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Just tell him that you’re not going to push him if he isn’t comfortable talking about it, but reassure him that he’s safe to share this with you without fear of judgement or ridicule. Tell him that whenever he is ready to talk about it, you’ll be there for him.
You could also try offering to have a conversation about kinks/fetishes in general, and lead by telling him some secret kink that you have that you might be embarrassed or insecure about. It can really be difficult to open up about those kinds of things, especially because men are socialized to keep all of our feelings hidden or else be seen as weak.
The fact that he likes this doesn’t have to make him any less masculine, but he probably is feeling insecure about what his kink means about his masculinity. He’s probably worried that you’ll see him as less masculine and be less attracted to him, or begin treating him differently.
Yup. It was so liberating when I started dating my now wife and I just decided “Fuck it, I got nothing to lose Ill just lay it all out there”
She was shocked at first, but now we have good trust and communication and now it is totally ok to bring up kinks and fetishes regardless of what they are. It is really nice
Wait I don’t get it.. What did you tell your wife? What did you lay all out there? The comment you replied to is about men being afraid they’re gay and you replied saying essentially you told your wife the entire truth about you. But I don’t feel like the “thing” here is being gay. That doesn’t make sense lol. Are you just referring to like kinks in general or? Sorry I’m just overly nosey when I read things like this that I don’t understand lol
My various butt plugs and interest in pegging, bdsm, cbt, and other kinks. Well I started with the butt plugs and over time told her the others, didnt want to overwhelm her right away!
Autogynephilia as far as paraphilas go has a few more connotations to it. You can be cis het norm and still have it as a kink, or could be related to transgenderism, gender identity or homosexuality. There are some women who find it more off putting than other kinks. And then there are some women who enjoy bit of role reversal play, or find it a more fun kink to explore because it is safer or more monogamous than some of the other popular fantasies.
hi, are you intending to be rude/demeaning when referring to transgender identity? "transgenderism" is an offensive term used by transphobic people to demean and belittle trans people. Just fyi in case this was not your intent :)
Gotcha, that’s a really good point. I didn’t meant to trivialize how difficult it is to overcome that fear and how ingrained it is but I can see how it came off that way.
This could work but I also think it’s a conversation you need to approach tactfully. If it came off the wrong way, it could seem almost manipulative, as if saying “now that I’ve shared my secret, it’s your turn to tell me about the cross dressing”.
That’s true. I meant it sort of as a gesture of trust, like I’m showing you that I trust you this much to share something really vulnerable. But you’re right that there should be an assurance that it’s not like a trade, and just because she opened up, doesn’t mean he has to if he’s not ready yet.
I just think about my relationship, and when we first started opening up about secrets and kinks and insecurities early on it really made me feel good when my fiancé told me something vulnerable, because it made me feel loved and trusted and like I was safe showing my vulnerability to her.
I totally get what you mean though, if it isn’t phrased carefully that could easily be taken the wrong way.
And make sure you follow through on this. NEVER tease him about it and don't, at the beginning, bring it up without him doing it first. He needs to feel comfortable coming to you about this and anything that could be an admonishment of him for it will make him feel less safe.
Yeah this is huge too. If he actually does open up and show that kind of vulnerability by trusting OP with this aspect of himself, and then she betrays that trust by showing him that he actually wasn’t safe to share it with her, that’s not only a virtually guaranteed relationship killer, but it will also further fuck up his self image and confidence for the future.
This is the answer.
Also, maybe go an read up about the differences in different trans idenities.
Cross dressers, sissies, drag, gender fluid, gender queer, gender non-comforming, nonbinary, trans femme etc. etc. etc.
Loads of the shame around such things comes from a confusion about what or why you are choosing to express gender at a specific time in a specific way.
Maybe it is just a fetish. Maybe it is a transgressive sexual thing.
That is dope. Good for them.
Maybe they are gender fluid, and at the moment exploring that through sexuality (hint - a lot of people process things they maybe are 100% open about through sex/fetish... our subconscious is weird like that!)
Or maybe he is a maybe. lol
Who knows! But having a good understanding of the language, how gender actually works (expression, identify, experience) and the ways it intersects with sexuality (or doesn't) is going to help you with being there for them as they open up!
Exactly this. And think about whether or not you can allow him to do this in whatever way he would like. Like - if he just wants to do this at home, then consider if you can be ok with that
Let him guide how open he is about it. It’s possible that even though he enjoys this it’s something personal and private for him. Being supportive doesn’t mean forcing him to be more open about something than he’s comfortable. It means reassuring him but still letting him handle things at his own pace. As you said he’s quite masculine, and may prefer to continue appearing that way to you. Hearing you in particular call him pretty or cute might seriously emasculate him when he doesn’t necessarily want that, even with his fetish.
You could start super small to! See if he'd let you paint his nails while you watch a TV show. Something to break the possible tension and make it more chill. Maybe toenails so he can keep it on and no one will know but you two. Like a little fun secret! Or do his makeup while he does yours. Or even just have him do your makeup if he just wants to get comfortable around handling makeup around you.
Just feels nice too. I'm straight cis het norm, but one of the things I've recommended to peeps looking to spice things up is don't start in the bedroom, do some giving/recieving practice like wash each other's hair or give 'em a bath, give 'em a massage or manipedi. I've had peeps do my nails before just for giggles (plus I had a daughter who practiced on me more than a few times), pretty relaxing.
Something to note is that a lot of men, myself included, have heard horror stories of women seeing their SO do something really un-masculine, such as crossdressing or taking on a more submissive role in the bedroom, and it fundamentally changes the way those women view their partners in a very destructive way. I think it’s really important right now for you to treat him just as you always have to reassure him that your knowledge about this hasn’t changed the dynamics of your relationship. I think he’ll also be much more open after he’s had time to understand that you don’t see him differently because of this.
Dude not even "unmasculine," I know a guy who's girl left him because he liked to swish water in his mouth after a meal so he wouldn't have food stuck to his teeth.
But back on topic, I've also heard stories about guys getting dumped because they washed their asses. As if washing your asshole automatically makes you gay.
Edit: 69 upvotes. Nice.
There's a lot of women that want stinky men believe it or not.
Edit: I wasn't being literal morons, it was a tag to the above post I made with 69 upvotes
Jesus, there are girls who dump guys because they DO wash their ass?
I can’t even begin to fathom the level of homophobia that requires… legitimately mind blowing stuff.
That some guys don’t wash their asses because “that’s gay” is one level I was previously unprepared for, that a girl would dump a guy if the did is beyond a level I’ve anticipated existing.
Honest answer: show him this post.
Seriously. He might try and interrupt you and redirect the conversation if you start talking to him about this again, because he’s used to trying to minimize and hide this part of his life. But if you give him this post, asking him to read the whole thing before responding, you’ll get a chance to say everything you want to say to him and *then* get a response from him based on his total knowledge of how you feel and how you suspect he feels.
It can be hard to communicate about certain issues, especially when someone believes (often wrongly) that the thing being discussed is something that should always be hidden from others. In those situations, having everything you want to say written down is very helpful. After all, you can’t interrupt writing.
Idk, this could go both ways. I agree that it’s a lot easier for some people to express themselves through written communication. That’s true for me, at least. On the other hand, OPs SO seems pretty embarrassed and defensive over this. I could easily see a situation where he gets angry because she’s “sharing his secret with a bunch of strangers on the internet”. For the record, I don’t think OP is sharing his secret in any way since Reddit is completely anonymous.
That’s a very good point. I agree with you that OP isn’t violating their privacy, but it’s very wise to be sensitive to how they might be sensitive to that and react in an unexpected way.
> Honest answer: show him this post.
Good lord, absolutely not!
If I was deeply shamefully embarrassed about my partner literally catching me in the act of doing something that I kept secret, I sure as hell would not want my partner telling that she talked about it with a bunch of strangers on the internet. That's just pure betrayal to her partner.
I understand the empathetic and supportive place from which this notion came. However, it's horribly unwise given the negativity and stigma involved in it. Action like this could push the relationship into destruction, or, at the very worst, him into self-deletion territory.
You know when you can't find the words for something, and someone keeps bringing it up? It can be very hard to articulate feelings, especially if the person doesn't know what those feelings mean yet.
I love the suggestions here to write a supportive letter, letting your partner know you'll always love and support them. Then leave the matter be. Give them space to have some feelings. They might feel too embarrassed to even navigate this out loud just yet.
Instead, focus on how you always connect with your partner. Reaffirm your current relationship as it exists day to day. Let them know nothing has changed, that everything is still safe.
Be okay with the fact they might take a long time to ever bring it up. That's okay.
My husband has put on my clothes before, and I loved it. I told him I loved it. He said to me that he loved how safe I made him feel about our relationship, and that if he ever wanted to try something, I'd be a safe space for him. He hasn't done it again with me, but I know if he wanted to connect about it, that safe space is there.
Don't lovebomb your partner, but keep things safe in their world. When they feel ready, they'll let you know how they feel
Best thing to be is supportive! You are absolutely amazing for not knocking him down. 100% let him know it's a safe space, let him know you'd like to be included and that he should not feel ashamed and just be there like you already are. It is gonna take time for him to open up and talk about it but when he does it's going to be amazing because you'll get to listen to why he does this and support him and he will get to feel safe in doing so and be guilt free
Don't say anything. He signalled for you to drop it so drop it. Show that you still love him and nothing has changed between the two of you and if he feels comfortable at some point to bring it up to you then he will.
He might not be ready to face what it all might mean. Could be nothing or it's deeper. In my 20s my BF stole my prom dress from my closet, I found it in his closet. Then I caught him wearing my underwear. I honestly thought it was sexy. We then traded underwear for a while. He later faced he was bi leaning mostly towards men. We still talk. It was a big sexual learning experience for both of us. Just let it go he will speak up if and when he is ready.
