BF dropping hints: should I ask him?

[tasha_shalala]

Dear all,
I am new here, and I would like to introduce myself:
My name is Tasha. I am not yet officially a SO of a CDer...but I suspect I have the perspective of becoming one. This is the reason why I come here.

I have been in a long distance relationship with my partner for more than 3 years now. Things are going steady, but something always seems to be there to hold him back. In the first glance, he seems to be your typical commitment-phobic guy (40, once divorced), who demands a lot of personal space. But during our last few holidays together, I had a feeling that he had been dropping hints: he told me he wanted to try on some of my clothing; he would like to try a manicure and pedicure and make-up session. In some trips, he also bought a lot of feminine accessories...for himself.
In the beginning I took them as jokes, but eventually due to the frequency of these jokes, I realized it may be no joke at all. I have encouraged him lightheartedly. I jokingly suggested we went for a manicure/pedicure, he then only laughed nervously and said he'd be too shy.
Once he let me use his computer, and I saw on the website address, there were entries of transvestite websites.

He's someone very sensitive. That's why sometimes when he seemed to drop hints, I didn't want to poke further. He also has a great tendency to avoid conflict and confrontation. That's why I wonder if I never bring up the issue, will he ever come out to me? Will he ever be ready??? (Of course, provided if he really is a CDer)
And if I should bring it up, how?
I feel like walking on eggshell :-(

I have to say, I sometimes fail to grasp what all the fuss about telling your CDing to your partner. Because for me, it's the person I love. Yet not until these few weeks I have been doing my research on internet, do I realize what a torment it could be.
How should I go about with the situation now?
Any input? Or experience to share?

[Kathi Lake]

Tasha,

Telling the one you love about doing something that the world pretty much condemns can be one of the hardest things one of us will ever do. To a girl, it's no big deal as all throughout your life, you have been able to wear what you want with no problems. Like to wear guy's clothes? OK, so you're a tomboy - no big deal in the world's eyes. A guy that likes to dress as a woman? Sissy is probably the least offensive word for that group.

Keep on loving hi, but let him know clearly that you feel like you're walking on eggshells. Let him know that you want to support him, that you accept him, that you love him - no matter how he dresses.

Kathi

[luvgirlyclothes]

show intrest in the subject, show him you aprove of the lifestyle, and then maybe you buy him something small like panties and just leave them out for him
most of all good luck

[Leelou]

Based on all these hints he's dropped, I think you're probably right that he's a crossdresser. Especially since he's mentioned wanting to wear your clothes

You seem really sweet and supportive. He's very lucky. Yes, please talk to him about it. If you are truly supportive and OK with this part of him, I'm sure he'd love to know that.

[Raychel]

Welcome Tasha,

First of all, In my opinion he is definitly one of us. Coming out to your SO is by far one of the hardest thing that a guy can do in his life.

If you are sure in your mind that you can deal with having a boyfriend dressing in womens clothes, then by all means bring the subject up with him. Get it all out in the open just how you feel. It is in both of your best interest to get this out in the open as soon as possible.

Talk to him and be his friend first. If this is not something that you can dela with on a regular basis then let him know that also, and give him the space that he will need. This is not something that will ever go away. It can't be cured. It is part of him. Love him and have a happy life together.


Raychel

[Karren H]

I'd ask him!! If not maybe he would like to try it?

[DaisyG]

Hi, Tasha. Welcome aboard.

After only a short time here, you'll see we CDs represent a large diversity of personalities, needs and experiences. I'm confident you will find your way to some answers here.

I understand how a CD may be reluctant to come out, even to one he loves deeply. Such reluctance may arise from a number of factors.

He may be a shy person.

Even at his age, he may not really have become able to articulate to himself just who he is, as a CD. If so, it's going to be doubly hard for him to explain to others. I know this situation well, not being sure who I was, for DECADES. Over 40 years ago I blew a chance to share my life with a super GG because I wasn't emotionally able to talk to her about my CDing, yet I would not let myself commit to her without her knowing. Now as a senior citizen, I finally have a handle on it and can talk about myself.

There are many SOs who, unlike yourself, are 100% hostile to CD and are totally non-accepting. Sometimes a CD marries this type but fails to dosclose his CD, then years later she find out. If that was your guy's fate, and he lived thru a serious emotional train wreck , it's no wonder he's not talking much.

These are only a few reasons why he's holding back.

You sound like a very loving and patient soul, willing to invest a lot of time, energy and emotional capital in your relationship. You are right in not forcing the issue. Without being confrontational, you need to gently guide and coax him into talking about this part of himself. The more you can learn about CDs and their accepting SOs, the better equipped you may become to do this. It may take awhile, but if you succeed, I sense you and your CD are on the way to some wonderfully happy times.

My best wished to you both. HUGS!

Daisy

[Holly]

Hi Tasha and . Any chance CDing was involved in the break-up of his last relationship? That could explain a lot.

