Chapter 9
"What's the meaning of this?" Gail asked, frightened by the two drunken men being there.
"Hey, Gail-baby," Sidlander smiled. "This here's Tom Kobich. He's in the same line as me. He's just as good a broker, too. He came up here without any female companionship, and I figured it wasn't fair for such a nice guy to be lonely, so I offered to share you with him."
Kobich was young, with black hair that came down past his ears, a scraggly mustache, and sharp features, like those of a ferret. It was obvious he was the kind of man who didn't give a damn about anyone or anything other than Tom Kobich. Had Sidlander not been so drunk, he'd have never brought Kobich into her room.
"Mr. Sidlander, I'm not some kind of pet with which you can play," Gail insisted.
"Aw c'mon," Kobich smiled, and even his grin was crooked. "I'm a lotta fun. And what's more, with two guys you can really ball it up."
"I'm not in the mood to ball it up," Gail insisted. "I don't even know you. Please leave."
"The heck I will," Kobich said, smiling even more widely. "Sid, here, invited me to enjoy you along with him, and thass jus' what I'm gonna do, honey. You're prime stuff. And I'm gonna fuck at least one of your pretty holes before I take off."
"Hey, yeah," Sidlander nodded. "I've only fucked her cunt, so far. She has two other holes I haven't even tried."
"No!" Gail all but screamed. "No! You can't do this!"
"Oh yes we can," Kobich snarled, winking at Sidlander, and with that, the two men began stripping off their clothes.
Gail stared from one man to the other, noting the immediate contrast between them. Sidlander had a heavy, almost porcine body, with a massive white cock topped with a red crown, sticking out from under his swollen belly. He had light-brown hair all over. Kobich, on the other hand, was white all over, except for the black hair on his head, under his arms, and on his pelvis. He had no chest hair, and no hair on his arms or legs, as if the female hormones in his body were a lot stronger than they ought to have been. Though Sidlander looked more ridiculous, Kobich looked to be the more dangerous of the two men. There was no doubt his penis was the uglier of the two shown. It was chalk-white, with deep blue veins winding a gnarled path from top to bottom, and the glans was almost cherry it was so red.
Gail had expected the two men would caress her and make her at least want something before doing anything, but Kobich was a totally selfish individual with no thought other than his own satisfaction'. He tossed Gail onto her bed, spread her thighs wide apart with his hands, then scrambled between them before she had a chance to clamp them shut.
"You'll kill me," Gail screamed, as Kobich pressed his skinny knob against her dry pussy.
"Well hell!" Kobich snapped. "Can you think of a better way to die? Who the hell are you, thinking you can get off without putting out for me? Keep that cunt wide open, bitch!"
"You're a real bastard," Gail sobbed, feeling the skinny, dry prick slowly stretching her unmoistened mucous membranes as it pushed its way violently into her.
"With cunts like you, there's no other way than to treat you like this," Kobich snarled. "You think your pussies are so holy and sacred, when all they are are holes between your legs, waiting to be filled up by the nearest available cock."
"Do it and get it over with," Gail sobbed.
"Oh shit, no!" Kobich told her. "This is only the start of something good." Looking up at the drunken Sidlander who had been watching the entire time, he said, "Hey, Holly, you said you'd never fucked one of her other holes. Now's the time to start. How'd you like to fuck her ass?"
The remark seared into Gail's spinning mind. Were these two men totally insane? Kobich was already cramming his thin, stiff cock into her with his efforts, and how he was suggesting that Sidlander, who had a massive cock by comparison, shove his meat into the narrow rictus of her rectum. True, Sam had occasionally fingered her asshole while he fucked her, and she had to admit it had felt good. But a cock as fat as Sidlander's would never fit inside her anus. Even Kobich's, which was far from fat, would have difficulty fitting into her asshole, but Sidlander's was impossible.
But even as she thought these things, Gail saw the way the man's eyes lit up. Sidlander liked the idea. He was panting loudly, more out of breath from having had too much to drink than anything else.
"You know," Sidlander said, his gravelly voice echoing in the room. "I think that's just what I'm going to do."
His large, fat penis was leaping up and down with throbbing anxiousness. Lord! It seemed even more immense, with the bright-red tip shining until it seemed as if it were a beacon. And the more he thought about sodomizing Gail, the more it vellicated. Gail saw how fast it was vibrating, and knew there was no way out of this. She was certain her body would suffer physical damage, and seeing the way the man trembled, she knew the more she screamed, the more Sidlander would enjoy it. Drunk, he was revealing his true character to her. He wanted the pleasure of feeling her tight asshole squeeze the entire thick length of his throbbing cock.
