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 bustybabe
Joined: 2/26/2006
Msg: 1
i caught my ex boyfriend dressed like a woman Page 1 of 8    (1, 2, 3, 4, 5, 6, 7, 8)
i was freaked out and speechless when i caught my ex-boyfriend in a dress, heels,pantyhose,bra,makeup,
wig,etc.

when i confronted him later that day he told me he liked to dress like a woman and that he has done it off and on since he was 10 years old!!he asked me to help him look the part and act the part.but i was stunned he kept it from me for almost 3 years.i am open minded and accepting of weird and unusual habits/fetishes.lying and not telling me about this as well as other things broke us up in the end.

my question s this any other women caught their guys crossdressing?

any of you accepted it?

did it breakup your relationship with him?
 pleazin4u
Joined: 2/26/2006
Msg: 2
i caught my ex boyfriend dressed like a woman
Posted: 3/6/2006 2:43:42 AM
if he enjoys dressng like a woman then more power to him.


i agree with you that he should have been honest and open with you from the start.

when dressed could he pass as a woman?

 Shoedaddy
Joined: 3/2/2006
Msg: 3
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i caught my ex boyfriend dressed like a woman
Posted: 3/6/2006 4:11:22 AM

but the same question might be raised "Would you date someone with a terminal disease?", "Would you date someone with a mental disorder"
 Cyrix
Joined: 8/3/2005
Msg: 4
i caught my ex boyfriend dressed like a woman
Posted: 3/6/2006 4:30:05 AM
I don't think it's amusing at all. If he developed it when he was a 10 year old boy, what does that say? Clearly there are some milestones in his childhood that need to be discussed. If you are in a relationship with the person, I'd still go out with them, but I'd make suggestions to speak to a psychologist together (not a counsilor, as you don't need a shoulder to cry on, but some answers on one's past and how it intertwines with him as an adult).

It's a serious defect, and it needs to be addressed. Support once again will prove invaluable.
 MarkCK
Joined: 9/24/2005
Msg: 5
i caught my ex boyfriend dressed like a woman
Posted: 3/6/2006 4:38:49 AM
no there's nothing that needs to be discussed, don't be shallow

he was obviously unsure about his sexuality so he messed about a bit, fair go

it's not a defect, you're opinions defect - sure it's not what i'd choose, or something you'd choose to do, but if someone else chooses, that doesn't make it wrong.

personally yep it'd mess things up for me if my gf liked dressing up as a man, wouldn't do it for me
 Cyrix
Joined: 8/3/2005
Msg: 6
i caught my ex boyfriend dressed like a woman
Posted: 3/6/2006 5:00:26 AM
Interesting that 2 people have mentioned it is not a serious issue. I suppose it's the norm for 10 year old boys (when the author stated the issue started) to dress up in womens clothes at that age when their minds are molded like clay?
 ruthless75
Joined: 7/21/2005
Msg: 7
i caught my ex boyfriend dressed like a woman
Posted: 3/6/2006 5:20:28 AM
This happened to me too - I came home early from work to find my then boyfriend in a long black dress - My reaction was to say "It looks better on me..." He was embarassed and explained he had only done it from curiosity but he did get a kick from it. If I was a guy I too would be intrigued as its only clothes and as a woman we get to wear everything and guys clothes are limited. Sometimes we all like to do something that feels naughty and is considered wrong ...as long as we are not hurting anyone....whats the big deal? In your case this guy had kept it a secret for so long it probably become an issue to discuss.
 hulahoney
Joined: 10/24/2005
Msg: 8
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i caught my ex boyfriend dressed like a woman
Posted: 3/6/2006 10:34:19 AM
my exhub, total jock, man's man... liked to wear my panties before sex. it really aroused him. so i kept a large, really silky pair in my drawer for him. it seemed kinky buy hey, what did it hurt? the sex was always fantabulous!!!
 Fran_Gal
Joined: 2/20/2006
Msg: 9
i caught my ex boyfriend dressed like a woman
Posted: 3/6/2006 10:37:56 AM
why did you wait days to confront him I'm wondering

?
 justlooking101
Joined: 7/14/2005
Msg: 10
i caught my ex boyfriend dressed like a woman
Posted: 3/6/2006 10:39:50 AM
What the hell is wrong with people today, am I just really old fashion ? This is not right from the start. There is only one reason for me (a man ) to wear women clothes and that is when they come flying off her in the heat of passion and just happen to land on me, that is the only reason. There are some serious issues going on here. Be careful !!!!!
 Devil Fish
Joined: 10/31/2004
Msg: 11
i caught my ex boyfriend dressed like a woman
Posted: 3/6/2006 11:08:01 AM
Your EX was dress in drag?
 Intercooler
Joined: 2/18/2006
Msg: 12
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i caught my ex boyfriend dressed like a woman
Posted: 3/6/2006 12:27:41 PM
Look at it this way, you have a "girlfriend" to go shopping with now. Ahhh, there's always a silver lining...
 Fry Lock
Joined: 10/4/2005
Msg: 13
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i caught my ex boyfriend dressed like a woman
Posted: 3/6/2006 12:37:06 PM
nope; never dealt with that; I'm pretty open minded, but I think that would make me a little uncomfortable; if I was to happen up on that, I would beat a hasty retreat to the closest watering hole for a drink to calm my nerves before going back to get him outta my clothes... *shiver*
 Bramble
Joined: 3/2/2005
Msg: 14
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i caught my ex boyfriend dressed like a woman
Posted: 3/6/2006 12:38:04 PM
She has dated him for 3 years and there haven't been any real problems that she has mentioned that would require counseling.

