What Every Woman Should Know About Crossdressers

This is more of an opinion, rather than a story...but I hope many women and other trannies will read.

Women fall into one of 3 general categories with respect to crossdressing males:
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 the majority of women 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.

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 accept the fact that it's a relatively harmless hobby. These women would tend toward accepting 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 begin to date someone they know 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. Once revealed, the woman has decisions to make. Stay with the guy or dump him. If she chooses to stay, then 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."

Then there is Category 3. Every straight crossdresser on the planet dreams of meeting this woman, yet she is very rare. 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.

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

The crossdressed male will do almost anything to fulfill your sexual desires and fantasies. For example, I enjoy giving oral to a woman. However, when I am crossdressed, I totally get so much more into it. I don't just want you to have an ******, I want you to have multiples on top of multiples until you are exhausted. I won't be happy until my face is completely covered and soaked from your pleasure. If you like toys...just tell me how you'd like me to please you with them. Maybe you'd enjoy a nice deep massage...I give wonderful massages, but they are so much better when I'm in stockings and stiletto heels.

In other words...ladies...whatever pleasures you seek, the crossdressed male is willing 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 have many, many *******. And it's a turn on for us to help you achieve this state of arousal while we are all dressed up.

There have been a few women who have given testimonials to this effect. They love their hubbies, boyfriends, etc. But WOW...the sex is amazing when they are dressed up. Think about it!!

BizSuitStacy BizSuitStacy
56-60, T
26 Responses Oct 20, 2011

Thank you for this information, it's great to hear the opinions of crossdressers.
I'm a woman, and have identified as a lesbian as most of my life. Recently I had the opportunity to play with a crossdresser (a male, in female mode), and to my surprise I loved the experience. I would like to know more before I continue on this journey, as the last thing I want to do is inadvertently insult anyone. If anyone can answer these questions for me, that would be wonderful. I understand that everyone is different, and everyone's desires are different, but am looking for as much info as possible.
Do crossdressing women want to have actual sex with biological women?
Are crossdressing women open to biological women playing with their penises when dressed as a woman?

As for me I prefer to leave the direct sexual implication out of everything. Instead it turns me on if the mind of a gg-friend circles around something like: 'she is so sweet, she looks really like a girl, I cannot believe it, what happened to her that she is like this, she could be my sister, I want to see / know more about her, make her more as a girl, see how she acts in public, how other people react, if she wants to be a girl I treat her like this, other people should know that she only looks like a girl but she's not, I made her like that, I control her, we are staying together as girlfriends, I'm turned on by it...

according to my experiences I can contribute a more specific categorization of women/girls who specifically like tgirls/crossdressers and unfortunately I have to pour some “water in the wine”

1.group (70 %): girls who are unattractive, fat, very small or have problems with their femaleness. Their intention (besides of not finding a normal boyfriend) is to have somebody who they can compare with or who can teach them some feminine behaviour. These girls are usually ready for a deeper relationship.

2.group (20 %): girls who are confused /weird / 'freaky' -they want a relation to somebody different and exotic who they can show off with. Their interest is curiosity - to see what happens, how far they can go - the fact that I am a tgirl in the end is not so important.

3.group (10 %): women with a clear sexual intention, they want to try out everything which can be quite disgusting. Quite often they say that they are attracted in the combination of male-tension and female tenderness - something like 'best of both worlds' what for them is always sexual related.

A kind of misunderstanding is the idea that true lesbians are interested in tgirls – the mind-sets are too different.

If you are interested in a normal, kind of sisterly girl-girl-friendship I have good experiences to get in contact to normal girls during shopping, in sidewalk cafes or other normal “straight” places. Usually the response is friendly. In my YouTube channel “crossdressed among women” you find some examples of what you can do.

Very interesting take. Thanks for your comment!

I have identified as a lesbian for most of my life, but have recently discovered that I'm attracted to crossdressers and transwomen. So it is possible.

it would be interesting to hear what exactly attracts you in tgirls - what is on your mind - what thrills you

Great story - it only makes me want to meet a real Tgirl all that much more. I'd love to have a romantic night with a Tgirl and make her feel all woman - now that's exciting !

T-girls can be incredibly sexy!

I don't know about the ladies who like cross dressing men but I have had a thing for CDs since I had an experience with one when I was in my early 20s. I am the big burly guy you mentioned that would never pass for the fairer gender and I met a petite CD in Arizona during my travels and had a short but very fun relationship with her. I would look forward to doing that again someday.

That's cool. Thanks for your comment.

I am number 3. Feeling sexy with my sissy husband, having a lot of sex, feeling I am a lesbian, a woman and also his man.

