Crossdressing guy

LegacyUser

Please bear with me, this will be a bloody weird one.
If you'd told me I'd be in this situation even a few weeks ago I would have laughed.
I guess thngs are more complicated in real life.

I met this guy online a few weeks ago. He was attractive physically, totally my type. His personality was great, very smart, confident, warm, funny and full of humour and we really hit it off.

Not long into our conversations he started talking about his 'secret' second job - that he spends some nights works in a bar as a crossdresser. As in, a transvestite. Makeup, hair, nail, clothes, the works. He didn't elaborate and to be honest I was so completely thrown that I didn't really know how to react and half thought it was a joke. he's a real lad's lad, very tall and athletic and I guess alpha male you'd say, so this was just a complete shock. He's also got a very respectable job, lots of mates, well-eduated and travelled etc...it just didn't make any sense to me.

We kept talking anyway, I guess my curiosity was peaked and I was full of questions. He told me that it's something he's been doing since he was young (late 20s now). NO-ONE in his life knows about it ("the lads would fcuking die") and his last longterm relationship broke up because his ex found out and freaked out.

He described it as innate, instinctive, something that he's tried to curb over the years but the urge to cross dress always overcomes him and he ends up back in this bar...He describes it as a comfort, a way to express his 'softer' side, and something that is definitely not a choice. As in, he sort of has to do it because it's a part of who he is.

Anyway. We met for the first time about two weeks ago and I wasn't expecting much, given everything he had told me, but I had the best first date of my life. There was this spark and connection between us that I can honestly say I've never felt before (and I've dated a LOT over the years) and it was just perfect. Natural, fun, affectionate, complete butterflies. We've met up a few times since and it's been nothing short of amazing. I'm crazy about him.

Last night I brought up the crossdressing thing again as it's been playing on my mind a bit, and somehow managed to completely offend him, telling him that I wish it wasn't a part of him because it's so confusing and weird to me and I don't know how to process it. In an attempt to be honest and have an adult conversation about it, I managed to make him completely shut down and decide that there's no point in us meeting up anymore because he "can't be half a person again" and there's no way anything further can happen between us.

I feel sad, a bit gutted to be honest and my head is in a complete spin. it's like all the elements were there and everything was just so right....except this thing. To be honest I just don't know HOW to come to understand it, or how it could not be an issue between us, but at the same time, I've never met someone where the chemistry, attraction, conversation was so intense and so magical like this before. My head is just wrecked altogether. I've never met a man like this and don't know how to process it as "just another part of his personality" and not seedy, creepy, weird, a bit perverse. He's sworn to me he's not gay and when I met him I knew this immediately - he's defintiely attracted to me - but I'm having trouble understand the appeal of it to a straight, very masculine man.

Sorry to anyone I'm offending, it's just utterly outside of my experience, and right now I'm torn between knowing I'll never deal with it, and knowing that I'm potentially losing someone really special.

I just don't know what to do. Anyone any advice or insight? This is weird right?

Rosy Posy

It seems a shame to give up on the guy because of this. I guess for me anyway the line would be if it was a sexual thing or more of a hobby. My oh has hobbies that I find distasteful (watching and participating in mma) but that's his thing and I let him get on with it. If it was something he wanted to bring into the bedroom I'd not be willing, and I guess I'd see cross dressing in the same way. Sorry if it's a crappy analogy. I'd recommend you read Marian Keyes' book, This Charming Man, which has a main character with a cross dressing love interest. It certainly opened my mind.

Shrap

whatthefork wrote: »

He described it as innate, instinctive, something that he's tried to curb over the years but the urge to cross dress always overcomes him and he ends up back in this bar...He describes it as a comfort, a way to express his 'softer' side, and something that is definitely not a choice. As in, he sort of has to do it because it's a part of who he is.


but I'm having trouble understand the appeal of it to a straight, very masculine man.

Well OP, I'm not finding this weird, but I am finding it very interesting. I too don't understand the appeal of it to a straight, very masculine man but that's because I don't know enough about men who cross dress, or this man in particular. His explanation above sounds very honest, and he's clearly wanting to help you understand it (as best he can) so that he can start as he means to go on within a relationship. I think that's very commendable.

I'm trying to think how I would have felt if my OH had disclosed this kind of side to himself at the beginning of our relationship, and I reckon I would be intrigued but also hopeful that I could analyse it a bit more with him, ie. what aspects of his masculinity does his cross dressing counterbalance, and although he is heterosexual, does he or would he be into being dressed as a woman in the bedroom? I actually doubt that he is, as I reckon the cross dressing might serve the purpose of (as he says himself) expressing his softer side adequately.

