Jackin' Jill Ch. 01

Author's note: This story is finished, and the plan is for chapters to post on every Tuesday and Friday until the story is complete, though that's variable because of Lit's queue.

****

Rodney stood at the top of the stairs, listening for hints that anyone was still awake in the house. After a few minutes, he was sure that his parents and sister were all out for the count. He closed the basement door, locked it, and crept down the stairs, his heart beating fast and his cock already throbbing.

Wasting no time, he headed to his computer and navigated to the cam site, praying that he hadn't missed her. A wide smile spread across his face when he saw Jill's headshot near the top of the listing of cam models. Not only was she still on, she was obviously having a good night. A model's position in the list was determined by the number of private minutes she did while on cam, and only two other models were ahead of her.

Rodney clicked into her room and let out a quiet groan when her image appeared on screen. Jill was wearing his favorite outfit — a pink bra and panties with stockings and garters to match. Her room was packed as usual. She was hardly the youngest model on the site at thirty-six, but she actually chatted with the people in her room and gave a few peeks in free chat. That was what brought him to her room night after night, and he wasn't the only one.

His smile spread wider and his erection throbbed when her voice came through his headphones. "Rod! It's about time."

"Hey Jill. You look awesome," he typed.

She flipped her short blonde locks and affected a girlish pose. "Thank you. I was just about to go off cam for the night. I'm glad I didn't miss you."

Crestfallen, Rodney typed, "Awww. How much longer?"

"About five more minutes, unless somebody goes private."

The temptation was tremendous. With his recent raise, he could almost afford to buy a private show, having her all to himself for a few minutes, and finally seeing all of her body live. It would mean bringing sandwiches to eat between classes at college and on lunch break at work for quite a while, but he was beginning to think that it would be worth it.

The chat moved fast as Rodney agonized over his decision. Jill was posing for the camera, displaying her assets to good advantage in hopes of enticing a final private show before signing off for the evening.

Shw ur puss. Get ur tits out. Dog style. The beggars in the room typed fast and furious, hoping for a peek.

"They're 36D," Rodney typed to answer one of the constant questions that came up in chat, even though that very thing was listed in her bio on the left side of the screen. "Yes, they're real. Let her do her thing. Begging doesn't help," he continued.

"Listen to Rod. He knows what he's talking about," Jill said, and then winked at the camera before cupping her breasts and jiggling them.

On the verge of clicking the private show button more than once, Rodney's nerve finally failed him. He was just too nervous to go through with it. His raging erection had even softened. He let out a sigh when Jill sat back down and grabbed the keyboard, knowing what was coming.

"Last chance," Jill said after typing the same thing for those who weren't streaming the sound, "If you want to go private, better do it quick. I'm going to be off for a week."

The begging continued, but nobody bought a private show.

"Okay, I'm going to go," Jill said, and typed. "This is for Rod, Bird, and ChiDog, because they know how to behave."

Rodney groaned as Jill tugged one of her breasts free from her bra and lifted it. She teased the dark pink nipple with her tongue for a second, then let the heavy globe drop back down. After a finger-waggling wave, she closed down the room.

A click on his favorites bar took Rodney from the chat site to her private website, because she usually went there and posted on her forum after going off cam. Much to his delight, he discovered that she'd posted some new pictures.

The shots were shower pics — something that he'd requested. The first few were silhouettes through a shower curtain in provocative poses. The last was of her peeking out from behind the curtain, her hair damp and beads of water adorning the leg she revealed. Her nipples were visible where they were pressed against the frosted curtain.

Rodney knew that he had his masturbation fuel for the night, and there was more to come. He was one of the few that Jill had given access to the private part of her site — at least one of the few who had never bought a private show. He clicked the link to the password-protected section, throbbing in anticipation.

The second set of pictures was all with the shower curtain open. At first, her assets were completely covered in thick lather, but following pictures showed her stepping into the cascade of water to wash the bubbles away. The last few were of her shaving her legs and nether lips with water flowing down her gorgeous curves.

