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For those of you have come out, be it to a close friend, to family or to anyone. How did you overcome the fear of telling your secret? Im stuck with it on the tip of my tongue. I need to open up before I go cooky.
Any advice would be well appreciated.
Thanx
I wrote letters to the people I wanted to tell. Gave me the chance to write it right. Then I just popped them in the mail and waited...
Hi Erica,
I have come out to several friends both male and female but I chose the people carefully as those I am sure would be accepting. With the exception of one person all took it well and my GG friends and I go out quite a bit now, and my guy friends still like to hang with boy me.
So my question to you is . . .Do you have close friends who you are comfortable telling? If so, these folks might be your best option. I did so over coffee or a meal and basically told them I was TG/CD point blank as there was no way to bring it into the conversation in a casual manner. The other thing you have to be prepared for is to answer questions (there were lots) and I did have a picture of me dressed (on my phone) should inquiring minds want to see.
The other thing you have to be sure of is . . . Do you mind if the world knows about you? The reason I am asking this is that once you tell a friend, you loose control of that information and this can spread like wildfire should things go bad between you and a friend or they just accidently tell someone because they need to share. I personally don't care who knows now so if my friends do out me intentionally or unintentionally, then I am prepared.
Hope this helps
Hugs
Isha
I spent a lot of time gathering my thoughts in a letter. I knew that I wouldn't be able to say it, I was able to say "Mom, I have hiding something for most of my life and I need to tell you" after that I just froze up and handed her the letter. I was hugging her the whole time that she read the letter. After she read it, the secret was out and it became really easy for me to talk to her then.
:hugs:
Kaylee :)
Mine started slow and easy actually as we had been married for only a few years. My wife had asked me after I was watching Her put her lipstick on. She asked if something was wrong I told her no I just have a fascination with lipstick and panty hose. She said well here and applied some to my lips. At that young age in life I nearly had a mess to clean up in my jeans it was hot. Then I told her about all my fantasies when I was small of my mom dressing me of the magazines and catalogues I had hidden in the barn loft and growing up loving to play dress up. We talked several hours that night after work and she decided it would be ok if I kept it hid to just her and me. I wore panty hose many times under my pants shopping with her for groceries, etc. she gave me her old makeup. She and I and all the gals on here know what I enjoy. I don't intend on coming out to every one ever as I'm just content to enjoy my dressing in my own space around the love of my life. She is my closest friend and we have had a life built together on living out each other's deepest secrets. She is a very good writer and one day she may write our whole story as a fiction novel but we will hold the one last secret as we will know it will be a true description of our wonderful life together. It is great telling your best friend, mother of your kids, wife and best friend. Really does keep one from going "Cooky".
Erica - I told my wife 2 years ago and its the best thing I have ever done, but I am very very lucky to have such a gorgeous supporting wife. The only advice I could give is be very careful, as once the genie is out of the bottle you cant put it back. I told my wife after she found one of her skirts had been put back incorrectly. We have been married 27yrs and it was hard to tell her, but she handled it very well. The older we get the harder it is to handle the whole CDing thing and I think maybe subconsciously I wanted her to find out so I unconsciously put the skirt back knowing it was wrong. Best of luck with everything and PM or email if you want to discuss it further....Ellie
Although there are others that know about my CD, only the internet knows about Carla. I'm to the point where disclosure just isn't a burning issue. It's more just matter of fact. I've found that telling someone that you're a crossdresser doesn't change their stupid ignorant assumptions about crossdressers. Disclosure rarely equals acceptance. I actually enjoy listening to my best friend when he goes on a rant about how gays and perverts are ruining the world. Meanwhile, I'm on the other end of the phone, in full sexy dispatch, admiring my nice legs and big t1t$ in the mirror. A fabulous, beautiful woman of the calibre that wouldn't give him the time of day.
