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The Tomgirl Pictures are a series of pictures taken by Chris that were leaked by Surfshack Tito on 28 April 2011. These are most notable for highlighting Chris at the beginning of his eventual gender transition.

According to Tito, the cross-dressing was apparently Chris's reaction to someone advising him to get in touch with his feminine side. Emily gave a somewhat different explanation, stating that what kicked it off was someone suggested to Chris to be a tomgirl since being a guy was too hard. Both explanations fit with signs of late-onset gender dysphoria.

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