Rodney was hard as a rock, and could feel a cold spot where he'd leaked pre-cum. It was then that he noticed something she'd added to the bottom of the page.

You can all thank Rod for these. They were his idea.

Grinning so wide that his cheeks hurt, Rodney opened a new window to go to the forum. A private message notification popped up as soon as the page loaded. It was from another regular chatter he was friends with, DaWatcher.

The message read, "Good suggestion on those pics. DAMN! Hey, I'm going to be down in Galveston next week, starting tomorrow. Want to meet me somewhere?"

He and Watch always played off each other's jokes, and had quite a few similar, geeky interests. The chance to hang out with someone he actually connected with — and could talk to about Jill — was too good to pass up.

After a reply suggesting a restaurant where his damn Yankee friend could get some genuine Tex-Mex, the refreshed window showed yet another private message. This one was from Jill.

"Everybody loves the shower pics. I had fun with that shoot. Missed you tonight. Were you out on a date with Denise?"

Rodney was beginning to wonder if telling her about Denise was a good idea. She teased him constantly about leaving her for another woman, but also encouraged him to go for it daily. Denise was in a couple of his courses, and they often chatted in the time between the two. She was the first girl in a long time that he'd felt he might have a chance with, but he still hadn't worked up the courage to ask her out.

He was almost as afraid of her saying yes as no, because he hadn't had a girlfriend since the fifth grade. Needless to say, he was still a virgin.

He typed back that he still hadn't asked her out, and then opened another message from Watch which said that the time and place were both fine with him. As soon as he replied that he'd see him there, he read the final message from Jill.

"Ask her out, silly. I'm going to bed. Night night. Think about me? Mmmm!"

Rodney shivered, imagining her thinking about him — the insider code for masturbation. With her shower pics fresh in his mind, he knew that he would certainly be thinking about her.

Rock hard, he turned off the computer and went to do exactly that.

****

Rodney spotted Watch easily when a friend dropped him off the next day outside the Tex-Mex place, having exchanged pictures quite some time ago. He was in his thirties, but love of Star Trek knew no generations.

"Rod," Watch exclaimed upon spotting him, and held out a hand.

He shook it, and said, "Welcome to Texas, Watch. Looks like there are some tables on the balcony."

"Works for me. I'm starving."

The pair ordered and found their seats on the balcony, which offered a fine view of the scenery — natural, architectural, and human. A pair of attractive women with large, well-displayed breasts were center stage below as the two friends sat down. Watch blew out a quiet whistle as he admired the sight.

"Everything's bigger in Texas."

Watch laughed. "Looks like it. Hey, that reminds me. You missed this jerk in chat last night. Came in with the name Texas Longhorn."

That began a long conversation about chat, kept reasonably quiet to avoid alerting the people seated nearby to what they were actually talking about. The pair often broke out into gut-busting laughter, reminiscing about how they had chased off annoying people from the chat with one-two punches of biting insults. The amused encouragement of the other people in the chatroom — and more importantly, Jill — usually did the trick. Having an attractive, half-naked woman laugh at you when you're not trying to be funny was apparently a bit of an ego killer.

The food was long gone and Rodney still wiping tears out of his eyes from laughing at the latest tale Watch had told when a tone sounded.

Watch pulled out his cell and checked the text message, still laughing as well. After tapping a reply, he put the phone away and looked around. "Think people are starting to get annoyed at us. I've got some beers back at the hotel room."

Still below drinking age, and hardly part of social circles where he was regularly invited to parties, Rod jumped at the chance. "Hell yeah."

"I got the tip." Watch pulled out a few bills for the gratuity, shaking his head when his cell beeped at him again. When he finished replying, he stood and said, "Let's go get a good buzz on. I walked, because this place isn't all that far away."

Glancing over the balcony at the scantily clad women moving about, Rod said, "And you can't beat the scenery."

"No shit."

