Interesting Evening Playing With Makeup

My SO does not know that I cross-dress, however from time to time I do drop hints. The other day she stopped at Ulta to pick up some eye cream. When she got home, I asked her if she got her stuff. She said yes, to which I replied, "Did you remember to pick up the eye shadow I asked for?" Her reply was "Stay here I be right back." She came back into the room carrying a hand full of her makeup. She said you asked for it; now you are going to get it. She proceeded to do my face completely. As she was doing it she kept saying things like you have great eyes and perfect lips. When she finished, I went to the bathroom to check out her handiwork. It was awesome. She came in and we talked about her technique(much better than I have ever done) and the colors she used. She said "you are enjoying this aren't you?" I said yes, then she asked the most interesting question of the evening. She said "If I do this again, would you go out with it on?" My reply was "well it depends." She said on what? My reply, "I would have to be dressed completely as a woman." She said we can work on that. I said, you would have to help me pick out clothes and things. She said "if you want to we can." That was the end of the conversation for the evening. My plan is next time we go shopping together to ask her if she wants to take me shopping to get ready for our girly outing.

Well Jamie,your hint dropping technique paid off and I'm really glad for you that you have an SO who accepts all this. I guess 3 out of 4 ain't bad but 4 out of 4 is excellent.


Samantha

For someone who doesn,t know, your S.O. seems to have a pretty good idea that you could be a crossdresser :D

Ha ha, your SO does not know? She has known all along I would venture, and decided that it was time to bring it out into the open, Good for her! And you are very lucky.

a blind man can tell she knows!!! :tongueout : why not fess up while you still can :hugs: good luck

Jamie, A. She absolutely knows, has known, has been waiting for you.
B. You are one very lucky gal!
C. You need to give that wife of yours the best evenig she has ever had.
D. Did I say you are one very lucky gal?

If she truly does not know, then look out, she is up to something evil.

Well she knows now hun. go slow you don't want to spook her you luck girl.:hugs:
Angie

Well there is knowing and then there is being for sure and one thing I know for sure is you definately need to keep communicating with her. If you do go shopping for you, make sure that she gets things for her as well and I do believe some flowers from "him" are in order as well.

I have been slowly easing my girlfriend of a longtime into the idea with small casually placed hints here and there.

One night she said she wanted to see what i would look like with make-up on and i casually just said oh "i usually do all that stuff on the weekends"...youll have to come back then

and ill make fun of her telling her she cant walk in heels...even though she can and she'll say i'd like to see you walk in heels and i will...but i feel like im not getting anywhere.... i pulled a stunt 1 time and ran at her with a thong and she thought it was halarious but later wore it again and she seemed bothered by it....anybody else place hints like these here or there....everytime im ready to tell her something comes up and the timing is just never right.

Quote:

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Originally Posted by jamiecd636

She said "If I do this again, would you go out with it on?"

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There is an old saying: "You can lead a horse to water, but you can't make it drink." I think the water just walked up to the horse.!!

Be nice to her. Very, very nice.

Wish my SO was that open minded about it, your very lucky.
Does your SO have a sister by chance? lol - JK

Lucky. Fortunate. Blessed. Prosperous. Favourable.

What I would do to be in your position.