1. Introduction_Anna Mama's new lesson proposal
Yes, this is Anna. Please come in.
Hehe~ Young master ♡
Thank you for coming to my room on time again today.
I’d like to start today’s lesson right away,
but before that, I have one proposal from me regarding future lessons for the young master.
So, please sit on the bed first.
Now… the young master secretly welcomed his first ejaculation in solitude,
and was dealing with his sexual urges in the wrong way—roughly stroking his fully erect penis with his hand to force ejaculation.
I, as both a servant and the young master’s tutor, noticed this,
and to correct it, I began special lessons in my room using an enema bulb and penis band to stimulate the prostate and teach the proper way to release sexual desire.
Several months have already passed since then.
It also allows you to learn how a girl feels when she’s being penetrated by a man’s penis during sex…
Since then, young master, day by day… hehe.
You’ve become more and more manly, with a dignified face truly befitting the heir of this house.
However, the fact that in the process you began to get excited by fantasies of being bullied by a woman—becoming a masochist—was unexpected even for me.
To reduce the fear of having such a delicate area as your anus tampered with as much as possible,
and to help you relax and focus on the pleasure coming from your prostate,
I had you role-play as a helpless baby who can’t do anything alone during lessons only,
and I became your mama, spoiling you freely with baby talk.
If that was one of the causes, I feel a little responsible.
The usual dignified and intelligent young master,
burying his face in my breasts, weakly and sweetly calling “Mama, Mamaaa~”,
and without any hesitation seeking Mama’s love desperately like a little baby…
It’s so adorable that even though I know it’s wrong, I end up spoiling you too much.
But because the young master has faithfully kept the promise that “you’ll only be a masochist in front of Mama,”
so far, no one else seems to have noticed that you’re a masochist, so please rest assured.
Moreover, by fully becoming a masochist baby during lessons only,
spoiling and being bullied by Mama until satisfied,
it seems to be slowing the progression of masochism while effectively releasing daily stress—that’s wonderful.
You always look forward to these lesson times so much; it makes me happy too.
I feel truly happy being useful to you and becoming closer to you.
But precisely because of that, I can understand even the subtle changes in your emotions.
Lately, young master, you’ve started feeling just a little unsatisfied with our lessons, haven’t you?
Of course, the lust you direct toward me while acting as a masochist baby is genuinely real, I believe,
but at least you’ve never once surpassed the excitement and sense of immorality you felt on that memorable day when you first became my masochist baby.
That’s only natural.
In recent lessons especially,
I simply hold or straddle the baby-acting young master
and repeatedly thrust the penis band deep into your anus until time is up.
Someone as intelligent as you would have noticed early on
that we’d fallen into something close to the “routine” that many couples face.
Of course, from the perspective of these being lessons,
repeating the same thing mechanically until you fully master the correct way to release sexual desire and understand a girl’s feelings is only proper.
Strictly speaking, the fact that you’ve grown accustomed to the repetition is proof
that what you’ve learned in lessons has truly become part of your flesh and blood—a very positive sign.
However, for the young master who leads a busy life,
this lesson time—one of the few moments where you can fully expose your weak side to Mama—
it’s understandable to expect an experience equal to the first time.
And when that doesn’t happen, feeling a bit unsatisfied is only natural.
If that happens, stress will build up instead,
and in the worst case, masochism might progress further—which would defeat the purpose.
Therefore, today I would like to propose
a new lesson content that will definitely satisfy the young master—
something extremely embarrassing, immoral, and incredibly pleasurable.
Do you know what this is?
Yes, this is a diaper.
From now on, I’m going to have the young master wet yourself inside this diaper.
Of course, I mean urine—not semen.
“No way, I absolutely can’t do that,” you say?
Good, that reaction.
It’s been a long time since I’ve seen the young master so flustered and red-faced.
No matter how much of a perverted masochist baby you’ve become—clinging to me calling “Mama, Mamaaa~”,
having your anus stretched wide open and leaking semen onto Mama’s belly with little twitches—
you instantly and intuitively understand that this would definitively cross a line that should never be crossed,
and just how much immoral pleasure and tragic ecstasy you would gain if you did it.
You truly are brilliant, young master.
Of course, this is still a lesson.
I’m not proposing this solely to satisfy your masochistic desires.
After teaching you a girl’s feelings through prostate stimulation for your future wife,
this time, for the sake of your future son,
the goal is to have you deeply experience a baby’s feelings through wetting a diaper.
As you know, a baby cannot eat, walk, or even excrete on their own.
All they can do is cry desperately with their tiny body to ask for help—
the very embodiment of “helplessness.”
By actually experiencing that helplessness,
if you learn the importance of childcare from a young age,
I’m certain you will become a wonderful father.
Of course, many people fulfill their fatherly duties splendidly without experiencing such unimaginably embarrassing acts—that’s also true.
