Mary Jenkins - Innocent in Chicago Volume One

"Ooooooooh," she moaned at the lewd tickling sensation coursing through her. And expecting that he would now take her, she moved back on the chair, thrusting her hips to present them more fully, and rotated them slowly and teasingly under his hands around the shallow impalement of his tongue probing at her anus. He drew back, but instead of the pressure of his penis into her, she grunted at a further series of painful slaps, then his kisses again and the hard blows, all in quick succession. She crouched, cowering on the arms of the chair now, crying with agony and pleasure, gasping and choking on the salty flow of tears that dripped from her eyes down onto the seat. Her whole body was tense and trembling, her gaze directed hack between her legs to watch him.

"Cynthia, darling," she heard him croon gently. "I've always wanted to fuck you in the ass. Now, I'm going to do it."

"Oh no, Conrad, please," she whimpered, a sudden feeling of complete helplessness coming over her. "It'll hurt."

"No, it won't, my darling," he crooned on softly an almost reverent tone to his voice. "I'll do it gently."

And through the wet veil of tears covering her eyes she saw his thighs move forward slightly until the huge, throbbing head of his cock was pressed tightly between the cheeks of her ass. She automatically tightened her buttocks in a hopeless attempt to keep him from entering her there but his thumbs on either side of her anus pressed harshly outward and opened the whole of her back passage to the mercy of his unnatural desires. He pressed the slippery lubricated head of his cock tightly against the tiny, puckered entrance and pressed forward gently at first.

"Aaaaaangggggghhhhhh," she screamed as she suddenly felt the tight unyielding muscles of her anus being forced slowly outward from the strength of his relentless pressure. Her face contorted tightly in pain and she groaned like a wounded banshee down into the cushion of the chair, her scream muffled and desperate as though she were being impaled on the end of a giant spear shaft.

There was a slight pop as the tight outer ring of her anus suddenly gave way and the head of his throbbing member slipped inside. She groaned again and then the momentary pain of his initial entry passed and her rectum relaxed and opened to receive him. He grunted behind her as the tight unused flesh clamped around his cock like a vice but did not ease off on the pressure he was exerting against her. He jerked forward with short hard strokes, digging deeper and deeper into her belly until Cynthia's whole behind felt stretched and distended beyond all hope of ever recovering. She felt as though her whole insides were being pushed up hard into her throat and there was no way in the world she could escape the cruel and unrelenting instrument skewering its way deep into her bowels. His hands curved around under her trembling belly and she could feel his fingers pulling the hot, wet lips of her cunt open beneath her. He thrust forward with his fingers, sinking three of them deep up inside her. She moaned again, her loins feeling completely filled with the hard, thick cock tunneling into her rectum from behind and his probing fingers sunk deep in her vagina.

There was a sudden gasp from his lips and she felt his pelvis smack hard into the flaccid cheeks of her buttocks pushing them up and out. She whimpered and felt her whole body jerk and writhe for a moment in protest and then relax in helpless acceptance as the whole of his pulsating cock lay buried deep in the confines of her widely stretched rectum. He stood still for a moment to give her time to adjust to the unnatural invasion of her back passage and then began a series of slow short strokes in and out of her, his fingers probing deep in her cunt and keeping time to his cock gliding smoothly in and out of her rectum. And then to her surprise the driving rod and the searching caress of his fingers thrusting into her vagina soon aroused her in a strange masochistic way and she began eagerly rocking her hips in the air behind her, propelled by the suddenly mounting urgency of her own passion. She could feel the old familiar fire building again deep inside her belly and she rocked and rotated wildly beneath him, the round white magnificence of her buttocks hollowing and clenching around the hardness of his cock with each hard, brutal stroke he rammed into her. She could hear him clucking behind her in lewd delight, as he watched his thick rod of flesh disappearing deep down inside the smooth hairless mouth of her rectum and then gasping crazily to himself as he jerked out again and the tight pink flesh flowed with it with a wet sucking noise, clasping to it as though it did not want to let go. His naked lust incited her more and she began to move with earnest now, the licking flames of her own desire almost ready to erupt. She could feel he was close to cumming. She could feel him growing inside her and stretching the already stretched walls of her pulsating rectum wider and wider until she thought she could not stand the strange, obscene pain and pleasure another moment longer. Her eyes were dilated and bulged wide as she humped beneath him. The tightness of her asshole clasping and unclasping around him like a sucking fish as he fucked into her now with all his lustful strength. And then he came!

Just as the rising tide of her own passion spilled out deep inside her, she could feel the hot warm spurts of his sperm emptying deep, deep inside her rectum until it felt as though he were filling her whole body with the hot sticky fluid. Her full, rounded breasts dancing beneath her kneeling form hardened, as though he had broken through her belly and was dumping his cum into them. She could taste it on the end of her tongue swirled her tongue lasciviously around inside her mouth, savoring with delight the delicious and pungent taste. She heard him cry out behind her, and his thick pulsating member spurted one last thick jet of his sperm deep in her rectum and, with a wild cry, her whole body contracted in the final burst of her own orgasm.

Her eyes closed, she collapsed into the chair as he withdrew with a wet sucking noise, as though he were pulling a body from quicksand. A thin string of sperm followed the tip of his cock, still connecting it to the stretched hole of her rectum, a lewd reminder of the obscene coupling they had just gone though. Cynthia lay in a limp heap in the chair unable to move. Conrad reached down with his arms and picked her up and carried her into the bedroom where he laid her silently on the bed. The sheets were cool on her still tender buttocks. He quietly unzipped the tight girdle and slipped it off. The mattress sank as he lay down beside her and she turned to him, her mouth half open, her lips wet, and waited for his kiss.

When she awoke the next morning, Conrad had already left. Under the clock on the bedside table was the amount of money he gave her each time she came plus an extra hundred dollar bill. She got up, showered, dressed and tucked the money in her wallet. Smiling to herself, she put the hundred dollar bill in a separate compartment. For several weeks now Conrad had been tipping her extra, as though to say, "If you move into an apartment by yourself, you'll have all this and a lot more."

She debated whether or not to tell Mike, but had decided against it, keeping the extra money for herself. Although she knew he would be furious if he found out, lately he had not been very generous in giving her spending money and she was beginning to resent the fact that everything she earned disappeared into his pocket. Usually she had purchased clothes with the extra cash. Mike had questioned her about them, but he had seemed to be satisfied with her explanation that Conrad had bought them – at least up until now.

Continued in volume two.