Feeling daring.

[SissyCharley]

I was feeling a little daring today, so I ventured out into the back garden to hang out our washing, while dressed in my new things including my (very) short mini dress. It felt quite exciting to me, risking one of the neighbours spotting me, but also it felt quite normal to be outside hanging washing wearing female clothes and underwear.
I did not wear my shoes as they would have sunk into the grass and the heels would have made a lot of noise on the stone patio.
I was so filled with excitement I later went and retreived the mail from the porch which is at the front of the house and in full view of the road as we have full length glass doors. I had my shoes on then so had to totter across to do it.

I'm not sure if anyone saw me, there was no one passing by, but anyone looking out of their windows would have had a grandstand view.

More recently I have had more urge to put myself in situations where I might be spotted, I'm not sure why really.
I've also found myself finding ways of bringing the subject up into conversations too.
I was with a customer recently and we got on to talking about our childhood and it turned out she used to play out and about down near a river where my Gran used to take me as a child. I managed to slip into the conversation that my Gran used to have me wear old socks and shoes that belonged to my Aunt when we went out down there as it often was muddy.
She chuckled and made light of it, but it was quite liberating and exciting for me to tell her.
Do any others have similar urges and feelings?

[Ali]

When I first started to explore my sissy side I loved to take risks like you describe. I'd been punished for years by my mother, being put into girls' clothes, and she would sometimes take me out in a dress or skirt. But when I started to enjoy dressing, as a teenager, I loved the thrill of potentially getting caught and exposed.

When I first left home I would put on my most sissyish outfit - a short skirt and frilly knickers that I knew could be exposed because my skirt was so short - and walk around the block. I loved the stares I got.

[SissyCharley]

Was that in daylight Ali?

[Ali]

No, not in daylight. Usually early evening. I wasn't brave enough to do it in broad daylight.

[Kimmi]

Ali, That had to be amazing! Without sisters, I had no viable options for dressing as a girl my age growing up.

How I imagined, though! Short pleated skirts with a half slip threatening to peek out, or going outside with my hair set in curlers.

[SissyCharley]

I've never been out in daylight wearing female out clothes, just underwear.
I have been out once or twice at night.
I once drove home from a friends house wearing a blouse, mini skirt, pantyhose and shoes. I changed in the car, already wearing the underwear and hose. I then had a 5 minute walk from my garage to the house through several well lit streets.
I made it without being spotted, although I did go in the back door of the house.

[Ali]

A lot of the fun, especially in the early days, is the fear of getting caught.

It takes courage to do it (or sometimes too much wine!) but the rewards are tremendous. I loved my first forays out en femme.

Now I still enjoy them, but it's nothing like the thrill of the first times I did it.

[Kimmi]

I feared being caught, and yet also craved it, if being caught meant that I would be dressed as a girl.

[Sissy Renee]

I feared being caught, and yet also craved it, if being caught meant that I would be dressed as a girl.

Kimmi has answered Sissy Charley's original question, at least for me.  I want to be caught because I want to be that girl 24/7, but don't dare.  So I push my limits as much as I can.  How many of us single sissies would love the opportunity to say, "Oh please, Mistress, don't make me wear that in public!", just before stepping outside dressed as we really want to be dressed?  That's why we need the stronger sex.

[Maid Jennifer]

There is no doubt that venturing outside in our feminine attire is daring whether it's just a few feet from the door for a few moments or a quick walk to the end of the driveway or maybe a little further. We all have to start somewhere and once we have overcome the initial fear we realize it's not as difficult as we had imagined and our next time is a little easier. I knew long before I ever went out that it was something that had to be experienced and I was very fortunate to have a Wife who was encouraging but not forceful. I can't imagine what it must have been like for those whose mother's insisted they dress and go out as girls, to me the embarrassment and humiliation would have had a negative effect instead of the positive experiences I had out with my Wife but that's just conjecture, there is no way of knowing how things would have turned out if my mother was the one who first got me into dressing. One thing I do know is having been at this for many years and being comfortable dressing as a maid I often find myself thinking it would be fun if my Wife showed me off to other women. It's not logical to desire to be amusing to women but it's just as daring as my first time in a dress and high heels in public. Go figure!