Background: Sexual history-taking competence in medical students is an essential skill that they need to acquire. It requires them to learn to develop comfort in using sexuality-related language and raising the subject with patients. Sexual history exploration skills are inadequately taught in a significant number of medical schools. Aim: We studied comfort levels in using sexuality-related language in medical students who had no training yet in history taking. Methods: First-year medical students in a South African university engaged in an exercise in pairs-a dyad-alternating the role of interviewer and interviewee. Provided questions and answers were offered to the students, who videotaped their dyad interview and uploaded it to a safe university environment for peer review. Outcomes: As part of the exercise, students rated their comfort in the interview for 35 questions on a 5-point Likert scale. Students then participated in online discussion forums with fellow students and tutors on their experience. Results: Students posing the questions, the interviewers, were significantly more comfortable with the questions than interviewees. Total comfort scores over the 35 questions showed a roughly normal distribution for both. Questions with explicit sexual behavior or vocabulary were rated more uncomfortable by interviewers as well as interviewees. The total scores for interviewers showed a distribution with a longer tail toward discomfort. Female interviewees were significantly more uncomfortable than male interviewees, but this was not the case for interviewers. Dyads of 2 females were significantly more uncomfortable than mixed-gender and 2-male dyads. Qualitative data showed wide acceptance of the exercise by students, with increasing confidence and comfort in using sexually explicit terms in strong appreciation of the responder's perspective in the exercise, as well as awareness that receiving a question-the patient's position-is more uncomfortable. Clinical Translation: Data indicate that comfort assessment in asking sexuality-related questions with expected different levels of comfort and discomfort is a valuable measure that can evaluate progress in this skill. The data also suggest the need for students to select profiles and questions to provide a trauma-informed approach, knowing that some of the medical students will have experienced sexually related trauma, as in the general population. Strengths and Limitations: This study provides a method and student feedback in teaching sexual history elicitation and increasing comfort with sexual language in a clinical context. The study is limited to first-year medical students. Conclusion: Histories with provided questions and answers allow for rating of comfort and provision of trauma-informed education in developing sexual history exploration clinical skills.