How to come out as a crossdresser to my family?

[Bicurious03]

Im a male who has been wearing womans clothes for about 3 to 4 years without any family knowing... i really like wearing leggings, with a nice pair of flats or nikes...(Heels occasionally)! I want to tell everyone so i can do it freely and not worry about being caught anymore. I already do it publicly but in fear someone will see me and snap a photo! Please help!!! I need to know some options?

[gititboi]

Okay, so, on the one hand there's crossdressing, and on the other there's being transgender. If the compulsion to wear clothes from across the aisle is so strong that it effs your mind around people who've known you since birth, then the smart money is on transgender, with the dressing thing just happening to be your first route to discovery.

Because if it were just dressing, then, it'd just be dressing.
Crossdressers who are just crossdressers, i. e. who are NOT gender dysphoric, are not massively conflicted by, e. g., work dress codes, or by being around family with closed-minded/provincial outlooks. They follow THOSE 'rules' as long as the situations obtain... and then they indulge their little secret when they go home (or to their storage locker, hehe)

That you want to x-dress so often and so regularly, in fact, points toward the transgender hypothesis as well. The whole point of 'crossdressing', as a non-transgender non-dysphoric kink, is that it's a little secret to be shared only with a chosen few, if indeed with anyone.

Oh, and. Life lesson number 1-A.
People just DO. NOT. CARE. At all. About what you are doing. Unless their self-interest or safety (or those of their loved ones) is directly impacted.
Really, they just do not care at all. You could walk around the mall or around downtown in a porno-style schoolgirl outfit and nary a photo would be taken (people would just guess you were some crazy street performer, or just a street person).
Along the same lines, people also won't notice that expensive car or watch you went into massive high-interest debt for, so, don't buy 'nice things' to impress anyone but yourself.

(There are exceptions, such as 3rd world countries and small towns where EVERYONE is in your business about EVERYTHING. Since crossdressing in public brings threat of physical violence in most such places, I'll just assume you don't live there.)

[SteveSmith1985]

I'm no authority on gender, transgender and "dysmorphia" related issues. I have a feeling that you aren't either. I do know enough to know that you're dead wrong on a couple key points. I'm sorry I'm honestly not trying to be an jerk, but what's rubbing me the wrong way is that the way you're writing (intelligent and articulate but also very authoritatively) makes it seem as though you know what you're talking about, when some of what you're telling this guy is , as far as I know, incorrect.

According to my admittedly limited understanding of the subject, no transgendered person has ever needed somebody else to tell them that they do not feel that their sex matches their internal gender identity. It's usually described as a lifelong feeling that permeates to their deepest concept of self. They often discribe the dysphoria of knowing which gender they were inside, while they weren't born with the corresponding gentiles. Nobody has to suggest that their gender dysphoric, they can't escape from KNOWING it... basically all the time they weren't able to "be themselves". Again, I'm not trying to be a dick, and maybe I'm dead wrong, and you do in fact know a whole lot about all of this.

Look, my intention isn't to make you feel attacked. You're clearly an intelligent guy, and I think that's what's a bit dangerous--when you say everything so definitely, authoritatively, and with no qualifiers to soften the absolutenes of your statements. Basically this shits too serious for anyone to get advice from someone who they think is an authority, but isn't actually...

[SteveSmith1985]

And as for people not caring, I have a bit of a different take from you but have no bone to pick like the one above. It's not written the same way, and even if it had been, there's no danger somebody will think you're a "people expert" teaching them real insights into something serious.

I agree that generally people don't care in a fast-paced world where an individual is simply one more person within an anonymous crowd: "the public" or "the community". So if I showed up downtown in a dress (I'm a straight guy) I agree, nobody will really care. They just see one more instance of something they consider strange, then don't ever think about it again. BUT if I ran into my: boss, sister-in-law, next door neighbour, old friend, new friend etc. THEY sure as shit would care, even when their self interest isn't impacted.

[gititboi]

@SteveSmith1985 ... Your platform, as you literally wrote it: "I'm definitely not an authority. I presume, on no basis at all, that you probably aren't either."
AKA
"I know nothing... but I think you probably maybe might not know anything, either."
... Well, then.

That's about as convincingly authoritative as the "Doms-with-a-capital-D" are actually dominant. Heh.

I CAN be a decent bullshit artist, but...
... this is the internet, where bullshit/sarcasm/irony are not as obvious as old farts like me might presume,
... unlike fake 'parties' where people go to be strapped to fake equipment by fake capital-D-Doms and fake-hit in strictly pre-negotiated fake ways, this stuff is real deep psychology,
and
... since I don't know the audience, I need to write simply, literally, and accurately.

