She stopped outside the door, read the number and pulled the paper out of her bag. Yes, the numbers matched.
Pulling out a compact, she inspected her make-up. She smeared on a new thick layer of the blood red lipstick and pouted at the image looking back at her. The thick make up, heavy eyeliner and mascara made her look more like a mannequin than a live person.
She checked the seams of her stockings to make sure they were straight. This dude was sure as hell kinky. This outfit was straight out of some kind of 50's librarian's hell. The long tight black skirt had buttons running all the way up the back and the heavy tight jacket covered a nearly transparent white silk blouse. No bra, no panties, shaved pussy lips but he required she have pubes up above. She was glad she didn't go in for the clean shaved look.
And these shoes, they were positively freaking Victorian, heavy lace up with painful five inch heels. She pulled out the heavy square, black framed glasses and put them on. Her hair was in a tight bun on top of her head.
She suspected she was going in for a serious rough ride, but he was paying through the nose, money up front with a big bonus promised at the end if he liked her. One night with him meant the rest of the week off if she wanted.
She knocked on the door. A man’s voice called for her to enter, “You are late. I called for a steno hours ago.” He remained seated behind a huge black wooden desk. She looked him over. Not bad as far as Johns go. He looked clean and he wasn't fat or drunk.
His voice was soft and had a threatening tone. “I do not tolerate lateness. Come here.”
She felt a wave of nervousness. Her friend had set her up with this guy. She said he like to role play some pretty kinky stuff, there may be some rough stuff and toys but she had vouched that he was clean and wouldn't beat her up. He had sent the outfit and said she could keep it. Not that she had any use for ugly black wool suits.
“Sir, I was right on time.”
“Get your ass over here now!” His voice cracked like a whip.
She walked over to stand next to him. When she came around the edge of the huge black desk she could see he was sitting in a wheel chair. Jesus this guy was some kind of cripple. She wondered if he could get it up.
“Lean over the desk. Press your face to the top of it. Hold onto the far edge with both your hands.” She complied but turned her head so she could see what he was doing. “What the fuck are you looking at? I said press your fucking face to the desk.” His words were crude, but his tone still had that low scary tone. She turned her head to face down. She was a lot less nervous now that she knew he was in a wheel chair. She was sure she could get away if she needed to.
She felt him run his hand over her ass. “Nice and firm and round, I like round asses.” He slipped his hand lower down onto her calf and slowly ran his hand up the inside of her leg just as high as the top of her stocking. “Spread your legs apart, further, that’s good.”
She felt her calves tremble with the strain of the high heels, but she felt that uncomfortable shoes where going to be the least of her worries. The skirt was tight and she could not open her legs any wider. He continued to run his hands up and down the silk stockings. He did that for a really long time. She began to wonder if her friend had played some kind of joke on her. If this was all this guy wanted, she was cool with that. It even felt kind of nice in a weird way.
She knew that there was going to have to be more. He had hired her for the whole night. He was paying way over the going rate for most kinky scenes. He had been very specific about her being very clean, even to sending a specific type of enema he required she use before coming.
She tensed when he stopped stroking her legs. “Don't move.” He rolled away from her and went over to the only other door in the office. He opened it and she knew she was going to earn her pay tonight. Inside the door was an extra large full length mirror that reflected the whole desk. She could see her face reflected, the glasses crooked on her nose, a few wisps of hair coming loose from the bun on her head.
On shelves down low were a row of industrial looking dildos, neatly arranged by size from big to really big to fucking huge. She wasn't sure if she had ever seen a dildo that big before. A number of different sized paddles hung from pegs.
“I can't allow my secretaries to get into any bad habits. I think you will have to be spanked.” He rolled over and laid the paddle on the desk next to where her face was. He began to slowly unbutton the row of buttons on the skirt, one at a time. When all the buttons were undone he ordered in cold voice, “Stand up, and pull the skirt up until your whole ass is bare and then lay back down exactly the same as before.” She pulled the skirt up around her waist and lay back down her hands gripping the edge of the desk. She had had a couple of Johns who liked to spank her but never one with a fucking paddle before. She forced herself to think about the money.
