How do I tell a girl that I crossdress?

Keep doing the crossdressing since you like it.

Your problem sounds more a matter of timing and reason to tell the girl about it.

Not keeping a secret is a good attitude regarding meaningful parts of your life.  Usually our relationship partner is someone whom we trust as a safe person to know all about us.

Once you feel at ease with your potential partner then bring up your crossdressing.  Based on their handling of this intimate part of your life, you will know more as to whether or not you feel more or less drawn to them.

Secrets held within a relationship usually get worse with time.   The person who feels unsafe in truly being and stating themselves eventually will end up feeling ashamed of parts of them which prior to the relationship, felt good or at least not worrisome.

While this might not be the first thing you want to discuss when you meet someone, it is important for you to be yourself.  It's better to weed out 10 people who can't accept you to find that one who can.  

Thanks for asking this question. I think the most important part of what you mentioned was that you do it because it makes you happy. For that reason, I would encourage you to keep doing what makes you happy.

As far as telling girls or keeping it a secret, I don't really think that it's necessarily one or the other, at least not the first time that you meet. In other words, one part of your decision-making could be whether it is something that you always want to address in the first date, or perhaps something that you address after you've known each other for a couple of meetings. The answer to that question may also change depending on who you are dating. I would imagine that each person that you are with mainly due to a different decision this was when to disclose this. 

It sounds like this is an important part of you, so I would think that if you were going to date someone long-term, you would want them to know about the most important parts of you, including that.

I also encourage you to remember that if you meet someone who is not comfortable with this, that does not mean that there is anything wrong with what you are doing, but rather something that the other person is in some way deciding not to continue learning about or choosing to have someone they are dating like to cross-dress.

I'd also ask you to consider this: Are the people who you say this to expecting it? My guess is that the answer is probably not. Along with that, Are they going to have questions? I would imagine so.

Are you comfortable answering questions?

I wonder if you could figure out yourself or with friends (or perhaps even with a therapist) how you would answer these sorts of questions:

• What exactly is cross-dressing?
• Does that change the gender that you're attracted to?
• What does it mean to you?
• Why is it important to you?
• And what you want your listening person to know about you related to cross-dressing.

There could even be ways that you can start the conversation by asking them to be open to listen to you and ask questions about what they are thinking before they make any quick decisions about you or the relationship.

I certainly hope that you find the right person for you. I imagine that having this conversation could be stressful, especially considering the idea that you have had some negative reactions in the past. Remember that talking this through with a therapist could be very helpful.

It can be difficult to explore a personal desire, such as cross-dressing, when your partner does not share the same interest. It is important to communicate openly with your partner about this issue and try to discover what makes them uncomfortable with the idea. There are likely many factors at play, ranging from insecurity about their identity, fear of judgment from others, or simply not understanding what this means for you. Listen to their concerns without judgment and try to express why it’s important for you to explore this side of yourself. As much as possible, keep the conversation open and honest.

Another option could be to find activities both parties can enjoy related to cross-dressing. Perhaps there are clothing stores or events nearby that focus on gender nonconformity where you could explore together without feeling pressure. You could also talk with other people with similar interests and get advice on handling an unsupportive partner. Depending on the situation, if your partner is still uncomfortable with you exploring this side of yourself privately, then perhaps it would be best for both parties if you refrained from doing so in front of them, regardless of how hard it might seem not to.

Ultimately, it’s up to both parties to decide the best solution for everyone involved. If communication fails, then seeking professional counseling might be a great way for both parties to work through any potential conflict or confusion that may arise from conflicting desires such as these.

Normalizing cross-dressing and being open about who you are.  Consider if this could be a deal-breaker , which would encompass considering if you want to be with someone who does not accept you for all you are? Also explain your personal reasons and the possible reasons many others crossdress, how it is not always for sexual stimulation. 

If you enjoy crossdressing and it is an integral part of who you are, giving it up for anyone else or to get into a relationship will only lead to resentment and resentment in a relationship usually leads to it's demise. So I would caution you against giving it up for someone else, as you won't be happy and neither will your partner because they will be losing out on getting to know your authentic self. 

Stay true to your authentic self and balance that out with dating people who do the same and are open to exploring thoughts and feelings in a relationship. You definitely get to choose the right time to share this with a partner and I encourage you, if it feels safe, to talk about it as soon as you can. Sometimes just keeping something a secret for a long time in a relationship can also lead to other issues, too. Also, if you know the other person doesn't respect this part of you if you find out early you won't waste your time and can move onto a relationship that feels more supportive.

I hope this makes sense and I wish you the best of luck!

It would be my professional opinion that the desire for you to keep it a secret at all, while yes I could see it as "giving you a chance with a girl," is something that might be more about a discomfort for you. If you are comfortable with your kinks and fetishes (if I may call it such, not my intention to pathologize in any way though), then be as open as you want to be. But I also don't know that you need to be announcing it as part of your online dating profile (because you do say it "bothers girls I ask out" which to me implies that that is what you're leading with.) My hope is that people don't make dating decisions based on your kinky behaviors, but more likely that they would make decisions based on your own comfort and security with said kinky behaviors.

Your happiness and healthiness is key.  I would not suggest that you hold back and keep it a secret.  You should be up-front about it, but perhaps gently bring it up on a date.  When thinking about whether or not you should stop, think about how it makes you feel.  Perhaps try to be social at more accepting affirming locations in your area.  The people who will accept you for who you are are out there.  You may not be looking in all of the places you have available to you.