Jackin' Jill - Cover

Jackin' Jill

Copyright© 2015 by Les Lumens

Chapter 3

Erotic Sex Story: Chapter 3 - Rodney is not what you would call a ladies' man. Nearly through his first year of college, he's still a virgin. His one sexual outlet and primary sense of self-worth comes from a nude chat room, where the regular chatters and his favorite camgirl are always overjoyed to see him. Outside the box, he's a nobody. Inside, he's a comedian, tech guru, and White Knight. Then, out of the blue, his two worlds collide. (Codes will be added as story progresses)

Caution: This Erotic Sex Story contains strong sexual content, including Ma/Fa   Consensual   BiSexual   Heterosexual   First   Oral Sex   Anal Sex   Masturbation   Sex Toys   Exhibitionism   Voyeurism   Double Penetration   Tit-Fucking   Public Sex  

Rodney started awake, shaking his head and blinking against the light streaming in the window. After a few seconds, the sleep fog began to lift from his head, and he realized that the light was out of place. He wasn't in his basement room at home.

Memories returned as his eyes adjusted, and a smile spread across his face.

Jill completed a long, broad-tongued lap of his erection. When she saw that he was awake and watching, she stopped teasing and took him in her mouth. After a few sucks, she pulled his wrist, guiding it to the back of her head. Rodney groaned, pulling down ever so slightly each time she swallowed his cock.

Her hot mouth tantalized him for around a minute before she let the tip slip free, looked up into his eyes and said, "Good morning."

"Uh huh," he responded - his saliva-slick member bouncing up to tap her in the chin. He shifted on the bed, wincing a little from the pressure in his bladder.

"Need to pee?"

Rodney nodded.

She gave the head of his cock a final kiss and said, "Go ahead."

By the time he returned from the bathroom, she had put on a pair of shorts and a t-shirt. It was disappointing - but only a little. She was every bit as sexy clothed as she was naked.

"Thought we should probably slow down a little." She picked up his underwear and tossed them to him. "You're going to need enough energy to go get some clean clothes."

While he pulled on his clothes, she typed away on the computer. He could see that she was on her website, posting on the forum. Once dressed, he said, "So, uhm..."

"What now?" She chuckled. "Like I said, you need to go get some clean clothes. First, I want to see this Denise. Do you have any pictures of her or anything?"

"Her Facebook, I guess."

"So, she added you, then? That's a good first step. Show me."

He navigated to the site, and then to her profile. She'd just posted a status about a movie that had opened, saying she planned to go see it. Jill leaned in and gasped, so he looked at her and asked, "What is it?"

"Just that she's delicious. Click on the pictures, silly. I want to see more."

Rodney cycled through the pictures, growing hard as Jill leaned over his shoulder, moaning in approval with each new one. She gestured for him to return to the main profile page after the last picture, then pointed at the screen to her relationship status - single.

"You should do something about that."

He blushed, shifting a little on the bed. "It's just ... I'm too nervous."

"Why?"

"Because I don't know what I'm doing. I've never been on a date or anything."

"You'd never had sex until yesterday, either. You got over that pretty quickly," she said in a sultry whisper right into his ear, then kissed his neck.

"That's different."

"No, it isn't. Okay, do you have her number?"

"Uh, yeah. We were grouped together for a lab once."

"So, start dialing."

"I..." His stomach knotted up in fear.

"Okay, you need to relax, and I know just how to do that." She pulled her shirt off, letting her breasts free, and then leaned in to unbutton his jeans. "Pants off."

Jill lay back on the bed, caressing her breasts and licking her lips. Rodney put the laptop down and quickly removed the pants he'd put on only a few minutes before. As soon as he kicked them off, she sat up and used the convenient handle of his stiffening cock to pull him toward her. She then reclined again, still holding on, and pulled him to straddle her. Once he was atop her with his balls resting on her tummy, she squeezed her breasts together and nodded toward them, twitching her eyebrows.

He knee-walked forward, and she let the firm globes separate again. Once his erection settled between them, she squeezed her breasts together around him, forming a warm nest.

