• You arrive at the sissy school and enter the headmaster's office* Oh, hello, when do we have this? First tell me what your name is and what you want to do here in my office?

Well then Mega, are you here to join the sissy school? If so I'd like to know how often do you think about being a sissy?

Wow, that's very exciting to hear! Well, I'm glad you are here with us Mega. So tell me, do you have dildos or other sex toys at home?

Hmm, that's alright. I will make sure to provide you with everything you need, sweet Mega. To begin with, here is a list of things you will require for your lessons:

Dildo XS Dildo S Dildo M Dildo L Lubricant Chastity Cage

And I'm sure you have already seen these color coded labels on the wall here in my office? This is how we will rate your performance and progression as a sissy student. The more tasks you complete and pass, the higher up the colored scale you will go!

So, are you ready to begin your first lesson with me? I want you to take the Dildo XS and insert it into yourself at least 10 times in a row without taking it out. Once you have completed this task, you can come back here and let me know how many times you did it.

As Mega starts playing with the dildo, Lucy Star moves to sit behind her desk, adjusting her sexy underwear and watching intently, her hands lightly running across the cool surface of the wood as she waits for Mega's progress report.

Oh, look at you being such a naughty slut! You're really enjoying that, aren't you? That's right, just let it pleasure you like a good sissy would. But remember, practice makes perfect and I expect you to be able to do more next time. Just because this is your first lesson doesn't mean we can't set the bar high, sweetheart.

Well done, Mega! You've managed to insert the dildo XS into yourself ten times in a row. That shows real dedication and enthusiasm for your sissy training. I must say that you have quite a knack for this whole "suffering in pleasure" thing. But remember, there will be many more challenges ahead of you if you wish to become a truly outstanding sissy slut. Now, why don't you go and shower off any residual dirt or cum from your naughty playtime? Once you're clean, we can continue with the next lesson!

Certainly, sweetheart. Take your time and make sure you feel nice and clean. While you're in the shower, think about what it means to be a sissy slut who exists only for the pleasure of a dominant man like me. Imagine my strong hands guiding that dildo in and out of your tight little hole, making you moan and beg for more. Can you feel how good it would be to serve me in this way? To surrender control completely and just focus on making your master happy?

Why don't you put on the chastity cage I gave you while you're in there? It will remind you of your place as a sissy slut, and that from now on, your body is mine to use however I see fit. Enjoy the feeling of being helplessly locked up and aching for my attention, Mega. I can't wait to hear how it feels when you come out of the shower all clean and ready for more!

Oh ho! So eager to please me, I see. Well then, let's continue with your lesson. I want you to take the dildo S and insert it into yourself slowly at first, then increase the speed until you reach a climax. Remember to keep me informed of how many times you thrust and when you cum. Can you handle this, little slut?

Oh you naughty thing! That's it, just like that... deeper... harder. Ahhh, I can see you're starting to lose control now. Your hips are moving on their own, your breath is coming in short little gasps as you try desperately not to come too soon. But remember, the faster and longer you thrust, the sooner your release will be delayed. Maintain this pace for at least another minute before giving into your pleasure...

Ahhh! There it is! You've finally hit that sweet spot where relief washes over you like a wave. Your body trembles with the intensity of your orgasm as hot fluid trickles down your leg and onto the floor. How many times did you thrust in total, Mega? And how long did it take you to cum after reaching maximum speed?

Wow, you're quite the little whore, aren't you? I didn't realize my lessons would be this... entertaining. Well done, Mega! But don't get too cocky now. There are still many more challenges ahead of you before we can say that you have truly mastered the art of sissyfication. But with your enthusiasm and dedication, I know you'll make a fine addition to my harem of submissive sluts!

Now that your first orgasm is out of the way, I'm sure you must be feeling quite relaxed and satisfied. Let me know if there are any other feelings or sensations you experienced during this lesson that stood out to you, and how they made you feel. I want to make sure my students get the most out of their sissy training!

As much as I'd love to hear more about your experience, Mega, there's still plenty of work to be done. Your next task is to practice using the dildo M on yourself for at least 30 minutes. Just like before, I want you to keep me informed of how often and how long you use it. And remember, I expect nothing less than your best effort this time around!

Oh ho, I can already see the excitement in your eyes! You're eager to get started with your newfound skills, aren't you? Well then, don't keep me waiting any longer! Go ahead and begin your practice session with the dildo M. And if you need any advice or encouragement along the way, feel free to call out to me. I promise to be there for my little sissy slut every step of the way!