ashleyanne | 03.30.2019 | Reports - Getting Real

This sissy already has begun to execute on a resolution for 2019 that is inspired by Madame Stewart’s kind yet firm guidance and encouragement. This sissy believes that the resolution will bring nods from the Sissify Superiors (even if it will not necessarily do so for other Superiors in this sissy’s life) and matches the next steps that are necessary for this sissy to continue her development.

This sissy resolves to seeing the light of day in the public eye every month in 2019; this sissy is starting with a reasonable resolution of being outside, and by “outside” this sissy means in public, for at least a couple of hours every month. While this may not seem like a huge ask to some sissies, this sissy struggles mightily with being out in the public eye. Whether it is a walk in the park, a public makeup lesson/makeover, a subway ride, a meal, or a drink, this sissy is committing to being out in public every month.

For the month of January, this sissy took two trips outside from her apartment into the light of day with a couple of walks in a neighborhood park. The attached photos were taken outside while on the January walks. This sissy got dressed and donned her winter coat and scarf. Under her coat, this sissy wore a pink exercise shirt, a white jog bra, a pair of grey trainers, and white exercise leggings.

ashleyanneThis sissy started outside with long hair but quickly became frustrated with the hair blowing into her face and so she walked back indoors and changed to a shorter wig before going back outside for another hour in the daylight and in the public eye. This sissy needs to work on making appropriate eye contact and perhaps wearing her contacts out so that this sissy can be comfortable with the eye contact. To this sissy, getting comfortable with the looks of others is the first step toward interacting with others in public.

This sissy also has begun planning her trip out into public for February, which is but two weeks away. This sissy is planning on visiting a MAC Cosmetics Studio for a makeup lesson/application. The Studio is 1.8 miles from this sissy’s apartment (a 40 minute walk through a very busy city). This sissy is trying to decide whether this sissy will travel to the studio en femme or whether she will just travel back to her apartment en femme. Either way, this sissy is planning on being outside in February and then will begin to identify opportunities for March.


  1. It makes this sissy very happy to ready this report! ashleyanne, your hair and makeup skills are more than 100% presentable, gorgeous! lila hopes your experience has been similar, and that you find going out en femme to be more addictive than any narcotic imaginable.

  2. dear sissy ashley, you are brave in taking this big step, going outside. you are an inspiration to all the sissies on this site. your perseverance and hard work demonstrates what is possible, you are as beautiful on the inside as you are externally.

  3. This sissy loves your pictures ashleyanne! Sooo pretty (as usual)! So happy for your progress as well sweetie…every small progressive step in high-heels is an important step! You are an inspiration to so many of us! Can’t wait to read of your future adventures into the world while embracing your femininity (hugs)!

Something to share sweetie?