Linda Lost a Bet

'That was amazing. We need to get home soon.'

Linda hung up the call, stashed the phone back in her purse and left the fitting room.

"How did you do? Is there anything you like?" The clerk asked Linda as she approached the counter.

"I would like all three, please. Isn't there a sale going on for intimates right now?"

"Yes. Let me check to see if all these are on that promotion." The clerk scanned all the items in to the computer, typed a few things, and looked up at Linda. "Good news, these are all eligible. If you want to pick out a couple pair of panties, you can get those buy one get one as well."

Linda walked over to the display of panties and looked through what they had. She found a plain pair, in green, in her size and held on to them. She also found a thong in her size, in a white satiny material. She put those on the counter next to the bras. The clerk rang up the items and put them in a bag.

"That will be $78.49. Did you want to put that on your Maurice's card?"

"Here you go." Linda swiped her debit card, punched in her numbers and waited for the clerk to complete the sale.

"Receipt in the bag or with you?" The clerk held up the receipt.

"In the bag will be fine. Thank you." Linda grabbed the bag and started towards the door, Jack followed close behind. As Jack settled in behind the wheel, Linda grabbed his leg.

"We are going home now, right?"

"Yes, do not pass go, do not collect $200." Jack started the car and backed out of the space.

"Good. I have some things I need to take care of." Linda's hand slid up his pants to rest on his hard member. She gave it a good squeeze.

"Easy, I am trying to get us home. Don't make me turn your little device back on." Jack pulled his phone from his shirt pocket.

"Maybe that's not the worst idea you have had today." Linda wasn't sure if she could handle having that thing going again, but she wasn't sure if she wanted to be done with it yet.

At the next red light, Jack made good on his threat and started it back up on the low program. Linda moaned and grabbed her breast again, knowing it was dark enough in the car no one would see her. The trip home only took another 5 minutes, but Linda was enjoying every second of it. When they pulled in to the garage, Jack shut off the car but left the egg going. As he opened her door, he closed the garage door. Once the garage was closed, he offered his hand to help her out. She put in a decent effort to get out of the car while still riding the waves of pleasure from the egg inside her. Jack had to help her in the house and up the stairs to their bedroom. Linda quickly flopped on the bed, lost to the sensations washing over her. With her eyes closed and moaning from the vibrations, she didn't notice Jack moving around the room gathering a few select items. She didn't notice when he untied her shoes and pulled them off. It was only once he turned off the egg did she realize there were other items on the bed with her. She noticed her black pleated skirt on the bed along with the blindfold and the wrist and ankle cuffs. As she sat up, she also noticed her knee high black boots on the floor next to the bed.

"What is all this for?" Linda wasn't sure what Jack had in mind, but she was ready for just about anything. She had already had one orgasm and was working on a second when he stopped the show.

Jack reached for the wrist cuffs and motioned for her to raise her arms. She obliged and he fastened the cuffs to her wrists.

"Please stand up." Jack was speaking the tone he reserved for their bondage play. His voice became something she could not ignore or disobey. She stood up before she was fully aware she was going to, her body on autopilot at the moment. Jack reached down and undid the button on her jeans, pulled the zipper down its length and slid his thumbs into the waistband. In one smooth movement he slid the jeans down her legs to pool at her feet. He knelt down and placed his hand on the back of her left knee, indicating for her to lift that leg so he could remove it from that pant leg. He repeated the process on her right leg. He handed her the skirt.

"Please put that on." Linda undid the catch and zipper on the side of the skirt, stepped in to in and slid it up her legs. As she pulled the zipper back up and closed the catch, he reached for the ankle cuffs on the bed. He knelt down again, picked up a boot and helped her slide her foot into it. He helped her with the other boot as well. Once the boots were on and zippered, he took each cuff and strapped it around the boot at her ankles. Since the boots fit her snugly, she could almost feel the cuffs though the boots.

He clipped her wrists together with a carabiner he pulled out of his pocket.

"Please follow me."

