Jenna's Pickle Ch. 03

Please read Jenna's Pickle and Jenna's Pickle (Ch. 2) first.

*

Jenna stood bent at the waist. Her neck was clamped through a pillory and her wrists were tied together behind her back. Her legs were spread wide apart and her firm breasts dangled freely. She wore white bobby socks and 4" Mary Jane heels, which forced her to stand on her toes and forced her ass to be held higher than her shoulders, providing a beautiful display. Her eyes were blindfolded, but her soft, wet lips were not gagged. Her pussy was wet and quivering and her clitoris was swollen and aching to be touched.

Behind her she heard the door being opened and heard Jimmy talking to someone. Jenna tried in vain to turn her head and see who was coming in and seeing her in this humiliating, helpless position.

"Come on in," Jimmy said. "Here she is; this is Mrs. Carter. A real beauty, isn't she?"

Jenna blushed. She hated whenever Jimmy and Rob told their 'guests' her real name. It would not be difficult for one of them to realize that she was the wife of Joseph Carter, a local politician. And, then it would only be a matter of time before Joseph discovered that she had been cheating on him and that she had become Jimmy's and Rob's sex slave in an attempt to keep her affairs secret.

"Say 'hello' to our guest, Mrs. Carter," Jimmy instructed.

Jenna voice died in her throat and the only sound she made was a small moan of frustration. She shifted her weight from one leg to the other and back again, which made her ass wiggle; and she writhed her bound wrists, which made her firm breasts sway slightly. She heard the two men chuckle at her humiliation.

"I'll leave you two to have some time alone," said Jimmy as he closed the door behind himself.

Jenna began to panic slightly and twist against her bindings. She was alone, bound and naked, with a stranger. What would he do to her? Would he hurt her?

She heard him move up behind her and felt him run a finger lightly down her spine to the crack of her ass. Her breath quickened and she stiffened when his finger circled and pressed against her puckered anus. She tried to pull away, but that was impossible. He chuckled at her and slapped her ass, not hard, but enough to make a loud smack that rang in her ears and made her burn with humiliation.

"Now, now, is that any way to behave?" he asked, mocking her. "You must be a good girl for Daddy."

The stranger's finger continued its journey between her crack to her pussy. The finger slipped inside her tight, wet tunnel and stroked her. Jenna arched her back, trying to get the finger to go deeper inside her, but the finger slid out with a wet slurp, and continued down to her clitoris. The stranger smiled as he felt her hard, swollen clit. He held his finger against it, but did not stroke it. Jenna was on fire; she was so desperate to be stroked that she began pumping her hips against the stranger's strong, thick finger. He chuckled at her again and she stilled her hips, burning with shame. However, it was not long before she again began pumping her hips disgracefully against him.

"My, my," laughed the stranger as he watched Jenna's hips thrusting against his finger. "Did Daddy's little girl get all excited and wet her panties?"

A blush spread over Jenna's entire body, but she was so desperate for release that she only pumped her hips faster against the finger and moaned. She frantically hoped that he would not stop, that he would allow her to orgasm, but he pulled his finger away, causing her to whimper in frustration.

"Well, my dear," he said, "Daddy is waiting for your answer."

"Y-yes," she stammered.

The stranger lightly flicked her clit and said, "Yes, what?"

Jenna's head was spinning. She knew what this pervert wanted her to say; he wanted her to call him 'Daddy,' but she didn't know if she could play along with his incestuous fantasy. She was trembling with both shame and desire when the stranger flicked her clit again and she answered, "Yes, Daddy," with a small whimper.

The stranger replaced his finger against her clit and Jenna again began pumping her hips, stroking herself against him.

"Oh, such a good girl," he crooned. "But," he continued, pulling his finger away from her pulsating clit, "Daddy thinks you've had a little too much excitement for now."

Jenna groaned with frustration and thrust her hips back, trying to regain the stranger's finger. "Please," she whimpered. "Please, Daddy, please."

