by Golden Angel
Michael stood in front of her looking stern.
“From now on you will finish your work, no matter your distraction. And I know how much you enjoyed your spanking last night, which is why your punishment today is so much harsher.” He reached up and caressed her breast, she shifted uncomfortable on the wood, trying to find a way to relieve the squashed pressure on her pussy. Despite the discomfort she could feel herself getting wet.
"Be a good girl now, don't make any noise." Diane nodded. Trepidation filled her as he walked over to the wall and picked up a small rubber whip.
Beginning by slapping her body lightly, the whip almost felt pleasant as the many rubber strands wrapped around her body stinging lightly but pleasantly, making her skin pinken. The slaps became slightly harder, wrapping around her stomach, waist and boobs. Several times he hit so that the ends of the strands whipped around her breasts like it was cupping them to smack her nipples. Keeping back her moans she tried to keep her movement to a minimum as the wood pressed into her center, intensifying the whipping. Speed and intensity picking up Michael began concentrating a lot of the strikes onto her ass and breasts, heating them with the stinging sensation produced by the whip.
After her breasts and ass were turned a bright pink and there were small whip marks over her stomach and back where the end of the whip strands had hit, Michael hung the whip back up and picked up a riding crop. Diane was gasping and glistening with sweat, her pussy was aching even more than the rest of her body and she desperately wanted to get off of the wood.
"You were a good girl, so it's only going to be 10 hits with the crop." he smiled. Despite the groan she let out she couldn’t help smiling back, a thrill going through her when he told her that she’d been a good girl. "You can make noise if you need to."
It was a good thing that he'd left that open to her, because as the first hit connected with her ass she shrieked, and jerked, which made her groan in pain as her pussy was pushed harder onto the triangle that was mashing into it.
THWACK! Another stripe, laid in an X shape across the first one.
THWAK! THWAK! THWAK! Five stripes were laid across her ass, leaving upraised reddened outlines. Diane sobbed and squirmed, the stripes across her ass burning, the sore throbbing in her pussy was beaten back for a moment, but still present.
Then Michael moved around to the front of her.
THWACK! THWACK! THWACK! THWACK!
Screams erupted from her as the crop moved quickly over her already pinkened breasts. There was a short moment where Michael allowed her to catch her breath, and then THWACK!!!!! She jumped and screamed as the flat of the crop hit squarely across both her nipples, causing them to redden and jut out in shock and pain. She gasped and struggled as the jump caused her pussy to slightly lift from the wood and then drop back onto it, mashing the tender folds of her pussy lips. Writhing, her thighs squeezed together around the wood, trying to push herself back off.
A strong arm wrapped around her and lifted her slightly and she felt a few tears fall down her face in relief, the agonized throbbing in her pussy becoming even more apparent as the marks on her breasts and ass burned. Diane barely moved as Michael untied her hands from the rope above her head murmuring that she was a good girl. Her body slid off the triangular horse into his arms, leaving behind a very wet spot on the wood where her pussy had rested. Tears leaked from closed eyes and every line of her body quivered in exhaustion. Carrying her over to the carpeted part of the floor, Michael laid her down and kissed her lips as he began moving his dick into her pussy.
The burning pressure he caused in her already crushed pussy caused Diane to wake up a little, her eyes flew open and she tried to push at the body on top of her. Michael just chuckled at her feeble attempts at removing him, and grasped her bound wrists in one of his hands, pushing them above her head as he slid home. Moving slowly, carefully, he sank each inch of his dick into her, gently resting his body against her bruised lips. Kissing her lips, he waited until he felt her relax beneath him before he began pumping in and out of her abused pussy as she moaned and squirmed beneath him. His movements began picking up speed, rubbing over her crushed clit, and adeptly pulling feelings of pleasure out of her protesting body.
Pain and pleasure jangled her nerves, she writhed beneath him as he leaned into the strokes, throaty cries of pained pleasure echoing in the room. Her thighs squeezed, trying to keep him from her, but he was much stronger than her and he pressed through. The stripes on her ass burned as it was pressed into the floor, her wounded pussy lips protesting every time his dick filled her and his weight fell against them. And yet still the feeling of heat and need built between her legs. Before she knew it, Diane was having one of the most painful orgasms of her life, her crushed and bruised pussy forced to its climax by Michael’s skillful love making.
When both of them had spent themselves and the sounds of Diane's cries had stopped echoing off the walls, Michael carefully pulled himself out of her pussy and lowered his head to kiss it. Whimpering at even this slight touch to her overextended and sensitive nether regions, she was shocked that he'd even managed to give her an orgasm. But she felt happy as he untied her wrists and gently stroked her hair smiling at her with a kind of pride. That look filled her up with happiness despite the sore throbbing of her body; she'd been a good girl. Sighing in contentment, she winced as she tried to move her legs together, and he picked her up gently once more, one of her arms crept up to wrap around his neck.
