10 Celebs Caught In The Act With A Transgendered Lover

Different people have different preferences when it comes to intimacy and relationships. Sounds healthy enough, right? But what if your spouse is caught sneaking around with a transgender woman? What if you weren't aware that your significant other has some sexual tendencies that are unconventional to say the least?

This information can be jarring, and has been known to cause serious relationship problems. Celebrities who are caught at some point or another with a transgender individual may have also questioned their own sexuality after the incident. While there's nothing wrong with finding out who you are and what you like, it's not particularly wise to make these discoveries at the expense of someone else's feelings or your career. Even though many of these celebs have gone on to create great work, in the back of the minds of some fans, some of these famous individuals will always be known as "the guy who was caught with a transgender woman". That isn't exactly a career boost.

Sure, these stories are entertaining. But it's also easy to see how news like this could turn your entire life around. Here are 10 celebrities who had an encounter with a transgendered person, and the aftermath of their decisions.


10 Luke Worrall

Luke Worrall is a model and DJ--and the ex-fiance of former Fashion Police host and clothing designer, Kelly Osbourne. The two were in a seemingly happy relationship, until Osbourne kept getting word from her friends that her fiance was being unfaithful. It turns out they were right. Worrall was allegedly cheating with Elle Schneider, a transsexual who was waiting for gender reassignment surgery. Kelly was of course, furious about the situation. In an interview with Glamour magazine, she stated that it was difficult for her to accept the fact that her significant other was being unfaithful. But it was even harder to wrap her head around the fact that he chose to cheat with a transgender woman.

9 Gavin Rossdale


Gavin Rossdale is known for being the lead singer for Bush and for being No Doubt’s front woman, Gwen Stefani's husband. But years before the two became an item, Marilyn, a transgendered British pop star, claims that he had an affair with Rossdale. Gavin admitted to this, stating that the affair happened before he was 17, and that he was experimenting with his sexuality. Rossdale stated that his affair with Marilyn was just "one of those things" and that you just "move on" because "it's a part of growing up." This is proven to be true for Rossdale, who now has three sons with Stefani.

8 Chingy

A transsexual woman named Sidney Starr claimed to have had a one night stand with St. Louis rapper, Chingy. Since the rapper hasn't had a hit in years, perhaps Starr felt that he should come forward about their affair so that it could help his career and get him back in the public eye. She states that their intimate encounter is nothing for Chingy to be ashamed of, and that it wouldn't be a bad thing for him to speak about their one-night stand. However, Chingy denies ever having slept with Sidney Starr. Later, Starr recanted her story about having sex with Chingy. She has also stated that she slept with rappers Lil Wayne and Soulja Boy, but has recanted these stories as well.

7 Mase

Mase, who is known for his tenure on Bad Boy Records in the 1990s, left hip hop for a while to become a pastor, and started rapping again from time to time. Then in 2007, he hit a woman's Range Rover when he was in a sketchy part of Atlanta looking for some action with transgender prostitutes. The victim was unnamed, but later went on an Atlanta radio station to say that prostitutes knew that Mase was around, circling the area. It's unclear what effects this incident has had when it comes to the rapper's marriage and church following. But it's safe to say that he did face some challenges after the interview.

6 Mister Cee

Mister Cee is a former hip hop DJ that was caught on video soliciting sex from a transvestite. In an interview with GQ Magazine, Mister stated that while he didn't mean to offend transgender women, he only solicited them for one thing, oral sex. Toni Newman also claims to have had sexual relations with Mister Cee, and confirms his preferences. She states that Mister Cee picked her up, along with others, simply for the purpose of receiving oral sex. Aside from his interesting sexual activity, Mister Cee is perhaps best known for being rapper Big Daddy Kane's DJ, and for being an associate executive producer on Ready to Die, which was the Notorious B.I.G.'s debut album.

5 LL Cool J


One of hip hop’s original pretty boys, who always had the ladies swooning, is said to have had a brief encounter with Toni Newman, a transgender woman. In Newman's book, I Rise, The Transformation of Toni Newman, she states that she and LL Cool J had a one-night stand that was "very enjoyable." The rapper's rep denies these allegations and refer to them as "pure comedy." This likely comes as good news to LL Cool J's wife, Simone. The couple have been together for over 20 years. In addition to LL Cool J's successful rap career, he's managed to make a name for himself in acting and hosting as well, and has even hosted the Grammys.

4 Hank Baskett

Basketball player Hank Baskett has been in hot water with his ex-playmate wife Kendra Wilkinson, for his affair with a transsexual, and it may have happened on more than one occasion. Kendra has asserted that she had to find out information about her husband's trysts in bits and pieces, often at the same time that the general public got the details. The couple's reality show on E! Entertainment Television also explored Baskett's infidelity, and the two even appeared on Oxygen's Marriage Boot Camp, in an attempt to work on their marriage and rebuild trust. Baskett and Wilkinson have two children together, and have decided to work on reconciling.


3 Bow Wow


Bow Wow was a kid rapper who was likely used to being welcomed by screaming female fans every time he made a public appearance. The former 106 and Park host has also allegedly hooked up with a woman who used to be a man in his later years. Nadia Milan, a transgender woman, is said to have had a one-night stand with the rapper, who is now in his 20s. Apparently, Milan used to be a man and had a surgery to change her gender. Friends of Bow Wow assert that they're not sure whether the rapper knew that Milan had once been a man. Bow Wow is currently engaged to Love and Hip Hop star Erica Mena, who has identified herself as bisexual.

2 Wiz Khalifa

The popular rapper, who recently ended his relationship with model Amber Rose, was allegedly caught sleeping with Amiyah Scott, who is a transgender. Of course, there were rumors swirling around about who was at fault for the breakup, but the news of Wiz's connection to a transgender woman undoubtedly makes for even juicier gossip. Peter Rosenburg, a radio DJ for Hot 97 in New York City, is a family friend of Amber Rose. Rosenburg stated that Amber walked in on her husband having sex with Scott. Recently, there has also been talk about Amber Rose wanting Wiz Khalifa back, and that the two may be attempting to reconcile their relationship.

1 Justin Bieber


The pop superstar supposedly spent some intimate time with a transexual woman by the name of Vanity, who is about 20 years older than him. The two were spotted at a party in Malibu. Voodoo, an adult entertainment star, stated on a radio show in Toronto that he saw Justin Bieber being led away at the Malibu party by a woman that he later realized was Vanity, who is also an adult entertainment star. This isn't the first time Justin Bieber has had an alleged connection to a transsexual. In 2013, a woman from Brazil who claims to have had sex with Bieber denied reports that she was transsexual.



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