If you work with female colleagues or have some female friends then this task is for you.

Choose a colleague who is wearing make up. If that gives you a choice, choose the look you most admire. Engage the person in polite conversation. Study her make up. She may or may not notice you staring. At some point in the conversation, you must compliment her on her make up. This is not something a real man would ever do, but then you aren’t a real man, are you, sissy?

Suitable statements might be –

“I like how you’ve done your eyes”

or “that colour lipstick really suits you”.

You could preceed this with

“I couldn’t help noticing…”

or “you look great today,”

but you need to be very careful to not sound like you’re hitting on them. You should try to make it sound like the sort of compliment a woman would pass. You’re dying to talk to a woman about make up & clothes, as her girlfriend, aren’t you, sissy? This could be a start.

If you get treated warmly, continue. Give her the impression you are interested in women’s clothes and make up. Hardly acting is it, sissy? There isn’t a day goes by you don’t look at a woman and imagine yourself wearing something she has on. Comment on her hosiery or shoes – many women get obsessed with shoes and would love a man to notice what they’re wearing.

“That skirt (blouse) is lovely. Where did you get it?” is an interesting question to ask a woman. Just beware of sounding like you are eyeing them as a potential partner (unless you want that!) – you are purely aiming for a ‘woman to woman’ conversation about your lifelong obsession.

See where it leads, sissy. That is your challenge.

I’ll do it