The Massachusetts Treatment Center, where Jessica Anne Guillotte is incarcerated, is a medium security facility for male sex offenders in Bridgewater, Mass. Courtesy of the Massachusetts Department of Correction.

Jessica Anne Guillotte

JJessica Anne Guillotte realized very early on that she felt like a girl, not a boy. She never liked to play with boy’s toys and preferred girls’ toys and clothes. When she was 5 years old, Guillotte, who did not want to provide her given boy name, would often sneak a pair of her sister’s panties and wear them to school.

In kindergarten, she spent recess inside the classroom with a female teacher’s aide rather than with the rest of her class outside because of her cerebral palsy. One day, the aide asked if she wanted to play catch and took her inside a small hallway. After a few tosses, she threw the ball hard at Guillotte’s genitals. Claiming it was an accident, the aide started rubbing the child over her pants.

A couple of weeks later, the teacher’s aide asked Guillotte to play catch again. She eventually gave in and this time, the aide locked the doors and pulled the shades down. She threw the ball once more, and rushed to pull Guillotte’s pants and underwear down when the child reacted to the pain. She then molested and anally raped Guillotte with a plastic tube.

At the time, Guillotte believed the teacher’s aide was punishing her for wearing girl’s underwear because she said, “This is what happens to nasty little boys.”

Over the last year, Guillotte and other transgender inmates in Massachusetts have written a series of letters describing their gender identity journey as part of a Northeastern University School of Journalism project. Guillotte has been the subject of abuse throughout her life and was only recently diagnosed with gender dysphoria. Her requests for medical treatment have all been denied so far.


Jessica Anne Guillotte has been incarcerated for 13 years at the Massachusetts Treatment Center. She is serving a sentence of one day to life for sexual assault on a minor and failing to register as a sex offender. Courtesy of Jessica Anne Guillotte.

Born on Oct. 14, 1966, Guillotte lived on a farm in Stanford, Vermont, with her mother and father, older sister Cheryl, and younger sisters Charlene and Vivian.

She remembers sitting on Cheryl’s bed, admiring all her pretty clothes. One day, she asked if she could try on a light pink flowing ruffled dress. Cheryl gave her a strange look but put it on her.

“I felt so right, like it was the most natural thing in the world for me to be wearing a dress, I felt so special,” Guillotte said in a letter. “So alive and excited, like I was being seen, seen as the girl that I already knew myself to be.”

The family moved to Adams, Massachusetts, where Guillotte had a female babysitter that liked to dress her up in little girl’s clothing and put her hair up in pigtails. One day while at her house, the babysitter dressed her up as usual and propped her up on the kitchen table.

Guillotte, who was 6 at the time, said two men walked into the kitchen and handed the babysitter money. One of the men came over to Guillotte, ran his fingers through her pigtails and said, “You’re a pretty girl.” The babysitter then walked her into the living room, where the two men sat down.

“Suddenly, the man who had touched my pigtails and face took me by the hand, walked me in front of him and forced me to kneel down on some type of couch pillow, then he unzipped his pants and told me to suck on his lollypop, that I would like it, then he forced my mouth on to his penis,” Guillotte said in a letter.

Shortly after, Guillotte and her family moved again to Johnston, Rhode Island, where they lived with their cousins, aunt and uncle. She never told anyone about the incident.


Around 1974, when she and her family moved one last time to Providence, Rhode Island, Guillotte started secretly dressing up like a girl every chance she got. At 11 years old, she got a job cleaning a yard and saved $400 to buy bras, panties, skirts, heels, dresses, purses and makeup at Kmart.

Guillotte, who said she had endured systematic and brutal attacks of sexual abuse from when she was 5 years old until her incarceration, said she was conditioned to believe early on that she had done something wrong to deserve these assaults. She never told anyone in her family about her experiences, fearing they would discover her secret.

As a result, from the ages of 13 to 16, Guillotte led two lives. Around those who knew her, she pretended to be a boy. When her family was not around, she walked the streets of Providence as a girl. She became angry and ashamed of her cross-dressing.

“I thought that I was sick in the head, that there was something mentally wrong with me,” Guillotte wrote. “Time and time again, I would dress up, punish myself and do it all over again.”

At times, she would even try to convince herself that she could stop these feelings and live as a man. She had relationships with women and got married to a woman, in an effort to appear normal to the outside world. However, she was unhappy.


In 1996, Guillotte, 30, was accused of raping a 6-year-old boy while babysitting. In 2003, she was accused of annoying and accosting a member of the opposite sex and failing to register as a sex offender, for which she is currently serving a sentence of one day to life at the Massachusetts Treatment Center in Bridgewater. Her only avenue for release is to be declared no longer sexually dangerous.

A decade into her incarceration, she contacted mental health clinicians and explained she had been struggling for a long time with the fact that she is a woman trapped in a man’s body. After finally mustering the courage to come forward, she said she was met with disbelief and skepticism.

“Even after I answered all of their questions truthfully, even after I jumped through all of their hoops, even after I freely let them talk to my three sisters about my being female, they didn’t and don’t believe me,” Guillotte wrote in a letter, “and yet, they gave me the diagnosis of […] gender dysphoria.”

Guillotte requested hormone replacement therapy, but her clinician wrote in his report that he felt she became transgender as a defense tactic to help her get released.

“Over and over again, I’ve given informed consent to be put on female hormones. Over and over again, I’ve been denied access,” she said in a letter. “So, here I sit suffering mentally, forced to stay trapped in the male form I’m in at the moment.”