"Too bad, because now you're going to watch your girl earn some of that money to pay me back. I've already offered her an alternative, but she turned me down."
"You bastard," Duncan spat at him, "You filthy animal!"
Wiles was slowly stripping off his clothes, his erection already evident through his shorts. He was grinning lewdly, watching the horrified look on Duncan's face, and waiting to see what his reaction would be when he, Wiles, finally rammed his hardened cock in his sweet, innocent girlfriend's tight little pussy.
"You know what to do," he directed the question to his companion. "let me get in her and get her started, then cut her ankles free!"
"Noooo," Gillian moaned, "Please.. don't!"
Duncan was struggling to get free from the chair, but it was useless, he was tied too securely and there was nothing he could do, but watch the degrading spectacle being performed upon Galleon's naked body.
Wiles ran his fingers over her moist, throbbing cunt several more times until he could feel her dampness on his fingers, then he traced his fingers between her full, luscious buttocks cheeks, wetting them with her own juice. She was squirming as he touched her and he inserted a finger into her vagina, wiggling it furiously, getting her ready for his impeding impalement of her genitals.
"See how she wants, it," he taunted. "She's so ready… so wet."
Gillian had her eyes tightly closed, not wanting to look at the two men who had been torturing her, and she couldn't bear to look at Duncan.
Wiles moved on the bed in back of her, working his finger deep in her cunt, then moistening the crevice of her buttocks once again. She could feel his massive, throbbing organ jerk against her behind pushing into the soft flesh of her buttocks and she tried to pull away, but his hands gripped around her waist and pulled her back towards him. His hands fondled her behind, taking great handfuls of her soft, ample flesh between his fingers and squeezing. His fingers prodded at her back opening, pulling her cheeks firmly, cruelly apart until he could see the tiny puckered hole of her anus. His finger prodded at the fleshy virginal ring and probed teasingly around the tight elastic opening.
"Aaaaggghhhh," she screamed, her eyes opening in terror, suddenly realizing what they were going to do!
"No.. Gil, no!" Duncan screamed, "You can't do that!"
The two men just laughed and gloated while Wiles eased his hips up against her widely parted buttocks.
"This isn't going to be easy," he growled, "She's so fucking tight! But I'll screw her!"
He held her buttocks apart, separating them until they were squashed out like two balloons. He guided his prick at her opening until the thick, red head of his monstrous, pulsing cock was pushing against the small brown ringed hole. His hand gripped her thighs and waist and pulled her back onto him, tearing at her tight, tender flesh as he jammed his staff into her until it stuck.
"Aaaaauuuggghhh," she screamed again, feeling her skin give way to accommodate his giant organ. She felt like she would faint from the pain and she buried her head in the bedspread and closed her eyes!
"Hold her head up," Wiles shouted to the other man, "I want her to see Duncan while I fuck her. I want him to see her suffer so he'll know what to expect if he doesn't come through."
Tears were streaming down Galleon's face and she could hardly catch her breath because of the agonizing pain. He pulled at her buttocks again, shoving further and further into her constricting channel. Her tight wall of flesh gave way and he could feel its tightness clamp painfully around his throbbing prick and he stopped momentarily so that he could adjust himself to the pressure, then jammed into her again. He could see his erect cock disappear between her firm buttock cheeks, like a knife into a pillow. Her face was contorted in agony and pain, humiliation and shame. She wanted to die, she couldn't stand it any longer.
When he was almost fully imbedded in her anus, he ordered the other man to cut her legs loose. He freed her with a slash of a knife and Wile's hands gripped her pelvis and pulled her fully back onto him. His penis ached from the tightness, but it felt good. He had never felt anything so tight in his life and that, along with the knowledge that she was suffering, nearly brought him to an early climax. Her arms were still tied and she tried to roll her body away from him, but he was too strong for her weak, futile efforts.
Her lips bled and she bit into them trying to keep from screaming. She knew that Duncan was suffering along with her and she had already caused him enough pain.
Wiles sawed impassively into her, his lips curled in an evil grin as he enjoyed the tightness of her passage. A glaring hatred burned in his eyes as he impaled the helpless girl while her equally helpless lover watched horror stricken from the edge of the bed.
"Sooo good!" he crooned, looking at Duncan. "She's got such a nice, little hairless ass. You should have tried it!"
Duncan was red with anger and frustration, knowing that this man was painfully ripping into his girl, torturing her, shaming her. He wasn't sure that all the love in the world would or could ever erase this experience from her mind.
She sobbed uncontrollably as her body was rifled, her back passage cruelly deflowered, relentlessly penetrated.
The other man stood almost passively while Wiles drubbed harder and harder into her, but his hands were clutching feverishly at his trousers, feeling his nubby penis begin to grow erect. He liked to see women suffer when they were fucked, it excited him as no normal lovemaking could.
Gillian tried to arrange her body so that the pressure would be lessened. but his rod was monstrous and no matter how she squirmed, it just got worse.
"STOP.. STOP. PLEASE!!" she gasped as his fingers reached down in front of her and pulled the lips of her vagina apart with his fingers while she was impaled on his throbbing phallus. He could feel the dampness between her legs and he played and pulled at her vagina and rubbed his thumb furiously over her clitoris until she was half screaming, half moaning in the humiliating knowledge that her body was suddenly beginning to react to his horrible, teasing manipulations of her helpless sexual genitals.
His fingers were skilled and he knew that she couldn't resist her climax if he didn't stop his fingering, no matter how much the other passage ached. He wanted Duncan to watch her cum with another man buried in her, fucking her from behind, fucking her like no one had before. He grinned and increased the rhythm of his fingers, prodding slowly, tantalizingly into her wet vagina. He could feel the heat and weight of his own prick with his fingers and his brow was covered with perspiration in an effort to stay his own climax until she had cum, until he had made her suffer that final humiliation, until he had made her cum!
"Ooooohhhhh," she gasped involuntarily feeling her vaginal walls begin to lubricate heavily from his playing. Her clitoris was hard and aching as his thumb rubbed relentlessly over the erect nub, urging, forcing her nearer and nearer to an unwanted orgasm.
"Ooohhhhh, oooohhh!" Her lips parted, a low groan echoing in her throat.
She was momentarily relieved of the pain in her anus as the pressure in her loins reached a breaking point. She looked up at Duncan wildly, her eyes glazed with passion and pleading with him to forgive her as she gasped and moaned and felt the cruel hard relief of climax flooding her whole body.
"I'm cumming… cumming," she gasped, as he held her firmly implanted between his thick, fat prick and his skilfully working fingers.
"That's it," he crooned, "Oh, so nice… that's it!"
He had accomplished what he wanted to do, humiliate her, shame her then satisfy her In front of her boyfriend. She had submitted to her animal instincts and she was subservient to him. He had done it!
He pulled his fingers from her throbbing, sated vagina, and grasped her thighs, wiggling his hips up against her buttocks, letting the head of his penis stay deep inside her.