Adverse modernism and gender discrepancies have inflicted grave injuries on social perceptions. The revolving -- still controversially perceived in certain societies -- topics around sexism and gender struggles have added flames to ended debates on gender understanding. This study set out to ascertain female audience opinion of cross-dressed male Instagram comedians, determine how the comedy skits represent the female gender, find out factors that motivate cross-dressing among male comedians and ascertain how the female audience reacts to the representation of women by male-cross dressed comedians on Instagram. The study used the survey quantitative research method. It was anchored on Technological determinism theory as propounded by McLuhan. The questionnaire was utilized to gather primary data while available literature served as the source of secondary data. The Taro Yamane technique was used to choose a sample size of 400 respondents from a population of 1,900,000. The researchers found that women do not appreciate male cross-dressed comedians, cross-dressed male comedians debase women by projecting them as dependent, unfaithful, gossips etc. Also, male comedians cross-dress because the female gender has diverse characteristics that could pass for rich comedy content and women are indifferent to their representation. The study recommended among other things that more women should be encouraged to venture into comedy and male cross-dressed comedians should foreground the strengths of the Nigerian women. Further studies can be conducted to access how cross-dressing affects comic cross-dressers choice of gender identity and expression beyond and outside the stage.