Inadvertently, had a third conversation with the fiancee.

[Julie1123]

Kind of out of the blue, she asked me if I ever worried about losing her. I told her for the most part no. That I didn't think she would ever cheat on me, so there was no issue there for me, and I wouldn't ever cheat on her, because no sexual fantasy is worth losing her over. She liked that.

Then I chose to break the DADT and tell her the only thing that I sometimes worried about was I might lose her because of the crossdressing. She reiterated that the only way that might happen is if it became a necessity for me to go out dressed. I told her that I did sometimes think about it but it was more along the lines of something fun to do rather than something I needed to feel whole. She nodded and said that she knows there are no guarantees things won't change but she'll probably need reassurances again closer to the wedding. I told her that I thought it was highly unlikely things would change and reminded her that I've been doing this for about four years now and I'm pretty comfortable where things are at as far as what I want to do. I also mentioned that I didn't mind giving reassurances but because of the DADT she'll need to bring it up. I told her that the only thing that I had really been hoping would change someday would be our ability to talk about it more openly with each other. She tensed up a bit there and so I followed up with, there's definitely no pressure on her to change and I don't ever expect it to change, but I do hope it does. That I loved her sense of fashion and wished we could share in it more. That eased her a bit although it came out kind of awkward on my part.

She then asked about how it would work if we have kids. We've always been kind of on the fence about whether we would or not. I said that was kind of a tough one but that I was leaning more towards out of sight of the kids until they are older. That we would probably have to work out some time for me to be able to dress when the kids were out of the house. She was agreeable to that. I asked how she would feel if we had a kid that was a crossdresser and she said she would support them whole heatedly and not want to suppress them.

I finished up the conversation by telling her that I really appreciated how she was handling this. She said that she didn't really know how to respond to that. I said there really wasn't anything that needed to be said to it, just that a lot of couples break up because of it, and that I wanted her to know I appreciated her. Overall, I thought it was a good conversation and there was no period of coldness after the conversation so that was great.

Today, I've shaved my legs and painted my toenails. She's only ever experienced my legs being shaved after the hair had been growing back for awhile on one of my visits when we were living in different states and she's never seen me with my toenails painted. In our last conversation she said she probably wouldn't be bothered by the shaved legs but wasn't sure whether or not the painted toenails would bother her. I tend to wear socks almost always so they won't be too hard to keep out of sight for the most part. The only time she might see them is if I'm showering, getting into bed, or if we are getting intimate. Wearing socks during sex just feels funny. Hopefully if we do get intimate the painted nails won't be too bad of a turnoff for her. Fingers crossed.

[Beverley Sims]

Treat her kindly and Ihope you continue in a good relationship.

Wearing socks might feel funny....

Just don;t wear your boots.... :-)

[Julie1123]

Haha :D good point, Beverley.

[daviolin]

Good for you Julie. At least your telling her before the marriage. I waited 30 years into our marriage. That was a hassle. Just stay true and trustworthy. Daviolin

[Julie1123]

Thanks, daviolin. Her and I had been together about 8 years before my desire to crossdress started to manifest. I told her pretty shortly after I figured out that it was something I enjoy and wanted to continue to do.

[Stephanie47]

I hope you and your future wife can be really open about expectation on cross dressing. I'm throwing out a general question. If a man is in a DADT relationship, such as myself, what does that exactly mean as far as boundaries. How can one call it DADT when you choose to paint your toenails and then hide them by wearing socks all the time? And, also shaving legs. I've seen many posts of what I call body modifications (shaving legs and body, painting nails, shaping/thinning eyebrows) but still calling DADT because there is no discussion. It just seems wearing socks while making love and having shaved legs would be a reminder for her that you're a cross dresser. I'm just curious, not being judgemental.

[Dana44]

Do know that men do paint there nails in parts of this country and they are masculine about it. I paint my toe nails and well they are out of site during the encounter unless there is a foot fetish. I would not worry about that and you are taking care of your feet and making them pretty. It is not weird to do that. In fact when I go to a new nail place they always ask to paint my toe nails after a pedi. When I went for a whole week they painted my toenails and my finger nails a very pretty bronze color and at a gas station a man asked me to look at them and asked where I got that color. Said he was looking for something like that. Look it up it not weird to paint your nails. But I only keep my toenails painted.