The guy just likes to dress up like a woman sometimes.

It's not a big deal.

Who says a guy can't feel pretty once in awhile?
 Magickman
Joined: 1/29/2005
Msg: 15
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i caught my ex boyfriend dressed like a woman
Posted: 3/6/2006 12:46:40 PM
Was he cute?

No, seriously, I dated a girl with a moustache once. She got mad when I suggested a shave.

Stuff like this is troubling, for many people. It makes us wonder about underlying sexual orientation. I guess it was too strange for the OP. People have to make up their own minds about the limits of their tolerance.
 pnayplayr
Joined: 12/17/2005
Msg: 16
i caught my ex boyfriend dressed like a woman
Posted: 3/6/2006 12:52:42 PM
or you broke up with him cuz you couldnt' handle the fact that he looked sexier than you in a dress? hehehehe...i'm just messing...
 Fry Lock
Joined: 10/4/2005
Msg: 17
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i caught my ex boyfriend dressed like a woman
Posted: 3/6/2006 12:53:18 PM
He can be as pretty as he wants, just not at the expense of my sanity; nope, I don't think I could get past that..
 Bramble
Joined: 3/2/2005
Msg: 18
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i caught my ex boyfriend dressed like a woman
Posted: 3/6/2006 12:59:37 PM
Why do people automatically assume that putting on womens' clothes means that someone is unsure or in the closet about their sexual orientation? We'd need more information.
 Venusdomina
Joined: 9/9/2005
Msg: 19
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i caught my ex boyfriend dressed like a woman
Posted: 3/6/2006 2:49:45 PM
live and let live.
 FreshStart12345
Joined: 2/10/2006
Msg: 20
i caught my ex boyfriend dressed like a woman
Posted: 3/6/2006 2:53:43 PM
wow, i can for once honestly say that this has never happened to me......hmmm what would i do? Well, if he wasn't gay and he just liked to dress in drag the odd time.....i think that i would learn to accept it if i loved him....its a complusion just like any other disorder. But i would seek councelling individual and together if u decide to stick together cause it could be a cause of many problems and insecurities in the relationship.
 katzfun
Joined: 1/29/2006
Msg: 21
i caught my ex boyfriend dressed like a woman
Posted: 3/6/2006 2:59:01 PM
Why is it acceptable for women to wear men's suits .. but men to wear women's clothes is related to mental illness .. in the 1500's and the 1600's men wore heels and dresses :)

Here's my theory .. either accept him or move on .. sure .. he should have been honest with you from the start ... my issue with the situation is he should have been honest from the start .. not that he dresses in women's clothes .. would I date a man that wore women's clothes .. no .. its not my thing .. but I know not to try to change him .. because we are whom we are .. and can only change if we want to change .. not because someone wants us to change ..

Just my humble opinion
 Enryk
Joined: 12/15/2005
Msg: 22
i caught my ex boyfriend dressed like a woman
Posted: 3/6/2006 3:11:49 PM
Come on people, you go around telling every single fetish you have?

It is something which develops along the relationship... if it didn't come up during a 3 year relationship... maybe it was telling you something about the relationship itself? or probably he thought you wouldn't like it...
 4loorplay
Joined: 2/19/2006
Msg: 23
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i caught my ex boyfriend dressed like a woman
Posted: 3/6/2006 3:24:16 PM
LOL did he steal your shoes? Where did you catch him? Did he have extra money? Why would someone dress like a women if not a game in the bedroom? That's the real question you have to find answers for. IIIIIIIIII DONT KNOW!
 smilescolorado
Joined: 10/7/2005
Msg: 24
i caught my ex boyfriend dressed like a woman
Posted: 3/6/2006 3:27:36 PM
My question would be,did he look good in 4 inch italian heels and a leather skirt?
I would put my foot down if he wanted to wear my Natori push up bra with matching panties,
and use my Prada,Louis Vuitton bags, now that would push my buttons, I would have to say "NO" and send him to time-out. Just think you both can go shopping together and have fun. lol

 YEAIDID
Joined: 1/24/2006
Msg: 25
i caught my ex boyfriend dressed like a woman
Posted: 3/6/2006 3:37:47 PM
Im disturbed....It is adam and eve...not adam and steve. I stick with that. Men putting on womens clothes does not make sense and if i was a woman would be grounds for dismissal. Who knows what 'other' curiosities he has now or will have in the future? Next thing you know he comes home from wherever and his breathe smells dikky........no no no, he's got childhood issues that need resolution like someone earlier said...and thats MINIMALLY. Make a decision whether he is worth sticking through while they get ironed out.
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