Trying to figure out the best way...

...to approach my wife.

The 1st of October there will be a Pride event about 25 miles away from our home. It will be at a public park. Heather plans to be there. The things I need to speak with my wife about, in no particular order are:

1. The fact I plan to attend. I don't see her having an issue with that.

2. I plan to attend fully dressed. I expect her to ask if I really want to do that. The answer is yes as I hope to find other crossdressers I can network with as a support group.

3. I would like her to accompany me, but I don't believe that is a good idea. If there would be anyone we know in the vicinity, a cursory glance at me may not get their attention. If they saw her, there is no way to avoid them knowing I CD. I know she doesn't want that. BTW, the odds of seeing anyone we know would be extremely thin unless they are there to participate in the events in which case I believe keeping each other's attendance in confidence would be the order of the day as we, to the best of our knowledge, know nobody that is a part of the area LGBTQ community.

4. I would like to drive her car which is non distinguishable from many others on the road. My car is extremely recognizable and if anyone we know were to see me get in or out of it, they would know I CD.

5. I am going to order a wig which will be delivered to our house, and she just needs to be aware if she retrieves the package from the front porch. I cannot order this wig from Amazon so cannot use a locker.

6. While I will leave the house partially dressed en femme, the part visible thru the car windows (top) will be drab so our neighbors won't suspect anything. Once away from the neighborhood, I can put forms in, remove golf shirt, and put on the top.

7. I will want to put on makeup except for lipstick which I can put on when I change my top and put the wig on.

8. I want to ask her if she would be willing to help me with the makeup. This will be the most difficult ask as she has previously said she doesn't care to see me with makeup on. If she passes on this, that's fine. If she agrees to help, that will be a huge step.

My son and grandson are coming for a short visit next Wednesday thru Friday. I'm going to wait until after they have left to broach this topic with my wife. Basically, I have a week to put together a plan. I need to have this conversation in time to order the wig and give her time to consider what I'm asking (using her car and helping with makeup). I don't want her to feel she's being rushed to make a decision. Any, and all, input is welcome. The collective experiences of this group seem to end up being very valuable when contemplating crossing new waters.

There are several issues here, all related, and all can be solved one way or another by full disclosure. I know you are out with your wife so there is no need to sneak around -thankfully!. It looks like you will be entering into some new areas with this trip, so the only way to know if you are crossing over any boundaries you are not aware of is by disclosing all and everything you intend in an upfront manner, as you have here. If she disagrees with anything, you'll know right away, there will be no secrets. If all goes well you'll be able to go to your event with a clear mind and enjoy it thoroughly. If you stumble across any barriers you'll know that too and be able to deal with them beforehand rather than after, much more effective I think.

I don't really have any good answers to your questions, but I did have ONE thought -

Maybe your wife could accompany you if you could get her to dress in some kind of "disguise" too. It could be anything from a simple mardi-gras mask to going all the way to making her look like a drag queen herself. Maybe you could sell the idea that this way, both of you could "take a vacation" from the humdrum of everyday life, let your hair down (so to speak), and share the adventure.

Just a thought.

Clearly you have put a lot of thought into this. You could bring up your points in a logical and concise manner, as you did here. Tell her you need her help so she feels like an active part of the solution. If you get pushback while being open and honest at least you will know where you stand and can figure out a workaround.

I get the part about if your wife goes people might come up to her.
But people going to a pride event would be accepting ….so maybe a non issue.
Since she knows the wig delivery should not be a worry.
Do what you feel as going partially dressed , we started that way but ended up just not worried about that….
Point being do what you feel best doing.
About the makeup Sher watched YouTube videos and was a professional before we even met , makeup on a cder - neutralizing the male features, shading and contouring plus beard cover.
She will not know these things…you have time to look these up and practice, practice practice.
It will be fun too.
But the most important point I want to get across!
Since she said no before, a common complaint from GGs is the CD pushing the make up on them.