I'm thinking here of the kind of man who is all man in their day to day lives, very much in control of themselves and their emotions and possibly holding a difficult/highly stressed/responsible/dangerous job who, in their sexual lives, feel the need to be dominated by a woman as an expression of letting go of control. Perhaps cross dressers are somewhat similar in that dressing as a woman is a way to let go constantly being in control of their masculinity? After all, why should they be?! I'd personally (if I was in your shoes) like to do some research into cross dressing and why some men feel the need to, but unlike you I more than likely would feel able to accept that people express themselves in very different ways sometimes!

Sorry to anyone I'm offending, it's just utterly outside of my experience, and right now I'm torn between knowing I'll never deal with it, and knowing that I'm potentially losing someone really special.

I just don't know what to do. Anyone any advice or insight? This is weird right?

I guess if you feel cross dressing is offensive, then no wonder he shut down talking about it, probably upset and sensitive about whether he could ever be accepted for who he is by you and reluctant to invest any more in a potential relationship for fear of being hurt and feeling suppressed in his self-expression. I think that was fair enough on his part, if this above is genuinely how you feel.

You know you'll never deal with it? Then do yourselves a favour and let him go. I think it is a pity, as your lack of experience of this area shouldn't necessarily mean that you could never accept it, but if you have already decided that you can't imagine being with someone who uses an alter ego to express themselves and explore a part of their personality that may be difficult to access any conventional way, then you're both better off not going any further.

Is he very creative OP? Certainly, cross dressers appear to me to be people who let a creative spirit manifest in their lives, sometimes in extraordinary ways. I'm thinking of Grayson Perry here - one of the UK's greatest living artists - a straight cross dresser with a fabulous personality and no notion of holding himself back! http://en.wikipedia.org/wiki/Grayson_Perry

Edit: It seems Grayson made a programme called "Why men wear frocks", and I'd say that would be very educational! Must watch it myself actually...

LegacyUser

That I can see, it's no harm or threat to you, requires nothing of you and need not play any part in your relationship at all. So much so, that his ex had no idea until he told her and his friends still don't know.

It seems, as he says, to be just something he needs to express in a fairly limited way. Maybe you could try seeing it as him working in a theme bar and that happens to be the costume, then carry on with a few more dates and see how it goes. Most people in a relationship find something they don't like about their partner - too much football or soap watching, too mean with money or spend it too easily, farts in bed, whatever the hell, but they don't throw away a good thing because of it.

You don't have to commit to anything or go any further than a few dates and in a few weeks of seeing him you'll know if it's a dealbreaker or if you can live with it and you were just caught by surprise.

And as to "This is weird right?" - no, no weirder than the many, many other ways people have of expressing themselves and a whole lot better than some of them.

baby and crumble

Op, I'm coming at this from a different angle in that I dont understand why anyone would find it weird. the majority of men who cross dress are 100% straight. As someone who identifies as a butch woman I understand the appeal of not being tied to one gender all the time. If I had to dress as a feminine woman all of the time I would be incredibly uncomfortable. Gender is pretty much a societal concept- clothes are just clothes, and we have decided what is 'male' and what is 'female'. No-one can be just one thing or another, all of us have likes that if you got really strict about it, are not what society thinks is right for our gender. Men baking; women boxing; male nannies; female soldiers. Luckily, the ones that aren't based on what we look like tend to be acceptable, but as soon as a woman puts on a bow tie or a man wants to wear makeup, everything is 'wrong'. That confuses me. Why is it so different and wrong that this guy wants to wear a skirt sometimes?

Do you honestly want to throw away what sounds like it could be a great relationship because he has a desire to dress up in a way that society has arbitrarily decided is wrong? Seems a bit silly to me.

LegacyUser

Hi OP,
Im a crossdresser , married with kids , iv been a crossdresser since my teens , for me it just a way of relaxing and distressing and has nothing to do at all with sex, im not gay and have no interest in men in a sexual way at all

I have hidden this part of my life very well and only ever told one friend ( female) and she was ok with it, but you become good at hiding it , my wife found out about a year before we got married and went ballistic and i promised id never do it again , but i cant ,it just something i have to do , i think she knows and as long as it not talked aboat or seen she turns a blind eye , ( i only were skirt and tights every now and then and thats all) but i cant explain why i need to do it and im a more relaxed stress freed person after

One thing i think you should know before going into a relationship first is how open he is about it and how would you feel if he is open about it of your friends and family find out in the future

LegacyUser

While you have to admire his honesty in being so upfront about it, it sounds like something you're never going to be comfortable with. He's taking a lot of risks telling you about it.. Is he serious about introducing you to his family and friends (down the line of course) know that you know his secret?

It's extremely common but I wasn't aware that it wasn't of a 'sexual nature' in most cases but I'm not exactly an expert.


I would call it quits OP. Good luck.

power pants

I Cant blame your initial response OP

Ill go against the grain of the rest of the posters and say I would find it very strange to say the least. I like to think of myself as fairly open minded but I think this would be pushing my limits a little too far.

