This article addresses an idiosyncrasy in Michelangelo’s art: the consistent depiction of angels without wings. This iconographical feature is not adequately explained by Art Historical methodolgy. A psychological explanation is offered based on the fact that, during the short period of Michelangelo`s infatuation with a young man, Tommaso Cavalieri, imagery of winged angels, winged figures, and winged flight became prominent in Michelangelo`s art, while in his poetry he repeatedly addressed Tommaso as a winged angel. This article argues that Michelangelo drew upon the established metaphorical meaning of wings as symbolizing permissible Platonic love in order to convey passionate homoerotic feelings. It is proposed that the homoerotic significance of wings and winged nude figures led the deeply religious artist, who repeatedly denied his homosexual inclinations, to avoid them in his depictions of angels, so as not to desecrate his Christian art with his sinful feelings.