Sissy Moms

Sissy Moms is a brand new pinup and video project for mature (30+) trans femmes and crossdressers. We are located in Chicago, IL, USA and are looking for femme models, male performers, makeup artists and those with an interest in retro decor.

Our Mission

Opportunities for mature girls are scarce. Transformation artists, wardrobe consultants, professional photographers and set designers can be very expensive, and finding all of these talents under one umbrella has been impossible – until now.  This project will provide a platform for mature girls who are ready to raise the bar on expectations, and who are open to doing so in a fun, kitschy style and SMILFy theme.

Extra consideration will be given to those who are also interested in mentoring and/or performing alongside younger, less experienced girls.  After all, what good is being a Mom if you don’t have a young aspiring sissy to help educate?  

We are beginning with models in Chicago and expanding nationally and worldwide.  Trans femmes and experienced crossdressers are preferred, but we are also interested in interviewing select inexperienced people who would be interested in being feminized by one of our makeup and transformation artists.

Models will begin with photo shoots, either safe-for-work or NSFW, depending on their comfort level. Photos are not monetized, so shoots will be unpaid sessions – at least initially. Models who wish to earn extra income may progress to video productions, which will be monetized/paid shoots.

We are also looking for male performers who are interested in participating in video productions, as well as makeup artists and anyone who has an interest in vintage decor. If you have a location with interesting decor (50s, 60s, 70s, 80s, deco, etc) and would like to host a session, we would like to hear from you.

We encourage everyone who is interested to fill out the appropriate application form. Help make Sissy Moms a household name!

Application Forms

If you would like to be considered for this project, fill out the appropriate application form.

Femme Models

Models 30 and up!

Male Performers

18 years and over

HostS & Makeup

Makeup & Hosts