just said, and to understand that what I’m putting in your
little asshole is a kind of symbol of the way you now belong to your master, and are
for that purpose in my care, and the care of the Institute. This is a very special
moment for you, Rose. When you used to put your little vibrator inside your bottom,
before you belonged to your master and you were free to play with yourself as you
pleased, you were just being dirty. When I put my big black punisher there, I’m claiming
you for your master.”
He had the punisher in his left hand, and the lube in his right. He put just a bit
of the lube on the tip of the long, thick black rubber. He put the tip against Rose’s
cute little rear-dimple, and watched her head rear back at the feeling. She gave a
little moan as he began to push, slowly but firmly, and with increasing force.
While he pushed, he continued the lecture. “I’m afraid this is going to hurt, Rose.
If you want to keep from having many sessions like this, bottom-up for something much
too big going up your backside, you’ll think about how you got here.”
He pushed a little more firmly, and she cried out into her navy-blue comforter. The
anal punisher had four bulbs, each one thicker than the last, and Rose hadn’t even
taken the first one—only its pointed tip was inside her rectum, and Leo was just pushing
rhythmically there to teach her that he would treat her anus as he liked. But that
was the best way for a girl’s first anal training: the moment of feeling her bottom
held open at a master’s pleasure was a priceless one, and she needed to be made to
anticipate it for a long time.
“How did you get here, Rose?” he asked, quietly, as he kept pushing, pulsing the black
rubber against her sweet, crinkly bottom-hole.
With each pulse, Rose was making a little noise in her throat of fear and submission.
Leo stopped the pushing, and began to turn the punisher back and forth, applying only
the slightest pressure as he did so.
“I’m waiting,” he said. “If you’re a good student, I can be gentle with my punisher.
But if you’re not…” He pushed, suddenly, very hard, and overcame Rose’s resistance.
She shrieked in pain as she felt the first bulb enter, and then sobbed when she realized
it was inside her, and that her anus had closed around it. Leo pushed again, to let
her know the second bulb was there, waiting for her, but then let up the pressure.
“See, Rose? I think you should answer me, don’t you?”
“I… oh, God… I threw a glass at you, and… oh, Master, please, no… I tried… to open
the door.”
“There we go, sweetheart,” Leo said, giving her a little pat on her right bottom cheek
to let her know he was pleased. “Now, I have lube here, and I can put a little on,
if you continue to be good. Would you like that, Rose?”
“Yes, Master,” she said, in a strained, resigned voice.
“Alright, since I’m a kind master, I’m going to put a little lube on just because
you responded properly.” He let a tiny drop fall from the tube onto the place where
her anus was held so beautifully open by the black rubber, then, hardening uncomfortably
in his jeans at the sensation, he gently rubbed it in while Rose gave little sobs
of discomfort. He tugged and pushed on the punisher, just a little, experimentally,
and she cried out. “That’s better, isn’t it?”
“Yes, Master,” Rose moaned.
“Now that we understand each other, we can begin. I want to hear about ‘Backdoor Pleasures,’
first. Can you give me a synopsis?” He turned the punisher just a little, with the
tiniest bit of inward pressure, to encourage her.
“It’s… it’s about a college student… and… and… oh, please… and her boyfriend says
it’s time for her to… to try anal, but she… she thinks it’s dirty… oh, God.”
Leo added a little lube. “You’re doing fine, sweetheart,” he said. “How does the
Alaska Angelini, A. A. Dark