[Question] I'm very supportive of his dressing...

A question that I can't fully answer... so I come to you to help me help her!



So I received a question late last month that took me by surprise.  When I see that I have a question, I figure it's about a specific cap, a capping technique, or a question about me.  I've had a few people that wanted information, but they didn't offer much detail.  For instance "i want work in under mistress" was (I assume) a request for information.   Another better worded example was "How do i find a mistress in my area that can handle my footfetish that is very serious"

Normally I can't help too much in these areas.  And honestly, a search of google might provide the questioner with a better answer.  But this time, the question had a lot of detail, and while I'm not sure that I can help, I can at least post her question here and see what we can all come up with to help.  Here is her first question:

Caitlyn - I love your honesty! Briefly, my SO is a cross dresser but, even though he has told me about it and shared only a few times with me, he keeps it very much in the closet. I hate that he has a Flickr account where he shares pics of "her", enjoys comments of what others want to do to "her", etc. He also has a separate email/IM account where "she" has intimate talks or cam chats. He says he is faithful to me and that I shouldn't worry about these sites, but I do. Please help me understand his femme side and if it is just fetish/fantasy/kink or how to handle if he wants to act on it. I'm very supportive of his dressing and I'd love for us to incorporate it into our sex life, but (at least for now) he wants to keep it to himself. Please help. 

She included her email address, so I first responded to her that way.  I didn't initially post this as I didn't want to do so publicly and perhaps scare her significant other.  Here is my first response:


Thank you for sending in your question.  I hope you don't mind that I'm responding via email.  I wasn't sure if you wanted this discussion to be public and I thought this might be a more private way to talk.  Although if you are interested, I can put this up on my blog as one of my 'Question' posts, and let more people chime in and hopefully help out.  

As you don't state it directly, I am going on the assumption that you are a female/male couple.  Some of what I'll say is based on that, but the main thrust of what I'm saying can be also taken if you are a male/male couple.  

I'll take one of your latter questions as it's the easiest to answer, although it's probably not the answer you want to hear.  I really can't help you understand his femme side.  I can't say whether it's simply a fetish, fantasy or kink, nor can I tell you how to handle it if he wants to act on it.  The reason I can't help you there is that there is a wide variety of things that could be going on with your SO.  Cross Dressing just isn't the same for everyone.  

For me personally, its an exploration.  It's a far more emotional journey and fantasy than it is a physical one.  I've tried some cross dressing myself (I've worn panties under my clothes), but my living situation doesn't allow me the privacy to really explore further.  When I do gain that privacy, I plan on trying out more.  But it's not from a desire to 'look' feminine, rather it's a way to find out how I feel when dressed that way.  I'm a straight male who is open about the possibility of being 'more'.  Of being feminine, of cross dressing more fully, of even physically exploring what living and being a woman would be like.  

On the spectrum of cross dressers, I'd be on one far edge.  I'm not doing it because I want to be a woman... I'm doing it to explore how it makes me feel.  If I find enjoyment I may go further, but for now that's all it is.  On the opposite side, you have people that deep down know they are a woman.  They can only express that by dressing up as they feel more appropriate.... as a woman.  Most of these people are generally on a path of wanting/getting  sexual reassignment surgery to change their outward physical appearance to what the feel deep inside.  

Now these are two extremes, and there are plenty of stops between them.  And starting out on one side doesn't mean that a person will continue along the path to SRS.  It sounds like your SO is a little further into the spectrum than I am.  

If your SO is anything like me, this has been a long journey to get to where he is at now.  I didn't wake up one day and just decide to announce the femme side of myself to the world via my blog.  To start making caps involving Trans Gendered, Cross Dressing, and Sissy subject matter.  I started on my personal journey over 20 years ago and there have been many bumps along the way. I still haven't shared this side of myself with anyone that knows me physically, and I'm honestly not sure how I would react if someone knew.  Keeping this side of myself so close and hidden for so long would make it very difficult to share it with someone.  

So he may simply be having trouble sharing something that he has kept hidden away for a long time.  He could also be trying to keep his femme self separate from his male self.  I know when I've been in relationships, I've never thought of sharing my femme side... but my femme self wasn't nearly as developed as it is now and I'm not in a relationship at this time.  But I could easily see your SO as wanting to have you to 'HIMself'.  He didn't want to hide his femme self from you, but he may not want that side of himself to interact with you.  Again, it's not a relationship like you are in, but I have several friends that I only want to communicate with while I'm in my own femme mindset.  When I'm feeling more like 'Calvin' as opposed to 'Caitlyn', I don't want to talk to them.  

