I am on a 'spiritual journey" of sorts; a solitary 250 mile bike ride along a nature trail that winds through rural country and small towns along the river. I brought some of Ilene along; my favorite calf-length blue dress (I call her Lady Blue for the floral print on navy); my heels (had to have them), but not a wig (travel conditions too tough) or makeup other than lipstick.
First day I rode about 40 miles to a small rural midwestern town for a stay at a nice "downtown" square off the trail. I checked in, then found a pub about a block down the courthouse square to re-hydrate after my ride; AND to scout the place out.
I returned to begin my minor transformation. I shaved my legs while I showered the sweat and trail dust off my body. Donned my favorite black panties and bra and stocking (thigh highs); and Lady Blue. I accented my abbreviated outfit with my favorite silk headscarf, and my largest gold ear hoops; my Mary Jane heels and splashed on a spray of Chanel. I applied lipstick and draped a shawl (actually my Iraqi keffeyah from the war) about my shoulders....... and I walked out into The World dressed for the first time ever.
I exited the elevator and hotel almost without notice; except for Alex the lobby night clerk. I saw the look of amazement on his face as I glided confidently past him in heels. I was all in, so to speak. The pub down the block I scouted out was nearly deserted, save for one or two tables. I elected for a lone table on the unoccupied outdoor curbside deck, as the evening weather was cool and balmy.
My waitress was excellent, though she didn't know quite what to make of a man in a dress. I wasn't trying to hide much. No makeup (except lipstick). No wig. Clearly a man in a dress. I could tell by her face, though she went about her initial introduction without wavering, that she was struggling with the surprise. She got the attention of her wait staff because I saw several waitresses stream past the inside window to get a gander at the man in the dress.
On her second table pass I put her at more ease. " Donna, darling. You have my permission to ASK, or to laugh; but please do not call the police." It was half in humor, but being in a very small rural town of under 10K, one never knows how the city fathers may react to an open CD. We both had a giggle about it, and no further explanation was required. When Donna delivered my meal and refreshed my glass again, she told me she was buying my second glass of wine (needed). The poor dear was practically in tears, stating she had friends who were gay, CD, trans, etc. (generally weird by her standards, I suppose), and she was so touched that I would come OUT dressed. The sheer act was beautiful to her, and she thought Lady Blue was equally beautiful on me.
Donna gave me a long hug and a kiss when I finished the marsala and paid the bill (naturally with an amazing tip). I was confident on this first-ever trip into The World (dressed), and nearly brazen in carrying out the mission. Donna's kindness and support gave me all the peace and spiritual calm I needed. It was beautiful unto itself. Thanks.
Tomorrow I have a 50 mile bike leg to another cute B&B down the trail. I have Lady Blue, and it will be interesting to see who I encounter when I dress for the evening again.
, Welcome to our forum, When you are here you are home.
...
