Should I tell my GG Roommate?

Hi!

Long time lurker and rare poster. I bought a house a few years ago and recently had a friend who was renting somewhere and she had to find somewhere else to rent so my brother suggested that I take her on as a renter. We know a ton of the same people and occasionally hang at the same time at parties and such. We're both in our late 20s.

It's been hard these days to dress - or even wear a bra and forms like I like to do most nights while just hanging out at home. I'm not sure if I'm ready to tell her as we know a lot of the same people and word could spread fast, but I've always wanted a GG to have as a confidant. Should I try and hint once in a while? If so, how? Should I leave a bra visible in my room so she asks about it? I'm currently growing a beard this winter because it's cold in the north so I can't just fully dress and have her catch me as Ashley. Plus, I've never really wanted to pass, I'd need a lot of makeup and a wig. :)

Thanks in advance!

Ashley:<3::<3:

The big question is can she keep it a secret if you tell her. In the past has she mentioned anything about other people that would be considered not good.

You do have a conundrum. Just remember, once you tell her, you are no longer in the closet. She will tell someone else. However, if you do not mind your secret being out, then go ahead. With which are you most comfortable?

She hasn't really ever talked about other people and stuff she's heard about others. We chat but usually not about people lol

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Originally Posted by Laura912

You do have a conundrum. Just remember, once you tell her, you are no longer in the closet. She will tell someone else. However, if you do not mind your secrete being out, then go ahead. With which are you most comfortable?

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I'm not ready for it to be out. We've both grown up in the same area and know lots of the same people. Definitely don't need my parents finding out.

I think you've been given some sound advice.
With almost 100% certainty, she would tell others.
A loving spouse or an SO would be more likely to keep your secret (even if it really bothers them) because most have an innate desire to protect their loved one. Most... not all; I'm over-generalizing.
However, a friend or aquaintance? Seriously, how could they not want to gossip about something as juicy as this?

Here's a suggestion: Go Window Shopping. When your out with her sometime, perhaps in a mall to do some sort of shopping, you can stop in front of a a few windows to just look. She may want to go inside one or two for a look-see. At some point, you might caasually say something like; Wonder how i'd look in that" or "Do you think that woud look good on me too?".

Something to think about...

Tammy

My initial idea was to wear some unisex looking leggings around the house since I do work out and maybe sit and watch TV in my leggings and a sweatshirt and see what she says. That wouldn't "out" me and I could gauge her reaction. I also own some Uggs that I only wear inside, she doesn't know I have them but they are historically a woman's boot. If that goes well, test the waters further and ask for her secrecy since it's not socially acceptable (for the most part).

The only true secret is the one that only you know. My wife outed me by accident. I don't think letting her discover you is a good idea. Ask her opinion about guys CDing. Is she open to LGBT life styles.

my daughters friend nearly outed me while she was drunk at a party, drink loosens the tongue.

Unless you’ve got a deep emotional connection with her, I’d refrain from telling her.

If she is your lodger, and you don't tell her, how comfortable are you going to be in the realisation that you won't be able to dress as often as you would like, just in case she is there or she comes home early?

XDresserAshley, your words:

"I'm not sure if I'm ready to tell her ..."

Then you probably shouldn't. You say you both know a lot of the same people, chances are likely that she may out you to others either deliberately, or accidently.

There is an old adage: 2 people can keep a secret. If one of them is dead.

Once a secret is revealed, you can't re-conceal it. Just my 2 centavos, your mileage may differ.

I think Liz is on the right track. See if you can work out something where the two of watch a show involving crossdressing (without making I obvious you arranged it) and see how she reacts. If she has a very negative reaction you'll know right away that you shouldn't tell her. If she reacts more positively you can hint a little and see what happens. I agree with some of the others though that if she knows about it sooner or later she will likely tell someone your secret.

You may either tell her or don't tell her, your choice. But don't "hint" by leaving a bra visible or any other female items laying around. She may not ask you about it but would most likely ask her friends what they think about the girl items she spotted. Trying to be sneaky without telling her the truth may not have the effect that you are looking for. If you are up front about your dressing, you at least have the opportunity to ask her to keep it quiet.

