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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 is a bit of an experiment; it’s a bunch of relatively short scenes, heavy on sex, involving Ian and Jess as their relationship progresses. Please let me know what you think.

And as always, many thanks to the reader who proposed the idea for the story and whose input has helped guide me as I wrote.


Date Night

Jess smiled sweetly at her boyfriend Kyle over her drink. He had been saying something or other about how happy he was to spend the evening with her, but she wasn’t really listening. There was a pleasant ache in her pussy from earlier in the day, when she’d found Ian and dragged him into an unused classroom for a quickie. She had grown accustomed to getting a good fuck from Ian at least once a day since she started cheating on Kyle with him, and she didn’t want to go without today—hence the risky classroom sex in the middle of the day.

While they had been getting their clothes straightened up after the quick, intense fuck, Jess told Ian apologetically that she couldn’t see him that night because she was going out with Kyle. It had been Ian’s idea that she should keep seeing him at all—after her first night with Ian, she planned to do the honorable thing and break it off with Kyle.

But Ian insisted that she keep stringing him along for as long as possible. At first, she had resisted, but before the night was out he had convinced her that it would be hotter if she stayed with Kyle. And indeed it was—Ian was her dirty little secret (well, dirty huge secret, truth be told), and every time Kyle complained to her about his roommate’s latest outrageous sexual conquest she got a little thrill knowing that Kyle was unknowingly talking about her.

And of course the fact that Ian said he wouldn’t fuck her at all unless it was behind Kyle’s back had influenced her decision as well.

To make this work, she had to keep stringing Kyle along. So it was that Jess found herself spending an evening with Kyle. He had taken her out to a perfectly serviceable dinner at the Main Street Grille, and now they were enjoying an after-dinner drink at the Blue Martini bar. They were sitting at a high table off in one corner; Jess’s back was to the wall, and Kyle sat across from her. Her eyes scanned the room, even as Kyle kept droning on and on.

That’s when Ian walked into the bar. Jess’s breath caught for a moment, and her heart started to beat a bit faster, and she felt her pussy moisten just a bit. Kyle, unsurprisingly, didn’t seem to notice her reaction. Ian went right to the bar, where he flagged down the bartender and placed an order before turning around. He caught Jess’s eye, and stared her down, eyes smoldering.

The bartender tapped Ian on the shoulder, letting him know his drinks had arrived—a bottle of red wine, along with two glasses. He held them up to Jess and gestured toward the private room in the back before walking out in the same direction.

Jess watched Ian go, appreciatively, enjoying the sight of his muscular legs and ass in his jeans as he walked out. Once he had gone, she turned her attention back to her boyfriend. He was still talking. Jess interrupted him. “Sorry, honey—I need to go to the little girls’ room.” She got up and excused herself, so she could follow Ian to the back room.

The door to the private room was open a crack, and Jess tentatively opened it a bit further. Ian was there, alone, steadily working the cork out of the wine bottle. It came free with a pop as she entered. Jess started to ask him what he was doing at the bar, but Ian shushed her with a finger on her lips before she got through the first word. He poured each of them a glass of wine and handed Jess hers. They clinked the glasses together and took a sip. Then he did something a bit odd—Ian took the still mostly-full glass from Jess and set them both back down on the table.

Jess raised one eyebrow, questioning him. He just smirked and motioned for Jess to turn around. When she did, he knelt behind her and ran his hands up her legs, flipping up her skirt and palming her ass cheeks. Under her skirt, Jess had worn a red thong; Ian leaned in and pulled it aside with his teeth before burying his face in her cunny from behind, making Jess gasp in shock and plant her hands on the wall to steady herself.

Ian ate her out from behind, just for a few moments, until Jess’s pussy was drenched with her juices and his spit. The he stood, undoing the fly on his jeans as he did and releasing the beast hidden in his pants. He was hard and ready. Jess looked back at him over her shoulder as he positioned himself behind her, lightly tapping her cunt lips with the head of his massive prick. Jess gave him a small nod, and he slid inside her, hilting himself in her in one slow steady motion. Jess bit her lower lip, chewing on it to keep herself from moaning otele gelen escort as she pushed herself back on him.

