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Aka_Donna
05-20-2023, 11:44 PM
Been putting off this post. Not sure what the title should be as there are many aspects to it.

We finally went off for a 4 day vacation, which ended up being 3 days as I injured my ankle. I had hoped for many first times, but most did not happen.

Good
I was able to walk the dog outside naturally dressed in a skirt and puffy top. Great fun.

Not able to do
--Go out shopping dressed. This was my error. It was a small community, re about 300 pop, and rural, so women were not dressed nicely but frumpy best dress was moderate jeans and bland top. Well my business casual with only skirts and a couple dresses would stick out like flashing blue light. Definitely a no go. Note to self- need to think about what women are most likely to wear.

--Drive dressed. Here again, I didn't think thru where we were traveling thru. Coastal towns of pops between 20 and 200 are not good events for first time out driving. Got to think more.

--Go in hot tub wearing bikini. My error again. It was nice and private, BUT it was just too cold to jump in. Winds were about 15mph with temps in the mid 50's. Not exactly comfortable for bikini wear. Yes the tub was between 100 and 105, but freezing on the way in and out just did not hum, so aborted. Learning event- check not just temps but also wind for any water activities.

--Dress several full days in a row. I was afraid of being rejected so didn't broach ahead of time. My error. On the second day, in the morning I just slapped on the same outfit as the night before. Well that lasted thru breakfast when I was asked to change back. Phooey. Ok, so I pouted and didn't dress for over 24 hrs. A waste, yes, but it is what it is. Finally a few days after back, I asked why asked to change back. I expected a comment about a problem with cross dressing. Well, there was an issue, but anything close to my fears. The issue boiled down not to dislikes of crossdressing, but dislikes of LAZY crossdressing. Really the same outfit so often, you have more you could have worn.

So I need to up my game. No longer just lazy out with studs, but change earrings with each outfit change. No longer just a blend lipstick, but also ones that shine and are bolder. And especially do not wear the same outfit two times in a row. Plan better and have multiple outfits. While at it, have at least two wigs. One fun and one that looks good. Oh, and take some time with makeup, just slapping on a tad of lipstick does not cut it.

It will be an interesting rest of the year. Has anyone here had to up their dressing game? If so, any recommendations?

Yes, a book long post for me who usually is very short and cryptic, but much to share with the group. Thank you for reading and looking forward to seeing your comments.

bridget thronton
05-21-2023, 02:36 AM
You managed to do a couple of things - well done. Keep talking to your wife and see if she has ideas on what you could wear that would make her more comfortable when out with you dressed

EmilyShy
05-21-2023, 03:01 AM
This an awesome post. I have thought about a few days away dressed. Not take any make attire with me lol, but the problems you encountered are things that I had thought about but obviously not long and enough.

Might be a good idea to do a male dressed trial run to check out some of the problems you encountered 😀

Good on you for giving it a go and amazing your SO was on board to give good help

Jolene Robertson
05-21-2023, 03:34 AM
Hi Donna,

Sounds like a success to me. It's one of the things we have to learn is dressing to blend in with the women who are out. I know we want to be as fem as possible but when we look out of place we draw attention.

Sounds like a great trip and you have an amazing wife.

Helen_Highwater
05-21-2023, 03:51 AM
Donna,

PPPPP; Proper Plannng Prevents Poor Performance.

I know some will say just go with it but for certainly my early outings I had a plan, well researched and realistic. Day wear is different to evening wear, same for makeup. I'm not one to trowel it on but there's a minimum needed to camouflage our maleness.

As you point out, what you had in clothing was out of place for the location. Not over dressing is one of the skills learned if blending in and moving around in plain sight is your aim.

When I'm fortunate enough to have time to be Helen for a week I never come home without several items of clothing that I took but didn't wear. Simple things like a change in the weather can dictate what you wear on any given day. And isn't part of the enjoyment being able to wear different items from your wardrobe?

So OK things didn't go as well as hoped but we learn from our mistakes and next time things should go more smoothly. Also given your wife is on board why not ask her what outfits you should take and as importantly what to leave in the wardrobe.

Di
05-21-2023, 07:19 AM
No worries rookie mistakes and I appreciate you helping others by sharing.
Overpack for any circumstance that could pop up like the ones you described.
Kudos to your wife being honest and asking you to change as that shows she cares .
Please do not take this as a put down - just so others can learn- ( you know as you posted it )
Do not pout when things do not go to the idea you have in your mind/ so many times I have heard wives say they are going to act like a big baby so why bother even to entertain the cross dressing?
I know you are kind and caring and probably already did this say I did not plan and was mad at myself so sorry for acting like this.
Again this is for the people reading learning -So many wifes give up trying to incorporate the dressing when there still is angst anyways making it no fun and too stressful .We have read ( over the years ) the CDs say on here she was fine with the dressing and then she was not THEN and we hear from the wives - I tried but they act like a jerk either way so I just am not having it in my life .
My advice pack like I do lol any kinda circumstance lol I am ready.
Again thanks for helping others and think of it as a learning experience.
Now plan for next time - that can be fun too.

Think of all you learned, nothing bad happened, you have a wife that wants you to be happy, you were together on a trip, you are helping others . Win , Win , Win Win

Maid_Marion
05-21-2023, 07:40 AM
I recently retired but just got a jury summons in the mail, so I may have an opportunity to wear my business casual clothes that I would wear in the office.
Perhaps a stretchy white blouse with a knee length skirt and tights.
Last time I wore boy clothes that were too big for me. Now I have nicely fitted clothes to wear.

I think Jury Duty standards have become relaxed because blue collar workers may not have business casual clothes. They can wear their nicest jeans.

Consider wearing a wrap over that bikini on your way in and out.

Diane P
05-21-2023, 11:52 AM
Donna a lot of things didn't go the way you hoped but a lot did. Consider it a learning experience. Glad to hear that you have such a supportive wife that she had no problem going on vacation with you dressing feminine. As others have said the best thing to do is research where you plan on going and over pack your feminine wear. I take it you went out along Pacific Coast Highway, which if I remember right is a beautiful drive.

ShelbyDawn
05-21-2023, 12:00 PM
Celebrate your victories first. Then look at your plan and see what you can improve on next time.
Remember the old adage about the trip of a thousand miles beginning with a single step? well, every step on that journey counts as a victory...

docrobbysherry
05-21-2023, 01:40 PM
Donna, I can relate to some of your post. I'm a very lazy guy. But, I'm ions past your stage of simply throwing on a few things so I can say I dressed!:devil:

Sherry demands that I dress to the 9's and make her look good or fogedaboud dressing all together!:doh:

To that end, when I go to a T event out of town, like the week long WildSide event in Vegas this week, I have to start planning a month ahead. While I put together a dozen or more very different outfits. I complete dress rehearsals with each one down to the smallest detail in advance. Then, I package that outfit separately. Otherwise, I end up in Vegas with the wig, belt, or ear rings I need left at home!:doh:

That is so much work for a lazy guy Ive been so busy I couldn't even think about doing it this year!:sad: