The most daring

[Sometimes Steffi]

I did a lot of things that were a stretch for me. But, I think the biggest one was when I kissed a girl, and I liked it.

I was at the Keystone Conference at the Saturday night Gala Ball. I was wearing a sequined cocktail dress with all the fixings. This (CD) girl asked me to dance, and we ended up dancing the rest of the night together. After the dance was over, everyone was headed to the elevators to go to the bar or back to their room. Just as we got to the elevator, this girl I was with said, "I wasn't going to take my panties off for you, but I would have liked a kiss." How's that for a pickup line? Without even thinking about it, I replied "A kiss, I can do a kiss." Then, she came up to me and gave me a kiss on the lips. She turned to leave, but came right back for another kiss, and then another and another. And, that quickly, I was making out with another girl right next to the elevator while all the other girls were just walking right past us.

I guess I liked it, because I just grabbed her hand and said, "Not here." I led her through the outside door that lead to the parking lot. We were making out right outside the back door to the hotel. We must of made out for about 15 minutes, and it got into some heavy petting. She slipped her hands under my dress and grabbed my butt. Then ... Wait. Wait. Why am I telling you this. Good girls don't tell, and I was a very good girl. I've got nothing else to say. Forget everything that I said.

[MonicaPVD]

Steffi, you're going to get yourself banned from this sequined sanhedrin of ours. 🤣

[Sometimes Steffi]

Oh, did I do bad. I thought it was pretty clean, but I can edit it or delete. I didn't intend to go against the rules.

[Sandi Beech]

Haha, funny.
I actually have an R rated story but left it out since Monica said to keep it PG-13.

; )

Sandi

[Sallee]

I went to the Costco Food court. NO problems at all. And I have gone to many womens dept dressing rooms to try things on Again no problems. Years ago when I was a young good looking CD I went to a straight bar near my college which had a band, Bar tender asked if I want a drink ordered a beer then as I was standing there someone asked me to dance WOW I declined. He turned away disappointed. Really I have never had a problem in most situations. Its just getting the nerve and dressings appropriately
I still want to get the nerve to go to a casino. I guess my biggest fear is that I would win big and get noticed because of my big win LOL

[SIZE=1]- - - Updated - - -[/SIZE]

that was very gutsy If caught you might still be there

[lingerieLiz]

Went to a drive-in with a friend for a rock n role contest. I was the girl. My sisters had taught me to dance as a girl. I was young and passed at the time.
as

I went to a costume party as a nurse. I wore a white nylon nurses' uniform dress which were popular at the time it showed my nylon slip with a lace bodice, lace bra, panties, garter belt white stockings and white nurses heels. Wore a nice wig and nurses cap. Got hit on by a couple guys. Some of the girls came up and said, you have been practicing. One suggested we get together.

I've been an adventurer all my life.

[Misty_cder]

My most daring was when I wore women's jeans with 2-inch block heel boots to fill up gas late one evening. I had the jeans over the boots, was wearing a gaff to get the smooth look, and had on a regular men's polo shirt. This was my only time out openly wearing woman's clothing.

[Vintage4sarah]

Back in 2013, I remember a special autumn afternoon and evening when Sarah would find the courage to do three new things for the first time. I was away on a trip a day early to give one of my historical battlefield tours and booked a motel room. It would have been a usual night for Sarah in the room, but this time I explored new activities. The first was meeting and chatting with a local crossdresser I met on the net earlier. He was on the way home from work (dressed as a guy) while I was all done up as Sarah. Just some innocent chatting and photo swapping before he had to leave. The second was my first attempt at going out as Sarah for a stroll and do some window shopping of the downtown area. I would then go to get some "take out" for my evening meal. Everything I did that night was new and far easier than I thought it would be! Finally, I knew that I could pull this all off with ease even though, my inside was all butterflies at first.

[Jennifer_Ph]

A bikini in public. Was so fun.

