411 From ‘Friends with Benefits’ to ‘Sextortion:’ A Nuanced Investigation of Adolescents’ Online Sexual Risk Experiences ASHWAQ ALSOUBAI, Vanderbilt University, U.S.A JIHYE SONG, University of Central Florida, U.S.A AFSANEH RAZI, Drexel University, U.S.A NURUN NAHER, University of Central Florida, U.S.A MUNMUN DE CHOUDHURY, Georgia Institute of Technology, U.S.A PAMELA J. WISNIEWSKI, Vanderbilt University, U.S.A Sexual exploration is a natural part of adolescent development; yet, unmediated internet access has enabled teens to engage in a wider variety of potentially riskier sexual interactions than previous generations, from normatively appropriate sexual interactions to sexually abusive situations. Teens have turned to online peer support platforms to disclose and seek support about these experiences. Terefore, we analyzed posts ( = 45, 955) made by adolescents (ages 13–17) on an online peer support platform to deeply examine their online sexual risk experiences. By applying a mixed methods approach, we 1) accurately (average of   = 0.90) identifed posts that contained teen disclosures about online sexual risk experiences and classifed the posts based on level of consent (i.e., consensual, non-consensual, sexual abuse) and relationship type (i.e., stranger, dating/friend, family) between the teen and the person in which they shared the sexual experience, 2) detected statistically signifcant diferences in the proportions of posts based on these dimensions, and 3) further unpacked the nuance in how these online sexual risk experiences were typically characterized in the posts. Teens were signifcantly more likely to engage in consensual sexting with friends/dating partners; unwanted solicitations were more likely from strangers and sexual abuse was more likely when a family member was involved. We contribute to the HCI and CSCW literature around youth online sexual risk experiences by moving beyond the false dichotomy of “safe” versus “risky”. Our work provides a deeper understanding of technology-mediated adolescent sexual behaviors from the perspectives of sexual well-being, risk detection, and the prevention of online sexual violence toward youth. Content Warning: Sensitive topics, including sexual risk behaviors involving minors and sexual abuse, are discussed in this paper. Readers should use their discretion as to whether they would like to proceed. CCS Concepts: • Online Safety → Adolescents Online Sexual Experiences;• Artifcial Intelligent → Natural Language Processing (NLP) . Additional Key Words and Phrases: Sexting, Sexual Risks, Sexual Risk Detection, Adolescents Disclosures, Artifcial Intelligence, Social Media Authors’ addresses: Ashwaq Alsoubai, Vanderbilt University, Nashville, Tennessee, U.S.A, atalsoubai@kau.edu.sa; Jihye Song, University of Central Florida, Orlando, Florida, U.S.A, chsong@knights.ucf.edu; Afsaneh Razi, ar3882@drexel.edu, Drexel University, Philadelphia, Pennsylvania, U.S.A, 19104; Nurun Naher, University of Central Florida, Orlando, Florida, U.S.A, nurun@knights.ucf.edu; Munmun De Choudhury, Georgia Institute of Technology, 30318, Atlanta, Georgia, U.S.A, munmund@gatech.edu; Pamela J. Wisniewski, Vanderbilt University, Nashville, Tennessee, U.S.A, pamela.wisniewski@ vanderbilt.edu. Permission to make digital or hard copies of all or part of this work for personal or classroom use is granted without fee provided that copies are not made or distributed for proft or commercial advantage and that copies bear this notice and the full citation on the frst page. Copyrights for components of this work owned by others than ACM must be honored. Abstracting with credit is permited. To copy otherwise, or republish, to post on servers or to redistribute to lists, requires prior specifc permission and/or a fee. Request permissions from permissions@acm.org. © 2022 Association for Computing Machinery. 2573-0142/2022/11-ART411 $15.00 https://doi.org/10.1145/3555136 Proc. ACM Hum.-Comput. Interact., Vol. 6, No. CSCW2, Article 411. Publication date: November 2022.