Oh to be Girlfriends.

[Gabby6790]

So the SO went shopping with her real friend last weekend. I was of course jealous and would love so much to go shopping for fem things for both of us but oh well. When SO got home she showed me all the things she got and there was one more she didn't show from Bare Essentials. I played dumb [In my head: Oh I could use so many things from there] "what's in that bag?". She says "Just a few things I really needed some new makup". [IMH: You and me both sister] So, I left it alone until today.

When I got home I noticed she had been working on her makeup right away. Eyeliner was super dark and bold. I waited a minute and said something. She responded that she was trying to get better with eyeliner and watched some videos on youtube [IMH: Seriously? Which ones? I think you needed to smudge that after you put it on.] I responded with such a CD in the closet answer "You should let me try it on you sometime". Ugh, sometimes I simply can't help dropping the hints. (uncomfortable pause between us)..... I mentioned she should try a makeover [IMH: We could both go!!!!].

Some day hopefully I will get there with her. I was thinking about telling her she should practice on me but that might be a little much with the recent changes she has been okay with (chest shaving, painted toes).

[Robin414]

LOL, nice post Gabby, made me chuckle (and I don't chuckle! 😠 ) 😉

[pamela7]

and i thought women were intuitive creatures - are you sure she's simply not just teasing you, and she knows?!

[Erika Lyne]

I wonder if Pamela is right. That "...uncomfortable pause between..." you may have been her realization. She may not want to ask because 1)she may fear the answer or 2) she may not wish to offend you.

If you are in the US, this is the best time of year to experiment. It is Halloween in 14 days. It is a BIG deal here, more than anywhere else in the world. It is up to you but this just may be the chance to come out to her. You could be pleasantly surprised of the acceptance level. Only you know if she may be up for it, even if it just ends up being an annual event. Just a thought.
-Erika

[Krisi]

If she knows you paint your toes (I'm assuming the nails), I would think the cat is already out of the bag. If not, at least you have a start. Get yourself a couple pairs of panties and see what she says. Nothing too girly, plain black or nude. If she accepts that, buy yourself an Ahh Bra. Keep adding things slowly as long as she doesn't object.

Back to the "girlfriends" part, it is my hope that someday my wife will agree to go out in public with Krisi as her girlfriend. Another city where we're unlikely to be recognized. A day or two walking the streets and parks, shopping and perhaps dining together.

[Demi88]

Yes Pamela, women are intuitive creatures. Yes Krisi, the cat is out of the bag. I think she knows but is more comfortable living in de nile. Would be nice if the mood was right to have an open talk about what level of dressing she could accept. Perhaps get feedback with each level of dressing. Maybe she is nervous it will balloon out of control if she admits she knows.

[mechamoose]

My wife goes to me for fashion advice. I'm sorry that you may not have that room with your mate. I'm just sharing that it WORKS.

I'm more girly than my girl is. She is/was a tomboy. Goddess, I HATE her taste in shoes.

- MM

[Jenniferathome]

Gabby, you can not hint your way to her understanding. She is not thinking, "Maybe he's a cross dresser." Instead she's thinking that you're just a little weird. "Cross dressing" is not in her lexicon. If you want her to know, you have to come out and tell her.

[heatherdress]

Gabby - While I sympathized with your thoughts, and find them amusing, I couldn't help but feel your comments might have the opposite effect and perhaps be offensive to her. If she was trying a bolder look with her eyeliner, maybe you should have complimented her and encouraged her to try new looks. It seems like you were telling her you did not like what she was doing and that you could even do it better. I would not like to hear your comments if I were her. Showing interest in her appearance is always good but expressing criticism is usually not good. And then to suggest that she have a makeover might imply that she does not look good, that she can't apply her own makeup, or that she can't figure out her own fashion style.

If you can confide in her and tell her of your own crossdressing, your comments to her might be different, but until she knows, maybe you should be a bit more sensitive and approach your interest in her makeup more complimentary. I also would not advise using critical comments about her makeup, dress or clothing to drop hints and arouse suspicions about your own "expertise".

The hints you are dropping will eventually add up but she might be more offended, resentful or resistant to acceptance than if you told her directly, sensitively and sooner.

[Tracii G]

Gabby you need to work on the hint skills LOL.
I think you have gotten some good advice so far so pick your words wisely.

[Gabby6790]

Thanks for all the responses and advice. First off, although it might not sound like it but I wasn't overtly rude about it. Also, she brought up the idea of "getting some help with her makeup" when I suggested the makeover.

