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Show ALL Forums  > Dating and Love Advice  > Crossdressing; tell up front, or wait? Another bad experience.      Home login  
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 carolann0308
Joined: 12/9/2006
Msg: 26
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Crossdressing; tell up front, or wait? Another bad experience.Page 2 of 8    (1, 2, 3, 4, 5, 6, 7, 8)
I would have it in your profile and be upfront about it from the first email. It's no different than discovering your date is a smoker after the first meeting and you don't care for that. Cross dressing is not easy for many women to handle.
I do have to agree with the above poster who mentioned your childhood should not be 'date' conversation, get yourself some therapy to deal with it, the woman sitting across from you is there for dinner not to be your analyst.
 vivaciousvixen2
Joined: 3/1/2008
Msg: 27
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/7/2008 6:27:36 AM
Like anything, people are judgmental. I am friends with a man who is a crossdresser. Don't tell anybody until you choose to trust them. Do not date them. Get to know them as people slowly. Put on your brakes brother. You don't need your heart broken by a jugemental person or a person calling you a gay. Take it really slow.
 dysfunction_junction
Joined: 7/17/2008
Msg: 28
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/7/2008 7:35:10 AM
quirkyenglish, you're awesome!
i *love* the pictures and the profile is great. i can't see that you should have anything to be shy about. i would be honored any day to meet somebody such as yourself.
ack, narrow little minds are so incredibly dull.
 Gwendolyn2010
Joined: 1/22/2006
Msg: 29
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/7/2008 7:46:10 AM

Again the assumptions that I might be gay, and I 'should explore that side of my life more' and all the thoughts that prelude the eventual 'I don't think we're right for each other' speech.


This woman might have assumed that you are gay, but that would not be the assumption of every woman who finds crossdressing unappealing. I understand that "gay" and "crossdresser" and not synonymous, but I would not get involved with a man who wants to wear women's clothes--it is, simply, not appealing to me (even if I never saw him in those clothes).

This isn't a moral judgment because I simply don't care what people do in such arenas. I have a very good male friend who is into BDSM--that doesn't appeal to me either, and though we are friends, we would never be intimate for that reason alone. I don't find men who who wear fanny packs or crocs appealing, either (both recent POF forum topics). Shallow? Who cares? It's my decision.

You should tell women ASAP--why let a relationship begin only to be shot down later?



I'm not sure I can go on like this any more.


I do sympathize with you, but go on in which way?


ack, narrow little minds are so incredibly dull.


Not wanting to date a crossdresser isn't necessarily the result of having a "narrow mind." We all have our likes and dislikes--it is a narrow mind that judges others based on their personal preferences. Some women like obese men--I don't, does that make my mind "narrow"? We have certain stimuli that turn us off and turn us on; crossdressing fulfills a need for the OP. People who find it unappealing need their "fulfillment," as well; if they can't find it with a crossdresser, why should they be judged any differently than he?

QuirkyEnglish--for sure, I wouldn't date a man who looks better than I do in women's clothes!

 dysfunction_junction
Joined: 7/17/2008
Msg: 30
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/7/2008 8:07:40 AM
Not wanting to date a crossdresser isn't necessarily the result of having a "narrow mind." We all have our likes and dislikes--it is a narrow mind that judges others based on their personal preferences. Some women like obese men--I don't, does that make my mind "narrow"?

(1) i never said that it was.
(2) of course not.
my reference to "narrow minds" was made specifically towards people who would reject a cross-dresser based solely on the fact that he is a cross-dresser. in other words, if you met this person and got to know him and you love everything else about the man, but discovering that he's a cross-dresser sends you right over the edge, then yes... that *is* narrow-minded. in my opinion.
but being narrow-minded is just another personal choice that's available to anyone, isn't it.
 LaMediaNaranja
Joined: 7/23/2008
Msg: 31
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/7/2008 8:42:37 AM
OP: Hmmmm........Ok, what exactly do you do with this "cross-dressing" fixation? Do you just dress up in women's lingerie/clothing at home and just "parade" around the house? For yourself (no audience)? I'm in no way trying to disrespect you or your likes. Just trying to better understand this whole male thing with cross-dressing.

