The headteacher of a leading private girls’ school was listed as a donor to a teacher’s crowdfunding appeal for ‘sex change’ surgery in Thailand.
The English teacher, known as Ms Westwood, works at Headington School in Oxford and travelled to Bangkok in June for what he described as “gender-affirming bottom surgery”.
In an update posted on his GoFundMe page in June, he said surgery was booked for 18 June, followed by five days in hospital and recovery at a nearby hotel before his return flight a month later.
The appeal had raised almost £6,500 towards a £13,400 target to cover surgery and other expenses. Westwood thanked his supporters and explained that he intended to use his savings to cover the remainder.
A £50 donation was listed under the name Caroline Jordan, the name of the school’s headteacher.
The GoFundMe page was taken down this afternoon after [Un]Captured contacted both the school and Westwood for comment.
Explaining his decision to seek surgery, Westwood wrote: “I worked hard at becoming comfortable in the body I was given. But eventually, of course, the dam broke, and I knew that to live the life I want – one where I’m finally at ease in my own body – this surgery had to happen. I could see that my savings might just about cover it. So I allowed myself to imagine what it would be like.”
The £13,400 target included £8,200 for surgery, £3,000 for flights, £1,400 for four weeks’ accommodation, and £800 for post-operative supplies, insurance and contingency costs.
He specified an economy flight to Thailand and a business-class return, explaining that he would need to lie flat while recovering. Surgery fees at a UK hospital would be around £20,000 alone, he added.
Westwood is a former Oxford University English lecturer whose published work includes studies of Edward Lear, nonsense literature and veganism. His writing on veganism has also been cited in academic work exploring veganism, gender and queerness.
According to his GoFundMe page, Westwood began “transitioning” in 2021. Earlier academic work appeared under the name Benjamin Westwood, while later publications use Cassie.
[Un]Captured understands that Westwood taught English at Abingdon School for two terms from January 2023, then joined Headington School in autumn 2024.
The school charges around £28,000 a year in senior day fees, with boarding fees considerably higher.
Several individuals connected to Headington have told [Un]Captured that some parents are concerned about their daughters being taught by a man who identifies as a woman.
One, who asked to remain anonymous, raised concerns about a “Pride Club” run by Westwood, describing its approach as “potentially ideological” and lacking balance.
The source said parents were reluctant to raise concerns because they feared it could negatively affect their daughters’ grades or how they were treated by teachers.
Stephanie Davies-Arai, director of Transgender Trend, said the school’s handling of the situation raises serious safeguarding questions.
“It’s highly likely the fundraiser for a vaginoplasty was known about in school and if the head did contribute it sends a message to pupils that this is a worthy cause,” she said. “When teenage girls are asked to believe that their male teacher is a woman this is the imposition of a political belief system on them.”
She added: “By removing the boundaries between the sexes the school is effectively teaching these girls that being female is just a matter of presentation and clothing. When the whole school leadership is behind the deception it will be difficult for any girl to speak the truth and use correct language to describe reality. These girls are being failed badly by the school’s safeguarding lead.”
Helen Joyce, director of advocacy at human rights charity Sex Matters, said: “In a school environment it’s essential that everyone is clear about what sex everyone else is. The school needs to make it completely clear, including to parents, that this man won’t be regarded as a woman in any situation such as supervising girls overnight on away trips.
“The school leadership must make it clear that staff and students should not be punished in any way for calling a person everyone knows is a man a man, and that there should be no penalties for ‘misgendering’.
“The school must also be very careful not to endorse or even worse glorify surgical interventions for trans-identifying people, as we know that transgender ideation is contagious.”
Jordan previously advocated gender-neutral language in girls’ schools. In June 2016, while president of the Girls’ Schools Association, she told the Sunday Times: “In assemblies instead of saying ‘girls, go to lessons’, staff should consider saying ‘pupils, go to lessons’.”
She added: “My view is that where you can use gender-neutral language about people that is a good thing.”
Headington School was asked to confirm whether its headteacher contributed to the teacher’s sex-change surgery fundraiser, but declined to comment.
A spokesperson said: “We do not comment on individual members of staff, particularly where it relates to protected characteristics or personal data.”
Cassie Westwood was approached for comment.
22 Responses
Having had daughters at Headington, nothing surprises me about Jordan. Not fit to be head of a girls’ school.
When this woman sues you, please publish a link to the crowdfunder. I will gladly donate.
Which woman?
Which woman?
So what? This sounds like a complete non-issue and I fail to see why this is “news”. This is a private individual with no public standing.
A male teacher with power and influence over young and impressionable girls being affirmed as a woman and publicly sponsored for castration and vaginoplasty by his boss and head of the girls’ school he teaches at? I think this is an issue.