I have found that the more people you tell the easier it gets. With that in mind start by telling people you know and work your way up to telling the close friends and family. This gives you time and adjustment period to fine tune your coming out talk as well as thinking over the answers that you will need for all the questions they're about to ask.
I got caught before I got to a point where I wanted to tell anyone.... Its quicker and easier and you don't have to think about it! boom.... its over! lol
It's your choice. Just remember once the "cat" is out of the bag. you can't put it back in.:)
Before you worry about how to tell people, you need to determine if there is a reason to tell.
If it serves no purpose, then there is no need.
If it will serve a purpose, and you understand that purpose, then the telling will be easy.
It just got to the point where I couldn't keep it to myself any longer.
I needed to be able to be me openly and was at last willing to accept the consequences of telling my wife.
I agree with Alberta_Pat on this.
I have not ‘come out’ to anyone, why would you wont to?:strugglin
I alaways wanted. To have someone to talk to that likes to dress,but i dont feel like taking a chance locally.I am surprised that the older i get i dont think twice about trying on heels or a dress or wig.I used to get nervous about buying pantyhose. My point is most cds realize how important it is to be discrete but it only takes one that could change your life.
I told the woman whose husband I would become well before we talked about getting married. The fear level was down, we were quite close, and I knew I could not keep this secret from her if we were going to get serious.
Also- to my niece / step-daughter, when she lived with us for a few years (she was in her mid teens), basically about the same time as she was discovering she was not strictly heterosexual.
I guess what I am saying is that i've only 'officially' come out to the people who are very close to me, and my crossdressing (or hiding it) would possibly have a negative effect on them. I would not 'disclose' to anyone unless there was good reason, such as mentioned above.
Erica, I'm sure this has incubated in your mind for a good long time. That's good because coming out isn't and shouldn't be an impulsive act, but rather a step along the way. And to answer your question - at some point the need to come out simply outweighs the fear of being outed.
I came out to my GF (now wife) when I believed I knew her well and that we were likely to continue long term. I needed her to know this going into the relationship. I came out to my adult step daughter when she moved back in with us briefly - and then only because her unpredictable work schedule made it likely that she might stumble upon me en femme....and I preferred a controlled and planned reveal to accidental outing. I came out to several very carefully selected business associates and friends when I felt I could no longer confine my dressing entirely to my non-working life.
I have come out a bit less cautiously with neighbors and merchants that I know in a passing way. I guess the risk of being out to casual acquaintances seems lower to me, its pretty hard to walk a dog, get a latte or pick up the mail without eventually running into a neighbor. About the only recent, unexpected outing was when my wife a neighbor lady over for a glass of wine on the patio while I was en femme. It was new to me, but it turned out she already knew. Non issue. Maybe I am a bit less threatened because a good long time ago, my ex wife took it upon herself to out me to co-workers, friends and family members. I survived the experience quite well. Being outed as a cross dresser in reality wasn't nearly as bad as my fears.
So the question you're asking yourself is a sign that you're getting close...that the need to share this very meaningful part of yourself is beginning to outweigh the fear. You're well on your way there. You've been out en femme already, so you've conquered that fear. This is one more fear that, I can assure you from personal experience, is largely overblown.
One last thing - your fears are probably overblown. Think about the person you want to share this with. Is he or she the kind of person you trust? If so, then plan your comments, be prepared for questions, take a deep breath and get it out there.
Well I came out to my wife. She's my best friend and if you can't come out to your best friend then what's the point of them being your friend? Obviously there not a good friend if they can't do the simplest of things like empathize, listen, and understand.
I think you really need to reassess your need to go public. I read in a prior post that a friend helped you with dressing/makeup. It seems most of us on this site struggle with opening up with their wives. It is difficult to "hide" this lifestyle from a woman with whom one interacts with everyday and in every manner. Others? Well, it is usually a casual relationship; friends, coworkers, neighbors, distant relatives. What will you gain by revealing yourself? As some others have said, "You can't put the genie back in the bottle!" With social media word of your cross dressing can spread quickly to others with whom you did not want to share this secret.
