Jenna Dewan recalls the time Janet Jackson gifted her with a 'pleasure chest'

At age 19, Jenna Dewan was left a little speechless upon receiving a NSFW Valentine's Day gift from her employer at the time, Janet Jackson.

The World of Dance host used to be a back-up dancer for the music legend and gushed over the perks of working for her during an appearance on Tuesday's Jimmy Kimmel Live

"She was a great boss, she was a very generous boss. She would give us, like, amazing gifts," she recalled. "I have a blinged-out diamond watch, which, by the way, should everything go away, I'm like, 'I could sell this watch!'"

Dewan added that she and the other back-up dancers got a more unconventional gift from Jackson come Feb. 14. "On Valentine's Day -- and mind you, I'm 19, on tour with Janet, so I'm like, baby, baby, baby naive -- she gives you, like, a box of vibrators," she remembered. "Like, a pleasure chest. All the dancers [got a box]. But still, I was like, 'What is this??' I was, mind blown."

Dewan told Kimmel that getting on Jackson's tour was a lifelong dream for her, and one that came true when the singer personally pulled her aside at a music video shoot.

"I came out to L.A. I was going to college, and then I auditioned for her video, and then she came into the room one day, and was like, 'Um, everyone can leave. Jenna, can you stay?' And I was like, 'Uhhh, am I being fired? Like what's going on here,'” the 37-year-old Step Up star recalled. “She walks in, she was like, 'Do you wanna go on tour with me?' And I just freaked out. You know, that was my dream job."

