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 DAVE632
Joined: 6/17/2006
Msg: 126
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Have You or would You consider Dating a CrossdresserPage 7 of 8    (1, 2, 3, 4, 5, 6, 7, 8)
Date a Cross Dresser. Sure. All SHE ever wore were Jeans, T-shirts and cowboy boots and, hell, she looked FINE in all or any damn combination.



I 'specially liked JUST the boots but then I'm a little kinky anyway.
 knoxman
Joined: 3/24/2007
Msg: 127
Have You or would You consider Dating a Crossdresser
Posted: 3/28/2007 7:07:08 AM
The only time I want to see a woman wearing men's clothes is when she's wearing my shirt(and nothing else) the morning after....you know.
 blackmaleya41
Joined: 7/2/2005
Msg: 128
Have You or would You consider Dating a Crossdresser
Posted: 4/7/2007 7:27:44 PM
Wasn't it Freud who stated, "I must admit I don't understand women". If Freud couldn't understand women, how could he understand the mind of a cross-dresser?

I had to do a lot of research on understanding a cross-dresser (counseling for a friend) and I can tell you the division they feel inside isn't pretty.

I suggest that you might want to do more research on the subject, and keep an open mind.
 Lakeland Florida
Joined: 3/27/2007
Msg: 130
Have You or would You consider Dating a Crossdresser
Posted: 5/4/2007 12:21:58 AM
05-04-2007

I think you know his real issues. No need to cry later. He like guys and you know it. Why set your self up for failure? You already know.
Go with what you know is the right thing to do. Save your self for a man who would be happy to have you.
 kitty_kelly
Joined: 4/13/2005
Msg: 141
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Have You or would You consider Dating a Crossdresser
Posted: 1/21/2008 1:05:15 PM
Yes. If he was straight.

Men were the first to wear high heeled shoes, it was the fashion (most women seek out taller men which is why men started doing this) This is really a fashion question more than than a sexual question.

As a woman I wear pants and at one time that was not socially acceptable. I also feel great in a garter and thigh highs after I have just shaved my legs. Why should a man not enjoy the same pleasures?

One thing I do not understand about this issue is why do some cross dressing men have different names?...this would tell me they are not comfortable being themselves. They have to be someone else to be okay in their feminine clothes, this is not a good sign in my book.

Eddie Izzard is one of my favorite people and the "executive transvestite" definition is what I am referring to when I say yes to this question.
 wildtranny
Joined: 1/7/2008
Msg: 143
Have You or would You consider Dating a Crossdresser
Posted: 1/21/2008 8:39:30 PM
I am a 25 year old crossdresser and love the fact that my g/f is alright with me dressing. Dressing makes me feel sexy and confident. Everyone thinks I look hot as a girl.
 Shylent
Joined: 10/2/2007
Msg: 144
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Have You or would You consider Dating a Crossdresser
Posted: 1/22/2008 7:58:36 PM
Perhaps this should be in "ask a girl"
Since it is not it depends.

Male crossdress no, sorry not into blokes.
Female crossdresser sure! whynot
Would me that i wont have to worry about my g/f getting hit on when we go out unless we go to a gay bar. in that case we both would have to fend off suiters.
Unfortunately all the female crossdressers i now also happen to be lesbian
 Tinathegreat
Joined: 2/5/2006
Msg: 150
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Have You or would You consider Dating a Crossdresser
Posted: 2/15/2008 8:17:07 AM
I wouldn't mind either. Sounds like it could be fun.
 sub girl wanted
Joined: 5/1/2008
Msg: 151
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Have You or would You consider Dating a Crossdresser
Posted: 8/8/2009 5:15:20 AM
Id be more into a transsexual...some are incredibly gorgeous.Im pretty open minded,however not attracted to masculinity at all.But if a male can make himself look damn good,id check it out
 srb272007
Joined: 3/12/2007
Msg: 155
Have You or would You consider Dating a Crossdresser
Posted: 8/8/2009 8:19:00 PM
lol @ applepie

one night at the bar this very tall attractive blonde walks in

then she gets a little closer and in my mind i say "oh its a dude" just as somebody else says very loudly "its ahhh duuuuuude" lol