You mentioned "softening" my statements. There's nothing to soften. Good writing is direct and to the point.
(If you read good writing aloud, you SHOULD sound like a tactless, artless, socially inept boor.)

__

Yes, there is direct observation and/or firsthand experience behind everything here.

))) no transgendered person has ever needed somebody else to tell them that they do not feel that their sex matches their internal gender identity (((

Wrong to a shocking degree. The closet is a thing that is very much a thing.

Consider homosexuality.
This kind of denial is so ridiculously widespread that there are whole subcultures (plural), with vocabularies all their own, that exist for the SOLE purpose of reassuring factually bi-/homosexual men that they aren't what they are.
E. g.,
"sissies" ... are boys in dresses. Who are still boys. If you wana fuck them, you are not "str8", you are bi or you are gay.
"heteroflexible" ... in other words, bisexual + in denial.
Etc etc etc.

Self-awareness is pretty rare in general, but nowhere else in society do so many people spend so much energy propping up a delusion that says black is really white and up is really down.

Your assertion that

[gititboi]

transgenderism is something-they-always-knew-deep-down-inside is also plainly contradicted by the treatment of eminently impressionable younger children. Twenty years ago, when your 6-year-old son said he was a she, you smiled, indulged him/her, and let children play children's games. Now there are groups of hysterical 'adults' who demand the same gravitas for that 6-year-old as they would for postwar PTSD. That's the same age when he/she/it will gladly eat dirt for dinner.

__

))) So if I showed up downtown in a dress (I'm a straight guy) I agree (((

That little disclaimer there is exactly what I'm talking about.
Sexual orintetation isn't even on the table here; the issue is crossdressing kink vs. canary-in-the-mine bellwether of a future gender transition. The OP has already established that he is bi... hell, it's his username.

[SteveSmith1985]

Hmmm, that's a pretty tough one. I would think that it would largely if not entirely depend on what your family is like. Are they generally more progressive, accepting of "alternative lifestyles" (haha, what a great euphemism)? Do you have a close relationship where you guys can talk about sexuality and whatnot openly and comfortably? Or are they more the traditional "family values" types where men are supposed to be tough and manly?

I think this is the inherent problem with asking advice from people here. Even somebody knowledgeable about how to go about it (definitely not me) would need to know more specifics to your case.

Your best bet is to seek out some local LGBT resources in your community. You need to ideally find someone who can talk to you about your specific case. In Canada it would be stupidly easy to find those resources. Just occurred to me that depending where you live, might not be as easy. In which case... online LGBT resources. This isn't something a random yokle will be able to help you with.

P. S I admire your balls (pun intended yes, offence meant, no) for wanting to get it off your chest and not want to hide who you are or what you're into. Cheers. Best of luck

[JessieH]

I know it’s tough but you have to be your authentic self! Do you have anyone who you can trust or would be more accepting? If so, approach them first and just be honest. My brother came out of the closet a couple years ago and he’s so happy now. He told me first and I was honored.

[Anonymous]

I would just sit them down and tell them. Like ripping off a bandaid. I hope it goes well. And just know that if your family doesn't accept you, there's a whole community of people out there who will. It's going to be alright.

[gititboi]

This is one case in which that latter statement is not true at all.

Because of the core nature of the crossdressing kink —
• doable alone
• (usually) secretive
• at odds with the desires and preferences of (most) partners
— it tends to stay individual and hidden.
Crossdresser social events essentially do not exist at all — other than tgirl club nights, which aren't organized to help cd's socialize, but more just to farm them out to 'str8' men as 'sissies' (= definitely plan C, after biological women and post-op+HRT trans women as plans A/B or B/A... but, hey, at least they can stay in denial about wanting sex with men!).

The closest thing to a 'community' out there is a diffuse set of voices helping the cd's try to make sense of what's going on, but, that is far, far short being meaningfully a 'community'.
And, it may not ever be alright. It could be a solitary, masturbatory fantasy kink until your dying day. But then again, none of us end up getting EVERYTHING we want.

__

Among women I've known well, the closest analogy that springs to mind would be an intense rape kink (obligatory disclaimer: this basically never means actual rape, but that's the only way to describe this kink in under 5,000 words).

