Me trying to "work this out" with myself and possibly(& hopefully) my S.O...Help!:/

I'm somewhat still "new " to the idea of actually being a CD or whether I'm curious or confused...I know that I enjoy dressing and making up.I even own my own panties and cute house-top.I also know I''m not looking to CD full time,and that I myself am not TS or TG.I don't ever want to CD in public;this is just for me to have safe thrills and experiences at home.But this has been fairly sporadic honestly as of late.

~I have a SO though,who is pretty 'vanilla',but I still feel and am Considering telling them.
~They aren't prejudicial or anything,but in our relationship,I feel like I have already been asking a lot of them in terms of opening up boundaries sexually and that maybe this would "push it to far".
But full story though:they at some point dressed and made me up themselves!They said they felt like they were playing with a life size Barbie.
~You might be thinking;"what the problem then?"The issue is that I guess I may have 'overacted' ,because now my S.O never even brings up or jokes about dressing me up.My SO even said something to the effect of
"oh I know how much you hated that,and I'd never put you through that again." I have tried bringing it up again as another "bet" we can make (thats how it happened the first time),but they aren't vibing on it positively anymore:/

So now I'm just sort of dressing in spurts secretly and don't know how to approach this with them.Like,I don't want to 'come out to' them with this,because then I think it'd make it seem negative or dramatic or something.I was hoping to erase the idea that I'd never do it again AND get them to act on it by dressing me so I can share and maybe explore this more openly with them.

Thoughts on how to approach my SO?Am I being too timid trying not to "push things more/bring CDing up " with them?ANy other perspectives would help so much!

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Originally Posted by closetcd17

I'm somewhat still "new " to the idea of actually being a CD or whether I'm curious or confused...I know that I enjoy dressing and making up.I even own my own panties and cute house-top.I also know I''m not looking to CD full time,and that I myself am not TS or TG.I don't ever want to CD in public;this is just for me to have safe thrills and experiences at home.

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Don't worry too much about what category you fall into. The answer will reveal itself in time, and you have plenty of time to explore.

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Originally Posted by closetcd17

...they at some point dressed and made me up themselves!They said they felt like they were playing with a life size Barbie.....because now my S.O never even brings up or jokes about dressing me up.My SO even said something to the effect of
"oh I know how much you hated that,and I'd never put you through that again." I have tried bringing it up again as another "bet" we can make...

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OK, the ice has been broken, but communication is currently in a jumble. Neither of you really knows how the other feels about this.

Your job is to communicate with your SO clearly so that you both can understand what you desire. Avoid subterfuge about making bets or trying to maneuver her into suggesting it herself. Just put it on the table and see what she thinks of it.

Say something like "Hey, remember when you dressed me up? I really had a good time and I'd like to try it again!" She'll probably have some questions for you and these can be the catalyst for a deeper conversation. In the process explain to her that this is a topic that you might have difficulty talking about but that you will do your best to be frank with her.

This is the first conversation and you will likely have many more.

If I was in a situation similar to yours, before I told my wife, I probably would have reacted about the same as you did. I think that would have been the fear of someone finding out about me; which is something that I hid for many years. Not knowing how your SO would respond, and no one really knows, I think that I would be totally honest with her and tell her that you like dressing up. She might not understand why you lied to her, but it sounds like she cares about your feelings and might be okay with it. As far as anything sexual, you are on your own.

She dressed you up, that's when you should have talked, and made sure you where having fun with it. Now you need to open up and talk to her about it. Why did she think you hated it so much, did you hide to well? I've yet to see a wife, or mother, that could really read minds, they may want you to think they can, but the can't really. If you want to know what she thinks, you have to tell her what you need to know so she can tell you. Then maybe you can get into a DADT, or better relationship. But either way, you talk to her, then there is no sneaking around, and getting caught is not a big surprise to her. And she might have enjoyed dressing you up, but is not sure how you feel, because you didn't want to give up to much about that side of yourself. There is only one way to be sure about what anyone thinks is to ASK!
Tina B.

Its simple. Do what I did. Get careless. Leave your stuff around. Don't change back to drab when she is out until the last possible moment. When she finds a pair of panties under the bed--you will have a discussion--it will quickly become clear.

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Originally Posted by Tina B.

She dressed you up, that's when you should have talked, and made sure you where having fun with it. Now you need to open up and talk to her about it. Why did she think you hated it so much, did you hide to well? I've yet to see a wife, or mother, that could really read minds, they may want you to think they can, but the can't really. If you want to know what she thinks, you have to tell her what you need to know so she can tell you. Then maybe you can get into a DADT, or better relationship. But either way, you talk to her, then there is no sneaking around, and getting caught is not a big surprise to her. And she might have enjoyed dressing you up, but is not sure how you feel, because you didn't want to give up to much about that side of yourself. There is only one way to be sure about what anyone thinks is to ASK!
Tina B.

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Tina has a good point. She may have really enjoyed dressing you up but in her inside world she thinks you didn't like it so much. She might also feel silly for doing it... so many possibilities and the truth is you don't know what she is thinking, whatever she says to you.

I hate giving advice as all our situations are different, but if this was me I would try to get back that place... and say how you 'kind of' enjoyed it... and ask her how she felt about it... this looks like a great place to explore the possibility of telling her how you really feel... but go slowly... sow seeds and let them grow! And if they don't, then you will still know more than you do now!

Seems you are saying the you never crossdressed before your SO dressed you up, yes?

Then you have no reason to hide.

When she dressed you, it was like setting a match to gas. It sparked something inside you you weren't cognizant of.

This happened to many of us the first time we dressed. It started a fire that can't be permanently put out.

So, sit down with your wife, explain in those terms, explain how you fought the fire but it keeps burning. Make sure she knows it's not her fault. Many of us are just predisposed to this characteristic.

Ohh yeah!! Confess.... Tell her its her fault for dressing you up to start with and now there's no putting the genie back in the bottle. She will have to accept you just out of guilt alone! Lol. Its like a get out of jail free card! More like a get out of the closet free! :)

You really have to talk to her about this,dressing in secret is only going to cause problems later.
Why not go out for a meal and have a few drinks together, but dont get drunk,then slip in the conversation about the time she dressed you and how much you really enjoyed it and would really want to do it again.
she may be surprised and have a lot of questions to ask back.But at least you are being honest and she may like having girly time with you, seeing a different side of you
Either way you have to talk and be as honest as you can and go slowly,find out what she is comfortable with
Good luck

Cindy

It's actually a lot easier than you think it will be. I've told two women both have been accepting and one I married. If you want to have a long term relationship with her, then it's in both your best interests to tell her. Be honest, you already know she can be accepting but can she be accepting over the long haul. Work it out together, set boundaries, don't make it all about you. If she is cool to the idea, tell her you can dress alone, you want to help her accept this part of you and there is no pressure. This is not advice for everyone but you would already know if she would not be accepting or you wouldn't be considering it. Go for it and good luck.

[OP here]

""Hey, remember when you dressed me up? I really had a good time and I'd like to try it again!" She'll probably have some questions for you and these can be the catalyst for a deeper conversation. In the process explain to her that this is a topic that you might have difficulty talking about but that you will do your best to be frank with her."
~~ Supposing I bring it up and she's still lukewarm/nit into the idea of dressing me up anymore?Do I ASK THEM to dress me up the way they asked/made me the first time?Would that be "pushing it" do you think?

"She might not understand why you lied to her, but it sounds like she cares about your feelings and might be okay with it. As far as anything sexual, you are on your own. "
~~I am nervous about bringing it up that I fibbed,but I think you are right that she would get WHY I did.And what do you mean by I am on my own exactly?

"...if this was me I would try to get back that place... and say how you 'kind of' enjoyed it... and ask her how she felt about it... this looks like a great place to explore the possibility of telling her how you really feel... but go slowly... sow seeds and let them grow! And if they don't, then you will still know more than you do now! "
~~`What do you mean 'get back (in?) that place?'
And I do think it's a good idea to ask how she felt about it in more detail.I just honestly don't know how to BRING IT UP? It's not like I bring up wanting to dress up as jokes that often if ever!

