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This story deals with betrayal, cheating, and infidelity. If that’s not what you like, then you’ll probably want to read a different story. This chapter picks up almost exactly where chapter 4 left off. Like the preceding chapter, this one consists in relatively short scenes involving Ian and Jess as their relationship progresses. I initially intended to have the next chapter be the last, but both of these vignettes wound up longer than expected, so there may be two more.
As ever, many thanks to the reader who proposed the idea for the story and whose input has helped guide me as I wrote.
Feels Like the First Time
Jess whimpered, a bit pitifully, as Ian’s cock head forced its way into her virgin ass. This, she thought, was worth it.
Not half an hour earlier, her lover Ian had fucked her cunt hard and hosed her down with cum, and she’d decided to taunt him with the prospect of fucking her ass. Ian leaped at the bait and now, she was bent over on her mattress, her pert ass up in the air, her cheek pressed into the mattress, her hands clutching feebly at the sheets as Ian opened her up.
She’d put her first toy in earlier that day, a slender, silver butt plug with a crimson rhinestone on its flared base. Ian had been enthralled by it. When she’d presented her ass to him, just after he’d fucked her pussy with his monstrous cock, he’d been unable to look away. And when she said to him, with her quiet, soft, innocent voice, “Please, sir, don’t take my last virginity. You’re too big for me. You’d have to hold me down and work it in.” he had lunged, practically knocking her over out of eagerness to break in her last unsullied hole.
Everything had gone according to plan.
Jess had wound up bent over Ian’s knee, her bare ass in the air and his engorged prick pressing insistently into her stomach. She’d squirmed on his lap, not seriously trying to escape (not that she could, if he really wanted to pin her down). A few stinging slaps to her ass made her settle down, and she stuck her lower lip out at him in a pout. “Have I been a bad girl, sir?” she asked.
This was a new game for Ian, but he took to it gracefully. “You’ve been a tease, baby. If you’re gonna tease, you’ve got to please.”
Jess shook her ass as she replied. “I’ll do my best, sir.” That’s when Ian started spanking her. It was a novel experience for Jess. Ian had decided, some time ago, that he wanted to live out all of her boyfriend Kyle’s fantasies, and Jess agreed to make it happen, delighting in the secret knowledge that her lover was living the life her boyfriend wanted to have.
One of those fantasies was to take Jess’s anal virginity. Kyle had let slip that he wanted to try spanking her as well, but she had never let him, telling him it was degrading. But somehow it wasn’t degrading when Ian did it; she felt comfortable and safe with him, and she was able to indulge her own baser nature without worrying about being judged.
So when his hand cracked against her ass, she felt the pain, but she also felt something else—a frisson of excitement and exhilaration that left her breathing hard and writhing in his lap. He followed each stinging slap with a brief squeeze of one of her tight, firm cheeks, giving her a sort of mini-massage to ease the pain. Before long, Jess found herself eagerly anticipating each slap, her pussy clenching as soon as the blow fell. Her little squeals and whines became moans of pleasure, and before long Ian’s caresses got longer and the slaps less frequent, until he abandoned the pretense entirely and just slid two long, dexterous fingers up into her and probed and stroked her until she gushed all over his hand.
She was still bent over Ian’s knee, enjoying the afterglow, when she felt him tug at the plug in her ass. Jess bit her lower lip as she felt the widest part of the toy slip out of her, slowly, pulled free by Ian’s strong hand. Her tight rosebud showed no sign that it had been occupied, instantly shrinking back to its normal size.
Jess looked at the scene in the mirror. The toy had been part of a set, designed to train people for anal sex, and she’d just slid the smallest toy into place earlier that day. The other three plugs had been on her nightstand, in easy reach of the bed, and Ian hadn’t failed to notice them—or the bottle of lube she’d bought at the same time. He picked up the lube and the next largest toy, a shiny silver plug as thick as two of her fingers at its widest point and about five inches long, with a deep green rhinestone set in its flared base.
Ian held the toy over’s Jess’s ass and drizzled lube all over it, the excess spilling off and coating her ass, making it slick and shiny. He took a moment to rub her ass. Both of them enjoyed the sensation of his rough hand gliding easily across her smooth skin. Jess flinched when he drew near to her asshole, but managed to keep still enough as he circled that tight rosebud with his fingers, coating it with lubricant.