Awesome! Thanks for sharing.

This is an interesting way to look at it. It makes sense to me. Although I do think some fall in between the categories. My wife started as a 1, and fortunately has slowly evolved into a 2. Or maybe a 1.5. Who knows what the future may hold!

Yeah, this is a generalization. Some women do sort of fall in between, and have even messaged me as such saying they think they are a 2.5. LOL! It goes to show that people do change their opinions on things, but the change around a topic like this may happen gradually over time.

I'm 22 my man us 23 and just recently told me he likes to cd I was shocked at first but I love him so much I decided to be supportive and now I enjoy it I get to show off my dominant side as usualy im the sub its like role reversal for us and has made our realationship stronger so I guess im a 3 :)

Thank you for commenting! You are very much like the women I've told of my crossdressing. At first, there is surprise or shock - which is a very normal reaction. Most crossdressers give no clues about their inclinations. And, very much like the women I've told, they take a step back, realize they love this person, and then accept the fact that he is a crossdresser.

It is at this point where a woman learns whether or not she likes this side of her man. I am glad to hear that you enjoy it!

Amen Gurl. I was honest w/ my girlfriend 7 months ago and she is darn sure enjoying me doin what I LIKE :) She is a rare woman and I treasure her for her acceptance. I need to lose some weight to be "Slim" but I am having the best XXX of my life at age 59 and she said that I am the best lover she has ever had (and she never lies :) Sincerely, when you think you are at the end, and you take a chance you would not have previously, and you start a new phase of your life... WOW. Stay tuned.

That is fantastic! I am so happy you found your precious gem! And yes, would love to hear how things continue to progress.

I have a theory, and while I cannot prove it (yet anyway) I do think if the public gains wider exposure to couples who crossdress

at some point, the idea of a man crossdressing may not seem so weird. And just maybe, women may not look at it with the standard pre-conceived notion that it's too weird to consider.

I feel like I'm coming out as a 3. As a teen I was pretty sure I wasn't a lesbian, but I always ended up being more attracted to gay men or masculine women. Recently I realized I'm not really attracted to gay men but to feminine men. I feel so relieved now that I can put a finger on what I'm attracted to. I live in a rural area where all the men try to be "manly" all the time, and it just turns me off. I think most guys I know would think I'm really weird for this. I'm not sure if this is the place to ask, but how can I find a guy who does this?

I think this is as good a place to ask as any. There are lots of websites online where you could put in an ad and ask for pics/information - and try to meet someone that way. In a lot of larger cities, there are TG friendly bars, and even CD support groups. Heck, there are lots of CDs here on EP - maybe some in your area, you may be able to get to know.

Always remember, for every Category 3 woman out there, I'm guessing there are at least 100 crossdressers dying to meet you.

Crossdressers.com and social sites like meetup.com search crossdresser or even just cross (in case they use a space?) Also there are usually local clubs that support "trans-gendered" males like Tri-ess. But be aware and learn the differences between Pre op, post op... MALES MUCH MORE SERIOUS ABOUT SEX CHANGES VS. CLOSET DRESSERS and CD's come in many flavors and degree's of "drive"... from casual/ occasional dresser (probably your fav to begin getting involved with) to TS that call themselves CD but are really wanting to be women more than just dress up. Some CD's want to dress like granny in bloomers and have no sex drive associated w/ it and some want to be submissive ***** and it is all about sex (me). Another important distinction is whether they are hetero, bi or gay. And no matter what, like if they are hetero w/ Bi curiosity... the most important thing: will they be monogamous. This can include the occasional poly event AS LONG AS IT IS WITH PARTNERS APPROVAL AND KNOWLEDGE.

I like being a man but love the idea of being in women's clothes and like to shave but my wife isn't into it sadly.

Well written and thought out
Ive been married to a wonderful women for 25 years unfort shes a big ole # 1 ( well shes a 10 to me) lol
Anyway ive been dressing up since i was knee high to a grass hopper
Being married never stopped me my wife knows however dont ask dont tell seems to work for us
I often wonder what life would be like to be married to a #3 how could you not so to all you " girls" out there who are lucky enough to be with a #3 congrats
However with respect and love ( and some really good friends) you can still enjoy and explore your feminine side even if your wife doesnt approve
Enjoy life

Being with a #1 is not easy, but as you said, "Don't ask, don't tell" can work. Congrats to you for keeping things in full and complete perspective!!

I wish I knew how to do this.

My friend I would love to chat w you and try and answer any ? U may have
I'm running to a Xmas party so it's gonna be a little choppy tonite but keep after me
Enjoy life

Tammi, thank you for your reply. I would like to talk to chat with you sometime too.