How about trying this... Invite him over and have a nice dinner in planned. Have some soft music playing and a bottle of wine handy. Enjoy some conversation and then send him into the bedroom to "change into something more comfortable." On the bed you have placed some lingerie for for him and a pretty robe. If he comes out asking what the heck is going on, tell him you remember he once asked if he could try on some of your clothes and that you thought tonight would be a good time. If he is open to the idea, then great... you have an opening to engage in further conversation. If he is not open to the thought, the serve dinner and enjoy an intimate evening together. You've planted a seed. I suspect before the evening is over, the subject may come up again. . Oh, did I mention wine?

[Alice B]

While none of us can give you a concrete answer it seems as if he is a cross dresser. if you are OK with this then I would tell him so. Let him know that you love him for who he is and that being a cross dresser is OK. Then force him to openly discuss the topic and arrive at acceptable agreeable standards. It sounds as if you really care about him and that dressing is OK. Where you go with this is up to the two of you, but open communication is very important.

[tasha_shalala]

For those of you who have replied:
I have never been on a forum before. I didn't expect such quick responses, and o so warm and insightful!
THANK YOU ALL!!!
I am sitting here with tears in my eyes :"-)...I feel less alone...

[az_azeel]

For those of you who have replied:
I have never been on a forum before. I didn't expect such quick responses, and o so warm and insightful!
THANK YOU ALL!!!
I am sitting here with tears in my eyes :"-)...I feel less alone...

Dont feel sad.. one thing about this forum is your not alone.. i think holly summed up what i was about to say.. talk about great minds etc... by the way pleased to meet you...

[FireflyGG]

I'd ask him!! If not maybe he would like to try it?

I agree with Karen, but I'm a pretty blunt person so my approach may not work for everyone. Since you've done your research and it's something you're feeling comfortable with right now, I'd just ask him. I'd say if he's not already into it in private, he's pretty damn curious. It could be fun for you guess to explore the possibilities together! Keep us posted. I'm curious about Chapter 2 of the story.

My partner ended up dropping some hints so by the time he told me, I told him I already had him figured out. In the end though, it's been an awesome addition to our relationship. If you ever need a virtual ear, drop me a line.

Good luck and yay for you for being so supportive!! I can't even begin to tell you the amount of relief that is in Melissa's voice when she tells me how thankful she is that I'm so open and accepting of all sides of her.

[RADER]

tasha_shalala
A big warm welcome; You came to the rite place.
There is a lot good ideas on the post above, but one idea might add to
"break the ice". Get him a cute baby doll night gown, and the next time
the two of you are alone, suprise him, and tell him that you want him
to model it for you. Then if jumps at it, that just might anwser some of
your questions; if not opening the door to more questions. Go slow, Talk,
Talk, And Listen. Rader

[Andy66]

It sounds like you're lucky to have found a sweet, sensitive guy. The fact that he is dropping hints tells me he is shy or embarrassed, but doesn't want to be a liar. That's so important, and all too rare in this world.

Just make sure he knows he can be himself with you. At the same time, you have a chance to really be yourself too because great communication should go both ways. Good luck.

[sheidelmeidel]

I respectfully disagree with Holly and agree with Kathi Lake, who got it perfect IMO. Taking the initiative with him by putting out clothes, etc could do more harm than good. I think it would be unwise to do such a thing until you know a lot more about what's really going on with him as far as CD'ing, past relationships and so forth. You feel like you're walking on eggshells because you are - the only way to make it across is slowly and carefully.

[docrobbysherry]

Sex is a reason MANY CDs dress!

The guilt and shame some get from dressing, would make it VERY difficult to discuss with someone they're involved with, and that they care about!

There is also, the "gay/bi", aspect of CDing. When I started dressing, I thot that I mite be GAY or BI!

Turns out I'm not, but some of us r!

[MAJESTYK]

Tasha, thats one of the things you'll find out about us, we are quick , they're are a bunch of us and we will always be here if either one of you needs us for anything! We think of everyone as family of sorts!
Now, on to the question, you have to go slow or he might just go further away from the subject. Just keep mentioning it at the right times. Like when he wants to dress etc.. It is something that , even though we find someone who is ok with it, we can be scared to bring forward. My wife kind of suspected me and then just sort of brought it all out one day when we moved by bring some dresses she had to the new house and Told me she thought I might like to wear them. Just be patient and it will happen.
Now remember, we're here for ya both!

[trannie T]

Buy him some nice panties for Christmas.

[FireflyGG]

Buy him some nice panties for Christmas.

Yay for new panties!!!

Crap. was that my outside voice?

*goes back to drinking her wine*

[giuseppina]

Tasha,

Telling the one you love about doing something that the world pretty much condemns can be one of the hardest things one of us will ever do. To a girl, it's no big deal as all throughout your life, you have been able to wear what you want with no problems. Like to wear guy's clothes? OK, so you're a tomboy - no big deal in the world's eyes. A guy that likes to dress as a woman? Sissy is probably the least offensive word for that group.