If you really want to do as you please in your own house, maybe you shouldn't have a lodger if you are worried about their reaction to how you live your life.

You gotta bring it out in the open somehow.

It could be construed as weird otherwise.

I had a share house and had four girls as tenants, they dressed me up once to fool one of the parents into thinking there were five girls in the house.

In reality the girls were happy renting with me because that kept all sorts of predators at bay having a male minder.

Because I was a 98lb weakling I made a good looking girl and they all loved dressing me up to see how hot I could look.

Yes, it was a chore sometimes..... WHAT A CHORE. :-)

Her knowing would give you SO much and would relieve all. The question is if she will keep the secret. So test for secret keeping abilities. Or as I would probably do is ask her ....have a conversation about keeping secrets. Get a comfort level and decide.....the win is freedom.

I agree with char, if you try to leave small hints, she is likely not to ask you about it, but instead talk about it with others. If I were you I would go ahead and tell her, but it is totally up to you.

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Originally Posted by XdresserAshley

I'm not ready for it to be out.

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Remember, the number of people it takes to keep a secret: ONE.
Women, whenever experiencing any conflict, like to discuss it. And they won't be discussing it with the person with whom they're having the conflicting thoughts.

My view, way more reasons not to tell her than to risk it. Sorry, but there are only 2 ways this will go: you tell her and she is so unfazed, she instantly forgets that her bearded landlord wears a bra or she is fazed and will have no obligation to keep what she heard a secret and all of her friends are yours too.
As another mentioned, there is no unsaying it. Trying to feel her out on her view tells you nothing about how she would react if she knows the CD.

what you are proposing is nonsense, why you want to tell and how it will end will not be what you desired.

as mentioned, a little wine goes in a little truth comes out....you social circles overlap....once the toothpaste is out of the tube it cant be put back in.

you own your own home at a young age +, they sell ski masks to keep your face warm +, you dont have to pass to be out in the wild +,....you just have to accept yourself. not preaching just an observation from my experience.

to find a accepting GG you might have to find a place where accepting GGs hang out, try a local meetup and concentrate on LGBT accepting ones. any local LGBT clubs? try those, not going to be the easiest task but you might just meet the girl of your dreams this way, the Q in LGBTQ is questioning and from talking to my lesbian friend us t-girls are an option they may have never thought of ???? then you wont need a roommate anymore....

You should have thought about your privacy before you decided to let someone else into your home. Telling her would be a bad idea in many ways. She would have the power over you and if anything ever went wrong, she could threaten to tell people about your secret.

Best bet if you want to dress is to get her out of there.

You have to decide a more basic question:
Which is more important - the freedom to do as you wish or the need to hide?
If you believe the former, then tell, with the knowledge that your crossdressing is no longer a secret, although I would ask whoever you tell to not discuss it with others as you reserve the right to as to who and how to tell.
If the latter, then not only should you tell no one but you should lose the roommate as you put your secret at risk as long as she's there.
The only way to keep a secret is to tell no one, to display it to no one and to not leave evidence that would let someone infer your secret.

While she is staying there, she is not likely to tell your secret because she would risk losing her place to stay.
But if things go bad and she moves out voluntarily or not, you already know that will be the first thing she tells everyone.

The nice thing about being "out" with one's gender status is people cannot so easily use it against us.

I would tell her by asking her what she thinks of someone who's transgender to feel her out. If she is OK with it then tell her you like to dress. And don't grow the beard. I live in Michigan and it doesn't help with the cold. We just had 10 inches this week.

Thanks for all the input everyone! My plan at this time is to keep it quiet and maybe to bring up the topic in conversation. I won't leave any thing out for her to question and I'm not ready to full on tell her. It's likely she'll move out in a year or so and I'll have my freedom back. I did wear my Uggs yesterday for the first time in front of her and she didn't even comment on it and when we were talking she did check them out a few times. I don't think she cared at all.

If any major updates happen I'll for sure update you all on the situation.

Ashley