1 More Response

I'm between 2 and 3. My BF does not crossdress but he is very attracted to trannys. We both would want the most 'convincing' one we can find and they seem quite rare. We're looking for a friend and ********* play partner. We've only tried with a not so convincing CD and just want a little more. Are there any convincing trannys in NY??

Finding someone convincing is definitely possible. Transsexuals tend to be a bit more convincing than crossdressers due to hormones used which help enhance the feminine characteristics. Unfortunately, the hormones can also shrink the testies and prevent the penis from getting hard. These are not absolutes, just tendencies. Many of the pics you see on the internet of convincing trannies are simply good photoshop jobs. But - I would think that in order to find someone like that - NY would be among the best places to look. Good luck!

You must have passed loads of them on the streets but they are just so convincing that you just didn't realise it lol.

Here's hoping that you find what you're looking for.
Have a lot of fun.


Of coarse your totally right hun, however girls 4 fem guys are not as rare as you have experienced.
I also can verify from several women that xdressed men make better lovers. My gf doesnt want me in guys clothes at all, and i always agree with her lol.

Good for your GF and of course you as well, Gracie, not wanting you in guy clothes! Sounds like my wife starting back on our second date and she found out I dressed and enjoyed it. After that she not only encouraged me, but insisted I xdress ...

Yep, I wouldn't argue with her either! LOL

Fortunately I am married to a gal who falls into Category 3 and it is great. At first it was crossdressing ... not only did she want me to dress for her, but it both pleased and excited her when I did and she started encouraging me to dress more and more and underdress full time. With each step I have taken, she is excited but always she wants me to go further. We share the feminine together and it is great! But I think it would scare the you know what out of many crossdressers to have a wife like mine.

That is so wonderful that your wife takes such an interest in you dressing for her! More CDs should be so fortunate! Thanks for sharing.

Thanks Stacy and yes I certainly agree!

Well the easiest way to find out, kkane4u, is to read some of what I written and posted here and you'll find out what I mean by saying taking my dressing further.

I love my lover to be manly and hairy and all that is masculine but I have to admit I am very intrigued by crossdressing men ;-) I think you guys rock!!!

I find your intrigue, intriguing! LOL. Thanks for your comment. Perhaps sometime you'll take a walk on the wild side and experience a lover who is more feminine and hairless :-)

Pixelita (interesting name by the way)

If you are in a stable relationship then I would encourage both you and your partner to be true and faithful to each other. If however you are free and single then a walk on the wild side might be an amazing adventure for you ;-)

We were the same way until begining to explore shaving. The smooth body became a way of living and now we would not go back.

Thanks for the encouragement. We love to hear those words!

I have a female friend -- she used to be my boss. We got along well at work and we continue to see one another for lunch every now and them. I'm married and my female friend is just that and more valuable to me as a friend.

If anyone has followed my posts -- I like to cross-dress and have done so since I was 12 when I started to "borrrow" my mom's stockings and garter-belt. Therre's no way I could ever 'pass' however.

One topic at lunch with my friend was her getting a tattoo -- finally after her talking about for the longest time. We talked about how some things become socialy acceptable.

As an example, I told her how it was strange that it was acceptable for me to color my skin with a tattoo -- but not to color my fingernails with polish.

She laughed and said -- in a low voice-- that she once had a boy friend who shaved his legs and painted his toe nails. Then, she got a funny smirk on her face and said, "It sure worked for me."

Yikes! -- I thought. I better change the direction of this conversation really quickly!

But, that told me a lot about her. Perhaps too much. Category three. But I'm married.

That's awesome! She does sound like a category 3. I have a friend who is a category 2, with whom I confessed to as being a crossdresser. She was cool with it. We are good friends and occasionally go out to dinner or have a drink together. One night, we went out, and I brought along a few pairs of my high heels. She got a big kick out of them, and even tried them on. Another time, after I shaved my legs, I wore pantyhose under my jeans along with a pair of black pumps. She thought it was great. She even had me get out of the car for her, and walk around the parking lot in my heels. She laughed and said, "you look like you've been walking in heels for years." And...well...I had. The point is - we are friends, and I can let a little bit of Stacy come out around her, and I treasure our friendship even more because of it. I would never try anything with her as it would not be fair to my wife. So, I think you can be honest with even a Cat 3 woman and still keep things on a friends level.

Hi sweety, I'm one of those rare women you wrote about in catagory 3. For years because of abusive men in my past, I turned to other women with whom I felt understood my needs. Until meeting and eventually marrying "Leah" a male crossdresser with a huge woman's heart, lol! "She" is more than willingly to do my bidding, and is thoroughly contented with me in total control of our intimacies. My physical fulfillment could not feel more pleased than at the moment of this writing!!

