This week we are talking anal penetration and "Peg The Patriarchy," a slogan coined by sex educator Luna Mattatas but made uber viral by Cara DeLevigne last week, wearing the stolen phrase in a Dior outfit on the red carpet of the Met Gala.  We talk to Luna about what she intended the phrase to mean when she coined it in 2015 and what Cara has taken it to mean as well as the Twitter discourse surrounding it and how she felt seeing it stolen. We also discuss why the term "pegging" itself can be problematic, its origin story with former guest Dan Savage and various other terms to use instead.  We then learn all about pegging welcuming back Lola Jean, sex educator and instructor of Remy's masturbation class, who teaches us about using fingers, using a strap on, and toys to use when first experiencing anal. We also talk to Brian who receives anal often from a cis female partner and tells us about how he got into it as well as his preparation for a date.  TW: Sensitive content Follow Luna @LunaMattatas + Lola @Lolajeandotcom  Follow us at @HowCumPodcast and @RemyKassimir  Sign up for access to extras and FULL unedited episodes with VIDEO for only $5 at patreon.com/howcum Check out our website for live forums & merch! RATE, REVIEW & SUBSCRIBE Thanks BetterHelp.  Get 10% off your first month at betterhelp.com/howcum Thanks Dipsea.  Get a 30 day free trial when you go to DipseaStories.com/howcum. Thanks to Foria. Get 20% off site wide, plus free shipping at foriawellness.com/howcum