Life, Liberty and the Pursuit of Femininity

1950’s New England with the short drive from Boston to a small industrial city to the north Portland. When you travel Route 95 in 1950’s the lanes dropped to 4 and the bustling traffic with big finned Ford’s and Chevy’s .ruled the road. Perhaps you see a I like Ike sign off to the side of the road. AM radio playing Elvis and Little Richard. The Korean war was just ending and GI homes were being built along highway to budding small towns into the suburbs. Ted Williams was belting mammoth home runs and Bull Russell was key into building Boston’s first dynasty. Senator Joe McCarthy was beginning the Anti Red Crusade making his list from everyone in government and Hollywood of being communist. In the fishing port city of Portland Maine is where our story begins.

Diane was born into your average family and although she was born with the name Jimmy deep inside from a very early age she was different. There was always a part of her she had to keep concealed but as each passing year she knew what her destiny would be. By age 14 Diane was wearing her sisters clothes and the two of them loved to try on new things. The schools repeatedly tried to request she dress as a boy and after many attempts her parents relented. In High School Diane graduated and as the Police action on Vietnam progressed she thought of joining the Navy . In someway she attempted to contradict her inner self and be what the world thought she be. She left the Navy after being unable to pass the Naval swim tests and married a lesbian woman but the piece of the puzzle didn’t fit After her wife gave birth she soon fled as being a mother was to much for her. Diane was alone and with a child in tow the instincts that are inside every woman took over. She was a single mother providing for her child like any mother would do. She met a man whom she claims was gay and again she tried to find the right pieces to put together. Her biggest dilemma wasn’t that she was gay but the spirit of a woman always guided her and that possibility was just to much for her husband.

In 1965 Diane and another person named Stephanie a black transgendered person that was very similar in circumstances to her own. They had meetings at the Harvard Medical School with a young surgeon named Doctor Francis Woldort. There had been many that applied for this opportunity but Stephanie and Diane were the final 2 selected. The work was ground breaking and the Harvard Gender Identity Clinic was one of the first In the United States. Diane expressed a freedom she had been looking for all her life. She was working at a local dinner in back of the old Filenes department store in downtown Boston.

In 1960’s Boston the theatre district was booming along Boylston and Washington Streets. The area would be divided the off Broadway plays and musicals would inhabit Boylston St and Dance Clubs, Gay bars and strip clubs would form along Washington St and would become known as the Combat Zone. Single motherhood was still not the norm even in a metropolis like Boston working nights Diane would be a headliner at the Piccadilly a local strip club. Diane refused to allow them to reveal her identity and after a few years went on tour. She was never much interested in prostitution or escorting. The one thing that was paramount in her life was her daughter Deborah and providing her with a home and a education.
After Deborah was finished with college Diane decided to have a talk with her. Diane yielded to her history and in a state of shock she stormed out the door. Several hours had passed and when she returned the only demand was that this conversation never took place again. Diane tried to rekindle her daughters relationship with her natural mother but there was very little interest on either side. The one constant in Diane’s life was being a mother and grandmother.
In the Late 70s Dianne finally found love with a local roofer in Boston. Her daughter was settled and married and soon would give birth to her grandchildren. After much consideration Diane gave her husband her story and with out a flinch they were able to move on with what she called a whirlwind romance.
Diane enjoyed life as a grandmother her love for them was always provided her comfort. Diane had never been political or was much of a activist. She was more or less led to be a power of example to other transgendered woman . She would be quick to point out to other woman of the perils of street life and prostitution. She voiced her concern but deep down she never felt she was making any kind of statement. Her inner self always prevailed and she knew her path from of a very early age. Diane embraced the woman inside of her and her journey she felt was chosen for her. Many woman that have followed Diane’s path in life have felt many oppositions and obstacles in their way. She fondly embraces her childhood and is so grateful to her family. She feels that things were so much more simpler in the 50s when she began her transition and people just didn’t come out or if they did it was so rare that it was easily dismissed. Her journey has been met with some heartache and pain but through it all her life was worth living. Diane became divorced in the mid 90s and had remarried again but soon after her husband had passed away. She moved to Florida as many widows do to live out her life. Retirement lifestyle didn’t quit suit her and after being diagnosed with cancer she settle in to a small town in central Pennsylvania. It was such a privilege to have interviewed Diane it is so rare in life to meet someone so at peace with them selves and their life. She has no regrets and when she was sending her her photos I could feel her smile. Five decades behind her and a retiree in her 60s she only is looking forward to the next gift awaiting her around the next corner.