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Kyle Sandilands LOVED dressing up as a woman

He’s known for pushing boundaries as a shock jock for KIIS FM’s Kyle And Jackie O show, admitting on numerous occasions that he’d gone ‘the whole hog’ with a transsexual in the past. 

And on Tuesday, Kyle Sandiland’s model girlfriend Imogen Anthony, 26, joked she was ‘worried’ about what he liked.

The 46-year-old dressed up as a bearded lady for Halloween, which prompted Imogen to question the radio star.

 

‘He liked it too much, I’m starting to get worried’: Imogen Anthony reveals boyfriend Kyle Sandilands LOVED dressing up as a woman… after shock jock confessed he enjoyed tryst with transvestite

‘He liked it too much that I’m starting to get worried,’ the Australian glamour model and clothing designer joked.

‘In fact my mum and I have this theory that (straight) men obviously fight the thought of dressing up as a woman, but once they are dressed up, they actually love it…’ Imogen suggested.

Kyle got in touch with his feminine side for the Halloween-themed party by sporting a long pink frock imprinted with butterflies over his stocky stature. 

Working it! Kyle got in touch with his feminine side for the Halloween-themed party by sporting a long pink frock imprinted with butterflies over his stocky stature

Working it! Kyle got in touch with his feminine side for the Halloween-themed party by sporting a long pink frock imprinted with butterflies over his stocky stature

Going all out: Kyle also had dyed his beard orange to match his long-haired wig that fell effortlessly over his shoulders in curls

Going all out: Kyle also had dyed his beard orange to match his long-haired wig that fell effortlessly over his shoulders in curls

Kyle also had dyed his beard orange to match his long-haired wig that fell effortlessly over his shoulders in curls.

While he appeared uncomfortable in the outfit to begin with, he was later seen twirling towards the camera singing the Shania Twain 1997 classic ‘Man, I Feel Like A Woman’, leaving Imogen and the crowd in stitches. 

Imogen and Kyle have a 20-year age gap between them and have been together since 2012.

The busty blonde met Kyle at his 40th birthday shortly after his split from former wife Tamara Jaber, and their relationship has gone from strength-to-strength since. 

Couple: Imogen Anthony (Pictured) and Kyle have a 20-year age gap between them and have been together since 2012

Couple: Imogen Anthony (Pictured) and Kyle have a 20-year age gap between them and have been together since 2012

The busty blonde met Kyle at his 40th birthday shortly after his split from former wife Tamara Jaber, and their relationship has gone from strength-to-strength since

The busty blonde met Kyle at his 40th birthday shortly after his split from former wife Tamara Jaber, and their relationship has gone from strength-to-strength since

Kyle is not shy of speaking or boasting about his relationship with the scantily-clad model on-and-off air.

Some of his shock, and crude, admissions have included helping his girlfriend with her feminine hygiene products, ‘thrashing’ her in the bedroom and admitting to having sex daily.

He also recently overshared with listeners of the Kyle And Jackie O show, when he revealed: ‘I sometimes go through the back door.’ 

'He can't help himself! Every opportunity, he likes to mention it': Earlier this year, co-host Jackie 'O' Henderson confronted Kyle over his apparent fixation with the tryst

‘He can’t help himself! Every opportunity, he likes to mention it’: Earlier this year, co-host Jackie ‘O’ Henderson confronted Kyle over his apparent fixation with the tryst

Kyle has also made no secret of the fact he once enjoyed a night of passion with a transsexual.

In fact, he mentions it often on his top-rating KIIS FM breakfast radio show, even surprising A-list celebrities with the details in interviews.

Earlier this year, co-host Jackie ‘O’ Henderson confronted Kyle over his apparent fixation with the tryst, saying: ‘He can’t help himself! Every opportunity, he likes to mention it’.

When mentioning the tryst, has has admitted to going ‘the whole hog’ and suggested he had no regrets about the affair either, saying: ‘Don’t forget… it was the year 2000 and all bets were off. The Olympics were on!’

'I'm not attracted to blokes, just the one trannie': Kyle has clearly stated in the past that he prefers the company of women

‘I’m not attracted to blokes, just the one trannie’: Kyle has clearly stated in the past that he prefers the company of women

He also spoke about the occasion to Waleed Aly in March.

‘Let me tell you, man to man. By the time you’re halfway through it and realise hang on, this is a bloke, you don’t want to hurt her feelings, you just go for it,’ Kyle said to The Project host.

Kyle first divulged his story during a show two years ago. He was mid-conversation with a ring-in guest named Amanda and abruptly announced, ‘I’ve gone the full deal with a transsexual, bet you didn’t know that?’

‘I’m not attracted to blokes, just the one trannie,’ he continued. ‘I wasn’t even attracted to it, I just wanted it.’

'I sometimes go through the back door': Kyle is not shy of speaking or boasting about his relationship with the scantily-clad model on-and-off air. Some of his shock, and crude, admissions have included helping his girlfriend with her feminine hygiene products, 'thrashing' her in the bedroom and admitting to having sex daily, sometimes through 'the back door'

‘I sometimes go through the back door’: Kyle is not shy of speaking or boasting about his relationship with the scantily-clad model on-and-off air. Some of his shock, and crude, admissions have included helping his girlfriend with her feminine hygiene products, ‘thrashing’ her in the bedroom and admitting to having sex daily, sometimes through ‘the back door’

 

Read more at DailyMail.co.uk


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