"Just look at that hairless little asshole, boss," Andy panted from behind. "I'm gonna love doing this."
Tears of shame built up in her eyes as she felt his hands opening her buttocks, drawing the alabaster cheeks wide apart. She tried to hold them flexed together, but the pressure of his thumbs inserted in the crevice was too great. They were pulled away from each other until she could feel the cool draft from the air conditioner rushing into the hot valley between her thighs. Abruptly, Grace knew these beasts were not merely tormenting her; they were serious! And with that knowledge she began to struggle. "Oh, no. You mustn't. It isn't right. Please…"
Andy and Ricky both laughed in sadistic delight, with the little jockey saying, "What do you mean, it isn't right. Why asshole fucking is a great sport. You ain't trying to tell me that you've never had it this way before… that you're a cherry back here?"
"Oh, God… please. Don't!" The last was a yelp of fright as she felt his blunt middle finger begin to press against the tight, elastic little opening of her anus.
"Shut up, bitch," Andy snarled. "I asked you a question. Answer it." He shoved his finger hard against the tiny puckered opening, and the fingertip and fingernail disappeared into the soft rubbery mouth. "Answer me!"
"No…" she whimpered.
"No what."
"My husband has never done that to me."
"Done what to you?"
"That."
"What's 'that' mean?" The remark was a vicious snarl, demanding elucidation.
"Oh, God. You know."
Andy's arm muscles tightened and his thin lips suddenly whitened. He jabbed the finger in deeper and was rewarded by her shriek of pain. "Tell the boss here and me what you haven't done before. I'm not going to ask you again."
"No one… has ever… made love…" she corrected herself immediately, knowing they wanted to hear the obscene phrase and too frightened to defy them any longer, "No one has ever fucked me before there."
Andy grinned over at Ricky. "In that case, bitch, your education has been sadly neglected."
Grace felt the tip of his finger worming around at the entrance of her naked rectum, and she clenched the puckered tiny lips tight in a futile effort to prevent the perverted penetration she knew was coming. Andy probed for a moment at the inner edges of her anal ring and then grinning cruelly, shoved forward sinking the finger all the way up to the first knuckle. Grace jumped from the resulting pain, but it was not as bad as she thought it would be. She had begun to relax when she felt a second finger probing her opening, than that one rammed in alongside the first.
"Ummmphh," she groaned, her face buried in the cushion, feeling the hurt this time. She jerked her hips forward into the pillows in an attempt to escape the painful entry.
Andy wig-wagged his fingers in the depths of her rectum, stretching it wider and wider and was rewarded by a muffled cry of pain and abject plea, "Oh, please… don't. That hurts. Please…"
She turned her head sideways facing the back of the couch so that he could see her protest. Tears of shame and pain and humiliation streamed down her cheeks again as she realized that the act was really going to take place. He was going to push that long hard thick penis all the way into her virginal rectum in a parody of love-making that she had never before dreamed existed. This, then, was the finale of her humiliation and defilement, apt punishment for her sins of the flesh committed earlier as a result of her own moral weaknesses. Her body would be punished and used in the most obscene and degrading ways imaginable. She would never live through it, and even if she survived she would never be able to face herself in the mirror again. She attempted once more to bury her hips deeper in the pillows, but it was useless for he merely planted the palm of his hand on the small of her back and pushed down tight as his fingers dug deeper into the nether depths of her back passage, expanding it mercilessly in preparation for the coming assault.
"She's ready as she's ever going to be," Andy said suddenly, then withdrew his fingers, the elastic ring of the anal flesh clinging to them in seeming reluctance to let them go. He used his knees to force her legs wider, then bent down and deposited a mouthful of spittle in the crevice between her cheeks.
Grace felt his hairy loins pressing against her buttocks and the hair of his legs brushing against the insides of her thighs. She was held wide and helpless, completely at his mercy. Then, for the first time, she felt the long, thick cock pressing itself into the moist naked split of her behind. She cried out in fright. It was too big. She could never take that in her rectum without being ripped apart. "Noooo… please. Oh, God… have mercy… don't."
Andy's hands roamed over her buttocks, then his thumbs were pressing on either side of the puckered little hole stretching it wide. Abruptly, she felt a probing between the thumbs as his cock began a slow relentless pressure at the forbidden opening.
"Jesus Christ," Andy groaned with something akin to surprise in his voice, "it's even tighter than I thought at first. Feels like a fucking baby's mouth!"
Grace screamed again and groaned piteously, but the sound went unheeded. There was no one here who would help her… no one in the whole world. All that existed now was the excruciating pain where that barbaric instrument had lodged itself unnaturally into an opening that simply could not accommodate it. There was to be no escape from the horrible degradation of this demented, perverted attack on her helpless body. She continued to groan incoherently as the straining bookie popped the heavy bloated head relentlessly inside and pushed in deeper, deeper, deeper. God, it even caused waves of pain in her stomach as the rigid thick prick pushed and ground against soft buttery flesh inside her wide-stretched anal passage. She was stretched as she had never been before, impaled on a burning railroad tie. And then, just as she thought the torture would never end, she felt his coarse pubic hairs smack into the softness of her upturned ass cheeks.
The cruel barbarian's fleshy sword was buried to the hilt. Grace groaned in anguish, pinned to the couch by the rock-hard gristle of his cock like a butterfly specimen on a display board. She felt the need to fart from the pressure, but such relief was denied her because the mammoth prick effectively acted as a cork in her asshole.
Andy, his eyes rolling around in his head with delight, began sawing rhythmically and without mercy deep into the warm rubbery depths of her rectum, evoking further cries of shame and pain from Grace's contorted lips. Soon, muttering obscenities and gasping with sadistic pleasure, he started to thrust the full length of his punishing rod into her with long smooth strokes. It pulled tiny ridges of her brown sucking flesh out with the base of his prick as it withdrew, then shoved the anal ring back in out of sight on the vicious inward lunge.
Grace's body jerked and quivered, convulsing each time an extra hard thrust seared into her tortured asshole. She could hear his animal grunts of delight and hated herself and her body for the joy it was giving the vile unspeakable beast. She wanted to destroy him, kill both men for their brutal unfeeling defilement of her self-respect, but she knew she was defenseless, helpless, impotent to do them any damage.
Andy was near ecstasy as he felt the warm clasping flesh enveloping his sensitive cock from trunk to tip. It was as though he were fucking into a warm velvety glove that squeezed his prick unmercifully. "Oh, you hot little bitch, you," he crooned behind her, "if you only knew how good your tight little asshole feels. Shit, if I could figure out how to bottle it, I'd make a million dollars overnight."