also no
 Cat*Eyes
Joined: 9/13/2006
Msg: 156
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Have You or would You consider Dating a Crossdresser
Posted: 11/19/2009 10:26:58 PM
I NEVER would I date a cross dresser. I like MEN who LOOK like MEN wearing 30 inch waist jeans and tight black shirts with longer hair. I would like to see men wear eyeliner, but I do NOT want to see men dressed as women or wearing their make up like women, or wearing wigs like women. I really want men to wear eyeliner but the way the man rock stars do. I do NOT want men wearing make up the way Boy George did. That was too much like a woman. I want men who look like men with a man's way of wearing eyeliner. Everyone, men and women should wear eyeliner. Male rock stars do. Eygptian men and women including male warriors wore eyeliner. Eygptians in the day of Marc Anthony and Cleopatra loved cats too. Men looking like men with Eyeliner and loving cats, I like that.
Strange, but I am aware, cross dressing men are usually sexually straight as there have been men of this type who have consulted with me, to help them with their "look". I wrote them advice, but I NEVER would be interested in meeting them. I want men dressed as men and looking like men, as I already stated.
If there are want to be rock star men who want to consult me for their look or have me professionally help them with their look in person, I am a licensed Cosmotologist. Crossdressers, I will write you but never be interested in meeting you. Men who want to have that man rock star look, that look like men, this interests me.
 windloverr
Joined: 2/29/2008
Msg: 158
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Have You or would You consider Dating a Crossdresser
Posted: 11/19/2009 11:38:25 PM
I LOVE cross dressers!!! Seeing a woman walking around the house wearing one of my shirts... just saying...
 SoSoSuave
Joined: 11/3/2009
Msg: 160
Have You or would You consider Dating a Crosstresser
Posted: 11/20/2009 4:49:53 AM
I've never tried on women's clothing, but it could be fun I think.
 mari1216
Joined: 3/21/2009
Msg: 161
Have You or would You consider Dating a Crosstresser
Posted: 12/4/2009 4:26:58 PM
I dated a cross-dresser. A piece of cloth does not change who a person is within. I had no problem with it and would date another CD if it came to be.
 cherryyblossom
Joined: 7/19/2009
Msg: 162
Have You or would You consider Dating a Crosstresser
Posted: 9/26/2010 5:51:29 AM
the way someone dresses should not affect on how other people view them as. Some women do not like to wear typical female clothes (i.e. skirts, dresses, tights) and some men like hate to wear men's clothes (baggy, loose fitted clothes, sneakers, shorts). It does not change who they are.
 Chazz44
Joined: 6/3/2009
Msg: 163
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Have You or would You consider Dating a Crossdresser
Posted: 9/29/2010 10:33:36 AM
As always, gender and sexual orientation remain confused in most people's minds.

Clothing is a gender, not a sexual orientation issue. Otherwise, lesbian "femmes" would all be "straight".

As to fetishism....

Definition of FETISHISM (Merriam-Webster)
- the pathological displacement of erotic interest and satisfaction to a fetish (fetish: an object believed to have magical power; a material object regarded with superstitious or extravagant trust or reverence.

By this definition, phallusism, racism, sexism and homophobia are fetishist exercises. Why? Because they assign magical power and reverence to penises, skin color, oppressive sex roles, and only one kind of sexual expression.

If nothing else, this thread confirms the power artificial, culturally enforced, gender roles (fetishes) have over people's psyches. Is there any doubt why sexism , homophobia and racism, to an alarming extent, are still culturally sanctioned pathologies? ....I think not.
 Chazz44
Joined: 6/3/2009
Msg: 164
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Have You or would You consider Dating a Crossdresser
Posted: 9/29/2010 4:10:25 PM
I rest my case....
 showermate
Joined: 12/23/2014
Msg: 165
Have You or would You consider Dating a Crossdresser
Posted: 5/21/2015 11:44:15 AM
Yes I would love to

We are all humans and have the right to do what we must to feel good in our our own skin.
I have met people of all gender and persuasion and some of the most beautiful and intelligent individuals I have met have been cross-dressers or Transsexuals.
If you feel beautiful and happy as who you are then you tend to attract others who feel the same themselves.
Thus yes...I have met a few that I have felt an attraction for and would be inclined to enjoy personal interaction with them.
The human body is a sensual sexy work of art to enjoy in every way.
 InnerGorilla
Joined: 4/1/2014
Msg: 166
Have You or would You consider Dating a Crossdresser
Posted: 5/21/2015 1:19:28 PM
How about the other way around. A girl that likes wearing men's boxers... Or army boots.
 tgif333
Joined: 4/16/2015
Msg: 167
Have You or would You consider Dating a Crossdresser
Posted: 5/21/2015 3:24:02 PM
give me one good reason why I should date a person of this ilk.

just one that makes sense.

