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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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 Sabrosura089
Joined: 11/29/2009
Msg: 76
Crossdressing; tell up front, or wait? Another bad experience.Page 4 of 8    (1, 2, 3, 4, 5, 6, 7, 8)
Crossdressing; tell up front, or wait? Another bad experience


^^This is part of who you are. Therefore, you wouldn't be happy having to hide this.

I would suggest you be candid about this as one should be about one's life period. I can't think of anything I would not be honest about from the get vs. later. It's not fair to the other party and it just makes things harder than need be.

I would suggest you find groups/sites that dabble in this lifestyle, and therefore more accepting vs. a vanilla site such as POF. Where this is probably not the "norm".............
 platypus_man
Joined: 8/29/2007
Msg: 77
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Crossdressing; tell up front, or wait? Another bad experience.
Posted: 12/22/2010 10:29:57 PM
There are probably sites where you can find people who participate in alternative lifestyles. You probably won't have much luck here, do some searching around and see what you come up with on other sites.

Yes, there are. But there are no sites for this one; there is one 'date a crossdresser' site, and it's inhabited by 99.9999999% men. Oh, and a few pictures of female 'ringers' they create to email us to get out hopes up and pay to subscribe, but then those emails disappear once you've paid to join (ask me how I know...). Over the years, various studies have shown that the number of women who WON'T date us is >99%, because for them crossdressing simply turns them off sexually. So, the best odds are in the sites with the greatest number. Even so, the chances are remote; consider this: I've read several times that in general, about one in either 12 to 20 persons (depends on the dating books you read) is even remotely compatible with someone, so splitting the difference, lets say one in 16. Add in the above. That leaves one in 1600 who are potentially compatible with a crossdresser. ONE. POTENTIALLY. Then subtract the number who, when faced with the reality of her man enjoying being dressed up as a girl, change their mind (that would include my ex wife). Maybe one in 5000? Then reduce to the age and geographical limits, and the chances of dating someone is basically the same as winning the lottery. As the commercial goes, I have a dollar and a dream, but that's about it.
 mysteriosa
Joined: 5/19/2006
Msg: 78
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Crossdressing; tell up front, or wait? Another bad experience.
Posted: 12/23/2010 7:49:12 PM
No, I don't think you should have left it longer. It's something people need to know so they can decide whether they can handle it or not. It's not just a question of you finding something enjoyable but that you need to do it. A woman getting to know you is going to be aware of this at some level and wonder how much control you have over it. You say you wouldn't dress in front of her or outside but is that true? I suspect she'd be wondering if it is something that would increasing be imposed on her, once she was involved with you, and then what would she do? Also, some women just don't like the idea of men dressing like women for more than a fun joke. It's a bit like smoking - you know other people do it, you don't mind them doing it elsewhere and want them to be happy, but you don't want it to be part of your life.

I'm sorry it reduces your chances with women but it may be best to accept that and just try to find those women who wouldn't mind by mentioning it early on. Flying under the radar is not a good idea. Maybe there are sites where there are women who are open to this? If you try to get to know the women first and then bring it in gradually as an idea, I think you will end up hurt and the women will feel deceived.
 valleyguyaz
Joined: 11/13/2008
Msg: 79
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 2/25/2011 7:26:28 AM
in a perfect world a person would be able to tell everybody about their fetishes up front.

in the actual world that we do live in it is probally better to tell only those rare few that are really okay with it.

this is sad but very true in my opinion.
 abelian
Joined: 1/12/2008
Msg: 80
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 2/25/2011 7:57:20 AM

Over the years, various studies have shown that the number of women who WON'T date us is >99%, because for them crossdressing simply turns them off sexually.

OK, then if we assume that number is accurate, then realistically, you have a choice: Wait for someone in that small fraction of a percent who is ok with crossdressing or cross off crossdressing as one of your must haves with a partner and stop crossdressing. Lots of people relegate certain things to fantasy land in relationships. You just have to decide what is most important to you because reality is not going to change.
 Helen0426
Joined: 6/2/2009
Msg: 81
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 2/28/2011 2:12:55 AM
Well, I don't know about studies, I'm okay with it. But I definitely would want to know right up-front. I just wouldn't like it to come as a surprise, is all, because, well, it IS unusual! And I don't like feeling "thrown." No one does.

