It seems a poor choice to me if he has any thoughts of being in general population.
http://www.dailymail.co.uk/...
An Army psychologist has testified that Bradley Manning's private struggle with his gender identity in a hostile workplace put incredible pressure on the soldier.
Capt. Michael Worsley spoke at Manning's sentencing hearing at Fort Meade, near Baltimore on Wednesday, where the former intelligence analyst is expected to deliver a statement later today.
The 25-year-old faces up 90 years in prison for leaking more than 700,000 classified documents to WikiLeaks while working in Iraq in 2010.
Manning, , who was apparently considering transitioning to become female, eventually came out to the therapist and emailed Worsley a photo of himself dressed as a woman, wearing a blonde wig and lipstick.
The photo was attached to a letter titled 'My problem', in which Manning described his problems with gender identity and his hopes that a military career would 'get rid of it'.
I didn't think it would help matters to post the photo.