"My poor little girl," the stranger said in a patronizing tone, patting her rump. He began to move to the front of the pillory, his hand gliding across her back and down to her dangling breast as he moved. He gripped the breast and rubbed his thumb over the erect nipple before he walked in front of Jenna's face. "If you are a good little girl for Daddy, then Daddy will give you a treat. Okay?"

"Yes ... Daddy," she replied.

"Good girl," the stranger cooed.

*****

Dan looked down at Jenna Carter and smiled. He had been working for her husband, Joseph Carter, for over a decade and, despite all his hard work, he was largely ignored. All the big promotions and big bonuses went to Joseph Carter's personal friends, not the workers who did the most for him. Today, however, this worker was going to get the biggest bonus of all ... fucking Joseph Carter's trophy wife.

He undid his pants and pushed them down; his cock sprang out. He was harder than he'd ever been in his life. He rubbed the head of his cock against Mrs. Carter's full lips. She obediently opened her mouth and he slid his turgid cock inside. She wrapped her lips tightly around him, sucking and licking. He let out a guttural groan; the sensation of her hot, wet mouth on his cock sent shivers up and down his spine and legs; the pleasure was so great that his knees almost buckled and he had to grab the pillory to keep himself upright. He kept sliding, slowly, deeper into her mouth, down her throat. He felt her tense slightly as she tried to control her gag reflex. He watched her bound arms twisting and knew that she wished she could push him away and stop him from penetrating her mouth so deeply. But, she was helpless. Her tender mouth was completely vulnerable to him and his cock.

"That's a good girl, take Daddy all the way in," Dan purred. Her submissiveness made his balls tighten. Mrs. Carter had always been a haughty bitch, but now she was trembling around his cock and straining to control her gap reflex. On the occasions she came to her husband's office, Dan or one of his co-workers would stop their work to provide her with whatever she wanted. Now, she was the one providing him with whatever he wanted, and struggling not to displease him.

She made tiny little whimpering sounds that vibrated down his shaft and made him moan. He could almost come without thrusting ... almost. Dan gripped her pillory-encased head, pulled his cock back, and rammed it back down her throat, hard. Again and again he rammed his cock into her warm, wet hole. Mrs. Carter gagged and made muffled moans as he fucked her face. Saliva was oozing from her lips and down her chin, which caused a wet slapping sound each time his balls smacked her chin. She struggled to breathe through her nose at each backstrokes and to not gag at each forward thrust. But she did gag and her throat convulsed deliciously around his cock.

It didn't Dan take long. The entire situation was a wet dream come true. His dick-of-a-boss's haughty bitch-of-a-wife was naked, tied up, bent over, and sucking his cock. One more thrust and he groaned and his cock shuddered, shooting his spunk between Mrs. Carter's plump, rosy lips.

"Keep sucking," he groaned as his cock continued to throb and spurt. He had heard from Rob that it was quite pleasurable to have a woman continue sucking on a man's cock even after the man had spent himself. There was something delightful about the warm, wet suction coaxing out the last bit of semen. And Mrs. Carter did not disappoint. He felt her mouth pulling the last bit of spunk from his spent cock and the sensation made his balls tingle.

*****

Jenna obediently swallowed all of the stranger's sperm and continued to suck on his cock until it was limp. She kept a firm grip on it with her tongue and lips so that as he pulled his prick out of her mouth, her tongue and lips would massage it and clean it of any residual fluids.

"Ahhh," the stranger crooned with a satisfied groan, "Daddy's little girl has definitely earned a reward." Jenna could hear him moving back behind her. This time, he placed the heel of his hand against her labia. She wiggled her hips to get it between her labia and then pressed her clitoris hard against it and began humping his hand furiously. She was terrified that he would stop before she could climax.

*****

Dan looked down at Mrs. Carter's smooth, plump ass dancing on his hand. He was becoming hard again watching her performance. He kept his hand completely still; he enjoyed watching her do all the work, struggling so hard to give herself an orgasm. Her hips thrust back and forth, her wrists twisted in their binds, her thighs and belly trembled, and she moaned and whimper softly with her efforts. Mrs. Carter had a wonderful body, in Dan's opinion. Her waist was narrow, but her breasts, ass, and thighs had soft, plump flesh on them. Her ass had an adorable dimple and the flesh jiggled ever so slightly as she masturbated.

