This visit to Nashville was just before Halloween. I planned to get as much out of it as I could by doing some sissy shopping in a town where I wasn't likely to be recognized. I went to some dancewear shops to look for some thong leotards and tights. I visited a couple stores and tried on and bought some sexy items.
Anna was going to have some more fun with me. The next night, she invited me along to dinner at a pub where members of this online swing group were going to meet. I wore regular clothes and was a little self-conscious because I was introduced as "Pantyboy," my online handle with this group. Some of them might have remembered my bio that stated that I liked to wear sissy girl things and French Maid uniforms and be humiliated with a strapon, but nobody really said anything about it.
At one point, Anna got everyone's attention and announced that everyone was invited to my hotel room to watch me put on girlie clothes, get spanked while wearing a butt-plug and have to eat my cum. She basically described the whole scene from the evening before in front of everyone at the table. I was red faced and humiliated, especially with men hearing the sordid details. Nobody took her up on the offer, and I felt a little like a little freak.
There was one particularly hot woman there with her husband. They were swingers. She was dressed in an sexy tight dress with black pantyhose and no panties that I could tell. I had been eying her. She did say, "Sorry we have other plans. It might be fun. Maybe I'd have you suck off Jim (her husband). Anna chimed in with, "Oh, he'd love that!" Nothing came of the evening other than I had been humiliated in front of group of about 25 men and women.
The next day I did some more sissy shopping. A lot of times, I'll call ahead and ask if it's OK for me to try on feminine clothing. I also use the call to set up a sense of embarrassment ahead of time. I told the clerk on the phone at this one store that my girlfriend was making me dress up as a girl for Halloween. I could tell she thought that was amusing. She said I was welcome to come in and try on dresses. I arrived carrying a bag with bra, pantyhose, a girdle brief, and high heels. I told the girl I was supposed to make sure it all fit right. She and the other clerk thought it was really funny that I was going to wear everything. I told her that my girlfiend had made me try on the bra and panties at Frederick's. They were laughing at the stories I told her.
They helped me pick out a couple dresses and put me in a room in a closed-off section of the fitting area, so I had the whole side to myself. After I put on all my underthings, I tried on the first dress. They were asking me through the door how things were going, and after I had it on, they told me to come out and show them. "You look great!" she said with a big smile, and she called the other clerk over to see me. I was acting very embarrassed having to wear a bra, girdle, hose and heels. I was walking awkwardly in my heels. I got a lot of giggles as I tried to adjust this very short, tight dress so that the panty line of my pantyhose didn't show.
After trying on two other dresses, with their help I decided on a grey and red houndstooth dress that was obscenely short. Both of them were having fun with me by then, and one said, "You'll have to be careful not to let boys see your panties." They both laughed. I made a comment that my girlfriend had me wearing panties a number of times. The other said, "Better be careful you don't get used to it. This could become a regular habit!" Inquisitively I asked, "You mean if I wear panties too often?" She replied, "Yep, you could start liking it." I said, "Well, I have to say they do feel very nice." They giggled as they rang me up. I thanked them as I left, and they were laughing and saying, "Have fun!"