I think that the best way for you to move forward is to have a long thorough discussion with your SO.  You should know what this is to him.  Is it just a fantasy like cosplaying?  Is it a sexual thrill?  Is it him exploring himself?  Is it him moving more toward a lifestyle and even gender change?  It sounds like you are very open and accepting of it, and that's very rare.  Let him know that you are open to exploring this with him.  And make sure you emphasize that... that you want to do this WITH him.  A lot of TG and cross dressing fantasies involve girlfriends starting out kind and loving, but end up with them blackmailing and forcing the cross dresser to go far further than they are ready for (posting pictures online, going out in public, interacting with people they know enfemme, having sex....).  It's one of my own darker fantasies... but not one that I would EVER want to really live out.  

You may also want to let him know the advantages of having you explore this side of himself with him.  Helping him learn more about how to properly dress... helping him pick out and purchase new clothes.  Helping him with makeup and hair.  These are things that many cross dressers will scour the internet for as we honestly have no idea how to do it.  Genetic girls have the advantage of not only their mother teaching them many of these things, but girlfriends too.  Having a person taking a hands on teaching approach will help him explore things things further than reading about them, or chatting with someone online about it.  

I hope that some of that helps, and that the two of you can get become closer and really celebrate this side of him.  I'll again offer to put this up on the blog as a public discussion.  Not only could you get more advice on how to proceed, but you'll be an example to many cross dresers and cross dreamers... a girl that supports her SO in his cross dressing is something many people are looking for!

Love
Caitlyn

And here is her reply that I received a couple days ago:


Caitlyn - Thank you so much for taking the time to answer my concern.  I can tell that you really, truly thought about my situation and tried your best to shed some light on it.  I am sure that I am not the only woman in a relationship who is trying to understand her SO.  In this light, feel free to share what you want on your site.  Maybe it will show that they are not alone in this so-hard-to-understand-and-support-kind-of-world.  Having said that, I will address what you shared in order of how I saw it in your response. :)

Yes, we are a female/male couple.  He came out to me a few years ago.  Within days of him admitting he is a CD, he dressed for me and we "tried" to be with each other.  Even though we were both nervous, I thought that, we were a little clumsy with our new roles (girl on gurl) but I wanted to try other things later on.  You know, we would have a "traditional" sex life (girl-guy) and then, for some added fun or when he wanted to bring out his femme side, we would take on the gurl side and we'd enjoy some strap on sex.  Well, the more I fantasized about it, the more I wanted to explore that side.  Sadly, he tucked it away as quickly as he came out.  He didn't want to try any backside play or share any more of "her" - even if it meant talking about his femme persona.  He even went through the dreaded "purge" and deleted all of his accounts and tossed out all of her clothes.  I knew this would be short lived, and, sure enough 6 months later he opened up a flickr and new email account.  However, I thought FOR SURE he would include me in his new chapter.  Sigh.  No.  I was not included (again).

I think, because I am supportive and accepting of his femme side, I wanted to learn more about the "whys". You know, why does CDing turn him on?  Why does he have to go onto CDTG sites?  Why does he have to [sex] chat with other CDTGs or share pics?  Etc.  I just want help in understanding, but he won't go there.  Unfortunately, my brain always takes me to the "whys"...probably because I'm a girl and we always have this undeniable NEED to understand and overanalyze things.  Sorry, that's how God made us.

With what little information he has shared with me, I know he struggled with realizing if he's gay, bi or bicurious.  He is NOT attracted to men.  He's made that very clear to me and has put that on his sites. **Love to dress like a girl!  Only CDTG PLEASE!!** However, he IS attracted to Tgurls and is sexually aroused by them.  I told him he probably has a fetish and that has NOTHING to do with sexuality but I don't think he believes me.  He even went to a medium/psychic and she told him he is NOT gay.  I think this gave him some comfort, but I don't really know.  Anyway, I digress...

He's been CD since he was 9 years old.  Of course, he stayed in the closet and only started sharing pics and getting on sites about 5 years ago.  To my knowledge (and, yes, I've asked and I believe him) he has NEVER been with a CDTG.  He said that dressing makes him feel sexy and allows him to feel horny in a different way.  Unlike you, he does more than just wear panties under men's clothing.  He will have his special dress up time (he doesn't know I know about it and it's always when I'm away and he has plenty of time to dress, take pics and, probably, feed his sexual desire).  He is straight (he loves the female form and loves looking at pics of naked women as well as CDTGs). I don't believe that he is "open to the possibility of being more" and he is certainly not living as a woman or entertaining gender reassignment surgery.  I believe that he loves how he looks when dressed as femme (and he looks great, might I add) and it adds to his sexual arousal but he also enjoys being a man and being with me as a man.  

