30 days of Sir - day 30
Well would you look at that, we spent 30 days together.
Time flies when you’re having fun, right?
You must be a wet, horny little mess right now.
Don’t worry, today is going to be a fun one.
Let’s make sure we end this with a bang.
From the moment you wake up until the second you fall asleep tonight, I want you to play with yourself as many times as you possibly can.
I want you to cum over and over throughout the day.
You can play any way you wish.
Look at any pictures or videos, read whatever you want or imagine anything you want.
Use toys, use your fingers, use whatever you want.
Cum in private, cum in public.
If you’re at work, cum at work.
If you go shopping, find a bathroom.
I want you to count each orgasm.
Cum 5 times, 10 times, 15 times, 30 times… as many as you can possibly do.
I want you to break your record.
By the end of the day, I want you exhausted.
Tonight, or tomorrow, send me a message.
Anonymously only, and only a number.
I’ll post it as they come and we’ll see what results we get.
For the last time: Enjoy.
30 days of Sir - day 29
Remember when we used your favorite undies?
Remember cumming in them?
Let’s take those out again today.
When you first read this, I want you to find them.
Pull them out and place them on your bed.
Leave them there.
Go out today without any undies on, knowing they’re on your bed all day.
When you get home tonight, when you’re all ready to go to sleep, go back to your bed.
Look at them, waiting for you.
Get completely nude and put them on.
Lay down on your bed.
Rub over them, just like you did before.
Only over them, no cheating.
I want you to play over them for 10 minutes.
Absolutely NO cumming.
When time is up, I want you to take them off.
Slide them down your legs.
Ball them up.
Stick them into your mouth.
I want you to taste your wetness on them.
Tasting what you desire most right now.
Slide your hand down and play with your pussy for another 5 minutes.
Taste your undies in your mouth.
Let your moans pass through the fabric.
Make them even wetter with your spit.
Once again, absolutely no cumming.
When the 5 minutes is up, take your hand off your pussy.
You’re done for the night.
Take your wet little undies out of your mouth and put them back on.
Tonight you are to sleep in them.
When you wake up in the morning, you’ll have one last challenge from me.
Get rest, because tomorrow is going to be a big day.
30 days of Sir - day 28
There’s something I read one time that has always stuck with me.
“If you can’t turn yourself on, how do you expect to turn anyone else on?”
So this is what you’re doing today:
Turning yourself on.
I want you to pick out your very favorite outfit. I want you to be very detailed.
Your favorite bra and undies.
Your favorite skirt or dress.
Maybe even stockings.
I want you to pretend like you are about to seduce someone.
How would you dress?
Do you have something in mind?
Pay attention to every single detail.
When you’re all done I want you to get in front of a mirror.
Preferably a full-length one.
I want you to look at yourself, all done up and sexy.
I want you to see what someone else would see.
Now, run your hands over your body.
Over your clothes.
I want you to watch your hands.
Take your time.
Enjoy every detail of what you’ve put on just as someone else would.
Slide your hand under your shirt or dress.
Under your bra.
Feel your nipples.
This is what it feels like to be on the other side… This is what it feels like when someone gets turned on by you.
Now slide your hand down between your legs.
Grab the innermost part of your thighs.
Keep your eyes on the mirror.
Watch your hands.
Leave them there for a moment.
This is what it feels like to be turned on by you.
Now place them on your pussy.
I want you to play while watching yourself in the mirror.
I want you to take it all in.
I want you to watch yourself cum.
Don’t you dare take your eyes off that mirror.
30 days of Sir - day 27
Let’s explore something.
Maybe it’s something you’ve never explored before, or maybe you know it all too well.
You might not like it, you
Might love it.
Either way, you’re going to do this today.
But don’t worry I’ll go easy on you.
I want you to tease yourself a little bit, play with your clit.
Slide your finger in and out of your pussy.
I want you to get nice and wet.
Play for a bit. Lightly.
Now here comes the fun part.
I want you to take your free hand and put it in your mouth.
Your fingers wet your spit.
Suck on them as you continue playing.
Then I want you to reach down and I want to you place one finger on your little asshole.
I want that finger to stay there.
Rub around in circles slightly.
Keep it in sync with your other hand.
Make them rub together. As one.
That finger is not to leave your ass.
The only way you are allowed an orgasm today is if that finger stays put.
Explore with it.
Up and down.
Around in circles.
If you really feel adventurous go ahead and slide that finger in.
Just the tip, or as deep as you want to go.
Play around. Explore.
And then you may cum.
But remember that finger is not to leave your ass.
30 days of Sir - day 26
I’m a very visual person.
I can get very turned on at the right sight.
Sight is important after all, isn’t it?
That’s why I’m taking yours away.