I'm pretty open-minded about most things - as long as you aren't harming anyone or doing anything illegal. However, I would have a problem with a potential S.O. dressing up in my clothes!!!

Most hetero women want a manly-man and won't be too keen on their man dressing up in women's clothing. So you may have a hard time finding one that will accept this. UNLESS, you become part of one of these alternative lifestyle circles.

Best,

 Gwendolyn2010
Joined: 1/22/2006
Msg: 32
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/7/2008 8:43:03 AM

my reference to "narrow minds" was made specifically towards people who would reject a cross-dresser based solely on the fact that he is a cross-dresser. in other words, if you met this person and got to know him and you love everything else about the man, but discovering that he's a cross-dresser sends you right over the edge, then yes... that *is* narrow-minded. in my opinion.
but being narrow-minded is just another personal choice that's available to anyone, isn't it.


If I got to know a man who was a crossdresser and several months into the relationship he told me, then he is a liar--and it wouldn't have slipped his mind: it would be a lie by omission.

I don't associate with liars either in friendships or love relationships.

I would date a bisexual man, as long as he doesn't wear my undies.

If I wanted someone in pink lace, I would date a woman, and if I were bi, I would not be attracted to a mannish woman.
 dysfunction_junction
Joined: 7/17/2008
Msg: 33
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/7/2008 9:37:55 AM

If I got to know a man who was a crossdresser and several months into the relationship he told me, then he is a liar--and it wouldn't have slipped his mind: it would be a lie by omission.

that is because cross-dressing is obviously some kind of a really big deal to you. and by big deal, i mean in a negative way. again, that's your perogative.

i guess maybe you send out a 10-page list of interrogatories right up front, but most people are several months into a relationship and still be finding out all kinds of things about the other person. some of them might be of a highly personal or more sensitive nature, and maybe it takes several months for the person to feel comfortable enough with you to talk about them. that doesn't make it a "lie by omission" by any meams.

i would not kick somebody to the curb just because they indulge in something harmless that i might personally not want to engage in.

but that's just me.
 quirkyenglish68
Joined: 2/13/2008
Msg: 34
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/7/2008 9:39:32 AM

QuirkyEnglish--for sure, I wouldn't date a man who looks better than I do in women's clothes!


Ack! I can't seriously believe this is an issue that women will have regarding crossdressers.

I've been out dressed as a girl on dates with a girl, I may have been thinner than her, but she was certainly far more prettier than me, and when we were at the club together - despite my having my arms around her or having her on my lap (and we were snogging most of the night) - the guys would come up to her and chat her up (completely ignoring me of course).

BTW I actually really want to date as a regular guy, do the regular guy / girl date things, I never really expect my date to be involved with my dressing - hmmm maybe I need to add that to my profile - in fact she may never need to she me dressed, though I hope she would.

OP - sorry I feel like I've hijacked your thread.
 Gwendolyn2010
Joined: 1/22/2006
Msg: 35
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/7/2008 11:31:41 AM

Ack! I can't seriously believe this is an issue that women will have regarding crossdressers.


I can't seriously believe that you took my comment seriously.


that is because cross-dressing is obviously some kind of a really big deal to you. and by big deal, i mean in a negative wayl


Obviously, it is a big deal, period; if it were not, the OP wouldn't have started this thread.

If you are comfortable dating men who keep things from you, then that is your choice. If a man, or woman, keeps back a detail that he/she thinks will negatively affect a relationship, then that person is simply not being honest.

I find it amusing and hypocritical that you continue to semi-bash me for my opinions and preferences when I didn't bash the OP for his--I merely said that a crossdressing male isn't for me and IF someone kept that secret, he was a liar by omission.

I had a three month relationship with a man who, on the third date, told me he had engaged in sex with other men. I didn't dump him for that, but several weeks later when he also told me that he didn't think it was "stealing" to take things from work, he didn't last a lot longer.

