Hannah's Dilemma Ch. 02

Hannah shook her head "no," but she wasn't really thinking.

Jimmy held his cock at its base and gently slapped her face with it.

I like a girl with a little fight in her, he thought to himself.

"Does Hannah not suck dick two days in a row?" he asked, taunting the young woman.

"It's your job, now, baby. You're a whore."

Hannah felt her neck blush with humiliation. Wearing only panties and high heels, on her knees, was shameful enough. Her mind raced but she didn't know what to do.

His man-meat slapped her cheek again.

"You can't play 'hard-to-get' when you're a whore, baby."

Sensing her reluctance, he went a step further.

"You've gone this far to not get arrested for prostitution. You might as well make it all the way."

Hannah wanted to scream, but she knew he was right.

She tried to force herself to yell at him that she wouldn't give in, but she couldn't.

She wanted to say "no," but her mouth opened anyway. She had to do whatever she could to get out of this mess.

Her mind was reeling but she instinctively dipped her head to reach the tip of the semi-hard penis head that dangled down below her chin. It had to be 9 or 10 inches long and was as thick as her wrist. The rubbery head mushroomed disgustingly wider even than his thick shaft. She sought the end with her open mouth.

When she closed her lips around it she was surprised at how warm it felt in her mouth.

Again, without thinking, she began to bob slightly on his cock.

"Now, that's a good girl," he said. "Make daddy happy."

His manhood began to stiffen quickly. The size of the cock began to grow as it became more and more blood-engorged.

Hannah wondered how large it could get. She moved a hand to the front of his thigh just to get some balance. She felt the Sheriff sway.

"Fuck. Hang on," he said.

Hannah pulled her mouth off of his cock and waited on her knees, looking up at him.

The man took a couple of short steps back until he was against the bed. He leaned back on it. All the clothing that he had on were his pants, which had fallen to his calves and his boots.

"Crawl over here and take my boots and pants off," he huffily told Hannah.

It was only a couple of feet away. Hannah bent down and crawled over on her hands and knees, her large tits swaying erotically beneath her as she did.

She reached him and put a hand on his thigh. She first reached for one black boot and pulled it off. Without waiting, she pulled his sock off, too. Then she did the other boot and sock. His pants fell off his legs.

He was now completely nude. He sat with his legs spread, his massive cock bobbing freely in the air.

"Get out of those silly panties," he ordered her.

Hannah stood up slowly in front of him. He towered over her even leaning on the bed.

She slipped the silk panties off of her hips and let the thong fall to her knees. She did nothing, but felt them eventually fall around her ankles. She gingerly stepped out of them.

He whistled low.

"Fuuuuck!" he said. "What a body! And a shaved pussy - I'm gonna have to eat that out some time."

He reached between her thighs and let his finger lay along her tight slit. Her skin was very soft.

The blonde shivered noticeably and arched her back involuntarily.

An odd sensation went through Hannah's body as he said his words and touched her secret place. She felt her pussy become a bit moist. Am I really that much of a slut? But there was no denying that his touch and admiration had aroused her. Without entering her vagina, his finger lay the length of her tight slit. He made sure to gently touch the top of her slit to apply light pressure to the hood covering her tender clitoris. The Sheriff felt a tiny shudder come over the blonde's body.

When their eyes met, she averted hers. Her slightly parted lips betrayed her rising lust.

Almost to escape his grasp, the young blonde woman nervously knelt before him again and reached for his penis. It was almost rock hard now but not quite. His hands went back to her breasts, lightly stroking her pink nipples. They stood out like little bullets.

He was hideous but his touching of her tits had worked and she was becoming aroused, despite the revulsion she felt towards him.

His large hands returned to her breasts and erect nipples. His touch was electric. It shot wave after wave of sexual current through her firm melons directly to her pussy and brain. Her body felt like jelly. She dropped her head but then raised it.

"How did a slim girl like you get such big titties?" he asked. "Does your momma have big tits?"

Hannah's hand was on his but hadn't moved. Her thoughts went to her mother who would be mortified by her behavior! This wasn't the way she was brought up to be!

"Answer me," he said with a subtle pinch of her distended nipple. "Does your momma have big titties?"

"Ow!" Hannah squealed although it really wasn't painful. "Y... yes, daddy, she does."

"Guess I'd like to fuck your momma, too," he said with a chuckle. "Now put my dick in your mouth. I want to play with these damned milkers of yours."