Oh that is wonderful, and thank you for your comment. I absolutely love hearing from women who say they have a happily fulfilling relationship with a crossdresser. We make great husbands and wives all at the same time!! Bless you and Leah! I wish you many years of wedded bliss together!

Thank You Stacy you truly are a sweethart! Leah has often commented on his two divorces being due to her crossdressings. I do not understand these things, my own gender? But then again I have always been regarded as how you say "wicked witch from west" by my female contemporaries. I do not care! If being a slave to men makes them then so be it, lol!

Your views represent many of us,I being one for sure.If I had a woman that would accept me totally I would do anything for her.<br />
Louise CD

Hi Louise - Indeed!! Women that find gurls like us attractive or even hot are worth their weight in gold. Put them on a pedastal and treat them as the goddesses they are. I honestly believe some women don't realize just how good they would have it, otherwise they'd be signing up and standing in lines. LOL

Thanks for the kind words girl.
Girls like us need female companionship real bad.
We suck men but prefer women all the time.

Very Well Said Stacy, Thank You from all of us wanabe girls


how come it's okay for a woman to dress in a suit and tie that she got in the ladies department, but it's wrong for us men? you've claimed our wardrobe soon a man in a suit will be crossdressing!

I know. When I was in high school, I took a girl to one of the formal dances. As typical of the day, I wore a tux, she wore long gown. The day after the dance, she asked if she could try on my tux. Of course, I said, sure and even took a couple of photos. Of course, there was no way I was going to ask her if I could wear her dress (although I would have really liked to try it).

Point being, society has dictated a man must look and dress like a man (as per what is defined as a manly look for that day and age). A woman, on the other hand, can dress in just about anything she wants. if she wears clothing that is typically considered "male" it's fine...perhaps even quite fashionable. It's screwy, but that's just the way it is.

This might initially seem like an absurd comment but the skirt was once an item of male clothing and wearing that item of clothing is now dominated by women to the extent that a man wearing a skirt is seen to be creepy and deviant to large sections of western society.

Not absurd at all. History gives us a very clear indication that fashionable men's clothing 200+ years ago was rather feminine looking. Affluent men in particular wore gowns or dresses, skirts, hosiery that looks much like stockings, high heels, wigs, makeup and even perfume. Of course, today, that's no longer considered high fashion, just weird.

Personally it intrigues me, but I would probably put myself as a 2/3 if actually confronted with my H saying he was a CD. The prospect of fulfilling sex is very attractive!

Hello Anothertime, and thank you for your comment. It is wonderful to hear from a woman who is open minded and intrigued by the thought. Yes, the sexual aspect can be amazing. One possible thought...try asking hubby to wear a pair of your panties during romance. Many women are surprised by the response and are treated to a wonderful session of intimacy!

I would so love to show you how much a CD like myself would make love to you darling.
Louise CD

My wife loves the attention she gets when I'm dressed up.<br />
She knows she's in for a great night of fullfilling sex!!

Hi Allwrappedupinit, and thank you for your comment!! I am so pleased to hear from other CDs who have wives that love it when they crossdress. It is a wonderfully common theme I hear again and again...the sex is incredible!

Very good post. I am blessed to have a category 3 wife. Thoght she does go for the slutty look. Not for her but for me LOL<br />
<br />
Who am I to complain

That's wonderful! Since posting this "story" I have heard from many CDs with wives or GFs that fall into category 3. Yes ladies...many of you really do enjoy a little crossdressing. Thanks for sharing!!

Great post Stacy, <br />
<br />
I have always told any woman I have ever dated and the one I married that I was a crossdresser and that I had bi-sex. I either told them immediately or within a few days and up to maybe 30 days into it. I have never lost a woman because of being a crossdresser and because I told them all upfront about it. The responses varied as some women were ok with it and didnt want to really see it or participate in it and to the other end of the spectrum, some were intrigued by it and loved every minute of every time she could be with me en femme. Those that were "category 3's" were so supportive and participated in helping with makeup, buying feminine gifts, clothes, makeovers, mani-pedi's, etc... <br />
<br />
I'm also bisexual with a male preference and I have a loving gg gf of 2+ years now who knows all about my sexuality and my femme side. I have not been with a man or have had any bi encounters although she says she is ok with it if I do. She doesnt want to see it or participate at this point if I were to be with a man or preferably, another effeminite male to female cd. <br />
<br />
I feel so fortunate, so lucky, so blessed, or however else I can describe it. It has all been ba<x>sed on total honesty, trust, and communication. <br />
<br />
She has attended annual transgender conference events with me and she encourages other girlfriends and wives of crossdressers to indulge and enjoy the benefits of a transgendered man or having a crossdresser for a boyfriend or husband. Research has shown that there are namy positive benefits in a relationship or marriage where there is a crossdressing husband or boyfriend. Your post was well written and addressed the key issues and concerns. I only know this from experience with my situation and it works for me and my category 3 :) <br />
<br />
~hugs~<br />
Marlene <br />
Honestly Speaking :)

oh,, I forgot to mention that I got divorced from my wife before meeting my lovely gg gf and that my divorce had nothing whatsoever to do with my crossdressing.. :)