Unless she suggests it ( then it is fun not a chore)
And since she nicked the idea before I would stay away from that .
Go on look up videos and enjoy the experience.

Heather,

I agree with Di. Since your wife already nixed the make-up idea once I would skip that.

The best way is to NOT include your wife.

1. Rent a motel room for the day. Avoids the car issue driving away.

2. As to the car, if someone sees you at a Pride event getting out of your car, is that really a problem? And, similar to #1, just rent a car for the day.

3. As to the wig, find a wig shop that is TG friendly (call around), find one you like, and buy it in person.

4. Call up a makeup store like Ulta, Sephora, Merle Norman, etc, and ask if they do makeovers. If they do, you can either go on the day or go before, take notes, and buy the stuff they use.

The bottom line is you will be at Pride. Nobody will be judging how good your makeup is because there will be people in all forms of dress.

You are overthinking this. Tell your wife you'll be gone for the day to Pride and the outline of what you are planning (or not, up to you). If she wants to volunteer to come or do your makeup, great. If not, proceed with your plans as I suggest.

I?m of two minds. Part of me says leave well enough alone. The other says just as her for what you want. After all the years together it doesn?t seem like too much to ask, but what do I know

There's a lot to unpack there.

Your wife could accompany you with no issues if she wore something that hid her features. Sometimes, a cap and sunglasses are sufficient.

Heather, I can't even begin to give advice. Your wife is so much more I
Understanding than mine. I do understand the delimma and wish you the best. Hope you have an awesome time at the event.
Roxie

Thanks for all the input. My wife really cannot disguise herself as she has mobility issues. Anyone that knows her would recognize the way she walks (looks like a penguin - her words, not mine) due to an injury 45 years ago. I really have no issues letting her know where I'll be going. I just don't want to spend the $$ renting a motel room for dressing and applying makeup. I have thought of putting on basic makeup and then heading (by appointment) to an ULTA for a makeover about 9:30 a,m so I'll look as good as possible for the Pride event. Regardless, I'll need to take the conversation further than just telling her where I'm going so I can leave the house mostly dressed without tipping off the neighbors that I CD and crossing our own boundaries.

With regard to the makeup, I suspect my best plan is to dress as much as I can at home, kiss her good-bye, head to my bathroom to put on my makeup, then yell "good-bye" to her as I leave the house. That way I won't breach the makeup boundary. Telling her what I will be doing gives her the option of offering to help without me asking. I suspect she won't offer and that is fine. Once away from our neighborhood, I can stop to apply lipstick, wig, and femme top.

Sounds too complicated. Just buy a pink tee and a pink ball cap and write I ❤️ To Crossdress. Big oversized fem sun glasses and some lipstick and just go enjoy the event.

After reading many of your posts I figure you and your wife can have this conversation. Prolly not going to be easy but being open and honest with your thoughts should help both of you figure this out. Lots of the advice here from others is value added for recommendations for being safe. Best wishes for a great out come.

Does your wife have any interest in going? If you plan to keep your CDing a secret from everyone else, then she may not want to go.

Since you are going to appear at public event, expect TV cameras, people taking pictures with their phones, all different ways for you to be outed, so I don't think the type of car that you drive will be your biggest concern if you don't want to be outed. Expect to be recognized eventually.

If you want to appear in public, only 25 miles away, I expect someone will know you. It's a small world now. We go to a town 30 miles away for CD and non-CD events and usually see someone from our small town that we live in.

Regarding asking your wife to do your makeup: personally, I tend to use minimal makeup that takes 5 minutes to complete. Most women know their own routine that doesn't always extend to someone else's look. I wouldn't dream of "helping" my hubby with makeup. He spends at least an hour putting make up on. If you want someone else to apply your makeup, maybe book an appointment at Ultra or a similar place before you go. There are also U-tube tutorials.

Finally, maybe easier said than done, but don't overthink it.

Have fun at your event.

You would like your wife to accompany you.
You want to wear makeup, but she doesn't want to see you in makeup.
Pick one.

