Sissy Instructions

Dear sissy,

I trust you are preparing yourself well for our session next week. This session will be your final plunge into the realm of sissyhood. Thus far, you have simply dabbled in it, all the while essentially staying a man. All that will change starting from this session.

Starting now, from the moment you finish reading this letter, one thing will change forever. You will never again be without a reminder of sissyhood on your body. At any given time, either your nails will be painted or you will be wearing panties or you will be plugged. Always, awake or asleep, you will know you are a sissy.

Following is how I'd like you to be attired tomorrow. Be sure to follow these instructions exactly, sissy, or you will regret it. No shortcuts either, trust me, I will know. From the inside out then:

1) Chastity device. You will start by putting and locking this on, to get you into the right frame of mind.

2) Butt plug, at least 4 inches. A plugged sissy is a happy sissy.

3) Panties. I'm sure you already have plenty, you dirty little slut, but you will be buying another pair. The colour must be pink. Acceptable styles are bikini, hip-hugger or tanga panties. Try and impress me, my dear.

4) A bra. I trust you know your size, or you will have to go and get measured. The bra should match your panties, any style is acceptable.

5) Garter belt. At least six straps, sissy.

6) Black thigh-high stockings. You knew this was coming, didn't you? Make sure to buy quality. And you'd better make sure there are no runs.

7) A little black dress. Ah, a classic in every woman's wardrobe. And of course, in a sissy's as well. You will have to buy the right size, you wouldn't want to flash your stocking tops to strangers would you?

8) High-heeled pumps, at least 3 inches high. You may bring these with you in a bag.

Other items I expect you to take care of:

1) Your nails must be painted, hands and feet. Remember, a good sissy matches her nails to her panties.

2) Shaved, from hairline to toe. If I don't think you've done a good job, you will receive a stroke of the cane for every offending hair. Followed by having it yanked out by me, of course.

3) You should be clean and well-scrubbed, in every part of your body. And I do mean everywhere.

4) You will carry a purse with you. I know, I know, it will give you away as a sissy right away, but then this is what you want isn't it. Inside, you will put the following items: the key to your chastity belt, a spare pair of stockings (in case of a run), your high-heeled shoes and some water-based lubricant.

Your instructions for your arrival are as follows:

1) You will arrive at my house by any means you prefer. I suspect that an Uber might be the least humiliating, wouldn't it? You will be dressed as I have described above, with two exceptions. You will wear an overcoat over your sissy attire, and you will wear a pair of black men's Oxfords instead of your high heels. That should suffice to conceal your sissy nature from most passers-by. Of course, there is always the matter of your nails.

2) Once you arrive at my house, you will knock and push open the front door, which will be left unlocked. Once you are inside and have closed the door, you will take your overcoat off and remove your Oxfords and replace them with your high heels.

3) As soon as this is done, you will put the spare items by the door.

4) Finally, take your chastity key out of your purse. Then assume the sissy slave position. This is as follows: On hands and knees, with elbows on the ground and palms facing upwards, with your chastity key on them. Your forehead should be touching the ground just behind your elbows. Your knees should be on the ground, and spread as wide as possible. Remember, a sissy slut needs to know how to spread. The tips of your high-heels should be on the ground.

I trust you will have no trouble following these instructions, sissy. You will have plenty of shopping to do this week, so I do suggest you get started soon. While you may be tempted to buy these items off Amazon, you are expressly forbidden from doing so. I want you to get up close and personal with the items you are going to buy. You must try on at least three of each type of item I have enumerated above, before you are allowed to buy. For best results, I'm sure a shop assistant would be delighted to help. See you next week, sissy!

Mistress