“Are you going to train my ass, sir?” Jess said. Ian’s otele gelen escort cock throbbed against her, hearing those filthy words spilling from her mouth in her innocent-sounding voice. Ian didn’t say anything in response. Instead he took the plug and held it up to Jess’s asshole, lining it up with that tight entrance and pushing gently. Jess bit her lower lip as she felt the pressure mount until her ass opened just enough for the toy to penetrate her.
The tip slid in, and Ian kept pushing as Jess felt her ass spread to accept to invading implement. She’d gotten accustomed to the smaller toy, but this one was longer and wider, and Jess could feel the first faint twinges of pain as the toy spread her open and penetrated deeper than its predecessor. But that faded quickly, as soon as Ian slid the widest part of the toy inside her. Jess’s tight asshole immediately clenched around the thin part of the toy, just above the flared base; she felt curiously full, but it wasn’t an unpleasant sensation.
“Very good, babe,” said Ian. He twirled the end of the toy, making Jess aware of the minute imperfections in its surface as it spun on its axis inside her. Then he slid it back and forth slightly, not enough to pull it out, but enough for her to feel a faint tug as the wide part of the toy tried to escape from her tight grip. “How do you feel?” asked Ian.
“It feels good, sir. I think I can try a bigger one.”
Ian nodded and slowly slid the plug out of her. Jess felt the same things she’d felt when he inserted it, but in reverse—a faint hint of pain when her asshole stretched around the widest part, and a diminishing sensation of fullness. When it was free, Ian set it down beside its smaller companion. Jess expected him to grab the third toy, but he surprised her, going instead for the fourth and largest plug. This one had a sky blue rhinestone on its base, and it was as thick around as three fingers and about seven inches long—still not as big as Ian, but big enough to be scary.
Jess watched in silent anticipation as Ian coated the toy thoroughly in lube, again letting the excess run off onto her ass. Ian caught her eye in the mirror and raised one eyebrow. She just nodded, a bit hesitantly, and gave him a small, brave smile. The toy was a bit cold when Ian brought it to her tight hole, and she shivered when it made contact.
Even the tapered tip of this plug was larger than the small toy she’d experimented with earlier in the day. When Ian started to push it into her, Jess grimaced. There was no way something like this could fit inside me, she thought. But Ian stroked her hair, and slowly worked it into her over the space of perhaps five minutes. By the end of the process, Jess found herself breathing hard, but not in pain—Ian’s touch and indeed his mere presence exerted a calming effect on her, and once she relaxed the toy slid in easily.
The two of them formed a stationary tableau for a few minutes, with Jess bent over Ian’s knees, slightly flushed and sweaty, the glittering blue stone nestled between her cheeks the only external evidence of their recent efforts. Ian’s cock was pressed up against her stomach, and he hadn’t gotten any softer as he slowly stretched her out. If anything, Ian was harder now than she’d ever seen or felt.
Ian started to play with the toy, just as he had done with its smaller brother earlier. He twirled it in place, pulled it out partway before sliding it back in, pushed it in deeper with his thumb. There was some pain from his ministrations, but Jess found she kind of liked it—the pain provided a counterpoint to the other (vastly more powerful) pleasurable sensations. She reached down, between Ian’s legs, and started to stroke him as best she could in her awkward position, trying to jerk him off in time with his actions with the toy currently lodged inside her.
Before long, both Ian and Jess were too excited to be satisfied with this gentle play. Jess wasn’t sure if she could take Ian inside her unused ass, but she knew she had to try. And she somehow knew he wouldn’t hurt her; if she couldn’t handle his size, it wouldn’t mean the end of their relationship.
She nodded at him in the mirror. “I’m ready,” she said, her voice quavering with nervous energy. Then she slid off his knees and climbed back onto the bed, facing the mirror on the door, her ass toward Ian. That’s when she was reminded that Ian had never closed to door to the hall all the way. Not too long ago, the thought that someone might have heard her cries during their earlier fuck, or that someone might nudge the door just a bit and get an eyeful, would have made Jess terrified. But after Ian had fucked her in a restaurant while her boyfriend sat, unknowing, less than twenty yards away, she’d been secretly turned on by the notion of public sex. So she did nothing.
Ian took up a position standing behind her and eased the large toy from her tight ass. She seemed to be unwilling to let it go, and Ian pendik escort had to pull harder than expected to get the plug free. Jess moaned as it came loose. “It was just getting used to feeling so full,” she said, teasingly. “You’d better put something else in there, sir, before I forget how it felt.”
