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@tammileetilliso
08-01-2025, 01:46 AM
Hey everyone! I'm new here and I'm still learning the art of expressing myself in the way I feel most comfortable. One of the things that makes me super happy is exploring my feminine side through clothing, but I confess I'm still a little insecure when it comes to relationships...

I wanted to hear from you, who have more experience: what's it like for you to have romantic relationships with men? Is there a lot of pressure to "be less masculine" or "more feminine" in certain situations? Do you feel comfortable being yourself all the time, or do you feel like you need to "put on a persona"?

Translated from Portuguese by Google.

Keremy
08-01-2025, 05:12 AM
First do you want to be with a man or do you just think you have to because you are a cross dresser? If you are just being with a man because you are a cross dresser do not. You will not enjoy it as much as you want and they probably will not either.

If you desire to be with a man enjoy yourself and be yourself the right persona is always you. I do not remember who said it but it is true. Be the best you you can be.

Hugs
Keremy

char GG
08-01-2025, 12:05 PM
Be careful and upfront about who you are. You don't want any negative surprise reactions.

docrobbysherry
08-01-2025, 12:15 PM
In my experience men r not romantic, but very direct. The one's I've met want oral action!:eek:

CharlotteCD
08-02-2025, 02:54 AM
When the clothes come off you're just two blokes having gay sex.

That's something that people on both sides of the relationship may struggle with. The chaser because they're denying that they are attracted to men, and the CD because they have a dream they're a woman.

Jasmine23
08-02-2025, 04:41 AM
I've never been with a man, not attracted to them, but, when I dress up I do fantasise about attracting men, as a form of validation of my feminine appearance when dressed, it would be the ultimate compliment for men to find Jasmine attractive, but, it's something that I personally would never do IRL, but, I have seen that some CDs do go through with this. Is it gay, kinda of, but, also kinda not, as the CD is presenting as a female often calling themselves sissies and stays in that role, the men are attracted to the femininity, but, also know the sissy is much more submissive and generally easier than women

Sandi Beech
08-02-2025, 12:01 PM
CharlotteCD makes a pretty strong point. I agree.

Sandi

chrissy111
08-02-2025, 12:57 PM
The first time I ever slow danced with a man and he put his hands on my butt, I new I could never be with a man sexually.

Di
08-02-2025, 04:01 PM
When the clothes come off you're just two blokes having gay sex.

That's something that people on both sides of the relationship may struggle with. The chaser because they're denying that they are attracted to men, and the CD because they have a dream they're a woman.

This exactly plain and simple.
If you-are gay ……ok
Just don’t play games…I know where others have said that was the ultimate feeling like a woman having a man be after them.
But then cannot go there…you can be hurt or much worse.
Just no stupid games .

NaughtyMichelle
08-02-2025, 11:25 PM
Be honest about who you are and what you want. Sometimes it takes awhile if you want a real relationship. Less time if you're just looking for fun. :o

JohnH
08-03-2025, 11:58 PM
As a man, my relation to other men is simply be a buddy with them, to discuss things of interest to men. I can be dressed en femme at church but at coffee hour I typically hang out with the men as a fellow man.
There is absolutely no way I could ever be romantic with another man.

John

Sabine7
08-04-2025, 03:01 AM
I used to be neither dating with men nor being attracted by them. However, when in female mode I have a need to be as close to the real femininity as possible. The female side of my soul simply requires that. I used to have fancies about being dominated and men's part alone which seen to be attractive to me.

SophiaRose
08-04-2025, 09:09 AM
If you?re interested in a little deeper dive into this topic read Alice in Genderland. Youll find it very interesting.

Jessica Secret
08-04-2025, 03:35 PM
Great thread Tammi! I have a boyfriend and it's amazing. So many perks. I can be my feminine self and he's extremely accepting, supportive and encouraging of my dressing. I don't specifically feel pressure to be more feminine other than in the bedroom where I'm plenty feminine anyway especially when we're about to be intimate. I'm extremely comfortable with who I am, and having such a great boyfriend gives me that confidence to be my fem self that I don't think I would have with a woman.