This man who works with children who are (in all likelihood) expected to go along with his belief that he is a woman. Even if they realise he is not. Headington is a boarding school so I would be interested to know how they have been and will manage the presence of a man in single-sex spaces.
I was married to a transsexual for 14 years – he never told me the reason for his appalling taunting, culminating in psychological torture – until he was ready to leave me and our two young children. He was castrated 3 years later paying for a private urologist in an NHS hospital.
These men are mad – opinion of Dr Alice Parshall, Medical Director for Mental Health Services in 2008 when I spoke to her about my situation.
Mr Benjamin Westwood should have been sectioned and then helped by psychotherapy to accept his body and not seek to mutilate it. He cannot, he will never “change sex”. Any medical professional telling him otherwise is complicit in medical malpractice, and those directly treating him should be tried for criminal medical negligence.
You are a sick person, harassing someone for merely existing. Take a long look in the mirror and consider how your life choices led you to be such an awful, awful person.
He’s not “merely existing” though, is he? He’s inflicting his crossdressing sexual fetish on girl children, at best, and, at worst, sexually abusing them. You are an “awful, awful” pee-dough for condoning it, Bob.
I find it horrifying that a man with a sexual fetish (autogynephilia) is allowed any where near our precious daughters. This is a safeguarding nightmare, not only for the vulnerable girls, but for this man’s female colleagues. No doubt he will be using their facilities, and no girl or woman can possibly raise any objections in the current climate.
Children are vulnerable to bad ideas, especially if such ideas are promoted in their school. No child should be exposed to a sex-pretender in their classroom or school. If a man wants to pretend to be a woman he needs to find a job where his immersive role play is not having an impact on children. There are many careers and professions available which would not affect children and young adults, it is not unreasonable to require a sex-pretender to choose one of those and leave our children free to grow up safely without developmental glitches being thrown into the mechanism.
I’d pull my daughter out of there immediately, I don’t expect her to be gaslit at school, or be expected to be part of a man’s fetish.
Most sane people are fully behind this viewpoint, and would have the same concerns. Ideological nonsense shouldn’t be foisted upon impressionable school kids. I truly hope the girls are not being cajoled and forced into lying, and I hope the parents find the courage to speak up about this.
This teacher should be raising red flags, not funds.
Gosh this really worries me. There’s a man with a clear fetish pretending to be a woman, in a girls’ boarding school. He could be left in charge of girls while changing or at night. The safeguarding issues are through the roof. Not to mention the indoctrination that you can choose your sex. It’s a lie. Sex is not a choice.
Maybe there should be a ban on ALL transgender people in ANY role that brings them into contact with children. I’m getting to the point that they are all a risk.
A teacher bringing his fetish into the classroom. Red flags all round. What has happened to child safeguarding? Why are males allowed to cosplay and use children as part of their cosplaying? Because cosplay is all it is. He will never be a woman.
What safeguarding rules are being abused? And why did the head teacher think it a good idea to support this? What else is happening at this school? If I had a daughter there I’d be extremely worried about how safeguarding rules are being applied.
The safeguarding (or lack of) implications at the school are very concerning. Does Cassie have access to the girls’ toilets, changing rooms? Does Cassie go on school trips as a ‘woman’ adult in charge? I’d be incredibly worried if I had a daughter at the school
If true, how will girls and staff at the school feel able to express any concerns (eg about him using female toilets or sharing accommodation on field trips). She could have donated anonymously. It also sends a terrible message that surgery is an appropriate response to an emotional/ psychological situation. Would she fund a member of staff to have a nose job because they think they’re ugly? And people should beware – maybe in future this man will realise he has made a terrible mistake and sue those who funded him.
A school, teachers and female pupils involved in and participating in this man’s fetish but also funding it. I would be very interested to know if he was employed as a male teacher originally (He still is of course).
Often they groom the staff around them before they start having mini breakdowns about not being their real selves, then drip, drip suddenly they are a stunning and brave Ms.
We need to implement laws that mean people like this are not allowed to be in child facing roles, moved into admin as soon as signs start they are in a range of mentally ill to dangerous…that T Shirt seems to suggest an extreem end of this spectrum. The fact they are unable to keep this in their private life shows that participation of others is part of their perversion.
Any school which employs asle teacher who claims to be a woman is telling girls they have no right to boundaries and being female is just a feeling in a man’s head.
Keeping Children Safe in Education, statutory safeguarding for schools, has always said no child should be used to validate anyone or silenced – both count as emotional abuse.
The headteacher knows this and chose to ignore it.
Interesting role modelling…? 🤔