Once again, I get that hinting to acceptance isn't a good thing but it is a little difficult to consider screwing up a 20 year relationship when you have only truly accepted yourself a few months ago.

- - - Updated - - -


My wife goes to me for fashion advice. I'm sorry that you may not have that room with your mate. I'm just sharing that it WORKS.

I'm more girly than my girl is. She is/was a tomboy. Goddess, I HATE her taste in shoes.

- MM

This is another one of my issues and was going to be the topic of one of my future posts. I am super more girly on the inside than my SO.

[Charlyne]

When she is practicing her makeup; you could say "Try the make up on me, that would be fun". That's a way to break the ice without actually having to come out.

[Gabby6790]

Charlyne,
I thought about that and might do it. I was thinking of going with the "maybe you could practice on me".

BTW, thanks to all of your complements I made sure to compliment her on her eye makeup as she got ready to go out tonight and I think it was greatly appreciated.

See CDing DOES make you a better SO!!!

[Jenniferathome]

。。。 I was thinking of going with the "maybe you could practice on me"....

This is a terrible idea. If bad ideas were people, this would be China. It's that bad. She will not connect any dots because there are none to connect. You could speak Finnish to her and it would make equal sense.

Look, you are trying to make her guess that you are a cross dresser. She won't. If you want to come out, do that. It's honest and you get to do it on your terms. Anything short of that is wishful thinking.

[Dana44]

I have to agree with Jeniffer. It would be best to sit down and have a talk with her and tell her outright. She may be confused but accepting. But doing it this way will get her more confused.

[BLUE ORCHID]

Hi Gabby, That sounds like a story that I might've wrote .:daydreaming:

[Gabby6790]

I have thought a lot about this response and have decided to take the ladylike approach (It may not seem like it but trust me it is).


This is a terrible idea. If bad ideas were people, this would be China. It's that bad. She will not connect any dots because there are none to connect. You could speak Finnish to her and it would make equal sense.

I get it. As I have said before, a number of times, I know I will not be able to hint myself to acceptance.


Look, you are trying to make her guess that you are a cross dresser.

How do you know what I am trying to do? I actually have no misconceptions that she has guessed that I am a CD. I am simply exploring this side of me and hoping that she is a little bit accepting of some of these changes.


If you want to come out, do that. It's honest and you get to do it on your terms.
Saying that is a lot easier than doing it. I would appreciate accepting the fact that I might know my 20 year plus relationship a little better than you. I also know that I haven't been begun to understand where I am at with all this. I will, most likely, come out to my SO but I will do on my own terms (as you said). Until then, I will push some boundaries because I feel the need to explore this side of me.


Anything short of that is wishful thinking.
I there something wrong with wishful thinking. Yep, I wish that my SO would suddenly say to me "Hey you painted your toenails. Does that mean you are CD? If it does, let's go shopping together, practice doing our makeup on each other and then go out as girlfriends to a club." I get it. That isn't going to happen.

So, you don't have to respond to my post warning of the evils of hinting to acceptance. Your point is taken.

[Amy Lynn3]

Gabby, hints do work. I live alone and love yard sales. I bought a box of old clothing to use as rags in my workshop. My grown daughter came by for a visit and saw a feminine looking tank top in the box of cloths. As she went out the door she said "Dad are you getting into crossdressing"? She was out the door and gone, before I knew what had just took place.

My point is.... she picked up on the hint, that I never hinted. To me that top was just a rag....not my taste.

[lexi0922]

My bf and I go shopping together. He looks like his manself...and I look like me lol. But we go shopping for him a lot..I asked once he gets more comfortable in CD form if we can go out like that... 😁

Today we're even wearing matching panties. It's exciting.

[Demi88]

Gabby,
Color me confused. Is it possible that SO doesn't already suspect a feminine side since she knows about your toenail polish? Is polish clear?

[Gabby6790]

My bf and I go shopping together. He looks like his manself...and I look like me lol. But we go shopping for him a lot..I asked once he gets more comfortable in CD form if we can go out like that... 😁

Today we're even wearing matching panties. It's exciting.

Oh Lexi, can you call my SO for me and try and explain to her how wonderful it can be?? :D


Demi,
My toenails are painted a dark plum. She certainly could have an idea. Or should could have know idea. Or she could think I just have some weird tendencies. No way of knowing for sure unless I ask her of course.

[lexi0922]

@gabby I wish I could!! We're out heel shopping for him...and combat boot shopping for me lol