But if I know about this going into a potential involvement, it's fine with me. I think we could have a lot of fun with it.
 platypus_man
Joined: 8/29/2007
Msg: 82
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Crossdressing; tell up front, or wait? Another bad experience.
Posted: 3/1/2011 5:19:34 AM
Reading through the posts since I've last been to this thread, there's an amazing number of people who think crossdressing is something we consciously chose to do, as if one day, we sat down, and said to ourselves, 'Gee, I'd like to start a hobby which will make me a pariah among all the people I might ever be attracted to, something that would brand me as a pervert by much of the world's population, and make me a social outcast to many others.' It's this kind of misunderstanding that causes most of the problems. The percentage of guys who wear girl's clothes for kicks is way lower than those of us who just feel an overwhelming need to do it; most have no idea why they want to wear girl clothes, all they know is that they can't stop for any length of time. For most, it's not a hobby. It's not something we decided to do 'on a whim'. It's something we're stuck with. It doesn't respond to treatment by any known means; it's not an addiction, it's not OCD, it's not a neurosis, it's not psychosis. Some think it's related to sexual identity disorders, but that's not always the case either. All we know, is that it never....goes....away....permanently. Some of us have had success suppressing the desire for various lengths of time; but it always comes back, and the longer we put it off, the stronger the desire is when it does return. For the most part, it's basically harmless; but what it does do, is alter the image we project to women, and it pretty much destroys sexual attraction to us for them.
 452
Joined: 11/1/2009
Msg: 83
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 3/3/2011 4:42:44 PM
I would not want to date a man who was interested in,and regularly dressed up as a woman.I would want him to tell me this fairly early on by at least the second date.
 452
Joined: 11/1/2009
Msg: 84
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 3/4/2011 10:01:29 AM
I find it strange how we can't talk about anything personal in todays society when dating, yet having sex on the first date is completely acceptable.It's almost like as a society we value our bodies less then we do our secrets.If cross dressing is nothing to be ashamed of then why would someone hide it? And if you are ashamed of it them why are you continuing to do it?
 ferfoxache
Joined: 2/4/2011
Msg: 85
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 3/4/2011 1:42:47 PM

I find it strange how we can't talk about anything personal in todays society when dating, yet having sex on the first date is completely acceptable.It's almost like as a society

I understand not being able to bare your soul but you can bare your ass.
I can't understand how you can bare your ass and then not be able to keep it bared.
Like you have sex, then run into the bathroom to put on some clothes so the person can't see you naked.


If cross dressing is nothing to be ashamed of then why would someone hide it?

Everybody poops, yet bathrooms still have doors on them, and are generally segregated.
I don't see many people squatting above a sewer drain and crapping in public, except near the pier in San Francisco.
What is the point of having anything more than one kind of underwear? Make it all mens briefs, women don't "have" to use the flap. You hide your underwear underneath your clothes, and if you are wearing anything but the cheapest most functional of any kind to avoid skid marks and leaks then you must be ashamed of it and hiding it, otherwise you would simply wear that and nothing over it.


if you are ashamed of it them why are you continuing to do it?

maybe people aren't strong enough to immediately change upon realizing they are ashamed of something, especially when it makes them feel good at the same time.
Maybe they aren't so much ashamed of it so much as feel they should be, or keep being told they should be.
 452
Joined: 11/1/2009
Msg: 86
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 3/4/2011 3:52:48 PM
Everybody poops, yet bathrooms still have doors on them, and are generally segregated.
I don't see many people squatting above a sewer drain and crapping in public, except near the pier in San Francisco.

No one feels shame about defecating.We do it in private because it is a private thing.There are some people that when they get into a relationship with someone they will do those things in front of each other.It's an issue of privacy,not shame.


What is the point of having anything more than one kind of underwear? Make it all mens briefs, women don't "have" to use the flap. You hide your underwear underneath your clothes, and if you are wearing anything but the cheapest most functional of any kind to avoid skid marks and leaks then you must be ashamed of it and hiding it, otherwise you would simply wear that and nothing over it.

You have more then one pair of underwear because they get dirty,not because of shame.For a woman wearing the cheapest you can get can cause some problems.We are supposed to be wearing cotton underwear.We don't wear the cheap ones not out of shame but because of health.

