I?m often asked about dressing services and mistresses who will help a crossdresser to dress and experience some of their fantasies. While there?s no doubt that some of these services are really great, there?s also a bit of a problem with some. They?re expensive, and often a person can feel that they?ll only achieve the look their looking for if they consistently dress with that particular person.
There?s also that rather annoying practical issue around trust. If someone is doing anything purely for the fees their earning, you have to ask yourself if this is really something you wish to subscribe to. After all, this is something of an intimate relationship, and could come badly unstuck. My personal opinion is that it?s far more rewarding to find a person who genuinely loves to dress you, and is excited to do so.
If you can develop the right friendship or personal connection, it?s going to be far more rewarding for you and in many cases your friend will get something out of this, too. It?s not all about you.
Many women get very excited about dressing a man. It is, after all, the sincerest form of flattery. In my experience people enjoy being asked for their advice on almost any subject. If you can get past the awkwardness, many women are more than happy to help you with dressing when approached in the right manner. And that?s exactly what we?re looking at today.
One recent comment from a Jenny, who enjoys dressing a man was, ?I love to see a man make this effort. It?s good to see someone try to understand a woman in this way. I like to see him connect not merely at an aesthetic level, but also at a psychological level. I want him to look good, but also start to think like a woman. Only then can they really begin to know who I am, and what my journey has been. When I see that in a crossdresser it?s irresistibly hot. I get completely carried away!?
Jenny went on to tell me that when she recently put lipstick on a man who had dressed for her, she found her hands trembling so much she could barely apply it, she was so excited. ?I feel so turned on by it, and so empowered. I love to see it, and I love to feel the sense of appreciation. Of course I?m going to be turned on by it!?
Ideally we should be quite capable of dressing ourselves. After all, our children are! However, the most joyful thing a crossdresser can do is find a friend with which to dress comfortably and with trust. If you read An English Country Garden you?ll see a lot about the idea of trust and a thorough exploration of it. Trust is a huge factor and one that many crossdressers find hard to deal with. A paid dressing service or Mistress sometimes circumvents this, but can also go very badly wrong. It?s generally quite a sterile experience. In the long run it?s best to develop the skill of being able to engage with others who are interested in crossdressing with you.
This can often be a woman who is excited by the idea, and some people find men that are also turned on by the idea. My Little Black Book is a great way to do this, because all members commit to a set of guidelines that keep it safe. In the end though, you own skill at being able to engage others in your dressing is a going to be what really helps you.
So, let?s look at a simple step by step guide to drawing someone into your dressing. Keep in mind, we?re looking for willing partners, and trying to help them overcome their nervousness as much as anything. We?re going to do a lot better with a gentle and sensitive approach than by telling them that we look better in a corset than they do!
The first thing to remember is that language is important. You don?t want to go out and directly ask ?Hey, can we crossdress together? to a complete stranger. In fact, even with someone you know well, that?s probably the approach least likely to yield a positive result. Initially you want to be sure you?re comfortable with the person you?re going to approach. If you?re not comfortable at a basic level, you sure won?t be as intimacy and trust is brought into the equation!
Next, let?s think about vocabulary. As you share a little more about yourself, you want to be using terms like ?I?m enjoying finding the gentler sides of myself?, and ?I quite like the idea of exploring some of the less aggressive aspects of my personality?. This is almost a coded message telling her your interested in crossdressing. Eventually you can throw in phrases like, ?I?m beginning to find a slightly less masculine form of myself?, and ?I?m finding there?s a little more feminine version of myself?.
If you toss out these phrases at carefully chosen moments you?ll see how well received they are and you?ll be able to gauge if the person is on the same page as you. I would caution you that, even if they appear very receptive, don?t rush things. By taking your time you?ll feel more comfortable yourself, and you?ll build your trust as well as theirs.
The next step is to begin to draw the person into behaviour, rather than merely conversation. Again, you?ll
want to be reading their excitement or resistance to this. Be receptive to the idea that they may change their mind, and you?ll need to respond to that positively. We always look for ongoing consent in our relationships. Knowing if it?s going off the rails, and gently pulling back, is something you should not be afraid of. There will be other opportunities.
Here are some sample activities, and I would suggest offering them in this order as they are at varying levels of intimacy. If you step through the series of exercises you?ll be progressing in a fun way without too much pressure.
- Ask them to help you with your eyebrows.
This is a simple low risk introduction that most people find entirely unthreatening, and an easy step to take. If they?re really not interested you?re not going to feel too awkward. After all what have you really risked?
2. Ask if they?d go for a pedicure with you.
The pedicure is a great next step (pardon the pun), and a way for you to offer your dressing partner something so that they become invested in the process. If they?re getting a pedicure out of it they?re likely feeling good about it.
3. Ask them to measure you as you?d like to buy some ?other? clothes.
By now you can talk to them about bra sizes and other intimate questions. It?s quite normal for a guy to have no clue how to measure for a bra. You may even find they want to go bra shopping with you. Getting sizing right is a common error for crossdressers, and this will really help if you?re buying your own clothes.
4. Ask them to help you with fitting and styles.
Asking for advice is always a good idea. What to wear, where to buy it.
5. Go shoe shopping together.
If you?re feeling generous you can draw the person into a deeper level of investment into the process. Many women to go shoe shopping and it feels good to give. It will likely come back to you in some exciting ways.
6. Dress together and get some pictures.
If you?ve been shopping together, it?s only natural to want to get the clothes home, and ask her to photograph you. After all, you want to know how you look. Before you know it she?s helping you into that nice little dress! ? Fiona
