My husband and I were painting our first home after our recent marriage, and back then painting was a big messy job. My husband Jim complained that his clothes were too restrictive and nonchalantly asked if he could wear one of my older house dresses to be more comfortable. I tried to restrain a big smile and chuckle while replying, “Of course you can dear, let me find one suitable for the occasion". I presented to Jim a lightweight house dress with feminine touches and he immediately removed his pants and shirt and donned the dress. “Oh my gosh Jim, not only does it fit you to a ‘T’, but you look adorable!". ‘Thank you Debbie, if feels wonderful when I move".
The painting went well. Jim continued to wear the dress and throughout the project I mentioned to him several times that he looked nice and it almost seemed like he was made to be in a dress. At the completion of the project we cleaned up our supplies and Jim handed the dress back to me. “Jim, I don’t mind you wearing the dress when you work on inside projects... and as a matter of fact I like the way you look in a dress. If you’re interested, I’d like to have you try on some nicer things one evening, maybe when we have an at-home dinner and movie night". Jim agreed it sounded like fun but at first I think I was more enthused with the idea than he.
Over the next week, the thought of Jim in the dress often crossed my mind. I found myself checking the size of Jim’s shoes, and verifying his waist and chest measurements by checking his clothes labels. I could easily make up an outfit from my wardrobe. His feet were a good size and a half larger than mine but I was able to borrow a pair of heels from my mother that might fit.
I won’t wax on about how the night went, perhaps another time, but before dinner, Jim was dressed to the nines and groomed to perfection. In preparation, he was denuded, his eyebrows shaped and he was given a lovely manicure. Only his voice and a few mannerisms revealed his true gender. We had a wonderful dinner and movie night and after a few hours Jim seemed accustomed to his appearance and attire.
Why did I write to Ann Landers for advice? Well, not only did I think the evening was enjoyable and memorable, but so did Jim! Before too long, one evening Jim asked me if he could dress up again and being a good sport I told him of course. I had returned my mother’s shoes but told him we’d shop for a pair in his size and in a style he liked. Jim asked me to call him “Linda" when he was dressed up. I wasn’t ready for that but said “OK". After seeing Jim dolled up several times. I felt a tinge of inadequacy, as Jim was much much better looking than I. It seems my only issue was Jim looked more feminine and charming than me.
So, one day when I was feeling down I wrote a letter to Ann Landers describing what had happened. Much to my surprise, the letter was published and appeared nationally, in scores of newspapers across the country. Plus it was the lead letter in the column that day, so it was seen in print with various titles, such as “He Wears Her Dresses".
Ann’s response, in case you haven’t read it was an about-face from previous year’s advice, as she had begun to change her opinion of cross dressing. While not outright approving or endorsing, she stated her opinion really didn’t matter as long as we were happy, and her advice was to lock the doors and lower the shaders... and say hello to Linda!