Cross dressing is a pretty big thing and for many people it is a deal breaker.A person should really tell the person they are dating early on so that if it is a deal breaker for the other person then they will not waste anymore time with someone not compatible.
 verygreeneyez
Joined: 3/15/2006
Msg: 87
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 3/4/2011 8:03:55 PM

Ray of Moonight: It really depends on the situation. Is the person a crossdresser than plans on getting a sex change or someone that crossdresses every day? Or are they someone that does drag performances once in a while? Or are they someone that has a crossdressing fetish in the bedroom. I agree you should be upfront about your lifestyle with other people but asking others to be upfront about sexual fetishes is absurd. A lot of people don't feel comfortable getting into things like that until you've dated for a few months. Expecting someone to tell you that on a second date is ridiculous.

I agree. There are as many variables with this topic as any other topic on sex. People preach and preach and preach here on POF, "It's what's inside that matters." Well, if that's the case, it shouldn't matter one damn bit what someone wears on the outer shell they walk around in.

~OT~ Would I date a cross-dresser? I don't know. I do know that my two friends that are men, are not having sex change operations, but have women breasts and men's genitalia as well, prefer to dress as women. I'd certainly go shopping with either one of them (impeccable taste on both accounts) but I'm not in a position to know if I'd date either of them. As human beings? I like them both very much. Guess I'd personally have to cross this bridge (or attire choice) if/when that time were to come. JMO
 ~breathlesshush~
Joined: 4/25/2006
Msg: 88
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Crossdressing; tell up front, or wait? Another bad experience.
Posted: 3/4/2011 11:47:48 PM
This is a tough one for me. To be honest, I would be on a "need to know" basis. Meaning, if I didn't need to know, then I don't want to know. I guess I would "need" to know if it was something he did on a daily basis, or something he wanted/expected/hoped I would participate in. If it was something that he did once in a while to satisfy his need(s) and it otherwise had no bearing (good or bad) on our relationship, I see no reason why I would need to know.

Why would I not want to know? The thing that attracts me to men is that they are... men . I like a masculine man; from the shape of their arms, butt and thighs; to the sound of their voice and the wiry stubble on their chin.

Now take that oh-so-masculine man and dress him in a lacy pink merry widow. It just doesn't work for me.

I have a lot of mens shirts; in fact, I often prefer mens tops to womens. I also have a jacket or two. I don't wear mens jeans or pants because I have hips and they just don't fit properly, otherwise I probably would. I don't wear mens' underwear either, but that's because I mostly think they're kinda ugly.

When I wear my "man" clothes there is a difference to a man who cross dresses in womens clothes however. I don't look like a man , nor am I trying to. There are clothes made for women that men could wear and not look feminine, in fact I'm sure some do (look at lululemon! lol). The point behind cross dressing I think (correct me if I'm wrong), is trying to emulate/experience the look/feeling of being the other gender. I won't claim to have the faintest idea why people do this, but then it's not something I've felt a need to do and as such am pretty ignorant as to the motivations behind those who do.

My oldest sister is a lesbian, and she also performs as a "drag king". She dresses in full male drag, even going so far as to wear a strap-on. I haven't seen her in full costume (unfortunately!), but have been told that she has been approached by gay men who thought she was a gay man. She's quite proud of that.

I honestly don't think there's a perfect time to disclose something like this to a potential partner. I do think you learn over time to spot those who will be very close-minded and rigid, and weed them out early on to avoid the inevitable. I also don't think it's "lying by omission" if you don't blurt it out over coffee at Timmy Ho's.

Yanno, interestingly enough when I finally watched the "Rocky Horror Picture Show" in it's entirety a few months back, I found myself oddly attracted to Tim Curry in his bustier, stockings, and panties...

JMO, of course.
 RubyWaxxx
Joined: 10/23/2010
Msg: 89
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 3/5/2011 12:18:43 AM
^^You're right, Tim Curry was HOT in Rocky Horror..
But he was hot in that role. He was soooo decadent.
 ferfoxache
Joined: 2/4/2011
Msg: 90
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 3/5/2011 8:24:27 AM

Why would I not want to know? The thing that attracts me to men is that they are... men . I like a masculine man; from the shape of their arms, butt and thighs; to the sound of their voice and the wiry stubble on their chin.
Now take that oh-so-masculine man and dress him in a lacy pink merry widow. It just doesn't work for me.

It could work for you.
I mean crossdressers dress because they came to associate the clothes and image with something sexual and liberating.
It's not naturally occurring behavior.
It's all training.
Everyone can be trained.