Quite a few of those attractive girls glanced their way on the walk. Watch was attractive, muscular, and exuded an air of confidence. Walking at his side — skinny and shy — Rod had to wonder why his friend hung out in nude chat rooms. It wasn't as if he likely needed a substitute for real female company. It did feel good to have women looking in his direction, though — even if it was directed at Watch.

He was staying at one of the better hotels in town, and they continued to chat along the way, moving into discussions of Jill's various outfits. When they arrived at his room, he scanned his keycard and pushed the door open.

Rod's mouth dropped open and his eyes widened when Jill said, "Surprise!"

He was still in a state of shock when she wrapped her arms around him and pressed her lips to his. Despite the surprise, it only took a millisecond for him to melt into the kiss, which turned his legs to water.

"Mmm. Sweet kisses," she said with her lips still only inches away from his. "Come on in."

Watch was chuckling as he followed them in the room. Wondering if he was dreaming — and praying he wouldn't wake up — he turned to his friend.

"Sorry. She made me do it."

"I wanted to surprise you," Jill explained.

Though he regretted the stupid question as soon as it passed his lips, Rod asked, "Jill?"

"Of course, silly. Well, it's actually Lisa, but stick with Jill. Hearing my real name is weird, and that way you won't slip up in chat."

If anything, she was more stunning in person than on cam. Her luscious curves in a short skirt and tight, spaghetti-string top were mouth watering. The smile he knew so well brought one to his own lips as she led him over to sit on the bed.

Bending down into the mini-fridge, Watch said, "The beers are real, though," he passed one to Rodney, and then opened one for himself.

Jill sat down close to him. "I wanted to meet you, since we were going to be here anyway. Had to play it safe and have Jeff make sure you weren't a serial killer or something, though."

Thinking that a little liquid courage wasn't a bad idea, Rod opened his beer and took a long swig.

She put her hand on his knee and laughed. "Relax. I'm not going to bite — unless you want me to." She twitched her eyebrows.

"It just feels like I'm dreaming," Rod finally managed to say.

"I know. Me too," she agreed. "I thought Jeff... Whoops — Watch — was never going to bring you over."

"I was having too much fun," Watch said as he sat down on the opposite bed and took a pull of his beer.

"May as well tell you and get it out of the way," Jill began. "Watch and I have been best friends since like the third grade. We lived next door to each other. We never really dated, but we hung out and started experimenting when we got to that age. We got each other's virginity, and we've pretty much been together ever since."

"So, you're married?"

She laughed. "God, no! He's too much of a whore. We're fuck buddies, but we're not exclusive or anything. He's my cameraman, and plays stunt cock when I want some facial pictures or something. He's the one in the first couple of Jackin' Jill videos."

Rod had always been fond of those videos, where Jill did a sexy striptease, and then gave a man a handjob, jerking him off onto her tits. They were all shot point-of-view, which let him put himself in the guy's place.

"The rest of them are nice guys from chat that I've met in person. Bird was the guy in the last one." While she talked, her hand slid up from his knee to his thigh.

Watch broke out into a laugh as Rodney's eyes widened again. "I think it's starting to sink in."

Jill's fingers glided over his crotch and she asked in a low, sultry voice that made him break out into goose bumps, "Want to be in the next one?"

"Seriously?" Rod asked, his voice cracking and making the blush already rising in his cheeks even darker.

"Mmm hmm," she moaned, her fingers pressing tighter against his crotch. "You always make me smile in chat, and you get me so hot when you start teasing. I've been thinking about it constantly ever since we knew we were coming to Galveston."

"We damn near missed our plane because she was getting herself off one more time before we left," Watch interrupted, and laughed.

Jill stuck her tongue out at him.

Though his heart was pounding and his cock rising fast from the thought, Rodney couldn't help looking over at Watch. No matter how incredible the notion of Jill jacking him off was, the thought of another guy — even Watch — over his shoulder with a camera was a bit much.

Watch waved a hand in front of him. "All I'll be doing is setting up the lights and the camera. Then I'm out."

