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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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 swayzin
Joined: 11/23/2007
Msg: 51
Crossdressing; tell up front, or wait? Another bad experience.Page 3 of 8    (1, 2, 3, 4, 5, 6, 7, 8)
i always tell up front,and i have many many lady friends i go out with,,its the best way be honest
 GeneralizingNow
Joined: 10/10/2007
Msg: 52
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 9/16/2008 8:35:41 AM
It sucks that some people can't deal with your niche, but it IS a niche, so you know it's going to be even more difficult to find someone. I think you need to find a place where you can be who you are.

My friends would totally be okay with ANOTHER crossdresser in our midst. Our friend has no alternate name, though--he's always J. But we don't care if he's wearing a gown or a men's suit. I only wish he'd cut his hair, frankly--it's stringy. BTW, all, he's married and has a son. Totally hetero.
 ***blue***
Joined: 4/21/2008
Msg: 53
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 9/16/2008 11:42:51 AM
I don't know but I don't think it would be an issue for me.
I just see it as a quirk and everyone has those.
To each thier own.
 indehills
Joined: 2/23/2008
Msg: 54
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 9/16/2008 11:53:10 AM
I think it's best to be up front about ANYTHING major that might be a dealbreaker. I think most "biggies" are either going to be accepted by a potential mate or not, regardless of when you tell them.
 spitfire6844
Joined: 6/30/2007
Msg: 55
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Crossdressing; tell up front, or wait? Another bad experience.
Posted: 9/16/2008 12:07:42 PM

I think it's not necessary until you get to know if it's someone you'll be intimate with.


This kind of conversation should happen up front. It is a big deal and will be something that a lot of people won't want to overlook. Waiting a few dates before dropping this bomb is manipulative, and will generate an even stronger negative response. Always be honest upfront.
 carolann0308
Joined: 12/9/2006
Msg: 56
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Crossdressing; tell up front, or wait? Another bad experience.
Posted: 9/16/2008 12:09:49 PM
I just find it astounding that a self proclaimed straight male knows who Lisabeth Scott is.
 Dumpling-Girl
Joined: 7/20/2005
Msg: 57
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Crossdressing; tell up front, or wait? Another bad experience.
Posted: 9/16/2008 12:14:08 PM
My opinion is that it would be best to tell on the first date (or before, if there is communication before that, on the phone or online). I think you need to find yourself an open-minded girl for it to have any chance of working. If a woman is open-minded enough to have a serious relationship with a closet cross-dresser than she will be open-minded before you even start dating.

The alternative you present is that someone gets attached to you, and then you tell them, and hopefully by this time they are so attached, they are willing to overlook this, right? Well, I think that's asking a lot from someone who isn't open-minded about this stuff. They will feel a bit bamboozled if you went a while hiding this from them. That breaks down any trust that has been built up. And can cause her to worry about what else you are capable of hiding.

I think it's just better to find someone open in the first place, then it won't be so much of a concession to deal with for them, and easier all around. Don't date someone thinking you can change someone (in this case make them more open minded about cross-dressing), it's better to find someone who's already a good match for you.

I would respect someone for being honest with me right away. If I was attracted enough to a person, and he explained that it was something he would do on his own that wouldn't interfere with our intimacy, then I might give it (dating him) a shot. I would be taken aback if he started dating me and sprung it on me, even though I am fairly open-minded about this stuff.
 Plastic Sturgeon
Joined: 12/5/2007
Msg: 58
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 9/16/2008 12:22:20 PM
Do it quick and get it over with! Yay or Nay!

How about this? First time you are at one or the others place,
slip away to the washroom with your girlie threads in hand, change,
and make an appearance!

Don't forget to say " Tah Dahhhh!" As this always helps to break the tension!
 Helen0426
Joined: 6/2/2009
Msg: 59
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/2/2010 2:07:52 PM

People don't think twice if you own a gun, but for some reason it's a big deal if you own a pair of pantyhose?

*laughin'*

Other way 'round for me! Panythose, fine (you won't get me in them, but if you wanna wear 'em, knock yourself out); firearms, eh, I'm not going to freak out about it as long as they're kept locked, but I'd just as soon you didn't have 'em.

 Kazzmere
Joined: 7/22/2009
Msg: 60
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/2/2010 4:37:19 PM
I dated this fabulous man I met here on POF for a bit. Handsome, funny, erudite, sophisticated & generous. On our fourth date he decided to tell me the "truth" about how he made his living. What he had written on his profile wasn't true.