I guess I didn't explain myself fully. Yes, I would love for my wife to accompany me. However, I also know that wouldn't happen as she would be 100% uncomfortable in that setting with me. We don't always get what we want.

Thanks, Char, for the fact there may well be local news coverage (probably will be). That had never occurred to me. I may need to completely rethink going to this event. I definitely do not want to be outed in such a way that friends could become aware of my CD life.

I've given this event a lot of consideration the past couple of days. I am going to attend fully en femme. I will be extremely cognizant of any cameras and will remain out of range. I believe that while I may not be passable, I also will not be recognizable.

Good for you Heather! I hope you have a very enjoyable day at the event. Be cautious & confident.
Maybe turn down those local TV news people wanting to interview a good looking mature lady. :)

Wish I could be there to accompany you ...

Emily

My wife accompanied me on a trip to the VA (90 minute car ride 1 way). On the way, we stopped at Belk's and Hobby Lobby as she wanted to get a few things. While at Belk's, she was looking for a top. I've not enjoyed browsing the women's clothing section with her like this for a long time. After my appointment, we stopped for lunch before heading home. Once on the road, she read a book for a while and then we started talking about a variety of things. In response to something, she commented that I am often just a silly to understand person. That's the opening I needed. I replied that probably the silliest thing to understand that I do is crossdressing. She agreed. I told her there is a Pride event coming up (gave her date and location) that I'd like to attend. I asked her if she'd have a problem with that. She doesn't.

Then she asked if I was going to dress for it. I told her that I planned to. She said she wasn't interested in going along to which I told her I didn't think she'd want to. I then asked if I could use her car as I thought if there was anybody we knew in the area, getting out of my car would be a dead giveaway as everyone I know, knows my car. She had no problem with that and then said, "What if you're in an accident and you're in drag?" The best I could tell her is that with 61 years of driving, I've NEVER been in an accident so I'm not expecting to be in one now.

After I order the wig, I'll let her know it's on its way.

As the time draws near, I will put her fears of neighbors seeing me leave en femme to rest by explaining how I will only partially dress at home and then finish dressing after I'm out of the area. I've decided I will NOT approach her about assisting me with makeup. The biggest reason is I expect to wear sunglasses and won't concern myself with eyeliner, mascara, and eye shadow, I believe I can handle concealer, foundation, powder, eyebrow pencil, etc. I will put my nails on after leaving the house, as well.

I CAN HARDLY WAIT!!!

Heather, I'm glad the talk with your wife turned out positive. Have a good time.

Sounds great Heather. Looks like you have the green light from your wife to attend. Enjoy.

You say you are going to a "Pride event", yet you don't seem to have a lot of pride yourself. I say that because you seem to be hiding things from your wife and others. If your wife knows that you are a crossdresser, she shouldn't be surprised or upset if you buy a wig. She doesn't have to open the package.

As for her accompanying you or you driving her car, you will have to negotiate these things with her. If the car think bothers you that much, you could rent a car for the day. And for news coverage, hopefully, your presentation is good enough that nobody will recognize you.

Have fun.

Someone else named it Pride - not me. To me, it is a LGBTQ event. The agreement with my wife has always been that I don't cause her any embarrassment. Thus, others that we know will not learn that I CD as she would suffer a great deal of embarrassment. While I CD at home, she is not a fan and doesn't believe any of our family or friends would be, either. I would agree with that assessment. I'm not sure why you think I'm hiding things from my wife. I just measure the amount of info I give her, and when I give it, so as not to overwhelm her. This journey I'm on isn't easy on her. I understand her angst and try to respect her reservations about what I'm doing.

You mentioned ordering a wig and not wanting her to receive the package.

If you are not prepared to be outed by being out in public, don't go. You'll be nervous the whole time and will not enjoy yourself at all. I understand wanting one's spouse to accompany, but it sounds like this would raise risk to an unacceptable level. Again, is the reward worth the potential consequences?
On the other hand... This is a Pride event. It is unlikely that you will encounter anyone you know who would not be pleasantly surprised at meeting this part of you. No?

