An internet search of dating & crossdressers can lead to some dubious sites displaying lewd and inappropriate pictures of crossdressing men. Unfortunately, this reflects poorly on our entire community and does nothing to help our social status.
We are portrayed as ‘sex freaks’, willing to get with anyone who will have us. In reality, most of us (whether gay or straight) want to be in a relationship with someone who will care for us and love us unconditionally. These dating sites seem to be aimed at lurkers and admirers rather than anyone who is actually seeking something meaningful.
In response to this, my wife and I decided to collaborate on a post that we hope will aid those who are confused on dealing with a crossdressing boyfriend.
Initial Shock
Okay, so you’ve discovered that your man is a crossdresser; either he told you or you found out somehow. You’re probably wondering what to do and say next, and we’re here to help.
Once you’ve gotten past the acceptance phase and stopped wondering why men crossdress, you’ll surely want to know more in order to get the most out of your relationship. Unless you’re completely against his crossdressing and refuse to budge, you should want to do things that will make him happy.
There are tons of books, magazines, and shows dedicated to helping women get to know their men better. Problem is, they almost never consider the possibility of a feminine / transgendered man.
What To Expect
At one point or another, both of you will experience feelings of inadequacy, likely stemming from the gender roles that society has worked so incredibly hard to impress upon us. For instance, most girls grow up expecting nothing but masculinity from their boyfriend and any feminine expression from boys is castigated and frowned upon.
Just because your man crossdresses doesn’t mean that he can’t provide you with what you want and need in a relationship. You are in a unique position to not only help him in feeling comfortable and confident in his feminity; moreover, you can benefit from his heightened sensitivity, kindness and thoughtfulness.
It’s not always easy, but with hard work, sacrifice and compromise you can assure that you spend many happy days together.
Date Ideas
Going to an art museum is an excellent date to arrange with a cross-dresser, you can both take in the sights and appreciate the creativity and expression that is quite similar to female impersonation. Nature parks, picnics and hiking are other possibilities that will take advantage of the beauty in this world.
Tradionally, you are probably used to going shopping with friends, but consider taking your transvestite boyfriend on your next excursion to the mall. You could either both shop for clothes or you could simply assist him in picking up clothing, jewelry and shoes. Going together will likely make him feel more at ease, enabling him to enjoy the experience more fully. Nervousness may be an issue, but that is completely normal. There are few things that a crossdresser likes more than shopping.
Gifts To Consider
Typically, women are the recipients of flowers, candy, lingerie and jewelry and there is certainly nothing wrong with that. We are definitely not advocating for this to stop (cross dressers take note 
). However, if you are dating a crossdresser, why not consider buying him something like this for Valentine’s Day, a birthday, or any other occasion.
Your boyfriend would greatly appreciate the sentiment and the gesture will do wonders for strengthening your bond. If you are either uncomfortable with shopping for him or are not sure of his personal style, a gift card would work just as well.
Discussions To Have
This is a doozy, because we are never educated formally about transgender issues. That leaves men and women in a tough spot, as there are many things to talk about. Dating inherently requires long conversations that enable the two partners to get to know each other, but imagine how that list grows as crossdressing is thrown into the mix.
How Important Is Crossdressing to You?
It may not be obvious at first, but crossdressing can mean different things to different men. It can range from occasional thrill to full blown emotional involvement. Whatever it is, it behooves both of you to find out. Keep in mind that your boyfriend may be reluctant to fully disclose the relevance of crossdressing in his life for fear of scaring you off.
Do You Intend On Transitioning?
Again, this is a tough one. Tough because he may know but doesn’t want to lose you but also difficult because he may not fully understand his gender identity. If you can discuss this, though, and get to a conclusion, both of you will know where you stand and can make an informed decision on how serious the relationship can be.
How Involved Should I Be?
Some men want to have you by their side not only accepting them, but also aiding them in their feminine expression. Remember, most men grow up unable to develop their feminity and even when expression is tolerated, it is quite rare when a man has grown up developing a girl’s fashion sense and makeup skills.
However, perhaps your boyfriend just wants acceptance, and he’ll do the rest. You’ll never know until you discuss it, so get to it !
Would You Like Your Friends / Family To Know?
Beyond the scope of your relationship, your boyfriend may have specific intentions on who should know about his crossdressing. In some cases, he may want only his closest of friends and family to know. However, this may be a secret and should be kept as such if that is what he wants.
That is not to say that you shouldn’t have another outlet in which to discuss these matters. Your boyfriend should respect that once you are told, you are dragged into the closet with him. It is not fair that you cannot seek assistance outside of the two of you.