The big question I always have is "WHY????" Is it validation of self? I cannot imagine wanting to be en femme in front of people who are not accepting. If you want to interact with others, I suggest as some others have stated, find a support group with like minded individuals.
Your pictures suggest that you would be passable with a wig or with naturally longer hair, but, people who know you will still see you as a man in a dress.
Depends on who it was. Some I just told. Some I showed photos. I went to a Halloween party for my best friend. Told my mother that I was going to transition by phone. Told my dad the same way. Mom is OK with it, Dad is processing and won't talk to me. Point there is that he is the only one who was upset over it. I posted it on my facebook, forgetting that my cousin and aunt were "friends" that was interesting.
In other words, you will come out to those who need to know when the time is right and you won't have to think how, you will know
Well, in my experience, this are the most important things to remember:
1- Dont expect good reactions from nobody. Its important to remember that only you know whats good for your life, and other people will judge you based on their reality, not yours.
2- Dont think, just do it. Thats it, its like jumping in a cold pool, just let the words come out of your mouth.
I showed a couple of pics to my family and friends while I was dressed as male. My dad gets a little sarcastic, though......"so, what do you want for Christmas? Something feminine?"
One thing though. You get into this life and make it known, you have to be willing to deal with the negativity. However, I have been lucky to have accepting friends when I came out.
I still have not come out at work, nor will I ever, no matter how long my hair is, how much my beard as been zapped out, or how many holes I have in my earlobes.
For me a total of five people know; my wife (the first person I told), my therapist, my best male friend (who said he would totally date me but I told him he wasn't my type lol), a GG co-worker (that has become a good friend), and a professor of mine that I work with (she has also become a good friend). Each of these people I interact with on a daily or weekly basis, (my guy friend and I are working on a book) so I trust them, and they are very accepting people.
I wrote a post when I first joined about wanting to tell a friend; while I appreciated everyone's advice, many people seemed to say it may go wrong. It is true that once you are out to someone you are out, but if it is someone you know and interact with a lot than you should now how they would react.
Think about previous conversations; are they open minded, do they accept different ways of thinking, or they empathetic? It is something very big to share, and for those that I shared it with they saw it was hard for me and was very understanding. I know what you mean, when you say it is on the tip of your tongue, but sharing with someone makes us feel more normal, and can create a special bond.
I came out to my wife and only my wife so far. She has not been supportive and views this hobby as an aberration. The only way I got up the courage to come out was by coming to this site and finally accepting myself as a crossdresser.
I like this reply and also Kimdl93's. You don't give much information here about who you want to come out to, so, the "why", is only partially understood. If you are talking about an SO/wife then there is that need and obligation pressure to share something very personal to you that if possible should be shared with the SO. (note: if possible) If it is to a family member, like Mom or Dad, other reasons and needs come into play, like wanting them to know the real you before they pass away, or so that you can be the real you around them. If it is to have someone to talk with about all this, someone who will give you a good and meaningful hug when needed, then you could pick a trusted friend, or as many of us have done here develop friendships with someone who has this similar interest. I have followed this last scenario. It is not because I really needed to talk about it to someone special. I talk to everyone who does not know the male me and share what I think is interesting to share, and am willing to answer any questions asked. But by having a good friend I can also share personal issues with someone close. I have that friend and I do share when I need to.Quote:
Originally Posted by Alberta_Pat
So, once you determine the "why" you need to share, you can then identify who would be the best person to share with, and then pick some of the advice in the other posts here to figure out what approach may work best for you.
I hope all this helps and good luck.
Usually there was an opportune time and the conversation was about disguises and womens clothing.
