Sissy Humiliation Assignments Series 28 – Makeup Compliments

If you work with female colleagues or have female friends, this task is tailor-made for you, sissy. It’s time to blur the line between admiration and envy.

Choose a female colleague or friend who is clearly wearing make up. If you have several options, pick the one whose look you most adore — the one who makes your heart flutter with the way her eyes shimmer, or how her lips gleam seductively.

Engage her in polite conversation, as naturally as you can. As you chat, study her make up carefully: the blending of her eyeshadow, the precise flick of her eyeliner, the shade of her lipstick, the evenness of her foundation. You may feel nervous, but remember, you crave this.

During the conversation, you must compliment her make up. Not in a clumsy, awkward way like a man hitting on her, but softly, the way a girlfriend would. Your goal is to sound like a woman admiring another woman’s style.

Examples of what to say:

• “I couldn’t help noticing how perfectly you’ve done your eyes today.”
• “That lipstick colour really suits you, it looks amazing.”
• “Your makeup looks flawless, what products do you use?”

Consider starting with a warm, casual lead-in:

• “You look great today…”
• “I just had to say…”

But be careful not to sound like you’re flirting or ogling — you’re trying to build a woman-to-woman rapport,not a creepy come-on. This is a chance to start the kind of conversation you’ve dreamed of your whole life: talking about make up, clothes, and style just like a girlfriend would.

If she responds warmly, continue the conversation. Let her see your interest in make up and fashion — you’ll barely be acting, sissy, because deep down you know you’ve always wanted this.

Ask where she bought her blouse, skirt, or shoes. Many women love talking about fashion, especially if someone notices the little details. A question like:

• “That blouse is gorgeous, where did you find it?”
• can open doors.

Imagine the thrill of having a female friend who sees you as one of the girls, someone she can share beauty tips and shopping finds with. That’s what you long for, isn’t it, sissy?

See where it leads. You might find yourself invited to girl talk, shopping trips, or even make up sessions.