Background: There is growing evidence that shows the possible role of anal intercourse between the same sex in the epidemiology of HIV/AIDS in Africa. Such generalization is also applicable in African countries where such sexual behavior has become an emergent phenomenon. Objective: To asses the possible role of MSM in the epidemiology of HIV/AIDS in Addis Ababa. Methods: An ethnographic study was conducted in different parts of Addis Ababa between January’06- March’06. Snowball sampling method was used to recruit MSM, hot line counselors and victims of anal rape. Four Focus group discussions with MSM, key informant interviews with three counselors as well as with three anal rape victims and observation at bars, streets and tearooms were done. Data on the extent, patterns of sexuality and related issues on MSM were collected and analyzed using open code software and ground theory approach to qualitative data analysis. Results: Contextual factors (socio-cultural and politico legal issues) were found to be the bases of the development of risk behaviors to HIV/AIDS. This contextual factor operates through mediators such as individual behavioral causes and immediate casual factors. Different strategies were explored for possible cross bridging of infection between the subgroup and the other heterosexual community. Conclusions: The practice of MSM is beyond what one would expect in the city and different factors are seen to lead people to get engaged in such sexual behavior. As this practice exposes to HIV/AIDS related risks, it is high time to discuss this issue openly with in the context of current efforts to control the HIV pandemic.