She opened her lips and took his penis head into her mouth. Trying not to think about what she was doing, Hannah nonetheless swirled her tongue along the ridge of his cock head and bobbed her head a few times onto his stiff manhood, careful not to go too far down his rod.

Her ears burned when he spoke.

"Gawd damn, you can suck some cock, baby! Bet your momma can, too!" He gently tugged and massaged the nipples on the young woman, sensing that her pussy would begin to be awash with lusty juices. The rubbery nipples seemed to love the attention that he was giving them - the blonde certainly didn't move them away from his touch.

Hannah opened her lips wide and went further down on the man's cock. Her mind was swirling and her body was beginning to catch fire with lust.

*****

Nikki was fascinated with what she was witnessing go on in her bedroom. She knew that the Sheriff was an experienced cocksman, but he was bringing the new whore-in-training along as she had never seen him do before.

Hannah's face betrayed the struggle that she was being put through. Despite not wanting to be there, the lust was beginning to show through her actions. Jimmy was really torturing her by focusing on humiliating her while he was bringing her to a sexual peak.

Nikki heard her back door open and looked up to see one of the young women who worked for her walking into the house. She was a lovely brunette with long legs and a fine ass. She wore short shorts and a tee shirt and carried a backpack.

"Hi, Nikki!" she said.

"Hi, Ali," Nikki replied. Ali was a college student like Hannah when she came to work for Nikki three years before. The money was so good that she had dropped out of college to work full time as a whore. She and Nikki were close friends and Ali was in charge when Nikki was away. Nikki trusted her implicitly and Ali was the only other person who was aware of the camera system in the house.

Ali looked at Nikki and knew something was up.

"What are you watching?"

Nikki didn't respond. She wasn't being rude, but she didn't even hear the question. Her attention was riveted to the screen.

Ali walked around to see what she was watching. She saw the Sheriff and the young, blonde woman.

"Jimmy's gross," she said matter-of-factly. She had "serviced" him a number of times, but she preferred to leave the new girls to handle the Sheriff. He was overweight and overbearing, in her mind, and well-overly endowed.

"Oh, is this the girl that Leroy fucked last night?"

"Uh-huh," Nikki answered.

"Jimmy loves it when he has to close the deal, doesn't he?" Ali said with some disdain.

"It'd be a lot easier on these college girls if they just agreed at the beginning..."

Ali's voice trailed off as she watched the Sheriff and Hannah.

"I know I'm sick, but I'm gonna go listen down the hall," Ali said.

Nikki smiled. Ali was a voyeur of epic proportions.

Ali tip-toed down the hall and stopped at the closed door to the bedroom.

Standing next to the door, she could hear what was going on in the bedroom.

She was shocked by the sounds she heard. The first sound seemed to be of the two people kissing. Loud smacking of lips and gasps made her recall how grossly the Sheriff kissed. She could make out the sounds of movement on the bed and she thought she heard a bit of a struggle being put up by the beautiful blonde.

"You're way too big for me," Ali heard Hannah say in a girlish voice. "You'll tear me in two," she moaned. "Please don't stick that in me, daddy!"

There were more sounds of movement on the bed, of rustling sheets and groans of both a man and a woman.

Then, "pleeeeease, no!"

Sounds of two people moving on the bed continued but Ali got the idea that Hannah was being pinned on the bed.

"Nooo, please, don't stick it in me! I'll do anything else, daddy!"

There were some more sounds of movement and then a grunt from Jimmy and a groan from Hannah. There was great intensity in the words and sounds.

Within seconds, Ali heard a girlish moan.

"Ughhhhhhh. Ughhhhhhhh! Ohhhhhhh!"

Ali knew that Jimmy had gotten at least partially inside the young college girl's vagina.

"Relax," she heard the Sheriff growl. "Relax, gawd damnit!"

"It hurts... you're too big, daddy" was the pitiful reply. "Oooooohhhhhhh," was the next sound from the young woman.

"Spread your legs! Relax!"

"Oooohhhhh, no, pleeeeeease!"

What was clear was that Jimmy was inside her pussy now. There began to be a steady, tawdry sound of flesh smacking together.

A high-pitched mewling sound from Hannah's lungs accompanied each smack.

"Oh! It hurts!"

"Daddy, please, no!"

"Ohh, gawd, no!"

"Oooooh"

"Oooooh, gentle, please!"

Jimmy's got her good now, Ali thought. He'll screw her until her pussy is stretched.

