For most of my marriage, I did this, too. However, it was with my (now late) wife’s knowledge – and frequently her participation.
Importantly, though, I never felt comfortable in her clothes (other than certain panties of the right style and cut – as in that department we were both size “medium”) and I put this down to women’s clothing being cut for a different anatomy.
After her passing, I went through her wardrobe (and that of my daughter, who was no longer living in the house) and tried on numerous items. At some point, a light in my head went on and I realized that I ought to try larger sizes.
Over the last three to four years, through online shopping following targeted in-person reconnoitring forays through the ladies’ clothing department, I now have a decent (and expanding) collection of dresses, skirts, blouses, ladies’ shoes, ladies’ pants, pantihose, tights, leggings, etc. etc.)
Finding your right size takes some research (many online shopping websites have sizing/measuring guides) plus a bit of guesswork and sheer trial and error. Only twice or thrice have I been able to muster the courage to try on a woman’s garment in the shop.
Having now gained some experience in gauging how a woman’s garment will fit my body, I am able to run my eye (and sometimes hand) over a woman’s garment in the shop and estimate with reasonable accuracy whether it will be a comfortable fit and happily I have progressed towards becoming a developing judge of whether certain colours and patterns would suit me.
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