Plentyoffish dating forums are a place to meet singles and get dating advice or share dating experiences etc. Hopefully you will all have fun meeting singles and try out this online dating thing... Remember that we are the largest free online dating service, so you will never have to pay a dime to meet your soulmate.
     
Show ALL Forums  > Dating and Love Advice  > Crossdressing; tell up front, or wait? Another bad experience.      Home login  
 AUTHOR
 IWishItWasSummer
Joined: 11/11/2007
Msg: 51
Crossdressing; tell up front, or wait? Another bad experience.Page 3 of 8    (1, 2, 3, 4, 5, 6, 7, 8)
Hey guys, thanks for your honest and intelligent replies. I've learned a lot.
 platypus_man
Joined: 8/29/2007
Msg: 52
view profile
History
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: 53
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: 54
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: 55
view profile
History
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: 56
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: 57
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 9/16/2008 2:27:17 AM
great comments give them hell
 swayzin
Joined: 11/23/2007
Msg: 58
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 9/16/2008 2:28:49 AM
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: 59
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: 60
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: 61
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: 62
view profile
History
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: 63
view profile
History
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: 64
view profile
History
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: 65
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!
 pirateheaven
Joined: 5/11/2008
Msg: 66
view profile
History
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 9/16/2008 12:31:42 PM
You have gotten good advice so I will give you some to lighten the mood.

Just find a woman who has the same shoe size/dress size. Ask her how would she like to have her wardrobe doubled. Then tell her the news.
 Coma White
Joined: 4/11/2004
Msg: 67
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/2/2010 3:22:14 AM
I don't believe it's something you must put on your profile if it's not a huge part of your life. It's not like women are going to list all of their fetishes right on their profile. I hate keeping things a secret and I cross-dress when I do concerts and it becomes part of my act. It's not a character, it's just me being myself and turning up the volume. I've actually had more attention from females when I was dressed up than in my every day life. I don't think anyone should have to hide it or live in the closet. If people have a problem with you, tell them to get lost. As far as the bedroom goes, I would dress up if the woman wanted me to, but it's not something I have to do. I guess I don't see it as a big deal, or a "bomb". I don't consider it dropping a bomb if a woman tells me she likes cherry ice-cream on the third date. 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?
 Coma White
Joined: 4/11/2004
Msg: 68
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/2/2010 1:04:09 PM
That's awsome that you don't live in the closet Transvestite Biker. Do you ever get people giving you a hard time? I never saw it as a big deal, it's just clothes. Women wear pants now, whoop tee do. I was in drag one night after a concert, and a big jock guy said that he would dress like me all the time if he had the courage. I thought it was funny since he was twice my size. I guess the bottom line is there will be girls that like it, girls that hate it, and girls that don't care either way.
 Helen0426
Joined: 6/2/2009
Msg: 69
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.

 Jordanjamesx
Joined: 9/26/2009
Msg: 70
view profile
History
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/2/2010 4:16:28 PM
. Maybe the OP's girlfriend would be accepting that he crossdresses but that's a huge bomb to drop on someone. I honestly, don't know what to say? I mean, do crossdressers have to crossdress is it a mental illness or something or an addiction? First, I am a gay male and no I have never crossdressed in my life. Also, there are plenty of gay men that are turned off by men that crossdress. The reason why is why would we want a guy that wears women's clothes? I wouldn't want a guy that crossdresses because that's a turn off I prefer men that are masculine men. Most gay men do not cross dress. The guys that cross dress many are actually heterosexual they get a sexual charge from cross dressing. The other transvestites are draq queens they are performers and they crossdress because they are entertainers.
 Coma White
Joined: 4/11/2004
Msg: 71
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/2/2010 4:34:15 PM
You're right. Although I don't really feel it's a big "bomb" to drop. A lot of women wears pants to a date. All of these hang ups are just in peoples' heads and they're afraid of things that stray from the social norms. I think it's dropping a bomb if someone admits to murdering someone and hiding the body in the woods. I wouldn't care if I was on a date and a woman told me she had a particular fetish or special interest, like a foot fetish or some sort of bondage thing. What am I gonna do? Giggle and turn red? I'm not 14 years old, I can handle it. I'd probably try whatever she was into and if I didn't enjoy it, I would just be like "hey, I don't enjoy that" and work it out from there.
 Kazzmere
Joined: 7/22/2009
Msg: 72
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: 73
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: 74
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: 75
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
Show ALL Forums  > Dating and Love Advice  > Crossdressing; tell up front, or wait? Another bad experience.