As a personal assistant, Anna Claire Clouds has always managed to be an essential and valued member of her boss' team. Her current boss, Casey Calvert, is no different and thinks that Anna has been doing a wonderful job. They actually get along quite well together. So well, in fact, that Casey decides to send Anna a very special calendar invite one day... The calendar invite is titled 'Office Fuck Session With The Boss' and even has a detailed itinerary of all the kinky things Casey wants Anna to do to her. Anna is baffled, debating whether or not she should go to HR. But eventually, she decides that this might be a great way to get even closer to her boss in a way she'd never even imagined. She goes to Casey's office at the appointed time and Casey is waiting for her, ready to get frisky. Casey bends Anna over the desk and eats her out from behind, after which she spreads her legs for her assistant to do the same to her. Anna rips Casey's pantyhose open and buries her tongue in her boss' wet pussy, loving the way it tastes. Casey then dons a strapon and fucks her willing assistant all over the office in various positions, letting Anna lick her pussy juices off the shaft after she's cum all over it.