The long-term impacts of bullying, stress, sexual prejudice and stigma against members of the LGBTQ population are both worrisome and expansive. Bullying among adolescents is one of the clearest and most well documented risks to adolescent health(Nansel et al., 2004; Wilkins-Shurmer et al., 2003; Wolke, Woods, Bloomfield, & Karstadt, 2001) The present study examined the influence of sexual orientation to severity of bullying experience, coping strategies, emotion regulation and the interaction of gender role endorsements in relation to coping and emotion regulation strategy prediction. Extensive research exists to support high victimization experiences in LGBT individuals (Birkett et al., 2009; Robert H DuRant et al., n.d.; Kimmel & Mahler, 2003; Mishna et al., 2009) and separately, research also indicates support of gender role non conformity, social stress and long term coping skills (Galambos et al., 1990; Sánchez et al., 2010; Tolman, Striepe, & Harmon, 2003b). The goal of this study was to extend previous finding to find a relationship between the three variables: sexual orientation, victimization history, and non-traditional gender role endorse and utilizing those traits as predictors of future emotion regulation and coping strategies. The data suggests that as a whole LGBT identified individuals experience bullying at a significantly higher rate than their heterosexual counterparts. By utilizing gender role endorsement the relationship can be expanded to predict maladaptive emotion regulation skills, higher rates of perceived stress and increased fear of negative evaluation in lesbian women and gay men. The data was consistent for all hypotheses in the model: sexual identity significantly predicts higher bully score and atypical gender role endorsement is a moderator of victimization in LGBT individuals. The findings indicate high masculine endorsement in lesbians and high feminine endorsement in gay males can significantly predict victimization and maladaptive coping skills, emotion dysregulation, increased stress, and lack of emotional awareness.