Xpressions today is a combination of two other organizations; The Monarch Social Club, known at 'Monarch' and the original Xpressions organization, as it was founded. Debbie Pyke, of Fantasyland in Owen Sound, initially founded the Monarch organization around 1985. Fantasyland is a company similar to Wildside, who supply & support the cross-dressing community. Debbie Pyke's initial thoughts in starting the Monarch Social Club, was to provide her clients with a social environment, wherein they could meet others with a common interest & have fun together. In 1987, Wilamina started a Toronto Chapter of Monarch, which became a separate member's-driven club.

Like Fantasyland, 'Take a Walk on the Wildside' also had started a supporting & social organization, which they called the 'Canadian Crossdressers Club'. It was from this base, that the original 'Xpressions' organization began in 1995, founded by Janet, Victoria, Yolanda, Laura & Cynthia.

In 1996, four individuals, Wilimina & Donna from Monarch & Pamela & Cynthia from the original Xpressions, worked diligently to negotiate the terms and conditions of merging the Monarch Social Club & the original Xpressions organization. The negotiations were successful & in August of 1996 & a new organization, which was initially called 'Monarch-Xpressions', was formed. This organization operated for about one year with the name 'Monarch-Xpressions', at which time the 'Board of Directors' voted to change the name to just 'Xpressions', as it is today. Through the years, the Xpressions of today, has become a full Transgendered social and support organization, which has North American recognition. Xpressions has become a major voice with the Ontario Human Rights organization & we are held in high esteem by I.F.G.E. and all other Transgendered clubs & groups, in both Canada and the United States.

As a member of Xpressions, 'BE PROUD!'