I did my best to not be judgmental about his chosen industry, but had he told me up front, before our first date, I would NOT have wasted our time and energy on those four dates, plus all the calls and e-mails that went on between meet ups.

I wish he had told me up front. Nice guy, just not for me.
 verygreeneyez
Joined: 3/15/2006
Msg: 61
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/2/2010 6:42:20 PM
~OP~ The only problem I see with your dilemma is that you have nicer legs than me. Seriously, I'm sure it's a lot for someone to take in, especially in the beginning. BUT, I think I'd personally be more concerned with the childhood stuff than the fact you like to dress unconventionally. Good luck to ya.
 aaamm
Joined: 7/5/2009
Msg: 62
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/2/2010 7:19:41 PM
Maybe I missed this, but is there a reason you don't have pics of you not crossdressing - clothing you would wear on a date? I think you have to be upfront about most non mainstream things, but you said you date in male clothing, why not have pictures of the way you would actually go out?
 Wicked_Cricket
Joined: 9/26/2009
Msg: 63
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/2/2010 7:36:08 PM
note to self: first chance u get, go thru guy's closet & drawers, check for better clothes/shoes than mine
 IgorFrankensteen
Joined: 6/29/2009
Msg: 64
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Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/4/2010 11:08:29 AM
I've only known one crossdresser in my life, and I know that he found both a fine relationship which still exists (they married within two years of college and are still together), and he eventually left his crossdressing days behind, AFTER he was with his wife for some time.
As far as when to tell, the only thing I can say for sure, is that if it's going to kill the relationship, it will kill it whenever you tell, so sooner is certainly more cost-effective than later. Like anything out of the ordinary, it's up to you to accept that your special attribute will narrow your available mates, just as any kind of attribute does, including birth defects, sexual orientation, addiction to tobacco, etc etc.
 Helen0426
Joined: 6/2/2009
Msg: 65
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/4/2010 2:47:28 PM
You may be right, Spagett! (heh - cute), that it should be right up-front. I'd be okay with hearing about it later, but then, that's probably in large part because I'm okay with it!

Editing to add, the original poster - over two years ago, so I doubt he's still reading - did refer to having lingering problems due to childhood abuse, in the opening post. Evidently this was okay with the woman he was dating but the cross-dressing was not. I believe the point was that this constituted a pretty backwards way for her to look at the two things... and I agree.
 acuddler
Joined: 10/30/2009
Msg: 66
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/6/2010 2:09:49 PM
Put it in your profile. Then you will know that the women who contact you don't have a problem with it. Of course, fewer women will contact you...but those who do will be more accepting. Many crossdressers are gay, and many are not. Few 'normal' people have much education about such things, so they go by gut intsincts-which say crossdressers are weird, and probably gay-and by movies/novels which suggest they are gay, weird, and homicidal.

There are online sites-clubs, fellowships, etc-where crossdressers-and those who love them-can socialize. Join a few. Maybe you'll meet a gal whose crossdressing BF/hubby died a year ago, and left her looking for another. To most people minds. crossdressers are gay, and child molesters...like Michael Jackson. He spent a lifetime getting cosmetic surgeries to look like Diana Ross. He dressed in womanly sequins, etc. He did with his face what you do with clothes. Some people will always think of MJ as a child molesting pervert; whether he was one or not. Many will feel the same about you. There will always be people who will never accept you once they know you crossdress, and they will fear, and hate, you. A woman who may be able to accept you may worry that her father, brothers, coworkers, etc, would not accept you, and so she would hesitate to become involved with you for fear of others learning about your habit, and taking it out on her.

