Well, let’s not waste any more time. You have your sissy, slutty supplies (tampons, maxi pads, control top pantyhose) and your toys (inflatable plug, mountable dildo, open-mouth gag), oh, and condoms, of course. I want you to put your control top pantyhose on, being careful not to get a run in them. They will feel so soft, so sexy and tight against your thighs. Walk around in them. Walk in front of the mirror. Look at your ass and the nice way they hug and encase your butt cheeks. So hot, so ready to fuck!
Hello my sissy bitch,
How’s your sissy clittie today? Hard already, as you read this email? I am sure your pussy is wet and your cunt is aching. My little panty-wearing bitch is becoming quite the girlie slut already, and I am very impressed!! This lesson will bring you even closer to your ultimate SISSY SELF, stripping more of your “manhood” and putting you in your place.
The ultimate goal, of course, would be to sissify you so extremely that you’d fit right in with my girlfriends in a night on the town. We’d rent a limo, sissify you in the salon on the way out, and turn you into a cocksucking bimbo before taking you to clubs and ultimately selling your mouth to horny men and women. Does that sound too extreme? Perhaps. But as you imagine what it would feel like to be hogtied in your lingerie, your bra full of big new titties, your lips painted with the prettiest lipstick, I know you find yourself squirming in your chair. Wrapping your lips around our strap on cocks, enduring cum facial after cum facial, all while strapped into an unforgiving corset and locking high heels…it terrifies you but excites you.
Really, though, what matters most is what me and my girlfriends think. We all would enjoy standing in the Victoria’s Secret as you walk up to the sales girl with your note, watching from the sidelines, seeing the pretty woman read the note and then look you over, only to call her manager over and show her the note. Oh, the humiliating in your face as they exchanging knowing looks, stare right at your crotch. It’s as if they can see right through your clothes and know you are in panties and a bra, and that you are not nearly the “man” you are pretending to be, but deep down, you are just a pathetic little sissy who needs to be shown his place…
Well, let’s not waste any more time. You have your sissy, slutty supplies (tampons, maxi pads, control top pantyhose) and your toys (inflatable plug, mountable dildo, open-mouth gag), oh, and condoms, of course. I want you to put your control top pantyhose on, being careful not to get a run in them. They will feel so soft, so sexy and tight against your thighs. Walk around in them. Walk in front of the mirror. Look at your ass and the nice way they hug and encase your butt cheeks. So hot, so ready to fuck!
You will need to wear your pantyhose under your clothes three days this week. Those will be nice and distracting as you try to go about your activities, hoping no one will notice the difference in the way you walk.
You have to also endure more stretching of your ‘pussy’ by inserting the inflatable plug and pumping it up more than half way. Do this while you are on all fours, sucking the realistic cock as it is mounted at eye level. Don’t forget to put on your sissy lipstick or lipgloss. Alternate sucking with pumping up the plug. Once it has been inflated more than half way, you have to turn on the vibrator all the way. Ohh, my poor, stretched little bitch! I wish I could see the look on your face. You will have to describe it in great detail in your next homework lesson that you submit…
You have to endure this stretching, cocksucking ritual one time each day for twenty minutes. And – no cumming. Sorry, my sissy, you have to learn some self control…
It’s time, though, that you get used to the O-ring gag, because you will be wearing it as part of your upcoming humiliation training. You will need to wear it for increasing increments of time – first for ten minutes, then twenty, then thirty – so that by the end of this week you can wear it for the full half hour. Your jaw is going to ache. Are you wondering what the reason is for this open-mouth treatment? Oh, trust me, it will be very degrading.
As you perform the exercises in this lesson, I want you to begin thinking about your upcoming trip to Victoria’s Secret (or, whatever lingerie store is near you); that lesson will be coming soon. In a few days you are going to be given a note that you must seal in an envelop and bring to the prettiest woman that works there. I, of course, will know what the note says, since I wrote it. And I can assure you, you will never feel such intense humiliation as when she looks at you and proceeds to assist you with the instructions.
Meanwhile, those cum cubes are safely in the freezer awaiting the “party” we will be having, and your ass and mouth are being stretched and transformed little by little.
For your homework, email me a detailed description of your exercises as described in this email. For extra credit, send me a picture of your pussy in the pantyhose. Also, you must tell me the city location of the Victoria’s Secret or lingerie store you will be visiting. THIS IS MANDATORY! You must use the subject line “pantyhose bitch.”
Akasha’s Extreme Feminization/Humiliation Training Lessons in this series:
There are a few toys you should have in your collection to start. Of course, you are always welcome to use your existing toys or household items. I have a few toy recommendations that will help you, however:
