How far to push the envelope...

I've been struggling lately, with working from home in the foreseeable future I've been taking advantage and dressing all day. It's been fabulous.
My nails are long and always painted, no makeup but nice perfume and earrings.
I've always been one for pushing boundaries, women's jeans (including some nice leopard print skinnies), girls tshirts, painted nails.
I've also been wearing women's coats, admittedly they're not ott feminine but nice non-the-less.
I recently bought a faux fur long coat and it's amazing but definitely less unisex.

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The reason I'm struggling is how far will this go ? I'd love some heeled boots to go with the jeans, prettier earrings and rings and I can see this getting a little out of control. I'm very lucky to have a supportive wife but she obviously has her limits. Anyone else finding it hard to go back to boring generic clothes ?

If I was single this would be more a picture/gallery type post showing what skirt i wore or dress but I've got to rein it in.

Thanks for listening to my ramblings

Roxy xx

I have also been enjoying certain aspects of working from home.

I have a friend at work who I am out to and she hasn't noticed some days when I am wearing a dress or blouse during a zoom meeting. I've had dozens of meetings with my boss, co-workers, and even clients. I wear a dress or blouse for most of them and my co-worker who knows has even been on those meetings and didn't say anything about it afterwards, even though she certainly would. I was wearing a dress one day and we were on zoom just before the meeting with my boss started and she told me to either change or take out my forms/take off my bra because it was too obvious and it would likely be noticed.

So, yes, I am in the same boat with you. It is going to be tough going back into the office working in a male dominated industry (transportation) and having to repress my femme side.

If I had a supportive wife and was not six foot tall and 200 pounds I'd be pushing the envelope as far as possible during the Covid lock downs. Masking wearing offers some concealment of a male identity. I notice all the time when I am in a Target or other store in the morning a lot of women attired in dresses and skirts under their outer short coats. They are usually grabbing something on the way to work. I'd love to be going through the self checkout line totally en femme and wearing a cute mask. If you have the goods, push it as far as possible. Cold weather offers concealment.

We all have our own individual boundaries to challenge, Roxy! Congrats on pushing yours!:thumbsup:

I've found that after I pushed myself to appear as Sherry in Cambodia, Indonesia, and Singapore? Getting apprehended as Sherry and tossed out of casinos in Vegas was hardly disturbing!:heehee:
However, u STILL won't see me dressed at Denny's or the mall!:thumbsdn:

I don't understand posts that ask us to define your limits.

Your limits are decisions that are yours and yours alone to make.

Then you should have an open and honest discussion with your spouse to determine if those are limits they agree with and adjust accordingly working together.

It almost sounds like you are hedging toward a hybrid DADT setting. If you push beyond your current boundaries, that would be DADT, but if you stay where you are at, then it's accepting.

I bought a coat similar to yours from Zacs at a Black Friday sale some years ago.

I found it very easy to push the envelope with a pair of boots to match.

This is the coat in my present avatar taken about a month later in the UK.

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Originally Posted by Robertacd

I don't understand posts that ask us to define your limits.

Your limits are decisions that are yours and yours alone to make.

Then you should have an open and honest discussion with your spouse to determine if those are limits they agree with and adjust accordingly working together.

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I'm not asking for anyone to define my limits just comparing and contrasting with others experiences.

Pretty coat Roxy. Wearing a knee length dress coat with a dress or skirt completes my transformation during the cold months and definitely helps with passing. Yes I do struggle going back to my boring clothing after a dressing session/outing. As far as pushing the envelope I also struggle with wondering how far will I push it.

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Originally Posted by *ROXY*

I'm not asking for anyone to define my limits just comparing and contrasting with others experiences.

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Okay, well you asked how far will it go? In my case it has gone as far as me presenting as female full time and starting HRT.

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Originally Posted by *ROXY*

......................... just comparing and contrasting with others experiences.

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I believe you have an enviable situation of acceptance and should respectfully utilise it to derive the greatest happiness for you and your wife.
Many of us are strapped tightly in the straitjacket of DADT and would love to have the latitude that you have in your relationship.

Sherry, if you'd tone it down a little, you'd probably have fun at the mall. :)

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In my case, how far to push the envelope is determined by my wife.

I let my wife know that she comes first in my life, and if I wear something she can't stand, then its her job to let me know. I will immediately take action to ensure that she is comfortable.

I am fortunate that we seem to have found a comfortable working arrangement where both our needs are respected.

Actually, u may be rite, Carla! It's freezing here. And, I think our malls may be opening soon?

So, maybe you'll see a masked Sherry in a coat and heels in some mall pics soon! :battingeyelashes:

The last time Sherry was in there filming? They threw me out of Macy's, then the mall!:heehee:

Excuse me for sounding dumb sherry but why did they throw you out of the store and the mall if you can say. That sounds sorta harsh on their part? Plus helps us handle situations like that for the future if you don?t mind?

To answer the OP's question: the short answer is "No".
Jon

don't forget that cameras can show unexpected things that you don't think about. The reflection of a shiny bra through the weave of a sweater. White bra under a white shirt or top because it can show the bra since the skin tone is different.

