Little information is available about sexual risk, protective, and disclosure practices among Black bisexually active men and how these may be amenable to intervention when necessary. In-depth interviews were conducted with 30 at-risk urban Black men who have sex with both men and women (MSMW). Participants reported protecting themselves and their partners through routine HIV testing, using condoms consistently, engaging in strategic positioning during sexual activity, and limiting the number of sexual partners. In addition, they described several reasons for not using protection, including not having condoms available, enjoying sexual activity more without condoms, and perceiving female partners to be “safer” than male partners. Disclosure of bisexuality was complex and reportedly difficult, in particular to female and gay-identified male partners. Future interventions must not only build protection and disclosure skills among MSMW, but also increase broader social awareness and acceptance of male bisexuality.