He sat behind her for an eternity just looking at her ass. She knew that her cunt was completely exposed to but that didn't bother her. Go ahead look all you want. She thought to herself. “Spread your feet wider.” As she spread her feet apart she felt him roll close, the wheel chair supports of his legs slipping between her legs, his knees forcing between her legs. She thought to herself, going in for a close up view.
She felt his breath on her crack. She wondered briefly if he was going to go down on her. Some Johns liked that but none of them were any good at it. She would pretend to be grateful afterwards. She felt his hands spreading her cheeks and cunt lips. She could hear him inhaling deeply. He said something under his breath and rolled back.
“I expect you to lay still and take this. You may yell, cry and plead for mercy, but don't move. The more you take the better the pay at the end. If you want to stop just say, ‘games over,’ and we will move on to the next game. He reached for the paddle. The first swat was almost gentle. She lay still wondering how much she could get for letting him hit her really hard. He continued to paddle her each hit getting successively harder.
They were really starting to sting like hell. She gripped the edge of the desk and gritted her teeth. Finally a really sharp one popped her right up on her toes. She blurted out, “Son of a bitch.”
He hit her again, almost instantly, a lot harder. “I don't approve of my secretaries using such profanity.” She let out a sharp yell of pain. He continued to hit her hard, really hard. Each swat sounded like a rifle shot in her ears. She was up on her toes squalling with each one. It felt like he was beating her with a red hot frying pan.
Finally she could take no more. “Okay, Okay, Game over!” Her voice cracked and squealed. He instantly stopped, dropping the paddle to the floor breathing hard.
She lay panting on the desk top, absolutely drenched in sweat. “Did I do good?” She was a little surprised at the meek tone of her voice and that she on some level really wanted to please him.
“You did fine.” His hand gently stroked her ass. It stung but at the same time felt warm and soothing. Sweat ran down her legs. “Are you too hot?”
“Yes, it’s really hot.”
“You could take off that hot suit if you want. Leave on the blouse and the stockings. You can stand up to do it but stay by the desk facing the mirror.”
“Call me sir.”
“Thank you sir.” The suit was made of heavy wool and it was damp from her sweat. It was a little sticky to pull off. The thin silk blouse was soaked with her sweat and it stuck to her tits. Her nipples showed clearly through the nearly transparent material. In the mirror she could see that her make-up was smeared and the bun was coming loose. Strands of hair stuck to her face. She leaned down on the desk once more.
He opened a drawer. “Do you want a bottle of water?”
“Yes please, sir.”
He took the cap off and put it up on the table next to her. She lifted herself up on an elbow and took a deep drink. This getting spanked in a wool suit is thirsty work, she thought to herself. “Thank you, sir.” She lay back down and spread her legs back out wide again like he had her do before.
She was feeling kind of floaty and relaxed, even though her legs were trembling with fatigue. She felt him move close behind her again. Once more his hands began to stroke the nylon of her legs but this time he stroked up past the top of her stockings and ran up over her ass. Each stroke traced the edge of her pussy lips. She felt an odd frustration why didn't he get on with it. She realized she wanted to feel his fingers on her cunt. Damn this kinky John is getting me hot. Well, it’s his dime. She felt him lean in and inhale again. “You smell excited. You like being paddled.”
She was not sure if he wanted her to act innocent or slutty. “Sir, you make me feel things I have never felt before.” That was mostly true. Johns never turned her on as a rule.
He gripped her ass firmly and spread her cheeks wide and then moved his hands down to her upper thighs and pulled the skin forcing her cunt to open. “I can see you are getting wet.”
