How do I know when it's time?

[prettytoes]

My wife discovered my stash of clothes in April. It was rough at first, but now she is fairly accepting, and our relationship has never been stronger. She did tell me that she didn't want to see me in a skirt or dress. I wear bikini panties 24/7, sleep in nighty's, wear sport bras when I'm working out, lounge around the house in women's yoga shorts, and keep my toenails painted. She does the laundry, so she sees it all.
My question is, when will I be able to wear a skirt (I prefer denim mini skirts) and blouse in front of her? This is all still fairly new to her, and I can tell that at times she is still a little uncomfortable (we have been married 27 years...I know her well). For now, I wear a skirt when I am watching the morning news and enjoying my coffee, or when I am home alone. I sleep with her, so she sees me in a nighty every night. I would love to be able to dress in the evening while relaxing, but I do not want to push her too far. How do I know when she is ready?

[Stacey Summer]

It sounds like she is already more accepting than my SO. As others will no doubt say, she needs time to come to terms with the idea. If you haven't already I highly recommend reading the "How to tell your partner" thread. Sit her down and have a conversation about it. Answer any questions she has and be ready to hear things you might not want to hear. Just don't push too hard or she's likely to feel trapped and pressured and that would be bad for your relationship. I hope it works out for you, good luck.

Stacey.

[Gillian Gigs]

Their are 2 scenerios here. One she within a reasonable period of time she get used to everything. Two she will never get used to certain articles of clothing. Your marriage should be based on love and compromise. The compromise part in the CDing area will come after several long talks. After 15 years my SO still does not want to see me in a bra, and yes they do end up in the laundry basket. She sees me in all other lingerie, she just has this thing for not seeing me in a bra. What's under a shirt can not be seen and that is ok, go figure, but that is one of our compromises.

[5150 Girl]

Every situation is difrent. Keep an open dialog, but don't force the issue. how do you know where the lie is between keeping it open and forcing it? Only you can your spouse can anser that.
Sounds like she's ok with underdressing. I think I may just leave some ohter items arrouns the house... leave a skirt on the bed, a blouse on the couch. When she gets used to that, one day say, "Ya know honey, I ain't go'n nowhere today, just hang'n arround wach'n TV.... I'd like to wear this ______ today... see how that goes, and add bits and pices from there

[Cynthia Anne]

I really beleive she will let you know when it's time! Main thing don't rush her! Let her breathe on her own! If and when the time is right you will know! In the meantime enjoy what you two have together!

[Anne2345]

Every situation is difrent. Keep an open dialog, but don't force the issue. how do you know where the lie is between keeping it open and forcing it? Only you can your spouse can anser that.

These are wise words which you would do well to heed.

When will you know? You will not, unless you continue open and honest communication with your wife. Follow HER lead, and be absolutely honest with her about yourself when she asks questions. This is still new to her, and the more you can educate her about crossdressing, the more she will understand. Although your wife appears to be accepting of you, she is undoubtedly confused, as well. Push too hard too fast, and you risk alienating her. Let her set the boundaries, and allow her time to become comfortable with your crossdressing. When you are confident she is comfortable, a few gentle nudges here and there for more are not unreasonable, as long as you are always mindful of her needs and emotions. Aside from being 27 years into your marriage before she found out, it sounds like you are off to a good start. I wish you well!

[Lorileah]

I would say try transitioning into culottes or shorts that resemble skirts. See if she is opposed to this or if she would accept that look. It is always easy to take a few extra moments at the clothing store to admire this type of clothing, maybe even on the sale rack so you have that as an in (as in gee look! it is only 4.99). You already wear sports bras so adding a skort would not be a huge leap either. Communication is key here, don't just jump in but talk about how these items of clothing fit into your life.

[Barbra P]

I’m just a bit surprised that she is comfortable with you sleeping in lingerie with her. My Wife isn’t real comfortable with my dressing but tolerates it to a certain degree, but she’d have a real problem if I climbed into bed wearing lingerie . . . make that, I’d have a real problem. She wants to go to bed with the man she married and doesn’t want to be made to feel like a Lesbian.

[kendra_gurl]

I wear bikini panties 24/7, sleep in nighty's, wear sport bras when I'm working out, lounge around the house in women's yoga shorts, and keep my toenails painted. She does the laundry, so she sees it all.


. I sleep with her, so she sees me in a nighty every night. I would love to be able to dress in the evening while relaxing, but I do not want to push her too far. How do I know when she is ready?

Think about what your are doing. Does she ever get to see you as the Husband she married? The total Male you?

How about talking with her about it and coming to an understanding of a once a week total dressup and the rest of the time nothing feminine at all?

Personally my wife knows and accepts me fully en-femme (makeup and wig) and we go out togeather and enjoy ourselves because I can become her girlfriend not her manley husband in panties and a nightie.

So many here love to underdress at times and that's not a bad thing until it starts getting to be 24/7 with a wife who receives no pleasure from having to see it.

Talk to her about it and then show some respect for her feelings

As she only discovered your stach in April it seems you have really rushed her already by what your doing 24/7

[kimdl93]

She does seem pretty tolerant. Perhaps she's fears that seeing you in a dress or skirt will change her the way she perceives you, or that its a step towards wanting to go full time. Without pressing the issue of the skirt, I think it would be good to have a continuing conversation about her attitudes and concerns. Otherwise, you're dealing with too many unknowns.

[Eryn]

The only thing consistent about our spouses is that they are all different! Sometimes they have specific things that they don't want to see and these things vary widely from individual to individual. It's not rational, but neither is CDing!

I don't recommend trying to "sneak up" on wearing skirts through shorts, culottes, etc. Your wife has specifically stated that she doesn't want to see you in a skirt and that should be respected. Sneaking up on things like this will make her feel ignored.

I do recommend that you talk to her and say "I'd really like to be able to wear [garment] when I'm [specific activity]. She really does want you to be happy as long as it is within her personal comfort zone and by this point her zone may have expanded to include the garment you wish to wear. If not, she at least knows what your desire is and she will try to accommodate you in the future.

[Stephanie47]

You'll never really know when she may become more tolerant or less tolerant. After 27 years of marriage, if she had no clue of your cross-dressing desires, she may still be mulling over this new facet in her life. I've seen responses in this site over the years, where an accepting wife has completely done a 180 turn around. Adjusting the boundaries in any relationship is an ongoing process.

Like Barbara P, I'm surprised she does not object to you wearing lingerie to your marital bed. Tolerating some behavior does not equal acceptance let alone active participation.

[prettytoes]

She is a great woman. I have worn panties on and off for years. I used to use the excuse that I liked thongs, and women's were far cheaper than men's. I do not hide any clothing, she sees it all. She got me a skirt hanger so my skirts would be more organized in the closet. She sees my skirts laying about and in the laundry, so she knows I am wearing them. I try to not wear lingerie that is ultra lacy or super feminine. I don not want to cross any lines that she has requested; she is my world and I would never want to lose her. I was planning to dress up for Halloween; I think that will be the first time she will see me in a skirt. Now I just need to figure out which one to wear! haha.
Thanks so much for all the responses. All the input is very much appreciated!

[Karren H]

. She did tell me that she didn't want to see me in a skirt or dress.
.....
. How do I know when she is ready?

Ahhhhh. I'd say based on the fact she told you she didn't want to see you dressed.... she will never be ready! Unless its one of those things like when women say "FINE" which doesn't mean fine it means hell no! If that's the case then she's ready now....