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Billboard Music Awards 2018: Janet Jackson
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Billboard Music Awards 2018: Janet Jackson
LAS VEGAS, NV - MAY 20: Honoree Janet Jackson attends the 2018 Billboard Music Awards at MGM Grand Garden Arena on May 20, 2018 in Las Vegas, Nevada. (Photo by Frazer Harrison/Getty Images)
LAS VEGAS, NV - MAY 20: Recording artist Janet Jackson attends the 2018 Billboard Music Awards at MGM Grand Garden Arena on May 20, 2018 in Las Vegas, Nevada. (Photo by John Shearer/Getty Images for dcp)
LAS VEGAS, NV - MAY 20: Honoree Janet Jackson accepts the Icon Award onstage during the 2018 Billboard Music Awards at MGM Grand Garden Arena on May 20, 2018 in Las Vegas, Nevada. (Photo by Kevin Winter/Getty Images)
LAS VEGAS, NV - MAY 20: Honoree Janet Jackson attends the 2018 Billboard Music Awards at MGM Grand Garden Arena on May 20, 2018 in Las Vegas, Nevada. (Photo by Frazer Harrison/Getty Images)
LAS VEGAS, NV - MAY 20: Honoree Janet Jackson attends the 2018 Billboard Music Awards at MGM Grand Garden Arena on May 20, 2018 in Las Vegas, Nevada. (Photo by Frazer Harrison/Getty Images)
LAS VEGAS, NV - MAY 20: Recording artist Janet Jackson attends the 2018 Billboard Music Awards at MGM Grand Garden Arena on May 20, 2018 in Las Vegas, Nevada. (Photo by Matt Winkelmeyer/Getty Images for dcp)
LAS VEGAS, NV - MAY 20: Recording artist Janet Jackson perfroms onstage during the 2018 Billboard Music Awards at MGM Grand Garden Arena on May 20, 2018 in Las Vegas, Nevada. (Photo by Ethan Miller/Getty Images)
LAS VEGAS, NV - MAY 20: Honoree Janet Jackson accepts the Icon Award onstage during the 2018 Billboard Music Awards at MGM Grand Garden Arena on May 20, 2018 in Las Vegas, Nevada. (Photo by Kevin Winter/Getty Images)
LAS VEGAS, NV - MAY 20: Recording artist Janet Jackson attends the 2018 Billboard Music Awards at MGM Grand Garden Arena on May 20, 2018 in Las Vegas, Nevada. (Photo by Jeff Kravitz/FilmMagic)
LAS VEGAS, NV - MAY 20: Recording artist Janet Jackson attends the 2018 Billboard Music Awards at MGM Grand Garden Arena on May 20, 2018 in Las Vegas, Nevada. (Photo by Jeff Kravitz/FilmMagic)
LAS VEGAS, NV - MAY 20: Recording artist Janet Jackson attends the 2018 Billboard Music Awards at MGM Grand Garden Arena on May 20, 2018 in Las Vegas, Nevada. (Photo by Kevin Mazur/WireImage)
LAS VEGAS, NV - MAY 20: Honoree Janet Jackson performs onstage at the 2018 Billboard Music Awards at MGM Grand Garden Arena on May 20, 2018 in Las Vegas, Nevada. (Photo by Matt Winkelmeyer/Getty Images for dcp)
LAS VEGAS, NV - MAY 20: Honoree Janet Jackson performs onstage during the 2018 Billboard Music Awards at MGM Grand Garden Arena on May 20, 2018 in Las Vegas, Nevada. (Photo by Kevin Winter/Getty Images)
LAS VEGAS, NV - MAY 20: Recording artist Janet Jackson attends the 2018 Billboard Music Awards at MGM Grand Garden Arena on May 20, 2018 in Las Vegas, Nevada. (Photo by John Shearer/Getty Images for dcp)
LAS VEGAS, NV - MAY 20: Recording artist Janet Jackson attends the 2018 Billboard Music Awards at MGM Grand Garden Arena on May 20, 2018 in Las Vegas, Nevada. (Photo by Jeff Kravitz/FilmMagic)
LAS VEGAS, NV - MAY 20: Honoree Janet Jackson performs onstage during the 2018 Billboard Music Awards at MGM Grand Garden Arena on May 20, 2018 in Las Vegas, Nevada. (Photo by Kevin Winter/Getty Images)
LAS VEGAS, NV - MAY 20: Honoree Janet Jackson performs onstage during the 2018 Billboard Music Awards at MGM Grand Garden Arena on May 20, 2018 in Las Vegas, Nevada. (Photo by Kevin Winter/Getty Images)
LAS VEGAS, NV - MAY 20: Honoree Janet Jackson performs onstage during the 2018 Billboard Music Awards at MGM Grand Garden Arena on May 20, 2018 in Las Vegas, Nevada. (Photo by Kevin Winter/Getty Images)
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The tour turned out to be much more lavish than Dewan could have ever imagined.

“I was in college, I was going to USC, so I went from like dorm life to being on private jets like right away,” she explained. “One time, we’re in rehearsal and we’re rehearsing for the HBO special and [Janet] comes in and she’s like, ‘So, everybody pack your bags. We’re going to fly to Anguilla tomorrow and rehearse for two weeks. Everybody’s celebrating and I’m like ‘Where’s Anguilla?’”

Dewan continued, “We’d wake up, go out on to the beach, lay out, and rehearse from like two to seven -- and then go to the clubs. Then repeat for two weeks. That’s insane! Who does that?”