"Roll her over," Sidlander said to the skinny, evil man whose equally skinny cock had already sunk its full length into her squeezing pussy. "I've always wanted to fuck a tight asshole, and I think Gail has just about the tightest one around. It'll be a pleasure."
Gail heard the trembling lust in Sidlander's voice as he ordered Tom Kobich to turn her over, and she was more afraid than she had even been in her entire life. Kobich slammed his skinny prong as far into her as possible, painfully massaging her dry membranes again and again, sighing and gasping as he nailed his thin wand deeper. He pushed again and again until he was certain every last little bit of his exceedingly skinny penis was totally buried in the agonized woman. Gail had tears streaming down her cheeks. She felt the man roughly tug her against his body, clinging to her tightly as he rolled a full hundred-and-eighty degrees. Now she was the one on top, sitting upright on the skinny whang uncomfortably probing inside her. Kobich's hands gripped her taut ass-cheeks, keeping her firmly held in place.
Gail felt utterly humiliated and ashamed for the first time since she and Sam had first started fucking. Whatever she had done with the shoe-repair man had felt good, and she wasn't the least bit ashamed of it. What she had done with Sidlander she had done with the idea of it leading to matrimony, and so there was no shame there, either. But with Kobich, a complete stranger, a man with whom she wanted nothing to do, she felt terribly humiliated. Her pussy passage was all aflame, but not with desire. It was aching with agony caused by the prodding and stretching attack of Kobich's cock. And now her twin-mooned-buttocks were sticking up in the air as Kobich pulled her head down and clamped her mouth around his. She groaned, feeling Sidlander kneel behind her.
"Please, Holly," she begged, tearing her mouth from Kobich's foul-tasting lips. "Please don't do this. I never did anything to hurt you. When I came along, it was with the idea it would only be you and me. Please, Holly, this'll kill me."
Her mind was whirling, a mass of totally confused apprehension. How was she going to look Sidlander in the face Monday morning, when she went back to work? How did she dare return to that office? Now she wished she had taken Rona up on her offer to leave. In fact, when this was over, if she was still alive, she'd go find Rona, and take off with her.
But even as these thoughts roamed through her bruised mind, she felt the swollen pulsations of Tom Kobich's throbbing penis, and she understood her body, disobeying the orders from her brain, was becoming unwittingly aroused. Little by little there was seepage in her tight vaginal corridor. The walls were slowly being oiled. Her internal body was naturally responding.
Kobich gripped her tightly, his long, skinny cock deeply impaled to its full length in the slowly oiling depths of the woman's aching, shuddering vagina. His hard, bony knees kept her soft, tender thighs licentiously spread wide apart, her small, puckered, prune-like nether hole completely exposed to Holly Sidlander's perverse and wanton assault. Gail felt completely helpless. She was shuddering, quivering, moaning, knowing nothing on earth would save her from the terrifying drunken lust of the two men.
Sidlander moved between her vibrating, wide-apart ass-cheeks, pressing his hungering mouth above the spot where Kobich's cock was already buried in her cunt. The angle at which Kobich had Gail was such that the smooth, white, rounded moons of her tender buttocks were pulled very wide apart, exposing the tiny brown crinkle of her virginal asshole. Sidlander was able to see the budding hole wink at him in the moistened cleft above the greased penis moving up and down inside the nibbling lips of her hair-lined vagina. He stared at the way Gail's narrow cunt, which had widened to take his own cock, now tightened around Kobich's instrument, sucking, slurping as juices ran down the whang in heavy droplets. But that ass . . . well, that was something else again. It was a much narrower hole than her pussy, and he was willing to bet she had never been juiced there. God! Her cunt had been a tight fit for his cock. Her asshole was going to be an even tighter fit.
Without saying a word, he extended his forefinger and probed into the snug, rubbery closeness of her resisting rear passage, deciding to widen it a little before cramming his throbbing cock inside. Hell! If he didn't stretch it a little, he might never be able to force his penis in there.
"Unnnngggghhh! No! No!" Gail was begging, squeezing her sphincter tightly shut, using all her strength. As a result, she felt a bit of pain when Sidlander's finger finally moved through her resisting rubbery doughnut. Even then, her body trembled with inner lust imploding through her. And as the digging finger pushed deeper, she began feeling more licentious anticipation.
God! She was too wanton, too free with her body Now she was paying the price. Sam had been good enough for her. She ought to have stopped there.
As the thoughts of Sam ranged through her head she heard Kobich saying to Sidlander, "My own business has fallen way off this year. I'm thinking of going into selling used cars."