Upstairs Michael spread soothing ointment over the red stripes caused by the cropping, soothing away the hurt in her breasts and ass. They took a long bath together, where he gently soaped her body, careful of her bruised pussy, and washed her hair. His hands were so wonderful on her skin, despite the fact that she’d just been punished she felt like a wonderfully cherished object, cared for and pampered. Diane took a nap before dinner, completely exhausted, even though she'd slept more that day than any other.
Michael had ordered Chinese food and as they ate they watched a movie, which was punctuated by Michael occasionally toying with her breasts. Although she was sore all over, Diane couldn't help feeling stirrings of arousal at the gentle touches. On her volition halfway through the movie she moved down and gave Michael a blowjob, for the first time managing to fit his entire dick into her mouth and down her throat on her own. She reveled in the feeling of triumph as she swallowed him whole, over and over. His fingers were spread through her hair but totally for his pleasure rather than using them to help her down on his dick. The rest of the movie after the blowjob was over she spent between his legs, her head resting on his leg, while his hands ran through her hair, playing with the brown curls.
That night Michael worked her over with his tongue, gently. Sucking on her nipples, flicking them with his tongue, and gently nibbling - just enough to make her body arch in slight pain, but the pain was as pleasurable as the rest of it. Then his mouth moved down to her pussy… he touched no part of her unless it was with his tongue, gently laving away the aches in her body. Despite the slight discomfort on her part she couldn't help but respond with pleasure. His tongue was blissfully considerate, soothing as she quivered and sighed.
Wet juices ran down her slit and crack and Michael sucked one of his fingers into his mouth before running it around the rim of her asshole. She lifted her hips slightly, enjoying the feel of his finger against her sensitive nerves, his tongue sliding wetly up and down her slit, careful of her bruised lips. Then his finger pushed in, filling her ass. It was sore, but not nearly as sore as her pussy, and it felt wonderful to have him inside of her. The care that he gave her abused body was a turn on in and of itself.
As his finger pumped back and forth inside her tightest hole, his tongue carefully stroking her tenderized folds, Diane lifted her hips and gave passionate voice to a gentle and fulfilling orgasm. Soft waves of pleasure spread through her, like ripples through a pond, leaving her satisfied in body and heart.
He kissed her afterwards, ignoring h
er distasteful expression at the taste of her pussy on his lips. It was salty sweet, but not something that she cared to taste, but she did want to kiss Michael back. They fell asleep, her slight body curled in his arms.
Sunday was a day for decadence. He spoiled her outrageously - asking what her favorite dishes were and making them, she got a full body massage with oils, and they spent some time just splashing and playing in the Jacuzzi. Yet there wasn't a single moment that she felt like he wasn't in control, despite the fact that everything was being done for her.
Around early afternoon he began her training. She learned four different positions, each one to be assumed when he gave the order, no matter what.
One was the least exposing. She just had to stand with her feet spread apart and place her hands behind her head, thrusting her breasts out.
Two meant spreading her legs wide and bending over to hold her ankles. The thought of having to do that in one of those short skirts she normally wore to work made her blush, they would definitely ride up almost to her waist in that position. It also made her wince as her sore pussy parted.
Three involved getting on her knees, putting her ankles together with her knees spread apart and leaning back onto her elbows so that her pussy was spread open and exposed while her breasts jutted out obscenely.
Four was the worst though. Humiliating, she had to get on her knees, press her face to the floor, and reach back with her hands to spread her ass and pussy with her fingers, exposing herself completely. If she was wearing a skirt, she had to lift it up, and Michael implied that pants were not normally going to be acceptable, but if she did happen to be wearing them, they would have to go. Michael didn’t make her take this position fully for now, because he could tell how sore her pussy still was from yesterday’s punishment. The position made her feel shameful, dirty and turned on all at once, she was helping in her own abasement. Exposing herself in such a manner, even just to Michael, caused her face to turn bright red in embarrassment. She'd never had to open herself so completely to anyone.
It was worth it because it obviously turned him on. As he drove her home he pushed her head into his lap and she blew him until he climaxed in her parking lot. The weekend ended with the taste of Michael in her mouth.
Chapter 7
Monday at work Diane was doing her best to be productive, and it seemed as though Michael wasn't going to be distracting her too much. He’d had her come into his office so that he could insert her butt plug, but other than that he was staying hands off and she was grateful. Her body was still sore. Most of her distractions came from Juan who kept smirking at her... it was hard to keep her mind on work with him in the office, her face was bright red from remembering Friday when she had sucked Michael’s dick in front of him. It was pretty obvious he remembered too.
"I think that Juan's completed just a little bit more work than you," smiling at her, "I think that deserves a reward for such effort, don't you Diane?" Numbly, she nodded her compliance. She had no way of knowing whether or not Juan had really completed more work than her, but she wasn't going to argue with Michael's assessment either. His voice became hard and demanding, "Position Two Diane."
Red faced, she bent over and grabbed her ankles, ass high in the air. The men both moved around behind her to see the delightful view of her exposed ass cheeks. Someone's hands, she didn't know whose, ran over her ass and then pulled her panties down, just enough to expose the end of the plug in her ass and her wet pussy. Both of the men made admiring comments about her creamy ass, the pink stripes that displayed her ivory skin to advantage in between, and the wetness of her pussy. Their comments made her feel even more embarrassed, she could feel their eyes looking her over, especially Juan’s. What was worse, it was turning her on, despite the fact that her pussy was still sore it was getting wet. Which they both noticed, of course.