From what I've read some or a lot of crossdressers feel that the whole masculine role means they can't or are not supposed to feel things like sexy, that feeling sexy and sensual and desirable are female traits, only women are supposed to feel that way, therefore they (CD's) feel it necessary to adopt (what they view to be) feminine dress and potentially mannerisms in order to be able to express what they see as feminine traits but which are really universal human traits.
They have not been socially trained to express certain things except in a feminine manner.

Would you accept that?
If you were part of a relationship with an extremely masculine man, but he only knew how to be masculine, only knew how to desire you, how to desire your sexuality and sensuality, but not how to express the need to feel desired or desire sensuality or to communicate himself as a sexual person, and you cared about him, would you accept him as a crossdresser if you experienced with it his emotional change, that he was able to appreciate your desiring him, be able to see himself as desirable (rather than simply a sex opportunist "yay, she's horny vs. she's horny for ME), and the need for sensuality, and see himself as a sexual person?

If so, when is it better to tell you about his crossdressing? When you will understand what it does for him (later in the relationship) or when you will draw your own conclusions that aren't based on how he feels about it or why he does it, simply your own and how it reflects on you (in the beginning)?

I wonder how different any answers would be if it weren't primarily single people...


No one feels shame about defecating.We do it in private because it is a private

People do feel shame about defecating. I know I've crapped myself and felt shame.
How do you think most parents taught their kids to use the toilet? Make them feel shame or fear for not, or positively reinforcing doing it which is the same as not positively reinforcing failure to do so, meaning the kids going to feel negative for not getting that positive reaction. In todays society if it's not good, then it must be bad.
I've never met a kid that didn't feel shame and fear for wetting the bed.
We do it in private because it is a private thing...is it a private thing because we do it in private?


You have more then one pair of underwear because they get dirty

I was typing about types of underwear (hence the flap comment). Why have more than one type of underwear.
Why have more than one type of underwear, yet not wear it unless it is hidden.
Why is it different seeing a woman in a bikini vs. seeing her in her bra and panties.
Women associate sexiness with underwear. I have never met a woman that didn't have sexy underwear vs everyday underwear vs period/comfort panties vs shaping and control panties.
 karma1160
Joined: 6/10/2008
Msg: 91
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 3/5/2011 1:00:14 PM
while I can not profess to know why you would feel this way, I am not going to sit here and tell you to change your deepest desires.

I really think that life boils down to finding someone that can love you as you are, no matter what your preferences are.
I think when two people love each other, their private moments are their own, not for public scrutiny. While I may want to please my partner there are a few things that would be off the table for me. You need to find these things out soon.

YOu need to be upfront with someone right away. I have known people who have crossdressed that were not gay, but liked the feeling of being enraptured in a womans clothing as a sign of being nutured.

Like I say, I can not pretend to analyse this, I don't think that 99% of the population would be totally repulsed though. It neither repulses me nor excites me.
I am just one of those women who happen to like the male form so dressing it up in a dress would not apeal to me. Although kiltz are the cat's meow.
 *Bulldog*
Joined: 3/31/2007
Msg: 92
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 3/5/2011 6:02:01 PM
The guy confesses in his profile to having a childhood scar that has led to this preference [as can be the case with these sorts of things]. Just wiping that under the rug is not doing anyone any favors - particularly the OP.

Now the OP is likely long since removed from this thread but, whether it's homosexuality, promiscuity, cross-dressing, pornography, serial dating... you're not loving the person by suggesting they "just do what feels right." We all know from our own personal experience that that often leads to conflict, emotional problems, and heartbreak. Loving people don't "enable" this kind of behavior.

To think this kind of preference is just like preferring the color blue to the color orange, and thus saying everything is "okay," is condemning the person to a life unfulfilled.

My hope is that people entangled with these things have loving people around them to encourage them, counsel them, and strengthen their ability to form healthy human relationships.
 smittin
Joined: 11/6/2010
Msg: 93
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 3/5/2011 7:04:14 PM
Good question.

Maybe I'd be more open to considering such a thing if I had developed a personal interest in the cross-dresser than if it were just a hypothetical situation. I just wouldn't want it to go past the point of interest all the way to attachment before I got a clue, in case it wasn't something I could deal with.
 *Bulldog*
Joined: 3/31/2007
Msg: 94
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 3/6/2011 3:15:13 PM
People are happy when they're able to express themselves. People are unhappy when they're told to supress who they are.

