
b. Organised Transgender Events
These are organised transgender events that take place in a more public place than the kind of meetings I have described above. These events can be monthly, or held less frequently, including one that is very well known which happens annually. Some of these events take place in one venue and others are across several participating venues. They cater for anyone who is transgender and they don't have any restrictions on things like hooking up with someone, although it is important to note that the venues are not sex clubs and any liasons that involve sexual activity, should take place in the privacy of wherever you are staying.
A very well known event of this type is Leeds First Friday, which unsurprisingly happens in Leeds on the first Friday of the month. This event takes place across a number of different LBGTQ+ venues in a safe area of the city. There are organisers who will meet and greet first timers and look after them, so they have a good time and stay safe. You are out in public, rather than in the controlled environment of a Trans only meeting. So you may come across members of the public and also admirers, but if you don't want their attention then a polite "No thank you " will see them leave you alone. And if you have any issues there are plenty of other trans folk around to look after you, including the event organisers.
Another good event is The BNO (Big Night Out) which takes place on a Friday once a month in a very accepting LBGTQ+ nightclub in Milton Keynes called Pink Punters. This is a very safe place to attend with good security on hand to keep you safe, should you need them. I have attended a few transgender events at this venue, and I can vouch that it's a safe venue for newbies. If you attend on a BNO night, there will be plenty of other transgender people to mingle with. There is a hotel situated just across the road, so if you stay there, you can get changed, have a meal in the restaurant and then head across the road to the club, for a night of socialising and dancing. And whenever you feel you're all partied out, you can just stumble across the road (don't forget the Green Cross Code) and crash out in your hotel bed.
Every July an annual event takes place in Manchester called Sparkle. This event is centred on a park adjacent to the Gay Village around Canal Street. It's a celebration of everything trans and has organised events taking place in the park during the daytime, and then socialising taking place in various LBGTQ+ venues in the Village during the nighttime. It's a very safe environment to be in, and would be very suitable for a newbie wanting to attend their first event. You may have to travel in public from your hotel to the venue, but there are so many trans folk doing the same on Sparkle weekend that no one will give you a second glance.
So if you've decided on a potential venue, then on to the next step towards a great first night out.
Contact, Planning And Research
You want to find out as much as you can about the venue you will be visiting for your first night out, so you know roughly what to expect and things go smoothly.
Find the details of the event organisers and send them a message explaining that you are new to the scene and this will be your first night out. They will be very helpful, put your mind at ease about worries or queries you may have, and they will be primed to keep an eye out for you and then welcome you and guide you in the right direction on the night. Make sure that you know how much you have to pay to gain entry to the venue, and if they take card payments or just cash. If it's the latter make sure you get the cash before you set off. Don't plan to go to a cash point on the way to your night out, in case it's run out of money.
Decide how you are going to travel to the venue. Public transport or driving. If it's the former, are you ok with travelling in public while dressed? How much are the tickets? And very importantly what are the bus or train times? You don't want to miss the last ride home. Also have a contingency plan in case things go wrong, such as a cancelled train or a broken down bus. Can you afford to take a taxi if required? If you are driving, then plan a route. Find out where you can park, as close to the venue as possible. Can you drive in 6 inch heels? If not wear a pair of shoes you can comfortably drive in, for the journey, and put the killer heels on when you arrive.
Consider if you need to stay overnight in a nearby hotel. Often this is a good idea, because you can get made up and changed in comfortable surroundings and you can have a nice relaxing night as you come down from the excitement of your first night out.
If you are on social media or a member of any TG forums or groups online, then why not see if anyone you know is going to be attending the event you are planning on attending? Then you will have someone to buddy up with for your big night.
Once you have checked out where you are going to be making your debut onto the scene, it's time to focus on your outfit for the event.
What To Wear?
What you choose to wear is entirely up to you. But do make sure you have checked if there is a dress code for the event you are attending. If they say no fetish wear, you will probably be turned away in a pvc mini dress.
I'd suggest going for an outfit that you look pretty and fashionable wearing, but don't aim to be the belle of the ball on your first time out.
The most important thing about the outfit you wear is that you feel comfortable in it. So your choice of underwear, and outer clothes should be something you have worn before and felt comfortable in. Nothing is worse than something feeling tight, or chafing or too loose and slipping off. You will not be able to focus on enjoying yourself if you are having a wardrobe malfunction. Make sure you take your time getting dressed. I know one girl who rushed getting dressed on her first night out and went out with a twisted bra strap which caused her chafing and pain and she had to have an unscheduled undressing in the bathroom to correct it, but spent the whole evening in discomfort.
