Missed Opportunity?

[Andrea Chenowith]

I've always known that my crossdressing was driven by a desire to fulfill a fantasy of sorts, in that my femme self is a projection. As "she" does all of the things to get ready, I imagine "her" doing them to impress/satisfy me. My entire wardrobe is comprised of the things that I want to see worn by my partner. Even when I’ve ventured outside, it’s always been in that mindset.

Recently, though, I've found myself wondering whether there might be more to it, or whether my interest has grown. Some of the best memories I've had while dressing center around sales associates that have expressed an interest - whether real or feigned - in my dressed self. About six months ago, I was even nearly tempted into cheating on my wife, based on the interaction between myself and a SA on a shopping trip. (It's not normal for the SA to brush her hands intentionally over your buttocks after helping zip the dress you're trying on, is it? :D)

So to the opportunity as mentioned --
My wife was invited to a wedding, and based on the venue and the time, we couldn't all go. She went, while I stayed home with our 3-year-old. But as she was picking out her outfit the night before, she complained about not having a strapless bra that fit. As we tried to find another bra that would work with the straps of the dress she'd chosen, all that was running through my mind was that I had a bra in my wardrobe that would fit her perfectly. (We're the same size, although I've got her beat by about eight inches in height.)

She knows that I wear panties daily. I've been caught buying other things occasionally, which she was somewhat disapproving of. The disapproval was more from a money standpoint; she's never really offered an indication of where she sits on the spectrum of approval. I've also offered her style tips on the side that would normally tip someone off (at least in my mind) that I'm more into that than the typical male; but my background in photography can also explain that.

In many ways, this was a missed opportunity, but I’m not sure that I am in the best place to have taken this chance at this moment.

[Jaylyn]

I really think you have play it by ear and just use the right time and place to be upfront. Don't tell them when they are stressed out about something, or have had a hard day. I made sure my girlfriend / later wife knew I loved seeing her in all the latest styles and kept reminding her of what I would love to see her in. I made sure her nails were done, that she had her hair done, and that she look hot and sexy all the while her still being the love of my life. I knew I wanted her to be my SO long before she really knew it. I fell hard for her and she began to realize we were soul mates. We have never looked back. We have had some disagreements but have always promised to never go to bed mad at each other. For 49 years this has worked. We have tried every sexual adventure one can imagine as we grew up during the "Hippy Age". We are still in love to this day. Every kink she has had we have tried and she has helped me with every business adventure, career changes, and my crazy adventures over and over. She knew I loved her in sexy short skirts, and low cut tops. Lots of make- up and also she knows i was a very God fearing guy that would be in Church every Sunday. She dressed like a church lady on Sunday. We still at the ripe old age of mid sixties we are still adventure minded and still a prominent part of the community. She knew I loved dressing early in our relationship and she thought it was a kink I'd grow out of. She now knows that Jaylyn is a real member of our relationship. I did promise her I would keep it between just she and I and she accepted that and even helps me. I have really felt the urge to go beyond that and meet other CDs but I have been faithful as I feel we all should.
Now with all this said your missed opportunity can only happen when the time is right and you will know it when it is. Don't rush into something it will come in its own due time. I read many stories on here of broken marriages, I can say it is much easier to dress and enjoy it with the one you love. They are your rock and have your back. Keep this in mind don't rock a boat till the time is right and you are in shallow water where you both can wade ashore and the marriage can escape unharmed. Wait till you are sure and the moment is right.

[DonnaT]

If she doesn't know about your bras, then not mentioning them at a time she's stressing out over clothes was a good choice.

[carhill2mn]

Donna got her reply posted before mine but the message is the same; this was not the right time to for her to learn about your bras.

[Beverley Sims]

When you have a moment like this it is better to let it go unless you are asked.

