One Step Closer To Telling S.O.

[LisaDee]

My wife says we should be a couple for Halloween only she would be male and I female. WOW! Here is my chance to feel her out on the subject of me crossdressing. I ask what kind of outfit and she says a nice fancy gown. I respond and say I would like to look good and will need nice shoes and jewelry. The discussion continues and I say I would really like to look nice in womens clothing and have thought about it before. I say it is not fair that girls can wear guy stuff and guys can't wear girl stuff. I go on about how much nicer girls clothes and accessories are and she says skirts really are comfy. I say maybe I should try one if I like it I may turn into a crossdresser. She says well if you want to wear that around the house go ahead. Hmmm...this may be the opening I needed.

[suzanne]

On the face of it, it looks like your wife may indeed be OK with your crossdressing. But go slow. Once she sees the extent of your interest, she may have second thoughts and do a 180 on you. The voice of wisdom in this forum consistently says to let her dictate the pace of your progress into CDing, only moving forward when she indicates she is comfortable. Best of luck to both of you on your journey!

[LisaDee]

On the face of it, it looks like your wife may indeed be OK with your crossdressing. But go slow. Once she sees the extent of your interest, she may have second thoughts and do a 180 on you. The voice of wisdom in this forum consistently says to let her dictate the pace of your progress into CDing, only moving forward when she indicates she is comfortable. Best of luck to both of you on your journey!

Thanks Suzanne. Sounds like good advice.

[kimdl93]

well, you sort of told her. I mean, really, you pretty much said "I like cross dressing". Anyway, I guess I'd take her up on the offer, and try to begin a conversation, not about hypotheticals, but about your real feelings and hers.

[Vickie_CDTV]

She probably already suspected you had an interest in crossdressing, and suggested dressing up for Halloween as an opening for you to tell her.

[LisaDee]

She probably already suspected you had an interest in crossdressing, and suggested dressing up for Halloween as an opening for you to tell her.

I think you may be right but, I still am going slow.

[MWCMDarlene]

Could it possibly be that just as much as you want to come out to your S.O., that your S.O. is in the process of feeling you out so she can come out to you? Wouldn't that be a card?

[LisaDee]

Could it possibly be that just as much as you want to come out to your S.O., that your S.O. is in the process of feeling you out so she can come out to you? Wouldn't that be a card?

That would be crazy! Not likely though.

[Jenniferathome]

You can't hint your way to telling her. She may think it is a joke. Her suggestion is just a lark. Come clean once and fully. "Honey, your Halloween idea is mighty surprising. I have something I need to tell you...."

[Leslie Langford]

The danger in using Halloween as the lead-in to any discussion around crossdressing is that in making that particular association at the outset, you run the risk of relegating it to the equivalent of the infamous "friend" zone in a. male/female relationship, and from which there is rarely any escape...

[Chickhe]

The trick with Halloween, its not a time to be yourself. You are wearing a costume. And repeat it to yourself so your feelings don't get hurt when she or someone else laughs at you... But, what Halloween is good for, it eliminates the shock factor, of seeing you dressed up. What you want to do is make the experience very positive for her. First impressions are important. Also, pay equal or extra attention to her costume, otherwise she is going to feel left out. And don't explain anything (she won't understand and it will scare her), nothing about how you feel, just let her observe and make up her own mind.

...later on, when you are talking about how much fun it was, tell her you want to do it again...on a regular day to see if you really can pass yourself off as a woman... take it one step at a time.

[Angie G]

That's just how I started with a skirt that my wife let me wear after almost the same conversation. Now I dress head to toe 5 day a week and give her her husband an the weekends.:hugs:
angie

[heatherdress]

Lisa - You know your wife better than anyone on this web site. If Halloween is an opportunity that you believe is best suited to open discussion or convey your crossdressing desire - use it.

Like people caution - go slow, be sensitive, be candid.

[Jacqueline Winona]

My wife figured out that I enjoyed dressing from a Halloween experience. It kind of grew from there, I hadn't really admitted it to myself before then (this is pre-marriage). One of those things I knew I liked, no idea why, thought it was weird, etc. She still doesn't like it, doesn't want to know about it, but she does tolerate me doing it. You're doing well so far, take things slow and just focus on the moment. She will probably figure this out just like mine did (if she hasn't already), but you'll know how to approach the next step.

[Beverley Sims]

Lisa,
The door has opened, try it in stages and let yourself be led by your wife's feelings.
Do the Halloween bit as well as you can. If you do a good job others will be impressed and are unlikely to talk as they will be impressed with what you have done.
I know on occasions when I have done the woman bit to perfection at work parties all they talk about is how good I looked.
Nothing about my odd ways. :)

[Tawne]

Well you potentially have 2 roads to take. The first being the more honest one where you tell her that this has been going on since the beginning of the relationship, she may be angry that it was held from her, and then all sorts of things will pop into her mind like "what stage are you at" "what have you done" "what else has he lied about or kept from me". The second road you can take is to go ahead with the whole thing and play it nice, come home and have some really kinky love making and from there you can express that you find it really sexy or whatever. This is the dishonest way, not saying it's the right or better way either, but she will believe it is the beginning and she was there to witness it so she has more control over it and knowledge of your status, just my 2 cents.