Coming out is a personal and life altering event. Like pulling a trigger you cant pull the bullet back. Once someone knows you have to accept the fact that it can get around to others. It may never, but certainly can. I came out to my best friend, who is my wife. No other family members know, including my kids. For me I have a certain relationship with people and I don't want to change that. I am much more open with new acquaintances or strangers. Going to the store I have no problem being dressed as all man and asking the sales attendant if I can try this skirt on. And I have never had a bad experience with that. I also had no issue coming out at work. I just started and went through the process I thought best, and now I can dress at work whenever. It is great to be in a skirt, heels and nylons talking to a coworker about an issue and nobody treats you different. But these are relationships that do not exist already so they can't change from something you liked to something you don't. I can come in in ladies jeans and heels with a mans shirt no wig or makeup and nobody bats an eye. So for me that is key.
Erica, I simply reached the point where withholding it from my wife was more painful than telling her. I was driving her away and I knew why. It was unfair of me to push her away like that without telling her why. So I told her.
Now, in whom is it that you feel compelled to come out? If a girlfriend, great. If just friends in general, why?
I went cooky waaaayyyyy before I told anyone. ;)
Sorry Erica, can't help you. The only people I am out to are my CD-TG friends. They are very understanding and accepting, but we do share something special in what we have chosen to pursue.
Other than these girls, life is totally in the closet and there it must stay. Gets awfully lonely but outlets like this group help.
I wish you luck in finding the right words and opportunity if you really feel you must come out to anyone. Regardless, the girls here should always continue to be understanding and supportive.
Hugs, Robin :bunny:
Erica, I know how you feel , the brain is talking , but the words won't come out of your mouth. In the last two years I have told twelve people, my family, hair stylist, nail solon and doctor (last Monday). Every time I talk to a new person the same feeling, hard to start talking, but after you wonder what the problem was. No one has hurt me so far, so why the fear!!!!!!!!!!!!!!! can't tell way. Best advice I can give is bit your lip and spit it out.. you will feel like the world has been lifted off you shoulders, at least that is how I feel... Marsha
I came out to some friends that I thought were very close, we knew each other while I was in the military and they'd never suspected while I was in (talk about a UCMJ violation, wow) that I dressed occasionally (very occasionally, and never in a combat zone obviously :D ) and the first time they saw me dressed they said "Wow" and his wife said "You're actually cute!" I told her to put her glasses back on... but a few years later we sort of had a falling out and now I wish I'd never had come out to them. Like many people have said, you can't put the genie back in the bottle, or Pandora can't close the box, all the King's horses and all the King's men (why would the horses be needed for egg reassembly? I've never understood this)... etc.
I have a pretty close friend up in Canada, I mentioned one time that I wore a skirt to a Halloween party and she said "Well as long as you're not wearing women's clothes full time it's ok" and that right there said "HALT!!!" before ever bringing it up again. She jokes about me and my denim skirt tale but I know that this ... discussion... is not something I'll pursue any further with her.
I've decided now that no one else really needs to know this. It's like finding a UXO really, you never know when it's going to go off on you so it's best to just avoid it. :)
I can say I wish I knew crossdressers in my local community, but I'm in west Texas... just have a feeling there aren't a lot of us here. I'd have to travel to Austin to find folks, and that's a bit of a drive (220+ miles one way). It would be nice to meet with other people, both dressed and not.
dont take my advice....I did it when I was a bit tipsy ...I was going to implode if it diddnt come out....once it did the response to my coming out was....ahhh NOW things make sense ! Alot of my girl friends know....i dont tell guys ...
Either I have more brass than others or I'm just plain stupid, but I told people face to face that I loved wearing women's clothes, including two former spouses. each spouse I told before we got too serious and each one disapproved but married me anyway. I did the same when coming out to friends and certain family members. some are accepting and some are ambivilant but at least I don't have to hide anymore, and that mans more to me than non acceptance.
