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Elliot Page details graphic failed attempts to have sex with a man at age 16

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Elliot Page has graphically detailed his failed attempts to have sex with a man aged 16 – as he battled with his sexuality years before coming out as gay.

The Oscar-nominated star, 36, who was once known as Ellen Page and came out as transgender in 2020, revealed he once dated a classmate called Kenneth and repeatedly attempted to lose his virginity to him – to no avail.

Writing in his new memoir Pageboy, Page said the pair – who met in grade 10 at Queen Elizabeth High School in Halifax, Nova Scotia – would ‘fool around upstairs’ and engage in ‘dry humping’ – which did not arouse Page.

He wrote: ‘Kenneth was sweet, sensitive and cute. A unique face with prominent cheekbones and electric eyes, his hair dark brown and floppy.

‘We’d fool around upstairs. I didn’t really like it but I didn’t mind it either

Very candid: Elliot Page has graphically detailed his failed attempts to have sex with a man aged 16 – as he battled with his sexuality years before coming out as gay (pictured 2022)

Teen years: The Oscar-nominated star, 36, who was once known as Ellen Page and came out as transgender in 2020 , revealed he once dated a classmate called Kenneth and repeatedly attempted to lose his virginity to him - to no avail (pictured 2004)

Teen years: The Oscar-nominated star, 36, who was once known as Ellen Page and came out as transgender in 2020 , revealed he once dated a classmate called Kenneth and repeatedly attempted to lose his virginity to him – to no avail (pictured 2004)

‘The kissing, meh. The dry humping, alright. I would pretend to orgasm. Not that Kenneth wasn’t or wouldn’t be fantastic in bed. I am certain he would be a selfless and generous lover.’

Going into further explicit detail, Page said when they tried to have sex, Kenneth was unable to enter him, adding: ‘That whole “wet” thing was not happening.

‘We’d try and then stop, try and then stop, try and then stop, and then we stopped trying. I was lucky it was with someone as lovely as him, it could have ended a different way.’

The star added that due to suffering a tear in his private parts during a rollerblade accident, he had this ‘idea that something had happened to my vagina – causing my body to refuse entry.

‘Everyone was talking about “doing it” and “hooking up” and “virginity”… and I didn’t get it. Was everyone also pretending?

‘I avoided sex with guys and suppressed my real, unrequited crushes. My brain could not comprehend that I simply wasn’t interested, that I just didn’t want to go through with it, which would be a completely appropriate feeling and response.’

Page would come out as a lesbian in 2014 – and would transition from female to male six years later.

Elsewhere in the book Page revealed he developed stress-induced shingles on the set of Inception in 2010 after feeling ‘out of place in a cast full of cis men.’

Sexuality battle: Writing in his new memoir Pageboy, Page said the pair - who met in grade 10 at Queen Elizabeth High School in Halifax, Nova Scotia - would 'fool around upstairs' and engage in 'dry humping' - which did not arouse Page (pictured 2006)

Sexuality battle: Writing in his new memoir Pageboy, Page said the pair – who met in grade 10 at Queen Elizabeth High School in Halifax, Nova Scotia – would ‘fool around upstairs’ and engage in ‘dry humping’ – which did not arouse Page (pictured 2006)

He wrote: ‘Shingles communicated the stress my body felt. It popped out of my spine while filming Inception when I was twenty-two.

‘Despite everyone being delightful to work with, I felt out of place. In a cast full of cis men, I did not understand the role I found myself in.

Elliot said that early on in filming he would joke that he’d be ‘recast with Keira Knightley.’

This comes after Page claimed he had sex with Juno co-star Olivia Thirlby ‘all the time’ while they filmed the hit 2007 movie – just days after revealing he had a secret romance with Kate Mara.

The star said he was instantly attracted to Thirlby, now 36, who played Juno’s best friend Leah in the film, as he recounted their fling in Pageboy.

He said: ‘I was taken aback the moment I saw Olivia Thirlby. She seemed so much older, capable, and centered.

‘Sexually open, far removed from where I was at the time. But the chemistry was palpable, it pulled me in.’

Page – who played pregnant teen Juno MacGuff in the film – recounted how they started ‘sucking face’ in a hotel room after Thirlby confessed she was ‘really attracted’ to him – to which Page reciprocated her feelings.

Fling: This comes after Page claimed he had sex with Juno co-star Olivia Thirlby 'all the time' while they filmed the hit 2007 movie - just days after revealing he had a secret romance with Kate Mara  (pictured)

Fling: This comes after Page claimed he had sex with Juno co-star Olivia Thirlby ‘all the time’ while they filmed the hit 2007 movie – just days after revealing he had a secret romance with Kate Mara  (pictured)

He wrote: ‘It was on. I had an all-encompassing desire for her, she made me want in a way that was new, hopeful.’

He added it was one of the first times someone would make him orgasm. 

Page said he and Thirlby began having sex ‘all the time’, writing: ‘Her hotel room, in our trailers at work, once in a tiny, private room in a restaurant … We thought we were being subtle. Being intimate with Olivia helped my shame dissipate. I didn’t see a glint of it in her eyes and I wanted that — done feeling wretched about who I am.’

Around the time Page and Thirlby filmed Juno, the pair were slated to star as the title characters in Jack & Diane – playing two young women who fall in love -but both dropped out before production, and the cast was replaced numerous times over. 

Thirlby publicly came out as bisexual in 2011 – she has been married to Jacques Pienaar since 2014. 

DailyMail.com has contacted representatives for Thirlby for comment. 

This comes after Elliot revealed he had a secret relationship with Kate Mara after he came out as gay in 2014 – and while she was dating Max Minghella.