Before long, Ian and Jess were fucking in earnest. They were both breathing hard, but otherwise they were silent. The only sounds were their breathing, the slap of Ian’s hips against Jess’s ass, and the white noise from the bar. Ian reached in front of Jess with one arm and grabbed one of her breasts, feeling the firm, round orb as it bounced under her top.

Jess’s hand slipped slightly, pulling aside the curtain covering the windows on the door to the private room. Through the window, she could see Kyle, facing the other way in the corner, fiddling with his phone. Her cunt clenched around Ian’s invading shaft as she watched her oblivious boyfriend while her bigger, better lover pounded away at her. Her breath quickened, and she let the curtain fall back into place as she brought her hand up to her mouth and started to bite her knuckles to stifle her ecstatic cries.

Ian let go of her breast and wrapped his hand around her throat, pulling her away from the door. His lips were close to her ear, when he spoke the first word he’d said to her all night. In her ear, he whispered: “Cum.”

And she did. With her hand around her neck and his rock-hard rod buried inside her, she came. Her cunt constricted around him, and her nectar dripped down his shaft and left a dark wet stain on his jeans. Her eyes fluttered and her cheeks flushed, and her mouth dropped open—but the only sound she made was a small squeal of delight.

Ian pumped into her a few more times before backing away, still unfulfilled. He moved over to the table and aimed his prick at Jess’s half-full wine glass. With a few quick pumps of his hand, he came, grunting quietly as his cock spurted again and again, spiking her wine with his thick, heavy cum. When he was done, the glass was visibly more full, and some of his cum had sunk down to the bottom and was visible as a pale discolored spot. He put his cock away and refilled his own glass as Jess straightened her clothes.

He handed her the glass he’d refilled with his own personal additive, but stopped her when she went to drink it, covering the top with his hand and shaking his head. He picked up the bottle and his glass and left the room, heading toward the table in the corner where Kyle still sat, snagging another wine glass from the bar as he went. Jess followed him, unsure what he was planning.

Kyle jumped a bit when Ian came up behind him and put the wine bottle down on the table. Jess got there a moment later. “Hey, roomie!” Ian said. “Saw that you were here with the little lady, thought I’d get you both a drink.” He winked at Jess. “Enjoy the wine, and you kids have a good night out.”

Kyle seemed skeptical, as if he expected a trap, but he accepted the empty glass hesitantly and let Ian fill it with the wine. “Uh, thanks, Ian, but we’re trying to make tonight an evening for us, you know?” he said.

Ian put down the bottle and held up his hands, palms forward. “Hey, I get it. I’m not sticking around. Just wanted to do something nice for you two.”

Jess spoke up then. “Thank you, Ian.” She took a sip of her wine, tasting the rich flavor of Ian’s potent sperm along with the flavors of the wine. “It’s delicious.”


The Week Away

Ian had been gone for a week.

Her lover had been gone for a week, and Jess was going mad. She had even tried to break one of Ian’s rules by fucking her boyfriend Kyle, but he wasn’t able to get hard. Jess was faintly disgusted; she hadn’t slept with Kyle in months, and one might have thought he’d be gagging for it. But he hadn’t been sleeping well since starting college, thanks to Ian (and lately, thanks to Jess). He’d put on weight and had started drinking a bit more, and on the night in question Kyle just couldn’t get things going. Instead, he went down on her, but he didn’t even do that well, and Jess wound up faking her orgasm before leaving, claiming that she had a headache.

After that unsatisfying evening, Jess went to a sex store and bought a dildo. The experience had been surreal; Jess had expected a filthy, seedy establishment filled with strange men giving her furtive glances. She had dressed down, and come into the shop with a big pair of sunglasses and her long hair tucked under a baseball cap (as best she could). But the store wasn’t like that at all; it was actually rather sterile, with clean white floors and harsh fluorescent lighting. Still, she got in and out as quickly as possible, paying in cash.

Her new dildo was about a foot long and as thick around as her wrist; she got the one that most resembled Ian’s horse-cock. Before meeting Ian, she had almost never masturbated, and when she got back to her room and took the dildo from the package she found herself staring at it, unsure how to proceed.

Obviously, she pendik escort had the basics down, but she had never used a sex toy before, and she felt odd doing anything without Ian. That’s when she had a devilishly clever idea. She tucked the dildo (“Little Ian,” as she thought of it) into her backpack and set off for the dorm that Ian shared with her boyfriend.