Thank you for you comments Marlene. There are indeed many benefits a couple can share where the hubby or BF crossdresses. I personally enjoy shopping for clothes for my wife. I know her sizes, her tastes, what looks good on her, etc. Sometimes her friends will compliment her on something she is wearing, and will ask where she got it. Her friends would be so surprised when she would tell them that I purchased it for her.

Divorce is sad, but sometimes it is for the best. It does sound like things have worked out well for you snce, and it's great to hear that you are happy.

I understand.. I get a kick when my gf wears something of mine to her work where she supervises about 85 people and all the girls compliment her on what she is wearing and only she knows its my outfit and attire .. :)

1 More Response

Wow, how neat to find out that my wife is category 3 ... but I already knew that. She 'discovered' that I crossdressed on occassions, which intrigued her, and she wanted to know if I enjoyed it. When I admitted I did this excited her and she insisted, wanting to see me. The next date she did and ever since then she has been both supportive and encouraging, wanting to help and explore my femme side. It is awesome!

Thanks for you comment TGhubby! Yes, there are category 3 women out there. And what's wrong with enjoying a little clothed kink? Absolutely nothing! So gald you two can enjoy it together! I hope more women read the comments everyone has shared with this story. Open minds and horizons!

You're welcome and I agree BizSuitStacy.

I was involved with a man that after we fell in love that he was a crossdresser, but later on found out he wanted to be with a man and wanted to be all women, and he wanted me to tell him what it feels like to be with one, so I ask, where does it leave the women? If this man wants to be with a man, will he ever accept a women? And he is married...how would his wife feel if he asked her if he can have a mans private part in his mouth or any where else for that matter...How do I handle this? I still care for him, and we have broken up more than once and got back together recently, but don't know how to handle it..

I feel for you in your situation. I am a hetero fetish cross dresser. My wife's only question when she found out over 33 yrs ago was "Are you gay or something?. I shook my head No. She was cool. I wish that I could help you in some way.

Hi Excited - I know this may sound like double talk, but it sounds as though this man with whom you are involved with may be a transsexual, instead of a crossdresser. I'm not positive about this, BUT - I do think it's important for you to find out for sure. There are very significant differences between CDs and Transsexuals. It goes well beyond the clothes you choose to wear.

I think it is fair of you to ask him about his sexual identity. Does he really want to become a woman? OR Does he just like fantasizing about it? I would venture a guess that all CDs fantasize about being a woman. I've had this fantasy myself, but it's only a fantasy. I realize that I like being male, and want to keep my male parts. Transsexuals typically take hormones, go though therapy, and transition to living as a female full time. Some will even have SRS (sexual reassignment surgery).

If it turns out he is transsexual, he may prefer men as he identifies himself internally as female. He may still choose a female partner, but that has more to do with social acceptability.

If he's not a transsexual, and instead is a crossdresser, then it's important to address his sexual orientation.

I know that some CDs do have a "bi" side to them that only surfaces while they are crossdressed. Normally, this type of CD is not interested in men, unless they dressed up. But when they are dressed, the bi side surfaces, and they are likely to take a man orally and/or anally.

I honestly believe that this "bi" tendency is the result of years of sexual frustration. CDs are notorious for finding themselves sexually frustrated. Trannies want to have sex with a woman, while dress like a woman. Unfortunately, very few women are interested in having sex with a tranny. Therefore, IMHO, some trannies do begin entertainiing the idea of being with a man. And there are lots of men that think transvestites are hot. If a tranny wants to have sex, it's much easier to find a willing male partner than it is to find a willing female partner.

I am going to send you a private message to finish my thoughts.


I was cool with the dressing up part and so is his wife, but when it came to being with a man and wanting to be all women, then that kind of got me thinking, all what we had is gone and it breaks my heart, because I don't think I can be with a man, even if we do someday, that wants another man instead of me...

Exactly! I am hearing this more and more from people. Women who are open to the idea of having sex with a crossdresser says the same thing...the sex is great! <br />
<br />
Try it ladies...you will love it.