Chapter 32

Hillary Jessop was dropped off at the network offices by her husband on his way to work. He kissed her and wished her good luck, but knew in his heart that she was in for a bad time. Hillary thought she would be sick as she walked in, carrying the hated saddle mounted fucking machine in its bag, and knowing that she was to be caned for being improperly dressed the day before. She explained to the door man that she was here to see the chief, and in a few minutes Sam's secretary Annabelle came down to collect her and took her up to the top floor.

In the lift, Annabelle said, "I understand you are here for punishment?"

Hillary was near to tears, as she nodded, and whispered, "Yes I am."

"Oh dear, bad luck. The chief isn't in yet. You will have to wait for him I'm afraid. Sometimes he can be quite bad tempered in the morning. Will you be getting the cane?"

Hilary nodded glumly. Annabelle had actually been told what was coming for the woman, and why, but enjoyed pretending ignorance and making Mrs Jessop explain. As they walked down the corridor she asked, "Do you know how many you will be getting?" Hilary stammered that, no, she hadn't been told.

"It will be at least six, I'm sure. Oh dear. Still, at least then its all over."

She showed the older woman into her office. "What's in the bag?"

Annabelle also knew exactly what was in the bag, but knew how embarrassing it would be to have to explain. Hilary tried, but couldn't manage to say the words, so she just put it on Annabelle's desk and shrugged. Annabelle opened the bag and folded the sides down to display the machine in all it's splendor on her desk. "Ah, yes, I see. The saddle. You have been riding this? How was it?"

Hilary mumbled something inaudible and Annabelle decided to let her off further torment. She picked up the phone and dialed Finance. "Mrs Jessop has brought the fuck machine back, would you come and collect it please?" Then she smiled sweetly at the desperately embarrassed woman and said, "The chief will want you to be standing over there, facing the wall." Hilary was wearing a smart red dress, the skirt short enough that Annabelle could just see the welts of her stockings. Sam had told Annabelle why Hilary was being punished and wanted to see what undies she had chosen to wear for her punishment. She said "With your hands on your head, please, Mrs Jessop."

As Annabelle had expected, raising her arms lifted the dress. Now Annabelle could see bare thigh above Hilary's stockings, and two suspender straps at the back. Very cute. She pretended to get on with work at her desk. Just to rub it in, she said, "Actually Mrs Jessop you had better go stand right in the corner, as close as you can, your nose should actually be touching the wall."

It was desperately humiliating for Hilary; this girl was younger than Tammy, her own oldest daughter and was telling her to stand like a naughty school girl waiting to be beaten! However there was nothing she could do but obey and hope the chief wouldn't be too long, or in too bad a temper. On the other hand, when the chief arrived he intended to cane her, so another part of her hoped the chief wouldn't ever arrive!

"He should be here soon, you had better take that dress off, you can hang it on the coat rack over there." Hilary turned and stared at Sam's receptionist, was she serious? It was obvious that she was, so Hilary reluctantly undid the dress and shrugged it off, and put it on the hook. Then she stood rather helplessly not sure what to do next.

And that exact moment Finance arrived to collect the fuck machine! He took his time running his eyes over the shivering woman, then picked up the machine and asked her if it had worked okay. Hilary mumbled that yes it had. He asked if the cock had been the right size. Hilary said, "Well yes I suppose so."

"How long did you manage to ride it for?"

"About half an hour I think."

"Have many orgasms?"

Hilary blushed scarlet as she nodded, remembering. Annabelle was sitting looking up at her, grinning hugely. Hilary decided she hated the young girl.

"Did your daughters ride it too?"

"Yes they both did."

Unable to justify staying longer, Finance, his cock rock hard, reluctantly left, carrying the machine.

Annabelle sat there openly admiring the lady's underwear for a moment, then said, "Better get back in the corner again before the boss arrives."

Sam loved these times, knowing a girl was waiting for him and dreading his arrival. He walked in and saw Hilary standing obediently, she started to turn toward him but Annabelle snapped, "Keep still, Mrs Jessop." Hilary turned back to face into the corner, her heart pounding, and sensed Sam walking past her and going into his office, closing the door behind him. Five minutes later, the intercom on Annabelle's desk buzzed. "Yes Sir?"

"Send Mrs Jessop in."

Hilary was shaking as she entered Sam's office. She walked toward his desk and stopped in front of it, looking very lovely. Looking as though she was about to burst into tears.

"So you dressed properly today. Well done. Why couldn't you have been dressed like this yesterday?"

"I'm sorry Sir."

"Yes, in a few minutes you are going to be. Have you ever had the cane before?" When Hilary moaned that no, she never had, Sam buzzed Annabelle. "Bring me in a number two cane please."

Sam actually had more canes in cupboards around his office than he had in Annabelle's office, but it always amused him to have the pretty young girl come in to embarrass his latest victim. Hilary cringed as Annabelle walked past, smiling sweetly, and handed the cane to Sam.

"I think maybe you had better stay to help Mrs Jessop keep still. Lay yourself over my desk, Mrs Jessop. Annabelle, you come and sit here and hold Mrs Jessop's wrists."

As he said this he stood up and walked around behind the reluctantly bending woman. He moved close behind her and hooked his fingers in her panties and slid them down to mid thigh. The room quickly filled with a very strong 'hot woman' smell. He ran his hand over her buttocks then down between her legs. "Feet wide apart please, Mrs Jessop. Give Annabelle your hands so she can help you keep still. I am sure you understand what the penalty will be for standing up without permission." He tapped the tip of the cane across her tightly bent bum, then raised his arm high above. He winked at Annabelle then brought the cane down hard.

Annabelle had to fight hard to keep Hilary in position. The poor woman yelped and bucked and squirmed, but Annabelle had been doing this with Sam for some time and was good at holding the victim firmly. She knew that if she allowed the victim to escape, she would be caned herself later, and she didn't want that.

After six strokes, Hilary was sobbing and pleading, and Sam decided he couldn't justify giving her more. He told Annabelle to release the woman's wrists and to leave them alone. Annabelle left, confident that in a few moments Mrs Jessop would be taking good hard cock. Actually she was wrong. Sam would want satisfaction soon, but not yet. He phoned Finance. "So, Hilary, you don't want any more of the cane?"

"Please, no, it hurts too much. Please."

"I have another piece of equipment that I need to have tested. Would you prefer to do that? Or shall we put you down for another six strokes?"

Hilary reluctantly agreed to try the new machine, without even knowing what it was.