The article addresses a somewhat ambiguous and double-edged legal and policy framework relating to the tabooed commercial sex industry in Bangladesh. This dichotomous phenomenon is further aggravated by an aeonian trajectory of social vulnerability and economic exclusion that invisibly enslaves the victims of the process in an ostracised cycle of servitude and exploitation. Although the national Constitution adopts a preventive policy against prostitution, law does not as such prohibit commercial sex work by an adult woman working in a brothel having made an affidavit in this regard. But, at the same time, the law renders some forms of sex work illegal, while sex between males has been made culpable offence even on its own. On the other hand, blemish community mind-set, engraved stigma and lack of respect for fundamental rights continue to diminish any chances of sex workers’ reintegration to the mainstream of the society, perpetuate poverty, and increase their vulnerability to STI/HIV/AIDS. This paradox in policy and practice represents a centuries-old oxymoron in social and legal philosophical parlance in many parts of the globe including Bangladesh.