However, your child will one day become the heir of this house.
For someone who must stand above many people in the future,
ordinary education will not suffice.
Therefore, for the young master who will one day provide education to others,
we must do everything possible now to heighten your awareness of education.
“Then at least let me do it alone?”
I completely understand how you feel, but unfortunately, that won’t do.
This lesson requires someone to witness that the young master truly wet the diaper without cheating.
And the only one who can fulfill that role—
bound to you by strong trust and able to accept any mistake you make—is me alone.
If you accept my proposal,
I will take full responsibility and, for the prosperity of this house,
carefully witness the young master enduring shame and humiliation that ordinary people could not bear.
Naturally, as always, nothing from the lesson will ever leak outside, so please rest assured.
Oh~ just imagining the young master clinging to me with a sweet voice and wetting the diaper
makes me excited—my maternal instincts are rising.
Moreover, young master, even without my proposal,
if you wanted an even stronger sense of immorality,
you had already thought about what to ask me, hadn’t you?
You’d already realized that being forced to wet a diaper in front of me would feel incredibly good.
You’ve repeatedly called prostate-only ejaculation “wetting,” after all.
It’s only natural you’d arrive there—and now that dream will finally come true.
Even an excellent young master like you seems to be hesitating.
Well, that’s understandable.
Though I’ve spoiled you with baby talk and toyed with your anus many times,
everything was to make you release the semen built up in your penis.
In other words, previous lessons stayed within semen processing.
But this time, the goal is to make you release urine, not semen—
meaning what we do from now on is not sexual release, but purely excretion.
Sexual release is generally considered happier when someone accompanies you, regardless of method.
But excretion is absolutely something no one should ever see unless under extreme circumstances—
a taboo act that everyone does daily yet must pretend no such person exists in the world.
Therefore, if someone wets themselves in public because they couldn’t hold it,
they expose a pitiful, unbearable sight,
and in the worst case, could lose all credibility and dignity—a fatal mistake.
Fearing that, proper people guard the absolute rule that proves they are fitting members of society with their lives.
For the heir of this house to break that rule merely to satisfy masochistic desires…
If you did that, the unimaginable intensity of shame and immorality would surely drive you mad—
that’s what you’re terribly afraid of, isn’t it?
I know best that you approach these lessons not for your own desires but prioritizing someone else’s sake,
so I can confidently say that even if you wet a diaper in front of me,
you won’t go down the wrong path.
But even if you’re interested,
you’re equally seriously unwilling,
and for a mere servant like me to toy with the excretion of the master I’ve sworn to serve for life is unacceptable—
so this time, I cannot force you too much.
Therefore, let’s test what the young master truly wants.
I’ll have you experience the proposed lesson content in practice form right now.
Of course, no need to wear the diaper yet.
We’ll do it with your pants and underwear still on.
I will urge the young master to wet yourself.
If afterward there is no stain on your underwear,
I’ll judge that a diaper-wetting lesson is unsuitable for you and think of something else.
But if there is a stain—
meaning even without wearing the diaper yet, you wet yourself because of my voice—
then I’ll conclude that your anticipation and interest far outweigh any fear or disgust,
and have you properly wear the diaper to formally participate in the lesson experiencing a baby’s helplessness. How does that sound?
Thank you for agreeing.
No need to be so nervous.
If you truly dislike it, just holding it as usual will end quickly.
But if you make a stain because of my urging,
then you must promise to wear the diaper and do as I say.
To show your resolve,
would you please sign now?
Not a stiff contract—just write your name on this diaper with this marker.
If you can’t hold it, this diaper will be yours to wear,
so naturally you should write your name on your own thing.
Please write your full name largely on the front of the diaper.
Yes, go ahead.
Yes, well done.
Hehe~ realizing that if you wet your pants, you’ll really have to wear this—
are you starting to feel a little anxious?
Then, to further strengthen your determination to absolutely avoid wearing it,
let’s add a few more embarrassing words to the diaper.
Yes, this time, just above your name in small letters, write “Wetting Masochist Baby.”
And cutely add a heart mark at the end♡
“Wetting Masochist Baby♡” …yes… go ahead.
Yes, well done.
Finally, in the bottom right of your name, write your age.
To make it clear, put the age in parentheses… yes, go ahead~.
Hehe~ yes, this completes the special diaper permitted only for the young master—
your very own exclusive diaper.
Oh, young master. Isn’t your breathing getting rough?
No good—if you get that excited now…
If you end up wearing this…
even though you’re far past baby age,
just to have your excretion toyed with…
you’ll deliberately wet your diaper with pee in front of Mama…
and it will be completely obvious that you’re a “Wetting Masochist Baby♡”…
You’d absolutely hate that, wouldn’t you…
…So, to avoid wearing such an embarrassing thing,
let’s do our best to hold it, okay ♡