Sissy Humiliation Assignments Series 16 – Kissed b y Courage

Next time you catch yourself admiring a woman’s lipstick, don’t just sit there drooling in silence — speak up, sissy.

Here’s exactly what you must do:

Picture this: you’re at work, chatting casually with a female colleague at her desk. Your eyes are irresistibly drawn to the glossy shimmer of her lips as she talks.

You imagine how that luscious colour would look on your own lips.

Muster every scrap of your courage and say:

“I hope you don’t mind me saying, but I really love the lipstick you’re wearing today.”

She’ll probably smile or blush, surprised that a “man” noticed. That’s your cue:

“What shade is it?”

Watch how her eyes light up with curiosity. She’ll think it’s odd — because what real man would ask something like that? That’s exactly why you’re doing it.

If she has the lipstick with her, ask boldly but politely if you can try it on. Say something like:

“I know this might sound strange, but I’ve always wondered what it’s like to wear lipstick every day. Would you… let me try yours?”

If she agrees — and you’ll be surprised how many women will, let her apply it for you.

She’ll probably giggle as she holds your chin and tells you to stretch your lips over your teeth. You’ll feel her soft touch, the intoxicating scent of the lipstick, the warm, waxy drag across your lips.

Then she’ll hand you a mirror.

You’ll see your feminine, shiny red lips on your male face. The humiliation will be exquisite. The excitement, undeniable. If she’s really into it, she might even hand you the lipstick to keep, or tease you about refreshing it after lunch. Imagine the thrill as she checks your lips later, expecting to see them perfectly painted.

Important: If she refuses, do NOT push her or make her uncomfortable. Thank her sweetly for her time — but remember your goal: you will do this with the next opportunity.