A
male
age
36-40,
anonymous
writes:This question is for the girls. How do you feel about a guy who likes to crossdress. Would you date a crossdresser? Would you be involved helping him achieve a feminine lifestyle and look? Reply to this Question
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Fancy yourself as an agony aunt? Add your answer to this question! A
female
reader, moon river  +, writes (18 April 2011):
 Yes! I find it strangely attractive
A
female
reader, So_Very_Confused +, writes (15 April 2011):
 I would. Sure not a problem for me.
every cross dresser I've ever known has been exceptionally masculine when not dressing... and all the cross dressers I have known are hetrosexual.
now most DRAG QUEENS are gay that i know of.... but that's all just my personal observation.
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A
reader, anonymous, writes (14 April 2011): Thanks for your patience and thanks for sharing OP, Miamine, and especially Lovebird1....from the way you described it, it sounds like male crossdressers find female gender roles more sensual and subtle then male roles and they get a particular kick out indulging it. Am I wrong to think that most movies portray male cross dressers as gay? I feel like this is where I got that impression.
I would agree, women are more sensual aesthetically...I'll enjoy watching woman-woman porn for instance because I think it's often more attractive than male-woman porn. But I also like things about men. They tend to be stronger than us, their bodies are harder than ours, more squarish than us....AND I especially appreciate the fact that they tend to be far less self conscious about their appearance then woman.
When I've been to clubs where there are crossdressers and they've approached me, I think I've literally mistook their come-ons as just being friendly. For instance, the last one I met said at a club, a gorgeous crossdresser danced with me for a while and then said, "Ooooo...I like you!" and then kissed me on the cheek, debutante style. Now, I just assumed this whole exchange was part of her persona ... this was sort of girl she identified as. Friendly, a bit sultry...and a bit of a debutante. I didn't think it really had anything to do with me personally. I would have liked just to think she admired my dancing.
Had she said, "let's be friends" and I enjoyed her company, I would absolutely help her with her look. I guess I would have trouble being aroused by it simultaneously.
Maybe I just haven't lived enough. Thanks for explaining.
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A
female
reader, Miamine +, writes (14 April 2011):
 Mishmash, crossdressers are straight, they like women.Sigh.. just thought about it some more. Crossdressers are often very "strong men". In the UK we have a very famous topless model, Jordan. Her last husband was a crossdresser and also a cage fighter. Nobody cared, and nobody thought he was gay. Some people thought he was badly dressed though.Yep, with all them muscles and a little skirt and lipstick, he looked tougher than ever.Maybe I'm wrong.. a strong cage fighting crossdesser might be more interesting than I first thought... lolMany men who wear women's clothes are very controlled and masculine in everyday life and just like some extra softness when they come home. Not sure what happens if they like to dress feminine outside on the street.
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A
male
reader, anonymous, writes (14 April 2011): To mishmash. Most crossdressers are straight. I am bi though. I've dated girls but I never brought up the crossdressing conversation with them. I guess I sensed that it would not be a good idea. I have also dated several men and was always dressed as a woman for them.To lovebird1. Your statement is 100 percent correct. I only wish I could share this with a woman. The tender moments you described could not happen or would not be as intense with a man.
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A
female
reader, lovebird1  +, writes (14 April 2011):
Dear mishmash,
I wanted to say something about the "grooming" part.
I already helped a crossdresser to dress up and I liked it. I really liked putting on the makeup, watch him wear different outfits and tell him what would suit him etc. I don't know why but it really turned me on to see this transformation .. well, as I said, I'm bisexual and I've probably got a different perception of what is erotic.
I agree that most of my purely straight friends would probably find it irritating to have a crossdressing boyfriend, because they are only looking for masculinity and feminity signalises something nonsexual or concurrence to them.
But this whole styling part can be so hot, because you can help someone transform into another role, and you can maybe even take control in this transformation. There's the intimacy of sharing a secret, and the appreciation of your make up skills. The closeness of your bodies. So many ways to touch him gently, adjusting a dress, running your hands over his stockings, putting on the eyeshadow while he closes his eyes.Suddenly having this cute girl in front of you that you are totally going to ..uhm.. have a good time with ;)
I can't explain this to a woman who doesn't find crossdressing sexy; but it instantly turns me on and I can't help it.
