Lisa came over to him again and put her arms around his neck. Dan pulled her close and began a long, long kiss which eventually left them both breathless. When they broke apart she said, "I'm not going to wait another seven years for this, Dan. I'll be back next week to play games again, but I also intend to track you down some more this year, not wait until when we might get together again next summer."
"Don't worry. I'm not going to wait either. Remember I said you are more exciting than any fantasy I've ever dreamed up. I didn't really think of you as sexy when we were here years ago. I could never make that mistake again. You are the hottest, sexiest, most beautiful woman I've ever encountered. I'm not letting you get away that easily."
After another minute or so, Lisa broke the spell and called, "Come on, let's have a swim before lunch." She ran towards the pond, leaving Dan to remove his leather wrist cuffs before joining her.
After lunch the couple watched another of Dan's videos. When the tape ended Lisa said, "I still want you for my captive. In fact I think I'd like to try out a few things in the dungeon on you. Are you interested?"
Dan immediately crossed his wrists. "I am your to use and abuse, my captain."
The two made their way downstairs and into the secret dungeon once more. As they entered, Lisa's attitude changed. It wasn't anything obvious, but she was suddenly and definitely in charge. She placed wrist and ankle cuffs on Dan and clipped his hands behind his back. For a minute or two she stood looking around at all the devices in the room. Finally she decided on one of the padded sawhorses. She led Dan over to one end and had him spread his legs. She then fastened his ankles to each side of the A-frame end, spreading them about two feet apart. She released his bound hands and leaned him over along the length of the horse. His hands were then pulled down on either side and Lisa stretched him, fastening a wrist to either side of the A-frame at the other end.
Then she began to use her fingers to excite and tease. She let her finger tips lightly trace all over his body, across his chest, up and down his thighs, around his balls, and up the crack of his ass. Dan's breathing had become rapid and he was obviously reacting to her treatment. She pinched his nipples until they became hard and then placed a nipple clamp on each. After twisting and pulling each clamp a while, she added eight ounce lead weights. Stepping back she began to use a short tailed cat on his ass. Soon she was letting the blows roam, landing some on his back, some underhanded to his chest and stomach, around both the inside and outside of his thighs and occasionally allowing the tails to snap gently against his cock or balls. Dan squirmed and strained against his bonds, but his hardening member showed his mounting excitement.
Lisa selected a cat with somewhat longer and heavier tails and began to use this on Dan's ass. Her blows brought cries from his lips and left a network of red lines across his body. Sometimes she would stop the beating for a little while and tease his cock or tug on his nipple clamps. Twice she removed the clamps and reattached them at a different angle, bringing renewed pain. Then she resumed the whipping. After a particularly severe series of lashes, she stopped the whipping and picked up something. Dan couldn't tell what until he felt the cool lubricant on the end of her finger being applied to his open anus. Lisa played around the entrance and then began to move her finger in and out while twisting it back and forth. Dan had never really experienced anal stimulation like this but he found it unbelievably exciting. Then Lisa slowly removed her finger from where she had it deeply embedded in his rectum. Dan couldn't tell what she was doing and almost expected to feel a blow from the cat at any second. Then he once again felt cool lubricant at his rear entrance. But this time instead of her finger, the lube was on the end of a piece of plastic. The tip of the plastic slowly penetrated Dan and he almost became lost in this new and intense sensation. There was some pain but not too much as the slim object was slowly inserted and then partially removed to be reinserted a little deeper each time. Suddenly as the object penetrated deeper than it had anytime before, Dan felt Lisa's hands on his hips and her bare legs against his own. Now he realized what was happening. Lisa was using a strap-on on him! He had told her he would think about it, but she evidently decided not to wait, but to go ahead and try. He had to admit the sensation was extraordinary! He loved the way it felt when he fucked Lisa's ass and now he found he also loved it when she fucked his.
Gradually Lisa increased the speed and depth of her penetration. She also tugged and twisted at his nipple clamps and occasionally reached around to squeeze and rub his cock. Soon she was plunging quickly all the way in and out and Dan was pushing his ass back at her to help her get deeper. He could feel her tits against his back and the contact of her long, bare legs against his. For fifteen minutes or more Lisa kept up the pounding until finally Dan could take it no more and, with Lisa's hand wrapped around his cock, came in long, hard spurts. Lisa's climax came seconds later. But she didn't stop. She continued to fuck him for several more minutes until finally, after she had come herself twice more, she withdrew the dildo.
Dan held his breath while Lisa slowly pulled the dildo out. Then he let it out in a long sigh. "That was unbelievable! I never imagined how good that could feel. And to think I wasn't sure I wanted you to do it. Lisa, you can fuck me any time you want."
"It was rather extraordinary, wasn't it? I've never been on that side before, but now I think I understand why you like it so much. Feeling it slide inside you, opening you up, is an incredible turn on. I can only imagine how much better it feels for you since your cock is real. And having you helpless makes it even better. You really liked it, didn't you? Maybe I should have my crew of fifty use you."
"Yes, I loved it," Dan replied. "But I don't think I could handle your whole crew. Men aren't quite built for it like women. But I certainly wouldn't mind it once in a while."
"In that case, if you're all right..." Dan nodded. "Then I think I'll just have to find some way to punish you a little more." She ran her hands over his ass and along his sides finally tugging at the nipple clamps. She lifted the weights in her hands, taking the strain from his nipples. Then suddenly she dropped them causing Dan to cry out as the clamps pulled the weights up short. Lisa then started to finger his rectum once more, adding a little more lube. She took a medium sized butt plug and inserted the tip in Dan's ass. Slowly she pushed the device inside. This particular plug was about six inches long and spread to a maximum of an inch and a quarter before narrowing once again to less than half and inch. There was, of course, a flared base to prevent it going all the way inside. Lisa pushed the plug in until Dan cried out from the pain and then she let it back out a little. She repeated this again and again, each time forcing the plug a little deeper. The dildo she had used earlier when she was fucking him was about the same length, but only about three fourths of an inch across, so his anus still required quite a bit of stretching to accommodate the new intruder. Finally she gave the plug one very hard shove. Dan cried out as it felt like his ass was being split and then the plug popped inside and the pain subsided, leaving only a feeling of fullness.
Lisa used the cat to give his ass another dozen swats and then began to release him. As she removed the clamps and weights, Dan grimaced with the pain of returning blood, but didn't cry out. Lisa undid his wrist and ankle bonds and allowed him to stand. Dan stretched and moved around a little before Lisa said, "I'm not finished with you yet. Over here, Stud."
She led him over to a spot below two ceiling chains and attached his wrists, pulling them wide apart and high enough to almost raise him off his feet. She then used two ropes to pull his ankles about four feet apart and fastened them to rings in the floor. Dan was now forced to stand on his toes and take most of the strain with his arms.