An opportunity arises

[JocelynJames]

So my wife has a work thing tonight and I mentioned I might dress and go out for a ride , to which she replied ?oh cool ?. I know some of you have done this , so without doing anything too risky, anybody have any additional suggestions on what to do while out. Even if it seems mundane, i don?t go out dressed often so it?s all kind of a novelty. Thanks

[Sandi Beech]

I say go to a drag show, not so much to watch the show, but to meet and talk to the people who go to them. There are generally more women than men and pretty much all are accepting or they would not be there in the first place. I have had shockingly good times doing that. Sometimes I don?t even go to the show. I just sit at the bar so when the show lets out there is a crowd of fun people to hang out with and in some cases dance with depending on the club.

Sandi

[Marketa]

Just as Sandi said, or you can go to some jazz bar or something like that. If it's a safe area you might take a stroll and enjoy just being out. When I'm in the city I usually walk more even when I could take public transport, because it simply feels great.
But either way realise you're most likely going to be out for few hours so choose shoes you can make it in outside. If you're not used to go out often, as you mentioned, then I would highly recommend to leave stilettos at home, or at least bring spare comfy shoes with them.

[kimdl93]

Depends on how long you want to be out. As reported here, I often visit a local coffee shop or wine bar. Sometimes I just check out the cute little shops on mainstreet, or pick up some groceries. Nothing particularly exciting, but at least I am out among people.

[Helen_Highwater]

If you're still in the baby steps stage then I'd say a drive through fast food meal might be an option. You get an interaction with someone, often they take little or not notice of who's at their window so it's safe but somewhat exciting. A short walk to post a letter, one you've written to yourself so later on you get a memento of the event. Get money out of a hole in the wall is another.

[alwayshave]

Joss, depending how close you are to the city, I'd go to a LGBTQ+ venue.

[Jodi79]

If you are wanting to keep it low key find some walking trails to enjoy. If you feel a little more adventurous find a small shop to go enjoy. Maybe a clothes shop to browse

[docrobbysherry]

Don't forget your wallet! I carry mine in my pants. When I did what you're doing for the first time 25 years ago a cop was behind me and I realized I'd left my license at home!

No, he didn't stop me.

[Rochal Tukque]

Take a friend or make a friend.
Rochal

[CarlaWestin]

This answer is a little late but may serve you well for next time. I used to go out for a drive while dressed very extreme. Heels, stockings, boobs, leather skirt, tight top, etc.
I would put gas in the car and then pay inside the store if there was a female attendant. When my wife had evening events, I would go perusing around the local mall dressed to get video.
You can be out in public all day and no one even notices unless you push the issue.

[April Rose]

Wish I had known about this earlier; you could have come to my house!

[Jennifer2918]

If you're still in the baby steps stage then I'd say a drive through fast food meal might be an option. You get an interaction with someone, often they take little or not notice of who's at their window so it's safe but somewhat exciting. A short walk to post a letter, one you've written to yourself so later on you get a memento of the event. Get money out of a hole in the wall is another.

I started very late at night going through drive-thru fast food establishments. I found out that a high percentage of the time, it was the same workers and they were bored to death. They would love to talk and it was always a positive event. Then, again very late at night, I started going into 24 hour donut shops. Just go and buy a donut. The people are friendly and it was also a positive conversation. No one judged, just positive vibes all around.

[Stephanie47]

Except for Halloween my outings were limited to strolls in a safe residential neighborhood that has a shopping area of small shops and restaurants and two grocery stores. Halloween is approaching so there are opportunities for greater expression of self. On Halloweens I would be totally en femme with makeup down to heels and hosiery. I am a "dresses only girl" so it was a pretty dress with all the proper undergarments: bra, panty, slip. Those were the only times I would force interaction with fellow humans. Over the decades I wished there was a local social group, but there were none in my area.

[Fiona Lindum]

I have been to the drive through food outlets, but one of my early outings was shopping in a supermarket.

[TheHiddenMe]

Casinos. I know they exist in Massachusetts, I guess it depends on how close you are to them.

They are always open. They have security and usually lots of parking. Adult drinks and time diversions. People dressed in all sorts of outfits. I have been in multiple casinos in different states (Illinois, Missouri, Ohio, Pennsylvania) and never had an issue.

If it's earlier in the evening, go to the mall. These days, there is no one there anyway, so you can park close by and walk around and window shop.

[BLUE ORCHID]

Hi Jocelyn James , It's been 12 Days now, So how did it Go, ???

[JocelynJames]

Thank you for all the suggestions , ladies. Sadly, I never even dressed. My mom had a health condition arise instead , which of course took precedence. I?ll have to try another time.

[VS Fan]

So sorry Jocelyn! It won't be the last opportunity! But I know what a bummer it is to miss one. There have been times when I've had plenty of time to dress and for whatever reason just never got up and did it. Life, etc sometimes gets in the way, but there were just as many times when I was glad I didn't get dressed because of a random FaceTime call from one of my daughters :D obviously I wouldn't have answered and called them back, but I love it when they call of course.