Jack led her out of the bedroom, down the steps to their kitchen, then around the corner to the basement door. Jack opened that door and motioned for her to go down the steps. Her boots only had a small heel on them, but she grabbed the railing anyway. With her wrists clipped together it made the journey a little awkward. Once they reached the bottom, Jack led the way again. He led her towards his workbench, but moved her away from it. He turned her to face the bench and that's when Linda saw their toy bag sitting on the bench, along with a few lengths of rope. Before she could react, he took the blindfold from his pocket and slid it over her head, covering her eyes. She couldn't see anything he was doing from that point on.

"Now for the rest of the evening. You will likely be blindfolded for the remainder of the night. Please relax and enjoy yourself."

She was blind and had to rely on her remaining senses. She could hear Jack over near the bench, it sounded like he was doing something with the rope. After a few moments she felt his hands on her wrists. He unclipped her wrists, but then attached rope to each cuff. She sensed him above her somehow and heard the rope running through some kind of hook or something. Suddenly her right arm was being pulled up and away from her. The sound came again on her left and that arm was pulled up as well. She heard him messing with the rope again and once the sound stopped, she pulled on her arms. They were spread out above her, but they didn't move when she tugged on them. She felt Jack tap on her left leg.

"Step out some please." Linda moved her left leg out as best she could. He also tapped on her right leg and she moved that one as well. He tapped again lightly on her left leg, indicating that she needed to move more. Once she obliged, she felt him clip something to the cuff on her left leg, then her right leg. She thought she heard him stand back up and she tried to close her legs. She realized she couldn't. Jack had used one of his home made spreader bars to keep her legs apart. Linda had a mental picture of how she must look at the moment. Still fully dressed and spread eagle in the basement, she must have made quite a sight. During all this, she had forgotten about the little egg still inside her. When it came back to life, it surprised her and she called out.

"Oh! I forgot about that. Jack, with me spread out like this, I hope it doesn't fall out."

Jack walked up to her and began to massage her breasts through her shirt. His mouth found hers, their tongues began to twist and war with each other. The kiss was one of the most passionate they had shared. His hand caressed the back of her head, while another hand made its way down her back to squeeze and massage her ass. After a moment he broke the kiss, leaving them both breathless.

"God you look amazing like this." Jack continued to let his hands wander around her body. This continued for what felt like minutes. Linda was lost to his hands and the egg and her bonds. Suddenly his hands left and she felt lost without his touch. Jack reached out and started to unbutton her shirt. Once the shirt was fully opened, Linda remembered the shelf bra. Her nipples were on display and Jack took full advantage. He sucked one nipple into his mouth and his hand found the other. He touched and licked and teased her, letting her get very aroused.

"Now, not so fast. I have a few things planned." Jack walked away leaving her bereft. She heard him open a zipper. It sounded like he was digging around in the toy bag, and she heard him place things on the bench. He must have found what he was looking for because the sound stopped. She felt his hand on her nipple again, only this time he left one of the nipple clamps behind. He put the other clamp of her other nipple and let the connection chain swing a little. This made the clamps dance a little on her nipples, causing the sensations to move and change. She heard him go back to the bench and pick up something else. He moved behind her and lifted her skirt up, tucking in into its own waistband. He rubbed her ass and pulled the panties to the side, exposing her little rosebud. She heard the cap on the lube and felt the cool sensation of the slippery concoction run down the crack of her ass. His hands rubbed the lube on her crack and around her hole. With a little more lube, his finger entered her tight pucker and plunged all the way in. He moved the finger in and out a few times, then pulled it back out. He quickly replaced it with something larger and more solid. She could feel the plug stretch her out, but before it became uncomfortable, it slid over the largest part and moved inside her easily. Once he was satisfied with the plug, he pulled her panties back in place and let her skirt fall back down. With the plug in her ass and the egg slowly vibrating inside her pussy, Linda was slowly being driven over the edge.

Jack pulled on the nipple clamp chain again, the pain mixed with the pleasure from the egg and created confusion in Linda's mind. She wasn't sure if she should react to the pain in her nipples or the pleasure in her pussy. While she struggled with that, Jack turned off the egg.

"Oh, I was getting close Jack." Linda heard the whine in her voice but didn't care. After the night she had, she was ready to cum again.

