Classic Sissy Assignment Series 44 – Goodbye, Boy Clothes

Hello my sissy slaves. I am so glad that you’ve begun your training and grooming with me. In a short while, you’re going to find yourself somewhere you’d never thought you’d be. That’s something to think about, and it really turns me on.

You have no right to continue reading until you have read and completed assignment 43, and have been following your rules.

If you break the rules, your punishment is as follows: Set a timer for 30 minutes. Go put a penny on the wall at shoulder height and hold it there with your nose.

Keep your legs straight, and keep your hands above your head and not touching the wall or your head. Keep in this position until you hear the timer go off.

I am serious about my rules, and breaking them will bring humiliating punishments that will not be fun or entertaining.

Now for assignment 44.

Do you have tighty whiteys? Boxer shorts? Every day, until they are gone, I want you to throw away at least one of your most worn and unsexy underclothes. If you have pristine boxers in a bag, you may donate them to a charity.

What do you replace them with? You may replace them with thongs, or with boxer-briefs (with less than 2 inches on the leg).

Naturally, you should have a few pair of panties. Collect more, keeping in mind that I don’t want you buying anything that doesn’t have a cut that holds your extra large clit.

Most panty thongs are out, though you may find some stretchy ones that work.

I expect this assignment to begin today and to continue building over the next few months.

You may not move on to the next assignment until you have thrown out at least 7 pair of ratty underwear or have got rid of all your ratty underwear.

See my Google shopping list for ideas on where to buy, but local retailers include K-mart (for thongs), cheap outlet stores for soft panties, and many places sell boxer briefs (but keep in mind the length requirement).

Now for your rules:

1. If you cum, you must swallow it, all of it, and with a clear voice verbally thank me your master for allowing you this freedom.
2. You must keep your body hair groomed and short. When you go to a hair stylist, inform them to be careful to give you soft and tapered sideburns and to do the same in the back.
3. Gradually get rid of your ugly underwear and boxers, replacing them with panties, thongs, and short boxer briefs.
4. If you break the rules, your punishment is as follows: Set a timer for 30 minutes. Go put a penny on the wall at shoulder height and hold it there with your nose. Keep your legs straight, and keep your hands above your head and not touching the wall or your head. Keep in this position until you hear the timer go off.