She stayed in position, head hanging down, as the men said their goodbyes to each other. After Juan had left, Michael came back over to her.
"Good girl," his hand stroked her hair as it covered her burning face. Leaning into the strokes Michael was giving her, she sighed and relaxed. He put one finger under her chin and brought her back up to standing. "You'll come home with me again tonight." She nodded.
The night didn’t go quite as she had expected. Instead of anything sexual they just talked and laughed and enjoyed each other’s company – although they did eat dinner completely naked. Diane realized that she was falling in love with this man, not just his cock and his sexual deviance which completely fulfilled her, but she loved finding out the things they had in common, the flashes of playfulness that she was occasionally privileged to see.
******
On Tuesday Diane came into work and went immediately into Michael’s office to have her butt plug put in. Instead he undressed her, his hands caressing her breasts and ass which were completely healed, but she couldn’t hide her wince when he stroked her pussy. The tender lips were still bruised from her time on the wooden horse.
“It’s okay,” he murmured, kissing her gently, continuing to tenderly stroke between her folds with one finger. Diane trusted him, and she relaxed into his soft manipulation of her sex, her pussy getting wet as he slid his finger back and forth, his strong arm wrapped around her.
“Bend over the table,” he told her as he released her. Now eager, and also a little afraid because she knew she was still sore, Diane went and bent over the table next to his desk, placing her hips on the padding that he’d put on it to keep her hips from the edge of the wood.
When she felt his finger push into her ass, slick with lube, she moaned and thrust back. He always did this before putting in the plug, and it never failed to turn her on now. This time instead of removing his finger he continued to push it in and out of her ass, making her wiggle and bite her lip with pleasure to have him inside of her and moving again. Her tight hole clenched down over his finger, cheeks bouncing together and apart as her inner muscles moved.
A hand crashed down on her, hard but not brutal, and she jumped and moaned again. Soft caresses soothed the pain before he slapped the other side, his finger still pumping inside of her as he began to spank her cheeks. This spanking was obviously for pleasure, not punishment, as he warmed the ivory cheeks of her ass. Humping her hips up and down on the desk, she brought her ass up to meet his slaps and the push of his finger, her body starting to get hot with need.
Then the spanking stopped and a second finger pushed into her ass. Diane practically purred, her butt moving from side to side and squeezing down as he fingered her ass. Her pussy was leaking copious amounts of fluid below his poking fingers. She gripped the sides of the desk when his fingers pulled out, her ass waving in the air like a red flag in front of a bull.
When she felt the thick head of his cock pressing against her tight ring she arched her back and panted with anticipation. The sharp pain of his penetration gave way to the sore, slick slide of his cock into her ass. This time he was much less gentle than when he deflowered her, as though he’d missed being in her body even though it had only been one day since he’d cum inside of her. The thrusts were quicker, rougher, more passionate as his hands gripped her hips, pulling her back against him.
Impassioned cries of ravishment came from Diane’s throat as her ass was split open, the sensation of Michael’s thick meat traveling into her bowels so much sharper when it was in the office at work. Her fingers dug into the wood of the table as she strained, her ass adjusting to the rude intrusion. She gloried in the sensations, the discomfort and the sharp jabs deep within her. Pushing back, her ass spasmed around him, and they both groaned together, the tightening of her hole intensifying the pleasure for both of them.
“Talk to me,” he ordered hoarsely, pulling her hips back hard against him, her ass slapping against his body as he split her cheeks. “Tell me how much you like it.”
“Oh Michael… oh Sir,” she cried out. Normally she wasn’t much of a talker during sex, but his order freed her. I
t didn’t matter if what she said sounded stupid, he’d told her to tell him. “Your cock is so thick… so hard in my ass. It hurts, it burns so good… I can feel you so deep in me. I love that you’re in my ass, that you’re the only man I’ve had in my ass. You own it, you own my ass Sir.”
“FUCK Diane,” he groaned her name, his fingers digging into her hips as his dick swelled up inside of her. Diane writhed and screamed as his steel hard rod drilled into her so hard that she could feel it in her pussy. Hot fire flamed through her lower regions, her ass convulsing, her empty pussy tightening as heat spread through it. It felt like she was orgasming, the fulfilling pleasure rippling through her even though he wasn’t touching her pussy. The sensation was so confusing, so wonderful, that Diane was completely overwhelmed. She arched and bucked in front of Michael, the surprising rapture shivering through her as his juices spilled into her backside, flooding her ass with his cum.
She collapsed on trembling legs before him, her weight resting fully on the table as he caressed her back, his cock slowly softening inside of her.
Chuckling Michael observed, “Well that was rather unexpected.”
“What was that?” moaned Diane, her body shivering as his fingers ran over her back and the tops of her ass cheeks.
