Male Chastity, Orgasm denial So my girlfriend decided to lock me up for locktober. We experimented with chastity before, but never for a whole month. We are also into pegging. That being said, one of her goals is to get me to orgasm from anal penetration alone. So my question is, if I cum from being pegged, does that necessarily mean that I broke the rules of no cumming for locktober? October 9, 2018October 20, 2019 by jane Nah! It’d be amazing! Stop worrying about rules and get pegged till you squirt! It’s the most powerful experience for you both, seriously.