Should I Wear This Shirt Out Tomorrow? Should I Wear This Shirt Out Tomorrow? 107 5 years ago, May 30, 2019 Titty Drop
Going Out For Drinks Wearing A Dress With No Bra…should I Keep The Straps Up Or Off The Shoulders For Easier Access? Going Out For Drinks Wearing A Dress With No Bra…should I Keep The Straps Up Or Off The Shoulders For Easier Access? 75 5 years ago, August 4, 2019 Big Boobs Gonewild
Should I Wear This Shirt Out Tonight? [Self] Should I Wear This Shirt Out Tonight? [Self] 33 4 years ago, July 25, 2020 Titties
Getting Ready To Go Out, Should I Wear My Plug Under My Dress? Getting Ready To Go Out, Should I Wear My Plug Under My Dress? 31 4 years ago, November 7, 2019 Curvy Cuties
Should I Go Out Wearing This? Should I Go Out Wearing This? 31 5 years ago, January 18, 2019 Cleavage
Where Should I Wear This Outfit? Where Should I Wear This Outfit? 30 3 years ago, November 17, 2020 Cleavage
Probably Shouldn't Wear This Shirt Without A Bra In Public Hey? Probably Shouldn't Wear This Shirt Without A Bra In Public Hey? 27 3 years ago, January 11, 2021 Titty Drop
Probably Shouldnt Wear This Shirt Out In Public Probably Shouldnt Wear This Shirt Out In Public 18 4 years ago, April 28, 2020 Titty Drop
Use This OC Drop To Help Me Decide If I Should Wear This Milkmaid Top Out Braless Tonight Use This OC Drop To Help Me Decide If I Should Wear This Milkmaid Top Out Braless Tonight 7 3 years ago, June 16, 2021 Boob Bounce
The Mrs Is On Her First Girls Night Out In 4 Months Tonight Wearing This. Should I Be Worried Guys? The Mrs Is On Her First Girls Night Out In 4 Months Tonight Wearing This. Should I Be Worried Guys? 5 4 years ago, July 5, 2020 Cleavage