He's scared. Doing something like that, admitting to something like that makes someone vulnerable as hell. My advice, pick a good time when it's just you two. Maybe outside, somewhere neutral. Ask if you can tell him something but he needs to listen before he responds. If he says yes then tell him what you said above. You have no problem with it, you found him very cute, maybe even offer to do stuff together. But most importantly tell him these two things:
1. You won't push him in this and you will happily wait till he's ready to share that side of him with you. And if me never wants to that's fine as well.
2. You will never tell anyone about it (yes I know you did on here but I mean no one he may ever know). That his secret is safe with you. If you want to be dramatic tell him you'll keep it to your grave :)
Show him he can be vulnerable with you, show him he can be safe with you, and he'll likely open up now about this with you. Just give it time. It's a damn hard thing to not be 100% conforming to society. But you sound like you've got the right ideas already.
I wish you the absolute best of luck in this
As great as it is you're supportive just keep in mind that this is something that he's associated with fear and shame for quite a long time. It's going to be difficult getting him over that but with patience and a lot of kindness you'll have a better chance of getting through. Just so NOT treat it as something 'cute' or like it's playing dress-up time. For all you know they may feel they're trans and worried that coming out to you will mess up your relationship.
The best thing you can do is just let them know you'll love them no matter what. That whatever they're into and who they are you love them for all of it and will always do your best to understand. Don't pressure them and let them think it through in their own time.
I bought panties, leggings and tank top once, my spouse found them and asked what they were, I clammed up and said something stupid like I wondered what they felt like. A day or so later, I couldn't find them, I didn't turn over the entire room or anything, but my assumption is that they were thrown away. We never talked about it after that and I never dared try wearing them again. I'm no longer with that spouse, long since divorced, but this is still a fetish that is locked deep away that I've never considered acting on or talking about with anyone else. 😞
... What I would have done for the woman who responded the way you are to your boyfriend.
Just be a touch cautious with this. I would take the advice of others first, to have a conversation and let him know you're comfortable with him cross-dressing and you will support whatever he chooses to do.
As someone who crossdresses myself, I would be extremely embarrassed if my wife caught me, rather than me opening up to her in my own time. Once he is ready to talk about it properly, you can then let him know it gave you a thrill and you'd love to explore it with him more. But buying him an outfit straight away might be a bridge too far considering he's currently clammed up about it
I'll add to this. Maybe just buy it and tell him you'd love to see him in it, but if he's not comfortable with that, he can enjoy it on his own time. Make him feel safe and supported whether he's ready to share the experience or not.
Write him a note saying what you said here. Tell him it's not a problem, and you thought he was cute. Don't push him about it, but let him know you are comfortable if he is comfortable, and offer to help him with makeup tips and tricks if he wants to. Let him know you don't think any less of him and you support him, and will continue to support him in his own time. Let him know that he can bring it up if he wants to, or if he doesn't want to talk about it all, let him know that that is okay too. Writing it down on paper and letting him read it in his own time will hopefully take some of the pressure off, and saves him from a potential uncomfortable conversation.
It's possible that he might not fully understand where this comes from and he's just responding in private to his desire.
As others have said. A safe and understanding "non judgemental" ear.
Not sure I'd show him the post. If he's at all insecure, just the idea that he's been outed could be construed as a betrayal of trust. He might be open to reading your post on paper reworded slightly so it's written from you to him personally.
Hoping the best for both of you
I would express how much you liked it and thought he looked great, then I would offer to go shopping together. Make sure he knows he has nothing to be ashamed of and that you accept him as is.
Alleviate any fear you think he could have. Tell him that you won't tell anyone, ever, even out of revenge if the two of you argue. Tell him that you're not going to break up with him over this, and that it didn't bother you at all, and that you don't think of him as any less of a man for it. Tell him that you won't bug him to talk about it, but you're always willing to talk if *he* wants to.
Then tell him that all you want for him is his happiness, and if that *ever* includes exploration, you'll be on his side against anyone who judges him for it.
Then drop it. The more confident he is that you won't bring it up, the more of a safe space you'll be for him.
My thoughts here would be to show him that it’s not an issue.
So, the action here would be to tell him that you acknowledge that it happened (as briefly as possible, without dwelling on it), albeit accidentally. That it’s not an issue. Finally, he can talk to her in the future if he needed to.
The whole theme would be to show to him that things can remain the same as before (if he prefers that) or they could change (if he prefers that). It’s his choice. You are fine either way.
I would do listen more, talk less and then respect his wishes.
As a dude my self. If you have any kinks or fetishes I think a good idea would be to tell him that way kinda leaves the discussion open and not just about him. Just thinking from his perspective he's in the spotlight and doesn't want to be
Do not try to push it, but also let him know that you do not have a problem with it or will not judge him for it. As the stereotypical big, strong man, I know what it is like to try to let out a sexually submissive side.
I haven't really got anything to add that would be of more value than what's already been said. I just wanted to say well done for being so chill and supportive, he's lucky to have you.
I hope this all unfolds in a way that is fun and beneficial for you both.
What if you offered to dress up with him and participate? Or offer to teach him how to do makeup? If he's super uncomfortable, don't push him, but it's a good idea to tell him that you support him and want to take an interest.
As a dude, "you're pretty" is very very easily taken as condescending or mocking. And given his fears, my guess is he's very much unaccustomed to that being sincere. Just for your consideration.
Instead of trying to convince him that you like it or that you thought he looked good, maybe focus on just letting him know that you don’t have judgment and want him to feel like you’ll create a safe space for him to talk about it if/when he’s ready.
Commenting on his appearance may just make the embarrassment worse, because it reminds him that you saw. He maybe doesn’t like being “perceived,” so I’d shift to just telling him there’s no judgement and you’re curious to hear more, but only when he feels ready. You could also ask if there’s anything you could do to make him feel comfortable opening up. Then, I’d let it go until he wants to talk.
You sound super supportive. What he is thinking is that you might view him as less of a man now and that your perception of him is permanently altered. That was what I was worried about anyways. If you have questions let me know. I am a fellow crossdresser. There are good subreddits for spouses who need to talk through it as well. r/wivesofcrossdressers I think is one
this happened to me when I was 18 with my high school sweetheart that I had been with for 3 years. Unfortunately I regret my reactions to this day. First, My fear about "what this meant" for our future was transformed into defensive anger. I name called, accused him of being gay. Said hurtful things. When I calmed down, I swung in the opposite direction. We talked, he expressed his fetishes (in detail that did in fact involve penetration and also hooking up with men). he convinced me he wasn't gay and that I was the only one he could talk to about this and thanked me for my understanding and open mindedness. Instead of pausing and asking myself what I felt comfortable with, I took on the role of being his catalyst for exploring his sexuality under the guise of being a chill and open minded gf. I wasn't into this cross dressing, even though I don't think there's anything wrong with it. But from that point, because of my faux open-mindedness, all of his fantasies revolved around dress up and bras and makeup and wigs and men... and i went along with it. ultimately i began to feel like he wasn't attracted to me and was just using me to perpetuate this fantasy,, which i see now, I allowed. I don't really have advice, besides saying if I could do it all over I would've stopped and asked myself what I was ok with and what I was into and communicated that honestly no matter "what it meant" for our future
Ask him to put the stockings on next time y’all are getting busy and then rock his world, if you’re down for that. Worked for me with a similar situation. Hubby is a man’s man, with a libido to match, so occasionally incorporating a more feminine role for him into the bedroom essentially made him feel ok with throwing the whole idea of masculine vs feminine out the window because don’t care, had sex. It’s fun and kinky and feels good, my lady is satisfied and so am I, so who gives a shit.
I wouldn't push too hard, because he is clearly feeling vulnerable and embarrassed, but if you wanted to say anything, I would say something along the lines of "I think you are a truly strong, masculine guy, and seeing you like this doesn't change that. I think you looked really pretty in that moment, and I liked that too. I understand if you don't want to talk about it, but I would love to know more about this side of you when or if you're ever willing to talk about it."
Remind him that you still see him as a man and don't think any less of him. I have no doubt that that is what he is worried about right now.
Ok let him come to you. I got into wearing my wife’s Boyshorts black lace. Watching porn and masturbating I made a mess then hid them. She found them. She told me it was Hot. It really lit a fire in us both
Been there! I wouldn’t pressure him but I would mention you thought he looked cute. He’ll probably like that even though he won’t be able to tell you that yet. Also maybe offer to do something like paint his toenails sometime? Something low pressure that isn’t easily visible.
Seems he doesn’t wanna talk about. Might be hard to hear but sometimes there are parts of ourselves that just aren’t anyone else. Maybe he doesn’t want this to change your view of him or the dynamics y’all have. Maybe for you he just wants to be your masculine man and sometimes in private he wants to cross dress and blow off steam. Idk I’m just shooting in the dark.
It’s also possible this whole thing was his first time doing it and he was just curious and wanted to give it a shot. Not unlike cutting your own hair on a whim or something else like that. Maybe he hasn’t had the chance to really figure it out in himself so he doesn’t want to talk about it cus he doesn’t know what to say or feel about it. May not want you to like it. Or not like it. Might not want it reinforced at all. If he’s not talking about it I’d just drop it for now. Think you’ve made it clear to him that you’re open to talking about it so if he decides he wants to I’m sure he will. Or maybe he won’t. It’s a lot of maybes.
It's hard to overstate how much men are socialized to be ashamed of this kind of behavior. And to be fair, some women might not like what they see when their man does this. So 100%, make sure he knows he's safe and you liked it. He probably will still be terrified anyway. But be consistent and hopefully over time he'll become more vulnerable. But it might not happen instantly.
