Wish me Luck!

[Heather W]

I have decided it is time to come out to my mother about my crossdressing. My sister who has known for years has been pushing me to tell her and in my heart I know she is right, still I am scared. I have a good relationship with my mother, not too close but we see each other probably every week or so. She is the only one I am worried about as my father has not been really in my life since he and my mother divorced 15 years ago. I see him only at family weddings and funerals and frankly I could care less what he thinks. Mom is having me and my sister over for dinner tomorrow so I am open to suggestions as what to say. Also should I go dressed or go in drab and see how it goes?

[CharLee]

Heather,

I would suggest you approach the subject lightly with our mother. If she is an open minded person then maybe she will be willing to accept your cross dressing. But I must tell you to be totally honest with her and not hold anything back. If this is important to you, and goes beyond just cross dressing tell her that also. Explain to her that this is a strong compulsion that you have and why it means so much to you. She may not want to see you as a woman, and that you should respect, but let her know that you need to dress but won't do it in her presence unless she asks to see you dressed.

In any event I wish you luck and hope things go the way you want them too.

[Davita]

Heather,
Charlee is right to go easy with Mom. Granted Moms' jobs are to love us but they don't have to like everything we do. BTW, if you are going to try to wait for that perfect moment in a conversation... you will be waiting for years. Just find a nice moment like having coffee or dessert and broach the subject. You could look at your sis and ask her, "is now a good time to tell her?" BUT this means you need to let your sister know in advance what's going on.

Good Luck!

[Deidre Taylor]

Not an easy subject to approach with a parent Heather. Davita is right about going easy and not pushing your femme self on your mother until she is ready. My mother accepted the fact I was a crossdresser when I was quite young, 17 or so. Growing up in a house with just her and 3 older sisters in a way it made things easier she laughed when she finally accepted I was what I was after countless times of being caught. Still when I finally accepted the fact I was transsexual that was a tough conversation to have with her and my sisters. Just be patient and don't push the issue, she will come around in time I am sure.

[Stephanie H]

Shock and awe will only work in military situations. Moms are very understanding, caring and compassionate.
Being that your sister knows and accepts, rehearse a opening dialog that you feel should be taken with her so as to have her support as you get deeper into the conversation with your mother. This way, she will be able to help get over the stumbling block of the conversation. I have the same type of sister. One who knows, seen and has helped many times.
She will be you biggest supporter with mom and mom's reaction will be acceptance being that you have your sisters support.

[Diana Michelle]

Heather I think everyone has said it but it can't b said too much, go easy on your mother. You are pretty much dropping a bombshell here! I have been there and understand how you feel and I pray your family reacts better than mine did, although time has a way of healing wounds. I think the best you can hope for from telling her is she understands what you are. Don't expect loving support right away. After all she raised a son nto a daughter. Just be calm and take any little victory you get.

[Kelly]

Heather,

The advise so far sound solid. The only thing that I can add is my heartfelt hope that all goes well.

Kelly

[Eileen (SO)]

Dear Heather,

Since your sister has known for some time, she should have good insight as to how Mom would be accepting. Were there any events during childhood in which you were caught 'experimenting'? That should be a good way to broach the subject.
I would suggest to only open up only as much as she wants to know. Too much information at one time can be overwhelming. She will ask more questions when she wants to know more it may be that night, or a month from then. Maybe never.
Do not go dressed! Go as the son she knows.
Good Luck!

Eileen

[Anita]

Dear Heather--
I also wish you the best in carrying out this decision. Don't be surprised if your mother does not bring up the subject for months afterward, or never does. That is part of some people's acceptance.

[Heather W]

First I would like to thank all of you for your advice and words of encouragement. It means a lot to me to have people who understand, have been there, got the battle scars, and still willing to give encouragement to us novices.

I did tell my mother this afternoon about my crossdressing. My sister was there for moral support and she was terrific. I think my mother may have surmised something was different about me because she sat and listened as I attempted to explain what I was. She was full of questions from was I gay to was I planning on having an operation to become a woman. I tried to answer them all openly honestly but to be honest I am not sure about some of my feelings even this evening. She did ask for some time to digest all of this and think about her feelings about all of it which I understand. All in al I think it went well, not as bad as I had nightmares about nor as good as I hoped for. She did ask for me not to contact her while she digested everything which I consented to.

Perhaps the most encouraging point of the afternoon came as my sister and I were leaving. My mother gave my sister a hug and told her she loved her. She then turned to me and gave me a big hug and a kiss on the cheek and told me she loved me. I took that as a sign that in spite of my "hobby" I was still her child in her eyes.

My sister came over to my place after we left Mom's and we talked about how we felt it went. My sister feels Mom will be OK with it although maybe not supportive, kind of don't ask don't tell. I would be alright with that I guess. All I know is I feel like a load has been lifted from my shoulders tonight.

[CharLee]

Heather,

I'm glad things went as well as they did, even though not to the results you would have liked. Giving your mother time to take in all of what you & your sister have told about your dressing is a good thing. The one thing that concerns me is the statement of hers for you not to contact her while she digests this news. To me that doesn't sound so encouraging, more like she is just wants this to go away and not have to think about it. Since this was news to her I feel she should have wanted to discuss this more with you to find out every thing she could in order to truly understand your compulsion to dress. I hope I am wrong with my negative " vibes " and all goes well for you from here on out.

[Anthony Simon]

The one thing that concerns me is the statement of hers for you not to contact her while she digests this news. To me that doesn't sound so encouraging, more like she is just wants this to go away and not have to think about it...

I think it means, more likely, that she is conflicted about it but loves you and wants to get to the right place. That is she fears if you ring her (or whatever) before she's ready she's likely to give you a dusty reply. In a way CharLee may be right if your mother ends up in a "Don't Ask, Don't Tell" position your sister suggests because she'll be kind of making it go away while still treating you in a loving way.

[Diana Michelle]

Well Heather, how did it go? We all want to know and are praying it went well.

[Heather W]

Well I told my mother on Sunday of my "hobby" and to my surprise she was almost nonchalant about it. She did tell me she knew that I crossdressed and had known for years but never said anything to me about it. She did have the obvious questions as well as some such do I go out and how I liked to appear, hopefully not like some of those you see on TV she asked. She definitely seemed relieved when I told her no to that.

The two toughest questions she asked were" "Are you gay?" and "Do you want to be a woman?". They were the toughest because I am not honestly sure I know the answers to those myself and told her that which she accepted as an answer. I was certainly glad my sister was there for my moral support as well as to let Mom know I didn't act or look like a freak when I dressed. She also asked why I didn't tell her sooner and I told her I scared of her reaction. She told me that she loved me and I would always be her son. That did ease my mind some.

I think it went OK, better than I thought it would but not as well as I had hoped it would, maybe fantasized would be a better word than hoped. She did ask for time to digest all of this and told me there would probably be more questions, which I figured. Now I wait I guess. I told her when she had questions or wanted to talk to call me.

I guess I do have a question though. How long do you think I should wait to call her if I don't hear from her?

[CharLee]

Heather,

Glad it went so well for you, now you can relax and be yourself. Give your mother time to adjust, and give yourself time to breathe. When she is ready she'll let you know but if she does ask you in a month I would then approach her again.

In any event, congrats on telling her and her reaction