As for keeping HERself separate from him...I completely agree with you.  I think I scared him when I let him know how accepting and supportive I am of his femme side.  I've told him that I would love for us to explore this side of his sexuality and let us get kinky along the way.  We haven't.  And that bothers me because he would rather have sex chats and share pics with other CDTGs instead of letting me in on it or allowing us to see if it's something that could deepen our relationship.

Now, let me completely admit that, YES!!  I know this is shameful and that this lifestyle comes with a great deal of guilt and secrecy wrapped around it.  However, I'm the one who said "It's ok.  I love you and I want you to share this with me...just not with others in a sexual way [without me]."  Yet, he continues to find "like-minded people" online.  I've talked with other CDTGs in an attempt to better understand (which is why I'm talking to you) and the consensus is that I need to be patient.  That, in his mind, I shouldn't be accepting or supportive of this and that he's also just playing out his fantasy with others who don't know him or will judge him.  Yeah,  I get it, but it still HURTS and I'm still confused!!!  I mean, if you're sexting or doing webcam and you share info about your personal life (like what you do for a living, or give a pic of you as a man) then I feel that this is the beginning of developing a relationship, even though I know that these are kind of like ice breaker conversations.  Ugh.  I'm sorry, I've read what I typed and it seems like I'm babbling but I feel you need to have the detail even though it's going in circles.

So, yes, he has to be in that "certain" mood to chat with CDTGs or check his femme email or accounts.  That's where it feels like a split personality.  I have tried to communicate with him and his femme side.  I have tried to talk about it, but he says "it's just fantasy" and blows it off (i.e. walks away).  Just recently, I sent an email to his femme account telling him how much I love him and support him but feel like he's cheating on me with these sites and sexting with others.  Yes, he was very surprised that I knew his femme account ID.  That aside, as soon as he got that email, he was upset, came to me and said that that is "something he doesn't want to deal with right now", but he never answered any of my concerns.  I knew that if I continued pressing the issue, I would just push him farther away so I dropped the subject.  At least, with HIM I dropped it...it continues in MY heart and brain.  Again, which is why I'm looking for solace or answers, or both, from you and others who are open enough to help me.

Sincerely, I THINK he has a fetish and this has a sexual thrill for him.  I say that because recently I helped him get a wig he's been wanting for a long time.  Now he feels like he can go to a CD bar as passable.  Of course, he told me that he wants to be able to go with his wife (me) and have a few drinks while being with people like him.  Of course, this makes me nervous, because I would hate if he's going to start checking out other gurls and start flirting or build up the gumption to go on his own and experiment with the gurls he meets.  Will he do this?  Is that his intention, to transition into going out on his own?  I don't know and I hope not, but I can't control this.  He's always been faithful to me and we've been together for 3 years but ... crap.  I don't  know anymore.  A few years ago, I asked him if he wanted to be with a CDTG and he said "I don't know.  I might..." but that was also while he was questioning his sexuality.  I think he's more firm in the fact that he's not gay and loves me but there's this cloud of CDTG arousal hanging over his head.

Listen, I'm not proud of this, but I saw one of his chats where he said he would like his "first time to be very special".  And POW!!!  Did THAT hurt when I read that!!  But, I also know that when there's chatting involved, there's a lot of bullshit being said.  You know, like "I'd love if we got together when you come into my city" or "Yeah, I'd love to meet you someday, honey" or "I wanna do **this** to you"... but there's never any intention to actually go through with it.  

Wow.  That's a lot of background, isn't it?  It's also a lot of frustration and fear masked in love.  Clearly, I love him and I want us to work things so that our relationship is deepened and strengthened but it can't happen if he continues to keep "her" separate from us.

I know this is going to require more than a simple email and I hope you're up for the task.  I sincerely appreciate the help you've already extended and pray we can continue.  As you can see, I am pretty open and not judgmental.  I hope I can get the resolution I'm so desperately seeking.

Much in gratitude - 
Kim

Instead of responding via email, I decided to respond here.  Primarily so that other people can join this discussion and maybe help her out, but also as Kim pointed out, to show that people going through a situation like this are not alone.  And perhaps... just perhaps... if Kim's significant other is perusing his sites and comes across this, he can see how much Kim wants to share in that side of his life.