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A
reader, anonymous, writes (14 April 2011): Can I ask you a question?
It's probably an ignorant question, but do crossdressers, (men who take on a female gender role) like women?
I've been wondering about this for a while. I have always assumed they like men...I've been hit on by crossdressers, but I though they were just being nice...or overly friendly. Lately it occurred to me, that there might be more to it...Do crossdressers typically go for women or men?
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A
reader, anonymous, writes (14 April 2011): Frankly, no.
When most women help each other dress or otherwise "groom" each other, we tend to assume it's an activity gearing towards attracting sexual attention of a third party - specifically not the sexual attention of our female friend. It's purely nonsexual bonding. That's the beauty of "grooming" between females. It creates a non-competitive atmosphere where we actually help each other succeed towards a goal.
Women can be quite competitive with each other and I (and I think most women think) grooming each other is one of the few activities where we can genuinely help each other out in a noncompetitive way. For instance, we may say, "yes...that outfit makes you look easy" or "no... that outfit will not get you laid"....that's the idea of it. It's pure, nonsexual bonding and it requires a third hypothetical audience. I'm not saying this is the only purpose of "grooming" but it's what most women have been conditioned to expect out of the activity.
The problem with dating someone and doing this activity with them simultaneously is it would completely confuse the ultimate purpose of the "grooming" activity. For most women, the confusion would come from the fact that you are both the "friend" and the "third party audience" at once.
Women do dress up to impress each other...but this tends to be competitive, not bonding...we want to look better than other women.
Perhaps I'm not imaginative, but I think the irony of dressing up your lover for an audience is a bit too much and provokes too much jealousy.
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A
female
reader, Miamine +, writes (14 April 2011):
mmmm.. Not too keen on it myself, I like strong men.. However, if I love a guy and that's what he needs, it's a small thing to keep him happy.
Relationships should be based on love and compromise. A happy man will make a woman smile, and if he's wearing lipstick, then it's just another thing to get used to.
Find the right woman, and she'll love you too much to care about your little kink.
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A
male
reader, anonymous, writes (14 April 2011): Thank you lovebird1 for your supportive comment. Your advice is greatly appreciated. Too bad I do not live in Germany :)
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A
female
reader, lovebird1 +, writes (13 April 2011):
I LOOOOVE cross dressers!!!Really, I do! I mean, it depends of course, they need to have a good personality as well etc. but I do share this.. I don't know.. fetish (?? sorry if this sounds negative, it's not intended). I'd definitely involve in styling him etc.I think my acceptance/love for cross dressers stems from my bisexuality. I've spoken to another bisexual girl and she also likes cross dressers.Well, what I want to tell you, maybe you're not mainstream, and maybe not all girls will like you or accept you. But- and here's the big but - there are girls out there that will adore you (well, if you're a nice person on top of this). I'd suggest you look for a girlfriend on the internet. I don't know where, maybe alt.com? An alternative would also be to mingle with queer or fetish people, go to queer parties, fetish parties, or goth parties. People are more tolerant of your lifestyle there. It will take you less courage to come out to these people than to a random straight girl. But I am guess there are exceptions as well who'll accept you.Big hug and good luck :)
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A
female
reader, Elydiese +, writes (13 April 2011):
No way sorry
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A
reader, anonymous, writes (13 April 2011): no
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A
female
reader, tennisstar88 +, writes (13 April 2011):
 I don't like lending my wardrobe out to my friends who don't bother giving it back, much less washing it. Definitely don't want to share my closet with a cross dressing boyfriend either.
So that's a big fat NO!
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A
female
reader, anonymous, writes (13 April 2011): Hell to the no. I like men. A strong man that thinks my grily stuff is stupid. That's sexy. There is only room for one girl in a relationship.
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A
female
reader, DanceInTheDark  +, writes (13 April 2011):
 Well personally, I have no problem with cross dressers. But I couldn't date one, it's a deal breaker for me.
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