Ashley made her first official WWE appearance as a hired Diva on the August 21, 2005 pre-SummerSlam edition of Heat to conduct interviews with the fans, including WWE Legends Fabulous Moolah and Mae Young. Later that night, Ashley made her first appearance at a pay-per-view event, with Candice Michelle, Maria Kanellis, Stacy Keibler, and Torrie Wilson as they washed Mr. McMahon's limo in bikinis.
The following night on Raw, Candice Michelle and Torrie Wilson called out Ashley, claiming they wanted to welcome her to Raw. After Ashley came out, Candice and Torrie then turned heel by attacking her. Thus, starting Ashley's first feud in WWE. Ashley was beat up by Torrie, Candice and Victoria for the following two weeks, until she smartened up and brought the returning champion, Trish Stratus out to even the odds.
At the 2005 Unforgiven pay-per-view, Trish and Ashley defeated Torrie and Victoria (with Candice). After Ashley disrobed Candice on Raw the following night, the Ladies in Pink demanded a bra and panties match at WWE Homecoming, to which they lost.
After a debuting Mickie James allied herself with Trish and Ashley, Massaro was involved in the annual Fulfill Your Fantasy Battle Royal at Taboo Tuesday for the Woman's Championship and a regular battle royal on Raw, but did not win either.
On the January 3rd 2006 edition of RAW, Ashley came to the ring to defend fellow WWE Diva Maria against the Ladies in Pink stable. She proceeded to take out Candice Michelle and Torrie Wilson with a double clothesline,and tackled Victoria but eventually got caught with a double DDTby Torrie and Candice, branded "Double D.....DDT" by Jonathan Coachman.
--Wikipedia
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