Stay home

You try to summon the courage from the deepest wells of your soul, but as usual, you don't find anything but more fear. "I can't Mommy, it's too embarrassing. Can't I just stay home and take my lessons today?"

You see disappointment in your Mommy's eyes which all too soon turns to a look of recognition. This is your natural state after all, a lazy loser, a coward to afraid to fail to even try to win. She sighs, resigned to her fate and yours. "Alright, honey heart, let's get you some "tutoring" that will cure that case of "scaredy shys" for you.

For a moment you are hopeful, a bit of reprogramming to make you brave and you can go shopping no problem. But as you look up on Mommy's pained expression you know deep down you already blew your chance. You both keep your troubled thoughts to yourselves as she leads you to the basement, straps you down and starts up the vr set.

....

....

....

"Alright, scaredy kittens, time to see how your lessons went." She is helping you out of the desk and out of your clothes, the air is cool on your skin, and comforting. She hands you a new shopping list "paddle (purchase and used at downtown sex shop), 20 condoms (used), 10 loads of cum (anal), 10 loads of cum (oral), 10 loads of cum (miscellaneous)."

You look at the list and your eyes go wide. "Gee gollickers, thanks Mommy. This list is way more easier! I can find all these down at the Dildopolis downtown." She smiles sweetly as you skip upstairs, put on a tiny pink raincoat (because the law is the law), and go looking for a cab to take you downtown. Scatterbrained and shameless, you don't bother to bring any money as your sure you'll be able to work out other arrangements for your fare and the cost of the toys.

Your Mommy watches on sadly, knowing what you never will, she cured your shyness which is one of a sissy's most marketable traits. That initial blush or fetching flinch that gives way to lust and makes a man feel like a stud. Give it away too willingly and all you find are louts and even they lose interest eventually. You will always be depending on the kindness of strangers, always discovering there's no kindness to be had, and always incapable of learning that lesson because you will never be able to feel ashamed or regret any of your many mistakes.

But you will love every second of it...