Stephen, 45, is a happily married father of two. His alter ego, Stephanie, loves to dress as a woman. His wife doesn’t mind but the couple do wonder how and when to tell their daughters about their father’s secret cross-dressing

How do we tell the children that their dad is a transvestite?

With his conservatively cropped hair, rimless designer glasses and unassuming sprinkling of stubble, the 45-year-old man who is thoughtfully sipping a glass of red wine bears little resemblance to the immaculately made-up, raven-wigged confection pouting at the camera from his Facebook profile picture.

Click on Stephen’s photo albums and the ambiguity amplifies.

Alongside typical family snapshots of him with his daughters, Samantha, 10, and Sylvie, seven, sit dozens of candid photographs of his alter ego Stephanie, dazzling in an ankle-length silver gown, sipping cocktails in the Shard in a ruched cobalt blouson and even posing in a matching little black dress with his French wife, Carla.

It’s a contradictory dynamic and one that Home Counties-born Stephen, managing director of his own London web design agency, is endeavouring to assimilate into orthodox family life. “There are certainly paradoxes,” acknowledges Stephen who, at 18-months into a course of psychotherapy, is striving to pinpoint the roots of his transvestism. “At this point I’m better at describing what happened rather than why it happened,” he admits.

Stephen’s cross-dressing began when he was a year or two older than his eldest daughter, Samantha.

“I started buying women’s knickers, bras and stockings as I liked the feeling and texture,” he says. “I wore them in bed and at that point my parents had no idea. I liked the secrecy. It was like, ‘Look at me, I know something you don’t.’

“I hid them under the bed and then periodically I’d get massive waves of guilt and revulsion and throw them all away. I’d feel ashamed that I was really weird and shouldn’t be doing it.”

Stephen’s liberal parents – his mother is a psychiatrist, his father a mathematician – remained oblivious to their son’s clandestine habit.

“I felt isolated. I was worried I’d be rejected if people knew. So I never told anyone, which had a secondary impact in that I assumed that although I appeared to have friends, in reality if they knew about me they wouldn’t like me. And that’s a vicious circle because dressing up made me feel a lot better. It made me feel special and interesting. So I’d do it more and then I’d feel more isolated.”

Aged 17, studying for A-levels, Stephen finally unburdened himself to his friends, who, rather than ostracising him, embraced his revelation. Teenage girlfriends were largely accepting – “Some of them were like, ‘Ooh, that’s interesting,’ while others said, ‘You’re never doing it in front of me.’”

Emboldened by his peers’ reaction, the frequency and ostentatiousness of his cross-dressing escalated and when he was 24, Stephen plucked up the courage to tell his mother.

Again his fears were unfounded and, three years after his first fully cross-dressed public outing when he was 29, Stephen met his wife, Carla. “I was open about my cross-dressing from day one,” he says. In fact, he went to his second date with Carla in full drag.

“I thought, if she doesn’t like it then I’ve saved myself a lot of effort. But it went down very well. I think she found it quite exciting. She’s from a small village in France, from a traditional Catholic family and she’d never come across anyone so interestingly unique.”

Carla, whose parents and siblings still live in France, confirms that she was initially intrigued. “At that point, I didn’t really look at him as someone I was going to end up with so I didn’t bat an eyelid,” she says, “I just thought it was all a bit of fun.”

After their wedding – a photograph of Stephen in Carla’s wedding dress hangs proudly in their bedroom – the implications of his cross-dressing slowly leaked into family life.

But telling their children has been the most complex challenge for the couple, one they are still unsure how or when to fully address. “I never thought about the impact it might have on the children until we had them and actually not even until they were a bit bigger,” says Carla.

I want to tell them when they won’t just go to school and blurt out, 'My daddy is a cross dresser'

It’s a view echoed by Stephen, who as well as regularly waxing his legs and chest pays a professional makeup artist £70 three or four times a year to transform him into a persona he says makes him feel “alive and glamorous”.

“We never really discussed the impact on the kids and it only came up when they were old enough to walk about and look at things like the wigs in our bedroom, but I have said things to them occasionally,” says Stephen, who owns 15 pairs of women’s shoes and a lavish lingerie collection.

“When we were reading David Walliams’ book, The Boy in the Dress, we started talking about gender identity and I said to my youngest, who is a bit of a tomboy, ‘Dresses are really glamorous and interesting and nice and you can wear them,’ and she said, ‘I don’t like them,’ and I said, ‘I feel really jealous of you because I’d like to look that nice and lovely too.’

“When we go swimming we all get changed together in the same cubicle and quite often I’m wearing women’s underwear, so the girls do notice.

“Sylvie says, ‘Most boys wear big long pants and you’re not,’ and I say, ‘I don’t like long pants so I don’t wear them,’ and they are, like, ‘OK’.

“I’ve always told them that they should ignore what gender they are for the purposes of absolutely everything. They will probably face sexual discrimination at some point so it’s good to get into that mindset of being able to do anything, whatever your gender.”

Laudably progressive as Stephen’s sentiments undoubtedly are, Carla’s discomfort with her husband’s Facebook transparency remains. “I would love him to change his profile picture,” she says.

“Some of his Facebook friends are parents at our children’s school. I don’t mind them knowing as they are enlightened adults but I don’t want the children to be bullied at school because their dad dresses as a woman.

“The children must have seen him with nail varnish on and the remains of his makeup after he’s been out but they have never said anything.

“It’s normal for them so they just accept it and he’s quite good at acting consistently with the girls, whether he’s been cross-dressing or not

“At some point,” concedes Stephen, “they will realise that their dad likes wearing nail varnish and that’s just not normal dad behaviour is it?”

So how will the couple tackle the issue? “I don’t want to keep it a secret,” says Carla. “I want to tell them when they won’t just go to school and blurt out, ‘My daddy is a cross-dresser.’ I want them to think rationally, ‘who can I tell about this? Who are the friends who would be able to deal with this?’ and not go round telling everyone and getting called names.”

“I don’t think we have a specific plan,” concludes Stephen. “Our vague idea is just to get them to be accepting and tolerant of differences.

“In a worst-case scenario they might turn out being scarred for life by not having a proper father they could look up to. But I don’t think that’s the case and, with children, pretty much everything you do is a compromise. There’s no manual for them. They are all different. There’s never any best way to parent them. There are a lot of options and paths and alternatives and you just do the best you can, given the circumstances, so this is the best we can do and I hope it’ll be enough.”

Names have been changed