"Now fuck my titties and come for me. No holding back. Just do it, and explode for me."

Rodney rocked his hips, letting the firm globes caress him. His cock wasn't really sliding between them, but rather moving the skin over the core of his hardness. At the end of every stroke, the tip would still poke out from between her breasts, though. It was then that she took advantage of the opportunity to lick or suck on the swollen head.

"Feel good?" she asked between flicks of her tongue.

"Fuck yes," he responded, pumping faster.

The words coming rapidly, and in excited tones, she encouraged him, "That's it, baby. I want your cum. I want it all over me. Do it."

The bed creaked as he continued to build speed. She dragged over a second pillow, propping up her head and giving her better access to his tip when it peeked out. The increasing strength of his thrusts revealed more of his cock as his excitement mounted. Jill locked her lips around it when she could, sucking hard, and causing it to audibly pop from between her lips.

Rodney grunted, rising quickly to a peak. When his cockhead next popped out of her hot, wet mouth, he was there. "Ah, yeah. Gonna come."

"Give it to me!" she demanded, her voice warbling as he rode her body, fucking her tits hard.

One last pump set him off, and a hard jet of cream spattered against her chin, trailing up onto her face. He gasped, and the next spurt went directly up the bridge of her nose, into her hair, and onto the pillow beyond. His hips twitched beyond his control, and his still-trapped cock erupted in three more squirts, decorating her lips, cheeks, and closing one eye. The final pulses spotted her neck with his cream and pooled beneath his throbbing organ.

Jill released him from her breasts and he fell forward on his hands over her. She licked her lips, moaned, and cleared his cum from her eye so she could look up at him while sucking her fingers clean.

He only saw that afterwards, though. His eyes were tightly closed as he panted for breath. It was only when she gave his bottom a smack and then pushed on his hips that he opened his eyes to see her smiling up at him. With no small amount of effort, he lifted one knee, and then sat down heavily on the bed next to her.

"There, now. Aren't you a lot more relaxed?"

"Uh huh," he sighed, and then chuckled. She was still pulling the copious spatters of cum adorning her face to her lips, savoring every drop.

"Good." She sat up and picked up his phone from the nightstand. "Call Denise and ask her out."

"To where?"

"The movies. She's already planning to go. It's a nice, safe first date. You automatically have something to talk about, and you won't need to worry about tripping over your tongue while the movie is running."

While she talked, she did something on his phone. When she handed it to him, she'd already selected Denise from his contact list and hit send. His heart beating fast, he brought the phone to his ear just as she answered.

"Hi, Denise." Out of the corner of his eye, he saw Jill making a circling gesture with her hand. "I was wondering if you would want to go out to the movies?" A combination of panic and relief washed over him as the words came out.

"I was actually going to go tonight by myself," she answered. "But if it's your treat?"

Stunned by the sound of enthusiasm in her voice, he said, "Sure. My treat."

"Meet me at the library at seven?"

"The library at seven."

"I'll see you then."

"Yeah, okay. Bye, and see you then."

"Goodbye."

Rodney clicked the end button and stared at the phone for a moment, in complete disbelief.

"Now, was that so hard?" Jill asked.

A chuckle escaped him as the absurdity of what had just happened hit him. He'd asked a girl out for the first time while sitting with his cock out, next to a bare-breasted woman covered in his cum.

She gave him a pat on the bottom. "Get cleaned up and dressed. Then go home and get some clean clothes. Bring something to change into tomorrow, too. You have a date to get ready for, and I have videos to edit and upload."

"I have to work tomorrow."

"Watch can drop you off at work and pick you up. He'll be back in a little while. He called before you woke up. I guess Gina wore him out." She laughed, then bit her lower lip and fixed him with bedroom eyes.

"There's still some firsts I haven't claimed yet."


Rod looked at the clock and swallowed hard.

"You okay, man?" Watch asked.

"I think I'm going to throw up."

"Relax, man. Okay, number one. You asked her out, and she said yes. Number two. You said you wanted to see the same movie she did. Number three. You're taking a lot of the same classes. That's common interest, buddy. That means things to talk about."