Its more just picturing him in a dress, in a dress and acting all femine. There is nothing wrong either in not being able to accept someone even if they are honest about it.

Its something you need to realize if you can get to terms with the idea or not

bjork

Do you have the same issue with women wearing trousers?



He sounds like a decent guy who was honest and upfront with you from the beginning. He should not have to be half himself. By the same token, neither should you and if you can not accept it that is your personal choice and probably best that the relationship has ended.

LegacyUser

anonymousforme wrote: »

It's extremely common but I wasn't aware that it wasn't of a 'sexual nature' in most cases but I'm not exactly an expert.

It doesn't have to be sexual at all. To quote Eddie Izzard there are a few "weirdo" transvestites that make all the headlines and then loads of "executive" transvestites or male tomboys who just get on with their lives. Yes for some it is a sexual fetish but not all. I've several friends who fall into different brackets of cross dressing - some are professional drag queens which is entirely different to my transgender friends who are very different again straight male friends who occasional wear clothes deemed by society to be 'female' No one looks twice at a woman wearing male clothing. It's all marketing at the end of the day, I've male Asian friends who when visiting Ireland have purchased clothes from the womens sections not realising they were 'womans' clothes as it's a totally different aesthetic in other countries.

Sounds like he's learned from past experiences to be up front about this now and it's up to you wither it's something you don't/can't deal with and can bail before things become too serious.

Neyite

I don't think you get a choice here OP to be honest, it sounds like he has made his mind up - he got burnt before with someone who was ok-but-not-really-ok with that aspect of him and the next relationship he has, he wants someone who is absolutely comfortable with him cross dressing and who wont want him to hide it.

The fact is that he is not obliged to wait for you to feel comfortable with his cross dressing, or get his heart broken in the process when he falls for you, imagines a future with you, but you cannot get over this hurdle. He is entitled to find a partner that fully embraces that side of him along with the great and not so great things that make us unique.

I understand that - we all want to be accepted warts and all by a partner. Have a think about what your passions are - would you be happy if for instance you loved running, felt itchy if you couldn't run, and felt relaxed and happy after it, then you meet someone who says that you are perfect apart from the running bit? That if you hid it, or lied about it, they might be OK about it? We'd be telling you that its not on to try and change a fundamental part of someone and to run (pardon the pun)from him. Would a lifetime of hiding your runners and running gear, lying to someone you love and sneaking out behind their back to do what makes you feel good in yourself be any way to live?

I think your post is very honest and even though by being honest to him you've lost him romantically, it was probably the right thing to do.

LegacyUser

Thank you all so much for the responses. Especially those who have personal experience and a lot more knowledge about this than I do. It's been massively helpful.

It's not a sexual thing to this guy and he's made that very clear. He's not attracted to men and doesn't want to dress up in the bedroom or anything, that's not his thing. We haven't had sex yet but I know from what we've done that he's very dominant sexually and it's not going to impact on that in any way.

He's literally described it as someone else did above - almost like a hobby but deeper, something that he's passionate about and something that relaxes him. Early on he told me that 'being a man can be difficult' because of the social and behavioural expectations and that him being very alpha male means there's sort of no outlet for being 'soft' and emotionally expressive or whatever, and this is what the crossdressing serves for him.

After last night I thought i'd never hear from him again, which would be weird as we've literally been chatting and communicating non-stop since we met several weeks ago. But this morning he messaged me and told me that he was excited about seeing me again too, but that if I genuinely have a problem with it, that's that as far as he's concerned. Because he's had a relatinoship before where it plagued him and there was a lot of intolerance and he can't go through that again.

He said he doesn't know how he would like it to be between us but that he doesn't want to have to hide or or feel bad or shameful anymore. And that no-one in his life knows (he told me early on because it's sort of easy when someone is a faceless randomer on the internet) and it's not something he does every day or even every week. But that he needs to do it, it's who he is.

So I've told him that it's something that I don't understand and I don't know how I feel about it - because at this stage that's the god honest truth - all I know is that i've met someone who i've clicked with in ways that i've never experienced before, and he's been nothing but honest and honourable and a better guy than most, and it would feel wrong to not see him again. and that it will all take a while, but i'm going to ask questions when they crop up and just see how things pan out.

So we're meeting tomorrow and going to a Christmas market together.

I can't pretend I feel anymore comfortable about the whole thing, but I was so upset last night when I thought I had driven him away and the prevailing feeling was one of regret that I might lose someone really special without giving it a proper go. it's still weird to me (and we're not talking about a guy wearing women's tights on occasion - we're talking about full drag makeup, eyelashes, hair, high heels, etc) - i'm still a bit overwhelmed by the whole thing and it's challenging a lot of my own perceptions and prejudices maybe. i never knew that most men who crossdress are straight, for example.