[Maria 60]

A few months back we were going to a family function and she was putting on her second pair of pantyhose, the first one a hole in the toe the second a run up the pack as she was pulling them up. She doesn't wear pantyhose very often so now she was pissed off and asking were she was going to get another pair of beige control top pantyhose now, knowing I never wear beige and I don't wear control top, but a while back I was in Walmart and there was a clearance of pantyhose and I picked up a few pairs, and not wanting her to believe that I bought something fem without her, I didn't mention it. Well at that moment I told her I think you bought me a few pairs of those a few months ago, I dug in my closet and sure enough there they were. I handed them to her and she said she didn't remember buying this type, she gave me a ten second straight in the eye look, but I believe she was more happy that she got herself the pantyhose and it ended like that. During the party she even told me how nice they were and if I remembered were we bought them. You just don't know how to play it at times.

[Marcelle]

Hi Andrea. I believe it was not a lost opportunity as others have said surprising your SO with "Hey I have a bra that might fit" while she is preparing for a day out would not have been a wise choice unless you are at a point where your relationship is comfortable with such discussions. You indicate that she knows you wear panties and have bought other items and from your post I don't get the feeling she approves. If you truly want to find out since she probably suspects, you might want to pick a time and sit down for a conversation to see how much she knows (obviously she knows about the panties) / suspects and go from there.

Hugs

Isha

[Teresa]

Andrea,
I agree with the replies so far the hidden bras stayed hidden right choice, the only missed opportunity would have been your wife having a go at you and spoiling her day !
I understand your feeling about kind SAs ! It took me a couple of weeks to get over a kind SA when buying some shoes ! I came close to buying her some flowers and possibly asking her out !
Can't say I had the same feeling when a male SA zipped me up a PVC dress in a rather dubious shop, especially when I saw what he was wearing in the free catalogue he pushed in my hand as I left !!!

[BLUE ORCHID]

Hi Andrea, I think that you have chosen the lesser of two evils.

[Katey888]

Andrea,
As I read through your post I was rather getting the collywobbles as to what missed opportunity we were talking about... ;) Beware of friendly SAs... most of them are largely just after their next sale and it's their job to make you feel good... I don't think you should consider a sisterly buttock graze cheating... just flirting, perhaps... :thinking:

Sounds like you did the right thing by keeping quiet... a position of 'disapproving' doesn't sound like you'd be guaranteed to get a positive reception to a wardrobe laden with more girly stuff than she knows about. It does surprise me that you haven't talked about it more, but I'm definitely not one to start that debate.. :)

And as for Teresa's shopping recommendations...

Can't say I had the same feeling when a male SA zipped me up a PVC dress in a rather dubious shop, especially when I saw what he was wearing in the free catalogue he pushed in my hand as I left !!!
I think you should just be grateful that was all he pushed into your hand, dear... ;)

Time and place, Andrea - and this probably wasn't it...

Katey x

[Andrea Chenowith]

Thanks to all for the replies! I'm still trying to sort out how much of (or even if there has been) a change in my reasons for dressing will play into any future activities.

We have recently moved and are in the process of preparing our old house to go on the market, which is forcing me to reevaluate my setup. In our old place, we each had our own closet in different rooms (hers in our bedroom, me in a converted office) so it was easy to hide the day-to-day stuff there and my full wardrobe had a nice spot in our attic. In our new townhouse, we share a much larger closet, so there's not really a spot to hide. That's offset by the fact that we have a storage unit just across the street, but I am still having to evaluate what exactly I'm going to keep and what I'm going to donate.


You indicate that she knows you wear panties and have bought other items and from your post I don't get the feeling she approves.

Here's the thing about that. She has mentioned going to drag shows in the past in a positive fashion. She's also caught me in the past, but before I was really ready to open up about any of it and gave the impression of not minding if it's something that I do. The more recent comments have been primarily in regard to our financial situation - despite it being a splurge buy and return - and didn't have anything to do with opposition to the dressing.

Again, I know that this certainly wasn't the right time for the conversation, but there's hope for the future.

[Teresa]

Katey he did push something else in my hand ..... ! A free pair of stockings to go with my purchases !!

[stefan37]

A couple of years ago my daughter was going to a part and was out of mascara. My son said " go ask dad, he has some".

[Wildaboutheels]

Missed opportunity? Hardly, IMO based on your post.

You are in a DADT and your wife simply "tolerates" your dressing.

She doesn't seem to have much of a problem with your painted toes...

But she seems to be happy to look the other way as far as the rest of it.