Hi Hannah! You look amazing and I love what you write.
Here goes, I’m 47, my fella is 43, together 4 months.
He loves dressing and I love him doing it, spending time together and sex, pegging etc, me getting to explore being dominant as well as him being feminine and demure.
However, he seems so conflicted by his dressing, he seems to think it’s wrong somehow and that he shouldn’t do it, despite me giving him reassurance, attention and generally loving all of it!
He obviously definitely wants to do it, but why does he seem so distressed sometimes? He’s been doing it for a long time, and says sometimes he’s got rid of all his clothes feeling it’s wrong.
We’re not religious, he’s bisexual and comfortable with his sexuality. Am I missing something? I love him dressing up and we’re talking about going out to an accepting pub dressed once we’ve scoped it out vanilla!
Any insights you have would be very welcome, I hate seeing my princess upset x
Any insights, you say? Okay, let’s give this a shot.
We all have different… motivations, if you will, when it comes to expressing this side of ourselves. What I mean is that some of us dress for sexual reasons, some of us dress to look as beautiful outside as we feel inside, some of us dress to align our physical self with our internal self, and some of us dress as a way of figuring out who we are.
You are clearly supportive and enthusiastic of his feminine side and it feels… genuine, if you will. What I mean is that some of us have partners who aren’t really *into* this side of us but are willing to, well, go along with it even if they would prefer not to. Speaking for myself, I would not want my partner to fake anything with me. What I mean is that some of us have partners who let us wear lingerie during sexy time but deep down they would prefer us not to. I don’t want my spouse to pretend to enjoy something when they really don’t. Sincerity and honesty are important.
If you two are at a point in your intimate moments where you include this side of him, and even incorporate it into the bedroom, my thought is that he likely feels validated and accepted. If not, well, I am not sure what else you could do. Some of us feel guilt if we sense our partners are simply going along with enacting any fantasies or role-playing but if this side of him brings out a side of you that you clearly enjoy (such as the aforementioned dominant aspect of yourself) I can’t imagine he feels distress or guilt in relation to what happens in the bedroom.
It’s not uncommon for someone to feel conflicted about this side of themselves if they were raised in a religious environment. But if that wasn’t his case we might be able to eliminate that reason. Is it possible he was caught dressing as a child and that led to embarrassment and mocking from the person who caught him? Is there lingering trauma from that moment that resonates years later when he dresses?
Purging and getting rid of our clothes is a very common thing. I’ve done this a zillion times and it breaks my heart to think of all the beautiful lingerie I’ve parted with. Some of purge because of guilt, some of us purge because we want to stop dressing, some of us purge out of fear of someone finding our panties.
If he purged in the past, you may want to ask him why.
This side of us is complicated and simple at the same time. But all of us are on some sort of journey of introspection and reflection and discovery. It’s not uncommon for us to wonder what this means and what we want and who we are. Some of us figure it out, some of us don’t.
For some, this journey causes a lot of anxiety. It’s entirely possible your princess is trying to figure out who they are. Perhaps they are wondering if this side of them is just a side of them or if this is something more. Perhaps each time they dress they feel happier and more… complete More at peace. More… right. Perhaps they are wondering if this is who they are and who they are meant to be. Perhaps they are wondering about transitioning. Perhaps not.
It’s possible the distress is because your partner is learning more about themselves and is fearful that this revelation is going to cause a change in your relationship.
I am not a therapist and I don’t know your partner. Like many moments where one is trying to figure things out, I would encourage them to look into counseling. The right therapist can help someone accept truths about themselves and get to the source of many fears and feelings they may have.
I hope this helps.
Love, Hannah
Have a question for me? Oh yes you do. Ask me here!
Hannah McKnight 
as in the 2 versions of the Manchurian Candidate young boys are told from an early age that anything feminine is wrong and to be avoided at all costs. when you grow up that programming still lingers in the brain and is reinforced now and then by society such as using the horrid term “Sissy”. If this couple recognizes that is what they are dealing with it could help a lot–Emily
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100%. Growing up in the 80’s the worst thing a boy could be called was a “sissy.” So there is a TON of shame built into that that takes years and years to even get over, if they even can.
-Christina
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Way to go for reaching out to an expert. Hannah’s right. We could all use a little therapy. Especially these days. My wife the amateur psychologist and voracious researcher has helped our relationship through the years. I don’t know where we’d be without it. I’ll be the first to acknowledge that I need therapy. I should probably be first in line. We’ve tried a couple of times but I’m so closed off that I can’t seem to access how I’m feeling or describe it. It’s as if I don’t know the language. It’s like I missed that day when they were teaching you how to access and describe your feelings. At least there’s a ton of information out there these days. I may also be afraid of what I might find out about myself. I know that I would benefit from professional help. I don’t exactly know why but it’s not easy to reach out for help even though you acknowledge to yourself that you could definitely use some. Thank you Hannah for being a part of my therapy. 😺
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Hannah,
Such wonderful understanding and adivice. I suspect that the acceptance is playing into questioning of where this might lead and thus the internal conflict. Therapy is often the best option to explore what one really wants. Thanks for continuing to offer this service of discussion and exploration.
Tiffany
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This person is Soooooo lucky to have a partner that actually wants him to dress and be her girlfriend . It truly gives her man the freedom to do live on either side of the fence . I respect this lady .
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Apologies for my earlier ramblings. Lol To your point.
I too have rejected that side of myself from time to time. Even after 50 years of dressing and 35 years with my accepting, understanding, supportive and encouraging soul mate. I still occasionally feel the guilt, shame etc. Sometimes I just say fuck it and overcome these feelings because I know they’re bullshit. Though I never went so far as to get rid of my things. It’s always nice to know you’re not alone in this. 😻
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I have gone through these periods myself. It happens when guy identity returns in my brain and through years living around guys that belittle you if you act feminine you feel ashamed to have had feminine feelings and played them out. Purging is very common. Seeing a therapist is a great idea. I was scared to take this step, but you learn that it is entirely normal for people to have these feelings.
Morgan
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I completely understand this gentleman’s issue. You must understand that acceptance of what we do is very very difficult. Cross dressing is not something you can talk about with your best friends. It is very difficult talking to your partner about it because it is embarrassing. Forget talking to your parents. Growing up in the Gen X generation and older, we have been conditioned to accept our gender roles and not to deviate from them. We have been conditioned that cross dressing is taboo and not acceptable. We are conditioned that submissive men are weak. Of course, this is all BS, but your guy friends will forever crucify you if they find out. So, we live with this constant conflict and fear in our head. It is difficult to shake. At times we are good with it and at other times we want nothing to do with it. Regardless of where we are in this forever cycle, we will never be able to get rid of our desire to wear that dress. That desire will always come back. Sorry. Many have tried, but never succeeded. I love that you referred to him as your princess. That is awesome and makes me so jealous as most of us do not have that kind of acceptance from our partners. As he gets older, hopefully, he will learn to not care what others think. He is about 8 to 10 years away from that. Hopefully, he learns that this will be his stress relief and understand that he is hurting no one. Cross dressing is a wonderful way to take a break from the daily grind and recharge. The sooner he sees this the better he will feel. Good luck.
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I’ll take a swipe at this, too. Since they said “pub”, I’m going to assume a UK couple. And the TERF/anti-trans rhetoric over there can be deafening at times. That might be enough to cause someone to question if they want to continue along this track. Sometimes it’s not what’s inside of us that causes us to pause, but the environment that we imagine outside of ourselves.
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I’ll take a swipe at this, too. Since they said “pub”, I’m going to assume a UK couple. And the TERF/anti-trans rhetoric over there can be deafening at times. That might be enough to cause someone to question if they want to continue along this track. Sometimes it’s not what’s inside of us that causes us to pause, but the environment that we imagine outside of ourselves.
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Thank you all for sharing your experiences with others . This type of dialogue helps, even if it is anonymous through a blog. Think about how many others are out there feeling alone, or think that there is something wrong with themselves. Although none of us are therapists, sharing our experience is powerful. About a month ago, I was having a bad day and started to think “what on earth am I doing” and came close to throwing everything out. It was the connection through an email that kept me from following through. That and all the time and money it took to build a wardrobe 😱. Not an easy task as there was a lot of trial and error.
Thanks again to all of you for restoring hope to others.
Nadine
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Andolutely !
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You are wonderful Hannah !
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The best thing to do is try to open a dialogue on why they feel uncomfortable. I am willing to bet that it is based in insecurity stemming from fear of rejection and the internalizing of societal baggage. But for all of the great advice and opinion here, none of us can know what is really going on in someone else’s head. You’re soooo awesome for being so enthusiastic and supportive!
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