Hannah would have been much better off spreading her legs willingly for the man's dick. It was only a matter of time before the girl lost her innocence and knew that it was easier to let the men pleasure themselves like they wanted. She'll learn.

There was now a steady rhythm of moaning and grunting that Ali knew would only end when Jimmy exploded deep inside Hannah's grasping cunt. What neither Ali nor Hannah knew was that the Sheriff wasn't even half-way inside her pussy. He was trying to work his tool into the extremely tight twat.

Ali jumped a bit when she felt a pair of lips on her shoulder.

"Shhh!" she said when she saw Nikki standing behind her.

Nikki grinned and whispered, "you love listening to a new girl get fucked, huh?" Her hand dropped to Ali's buttock and squeezed. "You are a sicky," she said softly

Ali smiled. She knew that Nikki had been watching the Sheriff on the computer.

"Want me to ride you with a strap-on?" Nikki asked playfully.

"Shhhh!" Ali said very quietly, but she smiled at the older woman.

The noise was becoming more intense in the room. Hannah was become increasingly vocal.

"Oh! That hurts, that hurts, that hurts!" she cried rapidly. "Please be slow, Daddy! You're too big for me!"

The Sheriff grunted, but there were no words coming from the man.

Ali could tell that Jimmy was very likely working his massive tool into the young woman pretty slowly so that he really wouldn't hurt her physically. But he was definitely stretching the college girl's pussy like it had never been stretched before. The feminine mewling made that clear.

Ali hung by the door listening intently to what was taking place in the room.

*****

Inside the room, the temperature was high.

Hannah was naked on her back, her legs spread wide, with the Sheriff, equally naked, fucking her. The college girl's thighs were lying flat-out open on the mattress, spread at a 90-degree angle from her body.

Her face - visible above the Sheriff's shoulder and back - betrayed the discomfort, shock and disgust that she felt submitting to the man. She was doing something so filthy, so perverted, and so uncomfortable, that she could not have dreamed of this just a week ago.

"Oooohhh! Ooooohhhh, please..." were words escaping from her lips without her even thinking.

Her mind was boggled but the Sheriff was working his massive, curved cock deeper and deeper into her resisting vagina.

"Relax," he urged, his breath hot on her ear. "Relax your pussy."

"I...I can't," she said girlishly, "you're too big for me!"

But each cock stroke seemed to flower open her pussy just a little more.

He shifted from short strokes to longer ones that opened her passage wider and deeper.

Hannah's mind went red for a moment and her big blue eyes rolled up and her mouth hung loosely open. Her beautiful body was taking a pounding from the man.

When she regained her bearings, she realized that the man was no longer pounding her. There was no movement at all! A feeling of being unbearably stuffed came over her, but it was not painful. She could feel his thick pubic patch of hair against her smooth vagina and the end of his stiff, massive meat seemed to pushed her cervix way back into her body.

Oh ... my ... god! He's all the way inside me!

"You're snug," he said to her. "I told you if you'd relax, I'd get it in you all the way."

He lay still completely inside her.

"You alright?" he asked with a slight laugh.

Hannah had her arms wrapped around him now, not realizing how they got there.

"Uh, huh," she said softly, humiliated at her answer. She didn't know what to say -- completely spread-eagle and nude beneath the man.

The thick base of his erect manhood stretched her vaginal lips to their fullest and Hannah could feel his overgrown testicles lying heavily against the crack of her soft buttocks. His prick felt like it was touching her lungs, making it hard for her to breathe!

The man's head dipped down and he drew her fresh tit to his lips. Taking the pink bud into his mouth, he sucked vigorously. His tongue swirled at the nipple.

Hannah felt it crinkle into a rubbery head and begin to shoot sexual current through her gorgeous body. Her head fell back on the mattress. She felt a loss of control. The man was slowly drawing his long cock out of her pussy and then driving it back inside her. He was so large that she could feel every vein, every ridge, every contour of his massive curved cock. All while he sucked her breasts!

A strange thought flew through her mind: Thank god he's not going hard and fast on me. The inexperienced college girl didn't think she could handle that.

Hannah shifted her legs slightly and felt her vaginal juices begin to lubricate the man's penis. She could feel her cunt beginning to lube up well. Oiling his cock with her cuntal juices made the fucking much easier on her tight pussy. Her heels lodged at the top of the backs of his thighs, just at his ass cheeks.

