Toronto (Don) Jail guard Andrea Roussel loves to tell the story about when a former inmate tried to pay her a major compliment.

“Yeah, and I got rid of them,” Roussel replied.

The prisoner meant his words figuratively, but Roussel was being literal. She’s the only jail guard in the history of the province — and perhaps the country — to undergo a sex change and continue on the job.

For almost 20 years, Roussel, 45, has been responsible for the care of some of Canada’s toughest and most troubled male inmates, including outlaw bikers and gang bangers.

She started the job two decades ago as Andre Roussel, a married father of two and former elite wrestler and football lineman.

For the past 2 1/2 years, since gender reassignment surgery in Montreal, Roussel has continued her work guarding prisoners at the Don.

In her first-ever interview, Roussel told the Toronto Star that her personal journey has included two suicide attempts, profound loneliness and therapy.

There were plenty of rough days, but none more so than on July 1, 2007, the day Andre Roussel publicly became Andrea Roussel.

That’s the day she began dressing as a woman 24/7, donning a wig over her bald head and wearing a skirt on the job.

“I was scared. I was afraid they’d ridicule me. I was afraid they’d pull off my wig.”

Roussel was verbally abused by prisoners in several languages and worried that she might be physically attacked as well.

Part of her job had been to take part in strip searches of inmates. When Roussel began presenting herself as a woman, prisoners rebelled and refused to consent to the searches.

“It grew like wildfire through the institution that a tranny was there.”

She found herself having to cope with profound feelings of isolation. On Christmas Eve 2007, Roussel couldn’t stop crying when she left the jail realizing no one had wished her season’s greetings. “Nobody gave me a Merry Christmas, a hug or a handshake. I cried all the way home . . .

“I cried. I said, ‘It’ll pass. It’ll pass.’”

She refused to leave the job that she knew she was good at, even though prisoners were often abusive.

One night, when the prisoners’ heckling became too much, Roussel quieted them by cutting off their cable TV for a night.

Roussel said she first suspected she wanted to be female at the age of 8, while growing up in Sudbury.

As a young boy, Andre was beaten up by a girl in his hometown in an argument over a skipping rope.

After the skipping rope spat, Roussel’s parents thought he should get into contact sports to be toughened up. Andre ended up excelling in wrestling and football, but never felt quite comfortable.

“I was kind of pressured by my parents to be the boy they wanted.”

At nights, when Roussel’s parents were out running their dance studio, Roussel would secretly sneak into his mother’s closet to try on her clothing.

He wrestled and played football with an intensity that brought plenty of awards and recognition. “I used to practise every day. I didn’t want to go home . . . I tried not to go home. If I went home and wasn’t busy, the urge of being Andrea would be too strong.”

“I enjoyed inflicting pain because I got to release pain — inner pain.”

After high school, Roussel fell in love with a woman and tried to suppress his feelings. To stay closer to the woman he would marry, Roussel found work as a guard at the Barrie jail in May 1990.

Roussel was one of the tougher guards in the building. (In the interview with the Star, she declined to give her weight, but says it translates to a woman’s size 24, with a 22-1/2 inch neck.)

Once, when a prisoner punched him in the mouth, Roussel subdued him with a wrestling suplex move that left the inmate crumpled on the floor.

Another time, before the sex-change operation, a prisoner grabbed Roussel’s testicles and squeezed hard. “It took five blows to the head for him to release. His face didn’t look like a face when I was done.”

Both incidents were considered justifiable use of force.

Despite the outward toughness, something was exploding inside him. He couldn’t suppress his urge to dress in woman’s clothing. Those were the early days of the Internet and he didn’t know anyone else with similar feelings.

He hid his inner feelings from everyone, including his workmates, parents and female lover.

Once, while he was working at the Barrie jail, Roussel’s girlfriend phoned him in tears. She had been cleaning Roussel’s room, found women’s clothing and suspected he was having an affair.

“How can you explain size 11 shoes? How do you explain a size 20 dress? A wig? Makeup?”

They went for a ride in his car and Roussel finally opened up. “That was the first time I ever told anybody about my secret.”

Roussel promised not to dress as a woman and, for a decade, he was able to honour that promise. “As the years go by, the urge is getting stronger and stronger. I’m getting jealous when I go shopping with her for clothes.”

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Finally, Roussel told his wife he couldn’t suppress “Andrea” any longer. “After a while, she got repulsed by me in bed because she felt she was hugging and kissing a woman . . . She realized it was a woman having a relationship with a woman, and that’s not what she asked for in this marriage.”

Eventually, it was too much for Roussel’s wife and she moved out.

There were also growing tensions on the work front.

Roussel came forward to Corrections management in August 2005, and they began working together to devise a workplace plan.

He attended the Southern Comfort Transgender Conference in Atlanta, getting ready for the change. “I lived as Andrea for three weeks, 24/7,” he recalls.

Then, after almost a month of life as Andrea, it was time to return to Toronto and present himself as Andre again.

“Putting away the clothes, it was so hard. I felt like I had died again.”

After consultations with senior management, the decision was made for him to gradually transition towards presenting himself as a female.

At the dungeon-like Don jail, inmates and staff noticed gradual changes in the massive guard.

“Back at work, people started to notice my arms being shaved, my eyebrows being plucked. People were wondering if I was gay.”

After a year of presenting himself as a woman 24/7, Roussel went to Montreal for the sex-change operation that made the transformation complete.

Now, she is on such good terms with her ex-wife that they sometimes shop for clothing together. Roussel tends to like girlier, frillier fashions than her ex.

She is also on such good terms with her ex’s new boyfriend that he has fixed the deck on her home.

“I like her boyfriend. If it can’t be me, I want it to be him.”

Roussel says that she feels far happier than in her days as a man, although she jokes that her golf game has suffered, with breasts impeding her swing and the loss of muscle mass.

At the Don, she’s no longer involved in strip searches, and verbal assaults are “minimal.”

“The inmates know if they say one word, they know they’re going to be locked up immediately for the rest of the day.”

She has enormous praise for her employer, for allowing her to grow in her job and counsel others. Despite the abuse she has suffered, she said she still loves her work and feels genuine empathy for prisoners, including tough gangstas.

“The only family they know is the mob or the gang that they hang with. As soon as you draw them out, one by one, they are different. Most of them are scared.”

She said she knows she can lessen the pain of others by showing how she confronted her own pain and fears.