John Pilley, currently known as Jane Anne, is in Holloway women’s jail in North London. The prisoner made legal history in 1999 when he became the first inmate in England and Wales to be granted permission for a sex change operation. He is understood to have undergone the gender reassignment operation on the NHS in 2001 at an estimated cost of £15,000.

Pilley, 54, was moved from Gartree Prison, in Leicestershire, where he was serving life for attempted murder and kidnapping a female taxi driver, to Holloway, but after living in the female jail has decided to become a man again. He is waiting to have his second operation on the NHS, then will be transferred to a male prison.

Christine Burns, of Press for Change, a pressure group for transsexual rights, said: “Although it is not unheard of, it is very rare indeed for people to have regrets and want to change back.” The surgery would be similar to that used for female-to-male transsexuals, she said.

Pilley underwent seven years of hormone treatment, after which he won the right to have a sex change operation. He was initially refused permission by the Prison Service to have the operation, but the service dropped its opposition after taking legal advice. He was allowed to wear women’s clothing in his cell at night but wore men’s clothes during the day. The Prison Service has refused to comment on the case.

Another prisoner who underwent a sex change was David Cross, who changed his name to Kelly Denise. Cross, 39, was jailed in 1992 after an armed raid on a Post Office. It later emerged that he had been trying to steal money to fund a sex change. Cross was allowed to begin female hormone treatment on the NHS in 1993, travelling once a week from Parkhurst Prison, on the Isle of Wight, to Charing Cross Hospital, in London.

Many people awaiting sex- change operations take Androcur, a hormone that suppresses production of testosterone but can cause liver damage with prolonged use.

Figures show that in 2001-02, 89 operations were carried out for male to female reassignment, but no similar surgery for female to male gender reassignment were recorded.

Research published last year suggested that there was no conclusive evidence that sex- change operations improved the lives of transsexuals.

It is estimated that there are about 5,000 people who have had the surgery, and that about 400 operations are carried out annually, on the NHS and privately.

Brian Caton, of the Prison Officers’ Association, said that it was a matter for the individual, but that prisoners received the same treatment as anyone else on the NHS.

Explore UK News

• Crime News

• Education News

• Health News

• Science News

• Scotland News

Times Recommends

• Olympic-size television coming to your town
• Mosley opens new front in battle for privacy
• Decorator fined for smoking in van