Former teacher who became a high-end escort and Diddy ‘freak-off’ regular reveals his biggest regret

Sharay Hayes, 53, is speaking out about the emotional toll of testifying in Sean “Diddy” Combs’s 2025 racketeering trial and the decades of secrecy that preceded it.

The former New York City kindergarten teacher turned high-end male escort revealed that his graphic testimony marked the first time many family members and friends learned about his profession. “Nobody knew,” Hayes told The Post. “Being exposed like that, in front of the entire world, took a mental toll.”

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Hayes had spent three decades carefully concealing his work from loved ones while building a lucrative career servicing millionaires, mobsters and celebrities across Manhattan. The chiseled 6-foot-2 escort, who also adopted the leather-clad dominator persona “The Punisher,” amassed a fleet of $150,000 Mercedes-Benz vehicles, a 41-foot yacht and a South Florida mansion.

Exclusive | I quit teaching for a life as a high-end male escort before becoming a Diddy ‘freak-off’ regular — here’s what I regret

His path into sex work began at age 24 in the early 2000s, after a painful breakup with his high school sweetheart. “I came home one day and told my mom, ‘I’m quitting my job and becoming a stripper,'” Hayes laughed, recalling his late mother’s disapproval. “I loved working with the kids. But after that bad breakup, I needed an ego boost.”

“Stripping was my gateway into escorting,” he revealed. “Once you begin selling sexuality, you’re gonna get propositioned for sex. Stripping gets you in front of clients.”

Exclusive | I quit teaching for a life as a high-end male escort before becoming a Diddy ‘freak-off’ regular — here’s what I regret

By 27, Hayes was tripling his teaching salary and pulling in six figures annually. He pocketed upwards of $200,000 from one long-term client alone. “Being a male escort is the biggest ego stroke that a man could ever want,” he boasted. “How many men in this world can actually say, ‘Women pay to be with me?'”

Exclusive | I quit teaching for a life as a high-end male escort before becoming a Diddy ‘freak-off’ regular — here’s what I regret

But the lifestyle carried hidden costs. Hayes became a regular participant in Combs’s notorious “freak-off” gatherings, and his testimony about those experiences formed part of the prosecution’s case against the music mogul, 56. Combs had paid Hayes for trysts with former girlfriend Cassie Ventura, 40, from 2012 through 2015, according to Hayes’s account.

The psychological damage accumulated across thousands of transactional encounters. Hayes developed depression-induced erectile dysfunction and abandoned dreams of basketball, educating underprivileged youth, and starting a family. “I remember waking up and, not necessarily thinking of myself as a piece of meat, but really considering all the things I’d sacrificed for this line of work,” he said.

Exclusive | I quit teaching for a life as a high-end male escort before becoming a Diddy ‘freak-off’ regular — here’s what I regret

The escort world has drawn renewed attention through an explosive lawsuit involving Gregg Starr, 38, a towheaded escort under the Cowboys4Angels agency. Marianne Flippo, 49, the widow of Roblox co-founder David Baszucki, filed an 18-page complaint in Manhattan Supreme Court last week accusing Starr of using “Svengali-like” powers to coerce her into buying out his $10 million contract with the company. Starr fired back to The Post, alleging he endured “abuse” and “mistreatment” throughout their “wild f–king ride” of a relationship.

Flippo claimed she didn’t realize she was hiring an escort for a trip to Italy, while Starr’s team argues their connection evolved into genuine love. Hayes, neither accusing any specific entity nor person of prostitution, offered a blunt assessment of such arrangements: “I’d say 99% of the time, male escorts are having sex with clients. Even if there’s an ‘Only for companionship’ stipulation, it’s a front.”

Exclusive | I quit teaching for a life as a high-end male escort before becoming a Diddy ‘freak-off’ regular — here’s what I regret

Hayes’s own romantic life mirrored the betrayal he witnessed in client relationships. His then-girlfriend, originally a client who divorced her husband to be with him, cheated on Hayes with another male escort. “It hit me so hard,” he groaned. “I was done.”

Exclusive | I quit teaching for a life as a high-end male escort before becoming a Diddy ‘freak-off’ regular — here’s what I regret

The incident sent him spiraling into mental health crises and sexual dysfunction. In 2021, he turned to a specialist he calls the “Michael Jordan of penis implants in New York City” for a surgical solution. Hayes now promotes his restored function on Instagram, describing the result as “immaculate” and comparing it to a Porsche 911.

Exclusive | I quit teaching for a life as a high-end male escort before becoming a Diddy ‘freak-off’ regular — here’s what I regret

Despite the turbulence, Hayes has redirected his experience toward helping others. He founded Hard Reset, a platform dedicated to building “complete, confident and capable men,” and now works as an author and mental health advocate. “Helping men find the tools needed in escorting, the bedroom or just life in general, really makes me feel good,” he said. “Giving back in this way makes me feel like everything I’ve experienced as an escort, all the things I’ve had to overcome and sacrifice, was all worth it. It was all for a greater purpose.”

Exclusive | I quit teaching for a life as a high-end male escort before becoming a Diddy ‘freak-off’ regular — here’s what I regret

Hayes also recounted a bizarre physical confrontation during his escorting days, when a husband walked in on him naked with the man’s wife. “He came charging at me like a WWF wrestler, but he couldn’t grab a hold of me because I was covered in baby oil,” Hayes remembered. “We were tussling, but he kept slipping off. The guy finally got so disgusted, yelled, ‘Just get out of here!’ So I left.”

He noted that cuckolding requests have surged over the past decade, with men frequently hiring him to sleep with their wives or girlfriends while watching. Some attempted to join sexually, crossing boundaries Hayes refused. “I’ve had to be careful about declining a request or interaction that crosses my boundaries,” he said.

Exclusive | I quit teaching for a life as a high-end male escort before becoming a Diddy ‘freak-off’ regular — here’s what I regret
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