"I know," Sidlander grunted, ramming his finger even farther into Gail. "Insurance is a risky business. Hell! The only safe businesses left are certain neighborhood retail stores, like local clothing stores, hardware, and fast foods."
And shoe-repair, Gail thought. Sam's might not have been the most lucrative of businesses, but it was a steady business, a dependable business. He'd be working at his trade long after men like Sidlander were looking for other jobs. God! What a fool she had been. When this was over she was going back to Sam, and she would get down on her knees and beg him to marry her.
"Unnnnnnggghh!" she grunted as Sidlander crammed his finger as far into her rectum as possible.
Damn! she thought. The man was intent on stabbing his thick cock into that tiny hole where his finger barely fit. Hell! He wasn't even moistening her asshole, just probing the dry tightness with his finger, sawing it back and forth, back and forth, tugging from side to side, trying to widen it. Gail was well aware the drunken Sidlander wasn't doing this out of consideration for her. He wanted to fit his thick cock in there, and there was no way it would go in without her asshole being widened, first. And once he did force his phallus into her rectum, pressing against the thin membrane separating her ass-channel from her vagina, it would tighten her cunt even more, creating more pain in there, as well.
There must have been a latent streak of masochism inside Gail, because the idea of what was about to happen seemed to heat her up all the more as Sidlander's finger wormed even deeper into her defenseless asshole. Little by little her rectal oval was widened and enlarged, the muscle being made more elastic so it would resist the pressure of his thrusting cock that much less when the time came for him to enter her, there.
Gail felt Sidlander adding a second finger to the first, pushing it in as far as possible, and turning her head, she saw the anxious look in the man's eyes. Yes, he was hungry to fuck her rear passage, all right. Odd, but the idea of poking his hard cock into her back tunnel might never have occurred to Sidlander had Kobich not suggested it. She saw the two men were not merely intent on satisfying themselves, but they wanted her to enjoy the robbing of her dignity. She wondered if all insurance salesmen were so callous. She knew Sidlander gave special tests to the salesmen who joined his brokerage operation. She wondered if questions pertaining to cruelty was part of the exam. A man like Kobich would pass with flying colors.
In vain, the young mother attempted to wiggle her assliceeks trying to pull away from Sidlander, hoping to escape the unnatural assault of his probing fingers, but it was to no avail. The man was ramming both fingers in and out with greater rapidity as her asshole widened, becoming accustomed to their breadth.
Gail felt strong pressure as Sidlander's fingers touched the inner membrane separating her cuntal tract from her anal tunnel. She sensed the way Sidlander's finger actually touched Kobich's thin cock, with only that thin bit of tissue separating them.
Sidlander was unable to restrain his cock any longer. He pulled his two fingers from the tight clutch of Gail's rectal passageway. They made a lewd "pop" as they came sliding out, and the sound seemed to excite and arouse Sidlander all the more. His throbbing testicles felt as if they would burst inside their leathery sac if he didn't finally poke his penis into the crushing asshole.
Gail felt herself being tugged more tightly against Kobich's skinny body, and at the same time she felt Sidlander lean across her smooth, spine-ridged back, his light-brown, steel wool pubic hair scratching the tender softness of her smooth, silky flesh. She felt the man place the rounded dome of his lasciviously swollen prick between the cushion-like cheeks of her tender buttocks. It pushed into the soft, yielding crevice, rubbing against the prune-like rectal pucker. Kobich gripped Gail very tightly, keeping her from wiggling around, and Sidlander began slowly pushing forward. The gigantic, thick penile point began forcing its way into the narrowness, enlarging and stretching the tiny opening as the reddened tip of Sidlander's phallus wildly pulsed with obscene anxiety.
"Ggguuunnnggghhh!" Gail gasped, feeling the weighty force behind her employer's thrust as he relentlessly and mercilessly expanded the tightened ring of her narrow sphincter.
Gail was trembling more and more violently, wondering if she was capable of surviving this torture. It was so evil, so obscene, and yet, deep down, she had to admit, in spite of the pain it was terribly arousing. But the pain was strong, very strong, much stronger than anything her impassioned body had ever felt before. She felt Sidlander press continually forward, probing with all his strength, and the hurt became too much. She knew her body was too tender and fragile to withstand all this. Sidlander would kill her by tearing out her intestines.
"Eeeeyyyaaaggghhh! uuuunnnggghhh! No more! Please!" she begged.