[Julie1123]

Hi Stephanie. It really depends on the couple. My fiancee and I have two things in place. The DADT which for us covers me not talking about it unless she asks or if its really important that it is brought up to avoid other issues. We also have an out of sight out of mind understanding. Which from her point of view, as long as she's not constantly reminded of it she can tolerate it. She knows where my clothes are kept but since they are separate from her clothes and my guy clothes she can choose to avoid them. As for the shaved legs and the painted nails, these are things that we discussed in the previous conversation we had. I brought up that I enjoy both those things but they would be hard for me to keep them out of sight all the time and she was ok with that, or not outright opposed as long as they were mostly hidden. We also have an agreement that if anything does start to bother her she'll bring it up so that we can deal with it. Luckily we have been able to sit down and discuss everything I want and don't want to do and set clear boundaries so that we are both comfortable. While the conversations are very uncomfortable for her because I can understand its not something she ever thought she would have to deal with and is not completely okay with, I think its better for her and for us that she knows everything I do in general.

To speak in general, I guess, there is no one set of boundaries that applies to all DADT relationships. Its up to the couple to communicate as best they can. Be honest with each other and respectful of the other.

[Amy Lynn3]

Julie, on a lighter note about the painted toe nails and them covered with socks..... just don't use combat boots to cover them in bed either.:D

[Julie1123]

Dana, she's not much of a girly girl so the fact that I'm making them pretty wouldn't matter much. :) Sounds like you've had some great experiences though. One day I hope to be able to go get a pedi.

Amy :D so true, so true.

[Amy Lynn3]

Julie, I get pedicures and manicures all the time. I see more men in the shops than I do women. The Asian women there do a good job and they keep the cost low. About every 3 months I get the best manicure and pedicure they offer, plus a back rub for a total of 70 bucks. Well worth it.

Sometimes I allow clear polish on my finger nails and I paint my own toe nails, for special occasions.

[Julie1123]

That's good to know! Thanks! :)

[JamieG]

It is good that the two of you are talking a bit. However, the part about shaved legs and painted nails worries me a little. Does she know that you've done this? If she accidentally discovers it, will she think you have broken your end of the DADT arrangement? The first time I shaved my legs, I did it without saying anything to my wife. About a week later, after I had gotten bristly, we were in bed together, she felt my legs, and immediately we had a huge fight about it. This is not the sort of thing you want to surprise her with, given the fragile truce you seem to be in right now.

[Jenniferathome]

...I asked how she would feel if we had a kid that was a crossdresser and she said she would support them whole heatedly and not want to suppress them. ....

Quite the ironic statement for a DADT relationship. THAT'S worth a conversation!

[Jane G]

Had to look up DADT. LoL turns out I my wife and I agreed similar terms around 30 years ago. She is far more comfortable about cross dressing now.:battingeyelashes:

[Julie1123]

Jamie, we have discussed it in a prior conversation. I told her there were a few things that I like doing that I could keep mostly out of sight but couldn't guarantee 100%. The main three being, shaving my armpits, legs, and painting my toenails. The shaving she said she wouldn't really mind but she wasn't sure about the toenails. I've had my armpits shaved since that conversation a few weeks ago without any issues. Wanted to wait awhile until I did the legs and nails so not to dump everything on at once. Hopefully, it will go as smoothly as the armpits. :D

Absolutely, Jennifer. I think her main aversion to my crossdressing is one of embarrassment she would feel if people knew that she was with a crossdresser. She's acknowledged that she's a bit hypocritical on the subject as she always expresses disgust with a lot of the recent anti-trans news stories. I'm hoping that with time she'll be able to allow herself to open up about it and at least get rid of the DADT. Not holding my breath though.

Edit: hahaha Jane, that's wonderful. :)

[Tina_gm]

The embarrassment can be a factor if she has several friends or family members who she knows would not take it well. In my case, unfortunately I live in an area that is not at all accepting for the most part. Also, we have several friends and a couple of family members who would not be at all good with it.