Note From a Woman’s Perspective
(This entire post has been a collaboration of ideas between the two of us, but the following section was solely written by Rebecca)
Dating a Crossdresser can be hard, fun, amazing, spontanteous and complicated all at the same time. After you have gotten over the initial shock and or questions (maybe you have always known what crossdressing is or wanted to date one) you will soon realize that there is not a tell-tale sign. On a regular day you may not notice that your partner is a crossdresser besides the fact that he wears clothing and accessories of the other gender. You probably would never know otherwise. Sometimes they are masculine, feminine and at other times a little bit of both.
If you are very open with your partner, you will probably play many roles in his/her life. You are their friend, fashion consultant, a makeup artist, lover and confidant.
Off You Go 
!
You can either focus your energy on lamenting the fact that the man you are dating is a crossdresser or you can do your best to accept him for the person that he is. If you can get past this and enjoy that aspect of him, you will likely both be happier and have an enjoyable time together.
Remember, crossdressers are 42% more likely to buy you fine jewelry, 64% more apt to watch chick flicks with you, 71% more likely to go shopping with you without making a fuss and 88% less likely to cheat on you. Okay, so I just completely made up those statistics. Although the stats are false, the sentiment is that a crossdresser can really surprise you in what he brings to the table. He may not be what you expected but when all is said and done your life can definitely be enriched with him in it.
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When a cross-dresser says “You look really nice today” – you should know that he really means it. Chances are he knows how long it takes to get ready and some of the decisions you’ve made in turning out as well as you have.
Sure, everyone’s tastes are different, but a CD partner will think twice when picking you a birthday present… especially something like jewellry, clothes, make-up or luxury bathing.
That is so true, with a crossdresser women have someone who understands that feminine appearance doesn’t just “happen”, there is so much time and effort to put in.
Interesting what you have written today. I have been searching for a more local support group and I found EXACTLY what you mentioned- sex and porn. That is not what I am about. I was seriously disappointed with my efforts.
The balance for your article is well written and does put the issues and dilemmas into words very well. It is too bad I cannot use them with my wife to help stem her fears…. we have been dealing with it for 30 years.
Oh well. Maybe I can be a little more supportive for her shopping if I don’t go broke in the process.
Ellen
Thanks Ellen,
This is the type of article I wish existed back in 2000 when I was trying to explain crossdressing to my girlfriend at the time. I scoured the internet but was only able to find articles talking about what crossdressing was but nothing about helping a girlfriend and giving good advice.
I hope that this article will be able to help those looking for a little guidance
.
Hi Jessica
An interesting read and nice to have the input also from Rebecca. I guess the first decision is whether to tell/ when to tell, but that is only the start and as you indicate it is oh so complex, especially as the tgirl herself rarely knows exactly whats she wants/ how far to go, especially in the period shortly after telling that first person.
That was certainly my position. I told my wife 7 years ago and never told anyone else (my wife did tell one friend) and what we both can accept and want to get out of it is constantly evolving.
I do agree with you though, that there are lots of advantages in having a cd’ing partner. Aside from the ones you have mentioned…….
We have made lots of new friends, we go away more often, dance/visit clubs years after we had given them up, have an extra Xmas, swopping pressies very late on Xmas eve. My wife gets twice as many presents (and has to give twice as many) for birthdays/ other anniversaries and they are generally much more likely to be something she likes. She also gets (more) help around the house and especially gets clothes put away etc etc
Yes, she does say she would rather I wasn’t a tranny (uk), but does accept that it has put a spark (back) into our life.
Hugs
TinaCortina x
ps I think Rebecca’s stats are definitely understated!!
Hello Tina,
Thanks for the kind words, we really appreciate them. Wow, sounds like you and your wife have such a great time together, I can’t tell you enough how great that is to read.
Of course, most women, when being 100% honest, will say that while they enjoy the feminine side they would prefer it wasn’t so strong.
I have run in to this issue of trying to find a date online (an act I have only recently started.) I am on OK Cupid and I have removed the fact that I am a cross dresser from my profile to see if I get more email from the woman on the site. I also searched on the net for a CD dating site and only found one but it looked to cater more to the Drag Queen section of our community. Not what I am into.
Hi Gaven,
Best of luck with the dating sites, you’ll have to keep me updated on how things are going. I am disappointed with the lack of dating sites catering to transgendered people who want a real relationship. Every time I see crossdressing being mentioned on dating sites, I am appalled by some of the comments I read.