She was wildly screaming in useless protest, trying to pull away from the ever-increasing pressure as mounting torment continued burning its way through her soft, agonized body. But the two men had her firmly locked between them, and she was helplessly restrained. She knew the suite was soundproofed, so no one was able to hear her screams. ignoring Gail's squealing, piteous cries, Sidlander jammed his licentiously excited hips forward, using all his energy. He pushed again, then again, and felt her tightly clenching anal sphincter suddenly surrender to his brute force. Shoving with all his strength, he rammed his weighty cock-head into her narrow, wickedly stretched anal channel, feeling the rubbery ring suddenly close tightly behind the corona like a bear trap.
"Ggguunnggghh!" Gail gasped, as her speared buttocks were tugged farther apart and her rectum was widely stretched as never before. The pain of his pederastic attack seemed to blast into her brain with the force of a locomotive. She desperately and anxiously did her best to free her body, but there was no escape from the wickedly probing prick.
But behind the agony there was still a series of thrilling sensations, and now they began slowly mounting, while the agony began slowly decreasing. The pain was still there, but it was lessening. There was a sudden conflict between torture and the strong, diffused sensations of licentiousness. Yet somehow it appeared to be the natural culmination of everything happening to her. She was unable to comprehend why, but Gail suddenly stopped struggling and resigned herself to accept what was happening to her.
Sidlander felt the surrender of her tender body, and he attacked her anus even more strongly with solid, thrusting drives, lifting his belly out of the way. He nailed his stolid poker of steaming solidity three inches deeper into her flaming tunnel, gasping as her hot, rubbery sphincter clutched the pole, and Gail screamed again. Her strong, rubbery ring once again clamped tightly around the thick, massive cock, but the pressure merely aroused Sidlander that much more. He'd show this bitch who was boss. In the office or out, he was the one who made the decisions. He didn't like the idea of her rebelling. Hell! Just because he was asking her to do a small favor for a friend was no reason for her to act so uppity. Hell! A good cock in the ass was just the thing to teach this sweet little bitch that she had no right to refuse any request he might make. He'd jam the entire cock up into her colon. Not that it was long enough to really do any damage up there. The colon was deep, very deep. He'd need a twenty inch cock to really reach all the way into it. But it felt long enough to delve far enough into her to give him a maximum pleasure. So he shoved again, and the soft, tender walls of her rectum, now being lubricated by the leaking emissions from his throbbing cock, seemed to yield more willingly, and his large belly now rubbed against her back while his heavy thighs pressed against her white, shimmering ass-cheeks.
"Oooooonnnggghhh! Godddd!" Gail gasped. "Ohhh-hhhhhh! Haaaaannnnhhhh!"
Gail felt as if a hot, thick poker had been violently and wickedly thrust into her rectum. It plunged deeper and deeper, separating her anal walls, making her feel as if she were being wedged apart. Her trembling thighs were stretched to their utmost. This was the most monstrous thing anyone had ever done to her. The cock in her cunt was no less monstrous than the one in her ass, since neither had been "invited in." The intent of the two phalluses was the satisfaction of the men attached to them, with no thought of pleasure for Gail. She was helplessly sandwiched between them.
The initial pain in her rectum was easing, softening somewhat, but the overpowering, raging heat enlarging in her body continued swelling. The thrills were heightened to a fantastic, rapturous sensation creating a blend of pain and passion. The tremulous shudders shooting through her trembling colon seemed to swell and enlarge with each passing second.
"Come on," Kobich snapped to Sidlander. Being underneath the two of them, he had to bear the weight of both of them. "Start pumping, already."
"Christ!" Sidlander gasped. "I never dreamed an ass was this tight. Jesus! This is amazing."
Gail felt his thick, buried phallus solidly held in place by her gripping rectum and twitching colon. The raspy voiced man was grinding against her as if trying to power his massive truncheon through her colon into her stomach. By now it was as far inside her as it was going. Gail felt a tingling thrill brought on by the poking head of his solid prick as it swelled and enlarged even more. He was arching his hips back, awkwardly attempting to match the rhythm of Kobich's prick as the latter fucked into her frothing, soaking pussy.
Gail's pink tongue moistly circled her parched, cracked lips. The tension inside her became greater and greater as the pain receded. Little by little the agony faded until it had completely disappeared. All Gail was now able to feel was the total, wonderful, rapturous impalement of two prongs in her trembling body.