[Samantha_Marie]

That sounds like a lot of conversations with my wife. It's good that you're not waiting.

[Julie1123]

gendermutt, I agree completely.

MelanieAnne, valid point. It's a tough one because on one hand you don't want to perpetuate the idea that it is something that needs to be hidden from view but on the other hand it can be tough for kids to deal with other kids and people who don't understand it. Also, kids don't tend to have a filter which would prove problematic to keeping it just something my SO and I know about. I said leaning towards in the conversation because at the time I hadn't put a whole lot of thought into the particulars and was just going more on a feeling.

Samantha, absolutely. Better to have established boundaries than risk it being something that drives us apart.

[phili]

Since this sounds so much like my conversations with my wife I'll add my two cents after 30 years of marriage, threatened by discussions of crossdressing. I'm of the opinion now that the marriage vow- basic contract to love and cherish, have and hold, and support and protect each other in sickness and in health, until death, describes the optimal marriage relationship, and it is founded on a fundamental desire to be with each other because you admire and respect each other, and delight in each other.

The drive to couple is really strong and tends to encourage hopeful compromises, but they are very weak forces, and they create an unstable foundation. My wife did marry me despite being told that crossdressing was part of my psyche, but today says she would not have married me knowing what it feels like more clearly. Since we are committed, it just makes for daily discomfort, which is bad enough that I wouldn't wish it on anyone. There are lots of reasons why couples can develop distance, and it really isn't a good situation. I'm really hoping we can work through this somehow, and my recommendation is to make a committment about this to each other that you know you can keep. She is basically telling you that the emotional storms are manageable if you keep them to a minimum, and you want to be with her, so you agree, but I think you are saying, naturally, that you don't want to feel like a pariah who is being hidden and tolerated, want to be proud of who you are and for your kids to think so too. I didn't crossdress while our daughter was growing up, for all the obvious reasons, and although she says she is ok with it and a modern woman who has been around, she sees it as my problem,and while being kind, is not really supportive in the way one would like- hey dad, go put on your dress!

So I would try to go deeper with your fiancee and say, really, we have to get to a place where I am not hiding myself from you. We are proposing to be life partners, and I understand your emotional framework right now doesn't encompass me sharing the feminine world and still feeling to you like your husband. Crossdressing is a means of trying to manage the deep part of my identity, and if we are marrying, that is too important to treat like a weird hobby.

Loving each other as ourselves is the right basis for all relationships, and it has to be central for this all to work out, and the best news is that it works better than the alternatives. It requires really finding mutuality, and is a great test of the fundamental personal commitment needed to be married happily!

[BillieAnneJean]

I find it interesting that she says she would wholeheartedly support a child that CDs.
I find it interesting that she seems to be supportive to some level of your CDing.
Somewhat VS wholeheartedly.
Not criticizing. Just observing.
I can understand her buying in to your relationship as she sees how it fits her ideas of what that relationship should be.

[sometimes_miss]

As weird as it might sound after the fact, you can incorporate stuff into you male life that TO YOU is part of your CD life. Take up swimming as your exercise. Start making up timing your laps. Now you can shave your body to 'increase your speed'. Do it every time before going for your 'competitive' laps so it will appear to be the legit reason. Bingo. now you're shaved all the time. Oh yeah, and you're in great shape, too. For me, I just love to swim, so it became a convenient excuse. It's gotten so commonly known that even my friends are making excuses for me; I overheard one talking to someone else at a party, one guy saying, 'Is he shaving himself? He has no hair on his arms or legs.'. Then my buddy says 'Yeah, he thinks it makes him swim faster. I think he's nuts'. The guy who made the first comment just shrugged and it seemed he didn't think any more of it, though I can't be sure for certain. What I do know, is that it's more acceptable to be nuts over some sports activity than it is to be a crossdresser. So that's how I roll. And the best thing? I always used to make excuses to myself for not going swimming. Now I have a good reason, and it's fun, too. It makes me happier in my day to day life.