He ran his finger down the length of her crack, gently stroking up and down. She felt a shiver cascade down her spine. “Mmm... Oh sir that feels good.” He reached for something and she felt a cool liquid on her ass. He began to massage the inside of her legs and butt cheeks rubbing his smooth slippery fingers firmly against her, but not penetrating, never touching her cunt.
“You want me to touch your cunt?”
“Please, sir, only if you want to.”
“Touch your own cunt.”
She let go of the desk with one hand and slipped it down under herself. She spread the lips of her cunt so he could see everything and began to slowly rub her fingers up and down her slit. She could feel that a fair amount of the lube had run down and she was slippery wet. “Thank you, sir, for letting me touch myself.”
“There is extra pay for girls who come, the more you come the more you get. Don't fake it, I am back here with my nose practically up your ass. I will be able to tell.”
She began to rub herself with a little more determination. Money for coming, double bonus. She felt herself getting looser. She had had johns who paid to watch her play with herself. This was cake. She felt herself tensing her hips quivering and jerking. Just as she arched and shuddered, he pushed two fingers up her ass clear to the hilt, pushing back her climax. She grunted in frustration and frantically rubbed harder at her clit. He began to fuck his fingers in and out of her ass harder. Suddenly she arched and groaned coming hard around his fingers. She felt a soft spatter of liquid down her legs from her cunt clenching. “Jesus.”
He sat quietly behind her, his fingers still deep in her ass. “Nice one. I know a better way to do this.” He put some more lube on her ass, worked in deep and maneuvered his chair close behind her. “Sit down in lap. Slow, really slow. I will put my cock up your ass.”
She turned and looked. He was putting a condom over an amazing hard-on sticking up from his pants. It was fucking huge. He saw her eyes go large. “It’s not real, nothing like the wonders of science. It’s a fucking implant. It never goes away. We can play with it from now until doomsday.”
“Oh god sir, I have never had one that big up my ass before.”
“Look at it intellectually; you probably shit bigger than this. Your ass will take it. It may complain at first, but you and I both know with the right motivation we can get it up there. It would make me happy and it will make you money.”
She nodded and slowly began to lower her hips toward his lap. He put the head of that monster against her ass and began to pull her down onto it. It was not easy. She had to stop several times and fight the urge to yank away. But eventually she was seated firmly in his lap impaled deeply on his cock. “Good. That feels good to have my cock up your ass.” He bounced in his chair making her squeal.
“You can feel it?”
“Yes I have some sensation but it takes a lot to make me come, hence the games.” He reached down and snapped something on each side of his chair and folded down the arms. “Spread your legs wider, on the outside of my knees.” He gripped her thighs and spread them as wide as she could make them go. “Let’s roll over to the closet and see what we can find.”
He parked in front of the mirror. He began to unbutton her blouse. His hands were warm as the cupped her breasts. “Nice big nipples.” He rolled them between his fingers and began to tug them, short sharp little jerks. “Like the paddle, the more you can take the happier I will make you.”
She whimpered and gripped her knees, leaning her head back on his shoulder. His fingers twisted and yanked at her mercilessly, forcing cries from her lips until finally she gasped “Game over, please game over.” Tears dripped from her nose and cheeks.
He rolled the both of them closer to the closet. “On the top shelf are some gold colored chains. They are attached to some clamps, reach them down for me.
She was having trouble catching her breath. Her hands trembled violently. “But, sir, please, I said game over. My tits hurt too bad.”
“Just reach them down. They are adjustable. We'll let you decide how tight to make them.”
She gulped, nodded and reached up. She handed the shiny chains to him. On the end of the chain was a clamp with a screw adjustment. She looked again. There were too many. There were three clamps. Oh Jesus, he is going to put one of those things on my cunt. Think of the money. Think of the money.
Her nipples were rock hard, swollen and red. “Ready?” She nodded biting her lip. He put the clip on. It wasn't so bad, a sharp nagging pinch. “Tell me when to stop.” He began to slowly tighten.
She squirmed and whimpered as the pinch began to hurt. “Stop. Stop.”
