Telling your parents about crossdressing

I know this is a difficult subject matter for a lot of crossdressers, but I was wondering what might be the best approach to tell my father about my crossdressing. I've successfully told my mother and sister about it and they seemed pretty accepting of it. I'm just not sure how to approach it with my dad. I have technically been caught once and we had a discussion about it and I told him it was a sexual for me and at the time it was but I feel like my crossdressing has evolved quite a bit from the kind I was doing as young child. I also believe that he thinks I may have quit crossdressing but that is furthest thing from the truth. So anyone have good advice or examples of how you tackled this difficult situation?

The rest of your family is accepting - I think telling your father outright is a good start if you know where you stand for the foreseeable future. Please don't be shy to let him know how your crossdressing and the motivation behind it has changed, especially in your case where it started out as a fetish. If you have the luxury of taking the initiative to come out first, please take the fullest advantage of that if and only if you are sure where you're headed. It sucks, in comparison, to find yourself being outed and lost for words.

I was outed at a point where I wasn't really sure what I wanted. I don't know enough now even though I know better. Crossdressing is now at best a temporary relief for me - I only dress nicely as a woman if I'm going to take photos of my outfits, and it seems most likely that I'll mostly be out there in a tight vest/T-shirt and jeans. My parents, when they found me, were inclined to think of it as a fetishistic phase, comparing it to other sexual fetishes and calling me a "pervert" for wanting to present myself as a woman. I should note that their attitude is kind of NIMBY given how Mum mentions that some of the transgender women / crossdressers she saw were much prettier and dressed much nicer than GGs, but her own flesh-and-blood offspring would never be as physically attractive as a girl than as a boy. When I brought up the issue with them personally, Dad in particular dismissed it as a phase that he himself went through on only a single, known count. He didn't get anything out of it in the slightest. Neither have seen Lily in the open, or have seen any photos of her. The relationship is tantamount to DADT because crossdressing was never mentioned by name (let alone "dressed as a woman" except twice) and they're very reluctant to discuss it. To them, I am still James their son, the boy they sent to a single-sex school, the man they raised, the man they sent to the Army at the nation's command. Now that I'm partially already taking care of them instead, I think they will expect James to take care of them till their last days, in their last days. When (I don't even say 'if' now) Lily does bloom, I don't know how they will respond.

First I have to write what I write every time this "telling the parents" issue comes up: why do they need to know? Are you telling for THEM or for YOU?

Now, given your mom knows, she has already told your dad.

Jennifer(athome) - I think in many cases it's both. I don't know what culture Jennifer Michelle is from; given that she's in her mid-twenties it's entirely plausible that she may be living with her family or at least near them, which multiplies the need to know a good thousandfold. Furthermore, even though her father has already outed her and she presumably declared it a fetish for her, she might have changed her position since then. It'd be better for Jennifer Michelle's parents to hear it from herself and her current position in light of the latter, regardless of her proximity to the rest of her family.

It's also beyond our speculation what Jennifer Michelle's mother must have told her father in that case; the narrative is beyond Jennifer's control and may plausibly have misrepresented her.

Lily, to me, the "need to know" exists only if one plans to dress around whomever you "need" to tell. If one's cross dressing will affect those around them, then there is a need to tell. Absent that, it's a passing of the secret for the telling's sake.

In this case if my parents come to visit my apartment and go through my closet they will find my stuff it's not exactly hidden all that well and there really isn't a good way to hide it. I have it in closed containers but opening them doesn't require much. I can lock other people out of my room but my dad would be suspicious if I locked him out of my room. So in this case its more like its only a matter of time before he finds out or I tell him and I would rather him hear it from me then find the stuff and pass judgement lol.

I could see parents going thru their childs room and closets if in their own house, but why would they go through the closets in your apartment? Are they really that snoopy?

Going through your possessions in your apartment is a total invasion of your privacy. At 25 years old and living outside your parents' home, you have no obligation to tell them anything or seek their approval. I would tend to agree with Jennifer(athome) since your mother and sister know, the odds are your father knows also. You may as well just tell your father without debating or defending your lifestyle. Just declare it a matter of fact and leave it at that. If he does not want to accept you the way you are, then it is a real shallow relationship anyway. I personally would not dress around any family members if it made them or me uncomfortable.

Frankly, I would invest in a door nob with a lock in it for your closet. If anyone has the guts to try to open the closet and ask you about it, just asked them why the hell are you snooping around?

Hi Jennifer Michelle,

I did not tell my parents about my crossdressing but when I became ill they (after a few weeks) wanted to clean my house and had to open a few closets just to look for the vacuum cleaner, well can you imagine the look on their faces when they found a closet full with dresses and lingerie? but to their credit they did not say a word untill I was fully recovered.

so yes sometimes it is good to tell them just to avoid some circumstances.

good luck.