Want to do your eyebrows? Embrace metrosexual fashion. Like make up? Amatuer theater. Nail polish residue on your nails? Take up building models with fancy colors, 'accidently' get bits of paint on your hands and nails on occasion (and don't wash it all off, leave just a clue), and no one will notice the occasional light blue, orange, pale green on the edges of your cuticles (though another way is to just get your skills right and use a well applied basecoat that will keep the topcoat from remaining after you remove it all).

Like to underdress stockings? I like to play basketball. I have varicose veins. So one warm day, I went down to the corner courts with my really thick stockings for the varicose veins on, an ace bandage wrapped around one knee, knee socks with the stripe colors of the local NBA team on them, and my favorite Willis Reed #19 jersey. Spent the whole afternoon there, only one guy asked about the stockings, I guess word got around. Those stockings come in flesh color as well as white. Sometimes i would only wear one stocking but always wear the socks. It establishes a pattern of behavior that has nothing to do with crossdressing to the outside world.
I'm sure there are lots of other ideas.

[Tina_gm]

I know the most common reply on here in situations of DADT is that WE need to go deeper with our partners and have more convos/communication. Well, yes and no. Of course communication and lots of it is not ever truly a bad thing.... but for some partners, they really are better off just dealing with it as little as possible. Which means not a lot of conversing about the subject. Not a lot of time thinking about something they cannot get their head around, and any attempts to do so usually end up going real bad. It is not the perfect solution overall, but sometimes given the circumstances, the best one. I am not saying this has to be yours, but maybe a set of boundaries if you will, which I don't really like the word, but it is what it is, then just leave it the heck alone, until one day if it ever comes, which may or may not happen, she feels more comfortable talking about it.

[Leslie Langford]

Julie, I hate to be a "Debbie Downer" here, but in the course of reading through your OP I was reminded of the infamous Chinese Water Torture technique...drip!...drip!...drip!... or perhaps more precisely, the Death of 1000 Cuts.

And hearing of the contortions that you and your fiancée seem to be going through which are interspersed with the little bits of give-and-take here and there along with the tentative feelers of what might - or might not - be acceptable in the future...frankly, it makes my head hurt. Sorry to be so blunt, but this all seems so wishy-washy yet well-intentioned, but it also studiously tries to avoid the real elephant in the room - your wife-to-be is fundamentally uncomfortable with the thought of your crossdressing and that will NEVER change, yet both of you are twisting yourselves into pretzels in the naïve hope that you can somehow make this work.

Look at the many posts here from the married veterans of the DADT wars (myself included - 45 years, and counting), and you will see that by and large, it is not a pretty picture. If anything, it often leads to unfulfilling and unhappy lives on the part of both spouses who desperately try to justify staying together on the premise that the other good aspects of their marriages outweigh this crossdressing ten-ton weight on their respective shoulders...and besides, they already have too much invested in their relationship (financial, a joint home, children, respective career tracks, retirement plans etc.) which makes splitting up at this point an even more daunting proposition. After all, a devil that you know is better than a devil that you don't know, right?

People like myself who find themselves trapped in a DADT situation like this are the authors of their own misfortune (often despite the best of intentions), and the more "mature" among us who didn't have the wealth of resources available back then that the people of your generation now do often got married in the mistaken - albeit sincere - belief that this whole crossdressing thing was a passing fancy and that marriage and a regular sex life would "cure" us - NOT!, as many of us belatedly discovered, much to our chagrin. And thus, we found ourselves trapped in DADT H*ll.

You, Julie, are not in that situation - yet. I feel for you and your fiancée - I truly do...you are both really, really trying hard to make this whole crossdressing thing work, but there are just too many red flags here. Too many uncertainties, too many leaps of faith that future changes in boundaries can somehow be accommodated, but having no real basis in fact beyond faint hope and the expectation that you will somehow be able to "wing it" once these new developments - or urges - begin to rear their ugly heads. Remember, too, the old adage that men marry women in the hope that they will never change, whereas women marry men in the expectation that they can mold them into their own image and exorcise all those "bad" habits and personality traits that they brought with them into the marriage. It won't look too promising for Julie if that's the case...and we all know how well purging and supressing our need to crossdress works...

