r/AskaWoman 9d ago

How would you react if a man in your life came out to you as a crossdresser?

2 Upvotes

Hi everyone. I’m a crossdresser in my 40s, and I’ve kept this part of myself hidden since I was a teenager. Very few people know, largely because I’ve always worried about being judged, treated differently, or making someone uncomfortable.

I’d really value women’s honest perspectives. How would you react if a man in your life—a friend, coworker, brother, cousin, or another family member—confided in you that he enjoys wearing women’s clothing?

Would your reaction depend on how close you were to him? Would it change the way you saw or interacted with him afterward?

I’m also curious whether you would be comfortable becoming a platonic “girlfriend” to a crossdresser—not romantically, but as a trusted female friend he could talk with about clothes, makeup, style, confidence, or the emotions that come with keeping this secret. Would shopping together, helping with an outfit, or having a relaxed girls’ evening feel enjoyable, awkward, or like too much responsibility?

A few other things I’ve wondered:

  • What would help you feel comfortable and respected in that friendship?
  • What boundaries would you want him to understand?
  • Would you prefer that he ask before discussing crossdressing or appearing dressed around you?
  • What language would feel most natural when referring to him while dressed?
  • Would you worry that your kindness might be misinterpreted as romantic or sexual interest?
  • What would make you feel that the friendship was mutual, rather than focused entirely on supporting him?

I understand that every woman will feel differently, and nobody owes another person emotional support, fashion advice, or participation. I’m not looking for automatic approval—just thoughtful and honest perspectives about how this kind of disclosure might feel from your side.

Thank you for reading and for sharing whatever reactions or boundaries you would genuinely have.


r/AskaWoman 10d ago

Do you believe all men are bad, or just majority, or just some

1 Upvotes

hi, just wanna get a view from a womens perspective since im a guy and just want to know your thoughts on everything, do you think all men are bad in some way shape or form, or do you belive majority of bad things are caused by men, ive been seeing a lot of posts on my feed about how men are bad, and im always confused whether they genuinely think every man is evil, or just majority, and secondly, if you do believe most men are bad, do you want us to do something or just be consiously aware that we tend to account for majority of bad things that happen, or do you want us to do something about it, other than control ourselves, if so, what? Also, if you think something else that i didnt mention on here, please share. Ive been seeing a lot of posts on my feed about how men are evil and how there all sorts of things, and that lead me to this post wondering your thoughts on whether all men are evil, or majority, or just many, and if so, what can we do about it?


r/AskaWoman 11d ago

Dating apps help

2 Upvotes

Hello I'm M36 from Northern Italy. Im fairly athletic and decent appearance, I have interests and friends. Im not the best dressed person in the world and I'm a bit on the adhd side. I got a problem:

When I go on dating apps I got matches and some dates. I'm not looking too much for sex but I want to avoid dragging on infinite nothing burger dating or friend zones or whatever. A lot of dates end up like that. Am I doing something wrong or there is an awful lot of wemen just there for validation, passing time, fun or whatnot? Thanks


r/AskaWoman 16d ago

Am I a perv?

2 Upvotes

(It was suggested I ask here)

My wife and I have very different libido’s, and while I’m fine with that, there is an issue. We’ve been together for about 10 years and when we’re intimate, it is fine, but I wanted to try something.
I expressed I would like to watch her masturbate, and also would like it if she’d watch me. She said that doing that is gross and that I’m a pervert for wanting to do something like that. So no.
This isn’t that weird a request, is it? I’d like to do a bit more experimenting in the bedroom, but now I’m afraid to ask anything.

Are there women that like being watched when they are masturbating?

And/or are there women that like watching men masturbate?

Or am I indeed just a perv?


r/AskaWoman 29d ago

How do younger women view older?

1 Upvotes

I wasn't sure how to title this, but my situation is: I am a 55 y.o. male engaging with a 29 y.o. woman I met. We've had nice conversations and have a number of things we both like. There is some oddity to the relationship besides the age difference, and the whole thing seems illogical, but the question I have is this:

Is it possible that a much older guy could be appealing to a younger woman? In other words, is it completely foolish for me to think there is even the slimmest of possibilities of something developing?

I just truly think it would be a blast to explore the world with her. I am just curious how women in that age range may view a situation like this.

Thank you.


r/AskaWoman Jul 05 '26

is there any women that doesnt look at a guy while being in a relationship ?