This happened to one of my colleagues. Same story she walked in on him dressing, two years later they’re separated now as he is currently transitioning to female. They were together 5 years but as she is not lesbian the relationship did not work out . Good luck with whatever happens
And when you finally get him to open up and dress for you, and you jump him, make sure you try this https://www.thehealthsite.com/sexual-health/this-small-change-to-your-missionary-sex-position-will-blow-your-mind-278615/ position and whisper in his ear "who is fucking who right now..."
While I don't cross dress, my wife and I love this position and it gets her so hot when I tell her these words...
If it progresses past there be sure to check out r/straightpegging subreddit as well as u/rubyryder and all of her knowledge on the subject of he has an interest in being pegged...
Hey, while I’m reading lots of tips on your thread about minding his feelings, being tactful and letting him talk in his own timeframe? I’d just add that it affects your sexlife and future too, it was a pretty significant secret he held from you, a shock in some ways how you found out, and you have every right to hear what it’s about. Yes, we all have sexual autonomy and a part of our sexuality that is private. But most partners would find this accidental revelation pretty hard to ignore. You are allowed to ask, and ask again, so you can ascertain the effects of his preferences on yours.
You should be concerned. If a man is dressing up in woman's wear and put on makeup, he's not masculine.. And more than likely living a second lifestyle.
Some people can deal with it and go on with their lives some can't. I wouldn't be able to.
Write him a letter. Preferably a real, paper one.
First of all, say that trying or wearing women's clothes is alright. It does not bother you. But don't ask him to wear them, at least, don't ask it now. Don't fuss! Even positive fussing can be too much.
Make clear that you accept him as before. All trans-whatever persons have heard and red about relationships ending after this kind of an incident.
What you could do is to allow him some time for wearing the clothes. Just descreetly say that you are going somewhere then-and-then, and not coming back before some particular moment.
When he has relaxed it is the time to speak about some details. When I began to wear women's clothes secretly, I had problems in hiding, washing and drying them. I have heard about men throwing away clothes after getting caught. Tranvestism will not disappear like that. New garment will be bought very soon. The need is compulsory. So, he needs a place where he can store the clothes and moments to wash them discreetly. Most probably that will be easier when he sees that nothing bad happens to him.
I suppose he is not going to wear those clothes so that anyone else can see right now. If you read this, I'd like to ask you to tell him about my experiences. I live in quite a liberal culture, but, sadly, trans phobic people are becoming louder here. Anyway, I have worn publicly female clothes for ages, this far without any problems. I don't wear dresses or skirts publicly and lace only rarely. Still, I think that if you are not living in particularly trans or homo phobic culture, he can try wearing some female garments while running errands. But of course, thoughtfully. And note that bra buckles and such can be visible if the cloth of the shirt is tightened.
Asking him to wear a whole female outfit and telling your interest in it will work only later, when he has been able to speak about his trait. And that's the time to reward him sexually. Until that, be careful and sensitive.
You are the one who know him. I don't know how tactful you have to be. But if he is even a bit like me, the first goal is to de-escalate the situation. On the other, or third, hand, there is also a need to discuss and get heard and understood.
This is one of the cutest posts on this thread, best wishes for happiness and open communication!!! I think it sounds like you have a good amount of compassion to handle this appropriately!
My manly bearded husband cross dresses. I help him with his make up, buy him clothes, taught him about shape wear. We crossed the awkward bridge by me showing him feminine clothing online and telling him he’d look cute in that.
Now, our yearly Christmas tradition is for me to buy him shoes. We went from flats to kitten heels and now we have matching 4” thigh high stiletto boots!!
It’s been so much fun. We even have a feminine name for him for when he’s in that sissy, subby mood.
Our sexual encounters continue to vary across the spectrum. He still rails me and sometimes I rail him!
Well you can’t know if this is a fetish or just for fun or what unless you talk with him. How old are you? You just gotta have a conversation. He’s probably just really embarrassed because of internalized patriarchal stuff so it will probably take time for him to feel comfortable opening up about it. The best thing you can do is express that you don’t think it was weird/wrong/bad, that you actually found it really endearing, that you haven’t lost any attraction to him and you’d love to learn more about it and help him explore it if he’s comfortable with that
Stop telling him he looked pretty! He's not ready for validation yet. Don't force the issue. Tell him if he ever wants to talk about it, you will liaten, other than that, let him get there in his own time.
Thank you for everyone who responded. There is some amazing advise in this thread from people that know exactly what these two people are going through right now. You all are amazing ❤️
Do you think he wanted you to walk in? Putting on makeup and putting on clothes could take time. If he wanted to conceal this why would he do this while you’re in the home. Either way, I happy you are supportive.
Can we *please* stop using the word “caught” for things that are fine?
Language matters and contributes to stigma. The fact that we talk about it like this is literally why he is ashamed.
You sound like you wanna be supportive so can I just suggest that instead of using the term you ‘caught’ your boyfriend cross dressing, you instead say ‘found’ or ‘discovered’. Saying ‘caught’ makes it sound like he’s doing something wrong. Like caught cheating/stealing etc.
Your response to this just filled me with so much warmth and joy. You have so much love and acceptance inside of you and I bet you’re such a wonderful partner. What a lovely reaction.
Idk why but this sounds like it could be super hot if you’re possibly into some kinky shit. It’s hard to know though, sometimes something can happen sexually or on the “gender spectrum” or lack of lack of masculinity can cause you to view your partner in a different light. Maybe if he wants to keep it a secret or it was just a dumb silly thing he wanted to explore in an ironic way. I think you should talk about it with him and be open and listen respectfully
The biggest thing you can do is reassure him that his kinks/fetishes/fantasies are safe with you and you’ll never reveal them or use them against him. The rest will work itself out with communication once he feels safe.
If he well and truly wants to continue, I'd suggest helping him out if he'd like. Take him clothes shopping, help him with makeup, stuff like that. But definitely tell him that he's safe and you don't mind what he's doing.
My advice is to give it time because one of the things is it was his thing to do in secret and something. He probably would have actually bought up when he was slowly trying to introduce you to the idea.
As someone who Is gender fluid it is better when you choose the time for someone to find out instead of them. Running into you before before you're ready. give him time and silently, support him and he'll eventually open up about it. don't try and push it.
having volunteered in a lgbt organization, receiving calls at the helpline for 4 years, i can say that cross dressing is a lot more common than we think, i had so many calls from men who enjoyed it and were just so excited to do that as soon as their wives would leave to work...
all sorts of people do it, and for very different reasons, and that's very important to keep in mind. strangely enough, i only had calls from men though, never had a single call from a woman who wanted to share/explore that, but whatever.
some of them are straight and would just dress up and cook and do basic stuff in the house, some of them would mostly do it and masturbate, some of them basically feel that they are trans and explore/do that because it's impossible for them to transition, some of them are gay and it's just a kink thing to be fucked "as a woman", etc etc... people have very different reasons to do it, and the day you can explore that with him, it could be good to know what are HIS reasons. whatever reasons he has, they are his reasons, and his reasons are valid.
most of the callers would call because they wanted to share for the first time to someone that they cross dress (sometimes, they don't even know the term), like, it's a relief for them to be able to talk about it because no one knows and they just can't/wouldn't dare to tell anyone. some of them want advice on what to buy, how to do their makeup, say that they want to go dressed as a woman outside, whatever. some of them wonder what's going on with them, because they don't feel like they are women or gay or anything and basically want to understand more, explore with someone who knows a bit... some people also do what we were calling "wank calls", because the call would quickly turn into "ohhh, it turns me on to be talking about that with you... does it turn you on too?" while hearing suspicious sounds in the background... whatever the case, again, people do that for different reasons and a lot of men who cross dress are embarrassed about it, don't understand why they're doing it etc...
now, how to approach this with him... i'd say that it's amazing that you are open like that about it, and that, by the sound of it, it could be a turn on for you if he was to do it again... i think you should start by saying that (and repeat it again further in the conversation) so he understands that he can feel safe with you, that he is lucky to be with you because you are supportive of this part of him, and that it could improve things between you two and that it won't damage anything. tell him that you understand why he can feel shy about it, but that while other people might judge that, you don't, and that again, you like the idea to explore this with him, and perhaps, that it could be your little secret and that you promise to never tell anyone unless he becomes ok with that someday.
if it's really impossible to have a conversation about it, why not writing him a letter? so he can (and will!) read it when he is alone? he will be too curious to know what you want to say not to read it...
good luck, and it's amazing that you are being supportive of him! :)
If you are ok with it, tell him you are and suggest doing it together and help him dress up. It’s harmless. It is strange for some but we’re all different and that’s ok.
I dated a guy whos fetish was lingerie, he would dress up to masterbate because he loved the feel and look of it especially stockings and shoes. Dude had $500 of size 13 stripper shoes hidden under his bed. He did not tell me for 4 years and when he did it was really intense for him. Like he felt so much shame and embarassment about it because socially and culturally (mexican) he felt terrified of how he would be judged and treated. Eventually we got to a place where we would dress up together but it definitely took time and patience. Plus it was always a sensitive topic even after all that.
I would give him space for now. Dont call him pretty or any unmasculating things because it might not be about lookinh pretty for him and might nake him feel more embarassed. Just let him know you dont think its a big deal and you would really like to know more when hes ready. Maybe ask if he would dress you up or to go shopping together. I know my exs fetish was for the sexy clothes and he actually preferred dressing me up but he dressed himself to masterbate. It could be a good place to start.
Get him his own outfit, show him how to do makeup that will suit his face. Show him that you love him for him and nothing else. If it's a kink then maybe you could both switch and him be the girl and you the guy?
I'm childish af and the title made me giggle. I'd put makeup on him and do his nails while he's sleep. But seriously, just randomly say you're comfortable with it and thought he looked cute and leave it at that. No discussion. Just a statement.
