Chris Wilding Recounts Losing His Anal Virginity to a South American Surgeon

Stern Show staffer says maneuvering was tricky at first but he eventually reached completion

December 10, 2019

Photo: The Howard Stern Show

Chris Wilding came into the Stern Show studio on Tuesday and revealed he’d recently lost his anal virginity to a South American surgeon. Howard and co-host Robin Quivers were shocked by the news, especially considering the staffer had long proclaimed to be a “top.”

Chris recounted the whole story for Howard and his listeners, saying it happened in New York City while the man was in town for a short layover before heading to Thailand. It was the second time they’d gotten together for a meal with a side of sexual adventure but the first time Chris had allowed him to take the road less traveled.

“Did you like it?” Howard asked.

“At its best, it felt like the best parts of taking a shit,” Chris said.

Chris described his South American suitor as a “beautiful guy” who’s bigger than him physically though not as well endowed. He said their latest encounter began with a “sexy dinner” and soon enough they were back at Chris’s place, “kissing and sucking and sixty-nining and all of it.”

“He kept trying to get back in that area,” Chris explained. “He does this thing all guys do. He goes, in a thick accent … ‘I want to do just the tip.’”

Chris gave in and presented himself doggystyle for the man, but anal entry proved trickier than expected. “It’s like trying to land an aircraft carrier,” he explained.

His beau’s arrow eventually hit the target and Chris described the physical experience for listeners. “I feel a bit of pressure. He sort of edges it in slightly and then, sure enough, there’s a pop and it’s all the way in,” he said, adding, “I have to tell you, it didn’t feel terrible.”

“Then I started manipulating myself as I’m getting fucked by this guy and I have to tell you—this really shocked me—I came,” Chris continued, explaining his surgically proficient suitor stayed the night and they had anal sex once more in the morning.

“Robin, now you have someone to talk to around here,” Howard joked, referring his co-host’s infamous tale about losing her own anal virginity back in the day.

Photo: The Howard Stern Show

Ronnie “the Limo Driver” Mund has previously been vocal about his own anal adventures, too, so Howard brought him in on Tuesday and asked if Chris’s experiences paralleled his own pegging adventures.

Ronnie congratulated Chris on his accomplishment but said their experiences seemed different, especially considering he doesn’t masturbate while getting pegged. He did have a few follow-up questions for Chris, however.

“Are you gonna take it in the ass from other guys or just this one guy?” Ronnie asked him.

“I may,” Chris said. “I’m not looking to have, you know, like a big loose asshole back there because those things don’t grow back like a vagina.”

At one point, staffer Shuli Egar chimed in with a question of his own, but Ronnie wasn’t having it. “Dude, you have no reason to be here … Do you take it in the ass?” he asked Shuli.

“No,” Shuli replied.

“Then get out,” Ronnie told him.

Regardless of what happens with other men, Chris’s tryst with the guy who took his anal virginity might not be over. “We’re talking about maybe meeting up again,” Chris told Howard. “He’s in South America so it’s tricky, but maybe meet up and maybe go to Paris or something.”