Molly And James

Molly parked her car in the driveway of a modest house in a nice suburban development. The houses were mostly brick with nicely manicured lawns on half-acre lots typical of most modern developments. She had never been to James' house before. Molly had been seeing James for about a month. She met him through a friend at work. He was very different from the guys Molly usually dated. She couldn't quite put her finger on it. He had an uncanny knack for seeming to know what she was thinking and there was something mysterious about him. They had been out a few times for dinner, drinks and movies – typical dates. She enjoyed his company and he made her laugh. He was a little over 6 foot tall with wavy black hair and a face that was maybe a bit too angular to call handsome. He kept himself in shape and he worked for a computer-consulting firm. A good job was always a plus in this environment. She was secretly hoping things would develop further.

Molly was meeting him at his house after work and then they were going to meet some friends from her work for dinner and drinks. His house was closer to the bar so she was going to leave her car there while he drove. She parked her car behind his black Jaguar. The garage door was open and James was moving around in the back. The garage was very clean with things hung neatly on the walls or in shelving. The floor was painted a light grey and looked very clean for a garage. James was moving around a strange looking wooden platform making some adjustments to things.

"Hi, Molly." He said coming over to give her a quick, friendly hug. " I wasn't expecting you so soon."

"I got off work a bit early. What's that you're working on?"

"Oh, this." James hesitated "It's for a friend. It's kind of complicated to explain, so lets just say its part of a bet."

"Sounds mysterious." Molly laughed, "Do you have somewhere I can change out of these work clothes?"

"I'm sorry. How rude of me. Come on in." James waved her inside the garage door that led to a mudroom off a modern looking kitchen. The kitchen was at least a little messy so apparently James wasn't a complete neat freak.

"There is a bathroom right there on the left, and there is a guest room down at the end of the hall there that will probably give you a bit more room to get changed." James pointed down the hall to a door that was half open on the right. Molly walked down the hall, swaying her hips a bit more just for fun and to see if she could get a reaction. She glanced over her shoulder and saw James glance away. He had been watching her she smiled to herself.

Molly closed the door, took off her work clothes and changed in to a pair of tight fitting jeans and a white silk button down shirt. She was about 5'5" with full breasts and more curves than she would like, but they seemed to get guys attention. She had clear, pale skin with shoulder length, dark hair, somewhere between brown and black, and bright blue eyes. She always thought her face was pretty. She freshened up her makeup, slipped on a pair of low platform heels and checked herself in the mirror. She unbuttoned one more button on her shirt to show a hint of cleavage, then folded her clothes back into her bag and went out to find James.

He was back in the garage still puttering around the platform. He was also wearing jeans and a dark green, button-down shirt. He had the sleeves rolled up to his elbows and she could see the muscle definition in his arms. He looked up when she came through the open door from the mudroom, giving her an admiring up and down glance before saying "You look great."

"Thanks. Ok, so what is the deal with this thing that has all your attention?"

"It's not that easy to explain. My friend Dave sort of dragged me into this bet, saying that I could devise something where he could secure his girlfriend Dawn with just this string." He held up some innocuous looking white string. "I'm not sure how the conversation started, but it has been an ongoing thing back and forth between them for a while now, and Dave's been bugging me, so I decided to do it. It's finished now – I think."

"Seems like a strange bet. Why would someone bet that?" Molly asked innocently.

"You would have to know them." James replied smiling.

"Why don't you try it out on me?" She asked playfully. James got a strange look on his face.

"That's probably not a good idea." He replied nervously.

"Oh come on. We have time. What's the worst that could happen? I don't think this thing will work." Molly challenged, now wanting to know more about this platform.

'What's the worst that could happen?' James thought to himself. She will run out of her screaming and never want to see me again. Then again, if things work out, it would open up all sorts of possibilities.

