Caitlyn Jenner’s love life – surgery, awkward sex blunder and being Kris’ biggest regret

She first soared to fame when she won the gold medal and broke the world record in the decathlon in the 1976 Montreal Olympic Games.

Since then, Caitlyn Jenner has gone from strength to strength as an athlete and a businesswoman. But arguably, the former athlete rose to new heights when she married business mogul Kris Jenner and welcomed their two daughters Kylie and Kendal years later.

But it’s fair to say her world turned upside down when the TV personality came out as a transgender woman in April 2015. The brunette beauty is now out and proud but her complicated gender and sexuality journey has made for some difficult relationships with herself and others.

READ MORE:Khloe Kardashian strips topless in racy snap as mum says ‘everyone fancies’ her

READ MORE: Kris Jenner floored as Rob Kardashian makes ‘w***e’ comment in rare TV appearance

As Caitlyn celebrates her 74th birthday with a bang, Daily Star has taken a deep dive inside her love life and how that has changed since she completed her transition Let’s take a look…

Supportive wives

Before her transition, Caitlyn – then known as Bruce – had previously slept with just five women in her life, three of whom were her ex-wives. In her memoir, The Secrets of My Life, Jenner admits that she struggled with her identity from an early age and is still struggling with labels to this day.

In the book, she explains that she’s not interested in talking about having sex and doesn’t have a high sexual appetite. She confessed: “I don’t have the appetite for it, which is why the public’s obsession over my sex life now is annoying to me.

“It harkens back to this endless misconception that men and women transition because of their sexual preference and desires. Who the hell cares? Why must labels be attached to everything? My preference has not changed now that I have transitioned.”

Jenner went on to speak fondly of her three ex-wives including Chrystie Jenner and Linda Thompson as well as Kris Jenner whom she was married to for 22 years. Throughout the book she claims that on multiple occasions she had told Kris about her gender dysphoria and had difficulty with gender identity.

She went on to claim that she told Kim before they ever had sex, which notably differs from Kris’ point of view. Despite Kris’ disappointment at the revelation, Caitlyn thanks her for her support throughout her transition and everything they went through during their relationship.

In the latest episode of The Kardashians, Kris admitted cheating on Robert Kardashian with Caitlyn was her “biggest regret”, saying: “I don’t know because he was such a great husband and such a great dad, and I think that I fell into a situation where I thought that the grass was greener somewhere else, and I made a huge mistake,” Kris said. “That’s my life’s biggest regret.”

Awkward sex blunder

Arguably, the sportswoman’s most famous romp in the sack was with her ex-wife Kris who spilt the beans on the Ellen DeGeneres Show back in 2021. During her time on the show, she confessed to the talk show host that her daughter Khloe Kardashian and her friend accidentally caught the pair in the act.

She recalled how her daughter and her friend, who was 10-years-old at the time, were finishing a game of hide-and-seek when they decided to hide under her parents’ bed. But things soon turned awkward when Kris and Caitlyn got wild under the covers, completely unaware of their presence.

Kris admitted to Ellen that the kids have “stayed there for a really long time” before she and Caitlyn “came into the bed and went to sleep” during which they had “a little bit of hanky panky going on.”

The TV star chuckled: “So that was traumatising. Khloe probably has PTSD over that one.” DeGeneres went on to ask when Caitlyn and Kris realised that the two friends were under the bed.

She replied: “They were so scared – they stayed there for hours – and in the middle of the night when they were sure we were both asleep, they snuck out and we caught them sneaking out.” Khloe shared her own account of the embarrassing moment back in 2016 during an episode of her talk show Kocktails with Khloe.

The mum-of-two told viewers: “I was playing hide-and-go-see when I was younger and I fell asleep… under my mom and [Caitlyn’s] bed. And I woke up to the bed shaking and I was too scared to leave so I had to wait for the whole thing.”

The Good American founder added: “My mom feels bad about it still. We talk about it all the time. I’m like, ‘You guys, I’m scarred for life. That’s why I am the way that I am’.”

But their sex wasn’t quite as incredible as some may have thought, with Caitlyn later revealing that she never felt “entirely comfortable” getting down and dirty with Kris. She told The Sunday Times: “[Sex meant] giving, and while I believe I am better now. I have never been good at it.”

Romance post-surgery

Since she completed her transition in 2017, the star has been romantically linked to two people. The news came as a surprise to fans after she once ruled out a sexual future with a woman once and for all in her memoir.

She wrote: “A future female companion? I think about that. A future female sexual companion? Not happening, at least for now, and perhaps not ever. A future male sexual companion? I have never had the inclination. But maybe that attitude might possibly change if I have the Final Surgery.”

Caitlyn was first linked to transgender actress Candis Cayne, with the pair reportedly snogging at a salon, which Caitlyn denied, before she went under the knife for her “final surgery” to remove her penis in 2017. The pair have since gone their separate ways.

Caitlyn said about her surgery: “The surgery was a success, and I feel not only wonderful but liberated. So why even consider it? Because it’s just a penis. It has no special gifts or use for me other than what I have said before, the ability to take a whiz in the woods. I just want to have all the right parts.”

The second star she was linked to was a transgender student named Sophie Hutchins. Fans of the former Olympian were convinced that the pair were engaged after they became inseparable in 2017.

Sophie met Caitlyn through their hairstylist and they became friends, and Sophia even took over managing Caitlyn from her ex-wife Kris Jenner following their divorce. She later moved In with Caitlyn and became her full-time manager but in 2020, the star made it clear that she wanted to move out.

Speaking on the Juicy Scoop podcast with Heather McDonald, the 24-year-old claims the athlete deliberately walked in on her having sex. She told the host that Caitlyn was “barging” into her room when she had guests over which became a frequent occurrence while they lived together.

She explained: “[Caitlyn] kind of saw a lot of things happening and so it’s kind of like living with your parents. I’m like, ‘Oh, this might be a turning point where I need to move out’.” Caitlyn has been pictured numerous times on the red carpet with Sophia who became her plus one to her star-studded events – including family parties.

Sophie even jetted to Australia to meet with Caitlyn after her exit from the I’m A Celebrity jungle, but they never made the nature of their relationship clear until years later. On the podcast, Sophia clarified: “It was never romantic. It was never sexual. It was very much friends.”

Single life

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Earlier this month, Caitlyn insisted that she’s “very single” these days and has no intention to find a partner any time soon – or ever. In a new interview with The Times, the star told the outlet that she doesn’t see herself having another relationship in her lifetime.

She explained: “I’m fine. I’m not even close to looking for a relationship. I’ll never have a relationship in the future. I just don’t see that in my life. I am not looking for that.”

Elsewhere in her discussion with the publication, Jenner spoke fondly of her past relationship with her ex-wife Kris Jenner, who met during a blind date back in 1990. The Olympian claimed it was “love at first sight”, adding: “We hit it off right at the beginning, and we were married after five and a half months.

“I was infatuated with her because she was very different from me. But yes, I’d have to say it was love at first sight.” Fans are still holding out hope that the athlete will find love again one day and will share the news with her loyal supporters online.

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Source: Celebrities - dailystar.co.uk