I notice alot of people here are saying "why"
Why come out, why do you want to tell people. Its not that I feel I want to, I think its to the point that I have to. Im not ready to tell the whole world, Im not even ready to tell close friends. But I need to figure out who or what I am. And the only way to do that is to talk about it. The one person I feel I need to talk to this about is my mother. I honestly do not think she will look down on me. Actually when I was in my early teens she had found my stash of cloths. She mentioned it to me but never made it a big issue and thats where that ended. But over some 30 yrs the dressing never ended. Through a marriage, through a few gfs, multiple purges and every day the feelings get worse. For my own sanity I think its time. First to talk to someone close then maybe a gender counselor to figure things out.
I hope Im not alone with this???
Eventually I just got tired of the fear and shame, told a few friends, then my mom, then a few more folks, and now almost everyone knows. Coming out is a highly personal decision, but for me, being trans was/is way too big a part of my life to hide. Hiding it would say that I'm ashamed of who I am. Not everyone was meant to fit in, and I don't want to. Some former colleagues have distanced themselves from me, but I have made so many more and am a LOT more interesting now than during the wasted years I spent wearing tan pants in a cubicle. It's also nice not to burden my friends with secrets anymore. :rose:
You just mentioned coming out to MOM(MOM is always big for me, lost 2 by 23) and then a therapist. If I may suggest the therapist first, this will give you someone whose paid to not be judgmental and might be able to give you some good advice after meeting you on how best to tell MOM.
I have come out to my SO only, I personally have no need to come out to others. Each one of us have our own levels of need in how far this journey will take us. Dressing at home fulfills me for the most part.
Best of luck in whatever your decision.
In all seriousness Erica, it can be a catch 22 for many people. Kind of damned if you do and damned if you don't. I think what most are trying to say here is be absolutely sure you want to tell another person before you do it. Once you let the genie out of the bottle, you can't put it back in. If you are in fear at all of losing your job, friends, spouse or loved one, then keep it to yourself. If none of that matters to you then tell whomever you like. At the end of the day you are the only one that can make the decision to tell. Chose wisely.
For 25 years, the only people who knew for sure were my mother and my father. My mother caught me dressing when I was 6. I would go into the bathroom, lock the door, and get dressed. The only problem was that it was the only bathroom and mom coudn't wait, so she used a hanger to unlock the door and saw me in her clothes. I cried, telling her how much I wanted to be a girl. That night, mom was supportive, as was my dad. Later, they went silent and told me not to tell anybody about wanting to be a girl. What I didn't know at the time was that mom had talked about it with her therapist who told her that the "cure" was electroshock, torture (aversion therapy), and if necessary, Lobotomy. Mom had been through the hell of electroshock and would do anything to make sure that I didn't have to go through that. This was back when they did not use sedatives and the shock caused your muscles to spasm and caused intense pain for several seconds until you blacked out. After the first EST treatment, they usually had to wrestle her onto the guerney and strap her down because she dreaded it so much.Quote:
Originally Posted by Erica Marie
Over the next 15 years, from 6 to 22, I went to see many therapists. They discovered that when I spent most of my time with girls, my asthma improved radically. They were thinking of putting me in a dorm with the boys until they realized that made my asthma even worse. They had me see a psychologist and I told him I wanted to be a girl, like Christine Joorgensen. He said "We know, but that's not possible at this point". He shut me down so firmly and quickly that I couldn't even talk about it. Several other times I tried to talk about it with a therapist and was shut down immediately. Each time it was "We know, but we can't let you talk about that". At 21, I had tried to kill myself using a method that should have killed me quickly and yet I somehow survived, but when I told them about wanting to be a girl - the REAL cause of my suicide attempt - I was shut down immediately, even though they knew I had just tried to kill myself.
When I was 25 I wrote it on the last page of my AA 4th step and almost didn't tell my sponsor. He said "Where's the pink elephant?". I had chosen him because he told stories about hustling tricks on the steps as the capital, so it didn't take much for him to realize that I was struggling with gender issues, but I had to tell him. I finally told him and he told me I had to tell my girlfriend.