But I think as Shrap suggested i;m going to try to read and research and ask questions and understand as much as I can about this - as well as continuing to meet up with this guy - and see where the chips fall. Life is short and he;s not harming anyone, ultimately. And he's one of the most honest, genuine and straight-up guys I've ever met.

Thanks again for the advice, and i would welcome any further advice or information!

cookiexx

i'd find this difficult too op, so don't be hard on yourself. i think if it was me, it'd probably play into my attraction for the guy, which probably sounds shallow but that's what physical attraction is really.

i don't think a guy in full drag is comparable to a woman wearing trousers either to be honest.

From an academic point of view maybe i'd be curious about the psychology behind it, what drives a manly man to have this instinct to dress up in uber girly clothes and assume this alter ego if thats what it is. that's maybe what's going on with some posters in this thread. but i think if most women were honest it's not something they'd like to see in someone they were romantically interestd in.

Shrap

cookiexx wrote: »

but i think if most women were honest it's not something they'd like to see in someone they were romantically interestd in.

Perhaps I'm not "most women" but now I have met the love of my life (and I can safely say that at this stage), the romantic interest I have in him is in his whole self. There's parts of that whole self I have had to get my head around, but he's so worth the effort because if I hadn't been open minded enough to try, then I'd have missed out on the most wonderful man I've ever known. Knowing what I know now about him, if his particular quirk had been cross dressing, I'd be happily posing with him in full drag today. Much like Philippa Perry does with her husband Grayson - I think he's a very attractive man, and although he's also a very ....em... unique lady from time to time, I can't imagine Philippa would ever wish him to be anything except how he wants to be. And that would be love, right there.

The Princess Bride

Nobody can change how you feel,or who you are,OP.
You've got to go with what's right for you.
But the same goes for this fantastic man-he has to be true to himself.

The only thing I'll say is that it is people who've stereotyped how men and women should behave /act over the years.It's not a rule written in stone somewhere.
Women in skirts with make up, men in trousers with short hair...
Who's to say who's right or wrong,if either, IMHO, some women look hideous in dresses whereas some men have fantastic legs and would look great in skirts. Likewise with makeup.

I think he was incredibly honest to lay his cards on the table from the beginning.There are so many dishonest people out there having relationships, at least he's upfront about who he is.

CaraMay

It wouldn't be for me. The thoughts of my oh walking around the house in a skirt, tights, bra, heels etc would look ridiculous yo me and on that basic I would be less attracted to him. You don't HAVE to be ok with this op

CdeC

CaraMay wrote: »

It wouldn't be for me. The thoughts of my oh walking around the house in a skirt, tights, bra, heels etc would look ridiculous yo me and on that basic I would be less attracted to him. You don't HAVE to be ok with this op

Noone is saying she "has" to be ok with it, but she wants to explore it.

Fair play OP. Really refreshing that someone like yourself can still be open minded and see past your own borders to try and understand someone else. Like a previous poster said earlier who crossdresses himself. He doesn't understand why he does it. I would say that it exists in all cultures and it is not a gay or sex thing. More likely an expression of a part of themselves. perhaps a part that men have to surpress as it is not really acceptable in our society for men to be seen as soft or emotional.
If it doesn't work out who cares, you explored it and you'll be richer for the experience and sure you may stay friends with the guy.

LegacyUser

Thought I’d give a little update.

Met up with the guy again last night. We were both a little unsure of how to act around each other for the first little while, but soon back to the usual chattering and laughing and talking nonsense. We walkd around a xmas market, had dinner and then he came and stayed with me for the night (didn’t have sex!)

It was lovely. I sort of tested the waters with the subject a few times but he just avoided eye contact and got really uncomfortable, so we pretty much left it. I made the odd joke here and there (“I like your top” ‘ “yeah well you can’t have it!”) Much of our rapport is based on this kind of humour and he says he likes that I joke about it, it sort of normalises it for him.

i’m back in work now + texting away as usual and this seems to be the only place he feels comfortable talking about it. He says he feels really awkward when I’m sitting in front of him because it’s embarrassing and shameful and he feels judged. And he doesn’t like the contrast of how we are in real life - the banter and flirting and obvious attraction - to the weirdness and discomfort over text when we have the conversation.

so not really sure what to think. It’s obviously something that he’s very sensitive about - its a pretty big secret in his life that he’s not used to talking about, and then there’s the big negative reaction that his ex had when he told her and how it killed the relationship.

I know one thing for sure - I really like the guy and feel incredibly comfortable in his company, it’s almost like I’ve known him for years. But this is still a big thing that he’ll always have and if I’m in a relationship with him, I’ll by proxy have to carry this secret around too and i just don’t know how i feel about it all.