"I know Dear. I want you to savor it, enjoy it. I want you to have orgasms like you never had before."

Linda heard him use the plural, orgasms. How long was he going to keep her like this? As a sort of answer, the egg sprang back to life, at a higher setting. She became aware of the plug in her ass again, enjoyed how it filled her up with the egg in her pussy. She hadn't noticed Jack walk away again and was surprised when she heard the vibrator buzz away and felt the front of her skirt lift. When Jack touched that toy to her sensitive clit, she came hard, screaming out his name.

"Oh My God Jack!" Linda thrashed about in her bondage, twisting from the force of her climax. The orgasm went on and on, Linda feared she might pass out. She knew she was having trouble standing and wished Jack would just let her sit down. He must have sensed her shakiness because he grabbed her around her waist and held her to prevent her falling. After what seemed like an eternity she started to come down from her ecstasy high. Jack turned off the vibrator and egg but continued to hold her.

"Are you steady now?" Jack let her rest for a brief moment while he continued to hold her against him. She realized he was also still fully dressed, she could feel his pants against her leg and his shirt against her bare chest.

"I think I am ok now." Linda managed to straighten her legs and hold herself up.

"Do you want a minute to recover or shall we continue?" She could hear the smirk he surely had on his face.

"Let me have just a minute. I suppose you won't let me sit will you?"

"Not yet, my lovely. Besides, I don't think you want to try sitting down at the moment." He reached behind her and tapped the plug still firmly in her back side. Linda took a few moments to calm down and regain her senses. She felt Jack release her ankles from the spreader bar and she pulled her legs closed in response. Jack slid his hands up her legs, past the hem of her skirt and grabbed the waistband of her panties. He slowly teased them down off her hips and down her legs to pool at her feet. He grabbed the back of her knee again and helped her step out of the boy shorts. Before he stood back up, he grabbed the tail of her little egg and gently pulled, removing it from her now sopping entrance. The feeling of it coming out sent a rush through Linda, causing her to shiver briefly.

"I hope you aren't cold. I have more for you."

"No, just it felt weird when you pulled out that egg. I guess I wasn't expecting it."

"Ok. Let me know if something hurts, I'm not trying to hurt you."

"Yes, I know. I am Ok so far." Linda wasn't sure what else he had in mind, but she did just have a monstrous orgasm. If he was going to do that again, she might not mind a little pain with it. She heard him over at the bench again, then behind her. The sound of rope pulled through some kind of anchor hit her ears again, similar to when he tied her arms up. She felt him reach between her legs and she parted them instinctively to allow him access. Then she heard the same sound of rope being pulled in front of her. Suddenly she felt rope between her legs, pulling up her skirt. She tried to close her legs against it, but it was to late. The rope slid up between her ass cheeks and started to pull in between the lips of her pussy. As it pulled harder, she felt it grind on her clit. As Jack pulled it tight and tied it off, she could feel each movement through the rope rubbing against her sensitive nub. Linda wasn't sure what to make of this strange feeling, but her body knew. Before she could stop, her hips began to move. This made the rope grind against her clit, sending waves of pleasure mixed with a little pain from the pressure. As she moved, the chain on her nipple clamps moved as well, waking up her chest. The more she ground her hips, the more it felt good, but the more it caused the nipple clamps to sway and cause discomfort. Jack let her move and sway for a bit, then he reached behind her and hit the button to turn on the vibrating butt plug.

"Oh God, I didn't know it did that." Linda almost jumped when the plug started up, which made the clamps bounce and the rope moved in a new manner. The whole of the sensations pushed Linda closer to another climax. As she writhed in her bondage, Jack sat back and watched. Linda was moving quite a bit, the rope causing sweet friction on her clit, the clamps pulling and pinching her nipples and the plug sending vibrations through her ass. After a while, Linda felt the tension increase on the rope. Jack must be pulling on it. This pushed harder on her sensitive nub, causing more discomfort. All of a sudden, the rope began to vibrate. Jack took their big vibrator and held it against the rope close to her body, sending the vibrations down the rope to tease her once again. The vibrations started to work their magic on Linda, sending her towards her third orgasm of the night. Jack massaged her tits as he held the vibe against the rope, Linda continued to grind and move. Her motions became more urgent, Linda was getting closer to orgasm. Jack let go of her breasts, allowing the clamps to move on their own. He turned up the vibe to high and watched as Linda writhed on the rope between her legs. From the vibe, the pressure of the rope and the plug, Linda began shaking as her orgasm hit.