I think it would be uncomfortable and embarrassing.
 springorfall
Joined: 5/17/2015
Msg: 168
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Have You or would You consider Dating a Crossdresser
Posted: 5/24/2015 7:44:38 AM
Crossdressing isn't one of the qualities in a man that I'd have at the top of my preference list. Then again, I do find Eddie Izzard v attractive - of course his intelligence, wit and sense of humour don't hurt, (:British understatement) but I'd date him for sure, and he walks better in heels than I do :) Thinking about it, I think it actually might be quite fun sometimes going out with him looking one way, sometimes another, and I do appreciate a good makeup job!

It'd need to be an upfront thing though - finding out by accidentally walking in on him after we'd decided to be together wouldn't be good... like if I suddenly revealed I had kids (I do) or a pet unicorn (I don't) - it's all a part of being open about who we are so we can make informed decisions
 CrookCatcher
Joined: 7/14/2014
Msg: 169
Have You or would You consider Dating a Crossdresser
Posted: 5/24/2015 9:58:09 AM

How about the other way around. A girl that likes wearing men's boxers... Or army boots.


Damn skippy.....if Christie Brinkley ever gets around to returning my calls I'll be fine with her in wranglers, work boots and a flannel shirt, heck throw in the wife beater t-shirt and boxers as well. I'll manage.....somehow. :)
 dwmitch
Joined: 12/31/2009
Msg: 170
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Have You or would You consider Dating a Crossdresser
Posted: 6/6/2015 11:08:49 PM

How about the other way around. A girl that likes wearing men's boxers... Or army boots.


I'm not sure about the boxer shorts, but women wear men's clothing all the time. I'm not talking about stuff that until relatively recently was considered men's clothing, such as jeans and t-shirts, but clothing they actually got from the men's department of Walmart or Target.

My ex girlfriend (the second one, actually) openly admitted that her pants were from the men's department because they fit better. When I was talking to my mom about that she said that other than her church/work pants she gets a lot of hers from the men's department. I've even seen her wear some of my jeans that I've outgrown years ago to go shopping in, and Thursday when she picked me up from work (truck was in the shop) she was wearing my favorite t-shirt that I had to give up when I outgrew it at the age of 13.

I figured it was a "wife and mother" thing. Her husband and sons had clothing that fit her so she saved money by recycling them. Then I got to asking around. Single women, women with husbands whose clothing would either be tents on them or require extensive liposuction for them to fit into, and women with toddlers all freely admit to buying their clothing in the men's department of department stores. They say the pants fit better and a lot of the time they find a t-shirt design that's only available in men's styles so they buy them. These days there really is no men's clothing. There's women's and there's gender neutral.

As far as the cross dressing thing goes, my first girlfriend always wanted me to dress in drag. She said she thought it was cute when men dressed as women as long as they made an effort to look like women. She wanted me to wear nothing but women's clothing around my house when she was there, around her house, when we went on dates, and just running to the store for a jug of milk. I had enough of it so I finally came up with a way to get her to change her mind.

Now one thing you need to know about me is that I only get embarrassed around people I know. I won't even stick my head out the front door to check the temperature unless I'm fully dressed in case someone I know drives by, but I'll go streaking through New York City without a second thought. I arranged a little weekend getaway in northern Arkansas, told her she'd only need clothing for Saturday and Sunday, but to pack two outfits for each day along with an extra one, then when we got there Friday night I finally got her off my case. I put on one of her bras, decided to go all out and stuff the cups, put on her dress, and even though it was a little too big for me she started gushing over how cute it was on me. Then she did my makeup and we went out to dinner.

Like I said, I only get embarrassed around people I know so nothing bothered me that night. At first she thought it was cute, but by the time we got back to the motel she was utterly embarrassed because of the stares and comments we were getting. As soon as we stepped into the room she started wiping off my makeup, told me to take off her clothes, and handed me my night clothes (couldn't actually call them pajamas because they were just a t-shirt and cotton shorts). For the rest of the weekend I dressed normally, and for the three years we were together after that she never once mentioned cross dressing again.
 Ladyinred4755
Joined: 1/30/2012
Msg: 171
Have You or would You consider Dating a Crossdresser
Posted: 6/7/2015 3:45:04 PM
LOL, I never dated a cross dresser, but I had a good friend who was a cross dresser.
HE was slightly arrogant, self absorbed. We worked together but that was it.
SHE was not arrogant, and often thought of ways to make others happy. SHE and I talked, laughed, spent hours together on Lake Michigan, in her 40 ft yacht.
Then SHE moved away to start a new life.
 wooweewoo13
Joined: 7/7/2013
Msg: 172
Have You or would You consider Dating a Crossdresser
Posted: 6/10/2015 3:09:19 AM
well.....as Ive said many times to each their own and as some guys LOOK better than a female I like all the right parts when Im dating!....lol
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