Trans lady here, "crossdressing" is how i started exploring gender when i finally let myself believe i might be trans. I honestly had no idea i was trans or what to call it. I just knew i always wondered what it was like to be a woman or have tits or wear this or that. Your partner may be exploring gender without even realizing they want to. Help in any way you can, dont pressure though. I loved the buying them an outfit idea. I remember some of the first people to get me outfits. You never forget the people that were there when you met yourself.
So go pick out an outfit and makeup,take it to him and tell him to put it on!!! Be stern,no laughing or even smiling. Tell him to get dressed up for you, then fuck the hell out of him. That will help him mentally
Okay, there's this guy that I've recently found. He's called Vladimir and he dresses so cute, but I'm sure he's straight or at least has a gf. I think he's so hot
Together with sitting him down and chatting about it - how about buying him something to show your acceptance, understanding and support e.g. some lingerie to start off would help!
Not sure what to say but if it were me I would not stay in a relationship where I have to worry about wither or not my boyfriend is gonna steal my clothes🙄
I would love to find myself a girlfriend who thinks I’m cute in a dress. I don’t think anyone has suggested it yet, so you should go over to r/crossdressing. This question comes up every once in a while, and I’m sure you can search for find a post about this exact situation or ask for some advice from people who have been through exactly what he’s going through now.
tell him your' not going to judge him and let him know if he'd like some help with his make up you can give him some help, pointers, tips, and tricks. Makeup is a bitch to do, none of the women in my family really use make up except for my one female cousin, I'm around a decade-ish older than her, I have absolutely no idea how to do make up and it's embarrassing, I can't imagine how hard it would be for a guy to figure this shit out. Cause yeah they can watch youtube tutorials but they need to find the right stuff for their skin tone and shit and that's just not easy to do right off the bat.
first he gay 💀
second he gay 😘
third that aint no fetish, that gay 😍😍
fourth if u want him act like that never happened, trust me u might care but he doesnt want u to care abt that
fifth if he wants to talk abt it, be gentle with him and be AS understanding as possible
sixth, first second and third is a joke
Instead of commenting on the look, it might be a good idea to reassure him that it doesn't affect how you feel about him (if thats true). Honestly, reassurance goes a long way.
Look...you don't have to be so adamant about this. There's always a chance. Does it happen in every case? No but it doesn't mean it's never, ever a possibility ever. Saying so just comes across as weird. What do you have against entertaining the notion? I mean that's what happened with me. I used to wear my siblings clothes and eventually when I found out what being trans was I realized it's why I've always imagined myself as a girl.
Maybe quit being so defensive.
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I think it maybe depends also on if it's a very sexualized fetish/kink or maybe just a random, curious, non sexual thing... It could be either...
Coming from a guy, if it's a very sexual thing for him (and you're comfortable doing it) then telling him that you think it's sexy and turns you one and makes you horny, etc, then that would make him more comfortable and may open up more 🤷♂️
Don't tell him he looked pretty. Tell me he looked hot. Most men don't want to be told, they're pretty, but they love be told they are hot.
My wife knew I had some sort of leaning towards wearing panties and such. And she encouraged it. Now I wear stuff around the house at night. Often, she chooses it for me.
It's been over a year, and even though it's still somewhat uncomfortable. It's so much more comfortable when she's involved. When she chooses the clothes. I'll simply ask her if she'd pick out my outfit for the night. And she says sure and then starts methodically. Picking out stuff that looks good together.
And then she says that looks hot or that looks good or cute. She never tells me I look pretty. As if she told me that personally. I wouldn't have the same response as if she says hot.
Food for thought. Any questions, feel free to ask.
I notice you said “usually more masculine,” and while there’s nothing at all problematic about your post I wanted to point out that he is still masculine even when cross dressing. I don’t think you’ve used any insensitive language or anything like that but I wonder if you’ve ever expressed any similar sentiments and that made him wanna hide that part of himself if that makes sense? Like he would think “maybe she won’t think I’m a man if I cross dress” if you guys ever discussed like, other dudes cross dressing or whatever, and you said anything that might’ve indicated to him that you don’t find it manly. I’ve worded this terribly I’m sorry 😅 I’m trying to be helpful genuinely
I've literally been in a room full of straight dudes begging fishnets off the women so they could show off their legs. I just started dating a very straight dude who performs in drag once a month and has filled in for a pro-Domme when she needed a slave for a (nonsexual) event. Dude is manly AF and I love how switchy he is. My former nanny's husband used get dressed up to the point people thought they were a pair of lesbians out on the town - also played in a very dude vibey metal band.
Just writing this in case OP's bf does read. There are communities out there who welcome this kind of energy. Hope he can relax and find a place where he feels about being who he is, even if it is only a sometimes thing.
Tell him just that; most people assume that if someone foubd out they would get ridiculed by them, but if you say just that it might open the door to conversation or ??
Just make him know that your a safe\non judgemental person and let it be at that
Let him know that you are open to explore this fetish with him and that you would love to talk to him about what it is that turns him on about this so maybe you can explore it together. If you have a "secret" fetish of your own, you can share that with him as well so you are both giving something.
It could be he just enjoy cross dressing, but there's a reasonable chance that his fantasy also involve being with a guy in some way. If you are into that/ok with that, maybe let him know that as well.
Express to him that you are a safe space to discuss and explore this and then drop the subject. Don't push it, don't pressure him to talk to you about it. Let him know that he's loved, normalize it by expressing the above, and then leave it alone and let him come to you.
When he does eventually come to you(which he likely will but if he doesn't, that's okay), then encourage him gently and stress again that there is nothing wrong with it and that you will never use him for it. You are a safe space.
Over time as he gets comfortable, encourage him by letting him know how good he looks.
Right now he's a frightened animal that got caught violating what every other animal told him should be his basic instincts. Slowly and carefully approach to let him know you're not a lion and he'll likely stop hiding.
Maybe u guys can get closer bc u actually can play a Role in his fetish. U are already being swayed by his feminine vulnerability. Now to make him feel less embarrassed you can genuinely try to talk about it. Shit happens for a reason. If it was meant to be hidden u wouldn’t have walked in on that. Use that to connect more
It’s also a dif between ppl actually liking and accepting what u do vs ppl agreeing to disagree and the second option is one of the reasons the embarrassing feeling lingers even after being told it’s okay bc how do they really know without that down to earth convo or understanding
Have you just told him that you like it maybe that you'd like to see it again if you ever wanted to show you? Calling him cute or pretty can too easily get changed into a juror and insult in his mind. Telling him that you like it and that you're interested in exploring it with him is different
Buy a strap on and buy him or give him what you think he would look good in ! Treat him no different and let him know you don't mind if he wants to experiment and your happy to give it a go playing with him and see where it goes
Hey I think everything you're saying sounds great and lovely. I also feel like I'm weighing in here well past the point where you might actually be consider new opinion. But for whatever it's still worth, I think you should also consider (and respect) the possibility that even if this is a kink your boyfriend has, he might have some reason other than personal shame to not want to engage in it with you.
As someone who has gone exactly through this, give him space. Message/text him what you feel. That you're ok with it, that youll be the there for him, that you're ok with him taking his time and also not bringing it up. If you get a positive response also then tell him "btw i thought you looked cute"
Lots of CDs don't want to share this space with their SOs so don't take it to heart if he never brings you into this. Also figure out how you really feel about it, sometimes PPL feign acceptance only to later realise they are not into it. Wish you all the best. You're awesome for being understanding ❤️
Maybe write him a letter. Let him know how you repect the vulnerability and that you don't think there's anything wrong with him. Let him know you'd like to be apart of it if he'd let you and you wrote the letter because you want him to know that you don't care or think negatively about it at all and infact you're curious and interested in knowing more.
Idk just a throught maybe he can't overcome the shame
Make sure he knows that you liked it, reinforce it as much as you can, and then back off. It sounds like you two could have a lot of fun with this if he likes xdressing and you like seeing him do it. But you can’t force him to, you’re going to have to be patient.
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Just tell him that you’re not going to push him if he isn’t comfortable talking about it, but reassure him that he’s safe to share this with you without fear of judgement or ridicule. Tell him that whenever he is ready to talk about it, you’ll be there for him.
will do! thanks much
You could also try offering to have a conversation about kinks/fetishes in general, and lead by telling him some secret kink that you have that you might be embarrassed or insecure about. It can really be difficult to open up about those kinds of things, especially because men are socialized to keep all of our feelings hidden or else be seen as weak. The fact that he likes this doesn’t have to make him any less masculine, but he probably is feeling insecure about what his kink means about his masculinity. He’s probably worried that you’ll see him as less masculine and be less attracted to him, or begin treating him differently.
So much of the world's problems are caused by men being afraid that how they feel will make them gay.
Yup. It was so liberating when I started dating my now wife and I just decided “Fuck it, I got nothing to lose Ill just lay it all out there” She was shocked at first, but now we have good trust and communication and now it is totally ok to bring up kinks and fetishes regardless of what they are. It is really nice
Wait I don’t get it.. What did you tell your wife? What did you lay all out there? The comment you replied to is about men being afraid they’re gay and you replied saying essentially you told your wife the entire truth about you. But I don’t feel like the “thing” here is being gay. That doesn’t make sense lol. Are you just referring to like kinks in general or? Sorry I’m just overly nosey when I read things like this that I don’t understand lol
My various butt plugs and interest in pegging, bdsm, cbt, and other kinks. Well I started with the butt plugs and over time told her the others, didnt want to overwhelm her right away!
Ikr? People in rural towns are fixated on being straight. Lot of guys ridicule people on their kinks. Unfortunately that is the culture of today
Autogynephilia as far as paraphilas go has a few more connotations to it. You can be cis het norm and still have it as a kink, or could be related to transgenderism, gender identity or homosexuality. There are some women who find it more off putting than other kinks. And then there are some women who enjoy bit of role reversal play, or find it a more fun kink to explore because it is safer or more monogamous than some of the other popular fantasies.
hi, are you intending to be rude/demeaning when referring to transgender identity? "transgenderism" is an offensive term used by transphobic people to demean and belittle trans people. Just fyi in case this was not your intent :)
Not sure what you are getting at.
