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As many of gurls may have started out, I’ve been dressing in ladies lingerie for years, secretly. Loving the feel of the smooth fabric against my skin, the look in the mirror. It started out as a hookup in nylons. I found myself so aroused at the look and feel that I progressed to full on dressing. Fast forward to 2017. I was in SF, my favorite LGBTQ city as I had been here lots of times and enjoyed many a time!
I had my wigs, panties. I longed to go out in public dressed in this “accepting” city. I went to Macy’s, scared, to try on dresses. I picked 4 I really though would look good on me. I went to the ladies dressing room and tried on a few…none really looked that good on me. I came from my room, and got a little surprised looked from a mom/daughter also just coming out. I went back to the racks, and found other dresses…I really wanted my own dress! I decided to go over to a less traveled department, the wedding area. I asked the clerk if I could try the dresses on, and to my surprise, she said absolutely. It felt great to find a dress, that both fit well, and looked great at the same time. I picked one, and checked out. I now need shoes and pantyhose.
I went to the shoe department…a little embarrassed looking at ladies shoes. A man and woman clerk came over to assist; “what size does she wear?”. I replied, ” they are for me, I have a special event tonight”. Only a slight bit of observed surprise from both of them. I showed them my dress, and they showed me a 2″ heel that look beautiful. As I gave them my size, the female employee went back to get my size. It fit, and looked great. As she boxed them up and proceeded to the register, I just sat there…and cried! WHAT AM I DOING?? when through my mind. Not a full ball-out cry, but tears streamed down my face as I contemplated what I was doing. The lady, sensing a need to comfort me, came back over to me and said, “you will look beautiful tonight!” I wasn’t even dressed, just me, a man in jeans and a dress shirt. I was relieved at the reassurance that someone thought enough to encourage me like that. I left the store with a new dress, new shoes, and pantyhose for my night at Diva’s
The time had come to get ready. I had “prepared” in case I got picked up by a handsome man looking for a little fun later. I put on my makeup the best I could…hands shaking…I had done this a dozen times…why was I shaking so? I put on my wig, my earrings, matching necklace. I slipped into my flower dress, and slid on the pantyhose. Hmmm, the pantyhose seemed a little small 🙁 I left them on anyway and put on my heels. I picked up my sparkly-silver clutch and admired myself in the mirror; I do look good. Now the test.
I left the hotel incredibly nervous! I’ve been in public in lingerie, nylons, and panties before, but not noticeable under my manly street clothes. I decided to walk to Diva’s as it didn’t seem that far. As I walked down the sidewalk, the cool SF breeze blew up my dress and over my lady parts. Tonight, they were lady parts! I was horny, excited, and elated all at one time. It felt so wonderful. As I walked..and walked..and walked..I realized my ankles were really starting to hurt. After about 1/4 mile, my pantyhose, being too small, began to rip at the crotch. Finally, not being able to take my ovaries hanging out, I stopped and took off the pantyhose and threw them in a trash can. Now, no pantyhose, and no panties…I got excited about that feeling, for some reason, and I liked it.
After walking a mile, yes a mile, I got to a familiar part of town and Diva’s. My were ankles bleeding slightly from the shoe buckles. I got to the door and a friendly lady met me for the entry fee. She complimented me on how good I looked, and remarked, “very classy”. Later, I realized that every employee and dancer was trans. Some truly did not look like it; wow! I watched several girls dance on the polls and on the floor. I’d been to lots of strip joints before…but me as a woman, watching women dance, was getting me turned on..it was fun, naughty, and exciting. To have so many emotions running through me at once was hard to balance at times.
After a few drinks, all cash I might add as CC not accepted, I had to pee. One bathroom, no door. I figured “whatever!”. I pulled up my dress and sat my bare ass on the toilet peeing like a good girl. As I was finishing up, and gentleman arrived at the door, apparently surprised to see someone there. He quickly said “excuse me” and left. Wow, that felt wonderful; did I pass for him?
The night went on for another 2 hours until I ran out of drink cash. I was NOT walking back to the hotel. I hailed a cab, and got back to the room. I was disappointed that I was not hit on, so, I had to taking care of myself. Thinking about my night, my emotions, my first time out…let’s just say, I went to sleep not long after getting back to the room.
I think of that night often, and look forward to doing it again!
-Jasmine
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