Having The Talk (tm)

So I've been here for a bit, contributed to discussions here and there (hopefully in a positive way), and in general come to enjoy my time here a lot.

So now it's my turn to ask a question, and perhaps get a little wisdom from the girls here (genetic and not-so-genetic welcome to reply:D)

I've only recently started to dress again, after about a 30 year gap. To make a long story short, I dressed a lot when I was young (started at 14). I came to really enjoy it, I loved the feelings I got (sexual and non-sexual), and would have probably continued on into adulthood. I slowed down to a complete stop after a horrible incident where I was caught by my father wearing mom's clothes. Without going into details, suffice to say that the shame and guilt piled on for days afterwards were horrible, and on top of that the physical discipline just made it all worse. Over the next few years, I furtively bought panties (ostensibly on an errand for my mom) from time to time. Occasionally wore them, but just as often tossed them in the trash without even opening the package. Eventually, I stopped completely, and never thought about it much again.

Recently, I began exploring bisexuality. I had always been curious about it growing up, and had a few furtive encounters (like 4-5 in 30 years). For some reason, those desires resurfaced recently in my life. Mid-life crisis running a little late? Sudden brain chemistry shift? Heck if I know. I started having erotic dreams of sex with a guy. Now I've had erotic dreams before, but rarely, and from what I remember of them, they were always hetero in nature.

I talked this over with my wife. We've had a polyamorous marriage for quite a while, so I've had a few relationships outside of my marriage, always with her knowledge and awareness. I've never cheated on my wife, in the entire 10 years we've been together. So I told her about the dreams, and the new-found desires. She agreed that it might be a good idea to experiment (safely, of course), and see if it was something I wanted to pursue.

So, I did. I went to a local bar that is gay and bi friendly, and met a very nice crossdresser. She and I talked for a very long time, got to know each other some, and she invited me home with her. I went, and after an initial sexual encounter, we were talking in her bed. She said flat out that she'd love to dress me up and have sex again. This took me aback somewhat, but the idea was rather appealing after all those years. Now I'm not saying that suddenly, all those repressed memories burst forth or anything as dramatic as that. What did happen is that it reminded me of how good it felt! The next morning, we said a very nice good bye and I went home.

At the time, all my wife wanted to know was had I had an encounter and did I enjoy it. She didn't want details, but she was happy that I had a good time.

Of course, one does not take the genie out of the bottle and simply put it back again without... repercussions. I'm 51 years old. Not a scared kid any more. I wanted to do it again. The dressing, not just the sex (although that was wonderful!), but the dressing. Not all her things fit me, but she did have a pair of panties and stockings that felt sooooo good to put on. I wanted that feeling more and more.

I did, very briefly, use my wife's panties (she had a few pairs that fit), but quickly realized this wasn't a temporary thing, and bought my own, along with some stockings, and a pair of dressy heels. I then bought a black a-line skirt, a pair of flats, and a pretty purple top with some embroidery on it.

Yeah, this is not going away any time soon, and I don't really want it to. The guilt and shame are still there to some extent, but I'm working through it. They're more like a reflex at this point, and I know where they came from. My father is long out of the picture, so that's not a factor any more.

I don't see myself as trans-sexual. I've never felt displaced or in the wrong body, most of the time I'm happy being a man. From time to time, though, I love to let my inner girl (for lack of a better term) out into the world. I've always been more (to use a hackneyed phrase) in touch with my feminine qualities than most guys. Honestly, it's something that's served me well over the years.

So, to get to the actual point of all this... my wife has been away visiting family for a couple of weeks. The encounter I refer to happened right at the beginning of her trip. I've been dressing again for that time. I've read some stories here about girls who told their SO years after they started dressing or met for the first time, and I've seen how bad getting caught can be, first hand, and by the experiences of others. I've decided this is something I need to tell her. Our marriage has always been based on honesty and communication. It hasn't been perfect, and we've had some pretty rocky times. We got some counseling that helped us work through some of our issues, and we're still going strong. I don't want this to be something I hide from her.

So I need to tell her. I want to tell her.

In my mind, I am confident that this will not be a huge issue. She's a kind, loving, compassionate person. She has experience with knowing crossdressers, and has been friends with a couple.

My feelings, however, are not so easily soothed. I still remember how it felt to get caught. I still (even though I know where they came from) have feelings of guilt and shame. I'm still scared she will reject me.

It's not a rational fear, mind you... and I know that. But it's there, and I'm trying to deal with it.

So hey, any advice? Pearls of wisdom? Dire warnings? Advice welcome and eagerly sought, either here or in PM if you prefer.

Megan

Since you have a relationship built upon honesty and openness, The Talk should be pretty easy. The aftermath, however may be disappointing.

Only you know your family dynamic, but I would advise being as candid, factual, and unemotional as that dynamic permits. Answer each question quickly and truthfully, but only the questions that are asked. To do more runs the risk of information overload or bringing up something unexpectedly harmful.

I am afraid of heights. It's an irrational fear, but the response is the same as if it was rational.

Best wishes
MsVal

You are having sex with men and women and she's ok with it. I can't imagine cross dressing would cause concern.

I'm with Jennifer, it shouldn't be a problem. And .. BTW... you're a lucky guy to have such a wife.

Since she already know quite a bit about you, and your meeting a man, "Cheaters" should not be watching you. Be honest, and it should be not too bad.

Given the information in the OP, I doubt that your spouse will view CDing as anything out of the ordinary. I think that the anticipation will have been worse then the talk.

Hi Megan, This sounds mild in comparison to everything else.

This is in line what what my mind says will happen. It's just those pesky feelings ;) I am very lucky to have her and very happy to still be with her.

I'm planning on telling her Monday, so wish me luck ladies.