LegacyUser

CaraMay wrote: »

It wouldn't be for me. The thoughts of my oh walking around the house in a skirt, tights, bra, heels etc would look ridiculous yo me and on that basic I would be less attracted to him. You don't HAVE to be ok with this op

The OP doesn't have to be ok with something but it's her choice as to wither it's something that she can accept as being part of him and clearly the OP is open to considering this as she's started this thread. Is it a deal breaker or something you'd be able to look past. The OP has stated she finds him attractive when they are together and he hasn't asked her to come see him at the bar he cross dresses at or help pick out clothes or anything nor has he demanded she must find attractive when he cross dresses. But cross dressing is part of who he is just like if he was part of a different religion to the OP or a vegan for example and he's clearly learned from past relationships that it's better to be upfront at the start rather then hide it.

I've a friend whose massively into LARPING which is live action role play so once a month he gets dressed up like a fantasy creature or character (fake ears, hair, made outfit the works) and runs around the woods with other people dressed the same having mock battles and casting spells and playing out some adventure they're all in on. His GF does not get it at all, she thinks the amount of money he spends on it is mad but it's his money and he always pays his share of the bills, she doesn't get the costumes he dresses up in or understand what enjoyment he gets out of it but he doesn't look for her to come along or be involved in it. How is that any different? The only difference really is this cultural notion we've attached to gender roles that makes some uncomfortable

LegacyUser

Hi op again
Im coming from this from another point of view, as i stated earlier im a cd and it is a part of me that i wish was there but it is

I cant speak for your friend but for myself, it took me a long time to except this need to dress and i went trough some hard times feeling guity and ashamed for doing it. It is a feeling i would never wish on my son to have to face.

Why do i want to do it ?. I honestly dont know , but its been there since my early teens, but when i do get to dress it a wonderful feeling at time and i feel so much better for it. When you try and suppress it its able to get a powerfull hold over you and i don't believe that any crossdresser could honestly give it up.

Before i met my wife when i was single and living on my own after a bad day at work id come home and put on a skirt while making dinner etc , maybe at the weekend put on some make up and shoes while watching a dvd or match of the day , i never went outside and was terrified anyone would find out ( and i was once)

Its great that your keeping a open mind and that you can see it only a part of the whole person, its only early in the relationship but fair play to him for been honest with you from the beginning

Best of luck

Mr. Incognito

This is a fascinating thread and the reactions are a disparate as I have seen in a long time posting on Boards.

There are a few things that jump out.

He feels that he NEEDS this, that it is a part of who he is and that he gets to express a feminine side to himself that modern men are almost universally denied.

It's not a sexual orientation, its not a lifestyle choice. It's an expression of self, no more than some people have the urge to write, or act, or draw or swim or be nudists.

I am sure that he has struggled with this and has come to be comfortable with who he is as a person. He needs to be admired for that.

He went through a relationship where this was forced to be repressed for fear of judgement, social stigma etc. The relationship ultimately ended because of this.

I think, really that this is an Irish thing. Ireland is a conservative country. If a chap in Las Angelas wants to walk around in dypers for the day no one would bat an eyelid.

You said that he told you and directly after you had the date of your life. This was most likely the result of him saying FINALLY I can be myself, and honest and not be judged and stigmatised and have to hide.

Then you dropped the ball. Badly, and told him that you thought it was weird and abnormal. For you.

For him its no different to having a right or left arm.

I think you need to make a decision, whether what clothes someone puts on from time to time to comfort themselves and feel intrinsically whole affects you in any way whatsoever. Perhaps you are adopting the shame that you think your potentional partner should feel.

I used to have a lot of preconceptions about gay people, until I had gay friends. I used to tell racist jokes, thinking they were funny until I had black and Asian friends.

I think, as we get older we care less and less what others think of us, but oddly we become more judgmental because our minds are closed. Historically this was because we were controlled by a backward, conservative government and church (and still are to some extent)

If you like someone, you must like ALL of that person. Warts and All. Love and Partnership is NOT about finding the perfect person who ticks all the boxes. It's about finding the right person who makes you challenge your preconditioned prejudices about what you thought you wanted.

Love is when you accept that and realise that love is not selfish. It's about sacrificing to make the OTHER person happy. If both partners are doing that its magic. When one is being selfish or trying to match their checklists then relationships break down.

This should be taught to teenagers instead of the nonsense stereotyped physical and monetary achievements that are supposed to matter.

What it boils down to is, do I make this person happy. Do they make me happy. If both answers are yes. That's it. F*ck what anyone else thinks.

Sorry for the philosophical rant.

power pants

I fail to see how you can boil this down to being irish and the church with regards to some people not feeling comfortable with the idea of a man wearing dresses and acting like a woman. Every other country has people who would accept and equally not accept.


Each to their own but don't criticize people for not accepting this.