Keep on loving hi, but let him know clearly that you feel like you're walking on eggshells. Let him know that you want to support him, that you accept him, that you love him - no matter how he dresses.

Kathi

I like this approach. If he's been traumatised by a previous relationship, leaving things around may be too much and drive him away.

While I've never been in a romantic relationship, I have been in a situation similar to the situation I describe. The issue was that I'd seen so much visceral and unhealthy conflict that I was completely closed to the idea of a relationship. There was one person, a GF, who was after me that seemed nice (there were others), but the conflict I'd seen left me too traumatised to respond. CDing was not on my radar at that time.

He may well be walking on eggshells as well.

[sissystephanie]

There are lots of very good responses her, but I think our unofficial "Mom," Holly has given the best idea! It was mentioned that he "wanted to try on some of your clothes." so give him the opportunity! That might be the opening he was hoping for. Because I believe he has been searching for an opening to tell you, judging from the things you have said he has done or said.

If he does put some panties on, let him know that you love him very much no matter what he is wearing since you know he will be your man underneath! I told my late wife before we married, and that is what she said to me, that I would still be her man. She said that to me over 54 years ago, and we had almost 50 years together before cancer took her from me! She was totally supportive all the time!

Try Holly's idea, and let us know how it works!! Good Luck, and Bless You for being so loving!

[suchacutie]

Hi and welcome!

You mention that he's dropping hints. You can do that too! It seems that you have ample entre into this world from his actions. I'm thinking about asking him if he likes your outfit (whatever it is) and see how knowledgable he is! Comment favorably. Engage him in conversation about your clothes and makeup as much as you can. If you see an entre to asking him which of your clothes he might like to wear or that you think he'd look terrific in some piece of clothing, etc. Talking about makeup could smoothly lead you to trying some eye shadow on him so you can see how it might look on you. If you are of similar size you can try that same thing with clothes or shoes

I will bet that he's just as concerned as you are, and will be incredibly receptive to little bits of conversation here and there, expanding them as such conversations normally happen.

We all wish you very well and know that when you both get by this small bump in the road that life has such a bright view!

tina

[silkenhose]

yep, flat out next time u are with him say hey, do you like to dress up? or would you like to dress up?

one poster said that alot of us worry about the SO thinking we are gay, get it out of the way, ask him....as he could be but most likley not

silk

[Miranda09]

I'd say go ahead and ask him. If you ask in such a way that you're not making fun, critisizing, or demeaning him, that you really do want to understand him, I think he may just open up to you. If you approach it right, this may open up a whole new aspect of your relationship that you can alot of fun with!! Good luck sweetie..

[DaphneGrey]

I would like to add my two cents. You sound wonderful and I think your boyfriend is very lucky. Perhaps I can shed some light on how difficult it is to disclose at least in the begining. When I finally mustered up the courage to tell my wife (then my girlfriend) I got physically sick! I was absolutely petrified with fear. To give you a little perspective I had just finished a tour in the USMC. I was and remain today a high speed adrenalin junky. So in masculine life I appeared quite tough and rather confident.

Telling the woman I love was the most difficult thing I have ever done, probably because I wasn't ready to answer questions I did not have answers to. It took a long time to figure out where all of this was going and what it means. Then there is the social stigma to come to terms with. This gender thing is not something I would wish on anyone. I am not complaining mind you as I have learned that it is part of who I am and I make the best of it. I just want you to understand that there is a lot of baggage that goes along with it. We all have to work through it and we have all struggled with fear and doubt. No doubt in my mind your SO is struggling with some of those same issues.

My thoughts on getting him to open up are simple. Talk to him, tell him exactly how you feel about him holding back. Tell him you think it's sweet that he likes girl things (if indeed you do). Tell him you are willing to experiment with it when and if he is comfortable. Tell him you don't want there to be secrets between the two of you. Give a green light and perhaps a gentle nudge in that direction. I do think it is important to let him drive so to speak. He has to feel comfortable talking about this stuff and if he is not ready, pushing to hard will cause him to clam up. I don't think you want to risk that.

With all respect to other forum members I would like to say that the lingerie gift Ideas are not a good Idea. Please don't missinderstand I would love it someone did that for me. But I have been out of the closet for quite sometime. As sweet and romantic as it might be for some. Your boyfriend might not be ready for it.

Also I don't want you to forget about you in all of this. It can be a lot of fun and it sounds like you guys are great for each other. If your relationship is heading down this road you will both face some challenges and you will both have so e unique needs and desires, and even some boundries.

This is all much to think about, and I hope it helps. I would like to offer you any help I can and your boyfriend as well. You can PM me any time and I will do my best to help.

Best Wishes
Daphne