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Jenna Dewan out and about
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Jenna Dewan out and about
CULVER CITY, CA - NOVEMBER 10: Jenna Dewan attends the 2018 Baby2Baby Gala Presented by Paul Mitchell at 3LABS on November 10, 2018 in Culver City, California. (Photo by Axelle/Bauer-Griffin/FilmMagic)
CULVER CITY, CA - NOVEMBER 10: Jenna Dewan arrives at the The 2018 Baby2Baby Gala Presented By Paul Mitchell Event at 3LABS on November 10, 2018 in Culver City, California. (Photo by Steve Granitz/WireImage)
CULVER CITY, CA - NOVEMBER 10: Jenna Dewan, Jessica Alba and Olivia Munn attend The 2018 Baby2Baby Gala Presented By Paul Mitchell Event at 3LABS on November 10, 2018 in Culver City, California. (Photo by Jon Kopaloff/FilmMagic)
WEST HOLLYWOOD, CA - SEPTEMBER 15: Jenna Dewan attends Variety and Women In Film's 2018 Pre-Emmy celebration held at Cecconi's on September 15, 2018 in West Hollywood, California. (Photo by Michael Tran/FilmMagic)
LOS ANGELES, CA - AUGUST 08: Jenna Dewan is seen at LAX on August 08, 2018 in Los Angeles, California. (Photo by BG023/Bauer-Griffin/GC Images)
LOS ANGELES - JULY 31: The Late Late Show with James Corden airing Tuesday, July 24, 2018, with guests Mandy Moore and Jenna Dewan. (Photo by Terence Patrick/CBS via Getty Images)
THE TONIGHT SHOW STARRING JIMMY FALLON -- Episode 0892 -- Pictured: Actress Jenna Dewan arrives on June 26, 2018 -- (Photo by: Andrew Lipovsky/NBC/NBCU Photo Bank via Getty Images)
BEVERLY HILLS, CA - MAY 22: Actress Jenna Dewan attends the 28th Annual EMA Awards Ceremony at Montage Beverly Hills on May 22, 2018 in Beverly Hills, California. (Photo by Axelle/Bauer-Griffin/FilmMagic)
BEVERLY HILLS, CA - MAY 22: Actress Jenna Dewan attends the 28th Annual EMA Awards Ceremony at Montage Beverly Hills on May 22, 2018 in Beverly Hills, California. (Photo by Axelle/Bauer-Griffin/FilmMagic)
JIMMY KIMMEL LIVE! - 'Jimmy Kimmel Live!' airs every weeknight at 11:35 p.m. EDT and features a diverse lineup of guests that include celebrities, athletes, musical acts, comedians and human interest subjects, along with comedy bits and a house band. The guests for Tuesday, May 22 included Johnny Knoxville ('Action Point'), Jenna Dewan ('World of Dance'), and musical guest Franz Ferdinand. (Randy Holmes/ABC via Getty Images) JENNA DEWAN
LAS VEGAS, NV - MAY 20: Actor Jenna Dewan attends the 2018 Billboard Music Awards at MGM Grand Garden Arena on May 20, 2018 in Las Vegas, Nevada. (Photo by Frazer Harrison/Getty Images)
LAS VEGAS, NV - MAY 20: Actor Jenna Dewan attends the 2018 Billboard Music Awards at MGM Grand Garden Arena on May 20, 2018 in Las Vegas, Nevada. (Photo by Frazer Harrison/Getty Images)
LAS VEGAS, NV - MAY 18: Actress/dancer Jenna Dewan attends VEGAS Magazine's 15th anniversary party at the Red Rock Casino, Resort and Spa on May 18, 2018 in Las Vegas, Nevada. (Photo by Bryan Steffy/Getty Images for VEGAS Magazine)
ROCKEFELLER CENTER, NEW YORK, UNITED STATES - 2018/05/14: Jenna Lee Dewan-Tatum (Jenna Dewan) attends the 2018 NBCUniversal Upfront presentation at Rockefeller Center. (Photo by Lev Radin/Pacific Press/LightRocket via Getty Images)