That Christmas we were dirt broke. We couldn't even afford gloves for each other. She wanted "Rekkie under the tree", Rekkie being her nickname for me. I wrapped a sleeping bag in gift wrap and climbed in. When she walked in and saw me, she climbed into the bag with me and we had a wonderful morning together and slept. That night she said "I got what I wanted for Christmas, what do YOU want?". I told her I liked lingerie and she said she could put some on. I then asked if she had anything for me? She came out with a chiffon robe and we made love and snuggled. That was when I decided to marry her.
8 years and 2 children later, I was doing another inventory and shared the dressing and desire to be a girl with my sponsor. He told me he wanted me to write my inventory again, but this time I had to do it while dressed. I was amazed at how different the inventory was. I'd been doing inventories for 8 years and had 8 years clean and sober, but as a girl, there was a LOT of unfinished business. My sponsor asked me to give her a name. He also told me that he wanted me to come as Debbie to read my inventory. I changed in the car and met him in a private place, and read. Feelings I had stuffed for years came up, and he began to realize that I needed professional help. He suggested couples counseling for me and my first wife, The couples counselor had a few one-on-one interviews with me and realized that I was a "Type 6 transsexual". After seeing my inventory and asking me questions, he told me and my wife that I was transsexual and would probably be dead in a few years if I didn't transition. Then he pointed out that my wife was not a "Lesbian" or even bisexual.
After that, I was referred to a gender counselor. He gave me assignments every week, things I had to do as Debbie.
When I came out to my family, I was very surprised at their reactions. Mom said "I've known it all along, I just didn't know what to do about it". Dad couldn't understand why I couldn't just be an effeminate man like he was. He had told me several times that he had taken a test where they diagnosed him as 75% female. My score on similar tests was more like 95%. My sister said "you've always been the big sister I've never had, now your just my sister". I could brush her hair out without pulling it, could braid it, I taught her to do make-up, and she frequently asked my advice when shopping for clothes. My brother still struggles with Debbie. He knows it's an important part of my life, but he really doesn't want to be reminded of it.
This year I came out to my second wife's family, coming to Thanksgiving as Debbie. They all decided that they liked Debbie BETTER than Rex. It became obvious to them that Debbie was who I really was. For Christmas, Debbie got all the presents. They were concerned that nobody had gotten anything for Rex, but I told them that nothing could make me happier and started to cry tears of joy.
The first step is to stop trying to hide your feminine side. I've also found that it often helps to have pictures of me in tasteful clothes with make-up and a good wig. A picture of me in a ****ty outfit or cheap wig or bad makeup can actually make it harder. You might even consider going to Glamour Shots and having the whole treatment so they can take a picture of you as a beautiful woman.Quote:
How did you overcome the fear of telling your secret? Im stuck with it on the tip of my tongue.
I had both my ears pierced and got manicures with pink gel. Not totally obvious, but things that women pick up on quickly. When they ask me about the feminine traits, or compliment me on them, I tell them I'm transgendered. Very often, those who broach the subject first are very accepting and often very supportive. They often know other people who are transgendered.
I started transitioning and once I had been living 120+ hours/week for about 6 months, I sent an e-mail to my boss telling him that I would like to start working engagements as Debbie. He told me to update my picture and I changed my nickname to Rexy. This was necessary because clients need my legal name and gender for various clearance and background checks. Fortunately, my employer has a great diversity program and is very supportive. This is one of the reasons I chose their offer over several others.
Yes, you do. You need to find people you can trust that you can talk to. This could be a therapist, a counselor, a family member, a female friend, or even a male friend who knows and accepts your effeminate nature. Hopefully you have a few women friends and can share your secret with a few of them, not because you want to date them, but because you need a friend.Quote:
I need to open up before I go cooky.
Over time, as your come out to more people, you will become more comfortable. Eventually, you will reach that point where it's just part of who you are.
For many cross-dressers and transsexuals, hiding our "True Selves" can lead to incredible loneliness. I have described it as being like being sentenced to life in solitary confinement without the possibility of parole.
