Why Bisexual Women Should Consider Dating A Crossdresser

This is more of an opinion, rather than a story...but here goes

Women tend to think of crossdressing males in one of three ways:
1) Disgusted by the thought of a crossdressed male.
2) Indifferent to the thought of a crossdressed male.
3) Intrigued by the thought of a crossdressed male.

I suspect most women would fall into Category 1. This is understandable for sure. Afterall, humans are creatures of their environment. And society's general opinion is that men should dress like men, and not dress like women. This is a sort of social conditioning that begins at an early age and is rather well cemented by the time puberty arrives, and certainly by the time we reach adulthood. I have also read various polls asking women what they think of crossdressers, or if they would consider dating a crossdresser. The majority of responses are no's. You'll read comments like, "no" or "not if he looks better than me in a skirt" or "Hell no" or "not unless Hell freezes over." Anyhow, you get the idea.

A smaller percentage of women fall into Category 2. Those who are indifferent are probably a little more open minded than those in Category 1. They realize that there are a number of crossdressing males in society, and that fact does not particularly bother them. A lot of these women would probably accept a crossdressing male as a friend. However, they may or may accept a crossdressing male in a more initmate relationship. I don't believe a woman in this category would necessarily begin to date someone they knew to be a crossdresser...and that's not how most relationships between a woman and crossdressing male begin anyway. Usually, the dating begins with the male not exposing his crossdressing desires initially. As the dating matures into a loving relationship, the crossdressing male may then reveal his transvestic desires. BTW: some crossdressing males choose not to reveal this aspect of their personalities even after the relationship evolves into a loving one...but that's a whole 'nother can 'o worms. Regardless, once the CD reveals his secret, the woman has a decision to make. Stay with the guy or dump him. And, If she does chooses to stay together, she then needs to determine to what extent will she accept his crossdressing. Acceptance at this stage can take on wide range variations. Anything from, "you can dress occasionally, but I don't want to see it"...all the way to, "put on those stockings and heels baby, come and get me." She might also choose to accept him initially, only to change her mind later (yeah, sometimes this does happen).

Then there is Category 3. Every straight crossdresser on the planet dreams of meeting this woman, as she is a rare, but highly prized gem. She is turned on by the thought of her man transforming himself into a lovely woman. For the rare, wonderful woman that falls into Category 3, the world is your oyster. There are probably hundreds of crossdressing males for every female that is attracted to him. And I doubt that just any crossdressing male will do. Women attracted to a tranny are likely to want that tranny to look relatively convincing. She's probably less likely to want a big, burly, muscular, hairy, manly man - and more likely to want her man leaner, and hairless. Again, these are tendencies...nothing is totally set in stone. One thing is clear to me though...the women that fall into Category 3 can have their pick of the tranny litter, so to speak. This is where I think bisexual women have a distinct advantage.

Advantages for the Open Minded Woman:
If you think having a relationship with a crossdresser could be fun, then please read just a bit further.

Many years ago, I dated a lovely woman that described our relationship as "the best of both worlds" (it was not as cliche back in the '80s as it is today). She preferred men, but had bi tendencies and had experiemented with women. She enjoyed many aspects of our relationship. I liked taking her shopping for clothes and enjoyed watching "chick flicks" with her. It made us good friends. But the aspect of our relationship she seemed to enjoy most was sexual intimacy.

If I could generalize for a moment...crossdressers will do almost anything to fulfill your sexual desires and fantasies. My GF told me I was a much better sexual partner when I was dressed as a woman. Interestingly enough, others (both women and their CD lovers) here on EP have told me the same thing. This makes a lot of sense to me, because when I am crossdressed, I get much more into the act. Put me in a skirt, stockings and stiletto heels, and I'm more romantic, giver better massages, am better at oral sex, etc. etc. Crossdressers don't just want you to have an ******; we want you to have multiples on top of multiples until you are exhausted. Often times, we'll keep going until you beg us to stop.