“OK but if you want later we can try and tighten them more.”
He picked up the second one and repeated the process. She tried to take as much as she could but her tits still ached like mad from his assaults earlier. The gold chain hung between her nipples swinging gently as she flinched from the pain. A third chain hung down from the middle. The third clamp bumping ominously against her cunt. “Spread those legs nice and wide. Spread those cunt lips. Show me your clit.” He moved the chair close to the mirror.
She whimpered in fear. This guy was asking a whole hell of a lot. She reached down and spread her lips. “You put it on. Put it on your clit.”
She pressed the clamp open and closed it around her hard red clit. She hissed and wailed. “Oh god, oh my god.”
She squirmed and jerked, still impaled on the prong of his cock. His words were soft and demanding in her ear. “Tighten it. Reach down and turn the adjuster. Tighten it on your clit.”
“Oh god, I can't.”
“Yes, you can. You could take the paddle. You could take the pinches. You could take my cock up your ass. You can do this for me. Make me happy.”
She sobbed as she reached her hand down. She turned the adjuster a little bit. Pain lanced up and made her shudder. His voice was compelling. “Just one more time.” This time was worse; she let out a long wailing gasp as the teeth of the clamp bit deeper into her clit.
She lay back against his shoulder panting, trying somehow to adjust to the pain shooting up from her cunt. Her voice trembled with impotent rage, “You are a cruel bastard.”
His voice was simultaneously amused and threatening. “You have no idea. We have so many more things do to.” His hand reached around and grasped the chains connecting her clamps and gently tugged. She flinched and gasped. It hurt like hell but at the same time she could tell that it was turning her on too. He gave a firm bounce, reminding her of the huge cock anchoring her in his lap.
“Look at all those big cocks on the shelf. I bet your cunt feels empty. You want to fuck yourself with one of those don't you? Look at yourself in the mirror. You look beautiful but your cunt looks so empty and neglected.”
She looked in the mirror, mascara ran down her cheeks in black lines, her hair was completely down and plastered to her face, the heavy red lipstick was smeared around her lips. She blinked blearily at her swollen red nipples, and her gaping cunt, the moist folds bulged out obscenely. She thought to herself that he had not fucked her cunt and he was right. Even though she felt full to bursting with his cock up her ass, she still had that empty needy feeling.
She looked nervously at the dildos. There were five lined up in ascending size. The littlest one was damn big, at least eight inches and had a girth to it that she knew would stretch her. The others were intimidating. Each one was about an inch bigger than the next. The biggest was around twelve inches and she knew that there was no way she could wedge that monster into her cunt. She reached for the littlest one.
“Yeah, let’s start with that one.” She hefted it in her hand. It was heavy with a big handle to grab it by. “It has a vibrator in it. Turn it on. I will feel it when you fuck yourself with it.” She switched on the vibrations. It buzzed violently in her hand. It was a lot stronger than any vibrator she had ever felt before. It felt like it would turn her insides to mush.
“Push it in your cunt. Push it all the way in. Fuck yourself with it.”
She pressed the head of the dildo against her opening. It was big and nothing had entered into her cunt the whole night. She was tight. It was hard to get it in. She had to work it hard to force it in. She felt stretched wide. His cock had filled her up, and now this over sized dildo was stretching her even more.
His voice was excited and demanding. “Push it, push it in.” The sheer girth of the dildo forced her cunt lips to stretch, pulling the skin of her cunt tight against the clamp on her clit. The strong vibrations began to shake her whole cunt, her clit swelled against the teeth pinching it cruelly. The vibrations shook her whole pelvis, traveling up and making her tits vibrate. The clamps trembled on her nipples sending waves of pain and sweet lust shooting through her.