NEW YORK, NY - MAY 14: Jenna Dewan visits Build Series to discuss Season 2 of 'World of Dance' at Build Studio on May 14, 2018 in New York City. (Photo by Slaven Vlasic/Getty Images)
UNIVERSAL CITY, CA - MAY 02: TV host Jenna Dewan attends NBCUniversal's Summer Press Day 2018 at The Universal Studios Backlot on May 2, 2018 in Universal City, California. (Photo by Alberto E. Rodriguez/Getty Images)
NORTH HOLLYWOOD, CA - MAY 01: Jenna Dewan attends FYC Event For NBC's 'World Of Dance' at Saban Media Center on May 1, 2018 in North Hollywood, California. (Photo by Araya Diaz/WireImage)
NEW YORK, NY - APRIL 20: Actor Jenna Dewan attends as Jenna Dewan is honored as 2018 St. Jude Children's Research Hospital 'Humanitarian Of The Year' during the fifth annual St. Jude Hope & Heritage Gala on April 20, 2018 in New York City. (Photo by Craig Barritt/Getty Images for St. Jude Children's Research Hospital)
PASADENA, CA - MARCH 25: Jenna Dewan Tatum attends the Hunter For Target Ultimate Family Festival at Brookside Golf Club on March 25, 2018 in Pasadena, California. (Photo by Alberto E. Rodriguez/Getty Images)
INGLEWOOD, CA - MARCH 11: Actress Jenna Dewan Tatum attends the 2018 iHeartRadio Music Awards at the Forum on March 11, 2018 in Inglewood, California. (Photo by Axelle/Bauer-Griffin/FilmMagic)
INGLEWOOD, CA - MARCH 24: Jenna Dewan Tatum and Everly Tatum onstage at Nickelodeon's 2018 Kids' Choice Awards at The Forum on March 24, 2018 in Inglewood, California. (Photo by Chris Polk/KCA2018/Getty Images)
BEVERLY HILLS, CA - MARCH 04: Actress Jenna Dewan Tatum attends the 2018 Vanity Fair Oscar Party hosted by Radhika Jones at Wallis Annenberg Center for the Performing Arts on March 4, 2018 in Beverly Hills, California. (Photo by Axelle/Bauer-Griffin/FilmMagic)
UNIVERSAL CITY, CA - JANUARY 30: Jenna Dewan Tatum attends the photo op for NBC's 'World Of Dance' held at NBC Universal Lot on January 30, 2018 in Universal City, California. (Photo by Michael Tran/FilmMagic)
BEVERLY HILLS, CA - FEBRUARY 24: Jenna Dewan Tatum attends the 12th Annual Los Angeles Ballet Gala at the Beverly Wilshire Four Seasons Hotel on February 24, 2018 in Beverly Hills, California. (Photo by Frazer Harrison/Getty Images)
WEST HOLLYWOOD, CA - DECEMBER 07: Jennifer Meyer and Jenna Dewan Tatum attend Gilt.com, Jennifer Meyer & Jenna Dewan Tatum Launch Exclusive Jewelry Collection Benefitting Baby2Baby at Sunset Tower Hotel on December 7, 2017 in West Hollywood, California. (Photo by Stefanie Keenan/Getty Images for Gilt.com)
LOS ANGELES, CA - NOVEMBER 19: Actress Jenna Dewan-Tatum arrives at the 2017 American Music Awards at Microsoft Theater on November 19, 2017 in Los Angeles, California. (Photo by Axelle/Bauer-Griffin/FilmMagic)
LOS ANGELES, CA - NOVEMBER 06: Jenna Dewan Tatum attends the premiere of 'War Dog: A Soldier's Best Friend' at Directors Guild Of America on November 6, 2017 in Los Angeles, California. (Photo by Jason LaVeris/FilmMagic)
LOS ANGELES, CA - NOVEMBER 06: Channing Tatum and Jenna Dewan Tatum attend the premiere of 'War Dog: A Soldier's Best Friend' at Directors Guild Of America on November 6, 2017 in Los Angeles, California. (Photo by Jason LaVeris/FilmMagic)
WEST HOLLYWOOD, CA - SEPTEMBER 19: Actress Jenna Dewan Tatum attends NBC's 'World of Dance' celebration at Delilah on September 19, 2017 in West Hollywood, California. (Photo by Jason LaVeris/FilmMagic)
