Janet Lupo, Playboy's Miss November 1975. With a bust size of 38DDD, many believe her to be the largest-breasted Playmate in the magazine's history. zNSFW

https://i.imgur.com/Kj0zzhR.jpg

User: ChivalrousPervert

Categories: NostalgiaFapping, u_tpc671, Lovelyboobs, Titties, uniboobs, u_soloassisland, u_macattak33

15 year old me would have KILLED to have seen Kelly Kapowski's nipples.

Keira Knightley

Keira Knightley

Sara Underwood, 2007 Playmate of the Year.

Carmen Electra, remember this photoshoot?

Lisa Boyle Was a 90s Fave

Elisa Cuthbert

Janine Lindemulder pre body tats

Samantha Fox

Young Elizabeth Hurley

Rosario Dawson

Britney Spears by Mark Seliger for Rolling Stone Magazine (2001)

Eliza Dushku

Debbie Gibson

Kelly Monaco Monday!

Sasha Grey

Charlie's angels

Tara Reid (early 2000s)

A well-deserved award for Ashlynn Brooke

Elisha Cuthbert

Tiffani Amber Theissen

Leah Remini

I can't forget Maria Ozawa

Kristi Myst - always thought she was super hot

Carrie Fisher (Enhanced) Princess Leia Bikini

Jessica Alba - Maxim 2003 (more in comments)

Jennifer Aniston in formal wear

Ever bust a load to this pic? Gemma Hiles (Playboy)

Veronica Zemanova - 1990's Goddess

Michelle Johnson - Blame It On Rio (1984)