Find something you can blindfold yourself with.
I don’t care what it is as long as you can cover your vision completely, it’ll work.
Lay on your bed.
Put it on.
You must be completely naked for this.
Run your fingers over your body.
I want you to take your time with this one.
I want you to tease yourself.
Let your fingertips travel all over.
Let them graze against your skin.
Let your hands take control, let them do whatever they want.
Don’t let time be an issue.
Get lost in the moment.
Grab your neck.
Tease your nipples.
Trace a line down to your legs.
When your hands end up between your thighs, let them take over.
Let them find your pussy.
Feel your wetness.
Feel the details. Every movement.
Play for as long as you can.
Feel the build up.
Until finally, you want to explode.
Until you feel your orgasm wanting to gush through your fingers.
Then, let it happen.
Cum as hard as you possibly can.
Enjoy every second of it.
Let it last as long as it wants to.
When its over, wait a moment.
Feel your body after it cums.
The little spasms.
And when you finally catch your breath…Then you may take the blindfold off.
30 days of Sir - day 25
Today is going to be all about your nipples.
We can’t neglect them can we?
Go ahead and take them out.
I want them fully exposed.
Place your fingers on your chest. Slide down to them.
They feel good don’t they?
Rub lightly at first.
Give them a little tease.
Now a little harder.
Put your fingers in your mouth and get them nice and wet.
Place those wet fingers back on your nipples.
Can’t you just imagine a tongue on them?
Rub around in circles.
Good, now lets try something.
I want you to find something to clip onto them.
Anything you can find.
Place them on both nipples, then run your hand down your body.
Lower until it’s right on your clit.
Now you get to play.
Leave the clips on and play as hard and as long as you want.
Feel your nipples get sensitive.
Feel the pleasure.
Feel the pain.
Play until you cum.
You are allowed to take the clamps off at any time.
But, there is one catch: if you take the clamps off before you cum, playtime is over. No cumming.
I suggest you leave them on and endure the pain to get the pleasure.
30 days of Sir - day 24
Let’s play with some water.
Have you ever taken a very hot bath?
No, I don’t mean temperature-wise.
Have you ever been really turned on while in the water? Maybe even played with yourself a bit?
Have you ever used the water to play?
Well, this is what we’re doing today.
I want you to get into your bathtub.
Don’t fill it up with water yet, it has to be empty.
When you’re inside, turn the water on.
Set it to a desirable temperature, then place your pussy right under the running water.
Feel it right on your clit, dripping down.
You are not to touch yourself, only the water is allowed to.
Move yourself around. Thrust.
Feel it’s liquid flow climb down every last little part of your pussy.
Let the water drench it.
You may cum as many times as you please, but…
You only have until the bathtub fills up.
Once it’s full, you’re done.
30 days of Sir - day 23
Today, masturbate somewhere you have never tried before.
Go outside of your house.
Go to a mall.
A dressing room.
A public bathroom.
Someone else’s backyard.
In a forest.
Behind a bush.
Under a tree.
At work? Do it in your boss’s office.
On an airplane? Do it in the plane’s bathroom.
Masturbate, and cum.
After you complete today’s challenge, anonymously message me exactly where you chose.
30 days of Sir - day 22
Today you’re going to be a bit of an exhibitionist.
You’re going to go onto omegle and you’re going to play for someone.
It can be the first person you see, or you can be picky about it.
It can be a male or female, your choice.
But you’re going to let them watch you.
Don’t talk to them, don’t show your face, only play.
Look at their reactions, how you turn them on.
Play, cum, then get off omegle.
30 days of Sir - day 21
Today is about time. Time is very important, isn’t it?
That’s why I won’t waste too much here.
I simply want 9 minutes and 55 seconds of your time.
What could I possibly do in 9 minutes and 55 seconds?
Well, I’m giving you an oppirtunity to cum.
You’re going to get to rub your clit.
But, we’re playing with time. Remember?
So here is what you get:
You get 10 seconds of rubbing. That’s it.
Start rubbing and count to 10.
When time is up, stop.
That got you a little excited, didn’t it?
Now, you have one minute of waiting.
Think about how you want to touch again.
How you need it.
After it’s up, you get to play one more time.
This time, 9 seconds.
Count to 9.
Even more frustrating?
I bet it is.
Wait another minute.
Do you feel yourself getting even wetter?
Want to play longer?
Sorry to disappoint.
After the minute is up, guess what you get?
Do you see a pattern?
Wait a minute.
You’d better try very hard, because each round there’s less time.
You’re either going to cum, or you’re not.
Wait a minute.
Wait a minute.
Have you managed to cum yet?
As soon as you do, the game is over.
But if you don’t, you are to play until the bitter end.
It’s upto you to cum.