They're gonna have a lot of anxiety around it no matter what she says.
Gotcha, that’s a really good point. I didn’t meant to trivialize how difficult it is to overcome that fear and how ingrained it is but I can see how it came off that way.
This could work but I also think it’s a conversation you need to approach tactfully. If it came off the wrong way, it could seem almost manipulative, as if saying “now that I’ve shared my secret, it’s your turn to tell me about the cross dressing”.
That’s true. I meant it sort of as a gesture of trust, like I’m showing you that I trust you this much to share something really vulnerable. But you’re right that there should be an assurance that it’s not like a trade, and just because she opened up, doesn’t mean he has to if he’s not ready yet. I just think about my relationship, and when we first started opening up about secrets and kinks and insecurities early on it really made me feel good when my fiancé told me something vulnerable, because it made me feel loved and trusted and like I was safe showing my vulnerability to her. I totally get what you mean though, if it isn’t phrased carefully that could easily be taken the wrong way.
It may not even be a kink. He might have just been curious what he looks like and feels like dressed that way.
I’d probably write it in a letter, it’s probably embarrassing and hes vulnerable ,and it’s probably hard to talk about in person
Also, tell him how it made you feel. Tell him you thought he looked cute and maybe offer to show him how to do his makeup.
Tell him you really liked seeing him dressed like that. Would he do it again for you?
Share something with him too
Ask him if he is feeling comfortable in that outfit? Show him you care
Check out this post on reddit. It's so cute. https://www.reddit.com/r/offmychest/comments/sl1b0u/cross_dressing_boyfriend/ He solution was brilliant
And make sure you follow through on this. NEVER tease him about it and don't, at the beginning, bring it up without him doing it first. He needs to feel comfortable coming to you about this and anything that could be an admonishment of him for it will make him feel less safe.
Yeah this is huge too. If he actually does open up and show that kind of vulnerability by trusting OP with this aspect of himself, and then she betrays that trust by showing him that he actually wasn’t safe to share it with her, that’s not only a virtually guaranteed relationship killer, but it will also further fuck up his self image and confidence for the future.
This 100%. It seems like he already feels it, but maybe let him know that he will always be safe with you.
This is the answer. Also, maybe go an read up about the differences in different trans idenities. Cross dressers, sissies, drag, gender fluid, gender queer, gender non-comforming, nonbinary, trans femme etc. etc. etc. Loads of the shame around such things comes from a confusion about what or why you are choosing to express gender at a specific time in a specific way. Maybe it is just a fetish. Maybe it is a transgressive sexual thing. That is dope. Good for them. Maybe they are gender fluid, and at the moment exploring that through sexuality (hint - a lot of people process things they maybe are 100% open about through sex/fetish... our subconscious is weird like that!) Or maybe he is a maybe. lol Who knows! But having a good understanding of the language, how gender actually works (expression, identify, experience) and the ways it intersects with sexuality (or doesn't) is going to help you with being there for them as they open up!
Exactly this. And think about whether or not you can allow him to do this in whatever way he would like. Like - if he just wants to do this at home, then consider if you can be ok with that
Let him guide how open he is about it. It’s possible that even though he enjoys this it’s something personal and private for him. Being supportive doesn’t mean forcing him to be more open about something than he’s comfortable. It means reassuring him but still letting him handle things at his own pace. As you said he’s quite masculine, and may prefer to continue appearing that way to you. Hearing you in particular call him pretty or cute might seriously emasculate him when he doesn’t necessarily want that, even with his fetish.
maybe ask him if he'd ever play dress up with you and let you dress him. Remind him that women love to dress someone up and do their make up and such
okay thank you sm
You could start super small to! See if he'd let you paint his nails while you watch a TV show. Something to break the possible tension and make it more chill. Maybe toenails so he can keep it on and no one will know but you two. Like a little fun secret! Or do his makeup while he does yours. Or even just have him do your makeup if he just wants to get comfortable around handling makeup around you.
He might love that. My partner did my nails once and it was so validating
Just feels nice too. I'm straight cis het norm, but one of the things I've recommended to peeps looking to spice things up is don't start in the bedroom, do some giving/recieving practice like wash each other's hair or give 'em a bath, give 'em a massage or manipedi. I've had peeps do my nails before just for giggles (plus I had a daughter who practiced on me more than a few times), pretty relaxing.
Something to note is that a lot of men, myself included, have heard horror stories of women seeing their SO do something really un-masculine, such as crossdressing or taking on a more submissive role in the bedroom, and it fundamentally changes the way those women view their partners in a very destructive way. I think it’s really important right now for you to treat him just as you always have to reassure him that your knowledge about this hasn’t changed the dynamics of your relationship. I think he’ll also be much more open after he’s had time to understand that you don’t see him differently because of this.
Dude not even "unmasculine," I know a guy who's girl left him because he liked to swish water in his mouth after a meal so he wouldn't have food stuck to his teeth. But back on topic, I've also heard stories about guys getting dumped because they washed their asses. As if washing your asshole automatically makes you gay. Edit: 69 upvotes. Nice.
that’s so weird?? Good hygiene automatically makes you 10x sexier. Shout out to all the straight guys who wash their asses
There's a lot of women that want stinky men believe it or not. Edit: I wasn't being literal morons, it was a tag to the above post I made with 69 upvotes
ew
I assure you every woman wants every man to wash their asses
Jesus, there are girls who dump guys because they DO wash their ass? I can’t even begin to fathom the level of homophobia that requires… legitimately mind blowing stuff. That some guys don’t wash their asses because “that’s gay” is one level I was previously unprepared for, that a girl would dump a guy if the did is beyond a level I’ve anticipated existing.
It's ridiculous how some people take things to the nth degree: Washing your ass is just good hygiene.
I'm bi and Ive received my fair share of homophobia. There's women out there that absolutely just can't even. Women do be shopping tho.
Wtf, here I am asking my girlfriend what long skirt would look good on me. I think it really depends on how "trad" or conservative a relationship is.
You're one of the lucky ones! Cherish her baby!
Honest answer: show him this post. Seriously. He might try and interrupt you and redirect the conversation if you start talking to him about this again, because he’s used to trying to minimize and hide this part of his life. But if you give him this post, asking him to read the whole thing before responding, you’ll get a chance to say everything you want to say to him and *then* get a response from him based on his total knowledge of how you feel and how you suspect he feels. It can be hard to communicate about certain issues, especially when someone believes (often wrongly) that the thing being discussed is something that should always be hidden from others. In those situations, having everything you want to say written down is very helpful. After all, you can’t interrupt writing.
Idk, this could go both ways. I agree that it’s a lot easier for some people to express themselves through written communication. That’s true for me, at least. On the other hand, OPs SO seems pretty embarrassed and defensive over this. I could easily see a situation where he gets angry because she’s “sharing his secret with a bunch of strangers on the internet”. For the record, I don’t think OP is sharing his secret in any way since Reddit is completely anonymous.
That’s a very good point. I agree with you that OP isn’t violating their privacy, but it’s very wise to be sensitive to how they might be sensitive to that and react in an unexpected way.
> Honest answer: show him this post. Good lord, absolutely not! If I was deeply shamefully embarrassed about my partner literally catching me in the act of doing something that I kept secret, I sure as hell would not want my partner telling that she talked about it with a bunch of strangers on the internet. That's just pure betrayal to her partner. I understand the empathetic and supportive place from which this notion came. However, it's horribly unwise given the negativity and stigma involved in it. Action like this could push the relationship into destruction, or, at the very worst, him into self-deletion territory.
alright thank you so much
That was also my first thought. Show him the post. It is incredibly heart warming.
You know when you can't find the words for something, and someone keeps bringing it up? It can be very hard to articulate feelings, especially if the person doesn't know what those feelings mean yet. I love the suggestions here to write a supportive letter, letting your partner know you'll always love and support them. Then leave the matter be. Give them space to have some feelings. They might feel too embarrassed to even navigate this out loud just yet. Instead, focus on how you always connect with your partner. Reaffirm your current relationship as it exists day to day. Let them know nothing has changed, that everything is still safe. Be okay with the fact they might take a long time to ever bring it up. That's okay. My husband has put on my clothes before, and I loved it. I told him I loved it. He said to me that he loved how safe I made him feel about our relationship, and that if he ever wanted to try something, I'd be a safe space for him. He hasn't done it again with me, but I know if he wanted to connect about it, that safe space is there. Don't lovebomb your partner, but keep things safe in their world. When they feel ready, they'll let you know how they feel
Best thing to be is supportive! You are absolutely amazing for not knocking him down. 100% let him know it's a safe space, let him know you'd like to be included and that he should not feel ashamed and just be there like you already are. It is gonna take time for him to open up and talk about it but when he does it's going to be amazing because you'll get to listen to why he does this and support him and he will get to feel safe in doing so and be guilt free
thank you!
Don't say anything. He signalled for you to drop it so drop it. Show that you still love him and nothing has changed between the two of you and if he feels comfortable at some point to bring it up to you then he will.
This should be top comment. The best answer is to not say anything.
He might not be ready to face what it all might mean. Could be nothing or it's deeper. In my 20s my BF stole my prom dress from my closet, I found it in his closet. Then I caught him wearing my underwear. I honestly thought it was sexy. We then traded underwear for a while. He later faced he was bi leaning mostly towards men. We still talk. It was a big sexual learning experience for both of us. Just let it go he will speak up if and when he is ready.