"I don't know."

"You were nervous as fuck the first time you came in Jill's room too. I was there, remember? You got over that quickly enough."

"That's online."

"Yesterday wasn't online," Watch countered.

"That's..." He blushed, unable to find an answer.

"That's a woman. One who likes you despite sharing fewer common interests, I might add. You've got a sense of humor, and you know how to pay a girl a compliment without being creepy. Use it. You'll just have to say it instead of typing it."

Talking about Jill made him wish she was there. When he was around her, he felt so much more confident, and he could use that right now. Unfortunately, she was at Gina's on an impromptu live cam session.

"No more time to worry about it," Watch said as he grabbed his keys. "I'll drop you off by the library."

Rod spent the whole drive trying to think of things to say to Denise when the time arrived. Nothing that popped into his head sounded right. He felt dizzy as he climbed out of the car, and quite nearly got right back in.

Watch put the rental car in gear and said, "Relax, and have fun. See you later."

With that, Rod was on his own.

Barely around the corner, he saw her waiting. A quick glance at his cell told him that he wasn't late, which prompted a sigh of relief. She was just a little early, the same as him. She looked incredible - dressed casually in a pair of jeans and a blouse. Her hair was longer and a darker blonde than Jill's, and she had smaller boobs, but they were still plenty eye-catching. As he walked toward her, their eyes met, and she flashed a brilliant smile.

"Hi. Ready to go?" Denise asked as he walked up to her.

"Yeah," he answered, mesmerized by her smile.

"What?" she asked after a few seconds.

Realizing he was staring at her and wearing a silly grin so wide it made his cheeks ache, he said, "Sorry, you look great. You did something different with your hair."

"You like it?" She turned her head and smoothed her fingers down her blonde locks.

"Yeah, it looks great."

"Thank you. Well, let's go so we can get decent seats." She started walking, and he fell into step beside her. "I've been waiting for this ever since I saw the previews."

"Me too. Looks like it's going to be good."

Her voice carried hints of amusement when she said, "So, you skipped out of classes Friday."

"Yeah. An online friend I've never met in person was in town. Figured I could miss a day."

"Everybody was shocked. You never miss class. I can give you copies of the notes from the classes we share, but you didn't really miss much."

"Thanks."

"That's cool that you met somebody from online. There are a few I want to meet, but it's kind of scary. I think I live online, sometimes."

"Me too. Whenever I see a form with an address line, I want to write my IP address."

She laughed and Rod chuckled. All of the sudden, he noticed that the butterflies in his stomach had stopped fluttering. Maybe - just maybe - Jill and Watch had been right after all.


The conversation during the walk back to the library was easy, as it mostly centered on the movie. Rod was completely at ease until they stopped. He was beginning to panic, trying to think of something to say when Denise jumped in.

"This was fun."

"Yeah, me too." He prayed that didn't sound as lame to her as it did to him.

"We'll have to do it again some time. Call me?"

His heart skipped a beat. "Sure."

"Well, I'll see you in class, then."

"See you Monday."

She gave a wave and turned to walk back to her dorm. It was all he could do not to stare at her tight little butt swaying hypnotically. Somehow, he forced himself to turn around, and saw Watch leaning against his rental car down the street.

"That looked like it went well," Watch said as Rodney walked over. "She's a hot one."

"Yeah."

"Yeah, she's hot, or yeah, that went well?"

"Both, I guess."

Watch chuckled. "Told you to just relax. Let's get back. Jill isn't going to relax until you tell her how things went."

The prediction proved accurate, and Jill wasn't satisfied until he had spilled about every moment he could remember. She was wearing a short blue dress, black stockings, and heels, and looked absolutely stunning to him. It was almost odd chatting with her while she had clothes on, after so much time spent with her naked - exactly the opposite of how he'd felt not so long ago. With the details of his date recounted in minute detail, it was her turn to show how her day had gone, because she had video.

