29th

[Jess6887]

I have decided to tell my Gf on the 29th of April that I like to wear womens clothing, and that I like to wear nightgowns to bed, I am very nervous about doing this and would like some assistance from you girls to help on some different ways on doing it,
What questions should I expect, how should I say it,

Please I need this to go well as I love her very much,
She will be the first person I have ever told about this side of me,

[Beverley Sims]

I would say you like to wear satin PJ's because cotton binds to your body when in bed.
She would understand this and you could add that satin nighties give a lot of freedom too.
This would be plausible and close to the truth, then you could test the waters on her reaction.

[BLUE ORCHID]

Hi Jess, What's so special about the 29th ??

[Jess6887]

Thanks for the advice, I just want to do it on that date as I am traveling for the next 2 weeks

[Jenniferathome]

Why wait? but...

She will ask you if you are gay and if you want a sex change. You can NOT be offended by any question. She will not have the background to even comprehend your confession, don't expect her to understand nor to be interested. Imagine if she came to you and said, "Hey, I switched brand of tampons." You'd have zero reference and no interest. In fact, you'd probably prefer to un-hear it. Now, if there was an analogy, add to this a level of shock unprecedented in your lifetime. THAT'S what will be hitting her. All you can do is invite questions and promise to answer all of them honestly. She will likely ask questions to which you do not know the answer, answer the best of you ability. never go on the defensive. You are inflicting something on her for which no woman is prepared. In my signature is what I said to my wife when I came out.

Good luck and you are doing the right thing

[linda allen]

Rather than an arbitrary date, I would just wait until the time seems right to tell her.

As far as how to tell her, there are many ways and you need to find a way that works best for both of you.

[Jess6887]

Thanks everyone for your help, I am very nervous about doing this, but she is a loving and caring women

[PaulaQ]

How long have the two of you been together? Will she feel deceived? (This depends on your situation, obviously.) If so, apologize for that.

Explain, as best you can, your feelings - for example, you are secretive about this because you are ashamed, or afraid of stigma, etc. (If those are the case.)
I'd tell her that you are telling her this because your feelings for her are serious, and because you trust her - make sure you say you've never told anyone before. But tell her she needs to know because that is only fair, many would judge this and find you wanting.
Make sure you tell her:
- you aren't gay
- you don't want a sex change (unless you think you do)
- you are still a guy (unless that isn't how you feel)
- this isn't (or is) a sex thing for you, but part of your identity (or not)
- whether or not you've done this., felt this way since you were a kid

There's no real way you can guess her response. It can vary from "and? So what?" to "that's cute!" to shock, or even revulsion.

Her first reaction isn't necessarily her long term one either.

Knowing a little more about you both would help.

[NicoleScott]

Once you decide to tell, you need to tell all. I don't agree with Beverley's advice to say cotton binds to your body when in bed. Your GF might go out and buy you some satin men's pajamas. Oops, problem not solved. Answer your GF's questions honestly. If you want a sex change, now's the time to say so. As best you can, let her know your goals, like going out en femme, etc. If you can, don't be apologetic or defensive about your revelation. Be matter-of fact, no big deal, just like to wear feminine things to bed, if that's all there is to it.

[Jess6887]

I have written a letter explaining all, ill be there while she reads it, and I have attached questions to it that may have been thought of

[Jennifer Marie P.]

Start it off slow and see how she takes it.