Thanks for the encouragement.

Megan

Hi Megan,

I would approach this exactly as you did when you discussed your desire to explore sexual relations outside the marriage (male and female). Open and honest. I get the impression your wife has an understanding nature and will view this in the same light . . . try it and see if it is something you want to pursue. Once the topic is out then you can discuss how best to proceed (for both of you).

Hugs and good luck.

Isha

While I fully agree with those who think she'll be fine with it, I offer a couple suggestions.

Tell her fiest, don't show her yourself en femme as an opening gambit.

Ask if she wants to watch you transform, or wants to see the finished product for an A/B comparison.

Don't show her your femme self in better clothes, better makeup, better as a woman, etc. than she is. Most women want to BE the woman in the relationship. Leave room for her to offer you suggestions on how to improve your look, walk, makeup, presentation, poise, maners, voice, hair, choice of age appropriate clothing, etc.

Some women get jealous of our femme selves and resentment can build. Your wife already has show an embracing of openness in your relationship. Is you approach this "reveal" properly, you'll open up a whole new dimension of trust, fun, and possibly opportunities to go go places as sisters/friends.

Good luck, report back, and of course, pictures!

Best,
Rhonda

You seem to be embracing all types of sexual encounters, why is cross-dressing a big issue?

So, for those curious about what happened and how it went... the simple answer is it's still going. There were difficulties, there were some tears, both hers and mine. It was a very large shock to her. And while she is most definitely liberal in her outlook in general, it struck way close to home when it was her husband, not someone else. Bless her, she is working her way through things, processing the info. We talk from time to time. We can even joke about it a bit. She wants to be ok with it, she really does. And she's doing her best. I'm cautiously optimistic.

As it turns out, I'm not entirely done with dealing with my own guild and shame as instilled in me when I was young. So I'm going to get some help in coming to terms with my own past, and she's going to get some help in dealing with the present.

I suspect this will be an ongoing thing as we learn to be comfortable, her with me dressing, and me with her knowing I do.

Thanks to all for the help, the advice, and the caring.

Megan

Quote:

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Originally Posted by MeganDay

So, for those curious about what happened and how it went... the simple answer is it's still going. There were difficulties, there were some tears, both hers and mine. It was a very large shock to her. And while she is most definitely liberal in her outlook in general, it struck way close to home when it was her husband, not someone else.

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I'm sorry I didn't see your earlier post. I'd have warned you this might be the case. I know that many members here get squicked by any activity involving someone else's penis, but for a lot of women, that's easier to take than gender issues in their spouse. Guess you found that out for yourself, huh?

I hope the two of you are able to work it out. Don't be surprised if you are in for a bit of a rollercoaster ride. Her feelings may change quite a bit over time until she reaches acceptance of this finally. (Note: Unfortunately "acceptance" doesn't mean she accepts that you do this and is cool with it - it just means she's resolved it in her mind.)

Maybe the most important thing to understand is that you and your wife are currently at different levels of emotional intensity. If cross dressing and the whole gender thing is really new, exciting and all encompassing for you it really might not be for her. I know how difficult this may be for you but maybe you should, at least in front of her, slow down. affrirm to her how important she is in your life, how nothing really has changed in your love for her, and how this is just a personal adventure and exploration for you, not a threat to her. And, even though you may have her permission, for a while, don't sleep around. Consider that you have two large priorities. You have to explore what it means to you to be transgender, to present as a gender other than the gender you have always considered yourself to be. This is a big deal. An equally big deal is protecting your relationship with her. She seems like a great companion. Value that relationship as much as you value your need to explore this part of your personality that you hid for so long. This is complicated stuff. Do yourself and her a favor and take it slow. Having sex with other people, while absolutely okay in your marriage, may be something that would really increase the complexity of what you and she are trying to do. Even in non monogamous marriages there are times when you maybe should not deliberately increase the variables.

Quote:

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Originally Posted by devida

Maybe the most important thing to understand is that you and your wife are currently at different levels of emotional intensity. If cross dressing and the whole gender thing is really new, exciting and all encompassing for you it really might not be for her. I know how difficult this may be for you but maybe you should, at least in front of her, slow down. affrirm to her how important she is in your life, how nothing really has changed in your love for her, and how this is just a personal adventure and exploration for you, not a threat to her. And, even though you may have her permission, for a while, don't sleep around. Consider that you have two large priorities. You have to explore what it means to you to be transgender, to present as a gender other than the gender you have always considered yourself to be. This is a big deal. An equally big deal is protecting your relationship with her. She seems like a great companion. Value that relationship as much as you value your need to explore this part of your personality that you hid for so long. This is complicated stuff. Do yourself and her a favor and take it slow. Having sex with other people, while absolutely okay in your marriage, may be something that would really increase the complexity of what you and she are trying to do. Even in non monogamous marriages there are times when you maybe should not deliberately increase the variables.

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If I could have said it this well, I would have said the same.

You're in deep. I think you should be thinking about just how important she is to you, and how important it is for you to explore all your new toys. It's powerful stuff.

Rhonda and Devida, that is something I already decided, but thank you for the advice. It serves to confirm what I was already feeling. I agree that she needs reassurance and love right now and she needs to know that she's still the most important thing in my life. For what it's worth, I've never slept around. In 51 years of life I've had less than 10 partners, three of which I was married to, and the rest were relationships, not flings.

Paula, thank you for your thoughts, too. I've definitely come to appreciate your thoughts on other posts I've seen.

I still maintain cautious optimism. We've been through a lot together and neither of us is ready to just let all that go right now.

Thanks again, all; you've helped make it better.

Megan

Just the simple fact that you are communicating is a clear signal to me that you two will be able to work things out! Bravo!