We all know we hurt people -- bad relationships, broken lives, conflict -- by doing as we wish.. what makes us feel happy or comfortable often brings pain to others.

But what is lost in this is that we also hurt ourselves by doing what feels good or "expressing" ourselves. Often what feels good now - in the moment - feels bad a moment or a year later. These issues corrupt one's ability to form strong relationships in the future, and they form painful scars that are hard to overcome. I see it every day:

Girls hopping from one guy to the next because they've never had a stable relationship to model after (can't trust, invest in others, etc), and likely never will; porn addicts who can't be satisfied with a woman because they've been indoctrinated with a desire for variation, selfishness, a shallow view of women, strange lusts (women's feet, underwear, shoes, whatever), a lack of self-control, impatience.. ; homosexuals who can't find the balance/virtues they lack in the other sex and the joy of child-rearing; cross-dressers' desire to rebel against childhood expectations, issues with self-esteem and preoccupation with looks, or unreleased guilt and shame; whatever it may be.

People weren't born into having these problems, nor did they "choose" to have these problems. Often it just happens. It can be as simple as a father not giving someone enough attention or affirmation growing up (or the mom giving too much), being a sensitive kid in the wrong situation, or just the product of a bad relationship.

But loving people don't enable them. They let people who struggle with these problems know that change will lead to a more fulfilling life - for you, and your loved ones.
 valleyguyaz
Joined: 11/13/2008
Msg: 95
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 7/6/2011 12:28:56 AM
i think its better to be honest and upfront about this when you can do so.even if thats means explaining your reasons and situation.

 AtheistScholar
Joined: 6/18/2011
Msg: 96
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 7/6/2011 3:05:55 AM
I find it incredibly selfish that cross dressers would even contemplate keeping something so massive a secret. Every human being deserves emotional fulfillment, and they can only conduct that search with honest information in regards to their potential partner. Denying someone that is to literally deny them their most basic human right.
 Indysweetpea2001_
Joined: 8/1/2008
Msg: 97
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/30/2011 7:12:30 PM
Your only going to have bad expereince after bad experience if your dishonest with your fetish, because sooner or later it will be found out or youll make excuses to break up not tell it. Either way will end badly. The reason men do not tell is being selfish and wanting their own desires as a man satisfied most likely. So why put some unsuspecting woman in that position in the first place?
 statesshapes
Joined: 6/11/2011
Msg: 98
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/31/2011 4:09:02 AM
You got mental problems, due to abuse, so you need to talk with a psychiatrist and "get over it," or "move on." I will not knowingly get involved with someone who's been abused because I know they will have issues that I cannot deal with. So, I am sure this is how both sexes usually approach this situation.
 Indysweetpea2001_
Joined: 8/1/2008
Msg: 99
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 9/1/2011 6:45:23 PM
[If you were part of a relationship with an extremely masculine man, but he only knew how to be masculine, only knew how to desire you, how to desire your sexuality and sensuality, but not how to express the need to feel desired or desire sensuality or to communicate himself as a sexual person, and you cared about him, would you accept him as a crossdresser if you experienced with it his emotional change, that he was able to appreciate your desiring him, be able to see himself as desirable (rather than simply a sex opportunist "yay, she's horny vs. she's horny for ME), and the need for sensuality, and see himself as a sexual person? ]

Hmm this is in interesting thought, however we women do desire men just as men desire women, we do get turned on and sexually attracted just for him. However women are taught from birth to be more reserved in our expression of our wants and needs for sex. We do also when comfortable in a relationship and feel safe with a man let go of those reservations. A man crossdressing after seeing his partner's negativity about it, will not expereince the positive I desire you that he is supposedly doing it to get. It may further damage his self worth. You can communicate sensuality in many ways other than wearing women's clothing. The behavior to me is much like a good girl when drunk, the bad girl comes out to play and then she can blame it all on the alcohol. lol
 pinkoleander
Joined: 8/16/2011
Msg: 100
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 9/2/2011 9:19:34 AM
As a rule I prefer not to date or have relationships with men who have better clothes and know how to accessorize better than I do. And I hate to share my jewelry and purses.
Show ALL Forums  > Dating and Love Advice  > Crossdressing; tell up front, or wait? Another bad experience.