Gail thought of herself as a single receptacle with many orifices. Her brain, her hands, her feet, her nipples, even her fingers and toes were all part of the receptacle making up the individual known as Gail Roberts. She was all hollowed out, waiting to receive the spurious flow of masculine sperm about to be ejaculated by two moving penises. At this point, she had become so aroused, she was willing to take even more penises into her body. She had never filled her mouth with one, but at the moment she was willing to try. She'd have loved to have fitted one into her navel, two more in her nostrils, and another pair in her ears. She ached to clutch two more with her hands, and wanted to wrap her toes around another two. Unalloyed pleasure was now rampantly charging through her throbbing body. The more insane, the better. The two, throbbing, moving, working penises continually and relentlessly drove into her responding orifices. The thicker one in her rectum seemed to fit in so nicely, now. It plowed back and forth, matching the simultaneous movements of the prod in her teeming cunt, mounting thrills of burning passion through her entire torso. Gail felt as if she were being buffeted about like a paper boat on a surging ocean as the two men furiously strained toward their satisfaction. The woman insanely undulated her sensuously anxious body between the pair of men, her rounded white buttocks moving in maddening circles.
"Ohhhhh Goddd! Yes! Yes! Yes!" Gail screamed, "Fuck me, you bastards. Fuck me, hard! Come on, the pair of you . . . fuck . . . fuck . . . fuck.. . "
Gail was screaming at the top of her lungs, shouting at the two insurance brokers, and the two men wildly responded to her shouts. Each was anxious to prove his eagerness to grant her request. Their rhythm was working perfectly, now.
Gail was overjoyed. She was going to have a climax with a penis in her vagina, though she knew it was the one in her rectum stimulating her body to achieve its satisfaction. Without the one burrowing through her asshole, the penis in her vagina was almost totally useless. And Tom Kobich was not the kind of man to give her satisfaction after he, himself, had come.
Kobich's hips were angling up, slamming the meaty prong higher and higher into her tight vaginal maw, while at the same time Sidlander's thick cock was cramming itself down into her taut anal causeway, hotly sinking into the fleshy corridor of her clinging, vibrating ass. The woman felt pincered between the two men, feeling their hot breath on her face and the nape of her neck. It was wilder than anything she had ever done before, and she made up her mind to enjoy it because she knew this was the last time she would ever do anything with more than one man. No matter how good it felt, she knew it was wrong, and as long as she hadn't promoted the idea of the two men taking her this way, her conscience would permit her to live with what was happening to her. But if it ever happened again, she didn't know if she'd be able to take it. So the smart thing to do was to enjoy what was happening to her now, while she was able. Neither of the two men was a great lover, but the combination of the two made all this feel much better than it otherwise might have felt. Each had a competent cock, and two satisfactory cocks were better than one good one. Fortunately, Sam had more than a good cock. He had a great cock. But at the moment her rectum and pussy were being squeezed all the more tightly. She was enjoying the deep probing of her body by the twin javelins, both desperately intent on unleashing the quantity of semen they contained.
Gail clamped her mouth tightly shut. Her own orgasm was very close, and she didn't want them to know of it. She felt it lurking somewhere inside of her, preparing to come out. Slowly the sensations within built higher and higher, and Gail felt this would be a fantastic climax. A thrill was enlarging in her rectum as well as in her vagina. One orgasm would set off the other. She was able to tell. Thrills mounted in her taut vagina and her ass at the same time. If she'd had a tongue washing over her clitoris, as well, she'd really go wild. A triple orgasm would have her jumping out of her skin. Nevertheless she was surrounded, drenched, and totally inundated with the near-epitome in licentious satisfaction as orgasmic sensations mounted, giving to her, and taking from her, both at the same time. She was being driven to ecstatic heights completely beyond believability. Her tongue had the taste of satisfaction on it, and her nose quivered with the scent of oncoming semen. Everything; semen, perspiration, and heated breath, seemed to melt with the wild, tingling sensations in her belly. Soon she would feel it all culminating in both, her squeezing asshole and her soaked vagina. It was complete, total fulfillment, and she was soaring higher and higher, the wondrous summit almost within reach.
Squeezed between the two male bodies, Gail trembled with powerful orgastic energy, her heated pussy and narrow asshole madly clutching and sucking on the two hot probes with an overpowering, strong, violent force. Her compressing movements were a trigger for all the electrical passion shooting through the three of them.
Sidlander's thick penis slammed far up into her large intestine, and he began shouting a loud, "YYY-YYAAAAAAGGGGHHHHHH!" while blasting his gushing cream into her belly.
Kobich's penis, feeling the throbbingly sensitive twitches of Sidlander's cock each time it spurted into Gail's narrow rectum, was incapable of holding himself off any longer, and he started blasting into Gail's contracting cunt, shouting, "GGAAGGHH!"
"EEEEYYYIIIAAAGGGHHH!" Gail screeched, feeling the orgasm in her rectum. She was set to climax in her vagina, as well, but Kobich's cock shrunk too quickly, and pulled out, leaving her somewhat unsatisfied and shaken. As the two men went to the bathroom, Gail knew she had to dress and get out of there.