This is from the Dear Prudie column, kinda a Dear Abby at MSN.com
Dear Prudence,
Since last Halloween, I've been wondering about my husband. We dressed him up as a bride, and he made quite an attractive woman for our age (60)—almost no one recognized him. I had the lady at my salon do his nails, hair (wig), and makeup. He is a jokester and doesn't take life seriously, and we had a ton of fun. My girlfriends and I talked him into staying in character all weekend as a woman and had a barbecue on Sunday with a group of our friends. Since then, my girlfriends love having "her" accompany us during our outings, lunch, and golf. He seems to be enjoying it more and more and is always interested in the next get-together. He sees it as a harmless prank and a challenge to pull off. He is not effeminate in any way when not in character and never has been. His male friends tease him but also think it is a riot.
—Should I Worry?
Dear Should,
I hope your husband looks better than Rudy Giuliani during his cross-dressing forays. I myself tried to pass as a man for this Slate piece and found the experience both fascinating and disturbing. I happily retired my jockstrap after a single outing. Clearly, you were in on and enjoyed your husband's debut—after all, Halloween is about trying out alternate identities. But now that it's spring, it's perfectly understandable that you're wondering when the outings with "Mildred" are going to end. His enjoyment of this new hobby doesn't necessarily say anything about his sexuality, but it sounds as if it is beginning to destabilize yours—especially if when you go get dressed, you find he's wearing your favorite Wonderbra. You're asking me if you should worry, but only you know if you are worried and feel the joke has gone on too long. If it has, tell your husband that for your sake, it's time he gave up being one of the gals.
—Prudie
halloween crossdresser doesn't wanna quit?
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Carolynn
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halloween crossdresser doesn't wanna quit?
"It’s not given to anyone to have no regrets; only to decide, through the choices we make, which regrets we’ll have,"
David Weber – In Fury Born
David Weber – In Fury Born
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Miss Robyn
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fun dressing
After all these years of dressing I am finally going out as a woman. I would love to have a wife like you and your girlfriends. Trust me crossdressers are fun loving people and it should not be a threat to you or your marriage.
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Carolynn
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Well, you know, sometimes is hard to put the genie back into its bottle. 
This lady's hubby is apparently enjoying the society of her friends, and as long as they find the situation to be amusing, and it will eventually grow old for them unless there is strong enough femme personality there, then he is not too likely to feel that enough is enough.
She says he is about 60, and sometimes people wanting to crossdress but resisting for various reasons, or even living in denial about a need to live as a woman, "wake up" at about this time of life.
If any of that is so in his case, then the genie may well and truly be out of the bottle. His biggest fears would have been passing and what his friends would think, and now he has seen that he can "pass" and has a certain amount of approval for "playing dressup" from her friends and no outright hostility from his own, so far. As he continues it, if he does, he may well find attitudes of friends changing. Now its a lark to those "in the know" around him. What happens after it becomes not so much fun to them anymore and they start questioning between themselves why he is enjoying it so much is another question altogether.
All this presumes that the letter is genuine. People often like to "prank" advice columnists, and this particular one seems to have taken a large page from the wish fullfillment Halloween plots sometimes used in TG fiction. So, despite that what I wrote in previous paragraphs tends to be true, we might take the letter with a grain of salt, to put it in the vernacular of my grandfather.
On a whim, I put this post on hold and searched out a TG fiction website called Fictionmania, because it seems to have a reasonable searchable database of its thousands of stories. I used the key category of Halloween and found only 157 stores with this central theme out of nearly 10,000 stories, so I may be a bit off on my assumption of the popularity of the theme. I might add, that as a comparison, over 5,000 of the stories contained some femme/domme theme, so that far outwieghs the Halloween stories. Of the 157 Halloween stories, only three seemed to include wedding dress as a key word actually central to the story. So, for whatever it's worth.....
Sorry, its just an expression of me and my past life. Hypothesis, Data, Aceeptance or rejection of Hypothesis, Report. Hard to get over!!
Oh yeah, Janet, to correct a misconception, the first post is a repost of a letter sent to an advice columnist, and does not pertain to anyone on this forum. However, there are a number of people who regularly go out as their femme selves and have GG friends they like to associate with. Takes some trust and confidence and a bit of a thick skin at first to do the same, I think, but it is doable.
Love, Carolynn
This lady's hubby is apparently enjoying the society of her friends, and as long as they find the situation to be amusing, and it will eventually grow old for them unless there is strong enough femme personality there, then he is not too likely to feel that enough is enough.She says he is about 60, and sometimes people wanting to crossdress but resisting for various reasons, or even living in denial about a need to live as a woman, "wake up" at about this time of life.
If any of that is so in his case, then the genie may well and truly be out of the bottle. His biggest fears would have been passing and what his friends would think, and now he has seen that he can "pass" and has a certain amount of approval for "playing dressup" from her friends and no outright hostility from his own, so far. As he continues it, if he does, he may well find attitudes of friends changing. Now its a lark to those "in the know" around him. What happens after it becomes not so much fun to them anymore and they start questioning between themselves why he is enjoying it so much is another question altogether.
All this presumes that the letter is genuine. People often like to "prank" advice columnists, and this particular one seems to have taken a large page from the wish fullfillment Halloween plots sometimes used in TG fiction. So, despite that what I wrote in previous paragraphs tends to be true, we might take the letter with a grain of salt, to put it in the vernacular of my grandfather.
On a whim, I put this post on hold and searched out a TG fiction website called Fictionmania, because it seems to have a reasonable searchable database of its thousands of stories. I used the key category of Halloween and found only 157 stores with this central theme out of nearly 10,000 stories, so I may be a bit off on my assumption of the popularity of the theme. I might add, that as a comparison, over 5,000 of the stories contained some femme/domme theme, so that far outwieghs the Halloween stories. Of the 157 Halloween stories, only three seemed to include wedding dress as a key word actually central to the story. So, for whatever it's worth.....
Sorry, its just an expression of me and my past life. Hypothesis, Data, Aceeptance or rejection of Hypothesis, Report. Hard to get over!!
Oh yeah, Janet, to correct a misconception, the first post is a repost of a letter sent to an advice columnist, and does not pertain to anyone on this forum. However, there are a number of people who regularly go out as their femme selves and have GG friends they like to associate with. Takes some trust and confidence and a bit of a thick skin at first to do the same, I think, but it is doable.
Love, Carolynn
"It’s not given to anyone to have no regrets; only to decide, through the choices we make, which regrets we’ll have,"
David Weber – In Fury Born
David Weber – In Fury Born