Kyle had an evening class and wasn’t around, so she let herself into his room with the key he had given her. She breezed through to the bathroom he shared with Ian—although it took a moment to force open the door to the bathroom; it had gotten knocked loose in its frame after Ian had fucked Jess hard up against it one morning. From there, she let herself into Ian’s room, and turned on his laptop. After a few minutes of clicking around, she found his webcam and set it to record, turning t to face his bed.

She backed up, putting herself in frame, and lay down on Ian’s bed (it was new; they had broken his old bed on their first night together). She stretched like a cat, her canary yellow tank top rising up to reveal her flat midriff, and looked at the camera. There was a smile on her face as she said, “Hey baby. I’ve been missing you so bad, and I wanted to let you know what I’ve been doing while you’ve been gone.”

She reached down, off the bed, and her hand came up holding the massive dildo. “This is Little Ian. I got him to keep me company, but it just wasn’t the same.” She held it by the base and stroked it idly with her other hand. “Little Ian can fill me up, but he can’t rip off my top and suck my nipples,”—two quick tweaks made them stand out under her shirt—”or pull my wet little panties aside and eat me out, or pin me to the bed and fuck me senseless.”

Jess sat up and spread her legs. She was still wearing a pair of yoga pants that matched her top, and she let the dildo rest against their crotch. “But he’ll have to do.” She picked up Little Ian and spit on it, her hands working her spit all across its length. Then she slid it into her mouth, recoiling a bit at the taste of the plastic as it forced her jaws apart. She made appreciative noises as she gave the dildo a messy simulated blowjob, her spit coating its surface.

Once it was thoroughly coated and slick and shiny, she pulled it free of her mouth. “Shame that this isn’t you, baby—you taste better, and at the end I get a creamy treat!” She set it down and wriggled free of her tight pants, taking her panties with them. She spread her legs again and tapped the dildo against her tight slit. “You know, before I met you and you stretched me out, I don’t think I could have gotten Little Ian in here,” she said. “But now I need your thick meat inside me. I need it every day, baby, and when you get back I am going to drag you into bed and force you to fuck me until that horse cock hanging between your legs is limp and those bull balls are completely empty. I want to have your cum in me and on me. If I can still walk, then that means you haven’t fucked me enough.”

She pushed on the dildo, parting her lips, and hitched her hips forward so the camera could get a better angle as it entered her. With both hands on the base, she pushed it inside, biting her lip as she did, tears glimmering in the corners of her blue eyes as she once again felt that overstuffed sensation she had come to crave since Ian first took her and made her his.

As it entered her, she kept up her litany of dirty talk. “Do you like seeing me like this, baby? I’m so desperate for you that I bought this toy because it was almost as big as your cock, and I came to your room so I could feel closer to you.” She was breathing hard now, her tits rising and falling under the tight yellow top. “But it’s not as good as you baby, it only makes me need you more. I’m addicted to your cock. I love your cock and I need it to fuck me over and over.”

Jess started to work Little Ian in and out of her cunt, furiously pounding herself with it. “When you get back I want you to do this to me, Ian. I want you to throw me onto your bed and make me spread my legs for you, then I want you to take me hard and fast.” She held onto the dildo with one hand and started to roughly grope and squeeze her own tits through her shirt. “You won’t even have to call me. When you watch this video, just send me a text and I’ll drop whatever I’m doing and come over so we can fuck.”

Her hips were rocking now, and the wet sounds of the dildo sliding in and out of her slick cunny formed a counterpoint to her gasps and moan. “I need to confess something, baby. I was going to let Kyle stick it in me, that’s how horny I am. I’m sorry, I know you don’t want me to fuck him—when you get back you’ll have to punish me for being so naughty.” A flush crept up from her chest to her neck as her orgasm approached.

She adjusted her grip on the dildo, so that it pressed against the special sensitive spot inside her, rus escort and redoubled her efforts. Within a few moments, she squealed and came, her body writhing on Ian’s bed, her cunt clenching around the thick plastic rod currently filling her. Her back arched, coming off the bed entirely, and she lost her grip on the dildo, her hand fluttering in the air by her side. But her cunt was so tight around the toy that it stayed in place, held inside her by the vise-like grip of her pussy.

