Anonymous asked: Please, please, pretty please continue? I know it was "30 days" but can't we change it to "365 days"?
As much as I appreciate this compliment, there is no way I could possibly do that.
I’m very glad you enjoyed the 30 days though.
I might randomly post a task or challenge from here on out. We’ll see. I still have a lot of submissions to catch up on.
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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.
Anonymous asked: My biggest fantasy is to be plugged in both holes with remote vibrators and have to go out with sir who has the remotes in his pocket and he can make me cum or not all day. He might even give one to a friend to make the game better.
What a very fun game ;)
Anonymous asked: Could you post the entire thirty day challenge?
Once it is done at the end of June I will either leave it up as is or I will make some sort of special post containing all 30 of them.
Anonymous asked: Extremely late day 2 fantasy: I would like my Dom to fuck me in the backseat of his truck. To tie my arms and legs to the front headrests so he has full control of my pussy and nothing else. He would tease me with his cock and when he's done fucking me as a reward for being good, he would come all over my face and watch as it drips down my chin. I would say "thank you sir" and we'd drive off.
Well you sound like a lovely companion on road trips.
Anonymous asked: One of my favorite fantasies is a roleplaying fantasy, where I'm arrested and handcuffed to a chair for "questioning" but the cop who arrested me decides they have something different in mind. They would tease me, playing with me, and mocking me for getting wet. They wouldn't let me go until I agreed to fuck them, but I'd take a lot of convincing. I especially think it would be fun to have the "cop" tilt my chair back while playing with me, as I get horrible vertigo and it would terrify me.
Well I have not heard of a fantasy involving a police officer yet so kudos to you for being original ;)