Rectal sexually transmitted infections (STIs) are common in men at risk for urethral infections with these pathogens, particularly men who have sex with men (MSM). However, for those individuals not regularly seen by a clinician, screening for rectal STI is not currently a widespread option. Qualitative data and samples (i.e. self-obtained rectal specimens) were collected from 75 MSM in a variety of venues. Upon completion of the rectal self-sampling, each participant completed a brief interview regarding their overall experience with the process. Participants reported an overall high level of acceptability and comfort-level involved with self-sampling for rectal STI. Of the majority of men who agreed to provide a rectal self-sample, all reported that they would provide a sample again in the future. However, many men also appreciated the interaction with a health-care provider that a clinical setting offered. In conclusion, self-sampling is a feasible and acceptable option when offered to MSM in a range of community-based venues. Further research is needed to determine which combinations of STI testing and treatment methods (including self-sampling) are most appropriate for diverse groups of men.