[Question] Would you ever meet with someone as Caitlin?

My first Wufoo question!

Would you ever meet with someone as Caitlin for a night of fun? 
To be blunt... no.

But then again 'ever' is a very long time.  Right now, and in the foreseeable future, I have absolutely no chance to 'pass' as Caitlyn.  Not to get into specifics but I'm tall and I'm a 'big boy'.  I have the bone structure of a Line Backer, but I've never played sports (damn docs and their permissions slips!) so I don't have the musculature.  But I am far away from a padded bra, and a corset making me look feminine.

But I also have never given cross dressing a serious try.  I played around with some panties when I was a lot younger, and it didn't do anything for me.  I knew I wouldn't pass, so I never took it further.  Now I am reading and talking to people where its not about passing, its about feeling good.  Thats why you occasionally hear me talk about getting some nice panties, a bra, and some stockings to try.  I don't think it will happen, but I can picture starting there, and moving further and further into full cross dressing.  Getting clothes, working on makeup, getting a wig... really getting comfortable dressing and acting out as Caitlyn.  I would never be a feminine girly girl.

But that wouldn't be the point would it?  I'm not some handsome stud, but I still expect to find a woman that will love me.  So if I was that Caitlyn, I should be able to find someone to love her.

I'm considering doing so...do you have any advice?
I haven't given much thought about this, but here are some off the top of my head.  Now this is on the assumption that you are meeting 'someone special' for a night of fun.

First, just like any meeting you want to be safe.  Meeting someone for the first time in person is a big step.  Now the specific steps may be different for you.  It will really depend on if you are comfortable in your femme form in public.  The one thing I always think of is that meeting in a crowded public place is the safest, but that might not be an option if you aren't comfortable being in your femme form in public.

So it might be best to meet that person without being dressed.  Meet at a restaurant where you can sit and have people all around you, but still have a private conversation.  You can meet this person and see if you feel safe with them.  I believe that reality shouldn't get in the way of a good fantasy.  Your 'date' may want to fully act out you being a woman (and I'm fairly sure you would want to do the same), but the reality is you are a man under all those clothes.  If either of you have a problem continuing on with that fact in the back of your head, then the night is practically doomed to fail.

Even getting to know this person, the night might not progress the way either of you intend it.  So have an 'escape' ready.  Thinking of escape doesn't have to mean that the person is evil and wants to hurt you.  But if the evening just falls apart for either of you, you want the ability to change back to you and leave without a lot of fuss.  So don't meet somewhere and then go to another location with one vehicle.  Have your vehicle ready.  Have your non femme clothes close by, and be prepared to get out of your femme garb without much fuss.

I'm just picturing this... you two hit it off, have some fun, drive over to a motel for a more intimate time, and for whatever reason one of you gets cold feet.  You just aren't comfortable moving forward.  Now you have the awkward situation of one of you being all horny and ready for more, while the other wants to end it.  You have to go someplace else together to get back to yourself.

Now if you want to only meet in private, and don't want to move around enfemme at all, then my suggestion is to book two hotel rooms.  Only tell the person about one of the room where you will meet him in all of your girly glory.  In the other room, have a stash of clothes.  Hopefully you own't need it, and you've only wasted some money for safeties sake.  But if the night goes wrong, and you have to get out of there, you can get out of room A, rush to room B, and change back.

And now after writing all that, I hope its the kind of advice you were looking for.  If you want something different (use a condom, don't swallow, use lots of lube, avoid garlic...) then you had probably better send another question.