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 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.