Classic Sissy Assignment 9 - Sissy Lipstick

For soft girls, femboys, crossdressers, and feminine dreamers

Sissy Lipstick Cock Sucking
Assignment

Your ninth file from the Classic Archive moves through preparation, a bold lipstick makeover, mirror practice, documentation, and final submission.

First Direction

Second Direction

Now, get out the sluttiest lipstick you have, your biggest rubber cock, and a camera.
These are essential for your next steps, so make sure they’re ready.

Third Direction

Find a makeup tutorial that shows how to apply makeup in a slutty, whorish way.
Watch it carefully, and then apply your lipstick just like the tutorial instructed.
The bolder, the better—make sure your lips are looking irresistibly sexy.

Fourth Direction

Stand in front of the mirror and take a good, long look at yourself.
Admire the way you look, and out loud, tell yourself exactly what you are: a cock-sucking, cum-loving fag.
Say it with pride, as you accept your sissy identity.

Fifth Direction

Take your rubber cock and suck it in front of the mirror for at least 20 minutes.
Make sure to leave a noticeable lipstick ring around it.
Watch closely at how you’re performing, and think about how you can improve your technique to be even more obedient and slutty.

Sixth Direction

Once you’re done, take a picture of your mouth around the cock, showing off the lipstick ring you left behind.
Make sure the photo is clear, showing off your submission and how well you performed the assignment.

Final Direction

Email your pictures to your Mistress, along with a report on how you think you could be a better sissy.
Be honest about how you felt and what you think you could improve for your next assignment.
I’ll be looking forward to reading your reflections.

Go ahead, sissy. Complete the task with pride. ✨

File 009 · Photo + Report Required

Next Classic File

Continue the archive one file at a time and carry your lipstick confidence into the next classic assignment.