On to my response:

Kim,

The first thing that comes to mind as I read your response is how that first experience went.  You mentioned that you had girl on gurl sex, but that you wanted to try other things like using a strap on.  I'm assuming that you talked about it, but that your SO shut the conversation down.  And I see later that you mention that he was struggling with the thought that he may be gay, bi, or bicurious.  One thing that may have come up is a fear of the strap on.  Yes, you mention that he is turned on by Tgurls... but that attraction might be in him imagining that is what HE looks like.  So the thought of you using a strap on might have made him nervous or outright scared.

Now, you ask some direct questions.  "Why does CDing turn him on?"  That's a good question.  Sadly, I'm not sure I can give a good answer.  As I mentioned before, I've tried cross dressing (to the degree that I can), but it hasn't done much for me.  Certainly not enough for me to have a strong desire or need to continue.  Where I am drawn to the fantasy of being feminized, I'm not nearly as drawn to the fantasy of being feminine.  So I can't say why cross dressing turns him on.  But one thing you may want to do is focus less on the why.  Why are we attracted to the people that we are?  Why does one person prefer redheads over blondes.  Why does one person want to dress up in skirts and blouses while the next person prefers jeans and teeshirts?  You may never find out exactly why dressing up turns him on, because your significant other may not know himself.  This is actually where I specifically was hoping for some more help from the community.  If you could share with Kim WHY you enjoy cross dressing not only would she be gratefull, but I would as well!

"Why does he have to go onto CDTG sites?", "Why does he have to [sex] chat with other CDTGs or share pics?"  I think these both basically come down to the same question.  'Why does he join in and share with the CD/TG community, and not you?'. I think part of that is the very open and accepting community that we have.  I was really surprised by how accepting everybody was when I joined up and first spoke out at Rachel's Haven.   There wasn't a single person that asked why I was there.  They never asked what I wanted out of the community... they just supported me being part of it.  I'm not saying that you shouldn't ask these things of your significant other... but it may be comforting to him to simply be accepted and not have to explain everything.

You say that he recently 'purged' himself of everything.  That tells me that at least a part of your significant other thinks that this is wrong.  That he's still struggling with accepting this side of himself.  And not that you meant anything wrong by it, but by asking him why, you were making him justify it not only to you, but to himself as well.   I'm not sure if you read my recent post "Being Caitlyn" but I'm struggling with those same questions myself.  I have the luxury of doing this by myself.  Yes, I'm sharing it here, but I don't have someone I love, look me in the eye and ask 'why?'.  

I can tell you that being part of these communities... that chatting with my friends... helps me feel that there is nothing wrong with me.  It gives me a lot of comfort to just be accepted.

You say you believe he loves how he looks en femme, but that he also enjoys being a man and being with you as a man.  He may just need convincing that you can see him as both.  That even though you can share in his femme self, have fun and even have sex with him that way, that you can also still look at him as a man, and enjoy him as such.  Right now by having his sex chats and sharing that side of himself online, he get's to keep you fully to his male self.  And risking losing your love of him as a man may be very scary for him.

Patience is a fine virtue.   I think you SHOULD be patient.. but patience can't be everlasting.  Another fine virtue is fidelity.  I think that's incredibly important to any serious relationship.  Most people wouldn't accept their lover going online and having sexual chats with another person.  The fact that your SO is doing so while cross dressing and doing so with other similar people doesn't change that.

I think your SO has the world at his feet, and he doesn't even realize it.  Finding a woman that will accept this  type of 'hobby' or 'lifestyle' is rare.  Finding one that is not only accepting, but wants to be part of it is even more rare.  By all means, be patient.  Give him some time to realize just how good of a thing he has in you.  the hard part was sharing this side of himself and you accepting it.  Everything else should be easy in comparison.

You say you dropped the subject because you were afraid you would push him away by talking about it.   But I think you need to be open to the possibility that he doesn't know what he wants.  I think it's absolutely lovely what you are doing for him.  Just the fact that you are out here asking for advice shows how much you love him.  But that love needs to be a two way street.  It's wonderful that you love him so much, but you deserve that same type of love back.

I think if he truly loves you, then he should be able to talk to you about this even if it doesn't lead to direct answers.  Even fi its "something he doesn't want to deal with right now".

I'd love to answer all of your questions, but most of the things you ask can only come from him.   Does he really want to be with another cross dresser or a TGurl?  Only he can say.

I hope that some of that helped, and I hope that others that read this will chime in.  Above all else, I hope that you and your significant other can make this work.  All of us out here that are dreaming about a relationship with a loving woman that accepts this side of us want to know that it can work out!

Now it's up to all of the readers out there.  I'm sure Kim would like any help that you have to offer.  Even if you don't have all or any of the answers, she'd love to hear from you.