"OK. If you insist. But remember, whatever happens, you asked for it. Slip your shoes off and climb up on your hands and knees, head this way." He helped her up on the platform. It was a rectangular piece of wood roughly 2' x 4', that had some padding over the top. There was a wooden post on the backside that came straight up about 3' with a metal pipe sticking out over the platform. The platform was on some type of roller that made it tilt back and forth like a seesaw. It tilted forward as Molly climbed on so that most of her weight seemed to be on her hands. The pipe was about a foot over her back.

"Now hold still for just a couple of seconds while I secure the string." He gathered her hair in a loose ponytail and looped some of the string around her hair, pulling it tightly and tying it off. The string was a heavy-duty kite string, so although it looked thin, it was actually quite strong and would not break easily. He took both ends of the cord and looped it over the pipe. He threaded the ends through a tensioner and then looped another piece of cord through a large, smooth, polished hook he placed through the belt loop on Molly's jeans and tied that to the tensioner as well. He pulled the cord through the tensioner pulling on Molly's hair and her jeans so that her head and shoulders were pulled back. Molly shifted a bit to get more comfortable.

"Ooh, that tickles." She squirmed as he looped the thin cord around each of her big toes. Her head was still bent back and was starting to get a little uncomfortable. She was still confident that there was no way he was going to be able to tie her down to this platform with that string as she could just roll to the side and sit up at this point. It seemed like James was going to lose his bet.

James had taken each cord and passed it through an in line tensioner under the platform and now had made little slipknots in the end of each one. He was going to have to be quick with this next part before Molly could free herself. There would be no going back after the next step. He took up another inch of slack with her hair bending her head back a little more.

"Ouch. That hurts. Can you loosen that a . . . Stop! Oh my god what do you think you're doing?"

James had moved around to the front of the platform and brought the two cords up through small pulleys on the front of the platform. Molly was straining to see what he was doing while she was talking and he very calmly reached into her shirt and bra, pulling her right breast out and looping the slip knot over her very erect nipple, and then quickly doing the same for the left breast. Molly reflexively tried to reach up with her hands to stop him but when she took her hands from the platform, it put all her weight on her hair and neck. It hurt and she felt like she was falling so she put her hands back down to steady herself. This gave James the time to tighten the tensioners under the platform, taking up all the slack in the cord and pulling on Molly's nipples.

"Owwwww. James, what the hell do you think you're doing? Let me up. This isn't funny." Molly was beyond shocked at this point and was now actively struggling to get free.

"I thought you said there was no way I could tie you down to this platform using that hook and the string. I'm done, you can get up now." James smiled as he circled the platform. The bulge in his pants was growing. Molly looked incredibly hot; her head was bent back with her hair secured over a pipe to the hook that was looped though her belt loop on her jeans. Her breasts were out of her shirt and bra and were pulled downward by her nipples attached to the cord that ran under the platform and was then secured around the big toe of each of her bare feet.

She tried to move her feet to get to be able to stand but when she did the cord pulled painfully on her nipples. When she tried to move her hands to her breasts to release the twine it put more pressure on her hair and neck and she couldn't see to get the twine off. James saw that she might eventually be successful with this strategy so he looped another piece of twine around the thumbs of each of her hands and then around one of the pulleys on the front of the platform. Now she couldn't get her hands to her breasts.

Molly couldn't believe what had just happened. She was shocked that James had just calmly manhandled her breasts and she was frustrated that she could not get loose. Everything she did put pressure on her nipples, which were burning. On top of that, she found herself incredibly aroused by her predicament, and she was embarrassed that James might notice.

"Ok. You win. I give up. I can't get loose." Molly said quickly hoping to end this and redeem whatever modesty she might have left.

"Oh. I think you're giving up much too soon." James said as he walked around behind her. Molly's ass looked great with her jeans stretched tight as she leaned forward. Molly was so wet that she was starting to develop a wet spot between her legs, a fact that did not go unnoticed. James decided that he was going to satisfy Molly's curiosity once and for all. After all, there was no going back now. He tickled the soles of her feet with his fingers as he walked around her, taking in her beauty. She squirmed and gasped when she curled her toes and it pulled more on her nipples.