(To all) honestly,I'm also nervous that she MIGHT not take it well,and I really want her too.Like ,if it came down to it and I had to tell her,I DON'T wanna spring it on her like it was "bad/extremely heavy news".
Lol,like if it were up to me the worst case would be her being just sort of indifferent/puzzled and at best wants to play Galpals and dress/make up together more often.
I know I sound like a weenie,trying to "come up with something" instead of taking this head on;but again I am nervous!!!!:/

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Originally Posted by closetcd17

But full story though:they at some point dressed and made me up themselves!They said they felt like they were playing with a life size Barbie.
~You might be thinking;"what the problem then?"The issue is that I guess I may have 'overacted' ,because now my S.O never even brings up or jokes about dressing me up.My SO even said something to the effect of "oh I know how much you hated that,and I'd never put you through that again." I have tried bringing it up again as another "bet" we can make (thats how it happened the first time),but they aren't vibing on it positively anymore:/

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When you say you overacted, does this mean that you protested too much? Or do you feel that you came off as enjoying it too much? (or maybe it is both ... you protested but she read right through you in which case the red flag might have been the mixed messages).

If it is the first, I'm with Eryn. You need to come clean and say that you were embarrassed about letting her know that you do enjoy expressing femininity on occasion. And then take it from there. Answer all her questions. But, first you'll need to answer them for yourself. :)

If it is the latter and the two of you have not processed this, she may have gotten turned off because it is one thing to share an intimate moment with a boyfriend if she is secure in the knowledge that he is very much a guy enjoying a sexual escapade as a guy, and quite a different story if she feels there are deeper gender issues. Most GGs do not know the difference between needing to express femininity on occasion and having this be the beginning of a secret desire to transition. Very few people who are not in this community understand how wide is the spectrum of gender non-conformity.

P.S:there are somethings I've said to her and she's said to me in the past that make me feel more confident she might not overreact negatively:

*I've said in the past that I'd prefer to be pretty instead of macho
*She constantly,even today, says stuff like I am a pretty guy and 'prettier' than her.
*She has said she's "trying" to be more sexually open as long as it is just between us (she's very anti-threeways and/or Swinging)....
*She was cool enough to let me buy her toys with which we may experiment in the bedroom.
*She jokes about me being the 'housewife'

I can understand you feel nervous, but afterall this is your wife, she knows you better than anyone and is meant to be your best friend and with you for life. As for hitting it head on...don't. Just be honest, sincere and do not push anything on to her. Just a little at a time, if she does not bring it up again after some time then you need to reproach it again, honestly and softly. Because she did dress you up once its highly unlikely that she will react very negatively. Once you get to talking about it, discuss boundaries....again just be honest and understanding.

Hugs
Natasha

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Originally Posted by Karren Hutton

Ohh yeah!! Confess.... Tell her its her fault for dressing you up to start with and now there's no putting the genie back in the bottle. She will have to accept you just out of guilt alone! Lol. Its like a get out of jail free card! More like a get out of the closet free! :)

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Is it smart to guilt her ? ( Or if you were kidding ,also let me gullible ass know);I DON"T wanna male htis a negative thing for her in anyway if I can help it...

You seem to have good feelings about your SO, and that is good. Simply sit down and open a conversation with something like, I want to talk with you about me being pretty, which you have mentioned also, and the time I was dressed as a woman. Be prepared to say you felt pretty doing it. Be prepared to say you have fond memories, and would like to feel them again. Be more than prepared to ask her what her feelings were while you were doing it, and talk a long time about those. Be prepared to have her not like it, and not want to do it again, and then you can talk about what it means to be a crossdresser, and let her know that is what you are.

Starting the conversation will be simple. Getting the courage up to start it will be hard.

Barbara

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Originally Posted by ReineD

When you say you overacted, does this mean that you protested too much?

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I think I did.
I acted like I was embarrassed about being made to look like a girl.
She also kept asking me over and over and over for pictures,and I finally settled for letting her take one then delete it.Honestly I was embarrassed about the photo mainly because I didn't want anyone to ever ever find it.