Be open from the start, or change your ways. Get into show biz as a crossdressing comedian. Let the crossdresser part of your persona seem like just a show biz act for the sake of getting laughs. People will be more accepting of it then, and you will satisfy your urges without causing much trouble. Be a crossdresser who makes fun of crossdressers. That is ok, as the first rule of comedy is "you only knock your own". A Pole can tell polack jokes, but others should not. Fat women can tell fat lady jokes, but skinny men should not. As a crossdressing comic, you can satisfy your urges, do so in a more socially acceptable way, avoid having to hide your habit, and get paid for it all to boot. Once you are a headliner in Vegas, woman will flock to you.
 longhairbadass
Joined: 11/30/2009
Msg: 67
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/6/2010 5:07:57 PM
I'm sorry. I'm just never gonna get it. I'm never going to understand crossdressers. Some fetishes I can kind of understand. But I'm never gonna get crossdressing. And I have played in an 80s hairband, and wore spandex, and makeup, and sequin shirts. One band I was in dressed in drag every halloween. I'm just never gonna get it. Maybe its the fact that I'm an ugly man, and I'm a really ugly man dressed up in drag. Got no desire to wear pumps. They hurt my feet. Got no desire to wear womens panties, although I've ended up in them drunk in the dark after a show, and a ride home. Got no desire to wear dresses cuz I've got whiteass chicken legs. Got no desire to wear padded shoulder blouses because I have broad shoulders already and look like flippin fenders on a 57 chevy. I got no tits so a bra looks absolutely ridiculous. I don't have the form or function. But I do have a cute little ass. But its a guy ass. My fetish is guy crap. Money, motorcycles, toys, guitars, tangible investments. Give me a mingh vase, rug- pre persian dynasty, 70 hemi cuda, 58 les paul, 67 marshall stack JMP superlead, silver boullion, an invert jenny postage stamp, and or hawaiian, or ryiakus, a goldpan full of fresh dug nuggets, a beer, and a 14,000 foot vista to overlook after climbing it, and I'm good. Way better than a 10 dollar pair of panties. I just don't get it.
 longhairbadass
Joined: 11/30/2009
Msg: 68
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/6/2010 5:16:20 PM
I guess in this situation honesty is the best policy. And check your expectations. You're expecting too much if you think everyone is just going to accept your fetish of crossdressing. I won't knock your crossdressing fetish if you don't knock my vintage guitar collecting fetish. You like Liz taylor. I like taylor acoustics. Seems reasonable.
 aaamm
Joined: 7/5/2009
Msg: 69
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/7/2010 4:58:14 AM
8/6/2008 is when this was posted, a year and a half ago. I think the OP really is handling this now the way he wishes to.
 ToughLuv1984
Joined: 9/2/2009
Msg: 70
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/7/2010 1:49:11 PM
This is not something you should keep in the closet. (Pun intended). Its hard but with more people doing like Harvey Milk and 'owning it' out in the open, change will come to the day when there isn't such a rigid 'masculinity' preservation cult telling people what kinks or preferences they should have.
 voshie
Joined: 9/22/2009
Msg: 71
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/7/2010 9:02:48 PM
you should be upfront about something thats a real deal breaker for yourself if an intended woman is in the pic so she can make an educated choice ..being left out in the cold on such things as this is more hurtful down the road than if you were to actually get caught all dolled up while out on the town
 startle
Joined: 7/22/2008
Msg: 72
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/8/2010 5:49:57 PM
anything in your past which is probably not going to go over too well should never be discussed....the time to go into it is if there is a very close bond and then you will start unloading all the past experiences good and not..also every aspect of your life ...that is for people you feel safe with and trust....you don't have to reveal everything to people you are merely dating....
 TallChick61
Joined: 1/21/2010
Msg: 73
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 2/2/2010 9:23:22 PM
If it's a dealbreaker - whatever the issue is - disclose it up front.

Maybe she'll say no right then, maybe she'll give it a chance, maybe she'll be cool with it right off the bat. At least you'll know instead of worrying about it.
 minxinheels
Joined: 11/8/2010
Msg: 74
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 12/22/2010 4:10:31 AM
Honestly, I don't think cross dressing is a big deal at all. Most (legal) sexual fetishes are not, although I'm not even sure cross dressing is a sexual fetish, it's really not any big deal.

The problem is the amount of frigid ****es out there. I've dated a couple of cross dressers and it's NEVER ever been an issue at all for me.

Everyone has their kinks.

I'd be up front about the cross dressing, but maybe not the abuse. That's just me and not something I'd be comfortable discussing until I knew someone really well.

So you like to dress up in ladies clothes. Big deal. Honestly, if you just state it like fact and treat it like it's normal, other people will too.

You should not have to be with someone where you have to "hide" who you truly are.

If someone cannot love ALL of you, they do not deserve to be with you.
 carolann0308
Joined: 12/9/2006
Msg: 75
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Crossdressing; tell up front, or wait? Another bad experience.
Posted: 12/22/2010 9:58:22 AM
I would want to know upfront about a fetish like that, because honestly it is not something I would be comfortable with. Many women are more open minded than I am and certainly would be more accepting. So why even chance it?
A partner that supports your fetish and leaves you with nothing to hide or fear, is the best scenario for both of you. A true love relationship has to be completely open to each others needs.
But I do have to say to you OP, if there are childhood issues that are still affecting your sex life today then you have to be in a support group or individual therapy until the issue is no longer holding you back from enjoying your life.
Good luck to you.
Show ALL Forums  > Dating and Love Advice  > Crossdressing; tell up front, or wait? Another bad experience.