Wait a minute.
Wait a minute.
I wonder how wet you are.
How drenched your fingers are.
Don’t stop yet.
Wait a minute.
Wait a minute.
Last chance… I wonder if you’re so frustrated that one little touch can make you cum.
Let’s try it.
Now, one of two things happened. You either came, and I’m very impressed, or you are a soaking little mess right now.
Either way, today’s challenge is over. No more touching. No more playing.
30 days of Sir - day 20
Are you ready to cum?
Are you desperate for it?
I wonder how badly you want it.
What would you do to get to cum today?
Lets find out.
You are already allowed to cum.
Are you excited about that?
I bet you are.
I bet you’re already wet in anticipation.
But, there’s a small catch… A little challenge.
You are not allowed to touch your pussy at all with your hands or any sort of toy.
So, what are you to do?
Well it’s simple…
You are only allowed to cum while humping something.
What you hump, is upto you.
A bed post.
The corner of a desk.
Your favorite teddy bear.
Try things out, get creative.
I don’t care what it is.
But remember, you are not to lay a single finger on that pussy of yours.
Let’s see how long it takes you to cum.
Let’s see how desperate you are.
30 days of Sir - day 19
We don’t always get what we want do we?
Sometimes, we have to be patient.
Sometimes, nothing happens.
Today, there is no orgasm.
Today, there is no playing.
Today, there is no task.
Today is simply put: nothing.
30 days of Sir - day 18
Take something out you can use to tie your wrists up with.
If you have rope around that’s ideal, if not get creative.
A tie. A shoelace.
Even a hair tie you can wrap around a few times.
Whatever you choose, wrap it around your wrists.
Use your hands, your teeth… any way you can.
I know it’s not easy to do yourself, but I also know that you’re a good listener and you’ll try your hardest.
Do your best. Make it tight.
Now that you’re bound, I want you to stop for a moment.
Realize the position you are in right now.
Tied up. Helpless.
At the mercy of whoever would be in front of you.
Have you been tied up before? I should hope so.
Remember what it was like?
Unable to move.
Unable to struggle.
Now, with your wrists bound, reach down and slide under your undies.
Rub your clit over and over.
Take your time, enjoy it.
Soft, then hard.
Slow, then fast.
Go lower, slide your fingers between your lips.
Go in as deep as you can.
Slide in and out.
Fuck yourself however you can, as hard as you can.
While you play, remember you’re tied up.
Feel your wrists, tight.
Now, play until you cum.
Enjoy it. Every second of it.
And when you do cum, cum hard.
Only when you’re done can you untie yourself.
30 days of Sir - day 17
Remember how much control you had to have?
Let’s try it again.
Just like last time, I want you to rub and fuck your pussy until you bring yourself to that point.
That point where the only thing you want is to cum.
When nothing else matters and you need it.
No playing, no cumming.
Don’t you dare.
Today, I want you to ege 6 times.
Spread them out to as close as you can to two hours apart.
All day I want you to be on the verge of an orgasm.
All day, I want you to think about how badly you want to cum.
But today, you don’t get to.
You will go to sleep tonight with a wet, wanting pussy.
When you wake up tomorrow still horny from today, before you do anything else, you are to start your day off by playing.
Finishing what we started today.
The first thing you will do is play, and cum.
Only then do you get to start your day.
And remember, there is a new task waiting for you after you finish.
30 days of Sir - day 16
That word alone should make your eyes widen whether it excites you, or scares you.
SPanking can be used in many ways and for many reasons.
They can be used as punishments, or for rewards.
To teach lessons.
To heighten senses.
To give pain, pleasure, or both.
Today, you’re going to feel exactly what it is spankings bring out in you.
First, we need a number.
Let’s do something simple.
There is your number.
That is how many spanks you owe me.
But you don’t think it’s THAT easy, do you?
That number, goes for each cheek.
I want you to bend over anything you wish.
Your bed, a couch, a chair.
I want you to slide your pants down.
Now your undies.
I want your bare ass in the air.
Now, remember your number?
Start with the right cheek.
Spank it as hard as you imagine I would.
Do you think you’d get away with little love taps, or a nice proper spanking?
Feel each one.
Feel your ass get red.
When you’re done, it’s time for the left cheek.
I want it to feel exactly what the other felt.
I want your ass sensitive and raw when it’s done.
Now, you have a choice.
You can end it now and go about your day.
Just a sore, red ass.
You can do it all over again.
Each cheek, same number.
But with this choice after you’ve finished, you are allowed to lay down, feeling your sore ass rub against your sheets and play in any way you wish until you cum.
Remember what you just did to yourself.
Feel the sensation each step of the way.
Until you can’t hold it in anymore.
Until you orgasm through your fingertips.