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Originally Posted by ReineD

But, first you'll need to answer them for yourself.

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What do YOU mean by this;can you elaborate?

As several have already suggested, why not find an opportunity to bring the past experience up and let her know that you enjoyed it more than you were able to admit, and that you would like to do it again.

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Originally Posted by kimdl93

As several have already suggested, why not find an opportunity to bring the past experience up and let her know that you enjoyed it more than you were able to admit, and that you would like to do it again.

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I'm embarrassed and honestly a little ashamed I "blew" the opportunity to explore this earlier by fibbing.

Lol,it's like I know what I have to do,but making myself ,or thinking about it,gives me the meanest butterfles:/

oh! and just btw;me and my SO aren't married,we are in a LTR (more than 5 years).

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Originally Posted by closetcd17

Is it smart to guilt her ? ( Or if you were kidding ,also let me gullible ass know);I DON"T wanna male htis a negative thing for her in anyway if I can help it...

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I think that Karren was kidding a bit on this one. Guilt is not a good motivational tool.

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Originally Posted by closetcd17

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Originally Posted by ReineD

Answer all her questions. But, first you'll need to answer them for yourself. :)

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What do YOU mean by this;can you elaborate?

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I'll stick my nose in to say, from a CDers point of view, if you wait until you've answered all the questions for yourself you will never talk to your SO. Every answer yields more questions! Consider your SO to be a partner who is sharing in your gender exploration. In any case, communication is important and you've already started since you can talk about your "dressing up" experience with her. It just takes the courage to admit to yourself and to her that "heck yes, I enjoyed it!"

You can not hint or bet your way into telling her. just sit down and tell her. Take your time and let her take hers. Keep crossdressing out of the bedroom whatever you do. Be 100% honest. If you hedge now, she will find out and it will,come to color everything she believes in the future.

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Originally Posted by closetcd17

[OP here]

""Hey, remember when you dressed me up? I really had a good time and I'd like to try it again!"

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This is a really bad idea. It is not honest. You are hinting at the real truth. You can't communicate this in controlled doses.

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Originally Posted by Jenniferathome

You can not hint or bet your way into telling her. just sit down and tell her. Take your time and let her take hers. Keep crossdressing out of the bedroom whatever you do. Be 100% honest. If you hedge now, she will find out and it will,come to color everything she believes in the future.

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That's the best advice available!

You do realize of course this could backfire on you? VVVV

"I also know I''m not looking to CD full time,and that I myself am not TS or TG.I don't ever want to CD in public;this is just for me to have safe thrills and experiences at home".

According to prevailing theory and POV at this Forum, [wrong btw] ALL CDers will eventually want more. Maybe you would and maybe you wouldn't. BUT what if your SO got so involved and wrapped up in the whole thing, SHE wanted you to go out en femme with her? And you have no desire for such. [for now at least]

IS CDing something you want her help with or participation in? Seems like the answer is a definite yes in your case. Talk to her about it and clear the air while it is still fresh. You have already gotten some great suggestions on how to break the ice.

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Originally Posted by closetcd17

Is it smart to guilt her ? ( Or if you were kidding ,also let me gullible ass know);I DON"T wanna male htis a negative thing for her in anyway if I can help it...

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Hell yes its smart. How many times has she guilted you? Boom. Guilt is the ultimate equalizer. Lol.

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Originally Posted by closetcd17

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Originally Posted by ReineD

But, first you'll need to answer them for yourself.

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What do YOU mean by this;can you elaborate?

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I mean you should read this forum a lot, decide where you fit in with all of this (if you can), so that you can have some concrete answers for your girlfriend when she asks the following questions:

Are you gay?
Do you want to be a woman?
Why do you do this?
Do you want to dress because I am not enough for you?
Is this just sexual for you?
How often do you think you'll want to dress?
Are you wanting to tell everyone?
Do you think you'll want to go out in public, and if so where and when?