Suddenly she was coming, coming hard arching and screaming as wave after wave of agony and ecstasy shook her. He reached down and grabbed the handle of the dildo and began to pump it in and out of her fast and hard. “Fuck yes, come on me baby, squeeze your ass, dance in my lap, you fucking whore bitch.” He slammed the dildo in and out of her relentlessly. His other hand began to jerk on the chains holding the clamps. “Keep coming bitch.” She began to writhe on the cock up her ass, her head slamming back against his shoulder repeatedly as she convulsed over and over. He bit down on her shoulder and shuddered and groaned as he pumped his hot come deep in her ass.
He pulled the dildo from her and dropped it to the floor. He wrapped his arms around her gently. She laid limp and gasping for many minutes, his lips gently kissing her shoulders. Her voice was weak and wondering. “That was amazing. I have never come like that in my life.”
“You did really good. I want to do it again.”
“I don't know if I can.”
“Sure you can. The second time will be better. This implant keeps me hard. I can do this all night. I expect you will find out you can too. Do you want to tighten the clamps some more for me? Make me happy. I need you squirming and screaming.”
“Oh god, this is going to kill me.”
“I promise you will live through this. You will be walking funny for a while, but you will live. You will give me everything I want and more. You will make me very happy. Tighten the clamps.”
He was right. She did everything he wanted and more. She spent what seemed hours impaled on his cock, fucking herself with bigger and bigger dildos. Coming like a freight train over and over. She had his teeth marks up and down her shoulders as he bit her over and over. He promised her he would allow her to take off the clamps when she got the whole of the hugest dildo inside her cunt. They both had to push to get it inside her; she was groaning and shrieking as she watched the huge thing disappear inside her, her eyes locked on the mirror watching as his hands shoved it deeper and deeper, the deep grinding vibrations shaking her whole body.
“Good girl. Let’s take off these mean clamps.” She knew it would be painful when the blood came back. She braced herself as he reached up to release one of her nipples. She had totally underestimated this. She arched and shrieked, the pain washed through her. She instinctively tried to escape but his hands were iron strong holding her down on his lap. “Yes baby that’s better than you coming. You are doing great.”
He began to pump the monster dildo in and out of her. She didn't think she had the strength, but she felt herself beginning to clench around the huge plastic invader in her cunt, unable to resist the deep pounding vibrations shaking her womb and the clamp on her clit.
“Yes, baby, take it; feel this.” And he freed her other tit. She didn't know if she was coming or convulsing in agony. It all hit at once and he began to plunge the huge dildo into her and bounced hard forcing himself deep and hard into her ass. “Fuck yes, keep it up bitch. Keep coming.” He reached down and took the clamp off her clit.
She couldn't scream any more. She was rigid with agony and yet she was coming and coming. It didn't stop. He slammed the dildo into her over and over, her whole body spasmed and thrashed. A tiny part of her mind wondered if his cock could break off. He groaned, bit down on her neck hard and sucked the blood into his mouth as he came pulsing his come deep into her.
Much later as she came to herself, he murmured into her ear. “You have made me very happy.” He rolled over to the desk. “Grab the edge and lift yourself up. You will need to support yourself. Your legs might be a bit shaky. You can lie on the desk for a while if you need to.”
Her ass made a sucking sound as she pulled herself off his lap. His cock was dark purple but still looked just as hard and ready as it had before they had started.
“You have a very sweet ass.”
“I have never done anything anywhere as crazy as this before.”
“I do have an active imagination.”
He pulled a package of wet wipes out of a desk drawer and wiped himself off. He tossed the package onto the desk. “Help yourself.” She cleaned herself and pulled on the suit. He tossed an envelope on the desk. She looked inside. The stack of c-notes was impressive. This was so worth it.
“You want another date. I will give you my number.”
“Sorry baby, I need novelty. I need to see the surprise and protest in the woman's eyes. I need to see her take more than she ever thought she could. You have been there. You will not be able to give me that again. But if you know someone that you think could handle this kind of scene you can give her my number. Just don't tell her about the chair and leave her in the dark as far as what a cruel bastard I am. I want to surprise her.”
The Road to Recovery is Slow
2 hours ago