Some cameras see beyond the visible light range into the infrared region. A friend told the story of taping his daughter's dance performance, only to find that their costumes were transparent to infrared so you could see *everything* in the video. They had to destroy the tape.

I know where you are coming from. I love leggings and wear them almost 24/7. All styles and colors. I have also started going out in public with my nails painted. My wife is understanding but she is concerned that some of our neighbors might see me either fully dressed or with the painted nails. Almost everyone I know has seen me in leggings since I run and work out in them also. So i'm sure people have an idea but to date no one has said anything. I would love to dress even more feminine but I think that would definitely be a bridge too far for my wife.

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Originally Posted by susanmichelle

Excuse me for sounding dumb sherry but why did they throw you out of the store and the mall if you can say. That sounds sorta harsh on their part? Plus helps us handle situations like that for the future if you don?t mind?

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I imagine it has a lot to do with the masks she wears. Macy’s security is really tight and someone in a mask might be trying to rob the place.

As to the OP:

Only you can say how far it will go. I think a lot of girls go through the “what can I get away with?” phase. Mine was short because I quickly realized a couple of things:
1) no matter how subtle you THINK you’re being, someone out there WILL notice. They might not say anything, but it does get noticed.
And
2) I dress TO get noticed. When I dress I want all eyes on me. When I walk into a room I want everyone to stop and say “wow!” No “blending” or “passing” for me! Some girls get great pleasure from flying under the radar as a woman. Definitely not me! It’s an amazing feeling when people know you’re a man in a dress but still involuntarily suspend disbelief because you’re so fabulous. That’s why I got into Drag.

You can push the envelope just as far as it adds to the lives of you and those around you. Further than that and you run risks. Whether that is enough for all of is is another question. Personally I value and enjoy what I have too much to push it further. Enjoy life, be a bit selfish, but don't risk what you value most.

Similar to Doc's experience, my hubby had a tri-pod set up in a mall common area and security did warn him that taking pictures was not allowed. I suppose if he hadn't stopped, he would have been asked to leave. I don't know if all malls have to follow the same rules.

Now he is just a little more discreet; no obvious tripod.

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Originally Posted by docrobbysherry

We all have our own individual boundaries to challenge, Roxy! Congrats on pushing yours!:thumbsup:

I've found that after I pushed myself to appear as Sherry in Cambodia, Indonesia, and Singapore? Getting apprehended as Sherry and tossed out of casinos in Vegas was hardly disturbing!:heehee:
However, u STILL won't see me dressed at Denny's or the mall!:thumbsdn:

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Never been to Cambodia, the others ticked. Singapore has to be one of the most accepting places on earth, I have been there a few times from the 80's to just last year. Did you get to the pearl at Changi airport, what a caricature of a place. Every thing is fake yet so wonderful a representation of real life.

I heard somewhere...that malls are afraid of terrorism...and the associated threats. They get nervous about strangers taking pictures--just in case they are planning some kind of attack.

I routinely go to the malls and other stores, laundromat, grocery supermarket, etc as a female....before the pandemic and now with the required medical mask.
I always wear dress or a skirt an blouse, Of course, exactly what particular dress etc that I wear and how casual they might be depends on where I am going , etc.

I never do anything out of the ordinary and and I am completely at ease doing this and not a bit nervous about it. I have the mindset that I am just wearing the same lingerie other clothes that any other female would wear..
I never have had a problem. Bottom line, if you do things to draw attention yourself, will of course draw unwanted attention .

BTW right after the recent events, there were a couple of uniformed NY State police men roaming the local Galleria Mall obviously "just in case" . Neither on of them gave me a second look

I should add that I have my own natural, long (past shoulder length) grey hair the helps me to pass. :)

I think my envelope has been pushed so far it was on Elon musk's last rocket launch . I've come out to a few people at work And the usual response I get is I've known since... Fill in the blank . I'm out in the community Not our community my community where I live . I go out to all this straight places So a lot of people at my age know me . So for it to carry over to work is no surprise I work for a large company . It's Understandable eventually some people I don't even know will recognize me or see me out and talk or whatever. None of it comes back to me at work unless I bring it up so that's a good thing and it doesn't really make a difference anyway . As far as recent limits I pushed My nails are long and I started doing them Myself I just necessity due to The Covid shut Downs. Acrylic and polish and everything else . Is anyone was wondering that was probably the biggest giveaway people tell me when they saw my long nails . They had their suspicions but that confirmed it . Everyone's been great about it. No one really cares. Nothing changed.

Genifer Teal - so cool! This year I?ve started coming out to friends for the first time.

I?m trying, and failing to grow long nails! If 7/10 was OK I?d be doing better.

hello Roxy,
we all find out happy place eventually - but just remember that you cannot squeeze the toothpaste back into the tube!
Have fun and stay healthy!
luv J

It has often been said that how far someone who is TS to any extent "pushes the envelope" largely depends on their opportunity... which includes their life situations which enables them to do so.