Tuesday, January 15, 2019

Dressing Daddy

I mentioned that my daughter gave me a Kate Spade handbag — an early Christmas gift to wear to my former company’s Christmas luncheon.

Christmas morning, she gave me three pairs of jeans. When I finally put on a pair last week, I realized that they were woman’s jeans.

Now that she is preparing to move to an apartment, she is going through her stuff to decide what to take, what to discard and what to give away. As a result, she gave me two Coach handbags, two Jessica Simpson handbags, a Victoria Secret makeup bag and a black pleated mini skirt.

Maybe now would be a good time to ask her to show me how to apply liquid eyeliner. She is very good at it; me, not so much.

Source: Boston Proper
Wearing Boston Proper (Source: Boston Proper)

Vicki St. James
Professional femulator Vicki St. James recounts "My First Time: Getting Caught in a Dress."


  1. How sweet .. and how wonderful to have an understanding, supportive daughter!

  2. I'm so jealous of you ladies who can wear the clothes of your wives and daughters! But some of us are more buffalo-sized and struggle with a good fit. I have large legs, made even larger by problems with edema. Many years ago I found the boot cut jeans at Avenue work very well for me. For whatever reason the women's cut for this style jeans provides more room in the calf, a perfect fit for my "problem" legs. The 32" inseam on the "tall" jeans is also perfect for me.

    For those people who need to be closeted, worry not. Most jeans do not have the zipper installed on the "distaff" side, so for someone to find out you're wearing women's jeans you either have to tell them or they have to see the inside label. While my Avenue jeans have a more feminine sewn marking on the back pockets, nobody has ever made note of that fact, not family members, friends or even my fellow crossdressers -- and I've been wearing them for 20+ years. I haven't owned any men's jeans for nearly all that time.

  3. I loved the link to Vicki St. James story. Perhaps she should have identified herself as the M*A*S*H* character 'Max Klinger' when caught by her stepfather.....