"Ahhh, hmm, ohhh" Linda lost words as she came hard, moaning loudly and grinding hard on the rope. She let go to the waves of pleasure washing over her, her legs threatening to buckle. Jack realized this and put down the vibe as he held her one again. She didn't even realize he was there, she rode the waves of her orgasm as it hit again and again. She finally came back to reality and felt the rope was gone from between her legs and the plug in her butt was silent once again. Jack was holding her to stop her from falling in her bonds. The cuffs she had on her wrists were not meant to hold her full weight.

"Are you back with me?" Linda could hear the concern in Jack's question. She knew he wasn't scared, but he was definitely a little worried.

"Mmmm. Maybe. Are you going to do that again? I don't think I can take another standing up."

"Just one more. Can you try, for me?" Linda wasn't sure if she could, but she wanted to try for her lover. He had given her three orgasms tonight, all three were amazing. She thought she could last for a little bit longer.

"Yes, but be nice. I am almost worn out." Linda summoned strength to stand on her own, her legs were a little shaky. She felt the ropes holding her arms let go and she allowed them to drop to her sides, the ropes getting pulled from the cuffs. Jack took her wrists in his hands, brought them together in front of her and attached the carabiner from earlier. Linda felt her arms, now hooked together, being pulled up once again. This time, they didn't go all the way up, she was able to leave them bent at the elbow. Jack reached behind her and lifted her skirt again. He left her like this for a minute as she heard him rustle around behind her. She felt his hand on her back, gently coaxing her to bend over at the waist. Linda complied and she felt him start to gently pull the plug from her ass. Before she could get used to the feeling of being empty, she felt something warm push at her tender rosebud. He meant to fuck her ass! The coolness of the lube contrasted with the heat of his erection. Because she had just had the plug back there and because of the extra lube he had just applied, his dick slid in fairly easily.

"Ah, be careful. Please." They had tried anal before a couple times and Linda didn't hate it, but this was unexpected.

Jack slowly pushed in to her until she felt his balls touch the back of her legs. He was buried in her ass to the hilt. Linda felt his entire length inside her, he began to slowly pull back out. When his head reached the tight ring inside her ass, he moved back in. He was slowly fucking her ass. Linda was quickly getting used to the feeling of him there and was starting to enjoy it. It felt strange to her still, but it was becoming more enjoyable. Maybe it was the events of the evening so far, maybe it just felt good, but Linda thought she might orgasm again. His pace remained slow, she was getting used to him being there. Linda could feel her pussy tighten in response to her growing arousal. Jack increased his pace, adding a little more lube as he did. Linda could feel the chain on her nipples swinging, her bent over posture causing it, increasing her pleasure oddly enough. She felt Jack reach between her legs and start to massage her clit, sending her desire into overdrive. If he kept that up, she would surely orgasm, and sooner rather than later. As he continued the slow assault on her tender backside, his fingers danced on her nub. Linda felt the orgasm start and didn't make an attempt to stop it. Her head flew back and a load moan escaped her mouth, her pussy and ass clenching. The feeling of him still in her ass was different, but still heightened her climax. Jack slowed down his pace during her climax, maybe because she had clamped down so hard he couldn't move. As she began to relax, Jack picked up the pace. He was starting to move faster, she could hear him grunting from the exertion.

"Ah. Oh God!" She heard Jack cry out and knew he was coming soon. His fingers still played over her clit and the fast pace of his fucking drove Linda towards another orgasm. Suddenly Jack pushed hard in to her all the way, she felt his cum splash inside her bowels. This sent her over the edge into another orgasm. As they climaxed together, Linda lost control of her legs. Jack grabbed her hips to keep her on her feet, his dick still inside her holding her up as well.

"Oh my God, Jack. I can't. Just can't anymore." Linda was breathless and exhausted.