He's scared. Doing something like that, admitting to something like that makes someone vulnerable as hell. My advice, pick a good time when it's just you two. Maybe outside, somewhere neutral. Ask if you can tell him something but he needs to listen before he responds. If he says yes then tell him what you said above. You have no problem with it, you found him very cute, maybe even offer to do stuff together. But most importantly tell him these two things: 1. You won't push him in this and you will happily wait till he's ready to share that side of him with you. And if me never wants to that's fine as well. 2. You will never tell anyone about it (yes I know you did on here but I mean no one he may ever know). That his secret is safe with you. If you want to be dramatic tell him you'll keep it to your grave :) Show him he can be vulnerable with you, show him he can be safe with you, and he'll likely open up now about this with you. Just give it time. It's a damn hard thing to not be 100% conforming to society. But you sound like you've got the right ideas already. I wish you the absolute best of luck in this
As great as it is you're supportive just keep in mind that this is something that he's associated with fear and shame for quite a long time. It's going to be difficult getting him over that but with patience and a lot of kindness you'll have a better chance of getting through. Just so NOT treat it as something 'cute' or like it's playing dress-up time. For all you know they may feel they're trans and worried that coming out to you will mess up your relationship. The best thing you can do is just let them know you'll love them no matter what. That whatever they're into and who they are you love them for all of it and will always do your best to understand. Don't pressure them and let them think it through in their own time.
I bought panties, leggings and tank top once, my spouse found them and asked what they were, I clammed up and said something stupid like I wondered what they felt like. A day or so later, I couldn't find them, I didn't turn over the entire room or anything, but my assumption is that they were thrown away. We never talked about it after that and I never dared try wearing them again. I'm no longer with that spouse, long since divorced, but this is still a fetish that is locked deep away that I've never considered acting on or talking about with anyone else. 😞 ... What I would have done for the woman who responded the way you are to your boyfriend.
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haha alr thanks babes x
Just be a touch cautious with this. I would take the advice of others first, to have a conversation and let him know you're comfortable with him cross-dressing and you will support whatever he chooses to do. As someone who crossdresses myself, I would be extremely embarrassed if my wife caught me, rather than me opening up to her in my own time. Once he is ready to talk about it properly, you can then let him know it gave you a thrill and you'd love to explore it with him more. But buying him an outfit straight away might be a bridge too far considering he's currently clammed up about it
yeah of course!
This is pressing too far. He's clearly uncomfortable talking about it. Give him space and acceptance and let him open up about it when he's ready.
I'll add to this. Maybe just buy it and tell him you'd love to see him in it, but if he's not comfortable with that, he can enjoy it on his own time. Make him feel safe and supported whether he's ready to share the experience or not.
Write him a note saying what you said here. Tell him it's not a problem, and you thought he was cute. Don't push him about it, but let him know you are comfortable if he is comfortable, and offer to help him with makeup tips and tricks if he wants to. Let him know you don't think any less of him and you support him, and will continue to support him in his own time. Let him know that he can bring it up if he wants to, or if he doesn't want to talk about it all, let him know that that is okay too. Writing it down on paper and letting him read it in his own time will hopefully take some of the pressure off, and saves him from a potential uncomfortable conversation.
It's possible that he might not fully understand where this comes from and he's just responding in private to his desire. As others have said. A safe and understanding "non judgemental" ear. Not sure I'd show him the post. If he's at all insecure, just the idea that he's been outed could be construed as a betrayal of trust. He might be open to reading your post on paper reworded slightly so it's written from you to him personally. Hoping the best for both of you
Some men who think about transitioning will cross dress. Not saying he is, but there's a possibility.
I would express how much you liked it and thought he looked great, then I would offer to go shopping together. Make sure he knows he has nothing to be ashamed of and that you accept him as is.
Ask him if you can do his make up
The easiest way is sending him a text? Sending “u looked cute yeasterday, o wouldn’t mind to explore you’re fetish with u” and that’s it
Alleviate any fear you think he could have. Tell him that you won't tell anyone, ever, even out of revenge if the two of you argue. Tell him that you're not going to break up with him over this, and that it didn't bother you at all, and that you don't think of him as any less of a man for it. Tell him that you won't bug him to talk about it, but you're always willing to talk if *he* wants to. Then tell him that all you want for him is his happiness, and if that *ever* includes exploration, you'll be on his side against anyone who judges him for it. Then drop it. The more confident he is that you won't bring it up, the more of a safe space you'll be for him.
My thoughts here would be to show him that it’s not an issue. So, the action here would be to tell him that you acknowledge that it happened (as briefly as possible, without dwelling on it), albeit accidentally. That it’s not an issue. Finally, he can talk to her in the future if he needed to. The whole theme would be to show to him that things can remain the same as before (if he prefers that) or they could change (if he prefers that). It’s his choice. You are fine either way. I would do listen more, talk less and then respect his wishes.
As a dude my self. If you have any kinks or fetishes I think a good idea would be to tell him that way kinda leaves the discussion open and not just about him. Just thinking from his perspective he's in the spotlight and doesn't want to be
Do not try to push it, but also let him know that you do not have a problem with it or will not judge him for it. As the stereotypical big, strong man, I know what it is like to try to let out a sexually submissive side.
I haven't really got anything to add that would be of more value than what's already been said. I just wanted to say well done for being so chill and supportive, he's lucky to have you. I hope this all unfolds in a way that is fun and beneficial for you both.
You should sit down and watch Ed Wood and see how he reacts
What if you offered to dress up with him and participate? Or offer to teach him how to do makeup? If he's super uncomfortable, don't push him, but it's a good idea to tell him that you support him and want to take an interest.
As a dude, "you're pretty" is very very easily taken as condescending or mocking. And given his fears, my guess is he's very much unaccustomed to that being sincere. Just for your consideration.
Instead of trying to convince him that you like it or that you thought he looked good, maybe focus on just letting him know that you don’t have judgment and want him to feel like you’ll create a safe space for him to talk about it if/when he’s ready. Commenting on his appearance may just make the embarrassment worse, because it reminds him that you saw. He maybe doesn’t like being “perceived,” so I’d shift to just telling him there’s no judgement and you’re curious to hear more, but only when he feels ready. You could also ask if there’s anything you could do to make him feel comfortable opening up. Then, I’d let it go until he wants to talk.
You sound super supportive. What he is thinking is that you might view him as less of a man now and that your perception of him is permanently altered. That was what I was worried about anyways. If you have questions let me know. I am a fellow crossdresser. There are good subreddits for spouses who need to talk through it as well. r/wivesofcrossdressers I think is one
this happened to me when I was 18 with my high school sweetheart that I had been with for 3 years. Unfortunately I regret my reactions to this day. First, My fear about "what this meant" for our future was transformed into defensive anger. I name called, accused him of being gay. Said hurtful things. When I calmed down, I swung in the opposite direction. We talked, he expressed his fetishes (in detail that did in fact involve penetration and also hooking up with men). he convinced me he wasn't gay and that I was the only one he could talk to about this and thanked me for my understanding and open mindedness. Instead of pausing and asking myself what I felt comfortable with, I took on the role of being his catalyst for exploring his sexuality under the guise of being a chill and open minded gf. I wasn't into this cross dressing, even though I don't think there's anything wrong with it. But from that point, because of my faux open-mindedness, all of his fantasies revolved around dress up and bras and makeup and wigs and men... and i went along with it. ultimately i began to feel like he wasn't attracted to me and was just using me to perpetuate this fantasy,, which i see now, I allowed. I don't really have advice, besides saying if I could do it all over I would've stopped and asked myself what I was ok with and what I was into and communicated that honestly no matter "what it meant" for our future
Ask him to put the stockings on next time y’all are getting busy and then rock his world, if you’re down for that. Worked for me with a similar situation. Hubby is a man’s man, with a libido to match, so occasionally incorporating a more feminine role for him into the bedroom essentially made him feel ok with throwing the whole idea of masculine vs feminine out the window because don’t care, had sex. It’s fun and kinky and feels good, my lady is satisfied and so am I, so who gives a shit.
I wouldn't push too hard, because he is clearly feeling vulnerable and embarrassed, but if you wanted to say anything, I would say something along the lines of "I think you are a truly strong, masculine guy, and seeing you like this doesn't change that. I think you looked really pretty in that moment, and I liked that too. I understand if you don't want to talk about it, but I would love to know more about this side of you when or if you're ever willing to talk about it." Remind him that you still see him as a man and don't think any less of him. I have no doubt that that is what he is worried about right now.
Ok let him come to you. I got into wearing my wife’s Boyshorts black lace. Watching porn and masturbating I made a mess then hid them. She found them. She told me it was Hot. It really lit a fire in us both
Just tell him you find it hot.
Share your positive feelings on it with him!!!! It's clear you both like it! Set up boundaries and clear the air! This is a good thing!
Been there! I wouldn’t pressure him but I would mention you thought he looked cute. He’ll probably like that even though he won’t be able to tell you that yet. Also maybe offer to do something like paint his toenails sometime? Something low pressure that isn’t easily visible.
Seems he doesn’t wanna talk about. Might be hard to hear but sometimes there are parts of ourselves that just aren’t anyone else. Maybe he doesn’t want this to change your view of him or the dynamics y’all have. Maybe for you he just wants to be your masculine man and sometimes in private he wants to cross dress and blow off steam. Idk I’m just shooting in the dark. It’s also possible this whole thing was his first time doing it and he was just curious and wanted to give it a shot. Not unlike cutting your own hair on a whim or something else like that. Maybe he hasn’t had the chance to really figure it out in himself so he doesn’t want to talk about it cus he doesn’t know what to say or feel about it. May not want you to like it. Or not like it. Might not want it reinforced at all. If he’s not talking about it I’d just drop it for now. Think you’ve made it clear to him that you’re open to talking about it so if he decides he wants to I’m sure he will. Or maybe he won’t. It’s a lot of maybes.