Im surprised that almost everyone thinks this is perfectly fine. I didn't realize we were so liberal these days. Credit where its due

would everyone be as liberal if their boyfriend/husband walks down the stairs in a mini skirt, stilettos and boob tube?

Mr. Incognito

power pants wrote: »

I fail to see how you can boil this down to being irish and the church with regards to some people not feeling comfortable with the idea of a man wearing dresses and acting like a woman. Every other country has people who would accept and equally not accept.


Each to their own but don't criticize people for not accepting this.

Im surprised that almost everyone thinks this is perfectly fine. I didn't realize we were so liberal these days. Credit where its due

would everyone be as liberal if their boyfriend/husband walks down the stairs in a mini skirt, stilettos and boob tube?

Sorry, I wasn't blaming the church per se, I am just saying that Ireland is historically a conservative country.

There were crossdressers in antiquity and homosexuality was encouraged in ancient Greece for soilders to alieviate stress and bond.

Sexuality was repressed in the middle ages.

It depends on the person. For me, if my mate liked to cross dress I wouldn't care less. I'd take him for a beer in drag if he wanted.

I admire anyone that back their own individuality and say good for them as long as it isn't hurting anyone, and it isn't hurting anyone. It boils down to whether you think its "weird" or whether you'd be okay with it and I think it is distilled down to projecting your own judgment onto that person and blaming them for it. He's okay with it.

Any judgment is entirely her own feelings and she needs to take ownership of those, and yes, sadly she is in the majority.

shalalala

Personally I wouldn't mind at all as long as it wasn't going to make up (clowns petrify me and I would be afraid that it would be done like that).

I think you have found yourself a honest and open man with insecurities. He doesn't want to lie about himself anymore and wants to be happy. You are lucky fir that!

I however do not judge anyone for not being okay with it. But if you cannot be okay with it I would say you both need to finish it sooner rather then later. Also he has to start communicating about it better in order to put you at ease.

IlmoNT4

I dont get what the problem is OP, he sounds like a good person, who trusts you and you feel good around, what more do you want?.....you date the person, not the clothes...

But if its not for you, then move on...you already know the answer. If you cant see past a hobby, I dont know if you'll be able to normalize it for your world. How would you feel about your family knowing? Would you proud to stand by this person, and everything they represent? If the answer is no then you have your answer....

bp

I found the larping example very good - that is possibly more acceptable due to the players not be dressed in clothing viewed as for a single sex...and the movie role models etc.

I think play it by ear. Hand on heart I don't know how I would react if my OH told me that but I think your joke and banter about borrowing the top shows you are open to the idea.

Just be careful that you don't cross a line you aren't ready for yet - exteme example but: borrow my top, he does and suddenly he is wearing female clothes before you were ready (extreme example I know).

My advice would be deal with it as it comes, ask questions and look into the topic. It is a positive sign he confided in you and I hope it works out for all parties, wether you stay together or not

MagicMarker

It's pretty simple really, it's just a bloke wearing unusual clothes from time to time. It's really not a big deal in the grand scheme of things.

Detached Retina

can't log in wrote: »

The OP doesn't have to be ok with something but it's her choice as to wither it's something that she can accept as being part of him and clearly the OP is open to considering this as she's started this thread. Is it a deal breaker or something you'd be able to look past. The OP has stated she finds him attractive when they are together and he hasn't asked her to come see him at the bar he cross dresses at or help pick out clothes or anything nor has he demanded she must find attractive when he cross dresses. But cross dressing is part of who he is just like if he was part of a different religion to the OP or a vegan for example and he's clearly learned from past relationships that it's better to be upfront at the start rather then hide it.

I've a friend whose massively into LARPING which is live action role play so once a month he gets dressed up like a fantasy creature or character (fake ears, hair, made outfit the works) and runs around the woods with other people dressed the same having mock battles and casting spells and playing out some adventure they're all in on. His GF does not get it at all, she thinks the amount of money he spends on it is mad but it's his money and he always pays his share of the bills, she doesn't get the costumes he dresses up in or understand what enjoyment he gets out of it but he doesn't look for her to come along or be involved in it. How is that any different? The only difference really is this cultural notion we've attached to gender roles that makes some uncomfortable

Actually a brilliant analogy, having been a larper and knowing/loving some in the past. it seems to be just an interest,and extension so to speak.
There was a nice series of documentaries on there recently called forbidden love, they covered crossdressing. Lovely couple married 30 odd years, he liked to cross dress was out doing his carpentry in a frock and pearls, beard and all-neighbours and work men who called were like yeah whatever if they seen him, wife still smitten and just got used to it. Was literally a relaxation thing at home for him. Otherwise a mans man.
Just up to how much you like him really

dellas1979

Well, I think its a great thing that he acknowledges his needs (and has told you). Very honest of him. He could hide it as a sort of secret. But why should he? He shouldnt be made feel ashamed for who he is.