... and maybe a few other questions. :)

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Originally Posted by ReineD

...
Are you gay?
Do you want to be a woman?
Why do you do this?
Do you want to dress because I am not enough for you?
Is this just sexual for you?
How often do you think you'll want to dress?
Are you wanting to tell everyone?
Do you think you'll want to go out in public, and if so where and when?

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Thank you Reine.I can answer the majority of those questions thankfully.
The only ones that I think are tricky for me are :
"WHY do you do this?
[Do I ] dress because[she is ] not enough for [me]?
Is this just sexual for [me]?"

I don't know if my answers are "good enough".
~For example, the reason I feel I do this as of now is because I enjoy exploring my fem side on occasion,and I feel the clothes and makeup are helping me do that;sometimes as I honestly feel my moods perk up when I'm all 'pretty n dressed'.
~I also know I enjoy the experience in a sexual way too,but I don't want to transition into a woman at all;I also just honestly enjoy/have FUN going back and forth between male and female.I like ,and I think everyone in general likes, to feel attractive.I like feeling like a stud when I'm a boy ,and a smokin hot number when I'm dressing like a girl:D

~How often I guess depends on their comfort levels as much as my own;I don't know if she'll want to see my dress myself up if its not like a game between us (I don't want her thinking the wrong thinking that I wanna transition one day or something)and I do not know if I'll be so comfy letting her see me that way to much....I think like years of male programming still make me feel ashamed to have her see me as not/less-than a full man....but then at the same time,I'd love to play girlfriends and you know,just try on outfits,make each other up,etc.LOL I feel that if I could get a real girls touch I can take my CDing to a higher/and more attractive ,level.

~How I'd express my sexuality I'd tread carfully though.SHe knows I'm bi,or at least very bi-curious,but I don't know if that's something she'd be able or even willing to see in me.Not because of any homophobic crap,but because she very much likes to keep everything between JUST us;for example,she felt GUILTY for having a CRUSH on another guy she worked with last summer!And a few years before this,she felt very very uncomfortable when I told her some young woman I was tutoring tried to hold my hand (even though I politely and quickly rejected that advance)Can you believe that?! lol.SO ,by extension,I can only see me expressing sexual interest out side the 2 of us as sort of a "no-no."


Thoughts?

I really need some assistance ;does anyone else have any other input?

For Reine's questions and any others that come up a perfectly valid answer is "I don't know." Other answers might change with time. You will never have complete information. One really important thing is to avoid promising things that you might regret later.

At this point you've had a lot of good advice. What you do with it is your business, but I think that you need to be having a serious sit-down with your SO. Lay it out for her then listen carefully to what she has to say.

Sorry for not expanding further. It's true that you may not have all the answers for awhile. But, these are the questions that she will likely ask and it wouldn't hurt for you to think about them. Whatever answers make sense to you are certainly "good enough", since they will be how you feel.

One of the questions that my SO was never able to answer, was "why do you do this". Well, she actually did answer. She told me that it was as difficult for her to explain "why", as it is for me to give a good solid explanation as to why I like classical music or art. Or skiing. Or doing Sudokus. :)

Another answer my SO could never give was, "What is it exactly that causes you to want to dress on some days and not on others". She just said that she had no clue, any more than I know why I might feel like listening to music one night and reading a book another night.

And the answer to any girlfriend when she asks, "Are you doing this because I am not enough for you", is universal. It is a resounding, "NO!". :p

As to the question, "Is this sexual for you", well, just tell her how you feel. Whatever it is will be the right answer for you. :)

Lol,thank you all for your input!

Of COURSE,any other insights are always welcome...

I must say though,I am QUITE the CHICKEN apparently;I keep losing my nerve when a good segway to discuss this presents itself!:o

You tell us you are quite the "chicken" about talking to your girlfriend. Please realize that this isn't all about you, but about your relationship. This keeping your secret to yourself affects how you relate on a daily basis with your girlfriend.

If she were to keep a similar secret from you I think you would notice she was keeping her distance from you and it would affect how you felt toward her. You can let her know that you are fearful of how this information will affect her and your relationship but that you realize it is more important that she knows. Please don't let your fears get in the way of becoming closer with her.

Karan