Not just that - when young'uns start to come into picture, it's going to be whole new ballgame. You're loving, supportive (?) wife will quickly morph into Mama Bear who puts her cubs' well-being ahead of everything else, and you will be driven back into the closet so deeply it will feel as if you fell into a Black Hole.

So my advice to you, Julie, is to take a good hard look at what you are about to get yourself (and your fiancée) into before you both commit to a lifetime of potential misery. The road to H*ll is paved with good intentions as someone once wisely observed, but love does NOT conquer all despite what the romantics might claim (a 50%+ divorce rate attests to that). Those of us who agreed to DADT after the fact have to live with that choice, but you still have the option to back out.

What troubles me in particular in your OP is the fact that you are willing to compromise (surrender?) on so many points, whereas your fiancée appears to hold all the cards when it comes to defining the nature and dynamics of your future relationship. This will lead to a very asymmetric power dynamic between the two of you, and flies in the face of conventional wisdom that dictates that marriage must be an equal partnership based on ongoing dialog, negotiation, and compromise.

When you start off by conceding that only your future wife will have the right bring up any new discussions surrounding your crossdressing - including even referencing the existing DADT arrangement - that tells me that you have already given away the farm (not to mention your dangly bits) in advance of formalizing your relationship through marriage. Be afraid, be very afraid...

[Eva Bella]

There's a lot of advice here already, so I'll keep my imput brief. I was in a similar situation to you and just came out to my SO - successfully - a few weeks ago. A few things that I can advise:

1) I've come to know two types of straight men who do this. There's guys who get a sexual kick out of the experience and do it in the same way that they might do BDSM. And there's guys who do it to indulge a feminine side that lives within them. I'm in the second camp, as are most people here. I think that you are too. That's nature talking, and we can count ourselves as transgender. I've accepted and embraced this.

If you feel the same way, tell her. She needs to recognize that this is a part of you. And she may find it less threatening than some strange, imagined sexual kink. My SO thought the worst when I told her, and relaxed when she saw pics of me and my "girlfriends" - which look very much like pics of her and her girlfriends. She was able to accept it then, and she actually enjoys it now.

2) Go to a relationship counselor. You need one, and you need one quickly. I don't share the same doom & gloom outlook that others do - I think that you can absolutely work it out. But you need help to do that and there's nothing wrong or shameful about that. It will be money and time well spent and I think that you have a very good chance of a resolution.

3) If she does end up accepting, be sure to keep her first in your eye and balance out your girl time with a strong, thoughtful male side. You want her to feel that she's gaining a part time girlfriend, not losing the man that she loves.

[Julie1123]

Hi Leslie, first off let me say, I'm not offended by your bluntness. I love a good straight forward viewpoint. Before I can respond though, I do need to ask you for some clarifications. Can you please explain further about what exactly you see as wishy washy in my situation, what red flags you see, and how the specific compromises we've made are unbalanced?

[Nikkilovesdresses]

Wow Julie, I can't say strongly enough how much I think you've done the wisest thing in being totally honest with her. It doesn't mean there won't be bumps in the road ahead, but the important thing is that you haven't deceived her in any way. It's good that she sees the toenails and shaved legs, because if she thinks she can't handle that, you need to face it before the marriage and either come to terms with such habits or part. I'd recommend seeing a therapist familiar with the subject together and talking it through with them, because the DADT indicates she may be kidding herself a little that she can deal with Julie's presence in her life. OK she may lighten up with time, but equally she may go the opposite way.


For most women, marriage is a goal. It's all about the ring, the dress, the reception, the guest list, etc. Pretty much anything you tell them will be disregarded, and they will deal with it later, after the wedding. And most women think they can change a guy after they are married.

Generalisations or what! Perhaps these things may be true for some young first-time brides, but I didn't marry till I was 43 and my wife 47, and for us it followed about 4 years of living together. We married for love, and because it made it easier for her to live in Europe (she's American). We had no secrets from each other, we married without a church ceremony or even any guests, and our efforts to change each other are minimal. We have a mostly DADT about the CDing, but she knew from the get-go that I wear women's panties daily and occasionally at night and has never once objected, after 13 years together. I only dress rarely, but she's seen pics of me dressed and didn't run for the hills.