[cdinmd206]

My first time going out fully dressed was at Halloween and going out as a french maid to a CD friendly bar in Washington DC, but my most daring happened by accident. A couple I knew who also knew I cross dressed asked if I wanted to go to the gay pride day in Washington DC. I said sure and the wife said I should fully dress. I dressed but that was back in my dress like a days and I wore and extremely short skirt with my usual stockings, garter belt and panties under it. Blouse with my big boob forms and a long blond wig plus heels. I thought we were going to drive to the area of the festivities and park close by. When I got to the couples house I found out the plans were to drive to one of the DC metro stations and take the metro in. I had never been in public fully dressed in daylight and had never thought about using public transportation. When we boarded the Metro train I was as nervous as a nun in a house. We had the metro car to ourselves until the first stop and a black family got on. The mother looked me over and said nice legs and the teen daughter piped up and said look mom he is wearing stockings and garters. I was ready to climb under the seat, but the mother quickly said you must be going to gay pride day. We had an interesting conversation the rest of the trip and I had a wonderful day walking around in public in the daylight for the first time. Attached is a pic of that day. The lady os the wife of the couple I went with.

[kimdl93]

I have never done anything that wasn?t G rated in public. The thing I found most challenging personally was attending a business meeting with a GG colleague in girl mode without giving any advance notice. It was a bit impulsive, as I had made the appointment to meet with her without any prior consideration. When the day came, I realized I had scheduled a mani-pedi just a couple hours before our meeting and found I just couldn?t bring myself to wreck my nails or change back into male mode.

[ColleenA]

The most daring exploits are each time we push our confidence to new adventures.

That, to me, sums it all up.
For decades (literally), I could never imagine being en femme out in public, mainly because I cannot pass under even the lightest scrutiny. The most I would do was stand out on my front step around midnight and breathe in the fresh air.

In 2015, though, I decided to really give it a try - under the "protection" of Halloween. Actually, I went out on the 30th and 31st (a Friday and Saturday) to Kohl's at about 9p.m., when it was dark out and fewer people should be at the store. Still, the chance to be out and to simply browse through all the clothing - especially the lingerie section - without worrying that somebody would peg me as a perv was both mind-blowing and liberating. (I did take the precaution of keeping my distance from any other woman in the area.) I did not buy anything either night. Also, the first night, my gf went with me, and we stopped at Denny's after leaving Kohl's. The second night I did my first solo outing.

The next year, I again did two evening shopping trips, but this time I bought two dresses. A woman buying dresses? Whoa! Stop the presses! For me, though, this average event was another huge first. And I felt bolder; the day AFTER Halloween, I ran errands in the daytime with my gf. We ate lunch at a restaurant, picked up some items at a pet store, then went to Kohl's, where I bought a pretty pair of panties. Without the protection of "it's a costume," I did get a couple of dirty looks, but I held my head up and went about my business.

Now I try to take off the 29th through 31st from work each year to have whole days out. One small benefit is I can leave my nail polish on for three days in a row. My most common activity is shopping. I will go to Macy's, Nordstrom Rack, and other department stores (some have enormous clearance sections), as well as thrift stores. I have bought skirts and blouses, makeup and shoes, panties and bras. Other activities have included normal, daily stuff - lunching at a diner, hitting the grocery store, and picking up a prescription at Target.

If you have never gone out en femme, believe me when I say it is amazing how much little things can boost your self-esteem. The first time having someone call me "ma'am" or overhearing the word "she" applied to me sent a thrill through my body - it is so validating. One time, a woman caught my eye as we passed; at first she just smiled, but then she stopped to compliment me on how I looked (ok, she clocked me and kindly gave me encouragement). Often, though, store clerks interact with me as they would with any other woman, despite my "knowing" I am not passing. Each year, I have to work at setting that mental block aside.

One funny moment was when I was at a mall and asked to have a skirt held for me while I continued on to other stores. The lady asked me what name to hold it under. I stood like a deer in headlights. It took at least 6 seconds before I stammered out "Colleen;" that is an eternity for such an innocuous question.

Other milestones: 2017 - first time in the women's dressing room (exhilirating).
2019 - ONLY time in the ladies' room (too stressful; will stick to gender-neutral restrooms, such as at Target). First mani-pedi (awesome). This year, I again went out after Halloween - this time on Nov. 4 for a bra sale at Sears that I had passed up days earlier.
2020 - besides looking through the lingerie sections of department stores, this year I was at an outlet mall and shopped at the Victoria's Secret, Hanes, and Maidenform stores.