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According to different conceptions of gender and transition, which are always singular but diversely impacted by social expectations, the body envelope of the transgender subject undergoes metamorphosis. During research interviews and projective tests (Rorschach and tat), two young transgender adults with neurotic profiles showed a marked sensitivity to societal norms, morals and expectations. Legitimacy, guilt and shame were recurrent issues. Different time frames of subjective, familial, social and bodily transitions came into play, including the passage to adulthood and student life outside the family circle. These two situations illustrate a discussion on bodily transitions and envelopes in transgender subjects.