Little information is available about sexual risk and disclosure practices among Black men who have sex with both men and women (MSMW) and how these may be amenable to intervention when necessary. In-depth interviews were conducted with 30 at-risk Black 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.” Disclosure of bisexuality to female and “gay” male partners, in particular, was reportedly difficult. Future interventions must not only build protection and disclosure skills among MSMW but increase social awareness and acceptance of male bisexuality.