The man shifted his attention from one of Hannah's firm tit to the other, each time sucking hard on her nipple, while keeping the other nipple at attention with his fingers. Squirm as she might, she could not escape the intense sexual electricity shooting through her body.

Hannah knew that he wanted to conquer her.

Don't give in! Don't give in! Don't give in!

Hannah silently begged her body to not betray her even as she felt herself slipping into the sexual responsiveness that she despised! The feeling of his rock-hard erection working her vagina was something that she had never felt before. He was reaching depths that simply had not been touched. Sexually and psychologically, it was difficult for her not to react with passion.

Her hands gripped the bedspread. Through glazed eyes, she watched the Sheriff sucking on her breasts. It was so surreal to the young woman to watch this domineering old man feasting on her supple flesh but the sensations rocking her body told her it was real!

He's an animal, she thought.

He looked her in the eyes as he sucked her lush tits.

Hannah's head fell back on the bed in utter shame. Her body was betraying her. How could it not?

Her lower body ground back at his invading tool. Her heels pulled her tight ass up to meet his cock plunge.

Without thinking, she said, "Oh, god!" The words surprised her. It didn't even sound like her voice!

Her hips rotated up to meet the driving cock. After one thrust up, she tried to stop moving but found her buttocks pushing her pussy up towards the man's cock.

Slowing accepting that she felt better if she allowed herself to begin a little rhythm to the fucking, she began to work her pussy up towards the man's body, almost imperceptibly, at first. But finding it pleasurable, she softly moved her hips upward.

"Now you're working that pussy, baby," the Sheriff said. "Work it on my shaft."

The two bodies were connected by his enormously long prick, but the sexual sensations were heightened by more than just that. His touch of her breasts and the feeling of a man lying on the soft skin of her inner thighs between her spread legs sent her into ecstasy. She could feel the small pin-pricks of sensation racing through her hardened nipples.

"Fuck my cock. Squeeze it with that little cunt of yours, honey."

Hannah tried to ignore his demeaning words and enjoy the pleasure that her slight movements afforded her. She was starting to breathe hard. Her mouth opened to gasp for a breath so needed by her lungs.

Jimmy locked his mouth wetly on hers. His thick tongue invaded her open mouth, searching and flicking for her tongue. He found it and lavished his against hers.

Her will to resist was being utterly destroyed by the unwanted desire building deep in her innocent body. The young beauty knew that she should resist -- she had a right to do anything she wanted to resist -- but she began to give in to the strange sensations of fear and desire.

She squirmed back a little, whimpering helplessly at the feeling of her legs being spread so wide and taking such a large cock into her body, but the man's steady cock-thrusting was making warm contact with the quivering bud of her hotly aroused clitoris. Her entire vaginal area was soaked with a strange desire that permeated her entire being. She pulled her mouth away from the Sheriff's just long enough to suck in a breath tightly to try to hold back a lewd groan of pleasure that was building in her lungs.

It was no use!

When his lips joined hers again and his tongue entered her mouth, he found a willing partner in hers. Their tongues eagerly swirled around the other!

The grinding of their hips and the perverted sluicing sounds made by their bodies made her give way to the inexorable tide of passion rising through her body.

"Oooooooooohhhhhhhhh!" she groaned.

Jimmy's right hand went between their bodies and found her throbbing clitoris. He rubbed it gently with his fingertip. With each thrust and withdrawal of his penis, the blonde's lust became more unbearable. Her nubile body could no longer resist! She spread her passion-drenched thighs wide for his pleasure.

"Aaaaahhhh! Aaaaahhhhhh! Aaaaaaaaahhhhhhhhh!" she cried out. "Ohhhhhhh, gawwwd! Ohhhhhhhhhh!"

*****

Nikki closely watched the intense initiation of Hannah on her laptop screen. She was glad that she was recording it. The overhead video angle from the hidden camera in the ceiling was particularly powerful.

For some inexplicable reason, she enjoyed watching Jimmy seduce a young, virginal type like Hannah who usually put up a good fight before succumbing. The innocent blonde had put up a struggle but Nikki knew she'd eventually give in. It was work for Jimmy, but it was worth it. He loved breaking college girls in.

Nikki saw that Hannah was a haughty and proud student who felt much above a common whore. Yet here she was being trained to be ridden like a young horse who had never had anyone in the saddle. Jimmy was the perfect trainer. By the time he finished with her, she'd allow herself to be ridden by any man. There wouldn't be many men who would match the often-overzealous sexual demands of the Sheriff.