Cross Dressing

T.H. Oughts

Oh the thoughts of Oughts
Joined
Nov 8, 2001
Posts
19,712
Have you ever done it?

Do you want to do it?

Would it be just around home or out in public?

What type of clothes, shoes etc would you like to wear?

Would you shave, pluck your eyebrows or wear fake whiskers?

Would you dress up for your partner if they asked?

Does looking at someone and knowing they are cross dressing turn you on?
 
The SEARCH function is working!!!!!!!!!

This is from your "Chicks With Dicks" thread, THOughts, from a couple months ago.

http://www.literotica.com/forum/showthread.php?threadid=56179&highlight=cross+dressing

cymbidia said:
Crossdresser

This is anyone who wears the garments of the opposite sex. The following link has the best discussion of cross-dressing i've seen on the net, ever. (http://www.yvonnesplace.net/partners/gmatrix.htm)

From another Lit cross-dressing thread:
http://www.literotica.com/forum/showthread.php?threadid=47512
cymbidia said:
It's called crossdressing and i've been intimate with three men who enjoyed it on occasion.

In every case, the man was *not* gay (else what would i have been doing there?) and only one was bisexual. In all cases, however, the men were very secure with thier sexuality and very open to trying new things.

There's something undeniably sexual about women's clothing, especially women's underthings. Men, all men, like to touch when we're soft and lacy and silky... is it such a stretch to imagine they might want to feel some of those sensual caresses more directly, on their own bodies?

Additionally, this is a sexual off-limits area for most men. For very adventuresome men, those very in tune with their bodies and thier needs, therefore, that very taboo can make it more alluring.

For my part, if he wants to wear my panties... and stockings... and garter belt... and anything else of mine... i'll help him get into the stuff. I'll teach him how to roll the stockings on slowly up his legs, the silk whispering under his fingers as it lies against his leg and he twists, trying to get the garters fastened.

Then i'll press up against him and open myself to him. Cross-dressing is sexy and fun and wild and kinky, for me, if it's so for him. But then, i'm drawn to very kinky men anyway.
:cool:
 
Have you ever done it?

Yep. :)

Do you want to do it?

Just like sometimes I feel femme, sometimes I feel masculine too. So I dress the part.

Would it be just around home or out in public?

It's usually not around home. It's usually out in public in some form...I'm more subtle about it if I'm going to random places, but I go all out if I'm going someplace that accepts that sort of behavior as routine.

What type of clothes, shoes etc would you like to wear?

It's a bit more difficult for women to CD as men, because so many things that men wear are really unisex, whereas there is a good bit of clothing out there that is female-specific. I've dressed in full leather, chaps and all, but my favorite way to CD is in a full suit: pinstripe (usually) suit, white button-collar shirt, tie, black shoes. In both cases, I slick my hair back.

Would you shave, pluck your eyebrows or wear fake whiskers?

It never really occurred to me to wear fake whiskers.

Would you dress up for your partner if they asked?

Goes without saying. :)

Does looking at someone and knowing they are cross dressing turn you on?

Sometimes. I know a female to male transexual and before the surgery when she would dress as a he (always), she didn't really do anything for me, but once she started the transformation, she looked really good....er...he looked really good. :) Not that that has anything to do with crossdressing, really :)

I'm more attracted to the idea of male-to-female CDs if they're passable. If they're not it just does nothing for me.

girl, in a sharing mood, apparently...
 
Have you ever done it? Yup

Do you want to do it? Not always-only when I'm feel REAL horny/frisky

Would it be just around home or out in public? AT HOME but once in public (see below)

What type of clothes, shoes etc would you like to wear? Just sexy ladies underwear, Stockings and knickers. (Her bra doesn't fit.)

Would you shave, pluck your eyebrows or wear fake whiskers? No, but I regularly shave my chest and pubes anyway.

Would you dress up for your partner if they asked? Damn right-she knows and approves.

Does looking at someone and knowing they are cross dressing turn you on? No, but knowing I have her undies on does it for me.

I once wore them for a whole day at work (under boxers) and then out to friends in the evening, it was very exciting to know that I had this secret. I couldn't wait to get home and relieve the tension (so to speak)
 
Draco said:
I once wore them for a whole day at work (under boxers) and then out to friends in the evening, it was very exciting to know that I had this secret. I couldn't wait to get home and relieve the tension (so to speak)
I now and then wear my mans underwear. The ought where his crotch was, is now rubbing where mine is :p :p
 
T.H. Oughts said:
I now and then wear my mans underwear. The ought where his crotch was, is now rubbing where mine is :p :p

OH Hell yeah...that THOught drives me wild....:D
 
Last edited:
Oh... very nice, Draco.

A man confident enough of his sexuality to wear something like that on occasion is one hell of a real man, imo. *Nice* legs.
:cool:
 
Thanks cym...now burn your PC...LOL
It'll self-destruct anyway with that kind of image on it....:D
 
Have you ever done it?
Yes.