Ian smiled and poured yet more lube over his own cock, working it up and down his length with long strokes of his hand. Moving slowly and carefully, he positioned himself behind Jess, lining himself up with her tight rosebud, which was itself slick and shiny with lube and slightly distended from their recent endeavors. He pushed, gently but firmly. Jess let out a little squeal and tried to relax. She could feel her ass opening, yielding to his insistent pressure.
Aside from Ian’s sheer size, the biggest difference between his cock and the plugs they’d been playing with was that the plugs tapered to a fairly thin point, and didn’t immediately swell outward to their full size. Jess felt she had some time to get used to the size of each toy. But Ian’s cock didn’t afford that opportunity. By the time his head had pierced her tight ring, she was breathing hard, and her eyes were squeezed shut—partially from pain, but more from concentration. Jess knew that she had to fight her body’s natural reflex to resist and try to force Ian’s intruding member out, or she’d be much worse off. So instead she focused on her breathing and forced herself to remain relaxed, even as Ian slid himself deeper and deeper into her, inch by inch.
She was dimly aware of Ian muttering words of encouragement to her. Time passed—she didn’t know how much—and Jess realized that Ian had stopped moving. His hips were up against her, his body warm and comforting, and she felt stuffed full. Her face was turned down toward the bed, and she had gathered up great handfuls of her bedding in her white-knuckled grip. She forced herself to look up, and in the mirror she saw Ian smiled beneficently at her. “You okay, babe?” he asked.
Jess smiled, a bit weakly, and nodded. “Give me a minute to get used to it?” she asked.
“Of course,” replied Ian. “Tell me when you’re ready.”
Jess closed her eyes and concentrated on the steady rhythm of her breathing. She loosened her grip, extending her fingers until she had her palms down flat on the mattress. There was tension in the small of her back and in between her shoulder blades; Jess felt it dissipate as she breathed in and out, steadily. There was some pain where Ian was stretching her, but rather than dissuade her, the pain made Jess hunger for more. She was just about to give Ian the okay when he started moving on his own. He had read her responses and knew that she was ready, even without her say-so.
He rocked his hips back and forth, slowly, in small movements. And before long Jess found herself moving as well, rocking forward when he moved back, making his thrusts longer and deeper. Even when he was stuffed deep in her ass, Ian was more than big enough to stimulate her cunt as well; she felt faint tingles of sensation when he bottomed out in her. Jess slid one hand between her legs and, after briefly fondling Ian’s oversized balls, she started to rub her clit in a circular motion.
“Good idea, babe,” Ian said, as he picked up his pace. He was sliding a bit more than half his length in and out of her with each stroke now, and with Jess pushing back against him, their hips met with an audible smack each time they reconnected. She could feel him lean forward and reach for something, before he reached around her and pushed her hand out of the way. A faint buzz came up from between her legs as Ian pressed her little silver bullet against her clit, and Jess moaned as it sent waves of pleasure through her body.
She closed her eyes, and Ian sped up again, taking her ass with long, deep strokes. Jess lowered her cheek to the mattress, leaving her ass up in the air; the change in position made Ian’s thrusts seem to go deeper, and each time he hilted himself in her his sack swung forward and just barely kissed her slit. She could feel her legs spreading further apart, lowering her hips, giving him easier access, and as she slid down Ian’s thrusts got more and more powerful.
Jess drifted off on a cloud of sensations—the overstuffed feeling of Ian’s cock in her ass, the tingling pleasure of him sliding in and out of her stretched slick rosebud, the curiously muted sensations in her pussy as his thickness impinged on those nerves, and the humming delight between her legs from the little silver toy pressed firmly against her button.
A small sound from the hall outside her door made snap her head up. She pushed herself back up, in the process driving her ass back toward Ian. “Well, looks like you’re ready to get going for real,” he said, before redoubling his pace.
Jess’s head dropped again for a moment and she gasped at the sudden assault and the sharp spike of euphoria that accompanied it. When rus escort she raised it once again, she saw something disturbing: her door had been opened partway. Ian had left it cracked, but now it was open about an inch, more than enough for someone in the hall to see in. And the hall lights were off. But Jess was sure she saw movement in the shadows, just outside her door, some sort of small rhythmic motion. “I think someone’s watching us,” she said between thrusts.