There are just some things one wants to know upfront.
 dysfunction_junction
Joined: 7/17/2008
Msg: 36
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/7/2008 11:59:01 AM

I find it amusing and hypocritical that you continue to semi-bash me for my opinions and preferences when I didn't bash the OP for his--I merely said that a crossdressing male isn't for me and IF someone kept that secret, he was a liar by omission.

I had a three month relationship with a man who, on the third date, told me he had engaged in sex with other men. I didn't dump him for that, but several weeks later when he also told me that he didn't think it was "stealing" to take things from work, he didn't last a lot longer.


if you want to think i'm semi-bashing you, that's your perogative too! i doubt if i could say anything that would make you change your mind.... not as if you actually *care*. i did disagree with you that keeping cross-dressing a secret is ipso facto a "lie by omission". so we can continue to disagree on that point, k? k!

stealing is, ipso facto, a crime, and it would be reasonable for most people to dump somebody for committing a serious crime. i have no idea what "taking things from work" means. did he embezzle money? or did he just take a few pencils and a paperclip?
 Plastic Sturgeon
Joined: 12/5/2007
Msg: 37
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/7/2008 1:18:47 PM
Quirky;

I still look and can't believe, which got me to thinking! The hair is
obviously a wig! Duh, I know! And I realize how much something
that can even be fake, matters when it comes to attraction!

Call it shallow, who cares, but we are what we are, particularly it seems
when it comes to matters that push our sexual buttons! We can change
our belief systems and consequently our feelings, but this seems well near
impossible!

You remind me of the dark haired girl on the original Charlies Angels!
(Not Sebrena, but the other feminine one! lol) I liked Farah (Still do) but
the dark haired girl would do too! lol
 IWishItWasSummer
Joined: 11/11/2007
Msg: 38
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/7/2008 4:39:03 PM
The trouble is that it's your fetish and yours alone - hard for a woman to share it, unless she's a cross-dresser too, I guess.
I'm hetero, so making love to another woman - even though I know it's a guy - doesn't do it for me. So I'd be friends with you but not even remotely interested in a sexual relationship. There's nothing in your fetish that appeals to me.
I think your best bet is to look for bisexual women or a woman with a similar fetish.
BTW, if I was to become friends with a cross-dresser, there's no way I'm sharing my clothes with him. Bad enough having them grabbed by teenage kids.
 platypus_man
Joined: 8/29/2007
Msg: 39
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Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/7/2008 6:26:23 PM
Well, there seems to be no clear answer here, although I'm seeing that most would prefer to know up front. That pretty much eliminates real world dating, because I don't go out 'dressed up'.

Crossdressing, well, the mental health world doesn't know what to call it. We've been recategorized several times because of that. It's not an addiction, it's not a compulsion, it does not respond to any known therapy. Consciously suppressing the desire to crossdress works temporarily, until the desire overwhelms other thoughts and interferes with other parts of our lives. It's a more or less constant feeling that you're in the wrong clothes; kind of like, well, think of being at a formal function but wearing a bathing suit. Technically, you've covered any private areas of your body, but you feel uncomfortable none the less, and feel the need to change what you're wearing.

Most are just common misconceptions. Crossdressing is not an 'addiction'. If it was, you could stop it by addressing it as such. That doesn't work. A fetish is something that a person requires in order to get sexually excited, and usually involves one particular type of item, whether it be a baseball bat, a feather, or a pair of panties. It doesn't usually involve any entire outfits such as scuba gear or such, neither does it involve dressing completely in the clothes of the opposite sex. My crossdressing has nothing to do with having sex, and a large percentage of crossdressers don't do so for sexual stimulation. I don't have sex dressed as a female. Dressing up completely as the opposite sex to have sex is called transvestism. I know, to some I'm splitting hairs, but there is quite a difference in the behavior. A girlfriend wouldn't have to deal with or be faced with me wearing female clothing if she didn't want to; but it's only fair that she know that I do it, just the same, because at some point she's very likely to come across some evidence of that activity and shouldn't have to be surprised by it. As odd as it is for most of you to understand, that's the way it is for most crossdressers. While we would love for someone to love us for everything we are, we understand that there are some things that we will participate in without our partner's companionship, much as most men don't enjoy participating in going shopping with a woman for clothing, accessories and such (although I guess you could call this one instance where this would be a 'benefit' of dating a crossdresser, because we will gladly go shopping with you, although probably not to buy anything for ourselves).