Do you want to do it?
See answer #1

Would it be just around home or out in public?
Probably just around home. I'm not "passable", not even close, nor am I likely to become "passable". Too chubby, too hairy, and It'd take me forever to clear up my near-permanent five o' clock shadow, never mind the goatee. And wigs almost always look like wigs.

What type of clothes, shoes etc would you like to wear?
Usually "foundation garments"; bodyshapers, girdles, that sort of thing. Stockings (yes, I shaved my legs for them) and the tough part - shoes. I've got an odd-sized foot which makes it tough for me to find MEN'S shoes that fit me right, leave alone women's. But I'd like to find a nice pair of pumps with a reasonable heel. Haven't worn heels since my feet were small enough to fit into mom's shoes.... about fifteen years ago.

Would you shave, pluck your eyebrows or wear fake whiskers?
Think I answered this already in the previous two questions.

Would you dress up for your partner if they asked?
Aw, Hell Yeah!

Does looking at someone and knowing they are cross dressing turn you on?
If they're mostly passable, yeah. I get a kind of vibe off men who are enjoying wearing women's clothing, sort of a vicarious thrill. Women in "men's clothes", well, there's almost no such thing anymore as "men's clothes". (IMO)
 
Draco said:
Thanks cym...now burn your PC...LOL
It'll self-destruct anyway with that kind of image on it....:D
Ah damn I missed the pic! You know my email address Draco :D :D
 
Re: Re: Cross Dressing

SpectreT said:
It'd take me forever to clear up my near-permanent five o' clock shadow, never mind the goatee.
True, if it is only something you might do only once a month, then hair removal would take a while :)
 
cymbidia said:
Oh... very nice, Draco.

A man confident enough of his sexuality to wear something like that on occasion is one hell of a real man, imo. *Nice* legs.
:cool:

Hey, were you looking over my shoulder when he sent me those pics? Cuz he DOES have nice legs. :)
 
SweetCherry said:
Hey, were you looking over my shoulder when he sent me those pics? Cuz he DOES have nice legs. :)
Help me out Sweet Cherry I missed the photo!!!!!!
 
Draco said:
Thanks cym...now burn your PC...LOL
It'll self-destruct anyway with that kind of image on it....:D

Hey, my pc seems to be fine still, so I figure Cym's is safe. Besides, you konw as well as I do how sexy you are. Tho if I catch you stealing all my knickers, I'm gonna have to strangle you with my stockings. :D
 
T.H. Oughts said:
Help me out Sweet Cherry I missed the photo!!!!!!

I missed it on here as well. Damn my body and it's need for sleep. Cheeky bugger seems to be enjoying himself on the boards tho. :D
 
we got a cross-dressing party once every semester :D last time a chick (a real one) hit on me :D :D unforunately I had to tell her that I lend the strap-on to my friend for the night ;)

i made my ex wear a thong, bra (stuffed with good ole kleenex for a nice cleavage), a red silk skirt, stockings and a garter belt, and a black cropped velvet top. we got a dark brown shoulder-long wig, i plucked his eyebrows, gave him clean shave (including his arms), and spent 1h doing his make up....

he on the other hand stuck me in his tux, put 2 tennis balls in the trousers, then we squashed my boobs down with cling film (made me look as if i had a really muscular chest LOL) and he put some fake 3-day-stubble on my face (looked damn real)... he also made me smoke a cigar - it was FUN!

i'm glad we are doing it twice a year... the sight of him in my 7" high heels was just too good to be missed again.
 
LittleDevilWithAHalo said:
we got a cross-dressing party once every semester :D
That reminds me of a pajama party I had about 15 years ago. We ran out of coke so a friend and I went to buy some. He walks into a shop wearing a womans long satin robe... not a problem for him :)
 
I don't do the stuff you mentioned nor do I want to, but I am not ashamed to admit that I have a fetish for women who dress in men's suits and ties, complete with "fedora" style hats. Just something about it, that makes me feel kind funny down there. tee hee ;)
 
lobito said:
I don't do the stuff you mentioned nor do I want to, but I am not ashamed to admit that I have a fetish for women who dress in men's suits and ties, complete with "fedora" style hats. Just something about it, that makes me feel kind funny down there. tee hee ;)

admit lobito, you are as queer as a $2 bill. Why else would your mouth look like a pussy?
 
Unregistered said:


admit lobito, you are as queer as a $2 bill. Why else would your mouth look like a pussy?

ok I'm queer! And you're an asshole. By the way, I KNOW who you are. You're not a very good troll.
 
Unregistered said:


admit lobito, you are as queer as a $2 bill. Why else would your mouth look like a pussy?


I thought the saying was "as queer as a $3 bill"
 
freakygurl32 said:



I thought the saying was "as queer as a $3 bill"

She's from Canada, money isn't worth the same up there as it is here. :rolleyes:
 
Unregistered said:


admit lobito, you are as queer as a $2 bill. Why else would your mouth look like a pussy?

Look Lobito, you got a troll:D I wonder who it could be?:rolleyes:
 
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