"To get the full effect, you really should be naked. That was how it was intended to be used." James said as he came back towards Molly's head.

"No way, mmmpff." Molly started to protest before James took advantage of her opening her mouth to insert a ball gag. He looped it around the back of her head and fastened it securely. Her eyes went wide open as she felt him start to unbutton her blouse. She struggled in vain, every move tugging more on her sore nipples. He reached up and unsnapped her bra, letting her breasts hang free. This took some of the pressure off her nipples for just a minute, but he tightened the cords quickly to take up the extra slack. He stroked the sides of Molly's breasts softly, causing her to squirm and suck in her breath sharply around the ball gag.

Molly was torn. She was absolutely mortified that James was disrobing her and had her tied down to the table in such a compromising position. At the same time, she was incredibly turned on. Her pussy was soaked; she could feel her lips rubbing together under her jeans. The pain in her nipples had given way to a warm, burning sensation throughout her breasts that was moving down to her stomach and lower. She was trying to figure out how she was going to get loose and figured she would have her chance when he tried to take off her pants.

James grabbed one of her hands and removed the cord from her thumb. He held her hand firmly as she struggled, no match for his strength in the position she was in. He brought it back behind her and slid her blouse and her bra over the arm. He did the same with the other arm and then retied her thumbs together behind her back. Now all of her weight was on her hair. She had to tighten her core muscles to help hold herself up to take pressure off her hair and her nipples.

James was enjoying unwrapping Molly. Her pale skin was starting to sweat as she struggled with her position. Her breathing was heavier and her skin was getting flushed. He was gaining an appreciation for how beautiful she was. He realized that getting Molly's pants off was going to be a challenge as well. He needed a distraction. So he walked over to the wall and brought back a small cane.

"Have you ever been caned, Molly?" He asked innocently as he held it in front of her. She shook her head no and he saw some fear in her eyes as the realization of what he was asking sunk in. He brought the cane down on her covered ass firmly –causing her to jump, pulling on her hair and nipples. She screamed around the gag as he struck her ass a few more times. She quickly figured out she had to brace herself and hold as still as possible to minimize the pain. It really didn't hurt that bad through her jeans, it was more the surprise.

She was breathing heavier, her nostrils flaring, her body sweating now with the exertion. James unexpectedly brought the cane down firmly on one bare sole and then the other. The was a second delay before a searing pain shot up her legs and she jerked both feet hard, pulling hard on her nipples. Tears were flowing freely now as she couldn't believe how much the soles of her feet hurt. Her mind was not focusing and she blindly obeyed when James told her to hold still. She felt the pressure let off her hair and neck and she slumped forward, relieving the pressure on her nipples. Her hands were still tied behind her so she struggled to figure out how to hold herself up and not collapse on her face since she was leaning forward.

James had reached around and undone the button and zipper to her jeans. He took the hook out of her belt loop and then pulled her jeans and her panties down to mid-thigh. Molly couldn't stand because the cord still held her nipples and she struggled ineffectively. James grabbed the hook with his left hand and then dipped two fingers into Molly's soaking snatch, bringing some of her natural fluids up to cover her little rosebud. She struggled harder when he quickly slid a finger into her ass lubricating it quickly in preparation for the hook. He then slid the blunt end of the hook into her ass and tensioned the cord attached to her hair. Molly tried to scream around the gag at the new invasion. She had never had anything in her ass before and it hurt a little, but not as much as she thought. Now not only was her hair being pulled on but her ass was being pulled and stretched at the same time forcing her to arch her back uncomfortably.