Keep being honest - it's really all you can do.

[Julie1123]

Yeah. We've been together for almost 12 years now. Just haven't gotten around to getting married because we both see it as a celebration of our commitment to each other and not the thing that causes the commitment. We were both in intensive education and so wanted to wait until after we were done with that and settled so that we could have the celebration we want.

[Leslie Langford]

Julie, here's where I'm coming from:


...Then I chose to break the DADT and tell her the only thing that I sometimes worried about was I might lose her because of the crossdressing. She reiterated that the only way that might happen is if it became a necessity for me to go out dressed. I told her that I did sometimes think about it but it was more along the lines of something fun to do rather than something I needed to feel whole. She nodded and said that she knows there are no guarantees things won't change but she'll probably need reassurances again closer to the wedding...

YOU were the supplicant in this exchange. YOU had to "break" DADT. YOU were more or less asking permission to go out in public en femme - maybe - if the urge ever hit you. Your fiancée replied in a similar non-committal, wishy-washy, passive-aggressive manner. No ground was gained here - she is still the puppet-master, pulling the strings in terms of defining existing - and possibly new - boundaries.

... I also mentioned that I didn't mind giving reassurances but because of the DADT she'll need to bring it up. I told her that the only thing that I had really been hoping would change someday would be our ability to talk about it more openly with each other. She tensed up a bit there and so I followed up with, there's definitely no pressure on her to change and I don't ever expect it to change, but I do hope it does...

Uh huh. Remind us again who's in charge here...?

...She then asked about how it would work if we have kids. We've always been kind of on the fence about whether we would or not...

Why does this statement not surprise me? Just one more example of indecision on both of your parts and a propensity to tip-toe around the difficult questions for fear of rocking the boat and perhaps upsetting the (more or less) existing comfortable status quo.

...I asked how she would feel if we had a kid that was a crossdresser and she said she would support them whole heatedly and not want to suppress them...

I'm with jenniferathome on this one. Say what??? I don't necessarily see hypocrisy or a double standard here, though. I see a potential Mama Bear talking here and being willing to do or accept anything to protect her cubs and support them - no matter what. Sorry, (future?) Dad, your needs/wants will always take a back seat should it come to a choice here. You've provided your sperm, you've done your part to sustain the gene pool, and your job is essentially complete. You can step aside now - Mama Bear will take over from here on in and decide how the child will be raised and what it will - or will not - be exposed to.

...I finished up the conversation by telling her that I really appreciated how she was handling this. She said that she didn't really know how to respond to that. I said there really wasn't anything that needed to be said to it, just that a lot of couples break up because of it, and that I wanted her to know I appreciated her. Overall, I thought it was a good conversation and there was no period of coldness after the conversation so that was great...

More supplication and profound gratitude that your fiancée "allowed" you to express your innermost feelings rather than treating you like pond scum - and potentially ripping you a new one - for admitting that you were unequivocally transgender and had these "bizarre" needs that will never go away and might possibly even evolve in other directions over time. Lucky you that there was no period of coldness afterwards, either..

Just curious, Julie...in the course off this conversation with your fiancée, did you by any chance remind HER of all the positive things that YOU have done for HER in the course of your relationship as well as the support YOU provided for HER particular needs, some of which you might not be totally on board with either? That maybe YOU have brought sufficient value to the relationship that more than makes up for the "burden" that your crossdressing has placed on HER? That despite your presumed faults, she is d*mned lucky to have you, just as you are lucky to have her?

As I said in my earlier post, marriage is a continuous series of negotiations and compromises. I'm not seeing a whole lot of acceptance (or even tolerance) for your crossdressing on the part of you fiancée here. What I am seeing, though, is a collection of meek requests which almost amount to begging on your part for her to put up with your quirks, and I'm not sure what exactly you're getting back in return beyond the continued pleasure(?) of her company. Is the sex with her really that spectacular that all other considerations which normally form part of a marriage pale by comparison?

Are you really prepared to settle for such an uncertain - and possibly soul-destroying - future once you commit to marriage?