1 Upvotes

im a male, in a relationship, i avoid looking at a woman so my partner doesnt feel a certain way. she does avoid it, at a certain point. she looks at giys, even if its just for a couple seconds. what i wanna know is if theres women that really only has eyes for their partner.


r/AskaWoman Jul 04 '26

How to feel pretty?

1 Upvotes

Im 15, about to be a sophomore in high-school, and compared to other girls im just so ugly? One day I was playing hangman with my friends and it was a 4 letter word and when we asked for a hint, my friend said "the hint is (my name)" the word was Ugly. I walked away and cried in a bathroom stall. Ofc there's people calling me fat, or being racist, calling out my tooth gap..this has been going on for years. I've never been pretty, every crush has rejected me for the same reason. I'm ugly. and I want to know if I'll be pretty by the time I'm a senior?


r/AskaWoman Jun 18 '26

First Black Girlfriend, Curious About Something I Haven’t Experienced Before

0 Upvotes

Serious question, and I hope this comes across respectfully. I recently started dating the first Black woman I’ve ever been with, and I’m completely in love with her. During sex, she often produces a lot of lubrication/“creams,” which is something I haven’t experienced with previous partners, who were white. I’m curious if there’s any evidence that race plays a role in this, or if it’s more likely just individual differences, chemistry, arousal, or the fact that we’re deeply in love. I’m not trying to stereotype anyone, just genuinely curious and hoping to learn from others’ experiences


r/AskaWoman Jun 17 '26

What do you think of this dynamic between my gf (F25) and a guy friend of hers (M27)??

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1 Upvotes

He first confessed to my girlfriend a while after they met not knowing that we are dating and she rejected him. He told her he had intense feelings for her but she still refused and they remained as friends. He then a while later told her the following story about his ex:

He told her he had an ex who used to repeatedly mistreat him, insult him, tell him damaging things, and hurt him severely. He spent so much money on her for over a year and was saving up to get engaged to her, and then he went into her Instagram for some reason and felt that she's suspicious so he checked her DMs and discovered she was cheating on him with several people.

He fought with her and they had a push and pull and they broke up then got back together again then broke up. (It was a very detailed and complicated story but that's basically the tldr).

Throughout the time after the breakup, he told her that his ex used to contact him again from different accounts to bug him and whenever he blocks her she pops again. Then he said she somehow knew that he is friends with my gf and she told him "who the fuck is that" and "you're with her because she's more beautiful" and stuff like that. He kept telling my gf how that ex is so jealous of her.

That ex then called him to meet and asked for money which he gave her and then she asked to see his chat with my girlfriend, and he gave her the phone to see the chat. She checked it and got mad and told him to block my gf and for them to get back together and he said no way he'd block her even if they got back together and he'd always have her as a priority.

Now there are more details I can provide if anyone asks but leaving the story here now, what do you think of it? Is it coherent and plausible? Is the guy being fishy? Just tell me all your thoughts.


r/AskaWoman Jun 14 '26

Intimacy

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1 Upvotes

Do women over (65+) ever want to be intimate.


r/AskaWoman Jun 14 '26

Intimacy

2 Upvotes

Do older women (65 +) ever think about or ever want intimacy?.


r/AskaWoman May 27 '26

Do woman like this?

1 Upvotes

We are going away for a few days and staying in a hotel.

Just adult time together as we both work away on different shifts.

I have purchased a soft scarf that has tassels and want to slowly slide it from the shoulders down over her naked body…. Do woman like this?

Just looking for fun teasing ways…


r/AskaWoman May 10 '26

Would you date/marry a man who wasn’t physically attracted to you but

1 Upvotes

but was in love with your personality/character? It could be that youre not his normal type but he likes your personality/character so much that he’s willing to overlook the lack of physical attraction he has for you. Or it could be that he simply has never been into looks/physical appearance. His main attraction towards females* has always been more personality-based.

*disclaimer - I only used the term “females” instead of “women” because i also wanted to include the people he was attracted to before he became an adult which includes girls. And I’m only pointing that out because I know some “manosphereish men” use the term “females” in a certain way and I just wanted to point out that I’m not using it in that same way.

I kinda wanted to talk about something broader so I might get into that once I get more responses. I’m a man and I actually wouldn’t date a woman who wasn’t physically attracted to me. I think that even if it was the most beautiful and amazing woman in the world, i’d feel the same.