At first, there was a lot of footage of the two of them sitting in lingerie on the bed, talking and typing. A few short - and hot - private shows interrupted, but much of the beginning was chat. Jill explained what the chatters were saying that prompted the reactions on the screen, resulting in Rod and Watch riffing off the comments and each other, just as they did in chat.

The three sat laughing and making fun of the sillier people who were ever-present in chat. Rodney had three beers, and had a strong buzz going by the time the percentage of private shows to public chat reversed. Jill also started a sultry commentary about the sex on the screen, which caused a quite natural reaction in Rodney.

He stiffened a little the first time she squeezed his cock, because it was weird with Watch sitting just on the other side of her on the bed. After a few more squeezes and teases, his sex drive dulled the embarrassment - though not completely. Near the end of one of the nearly constant private shows where Gina was straddling Jill's face and coming from a combination of the blonde's tongue and a vibrator, Jill leaned over and whispered into Rodney's ear.

"Mmm ... Imagine if that was Denise I was licking, and that vibrator was you fucking her hard and making her come."

He couldn't help but shudder.

She let out a purring moan at his reaction and then said, "By the way, have you been on my site today?"

"No. Been too busy."

"Your Jackin' Jill video is up. Watch rendered and uploaded it at Gina's. Everybody's loving it. You just took the record for most comments in a day."

"Really?"

"Mmm hmm. The other one is uploaded, but I haven't linked it yet. Gina didn't have the software to blur out your face." She started running a finger up and down his chest. "Of course, we could just go ahead and put it online."

There was no doubt from her suggestive tone that she was asking for permission. "I don't know..."

"Wouldn't you love for everyone to know that you fucked me? Ate my pussy and stuffed that gorgeous cock deep inside me and filled me full of cum? Let them see you, baby."

Her fingers reached his crotch again and wormed beneath the waistband of his pants to tickle the head of his cock through his underwear. Rod groaned, "I..."

She leaned in and whispered directly in his ear, "Pretty please."

In the back of his head, in a split second, he rationalized that the video was going to be on the private part of the site anyway. Only people who had bought private shows would be able to see it. It wasn't likely that anyone he knew was going to see it.

"Okay."

Watch laughed. "I'll be damned. You win. I didn't think there was a way in hell you'd talk him into it."

"I'm good," she said rather haughtily, then leaned back in to seductively whisper in Rod's ear, "Aren't I?"

"Yep," he admitted, his face burning as he realized what he'd agreed to.

"This ought to drum up some repeat business," Watch said as he walked over to the computer.

"I can't believe I just said that," Rod mumbled.

"Mmm ... I bet you end up loving it. Showing off is what really turns me on. I'm not kidding when I say that on cam." She bit her lower lip and hit him with her bedroom eyes. "As a matter of fact..."

"Oh boy," Watch said as he clicked away in the process of linking the video up on Jill's website.

"Grab that camera, and let's go out on the balcony," Jill said.

Rod's eyes widened. "Are you serious?"

"Mmm hmm. I love getting naked in public and knowing that people might be watching. You get to work the camera and get nice and horny."

"Video's officially on the site. I'll keep an eye out for cops," Watch said, and then laughed. Because Rodney hadn't yet picked up the camera, he did, and handed it off to his chat partner in crime.

More than a little nervous, Rodney took the camera and followed Jill out onto the balcony. She sat down on the table there with her feet in a chair. If she had sat down in the chair, she would have been at least partially hidden by the slatted railing. On the table, she would be visible to anyone in the parking lot and beyond.

"Just turn it on and point at whatever you want." She gave a little wink. "I'll tell you if I want you to do something specific."

"Okay," Rod said as he turned on the camera, adjusted the focus to show her completely, and started recording.

Jill waved and said, "Hi, everybody. I just had an urge to come outside and enjoy the night air while I'm on vacation." She leaned back on her hands, thrusting her breasts up into the air and moaned. When she sat back up, she said, "Show everybody the view."

Rodney turned, and then scanned the camera left to right to show the ocean view. It wasn't right next to the hotel, but they were close enough to smell the ocean. He then aimed the camera back at Jill.

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