The Oscar-nominated Juno star, 36, who was once known as Ellen Page and came out as transgender in 2020, details in his memoir Pageboy how he and Kate, 40, struck up a romance as he filmed X-Men: Days of Future Past and that Kate was ‘in love with two people.’

Kate and Max went their separate ways in 2014 after four years of dating. She is now married to actor Jamie Bell, with whom she shares two children.

In an excerpt from his memoir, obtained by People, Page writes: ‘The first person I fell for after my heart was broken was Kate Mara. She had a boyfriend at the time, the lovely and talented Max Minghella.’

Tea spilled: He wrote: 'It was on. I had an all-encompassing desire for her, she made me want in a way that was new, hopeful.' He added it was one of the first times someone would make him orgasm' (pictured together in 2007)

Tea spilled: He wrote: ‘It was on. I had an all-encompassing desire for her, she made me want in a way that was new, hopeful.’ He added it was one of the first times someone would make him orgasm’ (pictured together in 2007)

Racy: Page recounted how they started 'sucking face' in a hotel room after Thirlby confessed she was 'really attracted' to him - to which Page reciprocated her feelings (pictured in Juno with Allison Janney)

Racy: Page recounted how they started ‘sucking face’ in a hotel room after Thirlby confessed she was ‘really attracted’ to him – to which Page reciprocated her feelings (pictured in Juno with Allison Janney)

Coming out: Olivia came out as bisexual publicly in 2011 - she has been married to Jacques Pienaar since 2014 (pictured 2019)

Coming out: Olivia came out as bisexual publicly in 2011 – she has been married to Jacques Pienaar since 2014 (pictured 2019)

‘This was right after I’d come out as gay [in 2014] and it was a time of exploration and also heartbreak. I think my relationship, or whatever you want to call it with Kate, very much encapsulates a certain dynamic that I consistently found myself in, which was falling for people that — I think a lot of us do this — who aren’t fully available. 

‘And the sort of safety in that and the highs and the lows and the serotonin bump, and then it goes away. And I think that is definitely a pattern in my life.”

‘I think the love and care that we have for each other is it’s very own special thing. Separate from the intimacy that I write about.’

Elliot said Max was supportive of Kate exploring their relationship -which was kept a secret from the world and says Kate told him: ‘I never thought I could be in love with two people and now I know I can.’ 

The pair played a couple in movie My Days of Mercy which premiered in 2017 and was released in 2019 – this was made after their romance. 

Page added that Kate has read the book and will appear at a book event in LA in June to promote it. 

Elliot publicly came out as a transgender man in December 2020 but revealed he began ‘feeling like a boy’ from the age of nine.

In an extract shared by People, Elliot recalled being in a gay bar just a few months before the premiere of his breakout 2008 movie Juno. 

At the bar he met a woman named Paula, who unwittingly helped him address the feelings of ‘shame’ he had. 

Heartbreak: This comes after Elliot revealed he had a secret relationship with Kate Mara after he came out as gay in 2014 - and while she was dating Max Minghella (pictured 2017)

Heartbreak: This comes after Elliot revealed he had a secret relationship with Kate Mara after he came out as gay in 2014 – and while she was dating Max Minghella (pictured 2017)

Former couple: Kate and Max went their separate ways in 2014 after four years of dating (pictured 2014)

Former couple: Kate and Max went their separate ways in 2014 after four years of dating (pictured 2014)

Ex; Elliot said Max was supportive of Kate exploring their relationship -which was kept a secret from the world and says Kate told him: 'I never thought I could be in love with two people and now I know I can' (pictured 2014)

Ex; Elliot said Max was supportive of Kate exploring their relationship -which was kept a secret from the world and says Kate told him: ‘I never thought I could be in love with two people and now I know I can’ (pictured 2014)

Moved on: Kate is now married to actor Jamie Bell and the pair share two children (pictured January 2023)

Moved on: Kate is now married to actor Jamie Bell and the pair share two children (pictured January 2023)

 He wrote: ‘Dancing, sweat dripping down my back, down my chest. I watched Paula’s hair twist and bounce as she moved effortlessly, chaotic but controlled, sensual and strong. 

‘I would catch her looking at me, or was it the other way around? We wanted to be caught. Deer in the headlights. Startled, but not breaking.’

Having asked if he could kiss her, he continued: ‘And then I did. In a queer bar. In front of everyone around us. I was coming to understand what all those poems were about, what all the fuss was.

‘Everything was cold before, motionless, emotionless. Any woman I had loved hadn’t loved me back, and the one who maybe had, loved me the wrong way. 

‘But here I was, on a dance floor with a woman who wanted to kiss me and the antagonizing, cruel voice that flooded my head whenever I felt desire was silent.’

Elliot also looked at how the bar helped him address his feelings of shame. 

He penned: ‘Shame had been drilled into my bones since I was my tiniest self, and I struggled to rid my body of that old toxic and erosive marrow.

‘But there was a joy in the room, it lifted me, forced a reaction in the jaw, an uncontrolled, steady smile.’

Elliot was paid ‘north of $3M’ to write his 288-page tell-all, which Flatiron Books will publish on June 6.

The two-time Emmy-nominated producer came out as a lesbian in 2014 during a speech at the Human Rights Campaign’s ‘Time to Thrive’ conference in Las Vegas.

Elliot kicks off his nine-date international book tour on June 6 at The Town Hall in Midtown Manhattan, and future dates will be announced soon.

It’s unclear if Elliot is still dating non-binary comedian Mae Martin after the pair got matching tattoos and suited up for the 11th Annual LACMA Art + Film Gala on November 5.

Elliot’s divorce from Canadian dancer Emma Portner was finalized in 2021 after two years of marriage.

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