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Originally Posted by Jenniferathome

Are you telling for THEM or for YOU?

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Although that's an excellent question to know the answer to, I don't believe that's the gating issue. If your desire is to remain closeted, then it's appropriate for self-preservation reasons to make sure the person you're telling has "the need to know." If your endgame is to come out then it's correct to tell because it frees you from the self-destructive effects of having to lie to the people you love.

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Now, given your mom knows, she has already told your dad.

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I'd say 90% probable. Depends on the Dad and if the Mom would perceive it as safe. Maybe the best course would be to ask Mom if she's shared this info with Dad. You should still tell him directly but it will change your approach. If you have to bring it up cold, you do have lots of lead-in points in our culture today -- Catlyn Jenner, Orange is the New Black, Transparent, and almost daily news articles, though some aren't flattering to us.

Speaking as a Dad, I'd say that if one of my sons had something this deep, this foundational about themselves that they felt they couldn't share with me I'd be devastated and feel that I had failed as a father. But I recognize that all Dads (mine, for example) might not feel that way.

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Originally Posted by Jenniferathome

Lily, to me, the "need to know" exists only if one plans to dress around whomever you "need" to tell. If one's cross dressing will affect those around them, then there is a need to tell. Absent that, it's a passing of the secret for the telling's sake.

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This is how I feel. Part time dresser so if I'm never going to dress in front of someone (e.g. Parents) I don't intend on telling them.

I could never tell anyone,not even brothers&sisters.Part of my secret is I was dressing in mothers clothes,especially her good wardrobe.I was trying on her dresses,I removed a fresh,unopened pkg of pantyhose out of her drawer&put them on&gently
stepping into a pair of her heels&I would try on her short mini skirt&I borrowed one of her bras&reached in her closet&tried on one of her silky soft blouses.I would spend hours,dressed in her clothes,sitting at her makeup table,trying on her wigs,etc.I could
never take a chance of being caught fully dressed in one of mothers expensive suits&we are about the same size,so I could get away with it

Welcome to this fabulous form, Jennifer! True, your dad may already know, but 'man up' and tell him. I suggest this approach ... let your mom and sis know your intent AND have them WITH you when you reveal to dad. They will , hopefully, support you. Have your explanation to dad written down, let mom and sis see it to see if anything needs to be added or changed from their perspective, then give dad answers to the usual questions before he asks. Search the forum for help in this regard. Otherwise, as Jenniferathome says, don't do it. Just doll up and take mom and sis shopping! <grin>

I would do as suggested and really ask yourself if you NEED to. I have been back and forth on this myself, as I have major medical issues and my wife can't be around 24/7. I worry that I'll have an emergency hospital visit, my wife will drop what she's doing to get there, and my mom will swing by my house to pick up my medications and take care of kids. It's a concern that she might see something and make the connection. Actually, I'm not sure that she hasn't already, as this scenario has happened before.

As always, consider the worst possible outcome; then, if you can live with that, proceed. Even then, better to ask mom if he knows, and if so, how he responded. Most of us here live in the pink fog so much, we sometimes forget how most of the rest of the world thinks about us.....and it's seldom nice. Unless there's a particular reason that you think he will benefit from knowing, I'd simply not say anything.

Sadly both of my parents are now dead but even if they were not I don't think I would tell them about my crossdressing. It has always been a private thing for me as far as my family are concerned and I have never told my sister as it would not make life easier for me and I have no desire to rock the boat. As I said in my introduction I have made it known to a couple of groups but as far as my family it will always be a secret.

I can see that for some the need to open up to their families about their crossdressing could be an issue but, as others have said, one has to decide if the risk of creating a rift in the family is worth it.

I'll soon be 60. I'm a life-er. I grew up in vastly different times. I feel very strongly that in the vast majority of cases coming out in the way you describe is a bad idea whether it's your parents, friends, or anybody else. I do not understand the need or motivation. I think this is a Facebook kind of thing. Telling too much. I also don't get your parents snooping in your apartment. Who does that?? I wouldn't let them in my house.

I am in favor of expressing yourself around them and everywhere else to the level you feel comfortable. If you want to have long hair, let your hair grow! They'll either like it or get used to it over the years that takes, and either way it's absolutely none of their business! Same with other things. Get your ears pierced and wear whatever kind of earrings you want. Wear your nails long and polished. Get your brows done. Femininze your wardrobe. I'm not necessarily talking about skirts and dresses, but your jeans and shorts and tops can easily be feminized to some androgynous point. Maybe your working your way up to skirts and dresses, but you can stop anywhere along the line. It's your choice as you feel comfortable.

Told my mom and it was one of the best days of my life