“Good,” said Ian. “Let’s give them a show.” He reached forward, grabbing a handful of Jess’s long dark hair, the pencils that had been holding it up having long since fallen out. He hauled back on it, forcing Jess’s head up and her face toward to partially-opened door. He started to fuck her harder, letting out small grunts of effort as he hammered home. Jess felt herself rocked forward by each thrust, and it didn’t take long before her eyes started fluttering as she came.
She bit her lip, determined not to make her climax obvious to the unknown onlooker, but Ian kept pounding her, and her little silver bullet was right there on her clit, and she felt so good, and she felt the long moan escape her lips before she could bite it back.
“Look at yourself,” Ian hissed. Jess did, gazing into the mirror. Her face was flushed, her mouth hung open, and her skin glowed with exertion. The flush covered her whole chest as well, her nipples were proud and stiff, and her tits swung freely underneath her as Ian sped up once more, fucking her ass now like he did her pussy. Some part of her was astonished that she was able to take such a massive dick in her ass. Ian was behind her, the lean muscles covering his arms and chest standing out as he hauled her back onto him. Jess had to admit that watching them fuck was hot.
Still, she wasn’t quite able to let go. “What if it’s Kyle? Or one of his friends?” she said, haltingly, pausing every few words to gather himself as another orgasm approached quickly.
“They’ve been there for ten minutes.” Ian said, quietly. “Just watching. Maybe we should invite them in.” Jess moaned. “Give them a real show.” Jess’s eyes closed and she came, thinking of the many times she’d fingered herself while watching in the mirror and the video she’d made for Ian. Could I be an exhibitionist? she thought. The shiver of pleasure that went up her spine at the thought gave her a definitive answer.
Jess opened her eyes and looked out at the shadowy figure in the hall. With a wicked grin on her face she crooked two fingers, beckoning whoever was out there watching inside.
The watcher came in, closing the door behind her. Their audience was a woman; she was short and mousy, and when she came in she had her eyes downcast, refusing to make eye contact with either of them. The voyeur was Asian, with glossy black hair and a heart-shaped face. She was wearing thin, black-rimmed glasses, a loose-fitting t-shirt, and pajama pants. The pants were pulled down slightly and were askew, providing a good view of one hip and a faint hint of the thin line of dark hair above the newcomer’s pussy.
Jess’s jaw dropped in surprise. The watcher in the hall was Ella, one of her best friends. Ian saw her reaction. He slowed down, his cock sawing out of Jess’s ass at a considerably slower pace. “So, you two know each other?” he asked, turning Jess’s head to look at her friend. Ella nodded shyly. “Do you think Jess is pretty?” Ella nodded again, blushing slightly. “Did you like watching us?” Another nod as the blush deepened. “Were you touching yourself?” Ella looked down at the floor, and her blush became almost crimson—it wasn’t a nod, but her reaction and her disheveled state made the truth clear. “Well, don’t let us stop you. In fact…”
Ian’s voice trailed off, and he released Jess’s hair. He pulled out of her ass, and Jess found herself moving back with him, trying reflexively to keep him inside her. But he was faster, and he extracted himself, leaving Jess feeling curiously empty. He gave her a quick, light slap on the ass, making Jess jump slightly, and said “Get up, babe. I think you should run the show for a while.” Jess rose, not quite sure what he meant, and Ian slid into her bed, his back up against the headboard, his feet toward Ella, and his monolithic cock standing proud, jutting up from his groin.
That’s when Jess got it; she got back on the bed and crawled slowly and seductively toward Ian. She knew Ella must have had a great view of her freshly-fucked ass and her dripping pussy as she crawled, and indeed she could hear Ella’s breath quicken slightly. Jess dropped a bit lower, dragging her breasts up Ian’s legs, trapping his shaft between them briefly (she could feel his pulse then, against her breastbone) bringing them up his chest to his face, then pulling away when he tried to snare one of her nipples in his teeth.
She ground herself against him, his cock nestled in the cleft of her ass, her pussy mashed against his pubic bone. They kissed again, and as they did Jess reached back to grasp Ian’s cock and slide him back into her ass. But Ian stopped her. “No,” he murmured. “Face her.” Jess broke into a broad smile and turned. Ella was leaning against the wall opposite the bed, still blushing deeply. She had slipped one hand into the front of her pants and both Ian and Jess could see her fingers moving slowly underneath the waistband.
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