[LisaDee]

Now it looks like we won't be going out for Halloween. I told my wife I would still like to dress up, that I would like to wear some heels, stockings and a bra. She says, " now you starting to freak me out." I let it lay from there, I am hoping she brings it up again
.

[daviolin]

Oh boy, don't kick this gift horse in the mouth. I think your on the way to success there girl. Daviolin

[LisaDee]

Do you think she will bring it up again or should I?
Oh boy, don't kick this gift horse in the mouth. I think your on the way to success there girl. Daviolin

[NicoleScott]

She says, " now you starting to freak me out."

Yowee. Not a good sign. But what to do? Back off for now, or is it time to reveal your drive to dress? You hinted at it, and got a sign that she may not be accepting of the idea.

[LisaDee]

Bring it up another time or keep it secret?

Yowee. Not a good sign. But what to do? Back off for now, or is it time to reveal your drive to dress? You hinted at it, and got a sign that she may not be accepting of the idea.

[samanthasolo]

Oh LisaDee,
It sounds like she might already know about your dressing, or at least have an idea. She could be feeling you out and want you to come clean. You have heard of woman's intuition haven't you. Well, if she has an inclination and this is her way of working toward getting more answers I would think this could be her way of trying to get things out on the table without accusations, or a potentially embarrassing or awkward situation in the future. Of coarse this is my own opinion and I could be reading into it more than it really is. It is regardless an oportunitty to not only clear your concience but also an avenue that might open the door for you to not be keeping a BIG secret from her.

[Robbin_Sinclair]

Lisa,
The door has opened, try it in stages and let yourself be led by your wife's feelings. Do the Halloween bit as well as you can.... :) Beverley is so on spot, as usual.

Yes, that's my take, too. Make THAT MOMENT special. Do go thinking like General Patton to win the war. There is no war. Do whatever you can do to have as much fun on Halloween night. This is not about leveraging an opportunity. This is just plain fun. Carpe THAT diem.

[KC Samanatha]

I can only speak from my pov of course but, the most freeing day was when I shared with my wife. Sadly it took 3 rum and cokes for it to come out. She had noticed like all women do the subtle things about her clothes or make up and etc.
Never ever an easy talk to be sure.
Good luck and go slow is my belief

[Robbin_Sinclair]

Not sure about the 3 rum and cokes (being a quitter) but one thing to think about, if you haven't already done so, practice the walk. For me it made it much easier to have that looseness that comes from femininity.

With that the hands and arms are next. Then, when cradling that rum and coke (or club soda with a twist) you take a deep breath and feel the moment.

Sounds wonderful! Enjoy.

[NicoleScott]

LisaDee, this is a tough one, because your wife has sent you mixed signals. In your OP, she said "wear what you want to around the house" but as you pursued that she said "now you're starting to freak me out". I can see how it's hard to know how she really feels about it.
You know the situation better than anyone, but here's what I think (and did). It took a long time, but the opening came when my wife mentioned a CDing article she was watching on TV or reading in a magazine (I forget which, but it doesn't matter). In the discussion that followed, I took a "harmless fun" position which she agreed with, and she started asking me questions like "did you ever want to...?" (yes) "did you ever..." (yes) "did you enjoy it?" (yes) "do you want to do it again? (yes). "Well, DO IT!" Well, I did, but here is my point: as long as the conversation remained positive (acceptance), I opened a little more, finally revealing all, but I was ready to shut it down if things started going negative (non-acceptance).
I know some people think it's best to go full steam ahead, but in reality there could be an iceberg ahead, and practicality says to slow down and avoid it.

[Lacyfem]

Don't over complicate and read anything into your wife's thoughts. Just let her dress you as she's accepted the Halloween thing so don't look to anxious about it but play it cool. But do say to her, if I'm going as a woman I want to be totally a woman and not just a skirt and blouse and flats. But you want a fitted bra and panty with some thigh highs and heels or even tell her you want to be as sexy as possible and wear a nice garter. Try not to let her know how excited about it so as not to totally give away immediately what you want. Then be as fem as you want to at the Halloween party and when you two get home I think you should passionately make love to your wife and tell her how wonderful you felt allowing your fem side out and would like to do it again with her help. By making love to her passionately she may see the benefits to her for allowing your fem side to come out more. Play it cool but keep her in the picture to help the gurl she loves become more of a gurl yet a man in bed with her... Good Luck...