When she was done, Jess propped herself up on her elbows and looked right at the camera, the dildo still buried deep inside her. “Mmmm, I needed that. But I need you more. Come back soon.” She gave the camera another grin, then stopped recording. A few clicks, and the video was on its way to Ian’s e-mail.

Her phone buzzed less than ten minutes later. There was a text from Ian: “2 hrs. Hands and knees, blindfold, facing away from the door. Be ready.” Jess’s heart leaped with joy.


In Training

Jess blushed, paid the cashier, and scurried out of the store, her face to the floor. A week ago, Ian had asked her about Kyle’s sexual fantasies. She had no idea—the two of them never talked about his fantasies, and Kyle still thought Jess was prim and relatively uninterested in sex. The truth was that she just wasn’t interested in sex with him. Sex with Ian, on the other hand, was practically what she lived for. So when Ian asked about Kyle’s fantasies, Jess was confused and didn’t have a good answer for him.

But he had insisted she find out. So Jess spent a bit more time with Kyle, teasing him, asking him innuendo-laden questions, and the like. Kyle seemed a bit surprised by her newfound interest in sex, and even got so bold as to suggest that they sleep together—something he rarely did, believing that Jess didn’t like it. The last time they had tried, it hadn’t gone well for Kyle; he was never the best lover, but sleeplessness, stress, and his weight gains had given him erectile issues. No matter how he tried, he couldn’t get hard, even with Jess stripped bare and bent over in front of him, wiggling her ass in his face, her dripping cunt only inches from his mouth.

This time, he managed to get it up. But he didn’t even have time to disrobe before Jess came up behind him, her tits pressing against his back, and whispered in his ear, “Maybe you want to fuck my ass?” That was enough for him, and his cock spurted its tiny load into his underwear. Jess pretended it was fine, and asked him if that was something he really wanted. Kyle, somewhat bashfully, told her it was one of his favorite fantasies, but he had never brought it up before out of respect for Jess.

Jess told him it was sweet that he cared so much about her and left him to get cleaned up. She reported to Ian at the first opportunity. He directed her to get some lube and some toys, to prepare herself for him—he was going to live out Kyle’s fantasy. Jess nervously assented.

After spending some time researching on the internet, she bought a set of butt plugs from a sex shop in the city. It was the same shop where she had purchased her dildo, Little Ian, and more recently where she’d purchased her first vibrator as well—a little bullet vibe that came highly recommended from her girlfriends, all of whom were surprised to hear the seemingly prudish Jess ask about sex toys.

It took her a day to work up the nerve to open the package and take out the silver toys inside. There were four of them; the smallest was no longer than her middle finger and as thick as her thumb at the widest point, and the largest was perhaps as thick as three fingers and about seven inches long. Each plug had a glittering rhinestone on its flared base; they sparkled and caught the light as she examined the toys.

It was another day before she could bring herself to experiment with them. She tried the smallest toy first, her heart in her throat as she popped it in past the tight ring of muscle. Once it was in place, she was able to relax; it gave her a somewhat full feeling, and she could feel it shift slightly as she turned and moved. She walked over to the floor-length mirror hanging from her door, swaying her hips a bit more than she usually did as she got accustomed to the odd sensations.

Jess admired herself in the mirror. Her long brunette hair was up, a pair of pencils holding it in place, and she had on a tight white babydoll t-shirt that clung tightly to her curves; she wasn’t wearing a bra, and her nipples could be seen proudly erect through the thin fabric of the shirt. She was naked from the waist down, her freshly waxed pussy bare and (she was a bit surprised to note) glistening with wetness. Jess turned, arching her back just a bit, thrusting out her ass. The jeweled base of the plug glimmered in the mirror, nestled between the two globes of her luscious ass.

“Yeah, I guess that is pretty hot,” she said to herself. The thought of giving herself to Ian in this way, and of spending days preparing to do so, had gotten her worked up. She dug out her phone, not bothering to put on pants, and sent Ian a quick text: “Come over. Door is open.” She unlocked her door with a click and went over to her bed, pulling Little Ian and her silver bullet from their resting place in a jewelry box in her nightstand.

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