Tom's journey into submission. Part 4
Tom was alerted to the action by a splash from across the wall. He rushed upstairs and into his old bedroom, with its painted-over window. He eased it up a few inches and peered out into his neighbour's garden. He had to look. He was eighteen! Of course he had to look. A second splash and a girlish shriek to follow. Tom raised his eyes over the parapet and was awe struck with what he saw, just twenty yards from his window.
As expected, her saw Evelyn, her head above the surface beaming happily at the second person in the pool. A girl. It was Lisa. As Tom watched, Lisa stood up in the shallow end and lazily untied the top of her bikini. She lifted it over her head and threw the garment at Evelyn, who jumped up and caught it. As she did so, her right tit came free from her own bikini top and Tom could see her dark nipple against the olive skin. His cock began to react.
Evelyn followed the example of her young friend, and removed the restraining bikini top altogether and just let it sink to the floor of the pool. Then she kicked off and swam to her friend, and without pausing, sank under the surface and Tom could see her pulling the girl's pants down, and off. His cock was the first to react, followed by the girl who shrieked again in mock alarm as she stepped out of her bikini. The water was churning too much for Tom to get a clear view, but it was obvious that Evelyn had removed her own pants and she was now rolling them into a ball. She swam up behind Lisa who was standing in the shallow end, nakedly exposed from the waist up, and rising up behind her, Evelyn placed her bikini pants into the mouth of the girl in the pool with her.
Tom fully expected Lisa to simply take them out of her mouth, but she didn't. Instead, she waded to the poolside opposite Tom and pulled herself half out of the water, laying her chest on the tiles and exposing her bottom, with her legs trailing in the water behind her. Tom couldn't help but notice the marks on the girl's buttocks. A good dozen or more bright red stripes across each cheek. Lisa has been caned, he realized, and obviously very recently. His cock was fully engorged and he just had to drop his shorts and start playing with it.
Evelyn approached the girl and with her back now to Tom, gave the girl six hard slaps on each buttock. The sound of wet hand spanking wet bottom carried to Tom and his cock almost exploded. He had to stop stroking it to prevent himself from cumming too soon. He knew there was more to see, and he was right. The girl rolled over onto her back and brought her ankles round the back of Evelyn's neck, drawing her face down towards her pussy. There was no resistance from Evelyn and within moments, she was feasting on the girl's cunt. The howls and shrieks of pleasure were dimmed by the bikini gag the girl had in her mouth, and knowing that in her current position, Evelyn had no way of seeing him, Tom stood up and opened the window a further twelve inches or so. He wanked furiously, spraying his load into the garden below once again.
At this, the girl tapped Evelyn on the shoulder. Evelyn immediately rose up and turned her head to watch Tom as he squeezed out the last drops. He couldn't help himself if he tried. Evelyn moved to one side and Tom got a view directly of Lisa's highly aroused twat. As Evelyn turned he could see her thick, stiff nipples and he couldn't drag his eyes away from the delights he was seeing. He knew he was caught again. Evelyn waded across the pool, looking at Tom the whole time, and rose up the ladder of the pool. She stood, stark naked, with her hands on her hips and looked up at him. He could see the swollen pussy lips, completely without hair as he stared out of the window at the goddess.
She didn't have to raise her voice. "Well, Tom. Not just a nasty spying boy, but one so foolish as to repeat the exact offense which earned him six strokes of the cane. I think you had better come down here, Tom, and apologise to Lisa and me."
Hastily, Tom donned his lightweight shorts, forgetting completely to put on underwear, and went downstairs. He hopped over the wall and sheepishly stood with his hands grasped in front of him, and his eyes down.
"I'm sorry, Miss. I just couldn't help myself from watching you with Lisa." He looked over at the girl, who was still naked. And she was a beauty too. Thick, dark blonde hair with a fringe, but only shoulder length so her boobs were exposed completely. Neither large nor small, they clung to her chest forming lovely curves that Tom would love to hold but experience told him he couldn't. Strong nipples, a deep coral tone, pointing slightly upwards. Slim waist and curvy hips, and once again, a totally shaved pubis highlighting the thick, aroused outer lips of her pussy. She had removed the cloth from her mouth and was standing unashamed, looking at this boy who had so easily fallen into their trap.
"Tom, once again, you meet Lily. As you know to your cost, Lily is my very dear friend who visits me once every month. As you will have noticed, I like to cane her, Tom. And as you may have guessed, she likes me doing that to her. She tells me that she is proud to carry the marks of her Mistress's caning for the whole month, and begs me to cane her extremely hard to ensure that she is sufficiently marked to last her until the next time. We were mid-way through her session when we decided to have a swim. And now you have found us out Tom, again!"
Tom was massively turned on, and was delighted, yet embarrassed, that his cock was already recovering from its recent emptying. It was already half hard and he simpered a "Hello, Lily. Nice to see you again."
"Hello, Tom." Lily replied. "Nice to see you too. And to see you behaving as badly as ever. Your friends down at my massage parlour miss you, Tom, as do I, but I quite understand that our games together weren't to your liking. No hard feelings, Tom." She turned to Evelyn, "But Mistress, here we are naked and Tom is not. That doesn't seem fair." And without waiting, she approached tom and placed Evelyn's bikini pants over his head, effectively blindfolding him. His dick sprang to full attention as he felt her thumbs on the waistband of his shorts and drew them down to his ankles. He stepped out of them, mortified at now being exposed to two women at once. His two mistresses. But all that talk of caning had done for him and he knew it wouldn't be long before he was taking another himself.
"Lily has requested a further eighteen strokes of the cane, Tom. Would you like to watch me administer them?" Tom heard Evelyn's voice.
His erection swelled a little more and he stammered that he would like that very much. He was taken by the elbow and led into the house. He knew the layout and even before the door closed, the silence told him that he was in the Punishment Room.
His eyes were uncovered and the naked boy was ordered into the corner where he would not get in anybody's way. He could watch, they told him, because Lily wanted to watch him take his punishment too. His thumping hard-on was testimony that he wasn't averse to that idea.
"Mistress. You have already given me eighteen strokes of the cane, and now that we have had a swim, my ass has cooled down again. I know that when you give me the next eighteen strokes, it will be without warm-up and on top of the strokes I have already taken, it will be painful. However, I beg for no mercy. Please cane me very hard, Mistress."
"Are you sure, Lily? You know that I will do as you request, but we have never before broken off for a swim mid-caning. It really will hurt. A lot. And you know the rules; you must take your caning in complete silence. Any sound from your vocal cords will result in the stroke being repeated at the end of your requested eighteen. For extra strokes, you may scream as loudly as you like, knowing as we all do, that nobody will come to your rescue and that once I have you secured, you will only be released when I say so.
"Yes, Mistress. I know the rules and I accept them. Please tie me down securely. I will try to take my caning in silence."
Tom could barely believe his ears. This beautiful girl, his own previous mistress, was begging for a severe caning, and now she was climbing up onto the chair arms, spreading her knees wide and he could see her anus and her gaping pussy. Oh god, how he would love to bury his face in amongst that.
Tom couldn't believe his eyes this time, as Evelyn laid stroke upon stroke on poor Lily's buttocks. The lines turning a fiery red, and where they were now landing on previously caned skin, a dark blue. Evelyn caned her supplicant very hard, but Lily was made of stern stuff and it took until the thirteenth stroke for her gasps and wheezes and massive inhalations to become vocal.
"Ohhhhh!" she moaned as another strike resonated within the room. And then her apology. "I'm sorry Mistress. Please add another stroke."