Philippa Jane
08-05-2025, 07:01 AM
I have had an online interaction with a guy.
He was recently divorced and was looking for company. The conversation was all about me and him trying to find out as much as possible without giving as much back.
There was no suggestion from me that I was TS. He thought I was a GG.
I eventually found the conversation too hard to continue as it was so one sided.
Here is a thought. Was I ever like that?

One of my gym friends is a retired university professor from Hawaii. On Monday he surprised me by asking that since I had transitioned why did I not go out with men.
I guess it was hard for him to get his head around the fact I am still attracted to women. Perhaps the right man has not come along.
Nah, that is not it at all.

racquelr
08-05-2025, 09:31 AM
When the clothes come off you're just two blokes having gay sex.

That's why you don't take off all of your clothes. :heehee:

Genifer Teal
08-05-2025, 01:39 PM
Well, I had a guy proposition me before even having a date. He effectively said, "let's f". I said, "but I don't even know you yet. Aren't you gonna take me out first? " His response was, "oh, you're just like a real woman."

I doubt he realized the compliment he paid me. I'm not saying all guys are like this one, but a lot of them are more DTF than LTR.

Natalie5004
08-05-2025, 02:11 PM
Philippa,

I listen to men speak often. They are not great communicators and at times they can even be very verbal. Not so much a conversation but a monolog.

Just saying.

Philippa Jane
08-06-2025, 09:39 AM
Natalie.
I hear you. So many of the ladies I sit with say exactly the same thing. They just want to talk about themselves (not like my one) and rarely listen.
I wonder if being a cab driver helped me or am I just a natural chatterbox?

mirima1992
08-09-2025, 01:12 PM
I don't look for anything romantic, have no interest in dating a man. However, in gg mode Mirima is interested in strictly physical interactions with the right guy. Those are easy to find.

Georgina
08-09-2025, 01:18 PM
I dress in women's clothes and that's as far as it goes. I have friends that know and are brilliant. I love chatting when I am dressed but I am not attracted to men.

CrossKimmy
08-09-2025, 09:47 PM
Did you mean to rhyme Georgina? hehe

I have thought quite often of having an encounter whilst dressed. I find the idea very enticing and sexy tbh. I've learned that I am more bisexual than anything.

SaraLin
08-10-2025, 06:46 AM
I can't say I've ever been romantically interested in men.

Except for one, and that still surprises me.
He's a good friend. He knows and accepts both sides of me, which is a major blessing.

One day while talking about random stuff, I realized that I could be happy as his girlfriend, not just his friend.
This really rattled me, and was quite a shock.
Never before, and never since, have I EVER felt this way about a man. I always thought I was strictly interested in women.

Huh.

And before you ask - no, I didn't tell him. He's straight. I'm happily married. There's no way I'm going to mess things up with something so -um- random.

Meg
08-10-2025, 10:08 AM
As I read through this post, I was reminded of all the wisdom and intelligence in this group. Wow, how insightful. It is wonderful to be surrounded by you all. I have toyed with the thought of being with a man while dressed, but have never experienced this. I can only say that I dress to be less masculine. I love the softer side. Hugs, Meg

Alice92
08-10-2025, 03:18 PM
It's too hard to be the girlfriend of a guy who wants a relationship with a woman. It's easier to be the boyfriend of a gay man who agrees to treat you like a girlfriend when you put on a dress.

JenninSC
08-21-2025, 12:45 PM
Did you mean to rhyme Georgina? hehe

I have thought quite often of having an encounter whilst dressed. I find the idea very enticing and sexy tbh. I've learned that I am more bisexual than anything.

I'm definitely bisexual as well and have settled on the fact that I'm a crossdreamer. Part of that is wanting to be the woman in a sexual encounter.

Jessica Secret
08-24-2025, 03:16 PM
It's too hard to be the girlfriend of a guy who wants a relationship with a woman. It's easier to be the boyfriend of a gay man who agrees to treat you like a girlfriend when you put on a dress.

Great point here Alice. In my case my boyfriend is bi but but what you described is pretty much our situation.