It was my ex-girlfriend. At that point, I felt I had little to lose. She was surprisingly ok with it, although she has kind of a big mouth, and I'd be surprised if that information stopped with her. I guess it's not important though.
As for what prompted me to tell her? Well, I was pretty sure I had marks on my back and shoulders from wearing... well, something that would have been really obvious if she'd taken my shirt off. And she tried to take my shirt off and I didn't let her. So I was on the spot and had to explain myself. It was super awkward.
I kind of wrote out my story so to speak. Then sent it in an email to the ones I wanted to know.
I have only come out to my wife and to others in the TG / CD community. My wife and I were married for 31 years before I actually came out to her. She caught me partially dressed once a dozen years ago but I purged and we never really talked about it again until I came out.
I guess I just felt a need to come out to her. I didn't want her to be shocked if she stumbled upon my now growing wardrobe ... or worse yet for someone else to find out and tell her. Coming out had two incredibly hard parts. The first was overcoming the huge fear that she would not accept me or worse yet, leave me. That was one of those bite the bullet and take my chances moment.
The second was how to go about telling her. I'm not a real vocal person but we have a tradition of making lists of what we might want as presents for birthdays, Christmas and other holidays. When she asked me what I wanted for Father's Day this year I included "a pretty sun dress" on the list. When she came to it on the list she got a funny look but it was a good way to break the ice. (BTW .. she didn't buy me the dress :sad::cry:)
As many have said, you can't put the genie back in the bottle. I'm gla I came out to her as I don't feel as guilty or sneaky when I do dress which helps my sanity. I don't think I'll come out to anyone else very soon. She is still somewhere between accepting and hoping I will grow out of it. Not nearly as accepting as I had hoped but we are working on it one step at a time. Good luck in whatever you decide.
I suppose that there is a right time and place to tell multiple people, like in a mass email. I have never come to that point in my life yet. I may never reach that point.
In my entire life, there has been only one person I revealed my crossdressing to. I was speaking on the phone to an old, close friend. He is bisexual, but not a crossdresser. He actually brought up the subject of gay people and crossdressers, which we both knew were 2 different things. On one occasion in particular, he told me about one of his co-workers whose son was a crossdresser. This guy's son would often go out in public wearing a black minidress, black fishnet stockings, and black high heels. My friend's co-worker was embarrassed by his son's clothing preferences, and he didn't know what to do. But he didn't try to force his son to stop doing it.
My friend had brought up these subjects a few times in the past, but I never said anything. But, on that one particular occasion, I just felt that the time was right to reveal my clothing preferences. It just "felt right". So, I did it. And I am happy that I did. First, I revealed to him that I liked crossdressing too, like his co-worker's son. Then, I said to him, "I'm wearing panties and pantyhose right now." If you think about it, it was kind of weird and funny. Here was my friend (who had no idea yet that I was a crossdresser) telling me about his co-worker's son who likes to wear black fishnet stockings in public. And, as he was telling me this, I was wearing black silky pantyhose myself. It sort of cracked me up a little. My friend accepted it and even enjoyed it a bit. He often asks me if I am "dressed". He now calls me up and asks me if I am wearing pantyhose. He sometimes refers to it as "playing".
So, my advice to anyone is this: when the time just feels right, do it.
Of course, if you need to tell multiple people at once, that is a different story. Some people here suggested doing it in writing. Maybe that is a good idea.
I have only told a few people. The ones I have told had already seen me dressed a time or two. Halloween or a "lost bet". That made it easier.
If you must tell, don't hesitate. Tell them "I've got something to say..." and keep on going until you are done.
Maybe aproach it as if you think they already suspect (if she found a stash years ago, she might already have it figured out).
I started walking out my door in a skirt and knew the people around me would see me sooner or later. I decided to tell them so they wouldn't get the idea that they "caught" me.
Some people can't handle it. For the most part, it you aren't ashamed of it, they will accept it, I think.