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Sometimes it’s dark, it gets late, and you can’t spot an adam’s apple the way you would during daylight hours.

Being caught in a compromising position with a transgendered person can be hard but at least these celebs didn’t have to endure their embarrassment alone.

Check out some of the most persistent rumored celebrity encounters with the trans-kind when you continue!

Eddie Murphy

In May 1997, Murphy was stopped by police with a transvestite prostitute in his car shortly before the release of Holy Man. He famously defended himself by claiming: “I was just giving her a ride home.” Nearly 15 years later, the incident still hasn’t been forgotten.

Teddy Pendergrass

Late great R&B singer Teddy Pendergrass was paralyzed from the waist down in a terrible car accident in 1982. While all the details have never been fully revealed, it’s been speculated that he was distracted by a passenger named Tenika Watson. Watson, a 31-year-old transsexual model, nightclub singer and rumored prostitute has been blamed by some for his injuries, but Pendergrass once said: “What matters is what happens afterward.”

Tenika Watson, who was born John Watson, had already undergone a sex-change operation by then and was working part-time as a nude model. She described her relationship with Pendergrass as “flirty,” and said they had run into each other a couple times at a nightspot called Fantasy Club. Watson may have been the one who inspired Eddie Murphy because she always claimed Pendergrass was giving her a “ride home—that was it.”

Ma$e

The good Pastor Betha was caught trolling for trannies back in 2007. He was allegedly so busy looking for some late night action that he hit a woman’s Range Rover while cruising Atlanta’s Spring Street area just after midnight on a Friday.

According to reports, officials arrived on the scene shortly after the incident occurred, and Mase refused to co-operate until authorities threatened to impound his car.

The unnamed victim later appeared on local radio station WHTA and told the Ryan Cameron Morning Show,

“(The transgender prostitues) came running up to the car saying, ‘Girl, girl, we seen what happened, we seen everything!’

“It’s like, five or six of them because they working, so they run up to the car saying, ‘Girl, are you OK? He’s been circling around here like four times already trying to pick one of these queens up.'”

Chingy

Chingy has tried to deny Sidney Starr’s claims that “she” hit that back in the day, but it doesn’t help that good ol Sid has photographic evidence.

“Of course he’s not gonna come out with everything and I understand that,” Sidney Starr told radio host Kendra G. “I feel he’s ashamed, that’s all it is. He’s ashamed to come forth about it. And he shouldn’t be…I don’t think it would be bad [for him to admit having sex with me.] … Why should you be ashamed of a woman just because she’s transgendered? This is just my opinion and I know the hip-hop industry is very critical. Honestly the hip-hop industry is very homophobic, and it’s not gonna stop, but I think it should. First of all, it’s not like we did something to make it seem like I was trying to put him on blast because I could have did it two years ago. Honestly. I don’t think there’s anything wrong with it because I’m a woman now…”

LL Cool J

The crossdressing version of Karrine Steffans let it all hang out this year by revealing her celebrity encounters with LL Cool J and Mr. Cee:

In her newly released memoir, ‘I Rise – The Transformation of Toni Newman’ Toni writes:

“LL Cool J was a one time encounter and very enjoyable.”

“Mister Cee picked me up and many others for the sole purpose of receiving oral sex. Mister Cee was obsessive about receiving good head and he was very verbal and very generous if you performed up to his expectations.”

“I never had an encounter with Eddie Murphy, but he was visiting 14th street late at night. I know at least five transgenders who did have sex with Eddie Murphy. He was interested in the girl with the biggest male genitalia.”


Mr. Cee

When Biggie’s old DJ Mr. Cee plead guilty to public lewdness and exposure earlier this year the public speculated hip-hop homophobia might be coming to a stop, but Cee continued to cling to the closet, despite revelations that the sex act he was caught in with Lawrence Campbell aka “Brooke Lynne Pinklady” was not his first experience with the transkind…

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Gavin Rossdale

Before he was married to Gwen Stefani, Gavin Rossdale’s boo was a transgender individual who went by the name of “Marilyn.” He’s since tried to downplay the relationship as experimentation, but openly admitted his dealings in an interview with Details Magazine last year.

Details: Last year, the cross-dressing pop singer Marilyn revealed that he was romantically involved with you in your teens—an assertion Boy George first made in 1995. Why haven’t you talked about those claims?

Gavin Rossdale: I think at the outset there was a sort of fear—that was right at the beginning of Bush, and I didn’t want it to be part of it. It felt like a cheap shot, so I was like, “I’m not getting involved.” I’ve never wanted to appear closed about it. It’s not something I’ve talked about really because it’s always been in the glare of a tabloid world. It’s just one of those things: Move on. When you’re 17, Jesus Christ. I don’t think there’s anything strange about any form of—you’re learning about life. It’s a part of growing up. That’s it. No more, no less.

Details: So it was just a one-time experimentation?
Gavin Rossdale: Yeah. That was it. You have to know what you like, and I know what I like.

Marilyn has gone on record saying “her” relationship with Gavin actually lasted five years, but felt like 40.

Matt Lauer

Last year rumors emerged that Matt Lauer cheated on his wife with a “woman” named Alexis Houston who turned out to be formerly a man named Stuart Wellington. To further complicate matters, Alexis, who is also a singer, has faced a lawsuit from Whitney Houston for trying to pass herself off as a cousin. Lauer was alleged to have carried on an affair with Houston for two years — all of which were post-operative, but both he and Alexis denied the rumors.

Ronaldo
The soccer world was dumbfounded in 2008 when three tranny hoes came forward saying that the Brazilian star had picked them up and had sex and done drugs with them in a hotel room. Two of them eventually admitted they lied about Ronaldo using drugs and having sex with them during the motel encounter, but
they claimed they did so because Ronaldo did not want to pay them after finding out they were men.

When first questioned by police after the April 28 encounter with Ronaldo, the prostitutes said the player had sex with them and asked one of them to buy drugs for him.

Ronaldo vehemently denied the accusations and said one of the prostitutes tried to extort money from him to keep the story to the media. He said he offered to pay the prostitutes even after finding out the were men, but one of them demanded more than offered.

In a nationally televised interview Ronaldo said he was sorry, embarrassed and ashamed for his “stupid act.”

Bow Wow

In 2009 friends of a post-op male to female transgender woman named Nadia sent an item to gossip blogs claiming:

“Nadia and Bow Wow hooked up on a one night stand but I still don’t know to this day if Bow Wow knows he fawked a tranny or not because she looks and acts like a natural born female. I also heard her “milkshake” brings all the straight and bisexual boys to the yard.”

Nadia has also been tied to Diddy!!!

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