Inmate 320 entered Headmistress Katherine’s office at 8 PM. The
escort had been sent to get him and bring him there. He was naked,
except for the appliance which all male inmates wore – a cock cage.
With hands bound behind him, he had an anxious expression on his face.
He had never been summoned to the Headmistress’ office in the evening,
and wondered if he was in trouble.
He saw another unexpected sight. An attractive woman was seated on
the examination table which was in the Headmistress’ office. She
looked up at him and smiled. Her long wavy reddish hair nicely rested
on her white blouse. Her short black skirt showed off her attractive
bare legs, and her black high-top shoes gave her a sensuously slutty
look.
“I had you come here,” Katherine said, “because your good behavior has
been noticed. I want to give you a very special reward. I can’t
leave you alone with her, but you can still have some fun.” Katherine
stood up and walked to the examination table where where Ann, the
other woman, was seated. She handed Ann a key.
Ann spread her legs and revealed that she had no panties. Her pouty
labia peeked out from her matted red-haired bush. She smiled sexily at
the inmate and beckoned him with her finger to come hither. When he
aproached, she unlocked his cock cage. His hardening erection sprang
forth.
With the astonished male standing before her, Ann slowly jilled
herself to orgasm. She gasped several times as she crested, and when
she recovered her breath, she lustily whispered, “I’m ready for you
now!”
Ann knew that the male, because of the cock cage, had not experienced
sexual relief in a long while, and she wanted to be careful lest he
pop off before she got his member inside her. She lightly grasped his
cock and pulled him toward her entrance. As he approached, she spread
her creamy labia with her other hand and guided his member into her.
“Go slow,” she admonished as she leaned back on the padded table.
“You’ve been saving up for me, and I want to get every drop.”
The male, his hands still tied behind him, pumped hungrily. His cock
had a will of its own and would not do any bidding except toward its
immediate satisfaction. After a few thrusts, his member pulsed and
throbbed inside Ann, and he exclaimed with a disappointed moan.
“Stay inside, stay inside!” Ann instructed. He continued to pump
after he spent his immediate wad, striving for as much sensuous
satisfaction as would be allowed after his quick ejaculation. After a
moment of plowing, Ann pulled back and he slipped out. “I thought you
would do better than that,” she admonished. I’m going to give you a
second chance. I’ll be back in a while.”
She got up and left the room.
Headmistress Katherine slipped on some disposable gloves and, with a
slight smile, beckoned the male to approach. Over the next twenty
minutes, she slowly teased his cock until it throbbed with pent-up
desire.
In another room, a totally different scene took place. A naked male
was bound face-up on a narrow bench. His erection pressed against the
confines of his cock cage. When Ann walked in, she knew that the two
escorts who had bound the male to the bench had been teasing his cock.
They were skilled at what they did, and the male knew that he was
being punished. He did not know the extent of his punishment that
evening.
The red-haired Ann dressed sluttily for one reason – to arouse. She
unlocked the male’s cock cage. His member sprang upward, and the
other girls giggled. Ann straddled the bench standing up, with her
legs spread and her aroused and creamy pussy a few inches above the
male’s face.
“You know, it’s totally up to me whether you get relief tonight,” she
told him. “You’ve got to earn any pleasure. Now I want you to suck
my snatch!”
She bent her knees and her creamy pubic bush made contact with the
male’s mouth. The male was surprised at how creamy this woman’s pussy
seemed. A nagging thought kept intruding – what if all that cream
wasn’t her own?
“Come on, suck it like you mean it!” Ann scolded, and then began to
moan as he applied his mouth to her pussy.
“Yes, like that! Keep going!”
It took scarcely a couple of minutes for Ann to explode in orgasm. She
ground her pussy into the male’s mouth as her insides pulsed several
times.
“Ahh, that was good,” she said as she pulled away. She nodded at the
other women and left the room. The two escorts pulled up chairs and
sat on each side of the bound male, close to his midsection. Each of
them began to diligently work on teasing and tickling his thighs, nuts
and cock. The male became practically insane with frustrated desire;
the women giggled excitedly all the while.
Ann entered the Headmistress’ office. She was gratified to see that
the inmate sported a hard erection from her attentions. Katherine
smiled and stepped back, giving the stage to Ann.
Ann sat up on the examination table and told the male to come over to
her.
“Let’s heve a feel and see if you’ve worked up a nice load for me,”
she teased. Then she palpated his cock and ball sac for a while until
he was quite obviously desperate for relief.
Ann’s eyes sparkled as she lay back on the table and placed her feet
in the stirrups. Her short skirt did not hide her exposed sex, and
her spread legs presented an irresistible scene to the inmate.
“I’ll give you one more chance,” Ann admonished. “I want you to last
a while before you pop off, or no more nookie rewards. Come fuck me
now.”
She guided his now hardened erection inide her and then placed her
hands behind her head.
“Yes, that feels good,” she moaned.
The inmate did not need further prompting. With his hands bound
behind him, he pumped, gently and slowly at first. As the moments
passed and the atmosphere became more sexually charged, he pumped
harder. He voiced a short “Uhh!” with each energetic pump.
Ann felt the cock inside her expand slightly, and she knew that he was
about to spew forth. After a moment she goaded him on. “Okay – give
it to me. Give me all that cum you’ve been saving. Give it to me
now!”
“Aaaaaaaugh!”
Ann smiled as the male lustily pounded her pussy as he spurted. Squirt
after squirt splattered inside her. The male, after a moment of this,
was completely spent, and slowly withdrew.
“That wasn’t too bad,” Ann mused. “Keep up the good behavior.” She
smiled at him and left the room.
She entered the room with the bound male, and smiled to herself. The
two escorts were still arousing and teasing him. He was clearly in a
tortured and desperate state of arousal. The escorts stopped their
handiwork and watched Ann.
Ann again straddled the male’s face with her cum-filled pussy a few
inches above his mouth. “Are you ready for some more dessert?
(Giggle) I’ve got some banana cream pie for you!”
The bound male groaned.
“If you don’t do everything I tell you, you won’t get off tonight,”
she authoritatively taunted. “Now I want you to suck my snatch until
it’s completely clean.” Then she bent her knees enough to make
contact with his mouth. He had no doubt what was in Ann’s freshly
sexed pussy, and he applied himself to the distasteful task. In the
five minutes that he spent doing that, Ann shamelessly climaxed twice.
She withdrew and turned her attention to the bound male’s erect cock.
She handled and palpated it for a few moments, and then abruptly said,
“No, not yet. I’ll be back in a little while to check on you.” Then
she left the room, and the two escorts returned to their task of
teasing and arousing.
Back in the office of the Headmistress, Ann seated herself on the
examination table. A different inmate was there, his hands secured
behind him.
Katherine told the male, “I had you come here because your good
behavior has been noticed. I want to give you a very special reward.”
Ann did with this and a subsequent inmate as she had with the first
one. She enticed two ejaculations from each and required the bound
male to service her pussy and clean up each serving.
Finally, far into the night, Ann impaled herself on the bound male’s
cock. She pumped briskly, and when she sensed he was about to
ejaculate, pulled out and finished him off by hand, so that his spurts
of semen splattered on her pubic area. Then she had him orally clean
her wherever he spurted.
Twice more she thus milked him (between episodes of more teasing by
the escorts) before calling an end to the night. Each time, she had
him lick up what he had spurted forth.
