Also check out Flickr’s male sissy maid pool
A 2004 article (but still very interesting) about a crossdresser (and Silverton, Oregon city official!) by Meg Daly:
Rasmussen says he has been a cross-dresser all his life, though he has only been out for the past 10 years. For many years he was ashamed; he thought he was the only man in the world with a proclivity for women’s clothing and therefore must be “sick and bad.” Then an Internet search revealed a much wider world to him and, he says, “the floodgates opened.”
He found his way to Northwest Gender Alliance, which he credits with helping him get to a place of being comfortable with himself. In the mid-1990s he started getting his nails done and was soon going out in public dressed entirely in women’s attire. Though he was terrified at first, he soon realized “90 percent of the problems [he faced] were right between my own ears.”…
Comfortable with the terms genderqueer and transgender, he says he has nonetheless never considered having a sex change.
“I can be perfectly happy in a man’s body,” he says.
He did, however, save up his money and get breast implants four years ago.
“Cleavage is a cross-dresser’s nirvana,” he says. He had worn prosthetic breasts for a few years to “try out being a guy with breasts.” Now that he has the real thing, he says he has regretted it “for all of about 15 seconds” when he first opened his eyes after the surgery.
One of his favorite adornments for his bust is a T-shirt he had made that answers any silent passersby who may be wondering, “Why does Stu do that?” It reads simply: “Because girls have more fun. ”
This blog has some advice about coming out as a crossdresser:
Within both society in general and the transgender community, there tends to be numerous dramatic tales of “The Wife Who Immediately Sought Divorce After Discovering Her Husband’s Secret Crossdressing Desire.” I extol my readers to not become caught up by such fears. The fact is, at least within my experience as a careprovider, those marriages which end solely on account of the discovery of a spouse’s crossdressing is a rarity. At worst, a shocked spouse may react with anger and severe disappointment. However, in situations where a spouse walks out the door upon discovery, there are almost always other problems with the relationship. Crossdressing becomes just another reason to end the relationship. My suggestion, if your relationship is on rocky ground, leave that secret wardrobe well hidden and out of sight.
In deciding whether disclosure is appropriate within a relationship, crossdressers must bear in mind that it is possible to pursue this activity in a manner which has no effect on a spouse or others. This is particularly so for persons who only dress occasionally, and have no interest in living “in role” as a member of the opposite gender. While this arrangement may not meet the expectation of one’s fantasies, it is possible to establish transfriendly relationships outside your marriage which provide emotional support, places to store clothing, and dressing opportunities.