The Countess and the Caretaker - part eighteen

Knowing that she had brought him to a level of pain where he was
truly sorry for his actions, she was satisfied for the moment
and moved away to give him a small rest.

She then had a short conversation with Pearl, where she
suggested that now would be a good time for her to practice with
her cane and told her to give him six strokes, by which time,
the Countess considered he would be completely chastened.

Pearl enthusiastically agreed, and was already looking beyond
this experience to the plans she had been fomenting for her
unsuspecting boyfriend.

Remembering everything she had learned earlier, she placed
herself in the correct position and delivered the six strokes
with great panache, at which stage a knowing look passed between
pupil and teacher, and The Countess knew that further lessons
would not be necessary.

Pearl thanked her hostess profusely and then made her apologies,
for she had to leave. The Countess suggested she keep the dress
as a present and then the maid was called to show her out,
leaving the Countess alone with the Caretaker.

                    ********************

She ran her fingers through his hair, and told him she was proud
of him. This made him feel wonderful, and he forgot about the
pain he had endured, as he swore undying loyalty to his
tormentress.

She seemed pleased with his protestations and patted him on the
head. She then moved away from him to a cupboard where she had a
collection of dildoes, selected one, and moved back into his
line of sight to strap it on.

She was quite pleased with the look of shock and disbelief that
spread across his face, and she knew he must be a virgin.

As she lubricated the latex covered phallus, she explained that
this was the final humiliation for a man. To be treated the way
he is so keen to treat any lady that comes his way. A taste of
your own medicine, by a total reversal of the conventional
roles.

Then she moved behind him and inserted the dildo, slowly at
first, and then with more force until he had it all inside him.
He gave a little gasp of pain upon penetration, and then his
breathing became deeper as she moved in and out rhythmically.

They both became progressively more excited, as the dildo rubbed
against her clitoris, and the motion manipulated his penis on
the leather table.

He came first, with a deeper, more profound climax than he had
ever experienced before. She came a minute later, and collapsed
onto his body, in a state of exhaustion.

For several moments she just lay there, then she recovered
sufficiently to withdraw and unstrap the dildo.

She then left him alone to consider his position and to allow
the full force of what had just happened to him to sink in. She
must have been gone for at least fifteen minutes, and when she
returned he was really pleased to see her. He was beginning to
feel lost when she was not around.