She kept giving him a peek
'So, today we are going to be enjoying your breasts? Let's see just what they are like.'
Tom ran his hands gently over the soft flesh, and his fingers lingered over her nipples. They tightened until he was pinching the nipples quite hard, making Lisa wince in pain. At this Tom didn't squeeze any harder, but continuing his grip, slowly pulled her nipples away from her body until each breast was quite conical in shape. This made Lisa gasp even more and cry out loud. Tom ignored her cries and held the breasts outwards for perhaps twenty seconds before he gently released his grip. His hands then gently stroked the breasts and nipples again, sufficiently hard to maintain the erect state of her nipples, but causing pleasure rather than pain.
Unseen by Lisa, Tom stopped handling her and reached for a short flail whip made with a number of silky strands with a wooden handle.
'Let's see how they can withstand a whipping, shall we?' he said.
Lisa wanted to say no, but knew that this would reduce her earnings for the session - and she really did need the money.
Tom started gently stroking the strands of the whip across her flesh. Slowly, oh so slowly, he increased the force of the whip so Lisa could hear the ropes of the whip as they hit her breasts. Now Tom added an occasional much harder stroke to the regular flailing. When these harder strokes hit her nipples, Lisa tensed and screamed in pain. After perhaps six or eight scream inducing hits, the whipping stopped and Lisa relaxed into her bonds again.
Once more Tom fondled her breasts and ran his fingers over her now much more tender nipples.
She now felt a clip being attached to each one. Nipple Clamps, she guessed. They felt tight, but bearable.
'I'm going to whip the end of your breasts until each clamp gets knocked off' said Tom. 'Then perhaps we'll try them on again and see how much weight we can add to make them really stretch'
The flailing started again, gently as before at first, before Lisa again experience the harder strokes, this time concentrated on her most tender flesh. It only took three hard strokes before her left nipple was freed from it's clamp. As this occurred Lisa grunted in pain. The right nipple then received five blows, before it too was released and the clamp fell to the floor.
Lisa found her arms were getting tired and the bonds around her wrists very tight as they took some of her weight. Her nipples felt stretched and sore and she wandered whether to use a safe word, at least to get some respite. But Tom seemed to anticipate her needs because she felt her wrist ropes being released, and then her ankle restraints. He also removed the eye mask and Lisa blinked as the unaccustomed light
'Take a moment to rest' said Tom. 'You are really coping very well'
Lisa stretched and flexed her arms and straightened and flexed her legs and Tom guided her to sit in a hard wooden chair. Lisa rubbed her breasts to try and alleviate the pain in the nipples.
After all too few minutes rest, Tom asked Lisa to stand up. This time he leant her body forward, so that her head and shoulders were resting on the seat of the chair. Once more Tom attached the clamps. This time each clamp had an empty plastic bottle, hanging straight down from is on a short piece of string.
'I'm going to slowly add water to each bottle' said Tom. 'You can stop the water being added at any time by saying "amber" but otherwise I'm going to continue adding weight until the clamps fall off. If you can manage that I'll add __50 to the money you receive.'
Tom poured a small amount into each bottle, then slowly alternated between each one until there was almost two inches in each.