Friday, April 27, 2012

[Question] What Kind of clothes do you fancy?

My personal favorite is the Suit.  The Birthday Suit!

What Kind of clothes do you fancy? I know I love latex. Hell everyone knows it! But what kind does love Caitlyn?

This question came in from Alectra (as if the latex comment didn't let you know that!).

I guess like many questions I have to answer this in a couple different ways.

As a person who is exploring cross dressing a bit, I don't have enough experience to say with any conviction what clothing I would like to wear.  I have two pair of panties, and both are very lacy thongs.  It's a big sexual thrill to wear these, as there is little time that I'm not fully aware what exactly I have on under my Levis.  It's not like I forget that I have a thin piece of cloth crawling up between my cheeks, and almost 'presenting' them.  The tight feeling in front is both exquisite and dual edged... it can get me aroused, but there is no place for that arousal to go, which causes a tighter feeling, which gets me more aroused... on and on.  And when out in public there isn't much to do besides finding a bathroom stall so that I can 'adjust' myself.

But as that's the limit of my experience, it isn't fair to say that my favorite type of clothing is tight lacy thongs.  I think I can extrapolate a bit from the experience.  I like them because they are constantly reminding me that I'm wearing something feminine.  They don't let me forget it.  I imagine just about any bra would do that as well.  Three is no male equivalent of having something wrapping around my chest and shoulders that way (A tank top wold be close, but not that tight or supporting).   Stockings and/or a garter belt would be similar as the feeling of something wrapping around my waist (the garter belt) or tightly hugging my thighs would scream out 'feminine'.  Notice I don't say 'hugging my calves'.  I wear light dress socks that can approximate that feeling.

I don't think a skirt would give me the same feeling.  Sure, its completely open at the bottom, but beyond that it would feel like shorts.  Hugging my hips and behind, but having my legs open.  Unless there is a breeze though, I don't see how a skirt would FEEL different.  And a blouse?  Beyond the cut and fit feeling a little different, I imagine they would feel just about like any shirt.  I've worn silk skirts before and don't associate that feeling to purely feminine.  Instead I associate it with 'dressing up'.  Tube tops would be similar to bras... I can't picture much else that I think I would enjoy.

If you want to keep the image of Caitlyn as a sexy redheaded woman, then you might want to not read the next paragraph. Otherwise highlight it to read

Now this is all based on how the clothes feel.  I really don't consider how it would look, as I am a big guy.  I'm over 6'3, have broad shoulders, and at 280lbs I have a gut.  

With that in mind, I don't believe I will ever 'look' feminine.  Add in all the accessories you want (wig, makeup, jewelry, heels...  and I'm still not going to look how i picture myself on the inside. So I don't really worry about how the clothes would look, but rather how they would feel.

But when it comes to captions, I DO consider how it would look.  I think making a newly feminized man look more like a woman, as opposed to an androgynous male, is very sexy! I know a lot of people thinking that would focus in on the breasts, but I tend to focus in on the legs and tush.  And the perfect way to frame that is with a garter belt and stockings.

I don't like all stockings.  Pantyhose is out as it seems to hide as much as it accentuates. Fishnet is out too, or overtly designed stockings.  Those just feel more like a costume to me.  And sorry Alectra... I can appreciate latex in a lot of places, but covering up a woman's legs isn't one of them.  No... I think just straight silky satiny smooth stockings is the way to go.  Adding in the garters and garter belt, just makes me swoon.  Panties are practically optional, as they aren't necessary, but can add to the effect.

Now corsets have a special place in my fantasies, as do chokers.  If I travel over to the more realistic realm, a good femininly cut power suit does things for me too (although that might just be because I imagine those stockings and garter belts under the power skirt).  But none of that compares to my undying love of stockings and garters.

You may wonder why I never really push that out as a preference.  To put it simply; the clothes aren't nearly as important as the mental and emotional impact.   So long as the story is written correctly, I can feel just as happy with a girl in Jeans and a tshirt.  And if the story is written wrong, then the image just doesn't matter.

Hope that answers your question Alectra!

Of course don't forget... if you have a question for me, just type it up into the box over on the right (under "Ask Caitlyn A Question") and I'll try to answer as honestly as I can.


  1. Yup this answer my question and it adds to my further understanding of you.

    I can understand why don't you like latex stockings... May I say there are transparents models, that let you see through? :P

    I tried it before when I was young... more young, and I can remember the thrill of doing something like a Taboo but it was short lived so I didn't keep doing it. As for your preferences I was wondering of whether going silk or something more feminine. I know I sometimes impose my own likings on clothing (latex me) and don't stop for a moment and think something like: If Caitlyn likes sissies, why I don't go up for frilly costumes?

    I'll note that part of chokers and corset. I do like them and I'm a bit confused now, as why I never focused on them in any cap! :P

    I'm not a big expert so anyone with more skills in clothing and couture dresses is welcome to add their points. And I will be glad to read them.

    Hugs and Kisses Alectra

  2. This gives me a great idea for a caption.... ABOUT YOU CAITLYN! (he he he) Give me an hour or two...

    1. Thanks Geofrey! That's a great caption! I'll have to add you to my list or returns and get you something special for that!