The next time Dan fucked his boss's wife, he would ask that she be tied to a bed so he could lie on top of her and feel her curves cushioning his body as he drilled his cock into her. He fantasized about his next time as he idly watched her ride his hand. Next time she would be on a bed, her wrists tied to the headboard, her eyes blindfolded again, her glorious mane of hair spread out on the pillows, her knees bound to the bed's side rails under the mattress. Her knee binds would be loose enough that Dan could move her knees closer to the headboard or the footboard as he wished, but not so loose that she could pull her knees together. Maybe, before he fucked her, he'd run a rose softly over her body, a little hint of romance in the middle of her rape. After all, he wasn't opposed to allowing Mrs. Carter pleasure; he was being very generous right now, allowing her to pleasure herself. As he mused, Dan noticed Mrs. Carter's tiny rosebud of an anus. It looked very enticing, half hidden between her rounded ass cheeks.

*****

Jenna froze in mid-stroke as she felt the stranger's other hand caress her ass and one finger wiggle between her buttocks and prod her anus. She whimpered, squirmed, and tried to clench her ass muscles to ward off his attention. But, all she got for her trouble was a stinging slap from the hand she had been humping. She could feel a large wet smear on her ass where the stranger's hand, covered with her secretions, had smacked her.

"Don't make Daddy spank you again, sweetheart," the stranger reprimanded. Jenna hear a sound behind her, it was a lid being lifted. She knew from when Rob and Jimmy had first brought her into this room that there had been a jar of Vaseline on a nearby table. She braced herself.

*****

Mrs. Carter had more than enough lubrication that Dan could have used the copious fluids from her pussy to grease his cock and her ass, but he was impatient and didn't want to take the time to transfer her lube from one hole to another. Instead, he flipped open the jar of Vaseline and quickly slathered his cock, then smeared Mrs. Carter's ass, pushing his finger in deep to coat her inner passage. Her muscles squeezed him so tightly he groaned.

"Oh, my goodness, someone is very tight," Dan purred. "If I hadn't seen the video myself, I would have sworn that Daddy's little girl had a virgin hole hidden back here," he said, referring to the video of Jimmy and Mrs. Carter having sex in the back of Jimmy's van; it was the video Jimmy and Rob were using to blackmail her.

Dan wiggled his finger inside her and Mrs. Carter squealed and tried to pull away, making him laugh. He guided the head of his cock to the entrance of her ass and grabbed her hips. With one long, smooth stroke, he pressed inside her tight tunnel. She was so tight, Dan had to grip her hips forcefully and concentrate on his breathing in order to keep himself from climaxing again. Despite the fact that he had just, minutes before, experienced the most explosive orgasm of his life, Mrs. Carter's viselike grip on his cock made him want to explode all over again, right now.

Slowly, he counted to ten and breathed down his orgasm, but when he looked down at Mrs. Carter's puckered anus wrapped so tightly around his cock, he had to look away and count to twenty. Eventually, he got himself under control. He leaned over her and placed the heel of his hand back between her labia, pressing against her tight, swollen clitoris, and waited.

*****

Jenna shifted her hips very slightly, but the incredible pressure in her ass made her gasp; she held herself rigidly still and willed the pain to subside. She was on the torture rack, trapped between the overwhelming need to orgasm and the pain of the stranger's cock in her ass. She had only experienced anal sex on two occasions before and both times she had been pleasantly drunk, or drunk enough that the pain had been numbed. The first time was with her husband, Joseph, and she only did that because she loved him so much. Joseph loved her too, which was why he never again asked for anal sex, knowing how little Jenna had cared for it. The second time had been with Jimmy, the man who was blackmailing her into being his and his son's sex slave. On that occasion, Jenna had been so drunk she barely remembered feeling anything.

