SINGLE CROSSDRESSER ISSUES
Crossdressers not yet in a committed relationship or married have a special set of challenges. While many desperately want to meet a woman, they despair of meeting one who'll be sympathetic and understanding of their situation. Given this, these are some of the more important issues single crossdressers should consider:
1.) WHEN do you tell a woman you're a crossdresser?
All reasonable people agree "Before you get serious, definitely before marriage". Any crossdresser who would withhold this information is setting the stage for disaster.
Now, many crossdressers fear rejection and losing their woman if they do this. To this I respond: if you tell her the right way (more on this later) and back it up with actions, the edge can be blunted. Also, it's better to know right away if she can't accept it. Think about which is worse: losing a woman now & dealing with a few months of heartbreak & finding someone else, or being trapped in a marriage where you have to be closeted all the time.
Also, not telling her creates serious long-term damage when she feels betrayed by your not having told her. Once you get intimate, a boundary has been crossed, and anything after that will be seen as betrayal. Women fear betrayal perhaps more than men do. And this can poison a relationship for years afterwards: she'll definitely think "What else has he been witholding?"
Some take the opposite tack of "Tell her immediately". The logic is "If she can handle it, fine. If not, it was never meant to be". But when a woman is just starting to know you, crossdressing will become one negative thing to examine against an otherwise blank canvas. But if she knows other things about you, your personality, your history, your likes and dislikes, she can get a more balanced picture. She can weigh this against the positive things she already knows about you.
Now, there are some women who simply will not accept this. If you meet firm and unyielding resistence, you may have to consider cutting your losses and ending the relationship. It's better to lose $100 today than $1000 tomorrow. And you know the cliche "There's many fish in the sea"? It's true.
2.) HOW do you tell a woman you're a crossdresser?
Dropping hints to test the water is useful. You can make references to current movies, or say you knew someone who was transsexual. You'd be surprised at how this can be creatively juxtaposed into a conversation. Her reaction gives you an idea of where she stands. Be advised that women with strongly religious backgrounds are often the least tolerant of diversity. Also, a woman with some college education may also mean a more open mind.
Where you tell her is just as important as how. Obviously, choose a private indoor place, not a busy public one. Or, a tranquil open-air park or beach without too many people is nice. When you break the news, be positive. Don't preface it with a negative vocabulary of shame like "We've got a problem to talk about". She'll immediately tense up and brace for the worst.
It's better to be more casual, indicating that you've got something meaningful to talk about. Negative words send out signals of shame. Positive words mean unique and special. Also, use disarming body language helps: maintaining eye contact, holding your hand to your chest, using sincere tone of voice, etc
Don't give her too much information at first! This is a lot to handle in one sitting. If you start throwing out biological and sociological theories, or your transgender life story, it's going to confuse her. Keep your words simple and to the point, and don't use our communities' slang and acronyms. Reiterate that you respect her enough to feel you have to be honest with her, and that you're not gay and not transsexual.
3.) Be prepared to make compromises.
Single crossdressers have, up to a point, the freedom to indulge. But once in a relationship, this changes. There are suddenly limitations on the frequency and extent one can self-gratify.
But don't consider it as having freedom taken away. Consider it as now thinking in terms of two people, not just one. Two is more complicated number than one, but not a worse one.
Also, what might seem insignificant to you, may be significant to her. Take body shaving, for example. Most TV's cannot understand how anyone would have a problem with it. But to many women this can indeed be a serious issue. They like hair, they want a man. What might seem right and fair and logical to men may seem wrong and unfair and illogical to women.
Relationships always call for compromise on issues: finances, religion, tastes in food, attitude towards raising children, likes and dislikes in entertainment, feelings towards relatives, division of chores, etc. Maybe sexual issues are a little stronger, but they're still just another issue up for negotiation. The secret is: R-E-C-I-P-R-O-C-I-T-Y.
4.) Issues of Security.
Having a woman over to your place presents challenges. If you live by yourself, you're used to having a wardrobe and femme things around. But you can be betrayed by a single makeup sponge, a forgotten pair of panties, or a stray copy of a newsletter. Start thinking NOW of places to hide things if need be. These can be in zippered rollbags covered up by men's clothes, the trunk of your car, or even a friend's place if just for a day or two.
And keep pictures of yourself en femme under lock and key. Time and time again I've heard of dozens of TV's who've been outed when they left compromising photos lying around the house. Make the last-minute "Transgender Sweep"- a quick glance of the room for any stray femme items.
Also, be prepared for excuses for being absent when you go to support group meetings or events. You may even have to skip a meeting sometimes. Don't give the impression:"I have to be at this place, but I can't tell you where". When you put an air of mystery around something, it encourages her to imagine the worst.
5.) Communication Problems.
If you start off with the assumption "I can't change, this is something you need to accept" there's a problem. The point of a relationship is to grow together, not to take a stand, and have the other person yield to it. True, you may not be able to stop crossdressing. But you do have control of when and for what interval you do it, and to what degree she has to see it.
From having talked with several genetic women, I've learned that many women fear that crossdressing may be a THRESHOLD. Just as marijuana was feared to be a threshold to heroin and cocaine, crossdressing may be feared to be threshold to becoming gay or transsexual. You need to reassure her on both counts that you aren't. And you can't do this with just words, the suspician may linger on. You have to do it with deeds: by being willing to be the masculine man she wants and needs.
Lies are bad for relationships. If you tell one lie, you have to tell ten more to cover it up. You'll also have to keep lies straight as contradictions get noticed. For example, if you say it's your bowling night: be prepared for questions on where the alley is, how your game went, who you were with, etc. That's a lot of things to have to keep track of, isn't it?
Crossdressers pride themselves on how they understand women better by having walked in their shoes. Now's the time to put it to the test by really understanding a woman's point of view in the relationship and what she wants.
6.) Start developing new interests.
One of the first things a person wants to know is "What are your interests?". Obviously, you can't hit her with the truth yet! Evasive answers arouse suspicion: are you involved in something illegal? Before you start looking to meet someone, you should have one or two interests to be able to talk about. Yes, it may mean taking time away from dressing around the house, shopping, or support group meetings. But it will make you a more well-rounded person, and better able to have a relationship.
7.) Use your advantages.
Single crossdressers have several advantages over married ones. No, it's not the obvious freedom to dress. It's that those single and in the community have already gone through the difficult process of coming out to themselves BEFORE getting married. By the time they meet someone, a lot of the traumatic initial self-confrontation is past. By contrast, having to do this while married or in a relationship is a lot harder.
Single crossdressers also have the benefit of learning from married ones. By asking the right questions, listening and learning, a single crossdresser can avoid miscalculations and errors many married crossdressers unknowingly make. And if a married crossdresser can share this knowledge with a single sister, they'll have done what our groups are supposed to be doing: providing support.
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