I'd like to hear from crossdressers who date men.

[@tammileetilliso]

What are the biggest challenges you encounter when dating straight men? Is there a lot of awkwardness, prejudice, or lack of understanding?
What about sex? Do you feel comfortable exploring your sexuality freely, or do you feel pressured to "perform" in some way?
Translated from Portuguese by Google.

[JenninSC]

I've had a few dates but to be clear, none of them are straight. They know what they are getting into, I don't want them to have any surprises. That being said, with the ones that are open to it, I can be free. I prefer the female role when dressed so the guys I've been with have not had to pressure me into anything.

[CharlotteCD]

No crossdresser dates straight men. Get that fallacy out of your head first.

[Genifer Teal]

Charlotte you bring up an interesting point. It's really all in the label. I get what you're saying. Crossdressers can date men, but I guess at that point they need to change their label.

With that said, dating men is an interesting conundrum. There's so many different men to date and different reasons for dating them. There's the kind that might secretly be gay and are afraid to admit it, so they're happy to get the d without having it in a male package. They want the male package, but not the whole male package, haha.
So I decided to look something up to help me write this, and it came across a very interesting point that kind of negates, everything I was going to say.

Not exactly the same but similar - I'm a fat guy and my husband is a "chaser." I was worried about that sort of thing too, being objectified and thought of a sex object rather than a human. Don't make the mistake in thinking it doesn't happen, because it does, however there are a lot of guys out there that are normal and still have a specific taste and interest. My best advice is do as you are asking and don't judge a book by it's cover. If they like you, for whatever reason, as long as they treat you well and respect you it shouldn't matter why.

I can add that. I dated a guy who is totally okay. With me being a crosstre, he loved that about me and it went well other than he did have a wife somewhere and there was that issue always lingering, but otherwise everything was fine until he had some major heart issue or whatever some surgery he might have died from and ghosted me. Just in case he died, he didn't want to have loose ends. After that, I lost respect for him, but he was a regular guy. A decent guy other than the probably cheating aspect.

Then there was another guy who was also kinda normal. He just liked crush. Dressers couldn't really explain it, but he really liked us. We went on a real date, at least. It felt like the real day. It was a real date, but regardless he felt I got too much extra attention for being who I am. And he didn't know how to handle that. His words were maybe I could tone it down a bit. It's not like I was gonna wear a ballroom gown to go to the supermarket. I wore pants and a top for the date. And he felt that was a bit over the top LOLI don't know how much more carefully I could have dressed. Anyway, he didn't like the attention. I got probably mostly because how tall I am. I can't blend in no matter what. So I make the most of it anyway. That's my other experience with dating. So what I started saying is yeah, you get the fetish guys that want nothing more than The Fed side of it.
And you get the gay guys that think they're hiding it. The gay part, not a lot of normal guys, because they have to deal with the stigma society, would put on them for a dating, not a real woman. It's a tough game out there for us. I'm not looking, but if the right thing comes along so be it, I probably won't resist.

[CharlotteCD]

It's very simple for me, hence my previous post.

If it's a crossdresser, when the clothes come off it's just two men having gay sex.

I posted exactly that in a recent thread about dating men.

Just own your sexuality. It's 2025.

[TheHiddenMe]

No crossdresser dates straight men. Get that fallacy out of your head first.

Nope.

If a crossdresser dates a woman, when the clothes come off he's a man and still a crossdresser.

If a crossdresser dates a man, when the clothes come off he's a man and still a crossdresser.

Crossdressing and sexual orientation are two entirely different things.

[docrobbysherry]

"Parts is parts!" And, for straight men, when the dress comes off we have the WRONG PARTS!:devil:

[CharlotteCD]

Nope.

If a crossdresser dates a woman, when the clothes come off he's a man and still a crossdresser.

If a crossdresser dates a man, when the clothes come off he's a man and still a crossdresser.

Crossdressing and sexual orientation are two entirely different things.

You're focusing on the wrong thing. What I'm saying is that a crossdresser dates a bisexual or gay man.

No straight man has sex with another man just because they or the other person is wearing lingerie.

They're BOTH gay or bi. It's that simple.

[Genifer Teal]

I see it differently. Labels are labels, call it whatever you need to. intimacy is the same regardless who it's with. Whatever parts you have we'll make it work. I may not want to feel a beard when i'm kissing someone, but that's not just if they're presenting as a woman. I don't wanna feel a scratchy beard. It's mostly what's going on in your mind. It's important to like who you're with. Beyond that it's just sharing pleasure. There's lots of ways to do that.

[TheHiddenMe]

You're focusing on the wrong thing. What I'm saying is that a crossdresser dates a bisexual or gay man.

No straight man has sex with another man just because they or the other person is wearing lingerie.

They're BOTH gay or bi. It's that simple.

No, I am completely focused on the right thing.

First of all, crossdressing is not a term that exclusively applies to men. Women are crossdressers too. So a woman who dresses as a man and dates a man is STILL a crossdresser and when dating a man and having sex with a man is a heterosexual. A woman dressing as a man and having sex with a woman is a homosexual.

Dressing and sexual attraction are 100% not the same. You are making up a definition that does not exist. Crossdressing is about wearing the clothes of the opposite gender and has nothing to do with sex.

[Crissy 107]

Mod hat on

Let’s knock off the back and forth here or this thread will be closed

[Jessica Secret]

My boyfriend is bi but he loves the mix of my day to day male personality and female persona/looks in the bedroom. We were really good friends before becoming boyfriends and we connected on so many levels. No awkwardness or lack of understanding at all. And in the bedroom we have an incredible sex life - I have an extensive lingerie wardrobe and every time we make love it's beautiful, romantic and sensual, as if it's a wedding night/honeymoon. I definitely get to explore my sexuality freely with no restrictions. It's an amazing relationship.

[CharlotteCD]

Mod hat on

Let’s knock off the back and forth here or this thread will be closed

Feel free. Me stating that it's gay or bisexual for two males to have sex is correct. Putting clothes on is irrelevant.

I don't know why women are being brought up here.

It's frankly a stupid disagreement from somebody who clearly doesn't understand basics of biology.

[DAVIDA]

Well, now you get your wish.
Thread done.