Research suggests an association between risk for hypertension and decreased pain sensitivity. However, few studies have utilized non-behavioral indices of pain to corroborate subjective reports or sought to generalize these findings to women. Furthermore, it has not been established whether results obtained using well-controlled laboratory pain stimuli extend to naturalistic pain. In Study 1, 80 young adult women with (N = 40) and without (N = 40) a parental history of hypertension and with either normatively low or high resting systolic blood pressure (SBP) were exposed to two experimental pain stimuli, finger pressure and the cold pressor test. In addition to behavioral pain measures, respiratory sinus arrhythmia (RSA) reactions to pain were also assessed. Women with a parental history of hypertension and/or normatively high resting SBP experienced significantly less pain, as assessed by both behavioral and RSA measures. In Study 2, 37 of the participants from Study 1 monitored their behaviors, affect, and physical symptoms, three times a day for 32 days. Laboratory pain sensitivity was significantly correlated with daily reports of pain but not gastrointestinal symptoms. The present results confirm an association between risk for hypertension and hypoalgesia in women and suggest generalizability of this relationship to everyday life.