Colin McRory lies on an operating table in the middle of a room in Thailand, a surgical team towering around him. A nurse dressed in white asks if he is excited about the procedure that will soon change his life, but his anxious smile says it all. Before he knows it, he is fast asleep. He will be under the knife for seven hours, and his operation will total $8,000. McRory will go into surgery a man, but will wake up a woman.

“I knew I wasn’t a guy when I was three-years-old,” says McRory, who has adopted the first name "Nicole." Over two years after the surgery, which was recorded in a documentary, the tall, peachy-skinned singer/songwriter recalls always having felt out of place in her own body. “I looked in the mirror and saw a dick and I was like, ‘That’s wrong, it will go away.'"

But what the little guy didn’t know was it wouldn’t go away that easily. It would eventually result in the loss of a marriage, home, business and family.

McRory is one of 8,000 people in San Francisco who believed her brain did not match her body and decided to have surgery to fix it. “A transsexual is someone who has the sense their sexual gender identity is different then their body,” says Gilbert Herdt, director of the human sexuality department at SF State. “A transsexual is nothing like transgendered. Transgendereds [unlike transsexuals] are highly opposed to having their genitals changed. They like the ambiguity of having both masculine and feminine traits.”

The idea of transexuality was first diagnosed in the 1880s by German doctor Richard Krafft-Ebing. He documented what he called "metamorphosis sexualis paranoia," which describes individuals who believe they are born the wrong sex. Unlike doctors today, Krafft-Ebing labeled the disorder a mental illness. Currently, the question of whether or not transsexuals have a mental illness is controversial.

Michael Brownstein is one of the few San Francisco surgeons who performs gender reassignment surgery. He has been in the business for more than 20 years. According to Brownstein, a patient must be diagnosed as a transsexual by a therapist before a doctor can perform the operation. Once they have been chosen to go through the process, they are placed on Brownstein’s waiting list, which can run up to four months long. For some, coming up with the money is not easy, especially since the surgery can cost up to $80,000. “Some of [the patients] have the money saved up, some of them get it from their families,” Brownstein says. “But a lot of them can’t go through the surgery because they can’t afford it.”

The surgery requires a time investment as well. Male-to-female transsexuals, also called MTF, are required to live as women full-time for two years and take hormones before they are able to go through the surgery. McRory injects 40 milligrams of estrogen into her buttocks every two weeks, and takes 200 milligrams of spirinolactone, a testosterone suppressant, daily. “It changes your hair and skin, and you start to develop breasts, which I really like,” McRory says, looking down at her breasts and squeezing them together. “I’ve wanted [these] for 50 fuckin years.”

Jennifer Kennedy, a 47-year-old software engineer, has been on hormones for about two years. “I’m a likely pre-op,” Kennedy says, meaning she will likely have the sexual reassignment surgery to become a woman. “My partner would prefer me to keep my current genitalia, but if it stops working, or we split up, I’ll get it done.”

Unlike McRory, who says she hasn’t been intimate since her surgery, Kennedy is married. She has been with her partner, Chris Kennedy, for 16 years. “I had no idea ... no clue that it was coming. It was just a complete surprise,” Chris says. “When she revealed to me she was transgendered, it was really hard.”

Since Jennifer’s revelation, the couple has endured extensive counseling. “As far as our relationship goes, we actually get along a lot better because fundamentally she is really happy,” Chris says.

But Jennifer’s wife isn’t the only one who is affected by her gender identity. Their two small children are as well, and according to their parents, they don’t have much of a problem with it. "I think my daughter, who is nine, is supportive. She is a little more distant than she was before, but she’s that age, so it’s hard to tell,” Jennifer says. “My son, who’s five, is a little more confused, but he’s amazing. At day camp, I over heard some kids asking him [about me and he said] ‘Yeah, that’s my dad who’s also my mom. He’s both a boy and a girl.’ People might question transition with kids, but I think it’s a great thing.”

Bonnie Bryan, 30, is in a similar situation. She has been living as a woman for two years, but is unsure of whether she wants to go the whole nine yards. “I'm on hormones right now,” she says. “I’ll figure it out later.” As a child, Bryan recalls stealing her mother's clothes. “It was pretty easy actually," she says with a laugh. "My mom kept her spare winter clothes in my closet."

To the average onlooker, Kennedy, Bryan and McRory’s mannerisms are feminine. It's the little things a traditional girl doesn’t have to think about–walking, talking, the way to hold a purse–that transsexuals have to get used to. These three have come to do it well, but for some, mastering the feminine image is not easy. That’s where feminine coach Denae Doyle comes in.

“It’s all new to them,” Doyle, star of the reality TV show “He’s a Lady,” says in a telephone interview. The image consultant created “Femimage,” a business that teaches male-to-female transsexuals how to act feminine. Doyle works with the women on voice, movement, makeup, hair and wigs. “A lot of times they spend so much money on the doctors that they don’t have money to spend on things that will make them look better,” she says. “They gotta have a good wig, not some goofy, cheap blonde wig.”

Meanwhile, McRory stands on stage in an Irish pub in downtown San Francisco at one of her weekly singing gigs. She wears a short skirt, high boots and a guitar with a strap that says “Pussy.” With her long, red hair resting on her shoulders, she is far from a cheap blonde wig-wearing man. She starts her performance in a soft, subtle voice. Just when she senses the crowd has diverted their attention, she lowers her voice and belts out notes so low they can only be sung by a male, or someone who used to be one. She proceeds to answer some of the crowd’s questions before they even have a chance to ask. “Yes, Yes, and Recently,” she says. “And for those of you who are feeling a bit uncomfortable, it’s just a tad of homophobia.”