8 Tips For Dating A Crossdresser And Things You Should Avoid

crossdresser dating tips

We have all heard of crossdressers – Today, we are speaking mainly of men who like to dress up as women. This does not mean they are transgender women or gay men. In the past, the idea of a cross-dresser in a man was highly odd; something was wrong with the man; he would have had a bad reputation. If a woman married a man and discovered him one day wearing her stockings or her underwear, she would promptly divorce him on the spot.

Crossdressing still holds a sinister twist to it

Instead of a man living up to a reputation as a person of strength and ruggedness, this kind of man is a weakling to many; something is not right. Deep down, the cross-dresser [1] has a desire and a yearning for womanly things. He wants to inhabit their lifestyle and experiences. He loves the thought of crossing his legs in sexy black tights, feeling the soft materials of a bra around his chest. Sometimes maybe the expectations of being a man just get too much for him and he longs to secretly escape into the world of a woman where he can escape the demands and expectations of what he should be as a man.

Of course, it can be disturbing to sense that someone who you believed was firmly anchored to the gender they were born into has become something much more complicated than that of just being a man. Events and circumstances in his past have subtly led him down another path ….

When some men get immersed in their feminine side, their neurotransmitters produce sensations of excitement and pleasure

Cross-dressing excites them and makes them feel comforted and complete. But when the neurotransmitters are denied, he can feel denied, depressed, and lack concentration and even his sex drive can be reduced. Cross-dressers will often say they need to cross-dress.

8 Tips of Dating a cross-dresser

1. Lots of people ask, “Does a cross-dresser date a guy when he is dressed up in a woman’s clothing?” Many cross-dressers are married men. Their wives might know about their fetish but she also needs to understand that he will not stop with his cross-dressing. If he does date a girlfriend, he might let her know that he is a cross-dresser but whether he decides to come out in public to his family and friends is not really likely.

2. Often when dating, a girlfriend will become intimate with her cross- dresser boyfriend. She might suddenly see him one day looking at her clothes and trying them on, or she might catch him one day pretending to be ‘funny’ with her lipstick. She might notice later that these little incidences keep on occurring where she cannot pretend any longer that she didn’t notice. She might at that stage ask him outright if he is a cross-dresser.

3. If you are suspicious find out before you get married: Because sometimes you might hear the words "There is something I need to tell you – something I have never told anyone before." It might just mean the end of your marriage when you hear your husband say that he only gets turned on if he is dressed in women’s clothing, and that all along he has been dissatisfied! You might have believed there would be no way it would end your relationship.

4. Even though a lot of cross-dressers are heterosexual men, some of them are gay [2].

5. Hearing him say he is a cross-dresser will require adjustment from you. For instance, you might want to dress up in sexy outfits but he might never even request you to because it makes him feel sexy when he is the one dressed up. It’s not uncommon for crossdressers to want to feel sexy. There is nothing wrong with that. But it will depend on who he wants to be sexy for. So if you feel that your boyfriend is posting pics of him more than he is letting on to you, you might need to let him know how you feel and why. And if you’re concerned that he is only interested in dressing sexy for himself rather than seeing you dressed up sexy, you will need to talk to him about it.

6. Truthful communication will be imperative: Good communication is vital to the success of any relationship, period. Now that you have discovered that your boyfriend is a cross-dresser, you will need to let each other know what is needed and expected of each other. It will need to be communicated openly and honestly.

7. His sexual preference: Maybe you might have to realize that your boyfriend is not a heterosexual guy. He might be bisexual, and certainly, he might be bi-curious! Read about cross-dressers here and what they have to say!

8. Monogamous relationship: If your dating requirements as a woman are to be in a monogamous relationship, you will need to communicate this with your boyfriend. You will both need to be in agreement on this level and committed to keeping it a monogamous relationship. Thing is, a lot of cross-dressers have sexual fantasies that cannot be fulfilled by their partner. They want to experiment with others and have their fantasies fulfilled by more than one partner. This you need to understand, or else it can make you very unhappy. Trust is a huge and important part of any relationship [3].


Every relationship has rules; often unspoken rules, but they are there, and when they are not adhered to, they can cause havoc in a relationship. One example of the unspoken rule is a monogamous relationship. It’s a relationship between two committed people with no others involved in it sexually. When you are in a relationship with a cross-dresser, or have discovered your boyfriend is a cross-dresser, you have to clearly decide what you are going to do about it. Because a cross-dresser, as you will have realized, has some sexual fantasies that might not include only you. Rather than just continuing in your uncertainty and hoping it will all work out for the best, our tips and advice above should help you make decisions that only you can make about your future. His behavior might well fall outside your comfort zone. Talking about it can help you perhaps reach an understanding and help you know what to do.


[1] https://www.theschooloflife.com/article/the-psychology-of-cross-dressing/
[2] https://pubmed.ncbi.nlm.nih.gov/9415796/
[3] https://www.goodtherapy.org/blog/when-cross-dressing-puts-relationships-in-the-crosshairs-0930144