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.
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.
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.