There are no real straight girl-crossdresser dating sites. If you do a search, you will find some; but those are all populated by men, and men posing as girls. They put up a few fake female profiles to draw people into paying large monthly fees in hope of finding someone, but if you chat with the guys on there, no one has ever dated a girl from those sites. There is about half of one percent of women who aren't bothered with crossdressing, but I don't know how to find them. As there is no way in hell that I could ever 'pass', going out in public dressed up in female attire is just a recipe for disaster.

Last but not least, although it confuses the straight world to no end, most crossdressers are straight. Most gay folks dress in the 'appropriate' attire for their physical sex, so if you're looking for gay folks, well, they probably dress just like you do (at least the ones that I've met do). So, looking in the mirror might very well set off your 'gaydar'. Only in the movies do you see gay people dressing up as the opposite sex all the time, again, because those movies are written by straight folks who have no idea of what they're writing about. People like to think that they can spot homosexuals easily, by expecting them all to be 'flaming faggots' or 'bull dykes', but that's not the real world, folks. I think Rock Hudson and Lisabeth Scott proved that point wrong a very long time ago. The reality is, gay folks for the most part, are just like everyone else, other than what they do in their bedrooms.
 IWishItWasSummer
Joined: 11/11/2007
Msg: 40
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/7/2008 8:53:43 PM
Thank you for explaining that, Stellar. I spoke earlier with real ignorance.
In that case, yeah if you explained it like that to a woman you were interested in and she seemd reasonably intelligent and open-minded, I don't think it's a problem.
But - just one probably stupid question: if you don't cross-dress for sexual stimulation, than what for? Not feeling comfortable in clothes of your own sex seems fairly extreme. Do you feel like that all the time, or just sometimes, in which case you cross-dress to alleviate it?
 Ravishing Renee
Joined: 1/22/2007
Msg: 41
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/7/2008 9:04:48 PM
I dated a guy who assumed since I had once been married to a bi guy that I would understand cross dressing.... ( he didn't 'tell me up front.....) we actually had a good thing going on ... the sex was great....... I was a little concerned about his health...... he had almost gone blind once and had some surgery to restore his sight and I was worried about could I handle a blind guy if this became the case then he hit me with the cross dressing stuff...... I thought it wouldn't make a difference about how I felt.. he was always great to commit on my clothes and how well my outfits were put together.... and then one night when we were out he said to me he would like to like to take me home give me a bath.... shave my legs .. paint my face and do my hair... and then he wanted me to do him....... That killed it for me..... it wasn't long after that that he asked me to marry him..... I had to tell him I could not deal with his.... Um other side...... It is something most people don't understand ( I admit I am one of them).........Good luck in finding someone that it doesn't matter too..... but I can tell you this living your life in a closet won't make you happy either you have to be who you are... No matter who that person is.
 platypus_man
Joined: 8/29/2007
Msg: 42
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Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/7/2008 9:58:33 PM
This is for IWishItWasSummer, and no, it's not a stupid question.

If you ask 10 therapists of different disciplines, you will get 10 different answers. Freudians say everything goes back to early childhood and mother son issues, behaviorists say no, it's conditioning only. If you read every theory and try to fit something into one and only one, you go nuts.

Lots of things influenced me as a kid into this; I will email you with the rest, it's really not appropriate to post it all here.
 quirkyenglish68
Joined: 2/13/2008
Msg: 43
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/7/2008 10:53:44 PM
Not feeling comfortable in clothes of your own sex seems fairly extreme


I would like to address your question, I am perfectly happy to call myself a transvestite because for a part it is a fetish, I do get some sexual gratification from it, I will not deny it. But a large part of it is a way to experience being an alternative person, a chance not to be yourself - in times of stress this can be a great way to relax to escape all the frustrations the pressures of living life as your guy self. Every crossdresser has a different reason for doing it.