Petals
08-26-2025, 03:56 PM
No! Never have and never will be interested in dating a man! I am a man who likes to dress as a woman occasionally!

Ressie
08-27-2025, 09:54 AM
I've been with men sexually but it's never been romantic. It's come closer to being romantic with other crossdressers. Although I do feel more fem when I'm in a man's arms. That's just me I guess.

JohnH
08-27-2025, 10:24 AM
No! Never have and never will be interested in dating a man! I am a man who likes to dress as a woman occasionally!
I'm a man and I will never be interested in dating a man! Also, I dress like a woman all the time.

John

DianeT
08-27-2025, 10:51 AM
@SaraLin Aren't we complex beings... makes the world more interesting.

@Alice92 I like your solution, consensual and unambiguous. It makes sense.

oh to be rachel
08-27-2025, 11:22 AM
I'm just going to put this out there.
When dressed as a woman and a guy makes a pass at you, it is super bewildering.

_jenni_
08-30-2025, 07:36 AM
Sometimes the path is a long and winding road. While dressing has helped me to express who I feel I could have been all along. The experiences I?ve had with men echos what others have said?it?s generally lacking reciprocal feed back or expression and can feel purely transactional.

Rochal Tukque
09-08-2025, 12:27 AM
This is kinda funny and probably something many has pondered. I?ve had a couple of male friends that know I?m a CD both of them at times have asked to go out. Well I certainly called their bluff. Both of them chickened out totally, wow just fun and they couldn?t handle it. Had a couple interesting encounters with CD?s that went farther. I found you better be not only like minded but open minded. Both ended to be ?Men? in drag. Just getting there little thing done and oops all done. No fun. I would assume they?re people out there that probably would work out. Might have get scratched by a lot thorns to find a rose. LOL

Sherry Ann Evans
09-09-2025, 08:28 AM
It's always important to remember that gender is a separate thing from sexual preference.

I happen to be bisexual and a crossdresser.

So, I thoroughly enjoy it when guys are interested in Sherry Ann. :)

What I do NOT understand is when straight CDs say they're soooooo offended by a guy coming on to them. That is ridiculous. If we're dressed pretty, and a guy says so, then take it as a compliment and be flattered! There is no reason to get all defensive and jerky about it.

@tammileetilliso
09-09-2025, 05:52 PM
Sherry, I agree with you. A compliment is always welcome, whether it comes from a man, a woman, or another CD.

Sandi Beech
09-09-2025, 07:29 PM
I agree as well. I have gotten compliments from men and women, and trust me you know when it is a compliment vs someone that is just being a chaser. The last time I went out in April, I got a high 5 from a guy. No problemo. He was just saying my outfit was cool.

Sandi

Maria 60
09-09-2025, 08:23 PM
I'm not going to lie when I'm dressed I sometimes think about getting attention from a man, but believe it's probably just like a gold stamp that I'm attractive and excepted as a women. But then I really think deep into it about it and I really don't find men attractive. Just like its said here it would be interesting being with a men dressed like a women but if all the clothes did come off, WOW! That's pretty much just plain gay sex. I guess I now know why I never did it.
Great post and great and interesting responses.

CrossKimmy
09-11-2025, 01:45 PM
I love complements! But I?m like why put on these beautiful things and not at least blush a little bit when you get attention.

AshlyEmilyJane
09-13-2025, 03:07 PM
I hate how it?s so difficult for them to understand we?re still attracted to women

Fiona_44
09-13-2025, 03:48 PM
I enjoy compliments from both women and men. The more, the better. But I value the comments from females more than those from the men. A female is who I'm trying to emulate so getting input from females carries more weight.

AshlyEmilyJane
09-13-2025, 04:12 PM
I strongly agree

lorenahem
09-13-2025, 05:19 PM
I'm new to this site and I don't know how to intervene properly yet. Regarding this matter, I must say that I've been very feminine since I was a child, with a body that always resembles a woman's. I've always wanted to be the wife of a man who would respect me, as a cross-sex woman, and treat me like a real woman, loving me and me loving him, like any other partner. After three relationships, I've come to the conclusion that this is impossible. Men aren't romantic and come to us looking for nothing more than sex.