Hi Ladies! Long time lurker first time poster here. Need opinions on what to do. I started crossdressing when I was a teen like many of you so I won't bore you with details on how it got started. I am in the late 40s now and have a big collection of feminine clothes that right now is bigger than my male ones. I work in an office at a big tech company and the dress code is very relaxed (pretty much jeans and t-shirt everyday of the week). The girls are usually more dressed up based on what is currently trending. I am only interested in women's clothing and not on make up, lingerie so I started a few years ago incorporating some of these clothes to my outfits but one could say they look more gender neutral (for example, ankle booties with no heels, a women's version of a biker jacket or women's jeans). My wife accepts and even helps me choose some of the clothes as long as they are not dresses, skirts or very high heels which I am fine. We used to go out on the weekends to concerts, bars, theater, etc and then I would go a little crazier on the outfit (leather leggings, knee high boots, a nice cowl neck blouse for example). With the lockdown and most of those things we used to do closed for now, it has been a long time I don't dress up. Even worse with the whole working from home thing. Recently the office re-opened but still with limited number of people allowed and people can go on a voluntary basis. I can go once a week and this as an opportunity to dress up (office is always nearly empty). One day I decided to wear cropped pants, flat ankle boots, sweater and a vest on top. A lady came and asked what was going on that I was all dressed up and started mentioning all items I was wearing lol. Last week I wore another pair of flat boots, a pair of ankle pants with a paperbag waist and a top. The same lady did not say anyrhing the entire day but when we were leaving the building she mentioned that she saw on the news the other day a guy that wears skirts and heels to work and he is srraight, he just likes the clothes. Do I keep pushing the envelope, or should I stop crossdressing? My fear is next time she will actually ask more direct questions.
Thanks
Courtney