Yes the desire to dress is somewhat always there, it varies in intensity, and yes I need to dress to alleviate it or eventually I will get frustrated - not angry, but just imagine if you couldn't do your favourite activity for a while you'd get pretty frustrated too. Sometimes the desire drops, sometimes it gets to a point where I haven't had the desire to dress for a whole year - or more specifically the desire to dress isn't greater than the effort required to dress.

BTW I love being a guy, I only dress for a few hours each week, and even then there is only so many hours of dressing I can take before I need to be a guy again. 4 hours in high heels is enough for me... ouch!...

Crossdressers tend to borrow clothes from gf, wifes, females friends, mothers, sisters etc because they have to hide their activity, they don't have the opportunity or chance (or even nerve) to go buy clothes for themselves, so they borrow whenever the opportunity arises. Every crossdresser has done it, including me - sorry Mum.

But now I have my own clothes and makeup, girls you are always welcome to borrow mine ;)
 IWishItWasSummer
Joined: 11/11/2007
Msg: 44
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/7/2008 11:59:36 PM
Hey guys, thanks for your honest and intelligent replies. I've learned a lot.
 platypus_man
Joined: 8/29/2007
Msg: 45
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Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/8/2008 12:20:12 AM
Borrow clothes? Maybe in the beginning. When it started, I was given the clothes to wear. As I got in my early teens, I took a few of my sister's old clothes that she didn't wear anymore (snuck them out of the clothing donation bags before mom took them to the donation bins, pretty easy really). After that, mail ordering did the rest. Today's internet shopping makes buying anything pretty anonymous. Heels hurt, quirky? Try some different ones; even the same sizes will feel different from different manufacturers; worked for me.
 Gwendolyn2010
Joined: 1/22/2006
Msg: 46
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/8/2008 7:19:15 AM

So I'd be friends with you but not even remotely interested in a sexual relationship.


Exactly the point I have been making. I do not choose my friends based on their sexual preferences/orientation or how they look; for lovers, it is a different matter.
 LillyAmber
Joined: 7/26/2008
Msg: 47
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/8/2008 8:26:06 AM
When I was in my early 20's, a guy I use to hang with put on a dress of mine, borrowed a female friends pink hat, put on hose(with his hairy legs)wore make up, even though he had a mustache and beard. He held a pair of pumps in his hands, and complained they were hurting his feet.He did this while we walked through Wal-Mart, just to see reactions of people.
 packagedealx3
Joined: 2/4/2006
Msg: 48
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Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/8/2008 8:36:57 AM
I'm so not reading there pages but I think if you don't tell soon enough and then the bomb is dropped, no matter how discreet you try to be about it, a woman is going to feel betrayed, period. Doesn't matter what the content of the bomb is. They wonder if they can believe anything you say to them, trust is a fragile thing.

Conversely, if you tell them too soon, they haven't figure out whether they like you and are much less willing to invite something in their life that has to be "dealt" with. I suspect that timing will always suck but might I suggest another way of bringing it up?

Maybe find a comedy club with a cross-dressing comedian. Then instead of announcing I am a cross-dresser, ask her what she thinks about it. You will get an idea of whether she has any knowledge at all, whether she will immediately go to gay in her brain and other information that will allow you to figure out how best to approach it.

If you start off with the information you provided in this post, you are not gay, you would keep a locker and rent a hotel room when you want to hang out in drag, since you say you don't go out dressed as a woman, then she knows from the beginning that you are not an STD risk and that this really will have zero impact on her life unless you find that you need oodles of time hanging this way, maybe even the more closed-minded gals could give you a chance to see how things go.
 dysfunction_junction
Joined: 7/17/2008
Msg: 49
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/8/2008 8:41:15 AM
4 hours in high heels is enough for me... ouch!...

haha, i can barely make it for an hour and a half in those things
 swayzin
Joined: 11/23/2007
Msg: 50
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 9/16/2008 2:27:17 AM
great comments give them hell
Show ALL Forums  > Dating and Love Advice  > Crossdressing; tell up front, or wait? Another bad experience.