To be honest, I wouldnt really care. Am of the vein to live and let live, as long as its not doing anyone any harm. I work with a guy who has a husband. And I only see them as 2 people who love each other. Not as a label. Few years ago, this would not have even been possible. They would not be the great couple they are if they never had courage to live out their needs.

OP, if you cant get your head around it, you are going to have to leave it.

LegacyUser

That's for the continued responses, they really are helping me to get my head straight with this.

I'm coming to the conclusion that I like the guy, he's one of the best and most honest guys I've met in a long time and that's ultimately what matters here. And maybe the fact that he's been so honest and emotionally open right from the start is the reason why we're getting on so well. I'm definitely not used to that and in the past, relationships have started on the wrong foot or been destructive and insecurity-provoking because that same honesty and emotional availability just wasn't there.

im also wondering if me being longterm-single and maybe a bit used to being single has made me a bit of a commitment-phobe and too eager to find fault or reasons to not just let things happen. I know crossdressing isn't your run-of-the-mill relationship issue, but ive also found myself wondering about other incompatibilities - we come from very different family backgrounds for example - and then in turn wondering why i'm focusing on that stuff at such an early stage.

Mr. Incognito wrote: »

If you like someone, you must like ALL of that person.

ultimately this is all i care about. I want the answer to be, screw it, it's a part of him and it makes him great and open minded and adventurous and i love it for that. But then I get uncomfortable when he starts talking about how he's 'heading to the bar' tonight or 'googling makeup tips' and with this lack of understanding as to WHY he has to do it - and then guilt for feeling these things - and it just messes with my head.

the last thing he deserves is someone else who makes him feel shameful and embarrassed about it so if i cant get passed it, i think for both our sakes ill have to walk away. but right now I love his company and look forward to seeing him and I'm just going to go with that for the moment. It's still very early days.

Idle Passerby

A very good long time friend of mine admitted to me they were a transvestite a number of years ago. He admitted it to me very much as if it was something he was shameful of. It was something I had no previous experience of and wasn't sure how to react.The first time I saw him dressed up was quite jarring. it was like hanging out with a stranger, he held himself differently, had different mannerisms and a different name.

As time went on and he admitted it to a few other friends and people were not reacting in disgust, he got more confidence and begun entering drag competitions, he met others into the scene and honestly now it is just a part of my friend. I don't register it as strange anymore when he's in full drag, he's still the same person under it all. He is so much happier that he can express this part of himself and be safe in the knowledge that the people who care about him have no issue with it. He has even said that being able to go out in public has diminished the amount he's compelled to dress up in private, he now has an outlet for that aspect of himself.

Now I realise its one thing having a cross dressing friend and another to have a cross dressing romantic partner. But I do think its something that with a bit of exposure to it you will see its not really a weird, or seedy thing for a man to want to do. Women can wear whatever the hell they want to. Annie Hall made wearing men's suits a fashion statement. Men are very restricted in their wardrobe.

Its understandable that you have qualms, and I understand why this man isn't interested in persuing something with a person who he thinks is critical of his choices, they are hard won Im sure.

I would say give him another chance. Give yourself time to get used to this side of him, go and see him perform. If you still have a problem with it after that, it may be something you cant get past, but you wont know until you try.

DoctorBoo

Recently a wise person made the observation that our society has decided that women should be the "peacocks". They are the ones that dress up, attract attention, and generally exhibit themselves. That's fine, but society doesn't suggest this, it demands it. And clothing and appearance are associated with emotions, feelings and behaviours. Women are associated with emotional outbursts, sensitivity etc. When there are women who don't particularly want to wear "peacock" clothing, people look down on them. They think things like, "She could have made an effort" or "She's pretty, it's a pity she wouldn't do something with herself". When there are men who would like to play the "peacock" role, people think it's weird and often think they are gay.
So, if you look at this guy's situation, is it possible that he finds an outlet for his peacock side through dressing as a woman? Maybe the clothes act as a door to his less "masculine" emotions, allowing him to access his feelings?

LegacyUser

Just thought I'd come back to give a final update.