LOS ANGELES, CA - SEPTEMBER 09: Actress Jenna Dewan Tatum attends the 2017 Creative Arts Emmy Awards at Microsoft Theater on September 9, 2017 in Los Angeles, California. (Photo by Jason LaVeris/FilmMagic)
NEW YORK, NY - SEPTEMBER 08: Actress Jenna Dewan Tatum attends the Cushnie Et Ochs fashion show during New York Fashion Week: The Shows at Gallery 1, Skylight Clarkson Sq on September 8, 2017 in New York City. (Photo by Desiree Navarro/WireImage)
NEW YORK, NY - SEPTEMBER 07: Young Living Essential Oils and Jenna Dewan Tatum, actress, dancer and avid Young Living Essential Oils fan, announce the brand's 'Scents Of Self' Spring 2018 limited edition Fashion Week essential oil collection on September 7, 2017 in New York City. (Photo by Bryan Bedder/Getty Images for Young Living)
HOLLYWOOD, CA - AUGUST 03: Actress Jenna Dewan Tatum attends the premiere of 'Comrade Detective' at ArcLight Hollywood on August 3, 2017 in Hollywood, California. (Photo by Jason LaVeris/FilmMagic)
NEW YORK, NY - AUGUST 03: Actress Jenna Dewan Tatum.is seen outside Live With Kelly on August 3, 2017 in New York City. (Photo by Raymond Hall/GC Images)
THE TONIGHT SHOW STARRING JIMMY FALLON -- Episode 0709 -- Pictured: (l-r) Actress/Dancer Jenna Dewan Tatum teaches host Jimmy Fallon dance moves during an interview on July 21, 2017 -- (Photo by: Andrew Lipovsky/NBC/NBCU Photo Bank via Getty Images)
SANTA MONICA, CA - JUNE 02: Jenna Dewan Tatum attends Baby2Baby Beach Playdate Presented By Havaianas on June 2, 2017 in Santa Monica, California. (Photo by Stefanie Keenan/Getty Images for Baby2Baby/Havaianas)
LOS ANGELES - MAY 22: Jenna Dewan Tatum and Lionel Richie chat with James Corden during 'The Late Late Show with James Corden,' Monday, May 22, 2017 (12:35 PM-1:37 AM ET/PT) On The CBS Television Network. (Photo by Terence Patrick/CBS via Getty Images)
UNIVERSAL CITY, CA - MAY 22: Jenna Dewan Tatum visits 'Extra' at Universal Studios Hollywood on May 22, 2017 in Universal City, California. (Photo by Noel Vasquez/Getty Images)
NEW YORK, NY - MAY 15: Actress Jenna Dewan-Tatum enters a Midtown Manhattan hotel on MAY 15, 2017 in New York City. (Photo by Ray Tamarra/GC Images)
NEW YORK, NY - MAY 15: Actress and dancer Jenna Dewan Tatum of World of Dance attends Entertainment Weekly & People New York Upfronts at 849 6th Ave on May 15, 2017 in New York City. (Photo by Gilbert Carrasquillo/FilmMagic)
NEW YORK, NY - MAY 15: Jenna Dewan Tatum attends the 2017 NBCUniversal Upfront at Radio City Music Hall on May 15, 2017 in New York City. (Photo by Dia Dipasupil/Getty Images)
WATCH WHAT HAPPENS LIVE WITH ANDY COHEN -- Pictured: Jenna Dewan Tatum -- (Photo by: Charles Sykes/Bravo/NBCU Photo Bank via Getty Images)
NEW YORK, NY - MAY 12: Jenna Dewan Tatum is seen on May 12, 2017 in New York City. (Photo by Patricia Schlein/Star Max/GC Images)
LOS ANGELES, CA - MAY 04: Jenna Dewan Tatum is seen with FIJI Water on May 4, 2017 in Los Angeles, California. (Photo by Frazer Harrison/GC Images)
LAS VEGAS, NV - APRIL 21: Actor Channing Tatum (L) and actress Jenna Dewan Tatum attend the grand opening of 'Magic Mike Live Las Vegas' at the Hard Rock Hotel & Casino on April 21, 2017 in Las Vegas, Nevada. (Photo by Ethan Miller/Getty Images)