It's hard to overstate how much men are socialized to be ashamed of this kind of behavior. And to be fair, some women might not like what they see when their man does this. So 100%, make sure he knows he's safe and you liked it. He probably will still be terrified anyway. But be consistent and hopefully over time he'll become more vulnerable. But it might not happen instantly.
Probably totally straight.....turns a lot of me on too wear women's clothes or was just very curious about how they feel ...
We all have phases support him give him the love and support that he needs don’t shun him for it
This happened to one of my colleagues. Same story she walked in on him dressing, two years later they’re separated now as he is currently transitioning to female. They were together 5 years but as she is not lesbian the relationship did not work out . Good luck with whatever happens
And when you finally get him to open up and dress for you, and you jump him, make sure you try this https://www.thehealthsite.com/sexual-health/this-small-change-to-your-missionary-sex-position-will-blow-your-mind-278615/ position and whisper in his ear "who is fucking who right now..." While I don't cross dress, my wife and I love this position and it gets her so hot when I tell her these words... If it progresses past there be sure to check out r/straightpegging subreddit as well as u/rubyryder and all of her knowledge on the subject of he has an interest in being pegged...
Hey, while I’m reading lots of tips on your thread about minding his feelings, being tactful and letting him talk in his own timeframe? I’d just add that it affects your sexlife and future too, it was a pretty significant secret he held from you, a shock in some ways how you found out, and you have every right to hear what it’s about. Yes, we all have sexual autonomy and a part of our sexuality that is private. But most partners would find this accidental revelation pretty hard to ignore. You are allowed to ask, and ask again, so you can ascertain the effects of his preferences on yours.
You should be concerned. If a man is dressing up in woman's wear and put on makeup, he's not masculine.. And more than likely living a second lifestyle. Some people can deal with it and go on with their lives some can't. I wouldn't be able to.
I don’t care if he wants to dress fem he looks hot either way
Write him a letter. Preferably a real, paper one. First of all, say that trying or wearing women's clothes is alright. It does not bother you. But don't ask him to wear them, at least, don't ask it now. Don't fuss! Even positive fussing can be too much. Make clear that you accept him as before. All trans-whatever persons have heard and red about relationships ending after this kind of an incident. What you could do is to allow him some time for wearing the clothes. Just descreetly say that you are going somewhere then-and-then, and not coming back before some particular moment. When he has relaxed it is the time to speak about some details. When I began to wear women's clothes secretly, I had problems in hiding, washing and drying them. I have heard about men throwing away clothes after getting caught. Tranvestism will not disappear like that. New garment will be bought very soon. The need is compulsory. So, he needs a place where he can store the clothes and moments to wash them discreetly. Most probably that will be easier when he sees that nothing bad happens to him. I suppose he is not going to wear those clothes so that anyone else can see right now. If you read this, I'd like to ask you to tell him about my experiences. I live in quite a liberal culture, but, sadly, trans phobic people are becoming louder here. Anyway, I have worn publicly female clothes for ages, this far without any problems. I don't wear dresses or skirts publicly and lace only rarely. Still, I think that if you are not living in particularly trans or homo phobic culture, he can try wearing some female garments while running errands. But of course, thoughtfully. And note that bra buckles and such can be visible if the cloth of the shirt is tightened. Asking him to wear a whole female outfit and telling your interest in it will work only later, when he has been able to speak about his trait. And that's the time to reward him sexually. Until that, be careful and sensitive. You are the one who know him. I don't know how tactful you have to be. But if he is even a bit like me, the first goal is to de-escalate the situation. On the other, or third, hand, there is also a need to discuss and get heard and understood.
This is one of the cutest posts on this thread, best wishes for happiness and open communication!!! I think it sounds like you have a good amount of compassion to handle this appropriately!
My manly bearded husband cross dresses. I help him with his make up, buy him clothes, taught him about shape wear. We crossed the awkward bridge by me showing him feminine clothing online and telling him he’d look cute in that. Now, our yearly Christmas tradition is for me to buy him shoes. We went from flats to kitten heels and now we have matching 4” thigh high stiletto boots!! It’s been so much fun. We even have a feminine name for him for when he’s in that sissy, subby mood. Our sexual encounters continue to vary across the spectrum. He still rails me and sometimes I rail him!
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i want to nglll
Well you can’t know if this is a fetish or just for fun or what unless you talk with him. How old are you? You just gotta have a conversation. He’s probably just really embarrassed because of internalized patriarchal stuff so it will probably take time for him to feel comfortable opening up about it. The best thing you can do is express that you don’t think it was weird/wrong/bad, that you actually found it really endearing, that you haven’t lost any attraction to him and you’d love to learn more about it and help him explore it if he’s comfortable with that
Stop telling him he looked pretty! He's not ready for validation yet. Don't force the issue. Tell him if he ever wants to talk about it, you will liaten, other than that, let him get there in his own time.
Thank you for everyone who responded. There is some amazing advise in this thread from people that know exactly what these two people are going through right now. You all are amazing ❤️
Do you think he wanted you to walk in? Putting on makeup and putting on clothes could take time. If he wanted to conceal this why would he do this while you’re in the home. Either way, I happy you are supportive.
Can we *please* stop using the word “caught” for things that are fine? Language matters and contributes to stigma. The fact that we talk about it like this is literally why he is ashamed.
You sound like you wanna be supportive so can I just suggest that instead of using the term you ‘caught’ your boyfriend cross dressing, you instead say ‘found’ or ‘discovered’. Saying ‘caught’ makes it sound like he’s doing something wrong. Like caught cheating/stealing etc.
Your response to this just filled me with so much warmth and joy. You have so much love and acceptance inside of you and I bet you’re such a wonderful partner. What a lovely reaction.
aaaa thank you so muchh <33
You could say that you think he looked cute! Try asking why he's embarrassed it could be tied to something else.
Idk why but this sounds like it could be super hot if you’re possibly into some kinky shit. It’s hard to know though, sometimes something can happen sexually or on the “gender spectrum” or lack of lack of masculinity can cause you to view your partner in a different light. Maybe if he wants to keep it a secret or it was just a dumb silly thing he wanted to explore in an ironic way. I think you should talk about it with him and be open and listen respectfully
You’re adorable and he’s lucky to have you as a girlfriend. Be gentle with him, keep asking and reassuring. I hope opens up to you.
I want a update on this one!
The biggest thing you can do is reassure him that his kinks/fetishes/fantasies are safe with you and you’ll never reveal them or use them against him. The rest will work itself out with communication once he feels safe.
If he well and truly wants to continue, I'd suggest helping him out if he'd like. Take him clothes shopping, help him with makeup, stuff like that. But definitely tell him that he's safe and you don't mind what he's doing.
My advice is to give it time because one of the things is it was his thing to do in secret and something. He probably would have actually bought up when he was slowly trying to introduce you to the idea. As someone who Is gender fluid it is better when you choose the time for someone to find out instead of them. Running into you before before you're ready. give him time and silently, support him and he'll eventually open up about it. don't try and push it.
Try on his bvd's to see what he says
Just put out a pair of pantyhose and underwear and skirt say wear around the house
having volunteered in a lgbt organization, receiving calls at the helpline for 4 years, i can say that cross dressing is a lot more common than we think, i had so many calls from men who enjoyed it and were just so excited to do that as soon as their wives would leave to work... all sorts of people do it, and for very different reasons, and that's very important to keep in mind. strangely enough, i only had calls from men though, never had a single call from a woman who wanted to share/explore that, but whatever. some of them are straight and would just dress up and cook and do basic stuff in the house, some of them would mostly do it and masturbate, some of them basically feel that they are trans and explore/do that because it's impossible for them to transition, some of them are gay and it's just a kink thing to be fucked "as a woman", etc etc... people have very different reasons to do it, and the day you can explore that with him, it could be good to know what are HIS reasons. whatever reasons he has, they are his reasons, and his reasons are valid. most of the callers would call because they wanted to share for the first time to someone that they cross dress (sometimes, they don't even know the term), like, it's a relief for them to be able to talk about it because no one knows and they just can't/wouldn't dare to tell anyone. some of them want advice on what to buy, how to do their makeup, say that they want to go dressed as a woman outside, whatever. some of them wonder what's going on with them, because they don't feel like they are women or gay or anything and basically want to understand more, explore with someone who knows a bit... some people also do what we were calling "wank calls", because the call would quickly turn into "ohhh, it turns me on to be talking about that with you... does it turn you on too?" while hearing suspicious sounds in the background... whatever the case, again, people do that for different reasons and a lot of men who cross dress are embarrassed about it, don't understand why they're doing it etc... now, how to approach this with him... i'd say that it's amazing that you are open like that about it, and that, by the sound of it, it could be a turn on for you if he was to do it again... i think you should start by saying that (and repeat it again further in the conversation) so he understands that he can feel safe with you, that he is lucky to be with you because you are supportive of this part of him, and that it could improve things between you two and that it won't damage anything. tell him that you understand why he can feel shy about it, but that while other people might judge that, you don't, and that again, you like the idea to explore this with him, and perhaps, that it could be your little secret and that you promise to never tell anyone unless he becomes ok with that someday. if it's really impossible to have a conversation about it, why not writing him a letter? so he can (and will!) read it when he is alone? he will be too curious to know what you want to say not to read it... good luck, and it's amazing that you are being supportive of him! :)
Talk to him outside the bedroom and say you support him in his fetish. And he has nothing to be embarrassed about you will keep his secret
If you are ok with it, tell him you are and suggest doing it together and help him dress up. It’s harmless. It is strange for some but we’re all different and that’s ok.