It's over. For many reasons. And I'm kind of devastated.

just after i wrote this thread things got really really really busy at work - i mean 12 hours a day 6 days a week busy, and we didnt see each other for a few weeks. then i went back home for Christmas and although we were texting the whole time, when i got back things had definitely changed between us.

he started talking about how things had 'fizzled' because we hadn't seem each other for more than a month and then with him starting in a new job, and getting just as busy himself, our lives were virtually incompatible.

i tried to meet with him a few times, both times he 'forgot' or ended up late in work and i ended up sitting at home feeling hurt and disappointed. so we had a proper chat last night and this morning and he told me that he withdrew after not seeing me for so long and started dressing up a lot over christmas and that really changed things because he has decided that he wants to live as a woman and that kind of kills the chance for any romance at the minute. ???!??

ive tried so hard to understand this but there's just no way i can. he doesnt seem to have any answers to my questions - is he gay? will he date men from now on? will he change his name? will he identify as a woman from now on? is he transgender? it's just 'i don't know' to all of those and that all he knows is that when he shut himself off frm me he ended up crossdresssing a lot and realised that that was more 'him' now and he needs to focus on that. he's started wearing tights, bra and knickers to work etc and has 'told a few female friends, who think i'm gay with it' etc and this is basically the way forward for him.

it all sounds so crazy and even to me, totally surreal and bizarre, but i've literally been crying for the last 24 hours, i'm just absolutely devastated because it's the first time in so so so so long that i met someone where it felt the way it did. where i felt like i knew him and he knew me. where i felt like we 'got' one another and it was just so wonderful. we connected. and yet all these issues. i'm just a bit upset and don't know how to deal with it because i know in the real world, im not going to date a full time transvestite and this was never going to work, but that's just completely at odds with the strong feelings that were there from the get go.

so i guess there's the answer. dating a transvestite is not for me. and it's taught me a thing or too about my working life too and how i need to reel that in if i ever want to give a relationship a proper shot. something i've probably known for a while, but has really been hammered home with all this.

thanks for all of the eye opening advice and information. this is not the happy ending i had hoped for.i guess you live and learn x

tara73

you poor thing.
but it's probably for the best, as I read it he's in the process of finding himself, or this female side of him is becoming a huge part in his life and he's expressing it more and more openly.
there seems to be no room for a proper straight relationship, so I wouldn't take it personal, I'm sure he likes you very much but not the way you would like him to.
It's also a very good possibility he's gay and it's his coming out just now. A lot of gay people like to wear womens' clothes.

it's tough for you now, but better a clean cut (and he also explained it to you) than a leading on from his side. so I would say he's fair.

all the best.

Ande1975

OP,

I'm so sorry to read this. A broken heart socks but remember this was just to complicated to to have a proper shot. Don't beat yourself up over work. That happens and people who want to be with you will still be there. This guy used it as an excuse.
He obviously had things to explore but concentrate on you.
Take a step back - you know now what you want in a relationship. This type of connection minus the complexity. That in itself is a great achievement and it will happen
Take care

Idle Passerby

Well done for trying. It was outside your comfort zone and you gave it a good shot. In the end it wasn't your fault it didnt turn into something more. It sounds like he's still unsure of who he is and that would not have made being with him easy. Fair play for being brave.

HiGlo

I think you had a great attitude and open mind to it. Even if you felt you were struggling with it, you were willing to give things a shot.
It's a shame it didn't work out, but it seems like he's on a path of discovery and is still trying to understand who he is and what he wants/needs so it's not a good time for a relationship for him.

Best of luck to you in your search.

tomthetank

honestly op I'm not surprised this has turned out the way it has. And I think you might have learnt a valuable lesson.

sometimes in life that special connection you can have with someone is not enough. sometimes even Love is not enough. The reality of being in a relationship with someone stretches to more than those things, it must involve life compatibilities and both being in the same place emotionally and mentally and it;s pretty clear from reading your posts that those things weren't there.

From reading your earlier posts you seemed to have a good open atitude to it but really were u ever going to be ok with him being a crossdresser? what about if he were to become public about it, as it sounds like he might be doing - how would you feel about that, your family and friends and all the world knowing about it? could you have stood by him and been happy and confident and supportive of this lifestyle choice?
it sounds like he's quite a confused guy who has quite a few big decisions to make and maybe knowign that you werent exactly on board even at that early stage is what made him withdraw. if someone rejected a pretty important part of you in the early stages of dating, would you remain open and excited about them? or would you feel a bit confused and upset and rejected by it all. he'd been thru that before with another partner, i'd say he just didn't want to go through it again.

i'm very sorry for what your going through. But try to learn from it. Stay open and stay brave, but stay true to yourself. you'll feel sad and hurt by this for a while but i think in the end you'll see that it had no potential and it was good of him to end it rather than drawing it out and causing more pain. maybe eventually you'll be able to be friends, he sounds like a good guy. i hope he can come to terms with himself and find happiness and i hope that you can too. best of luck.

Dark Phoenix

aw OP I am sorry it didnt work out. Please dont blame yourself or you work hours. yes work life balance is important but if something can be broken by a few weeks of not seeing each other, then it was never strong enough to survive.
You were open minded but it sounds like this guy doesnt know what he wants just yet and is trying to figure himself out. In our current society it would be far easier for him to hide away that side of himself and date a woman than it would be for him to live as a woman full time so I would imagine he is finding this a hard time himself and its better that he doesnt string you along or get you caught up in it all.