By Nathalie Bonney @nathaliebonney

A 21-year-old trans woman is finally able to have gender reassignment surgery, thanks to her 61-year-old sugar daddy boyfriend - who is also her ex-fiancé

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Videographer / director: Ruaridh Connellan
Producer: Nathalie Bonney, Ruby Coote
Editor: Jack Stevens

Anastasia's 'sugar daddy' will pay for her gender reassignment surgery

Having dated for just over a year, Anastasia and her partner broke off their engagement at the start of 2017 but still date and are on such good terms he is paying for her surgery.

Anastasia said: “Before I met him, and before I began transitioning, I was just miserable, very unhappy with who I was. I hated my body. And even now, just before my surgery, I love myself so much more than I used to.”

“He is paying for my transitional surgeries, which I’m extraordinarily grateful for.”

In a relationship with a man 40 years older than her and who used to be her fiancé, Anastasia’s love life is more than a little unconventional. The couple met through sugar daddy dating website seekingarrangement.com and are yet to consummate their relationship - in fact they have no intention of doing so. In spite of their significant age gap Anastasia says she is fond of her high-flier lawyer ‘sugar daddy’ (who doesn’t wish to be identified) - but dislikes the label.

She said: “I would not describe him as a sugar daddy. I hate using that term. I hate saying sugar daddy, sugar baby. I don’t see him as that.

From as young as five years old Anastasia was unhappy with her body

“I just see him as someone I love very much. He loves me very much. I mean, yes he gives me money, yes he takes care of me, yes he protects me and yes he is helping me to start this brand new life that I should have been born into but unfortunately was not born into.”

Together, the vaginaplasty, breast augmentation and facial feminisation will cost approximately $60,000 but Anastasia insists the relationship isn’t about money alone.

She said: “I have always made it very, very clear that I am not here for money, I am not here to be spoiled, I am not here to be taken on shopping trips, I am not here to be given allowances, I am here specifically for my surgeries, that’s it you know.

“I am not money hungry, I am not a grabber in any way. I am not spoilt, I don’t want to be spoiled. I have no time for that. I just want someone to help me for my procedures because my insurance doesn’t cover them.”

Their unconventional relationship means the pair haven’t slept together although Anastasia will disclose that they do have what she describes as, ‘a sexual relationship.’

Growing up in Texas, Anastasia admits she was bullied as a boy and deeply unhappy all her childhood
Anastasia has already done some modelling work and hopes after her surgery to do more

She says: “We will lay down and cuddle but nothing overtly sexual.”

“I would definitely see a difference from being an escort or prostitute because I’m not on a street corner, you know, it’s not my job. It’s not something I do every single day. It’s really just one man whom I have known for a very long time, who is very good to me.”

As well as her sugaring commitments, Anastasia currently works in real estate –but no one at her work is even aware she is transgender.

She said: “All of my friends know [I’m transgender] but my co-workers don’t. I don’t think it’s any of their business. If someone asks me, ‘Are you transgender?’, sure I will say yes but it’s none of their business.”

She has also walked in several catwalk shows and believes her gender reassignment surgery will enable her to find more work.

As a teenager Anastasia questioned if she was gay before realising she was trans gender

She said: “I’ve done some modelling since I was 17 including catwalk and New York Fashion Week. After my surgery I hope I can do more.

“The modelling industry can be very hostile to transgender models – they would say, ‘We just don’t know how to market you’. It was very hard and stressful.”

Anastasia grew up as a boy in Texas with her family. From as early as five she admits that things about her life and her body felt abnormal to her – but she couldn’t work out it what was until she was 17.

She explained: “I first realised I was born in the wrong body when I was probably around 5-years-old. I just looked down at my body and I didn’t look normal.

“I would just sort of not understand why it was not developing more like my mother and it just didn’t feel right. It didn’t feel normal and I remember being like 7, 8, 9, 10 years old and just always looking in the mirror and being very disgusted with what I saw.

Dating a man 40 years her senior, Anastasia says she 'loves very much' her sugar daddy
Since moving to New York Anastasia has a new-found confidence

‘I remember asking my mom like, ‘Mom why am I boy? Why am I not a girl?’”

Initially, Anastasia thought of herself as gay but says she was never attracted to gay men and being intimate with them never felt right.

Moving to New York aged 17 to pursue a career in modelling she finally realised she was a girl trapped in a boy’s body - something Anastasia’s family had come to terms with before she’d even fully accepted it herself.

She said: “Growing up I was a boy who liked boys but I wasn’t attracted to gay men – I eventually realised I was a girl trapped in a boy’s body.

“I grew up in-in Texas where everyone is so right wing and conservative. The bullying was terrible growing up. I was bullied day in and day out middle school, high school, elementary school. I had almost no friends growing up. It was very, very hard.

Anastasia's reassignment surgery is planned for June 2017

“It deeply affected me mentally for a long time not being true to myself and it wasn’t until I moved to New York that I embraced who I was.”

Anastasia believes her surgery – thanks to her sugar daddy - is the next step on her journey to becoming her true self.

She said: “The day I realized that I was a woman I just felt like all these chains were lifted off of me.

“For me surgery is like finally closing the book on a very dark nightmare.

“After I have my surgery and I am recovered I will finally be born again.”