In other words...ladies...whatever pleasures you seek, the crossdressed male wants to give you that in spades. I'm going to go out on a limb here, but I will bet that any tranny will do a much better job pleasuring you while he is crossdressed, than when in male mode only. Why is that? It's because the crossdresser is also getting exactly what he wants. The opportunity to please his woman, while being dressed like a woman. It's far less important for us to ****** (though we know we will eventually). It's far more important for us to ensure you are totally satisfied. And it's a turn on for us to help you achieve this state of arousal while we are all dressed up.

I have received testimonials from women to this effect. They love their hubbies, boyfriends, etc. But WOW...the sex is amazing when they are dressed up. Bisexual women and crossdressers can be a match made in heaven. Think about it!!

BizSuitStacy BizSuitStacy
56-60, T
12 Responses Feb 17, 2012

Than you for sharing this! My husband is a cross dresser among other things and we couldn't be happier! I loved him for who we was before I found out and love him more with each passing day. I love seeing him dressed up. It is a turn on to see him wear something sexy!

That's wonderful! Thank you very much for sharing with us. There are so many crossdressers out there, and it makes us so happy to hear from women who are in happy and fulfilling relationships with a CD!

Loved this story. Beautifully written and well thought out. Thank you for sharing it. I hope it reaches some Category 3 women out there!

I hope so too. Plus, I hope it opens the eyes and the minds of some Cat 2 women - and moves them toward the Cat 3 direction!

How should a crossdresser respond to a dating ad of a bisexual woman (or even a straight woman)? Any suggestions or examples would be helpful.

I guess it would depend on the ad, but I would try to be honest. Does the ad suggest that the woman might be interested in a crossdresser? If not, then chances are if you respond and mention that you crossdress, there is a strong likelihood of rejection. Remember, most women are not seeking a CD to date - even the category 2 women. She would need to be firmly planted as a category 3 woman to begin a relationship with someone knowing up front that they crossdress.

You have a wonderful way with words Stacy...you're awesome!

Thanks hun! Glad you enjoyed it.

I have gone public dressed up and most females I have met are in cat 3. maybe I do look convincing and had only fun with them.

You are convincing and quite the looker Robin! I'm not surprised you meet numerous cat 3 women. You totally own it, and women are attracted to you becaise of it. More of us gurls should be just like you!

I agree completely Stacy<br />
Hugs<br />

Thanks Sammi

just keep on sharing such observations... thanks


Wow ... you have comprehend the topic very well and covered each point perfectly..... I agree if women are lil bit open to cross dressing thing and let their men to wear their stockings , I am sure that would have a great experience which they have never had before......

I am a male cross dresser.I love your opinions about male cross dressers. I love to swim in a one piece bathing suit. I have found that women either accept it, are turned off, or maybe willing to be friends or more with me when they meet me wearing my suit. I would rather she knows up front that I swim in a one piece than shock her when we go swimming for the first time. I hope to find my match that accepts me and likes to swim in a one piece and fully clothed too!

Hi w1piece - you have the right approach regarding women and your CDing. I always believe it's better if they know up front. Some CDs have told me that they have gone out in public crossdressed. Of course, they get odd looks and perhaps off-comments or snickers...but once in a while...a woman recognizes courage when she sees it and is impressed. And these CDs would not have met the woman otherwise.

I have gone public dressed up and most females I have met are in cat 3. maybe I do look convincing and had only fun with them.

I really enjoyed reading . What You needed too say.<br />
I agree most of the above comments . Thank You <br />
For sharing Your insight . As I keep hunting for Miss type3<br />
myself .

She's out there.

Agree, Nice way of laying it out.

Thank you Indyrace!

Well written, and we'll thought out Stacy :-) I was kind of leaving towards that direction when my lovely wife fell in my lap. But i agree with you analysis, and i think my wife would too. She had no bi tenancies, but was open to my dressing though it happened in stages (baby steps). She realized she likes it, and it's fun for us. Nice write up<br />
<br />

Thanks Sensei! I know you have a great relationship with your lovely wife, and that the two of you can enjoy this wonderful aspect of your lives together!!