But this time she was not drunk and she felt every inch of this stranger's cock plundering and stretching her tender hole. His cock was not as long or as thick as Joseph's; she had realized that when she sucked him. So she concentrated on relaxing her anal muscles and she wiggled her hips to see if she could find a more comfortable position. She found that if she spread her legs further apart and arched her back so her hips were tilted upward, then she felt less pressure and pain. Once she maneuvered herself into the most comfortable position she could find, she again began rubbing her clit against the stranger's hand.

As she humped the stranger's hand, Jenna felt her ass clenching around the cock inside it, but her lust had taken over and couldn't be denied. The pain and pressure in her ass had become secondary to the slick friction of sliding her aching clit against the heel of the stranger's hand. Her orgasm was within reach and she couldn't stop, couldn't slow down. Her hips swiveled and bucked with short, fast movements as she roughly stroked her clit against the strong, callused hand that promised her a glorious climax; she groaned and grunted as she struggled; the tension in her belly coiled tighter and tighter until it snapped and her pussy shuddered and seized; and she ground her clit hard against the stranger's hand, desperate for him to squeeze every last pulse of pleasure from her flesh.

Once the most intense jolt of her orgasm began to ebb, Jenna felt lightheaded and her knees began to weaken. Fortunately, she did not fall because the stranger grabbed her hips in a hard, bruising grip and began fucking her ass with deep, punishing strokes. She heard his grunting, but it sounded oddly far away to her lethargic brain. She felt the pain and pressure of his cock's hard, penetrating strokes, but her muscles were so tired, they would not tense in response. This was probably a good thing; she was as relaxed as she could be without actually losing consciousness. She passively allowed the stranger to support her weight while she panted, trying to catch her breath.

*****

Dan was going wild; the feel of Mrs. Carter's orgasm from the inside drove him into a frenzy. He was pumping his cock without restraint into her, just needing to fuck her hard until his balls emptied again. He had felt her legs buckle, but she wasn't getting away that easily. He grabbed her hips and held her up as he leaned the full weight of his body into her tight ass.

"Fucking take it, you bitch," he growled. His incestuous fantasy was forgotten; all that remained was the primal urge to fuck her deep and hard. He kept pounding and pounding into her, grunting and groaning, his fingers leaving bruises. He took longer this time than the first, but eventually he felt his balls tighten and he pumped gushers of sperm deep into his boss's wife's bowels. He groaned in satisfaction as he pulled his spent cock out of her anus. He reached for a towel on the table and began wiping his cock. He was pleased to see that there was no fecal matter on his cock; Mrs. Carter had undoubtedly received an enema before his visit. But, he did see tinges of blood mixed with the Vaseline. He smiled; he truly had busted the bitch's ass.

*****

"Well, I'm off," the stranger said.

Jenna could hear the sound of him zipping up his pants. She was still feeling weak and lightheaded, but she was able to hold herself up with her own legs again. Her ass was burning and throbbing with pain. Never before had Jimmy or Rob or any of their friends hurt her as much as this stranger had. She had been humiliated and degraded countless times before, but this time she endured both emotional and physical pain. She had to find a way to get out of this situation. This was no longer simply a matter of hiding her infidelity, of saving her marriage, of protecting her and Joseph's reputations, or of preserving Joseph's professional image and career. This was becoming a matter of her safety. What if the next man Jimmy or Rob brought hurt her to the point that she needed a doctor or a hospital? She was thinking frantically about what she could do to save herself when the stranger patted her rump in farewell.

Then he said, "I have to get back to work before the boss notices how long I've been gone. It's not easy working for a man like Joseph Carter ... but then again, I'm sure you know all about that, don't you, Mrs. Carter?"

Her world went black; she didn't even hear the door behind her open or close. Her knees buckled and would have hit the floor if not for the pillory holding her up by her neck. If Jimmy had not come in immediately after his friend left, Jenna probably would have strangled to death. As it was, she might have been better off dead.