Mild/Medium public risk
 

I am interested in learning some mild to medium public dare for sissies/crossdressers that is a bit riskier than complete hidden public. I've been crossdressing secretly for many years and recently explored some hidden public dressing dares: things like tights under ripped jeans, bright colored sports bra under thin shirt (jogging) or panties under leggings (biking), painted toenails and perfume ...etc. I've also tried talking a walk just around the block at night fully dressed, but only made it half way. I would like to learn some ideas on how to push the public/risky aspect a bit more.

Likes and fears:
Putting these together as they are kind of intertwined here. Love the nervous/embarrassed aspect of not knowing if/when people will caught or notice me dressing. For example, its scary but also a turn on knowing that a car could pass me while biking, people could see me while jogging, or people in the corner store can notice me dressed.

Limits:
Not really interested in forcing/imposing on any specific person or explicit flashing in general. So things like "Spread your anus right in front of the first person you meet" or "Asking each person you pass by to watch you jerk off" are not good. Also the limits in signature.

What I have:
Since I have been dressing and playing behind closed doors for many years, I have most common things: makeup, wigs, lingerie/underwear, tights, heels/boots, dresses, tops/bottoms, workout/swimsuits ...etc, and I am willing to purchase and recreate looks when I don't already own them.

In terms of toys: plugs (3 sizes), chastity, wands (2), dildos (3, from 6in to 11in), gags, locks, and also willing to explore other toys that I don't currently own.

General locations:
Live on second floor of an apartment complex. Smaller town. Many small parks around, and some tennis/basketball courts. Lots of quieter roads in the residential areas, especially evening. A few blocks from the main streets where commerce happen (restaurants/groceries/pharmacies/theater...etc). Can be more specific if inquired.

If you have access to a car, go driving crossdressed. Do it at a time if day you find comfortable and a length of time you find comfortable.

I don't currently own one but if I do that will definitely be something I'd try. At the time I drove often I wasn't courageous enough to go out dressed, but now I probably would.

Shamelessly bumping in hope of getting some ideas or conversation going.

Hello Kylie and very much respect you in touch with your girl persona and the courage of do it.
I very much share some of the your fear, doubt, and desires!

I link this at you for some ispiration if you like:
https://www.getdare.com/bbs/showthread.php?t=401265

take care
sabina

Why not take your crossdress clothes with you into some male public toilets. sitting in a cubicle, gett dressed then sit and listen to people entering and leaving. If you wish to go further, unlock the cubicle for a bit as you sit there

A fun one I've always wanted to do is to go out and hide your housekey (or another small, important object) somewhere where it won't be found. Then, late that night (midnight or after), after getting yourself horny (but not cumming) for a while, get dressed as sexy as you dare and go out to retrieve the thing you hid. Having an objective makes it much easier to go out.

A variant of this I've done (and really love!) is going to the top of a parking garage in CD, then dropping my car key over the edge. Then, I had to go all the way down and up, past all the cars, to get my key! It was when Covid was worse, so there was no one there, but it was still super exciting. But, since you don't have a car, maybe this won't work so well, unless you have a way of locking your girl clothes on so that you have to retrieve the key in order to get dressed in your boy clothes.

Another, more hidden idea, is to put in your plug and chastity, then wear a gag under your face mask, then go for a walk! Super simple! And, even better if you walk to the pharmacy and buy lipstick with your gag still on under your mask.

Finally, and this may be too much, is pretty simple: put on one of your dresses, go to a basketball court late at night, and lock yourself to a fence or the basket. Even if you click the lock and immediately unlock it and go home, it will be so thrilling! Even better if you take a selfie (even if you never share it), so you can see how excited you look when you closed the lock.