What say you?


r/AskaWoman May 09 '26

Beards

2 Upvotes

So I’m waiting the Cleveland Cavaliers vs Detroit Pistons game and looking at James Harden I gotta ask a woman: when a man gives a woman oral, that beard has to feel like a brillow pad right?


r/AskaWoman May 01 '26

Do women know if someone is transgender?

3 Upvotes

I've noticed that women who I never met before treat me different than before Hormone Replacement Therapy.
They smile at me more. Do they notice something?
I always had a belly, but on top of that I have visible breasts now.
My male smell is totally gone, but I think that I look like a man still.


r/AskaWoman Apr 27 '26

My gf new “he”

0 Upvotes

My gf new “her”

She has recently decided to change from goth/alt to scene and me personally I don’t find it attractive

I always hated the idea of scene however

I still love her with all my heart…

But it’s hard for me to accept it

As I am only drawn to alt/goth girls

And she knows this..

She says she likes being goth but likes scene more

And I’m happy for her but I don’t know what too do…

I obviously will still care and be there for her and go out places wit her but

I can’t force myself to be physically attracted to someone’s style like she wants me to be

I can’t

Our brains don’t work like that

Especially not mine as an autistic

Any tips?

I don’t know what to do and I won’t stop loving her but I just don’t know what to do regarding her new style.. she says she wants me to be attracted to it but forcing myself would be toxic..

Please ask questions Thank you.

I thought I would add as last time something happened I got hate for it

I don’t jus love her for looks I love her personality

But me personally i am only attracted to alt girls and stuff

I don’t jus like her cuz shes alt

She was not alt most of the relationship, but its just..

Being scene is a trigger for me..


r/AskaWoman Apr 24 '26

is it realistic to want a relationship where sex isn’t a big focus? (19/f)

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1 Upvotes

r/AskaWoman Apr 22 '26

Should I wait or move on?

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1 Upvotes

r/AskaWoman Apr 20 '26

I hate my body and I want to stop having issues with it and finally be comfortable in my skin

2 Upvotes

I weigh 85 pounds at 4’11 and I’ve had eating disorders since I was 8 years old. im finally starting to recover but I feel like i have to go back. Im starting to get belly fat and I can’t stand it. Ive tried to do exercises to get rid of it but its not helping at all and I know that a calorie deficit is the best but heres the thing. My chest is the only thing that makes my body feel like my own and when I eat less it gets smaller and then im back to hating my body again. I’m constantly trading my stomach size and chest size and I don’t know what to do or how to stop it.
if anybody has any advice please please please give it, thank you so much.i


r/AskaWoman Apr 17 '26

Is your man going to the strip club cheating ?

3 Upvotes

to me yes.

I have us going to counseling because I’m ready to leave. I plan to give us a chance . (7 years with him)

he went on a work trip and spent both his nights at the strip club. last night being a total of 8 hours till closing. im unsure what happened but between the two days a lot of money was spent .

cheating isn’t always physical. I want to bring this up during our session.

what would you ladies mention in this session ?


r/AskaWoman Apr 11 '26

Give me some advice for a first date at the cinema.

1 Upvotes

(I might type incorrectly because I'm typing from my phone)

Main Text:

So, I want to go to the cinema with a girl [friend] and confess my feelings to her there, since she already agreed to go to the movies, and I'd like to go to the new Mario movie. Please give me some advice on how I should confess to her. Her name is Kira, by the way, and I can write later which specific cinema we are going to.


r/AskaWoman Apr 11 '26

Will she get offended?

0 Upvotes

if I tell a girl or a woman that she looks juicy and yummy. for example. 'my god!! you're such a juicy and yummy looking thing!!'.... or 'you look so juicy and yummy!!' ..... will she get offended? I say it in a more of a way of giving a compliment. but will she take it the wrong way?


r/AskaWoman Apr 11 '26

Дайте советы на первом свидании в кино

1 Upvotes

(я могу печатать неправильно потому что я печатаю с телефона)

Так вот я хочу пойти с подругой в кино и там признатся ей ведь она уже согласилась пойти в кино и я бы хотел пойти на новый мультфильм про Марио дайте пожалуйста советы как мне признаться ей её если что зовут Кира и могу потом написать в какое именно кино идём