[Question] wear can i dressup as a woman?

It isn't as much about where... it's about why.

This Question came in from sissyanna:

wear can i dressup as a woman

Before I get into answering the question I'd like to thank you for asking it.  I haven't been sent a real question since June and I really do like answering these!

OK... let's first assume that you intended to ask "Where can I dress up as a woman" instead of just telling me to wear something called a 'can i dressup as a woman'.  Because really... I have no idea what a 'can i dressup as a woman' is, nor where I could get one.  As I hinted at in my tagline above though, that question really boils down to why you want to dress as a woman.

If you want to dress up as a woman for a sexual thrill... to feel the satiny essence of stockings and the tight tug of panties... then the best place for this is wherever you can get the privacy.  Being near a computing device (a computer, a tablet, a smartphone...) would be ideal as it can help both inspire you and set the mood.  You can be playing a video that will help you feel feminine and girly as well as music that lets you be all the woman that you can be.  A bedroom springs to mind, but then again my computer is in my bedroom.  I have my small stash of feminine things (really it's down to a single pair of panties now) hidden in the back of my closet and if the feelings and emotions get to me I have my bed right next to me.

But if you have more privacy, I'd suggest utilizing your entire living space.  Dressing up in front of the computer can be exciting, but it's a whole different experience when you are walking around in your heels and garter belt around the living room or in the kitchen while you pour a cup of coffee.

The last few times I dressed up I was wearing a pair of panties under my regular clothes.  To the outside world I was just going about my insignificant tasks such as watching TV, making dinner, or doing the laundry. But those tasks made me hyper aware of the fact that I was also wearing my lacy frillys.  I wasn't watching TV.. I was wearing panties while the TV played in front of me.  I wasn't making dinner... I concentrating on how the thong felt nestled up between my cheeks while I cooked.  I wasn't doing the laundry... I was mindlessly moving clothes to the dryer while my panties made me imagine being a 50's style housewife.


Now, if you are wearing women's clothing because you feel more at ease expressing your feminine side, then you should dress up wherever you can.  If this is still a secret that you want to keep, then obviously your private home is probably still the best place.  But even then you shouldn't let the fear of being exposed pull you back.  Dress up under your guy clothes and get out of the house.  Sure, the first few times you do this there will be a thrill associated with it, but really it's more about feeling like your true self rather than getting a cheap easy thrill.  If you do it often enough you'll soon realize that most people just don't look that closely at how we all dress.  Do you really think someone is going to notice that you have stockings on under your tube socks and jeans?  Is anybody going to see that you have a bra on under your suit?  Hell... stockings/pantyhose look just about like dress up socks if you only see the ankles peeking out from between your slacks and loafers!

Eventually that thrill and worry will wear off and you'll be left with the feeling of 'being right with the world' even though you are still hiding it.

I guess the hardest reason to talk about is if you are transitioning.  If your eventual goal is to be a woman, then eventually you are going to have to present yourself as one.  To people.  Out in public.   I don't really have any advice to give here... I just haven't let my mind wander enough in that direction to consider all of the consequences.

One thing I would suggest is to have someone that you can share with.  If you are like me, then no one around you knows that you have the desire to dress up and play at, or even fully be, a woman.  The first few times I did any dressing up I was far younger and couldn't share it with anybody.   I never really got past the 'thrill' part of it and couldn't express how it made me feel.  In my later attempts, I had this blog.  Sure, sharing here isn't exactly letting someone experience it with me, but I could at least express my feelings, and by doing so find some more wonderful underlying thoughts.

I can't even imagine how wonderful it would have been to share that experience with someone in person.  For me personally this was more about a sexual thrill so sharing it with my friends and/or family was out of the question.  But if I had a girlfriend?  A trusted girlfriend?  Maybe that could have led to all kinds of wonderful experiences.  My only cautionary advice here is that you have to really trust someone to share that kind of intimate detail with.  While you are in the relationship it might be easy to trust them, but consider for at least a moment if you can trust them after a break up.  Would this woman hold your secret then?  Or would she use this private tender part of yourself as a weapon to hurt you with?  If you can't answer that, then you can't really be that open with them.  At least not until you are ready for people to find out.

So the easiest and shortest answer to 'Where can I dress up as a woman?" is everywhere you can... whenever you can.