When it comes to your hosiery, wear what you are used to. If you normally wear stockings and suspenders then go with them, but don't wear them on a first night out if you haven't worn them before. They take a little getting used to, especially getting the perfect tension in the strap adjustment. You don't want to spend the evening constantly fiddling with your stocking tops.
Hold up stockings, also known as Thigh highs, are a good easy alternative with one important caveat. They can be unreliable. Quite simply hold ups are prone to suddenly not holding up. So I would suggest wearing a brand new pair of a make and type that you trust. I used to carry a spare pair in my handbag and I have had to use them a couple of times, when my hold ups have decided to become fall downs. These days I have a new secret weapon. An adhesive that comes in a small tube that you can apply to the stocking line on your thighs and stick the wayward hold ups into position. It's low tack and comes off easily, so don't worry about having superglued your stockings on. But it's tacky enough to keep hold ups, up. Tights, or pantyhose as they are sometimes called, are a safe and dependable option to wear. Not as sexy as stockings, but they aren't going to fall down. No matter what I'm wearing on my legs, I always carry a spare pair in case I ladder them, but it's not essential that you do. But as I said, do be wary with hold ups and carry a spare pair or some stocking adhesive.
The most important item of clothing that you need to consider very carefully is your footwear. The wrong footwear can ruin your evening. The first consideration is, can you walk in your chosen shoes or boots? If you can, have you ever walked up or down stairs in them? I once came out of my first floor hotel room and walked to the stairs, where I found my friend, three stairs down, clinging to the bannister for dear life, wearing 6 inch stiletto heels. She had practiced walking in them, but forgot about going up and down stairs in them. I had to sit her down and take them off of her feet, so she could go and put on something she could walk in. And she had been planning to dance the night away in them! Make sure that your shoes fit you well and are properly worn in. You don't them rubbing or pinching and causing blisters. Practice walking in them, including up and down stairs. Unless you are wearing flat shoes, you will probably have aching feet at the end of the night, but that applies to many cisgender women too. Women's high heels place the feet in an unnatural position, so they cause aching feet. It's almost a badge of honour amongst girls. Aching feet from dancing all night in shoes that look fabulous. But shoes that cause blisters or broken skin are no fun at all. And heels you struggle to walk in, are no fun either and can be dangerous. Remember walking up and down in your living room is not the same as being out in the real world with uneven pavements, gaps between slabs and steps to contend with. One friend of mine suffered a very nasty knee injury because of the high heels she was wearing. So go with what you know and can trust when it comes to shoes and boots.
Be Weather Prepared
Don't forget to consider the weather, and if it's going to be cold or wet, you will need a suitable jacket or coat. When you get to the venue you can check it into the cloakroom if there is one, or hang it up somewhere. Even put it on the back of your chair. But don't get caught out by the weather without a suitable coat. Anyway coats are gorgeous so find a nice one and look fabulous. A small umbrella that fits into a handbag is a useful accessory too.
So you have got your venue chosen, you've done your research on where you're going and you've chosen your outfit. Next think about what you will need to take with you. And how you will carry it.
Your Handbag
Welcome to the fabulous world of handbags. Possibly the most wonderful accessory ever created. They are just so gorgeous. And of course, practical. It's up to you if you want a shoulder bag, an across the body bag or a traditional hand held bag. Women's bags are just amazing, but forget the aesthetics for a moment and consider what you will need to carry in it. And then try and find the most fabulous bag you can, but more importantly make sure it is big enough to carry everything that you need.
So just what will you need to carry?
First of your keys, car and house, unless you are staying in a hotel within walking distance or using public transport. Then you can leave them at home. In that case you will need the hotel room key. These days that's usually a card, but I have still come across old style keys, on a ridiculously big fob in some hotels.
Also your mobile phone which is very important these days. If you are taking a separate camera, then don't forget that.
You will need to carry a lipstick that matches what you are wearing on your lips and a small compact foundation powder in a shade the same as the foundation you are wearing. Then you can make sure you can stay looking flawless all night. Don't bother taking any eye makeup or anything else. You won't need it
A small packet of tissues. Always useful to have for a number of reasons. You never know when you might suddenly sneeze or a waft of pollen makes your nose run.