As Molly struggled to adjust to her new situation, James took advantage and untied her toes, allowing him to continue to slide her jeans off her legs. He only freed one nipple at a time so she couldn't really stop him. He then took her arms from behind her back and put them back on the platform in front of her. She was now resigned to James seeing her naked and bound. She was not really thinking at this point, her body was just reacting. The magnitude of what was happening overwhelmed her. She used her arms to finally take pressure off her hair, nipples and ass. Her body was shaking with the exertion. She was incredibly turned on. He smacked her bare ass hard on each side making her jerk and move. Her juices were now dripping down the insides of her thighs. She had adjusted to something being in her ass and surprisingly that was starting to feel good as well. She couldn't believe she was getting so turned on by being stripped and tied to a platform like this. She had gotten past the humiliation quickly and now was getting turned on by the idea of being so naughty. She felt her juices dripping down the insides of her thighs. She was covered in a sheen of sweat, and her breathing was labored. Her nipples were on fire, the initial pain had been replacing by a burning sensation that seemed to shoot directly to her pussy. Even though she was naked, her body felt warm. She found herself having a hard time focusing with all the new sensations. She couldn't move without feeling a tug on her nipples or the hook in her ass.

She heard a buzzing noise behind her, but she couldn't turn to see what James was doing next. She felt something push between her legs and then felt what must be a vibrator slide between her thighs and held right at the entrance to her pussy. If he would just push it a little farther to her clit, she knew she would explode. She tried squeezing her thighs together and arching her back more to bring her clit in contact with the vibe, but it pulled back just out of reach. James started slapping her ass, alternating between each cheek. It started soft and didn't really hurt, but each one made her involuntarily clench a bit, squeezing the hook in her ass and tightening her thighs around the vibe. He was slowly increasing the pressure of the slaps and she felt her ass begin to burn. She was so close to cumming. Her whole body felt like it was on fire. It felt like James was really spanking her hard now, but she barely felt it. Then her world exploded.

James pulled hard on the cords on her nipples, stretching them painfully and then pulling them off altogether. Molly screamed around the ball gag as a searing pain shot through her nipples bringing her quickly back into focus. She started to reach for her breasts with her hands to soothe them when the vibrator slid forward and pressed hard on her clit. Her body convulsed as the most powerful orgasm she had ever experienced crashed over her body. Her thighs clamped together, her stomach muscles rippled and she felt herself arch back even a little bit more. Waves of pleasure spread out from her clit. Twenty seconds seemed like two hours and then the vibe slid out from between her thighs. Her body slumped forward on to her hands and knees. She was still shaking. She was drooling around the gag and her legs were soaked. A small part of her brain was worried she had peed herself, but she couldn't really do much about it now.

James slid a couple of large pillows under her stomach and loosened her hair allowing her to slump forward. He was stroking the sides of her breasts and she realized he was talking to her.

"I realize that was a lot more than what you were expecting, but you seemed to enjoy it so much I didn't want to stop. I hope you will eventually forgive me."

Molly was absently moving her head up and down in a "yes" motion. James loosened and removed the ball gag. "Do you want me to fuck you Molly?" He said as he pulled it out of her mouth.

"Yes" Was that her voice. Molly couldn't believe what she was agreeing to, but her body was aching so much and she just wanted something inside her. She did want things to progress with James, but she had never in a million years imagined this.

"Ask nicely Molly. Where are your manners?" James said as he struck a light blow with the cane to the side of Molly's breast. Molly flinched, but didn't cry out.

"Please fuck me, sir." She added the last because it seemed right. Molly's mind was swirling. She couldn't believe how incredibly turned on she was and she felt like she would cum again the minute he filled her.

"Since you asked so nice," James smiled as he watched Molly give in to the moment. "But first, you have to get me ready." The next thing Molly knew James's hard cock was sliding into her mouth. He was a little bigger than what she was used to, but she didn't have any trouble taking about half of him into her mouth right from the start. She sucked and used her tongue and tried to do everything she could to return some of the pleasure he had just given her. He grew thicker in her mouth and she felt him grab the back of her head and pull her forward. He got about ¾ of the way in before she started to gag a little. He held her there for a few seconds and she felt her eyes water and her nostrils flare as she tried to breathe around him.