Testing the water. (Long one, sorry)....

[heathr1]

I keep in touch with a GG I used to work with and see her for a coffee once a month or so.

Although about 7yrs older than I and married with grown up children, she used to jokingly tease me about sex and jokingly flirt with me.

During my illness with stress she was also extremely supportive and I do trust her with things I cannot trust others with and she knows it!

Recently I texted her to arrange a coffee meeting and she accepted and asked me to phone/speak with her. I phoned and she explained she was in the dept. store buying make-up and lingerie.

I then mentioned that for a laugh my ex-girlfriend painted my nails (to see what her reaction would be) and I liked it, but did not mention that it was a full make-over.

She did not make much of a comment, just a tiny 'huh' laugh as if to say she is not shocked, I guess.

I also told her I was in a leatherwear store (which I was) and saw a nice skirt that may suit another GG I know.

She simply gave a short quiet laugh again and said 'Ah, okay'.

As she is a bit of a laugh/tease and in the past has initiated herself plucking my eyebrows and cutting long ones on several occasions, talking to me about her hairdos and new boots etc. I was half hoping she'd reassure me she understood me liking make-up or even better still offering to paint my nails.

Once in a pub, she showed me a mobile/cell phone photo of her breasts.

Would you say I've tested the water enough for me to tell her and confide in her about my dressing?

I honestly feel she would be okay about it and would not judge me.

[Marla GG]

Hmmm :thinking:

In my opinion, "testing the water" with hints and such is not usually a good way to gauge what someone's reaction is going to be. The hints you dropped (that you had your nails painted once, and that you were in a leatherwear store) were pretty vague anyway, and I seriously doubt that she would connect those things with crossdressing -- if she even knows what crosdressing is. Her responses seemed kind of hard to read too, if you ask me.

I would base my decision to tell her, or not, on the quality of your friendship alone. If she likes you and cares about you, there is a good chance she'll be okay with it. If she isn't very invested in the friendship, then she might find it easier to walk away than to make the effort to understand. At any rate, I wouldn't read too much into her 'huh' and 'Ah, okay' responses, one way or the other.

Marla xx

[Rachel M]

I think you answered you own question about telling her you dress. You said you could "trust" her with things you could not tell others. I think you would be alright by telling her you enjoy dressing every now and then.