Wet Wipes. I always carry a few wet wipes with me. I use a packet of wet wipes to remove my make-up and when I get to there being half a dozen wipes left, I start a new packet and put the half dozen to one side to pop in my handbag. You won't need more than that. They are useful to have if you need to clean your hands or anywhere else.
A toothpick. A small but useful thing to have if you are going to be eating. Then when you go to the bathroom you can check in the mirror that you don't have spinach or anything else in your teeth.
A purse or wallet. This should contain your credit/debit card, and some cash. Make sure you have a few coins in case you need to use them in a parking machine/meter. It's also a good idea to have some form of photo I.D in there, such as your driver's licence. I know that you will possibly be presenting a lot differently to how you look on your licence, but it may be needed for age verification to enter the venue or be served at the bar. Don't worry about having a male I.D and being dressed en-femme. Those who need to see your I.D will be fully aux fait with the situation and will be discreet.
A wig/hairbrush if you have a wig or hairstyle that needs brushing from time to time. If you have a set or coiffed hairstyle you won't need one. I used to need one. Now I don't.
As mentioned above, if rain is a possibility then a small umbrella that fits in a handbag is a useful thing to carry. You don't want to get your wig wet.
There may be a few other items you choose to carry, so factor these in when you consider the size of your bag.
OK, you know the time and the place, how to get there and what to wear and take with you on the night. Let's fast forward to the big night.
The Final Countdown
So the day is here and it's time to get yourself ready to sparkle. The more time you have to get ready, the better. It's a good idea to have a check list of your preparation, so you don't forget anything. Try to take your time if you can.
First pack your handbag for the night, so all you have to do is pop your mobile phone, lipstick and keys in, when it's time to head off
Be thorough but careful with your shaving. You don't want to cut yourself, which can waste time while you control the bleeding or even ruin your night by meaning you can't wear makeup.
Apply your make up slowly and carefully. Don't try anything new or different. Just keep to your usual look. This is not the time to experiment.
Take your time dressing. Make sure you check little details like straight bra straps. Stick to the outfit and accessories you had planned to wear. Don't go changing anything at the last minute.
Once made up and dressed, it's time for your crowning glory. Your hair or wig, if you wear one. Take time to style your hair correctly or make sure your wig is fitted correctly and styled how you like it.
Add any accessories and jewellery you are planning to wear.
Now put on your shoes and take a look in the mirror. It's best if you have a full length mirror, but don't worry if you haven't. Just make sure that everything looks good. If it does you're ready to go.
If you need to wear different shoes to drive in, change into them now. But don't forget to take the shoes you intend to wear for the night. Also don't forget to take your coat if the weather forecast says you might or will need it.
And off you go on your big night out.
The Big Night
You are going to be very excited and nervous but try not to let nerves get the better of you. If you're driving, concentrate on the job in hand and drive safely. Hopefully your research will have identified where to park and the quickest route to the venue
When you get to the venue, look for the people who seem to be the organisers they will usually be near the entrance during the prime arrival time.
Make yourself known to them, and let them guide you and give you the information you need to have a good night. They may introduce you to others, which is a good start. If they don't and leave you to find your own way, then don't worry. Make eye contact, smile and say hi to a few people. If there is a bar, or refreshments area, that is a good place to station yourself near. I can almost guarantee that someone will respond by saying, "Hello, I haven't seen you here before". And you will be able to go from there. The trans community are very welcoming and friendly and look out for newcomers, so I guarantee you will be welcomed
I mentioned the bar just now. If you're driving home, obviously don't drink. But if you're not, and you are going to drink alcohol, then don't drink too much. You don't want to get drunk. You want to have your wits about you, so you can enjoy your first night out and remember every minute of it. As a cautionary tale, a friend of mine went to a well known club on her first night out, and drank so much she tripped headlong down a flight of stairs from the upstairs bar. Not good.
Apart from that, just enjoy the night and the wonderful experiences and emotions. If you feel a little emotional or overwhelmed at any point, just find a quiet corner and let it wash over you.
Don't forget to get some photos of yourself taken so that you can look back and realise this was not a dream.
You did this!
I hope someone finds this advice helpful and if you did I hope you had a wonderful first night out.
Deeanna
💋💋💋