An empathetic, strong, sexually intense, emotionally dominant and tenacious partner CAN turn that kink into an amazing shared source of intimacy (as is true of crossdressing, or just about any kink at all except a heartbreak/abandonment fetish), but, those are rare. Tragically, it's far more common for partners to try to compensate for a history of sexual coercion by 'comforting' the woman in ways that INCREASE her disaffection and sexual frustration.
So... this particular kink is indulged alone. usuallly shamefully. thus making it kinkier. chicken and egg situation.

There are no rape-kink parties. That niche is filled by 'those' romance novels. The ones your sweet comforting husband SHOULD pick up and read, but never will, you nasty little thing you.

[Opinion Owner]

@gititboi There are people out there who will accept him. I don't know what the point of you saying any of that was, but I know plenty of groups of people who are accepting of cross dressers.

[gititboi]

"accepting" and/or "tolerant" --- which are true of most people about most traits of most other people -- are not nearly the same as "supportive".

[SteveSmith1985]

@gititboi I think you paint an unnecessarily bleak picture of life as a guy with a cross dressing kink. I don't have this kink myself, so don't have any insight there.

But if your analogy to the female rape-fantasy is a good one... I can provide you with some insight into THAT based on personal experience. First of all, there are most definitely "rape-kink" parties. In every major city in North America, I assume similarly in many Western European countries. is also a HUGE international community online. Many members use the online community to plan and attend real life events. Additionally, you're mistaken to think that those satisfying, intense relationships with a dominant partner who can indulge her in her fantasy are rare. I assure you, they are not.

Welcome to the world of BDSM and S&M. Rape fantasy, in any and all variations are indulged in openly within the BDSM scene. The relationships aren't rare because the community is generally made up of both: 1. Submissives (the group in of which women with a rape-fantasy fit), But don't forget about all those Dominants (many are men with a fantasy of being the violent rapist but of course its CONSENTUAL. So we have Ying and Yang...

[SteveSmith1985]

...

I'll also mention that rape-fantasy among women, is very very common. Very. Like you said, FANTASY, not in any way wanting actually be raped. For some it's not in the forefront of their fantasies they're into. For these women, some will explore this fantasy with partners at some points, others never will, and are indeed ashamed of finding it arousing. But since its not a central component of their sexuality, not exploring it doesn't have serious consequences. For women for whom it is central to their sexuality, they will stumble upon a welcoming BDSM community.

I KNOW that many (most) women with a rape-fantasy do not live the loanly, disconnected, unsatisfied, sexually-self-ashamed life. Nor do they have trouble finding a partner that fits their sexual proclivities like a glove. If you don't believe me, maybe start with FetLife, if you really want to start the journey down a pretty crazy rabbit-hole. (And are over 18! 🤤)

Since you were dead wrong about that, I'm hoping that you're also dead wrong about that pretty disheartening vision of this guys sexual life going forward.

[gititboi]

@SteveSmith1985 If you think that "bdsm" and "kink" parties -- with their specialized terminology, specialized gear, kindergarten-style binaries ("dom"/"sub", "bottom"/"top", etc), formalized safewords, and drilldowns of consent + consensual nonconsent + consensual nonconsensual nonconsent + ••• + consensual (nonconsensual)^N nonconsent, and 60,000 other constant reminders of just how safe! and fake! and not real life at all! they are -- do ANYTHING to indulge a deep-seated rape fantasy kink, then you have a LOT to learn.

Those parties are better understood as niche subcultures. Note the strong homogeneity in looks and lifestyles among the regulars... and; as unpalatable and brutal as honesty may be here, the complete lack of conventionally attractive people among them.
It's a niche. If it's yours, good on you for finding it.

It's about as likely to impact a rape kink as Call of Duty is to give you actual PTSD.

[SteveSmith1985]

Sure. Clearly I have no idea. I'm guessing we likely aren't going to agree on much or contribute anything constructive to this discussion (things may have veered off the original guys question). That's ok. I said something, you've replied. Let's just leave it at that☮️.

[gititboi]

@SteveSmith1985 Sure. Thanks for the compliments on my writing, by the way.

[JackSmy]

Not something that is good to talk about, openly, here. PM? I know many in the LGBT family, and have a few friends, and one in my family.

[IoffurAdVice]

Depends on your family's views on gay people. Like this statement or not, crossdressers are going to be looked at as homos.

[DeviloftheValleys]

Why do you have to "come out"? Don't make such a big deal out of it! Just be yourself and stop worrying.

[Hurdleez-Swampede]

Ease into it but if they disprove, then move further away.

[SteveSmith1985]

Hahaha, I would love to know what "easing into it" would look like exactly. 😅☮️🙂

[NickerLover]

In fashion, duh faggot

[ivanhunterjo]

Depends on your families views