I guess the lemon here is...and I'm not being judgey since I"m still working through this myself....communication. it's damn hard after forty years of marriage to start communicating real needs and desires. its a process

Quote:

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Originally Posted by Krisi

You mentioned ordering a wig and not wanting her to receive the package.

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From my original post:
5. I am going to order a wig which will be delivered to our house, and she just needs to be aware if she retrieves the package from the front porch. I cannot order this wig from Amazon so cannot use a locker.

I thought I stated she does need to be aware I've ordered it in case she does pick up the package. Maybe I simply don't express myself properly for which I apologize if that is the case.

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Audrey,

I absolutely agree. Our communication has always been pretty decent until this subject presented itself. The issue is I'm willing to talk about this at any, and all, times she wants; but, she simply prefers not to talk about it all that often. I understand her angst. I truly wish there were some way I could get her comfortable talking about her husband dressing in women's clothing. Her take, I believe, is pretty much I'm an adult and can do what I want. By the same token, she is an adult and doesn't have to enjoy what I do and would rather not hear about it. She sees me daily in dresses and lingerie and that's enough for her. She knows when I get something new as I will be wearing it in short order. We have so many things we do together and enjoy together. This just isn't going to be one of those things. What I wish is that I had known I'd have this desire when we first got together 40 years ago and could have told her then. On the flip side of that wish is the fact she probably would have told me "Good-bye" back in those days. While I had tried on bras and pantyhose a few times over the years before I met her, it was a sexual adventure for me as a youth and young adult. I never ever considered going this far into crossdressing. The odd thing is it has no sexual attraction for me now. I simply love the comfort and feel of women's clothing. I'm sure I'm as surprised as she is. The likely difference is I tend not to question my motivations and just accept my life as it unfolds before me. I am not particularly introspective.

Well, all my concern for this coming Saturday was for naught. It seems where I live will be getting a good drenching for the entire weekend as Hurricane Ian passes thru. There is little doubt the event will be cancelled. I will be checking the web site to see if it is rescheduled. And, I love the wig I ordered.

A positive UPDATE: The hurricane has passed thru. Tomorrow is supposed to be sunny and nice. The park where this even is taking place likely had plenty of rain but I suspect no flooding in that area. Fortunately, in this area the ground is more sand than dirt and water soaks thru it rather quickly. My wife asked if I was still planning to go. If I was, she said she would work at raking up the debris that fell from the trees. I told her I was planning to go and then I went out and raked up most of it. There's still a little bit to rake up; but, I'll take care of it late tomorrow or Sunday. The place I was planning to finish dressing at (above the waist) has announced it will be closed tomorrow for storm clean up. Oh well, there are plenty of other places I can go. It will just involve removing a golf shirt and putting on a tunic top. I'll already have a bra on and forms in place. I'll leave the house with makeup on but no lipstick in case a neighbor would see me thru the car window. That's no big deal nor is the wig. All that can be done in any parking lot and not really draw any attention. I just figured the place I was wanting to change at is a huge outdoor garden and I could enjoy a stroll thru a small part of it before taking off.

Quote:

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Originally Posted by Heather76

The agreement with my wife has always been that I don't cause her any embarrassment. Thus, others that we know will not learn that I CD as she would suffer a great deal of embarrassment. While I CD at home, she is not a fan and doesn't believe any of our family or friends would be, either. I would agree with that assessment. I'm not sure why you think I'm hiding things from my wife. I just measure the amount of info I give her, and when I give it, so as not to overwhelm her. This journey I'm on isn't easy on her. I understand her angst and try to respect her reservations about what I'm doing.

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Your statements here seem to accurately reflect my situation. And, I protect that.

First, I appreciate there are some serious considerations you have brought up that I don't want to minimize. I see my self doing much the same level of planning around outings. I really enjoy the anticipation I feel leading up to my adventures. It can keep me in a pink fog for an extended time. I hope it all works out well for you and that you have a great time.
Traci