Sidney Gray
NameSidney Gray
Place of BirthUnited States
Sexual OrientationPansexual
Sissy Since2009

Sidney Gray is a renowned sissy porn actress, adult oriented content creator, sissy teachings spreader and writer from the United States of America. Even tho she considers herself a sissy, she is since year 2019 in the process of becoming a trans via taking estrogen injections.

She has worked with famous porn actor ChristianXXX on a Becoming Femme photoshoot and porn video. Simultaneously she has created adult oriented content for her Patreon and Manyvids profiles. Her favourite kind of shoots involve her to be in the submissive position with males or doing solo Virtual Reality headset rituals while inhaling poppers or other drugs such as cocaine to enhance her horniness.

Sydney is also a popper (an amyl nitrite inhalant commonly used by gay, sissy and trans people to have a more pleasurable experience during intercourse or sexual situations) enthusiast, she encourage sissies to remain chaste to improve their sexuality and to take poppers while doing sissy hypnosis sessions in order to brainwash their masculine thoughts replacing them with sissy feelings and emotions.


Youngest of a family with six siblings, Sidney was raised at the heart of America by her mother. Since an early age she used to watch porn at VHS tapes that were on her older brothers room’. She recalls watching all this content out of curiosity instead of doing it for the pleasure of masturbation.

Around the age of 13, Sidney had her first crossdressing episodes stealing her teenager sister underwear and clothing. After seeing herself in a feminine manner she couldn’t manage the contradictory feelings and the pleasure of it and started to masturbate compulsively ending it in her first orgasm. She calls this lifechanging experience her destiny call into sissification.

This masturbation to crossdressing attitude continued during her entire adolescence first wearing her sister clothing and after that progressing to her mother lingerie at the house toilet while her brothers were playing videogames in another room.

During the last years of her teenager years Sidney started reading the famous blog Mandatory Feminization that promted her to change her views on crossdressing marking this as her first encounter with the Sissy lifestyle. Around the same time she adopted the name “Lindsay Gray” on her sissy social media while she hid al this kind of practices to her girlfriend at the time. She has confessed also that she used to play the part of a normal boy at High School, having penetrative sex with women while at home she used to dress as a sissy and being a bottom in front of the PC screen.

Around 2017 Sidney’s girlfriend broke up with her after she found out about her crossdressing images and videos. That traumatic experience involved this girl exposing her to her whole family. After half her family members called her “a faggot”, she started having suicidal and depressing episodes. During this time Sidney started experimenting with men, working on the streets and peep shows as a prostitute with clients she previously met on Grindr and other homosexual sites.

Photo of Sydney’s first sex club act on June 2018.

But that sad experience didn’t made Sidney quit. She moved out from her family home and rented an apartment at El Paso, Texas in order to carry on with her sissy urges. Around the ending of 2017 and beginning of 2018 she started to upload posts on Tumblr and videos/photos on Xhamster chronicling her boi to sissy transition.

In the content she uploads we can see her engaging in VR headset hypnosis sessions while taking inhalant drug Poppers. She considers this a good way to become engaged on this world and to become fearless in order to break free from the chains of pseudomasculinity.

On June 16, 2018, Sidney started her estrogen injections after encouraging by a fellow sissy friend that helped her into the hypnosis and poppers circle of sissiness. Around the same time she started to sporadically act on sex clubs and engaging in sex with men, destroying her heterosexuality and giving birth to her bottom effeminate new role in sex.

A still of Sidney’s first porn shoot with ChristianXXX

During 2018 Sidney went into 90 day periods of chastity in order to feminize herself up, to reduce her clitoris size and to become a porn star. Something she achieved on April of that year shooting an scene with experienced porn actor ChristianXXX. During the following months she would start her Manyvids and Patreon sites to earn money from pornographic content of her own.

It can be noticed tho that while she is a popper enthusiast, Sidney also started to be in a period of sobriety during the end of 2018 and beginning of 2019. It is not clear if this sobriety is around a possible alcohol engaging or to other drug use (it is known that she has used cocaine along with poppers on her most sexiest videos).

Nevertheless she is seen using poppers on her recent Xhamster videos and keeps herself in permanent chastity in order to become more submissive and effeminate for real men that have sexual intercourse with her. Currently she lives in New Mexico and does videos for ManyVids, and is considered by other sissies and crossdressers as a rolemodel of what a real sissy girl should be. It is expected that she will go on with efforts to do more porn movies in the next years and improve her transition into a female.

Publications & Educational Texts



Recent Comments
    Latest Posts
    All comments.