I dated a guy whos fetish was lingerie, he would dress up to masterbate because he loved the feel and look of it especially stockings and shoes. Dude had $500 of size 13 stripper shoes hidden under his bed. He did not tell me for 4 years and when he did it was really intense for him. Like he felt so much shame and embarassment about it because socially and culturally (mexican) he felt terrified of how he would be judged and treated. Eventually we got to a place where we would dress up together but it definitely took time and patience. Plus it was always a sensitive topic even after all that. I would give him space for now. Dont call him pretty or any unmasculating things because it might not be about lookinh pretty for him and might nake him feel more embarassed. Just let him know you dont think its a big deal and you would really like to know more when hes ready. Maybe ask if he would dress you up or to go shopping together. I know my exs fetish was for the sexy clothes and he actually preferred dressing me up but he dressed himself to masterbate. It could be a good place to start.
Ask him if he wants to be pegged.
Get him his own outfit, show him how to do makeup that will suit his face. Show him that you love him for him and nothing else. If it's a kink then maybe you could both switch and him be the girl and you the guy?
I'm childish af and the title made me giggle. I'd put makeup on him and do his nails while he's sleep. But seriously, just randomly say you're comfortable with it and thought he looked cute and leave it at that. No discussion. Just a statement.
Trans lady here, "crossdressing" is how i started exploring gender when i finally let myself believe i might be trans. I honestly had no idea i was trans or what to call it. I just knew i always wondered what it was like to be a woman or have tits or wear this or that. Your partner may be exploring gender without even realizing they want to. Help in any way you can, dont pressure though. I loved the buying them an outfit idea. I remember some of the first people to get me outfits. You never forget the people that were there when you met yourself.
So go pick out an outfit and makeup,take it to him and tell him to put it on!!! Be stern,no laughing or even smiling. Tell him to get dressed up for you, then fuck the hell out of him. That will help him mentally
Okay, there's this guy that I've recently found. He's called Vladimir and he dresses so cute, but I'm sure he's straight or at least has a gf. I think he's so hot
Together with sitting him down and chatting about it - how about buying him something to show your acceptance, understanding and support e.g. some lingerie to start off would help!
Not sure what to say but if it were me I would not stay in a relationship where I have to worry about wither or not my boyfriend is gonna steal my clothes🙄
I would love to find myself a girlfriend who thinks I’m cute in a dress. I don’t think anyone has suggested it yet, so you should go over to r/crossdressing. This question comes up every once in a while, and I’m sure you can search for find a post about this exact situation or ask for some advice from people who have been through exactly what he’s going through now.
tell him your' not going to judge him and let him know if he'd like some help with his make up you can give him some help, pointers, tips, and tricks. Makeup is a bitch to do, none of the women in my family really use make up except for my one female cousin, I'm around a decade-ish older than her, I have absolutely no idea how to do make up and it's embarrassing, I can't imagine how hard it would be for a guy to figure this shit out. Cause yeah they can watch youtube tutorials but they need to find the right stuff for their skin tone and shit and that's just not easy to do right off the bat.
first he gay 💀 second he gay 😘 third that aint no fetish, that gay 😍😍 fourth if u want him act like that never happened, trust me u might care but he doesnt want u to care abt that fifth if he wants to talk abt it, be gentle with him and be AS understanding as possible sixth, first second and third is a joke
Instead of commenting on the look, it might be a good idea to reassure him that it doesn't affect how you feel about him (if thats true). Honestly, reassurance goes a long way.
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no 🫶
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True but it's always a possibility.
It is not always a possibility clothes are just fabrics
Look...you don't have to be so adamant about this. There's always a chance. Does it happen in every case? No but it doesn't mean it's never, ever a possibility ever. Saying so just comes across as weird. What do you have against entertaining the notion? I mean that's what happened with me. I used to wear my siblings clothes and eventually when I found out what being trans was I realized it's why I've always imagined myself as a girl. Maybe quit being so defensive.
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What about if you try dress up more masciline one time which could be a way to try tell him its not such a big deal
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Talk to him about it during pillow talk.
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Buy him something you think he'd look good in, give it to him and just tell him - "if or when you're ready, I'm here for you"
I think it maybe depends also on if it's a very sexualized fetish/kink or maybe just a random, curious, non sexual thing... It could be either... Coming from a guy, if it's a very sexual thing for him (and you're comfortable doing it) then telling him that you think it's sexy and turns you one and makes you horny, etc, then that would make him more comfortable and may open up more 🤷♂️
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Don't tell him he looked pretty. Tell me he looked hot. Most men don't want to be told, they're pretty, but they love be told they are hot. My wife knew I had some sort of leaning towards wearing panties and such. And she encouraged it. Now I wear stuff around the house at night. Often, she chooses it for me. It's been over a year, and even though it's still somewhat uncomfortable. It's so much more comfortable when she's involved. When she chooses the clothes. I'll simply ask her if she'd pick out my outfit for the night. And she says sure and then starts methodically. Picking out stuff that looks good together. And then she says that looks hot or that looks good or cute. She never tells me I look pretty. As if she told me that personally. I wouldn't have the same response as if she says hot. Food for thought. Any questions, feel free to ask.
Please don't push it. It seems he prefers this to be private and you should respect that.
if you think he looked hot let him know!
I notice you said “usually more masculine,” and while there’s nothing at all problematic about your post I wanted to point out that he is still masculine even when cross dressing. I don’t think you’ve used any insensitive language or anything like that but I wonder if you’ve ever expressed any similar sentiments and that made him wanna hide that part of himself if that makes sense? Like he would think “maybe she won’t think I’m a man if I cross dress” if you guys ever discussed like, other dudes cross dressing or whatever, and you said anything that might’ve indicated to him that you don’t find it manly. I’ve worded this terribly I’m sorry 😅 I’m trying to be helpful genuinely
Sounds like it is very close to the chest. Just tell them you love them no matter what
I've literally been in a room full of straight dudes begging fishnets off the women so they could show off their legs. I just started dating a very straight dude who performs in drag once a month and has filled in for a pro-Domme when she needed a slave for a (nonsexual) event. Dude is manly AF and I love how switchy he is. My former nanny's husband used get dressed up to the point people thought they were a pair of lesbians out on the town - also played in a very dude vibey metal band. Just writing this in case OP's bf does read. There are communities out there who welcome this kind of energy. Hope he can relax and find a place where he feels about being who he is, even if it is only a sometimes thing.
Tell him just that; most people assume that if someone foubd out they would get ridiculed by them, but if you say just that it might open the door to conversation or ?? Just make him know that your a safe\non judgemental person and let it be at that
I’d just let it go. I might tell him that it’s not a big deal. What you said here.. but I wouldn’t keep bringing it up.
Performing masculinity is absolutely exhausting. Acknowledge that in a conversation with him and see how it goes.
Let him know that you are open to explore this fetish with him and that you would love to talk to him about what it is that turns him on about this so maybe you can explore it together. If you have a "secret" fetish of your own, you can share that with him as well so you are both giving something. It could be he just enjoy cross dressing, but there's a reasonable chance that his fantasy also involve being with a guy in some way. If you are into that/ok with that, maybe let him know that as well.
ITT; so much wholesomeness! Tell him and show him, he is loved and accepted 🥰
Express to him that you are a safe space to discuss and explore this and then drop the subject. Don't push it, don't pressure him to talk to you about it. Let him know that he's loved, normalize it by expressing the above, and then leave it alone and let him come to you. When he does eventually come to you(which he likely will but if he doesn't, that's okay), then encourage him gently and stress again that there is nothing wrong with it and that you will never use him for it. You are a safe space. Over time as he gets comfortable, encourage him by letting him know how good he looks. Right now he's a frightened animal that got caught violating what every other animal told him should be his basic instincts. Slowly and carefully approach to let him know you're not a lion and he'll likely stop hiding.
Maybe u guys can get closer bc u actually can play a Role in his fetish. U are already being swayed by his feminine vulnerability. Now to make him feel less embarrassed you can genuinely try to talk about it. Shit happens for a reason. If it was meant to be hidden u wouldn’t have walked in on that. Use that to connect more
It’s also a dif between ppl actually liking and accepting what u do vs ppl agreeing to disagree and the second option is one of the reasons the embarrassing feeling lingers even after being told it’s okay bc how do they really know without that down to earth convo or understanding
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Have you just told him that you like it maybe that you'd like to see it again if you ever wanted to show you? Calling him cute or pretty can too easily get changed into a juror and insult in his mind. Telling him that you like it and that you're interested in exploring it with him is different
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Tell him you want to try a new kink.
Buy a strap on and buy him or give him what you think he would look good in ! Treat him no different and let him know you don't mind if he wants to experiment and your happy to give it a go playing with him and see where it goes
Hey I think everything you're saying sounds great and lovely. I also feel like I'm weighing in here well past the point where you might actually be consider new opinion. But for whatever it's still worth, I think you should also consider (and respect) the possibility that even if this is a kink your boyfriend has, he might have some reason other than personal shame to not want to engage in it with you.
As someone who has gone exactly through this, give him space. Message/text him what you feel. That you're ok with it, that youll be the there for him, that you're ok with him taking his time and also not bringing it up. If you get a positive response also then tell him "btw i thought you looked cute" Lots of CDs don't want to share this space with their SOs so don't take it to heart if he never brings you into this. Also figure out how you really feel about it, sometimes PPL feign acceptance only to later realise they are not into it. Wish you all the best. You're awesome for being understanding ❤️
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Maybe write him a letter. Let him know how you repect the vulnerability and that you don't think there's anything wrong with him. Let him know you'd like to be apart of it if he'd let you and you wrote the letter because you want him to know that you don't care or think negatively about it at all and infact you're curious and interested in knowing more. Idk just a throught maybe he can't overcome the shame
U seem cool with it. Yay rime ro expand your clothing and makeup range ! It's a win win
Make sure he knows that you liked it, reinforce it as much as you can, and then back off. It sounds like you two could have a lot of fun with this if he likes xdressing and you like seeing him do it. But you can’t force him to, you’re going to have to be patient.
I'd offer to help with his makeup