First time out in public crossdressed?

[cdstefi]

So my wife and I are going to see Ani diFranco in Coventry tomorrow, and while discussing gigworthy wear I wondered how she'd feel about me going in a skirt. Given that Ani's fandom is heavily skewed to the LGBTQ I get the sense it could be a supportive environment (for context I love crossdressing but have only ever done it in private, I'm not a super loud and proud kinda person).

 

[dougroundup]

Do it and enjoy it!

 

[Mrlighthouse]

Hope it went well!

 

[Cabeza]

So my wife and I are going to see Ani diFranco in Coventry tomorrow, and while discussing gigworthy wear I wondered how she'd feel about me going in a skirt. Given that Ani's fandom is heavily skewed to the LGBTQ I get the sense it could be a supportive environment (for context I love crossdressing but have only ever done it in private, I'm not a super loud and proud kinda person).

I think it would be fine and really empowering. I’m a little jealous

 

[SissySalina]

First: did you go in a skirt?
Second: How did it go?
Third: would you do it again?

PS: Nothing like the first time in public!

 

[allboutgspot]

Are you passable?

 

[wifes_fag]

I was like forced to dress by a guy we were seeing. We were in our mid twenties and I looked good with a wig. I especially remember my first time. Going out and getting in the car wondering if any of our neighbors seen me. my wife drove the fifteen miles or so. My mind was wandering, looking down at my bare legs with a skirt laying across them. I knew this would probably become more common for me now. More requirements. I was so nervous going through the hotel lobby. people were actually seeing me in a dress. Nobody stared. I felt better. We made it to the elevator and got in. I got towards the back. A middle aged woman got in with us. I thought oh my. We got off uneventful. Finally made it to the room. He was very pleased . Then he gave me a twenty and told me to go get some wine coolers while he fucked my wife. And told me to think about why I was wearing a dress while going. My God. He put me right out there. I went to Walmart and sat there thinking. Finally I opened the door and walked in and went and got a 6 pack of wine coolers. No self checkouts back then. I just knew somebody was going to say something but didn't. I was so relieved when I got back and in my car. It really hit me that I was now a sissy cuckold.

 

[Nicolewilson]

First time out in public was quite young as sisters dressed me up and loved it . Luckly I looked feminine and people just thought i was a girl .must admit I was a bit nervous but calmed down and enjoyed it .Been out loads of times since to shops and straight venues and not had any problems .

 

[Justusnluv]

I was much older my first time out in public. A Man had convinced me as my wife's cuckold we would both be happier if I was her sissy. My wife happily agreed. The first time dressed as a man but out per my brides instructions. To buy heels. The sales girl was so wonderful. Asked me to come by and say hi when I was dressed. A few weeks later I was sent out to run errands dressed. Btw, the sales girls thought I looked great. Bought another pair of heels. I have never been a nervous or shy guy, but I was as a girl. I did have a man give me a compliment as I pumped gas.
Eventually, I became much more comfortable. Shoping alone and with my wife. Eating in restaurants.

 

[Jessica616]

My first time was a few years back on a business trip. I ended up going to a local LGBT bar close to my hotel. It was a slow night, but still had fun. Lately I have been going out more by taking walks and even shopping. It has built my confidence greatly.