BEVERLY HILLS, CA - MARCH 20: Jenna Dewan Tatum attends the 2017 NBCUniversal summer press day The Beverly Hilton Hotel on March 20, 2017 in Beverly Hills, California. (Photo by Jason LaVeris/FilmMagic)
WEST HOLLYWOOD, CA - MARCH 09: Actors Michelle Trachtenberg, Jenna Dewan Tatum and model Anne Vyalitsyna attend (ANDAZ) RED Suite Opening at Andaz West Hollywood on March 9, 2017 in West Hollywood, California. (Photo by Rachel Murray/WireImage)
WORLD OF DANCE -- 'Duels' Episode 104 -- Pictured: Jenna Dewan Tatum -- (Photo by: Trae Patton/NBC/NBCU Photo Bank via Getty Images)
LAS VEGAS, NV - FEBRUARY 21: Danskin Brand Ambassador Jenna Dewan Tatum celebrates the fall collection at PROJECT Women's at the Mandalay Bay Convention Center on February 21, 2017 in Las Vegas, Nevada. (Photo by David Becker/Getty Images for Iconix Brand Group)
UNIVERSAL CITY, CA - JANUARY 25: Jenna Dewan Tatum attends the photo op for NBC's 'World Of Dance' at NBC Universal Lot on January 25, 2017 in Universal City, California. (Photo by Araya Diaz/WireImage)
UNIVERSAL CITY, CA - JANUARY 25: (L-R) Dancer Derek Hough, singer-actress-dancer Jennifer Lopez, singer-songwriter-dancer Ne-Yo and actress-dancer Jenna Dewan Tatum attend the Photo Op for NBC's 'World Of Dance' at NBC Universal Lot on January 25, 2017 in Universal City, California. (Photo by Jeffrey Mayer/WireImage)
BEVERLY HILLS, CA - DECEMBER 18: Jenna Dewan Tatum and Molly Sims attend Baby2Baby Holiday Party Presented By Old Navy at Montage Beverly Hills on December 18, 2016 in Beverly Hills, California. (Photo by Stefanie Keenan/Getty Images for Baby2Baby)
BEVERLY HILLS, CA - JANUARY 08: Actress Jenna Dewan Tatum arrives at the 18th Annual Post-Golden Globes Party hosted by Warner Bros. Pictures and InStyle at The Beverly Hilton Hotel on January 8, 2017 in Beverly Hills, California. (Photo by Axelle/Bauer-Griffin/FilmMagic)
MARINA DEL REY, CA - NOVEMBER 19: Actress Jenna Dewan Tatum arrives at the 1st Annual Marie Claire Young Women's Honors at the Marina del Rey Marriott on November 19, 2016 in Marina del Rey, California. (Photo by Amanda Edwards/WireImage)
Actress Jenna Dewan Tatum attends the 2016 Glamour Women Of The Year Awards in Hollywood, California, on November 14, 2016. / AFP / VALERIE MACON (Photo credit should read VALERIE MACON/AFP/Getty Images)
WEST HOLLYWOOD, CA - NOVEMBER 17: Actress Jenna Dewan Tatum arrives at Variety and WWD 2nd Annual StyleMakers Awards at Quixote Studios West Hollywood on November 17, 2016 in West Hollywood, California. (Photo by Axelle/Bauer-Griffin/FilmMagic)
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She and Jackson are clearly still close as they just reunited at Sunday's Billboard Music Awards. They even shared the stage -- along with some of Jackson’s other former dancers -- last October during the 52-year-old singer's concert at the Hollywood Bowl.

"Generations of Janet kids brought together! ♥️," Dewan captioned an Instagram photo at the time, which featured herself and the other former backup dancers at Jackson's show. "Dancing for her was always way more than a job, it was being part of a legacy. I have been pinching myself all day being in a room years later dancing with these legends. Excited to share soon."

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