"It would just be you and me," Jill said, squeezing his erection and letting out a moan that mingled both surprise and pleasure. "Pretty please? I want to make you come. I want to see it. I want to feel it squirting all over me — for reals."

A groan escaping him from the feeling of her hand caressing him and the sexy serenade of her voice, he nodded his head.

Jill gave him one final squeeze, and let out a sharp growl. "I'm going to go get changed."

Rodney watched her walk to the bathroom in a near daze. She looked over her shoulder, winked, and gave her ass a slap before disappearing around the corner. He tilted his head back and drained the last of the beer in one long guzzle.

Watch laughed and walked toward a large suitcase. "Plenty of beer in the fridge. Bird drank a six-pack before she finished getting dressed."

Nerves on edge like nothing he'd ever experienced before, Rodney leaned down and into the fridge for another beer. He finished that one and another — sitting in awkward silence — while Jill was in the bathroom and Watch set up the lights on tripods from the suitcase.

In the process of testing the camera and the hookup to the laptop so she could see the camera to control it with a remote, Watch finally said, "Relax, man," and chuckled. "You look like you're about to throw up."

"Easy for you to say."

"Yeah. Guess so. Everything's ready to roll. I'm out." He pointed and said, "Have fun," before leaving the room.

The door outside hadn't even completely closed when Jill stepped out of the bathroom. She was wearing his favorite outfit again, but had added elbow length satin gloves to the ensemble.

"Like it?" she asked while reaching down to trace her middle finger over her panties.

A silly grin spread across his face as he nodded.

"Mmm. I can't wait any longer. Sit down in the chair."

It wasn't exactly rocket science to figure out which chair she was talking about. Lights were carefully aimed to illuminate it, and the camera was positioned just to the right and behind it. With his eyes locked on her as she negotiated the cables and equipment, he sat down in the chair.

She raised a satin-clad finger to her lips, winked, and then picked up the remote, starting the camera.

Jill waved and said, "Hey, everybody. It's Jackin' Jill time." She reached up and cupped her breasts for the camera and groaned. "I've been waiting for this for days. Playing with myself. Making myself come."

Rodney stared as she moaned and slid her hands down her body to press her fingers between her legs. He'd gone soft from nerves, but that was changing in a hurry.

"I've got a brand new cock to play with, and the thought of it is making me so wet." She sat back in the windowsill behind her, bending one knee until it rested on the sill as well.

Rodney tugged at his jeans, trying to make room for his hardening cock. Out of the corner of his eye, he could see that she was zooming the camera with the remote while she pulled her panties aside. He glanced over at the close-up view just in time to see her part her nether lips, showing the wetness within.

"See?" She tugged her panties back in place and let her foot slip to the floor after zooming the camera back out. "I usually get naked, but I know he loves this outfit. So, I'm going to leave it on." A coquettish grin preceded her adding, "Mostly."

Jill stood up into a slow, sinuous dance, running her hands all over her body. "I know he wants to see my titties, and I know you all do too. I love showing them off, thinking about how hard they make you." She reached up and pulled down first one, and then the other strap of her lacy pink bra.

"I know most of you have your cocks out right now." She rolled her eyes up and moaned. "I know you're going to be stroking them. Coming for me. It makes me so hot."

Throbbing so hard that he thought he might bust straight through the zipper of his pants, Rodney breathed heavily, hypnotized by her words and her sexy body.

Her hands moved behind her back, ever so slowly, to meet in the middle. Her breasts jiggled as she unhooked the clasp, and she licked her lips. Looking straight into Rodney's eyes, she slipped her right arm out of the bra. Then, she crossed her arm over her breasts, and managed to wriggle her left arm free without dropping the bra.

Moving her hands to the overflowing pink cups, she held them in front, and then let the bra tumble to the floor. A second later, she snapped her hands out in a ta-da gesture and laughed as she revealed her breasts in all their glory.

"Look how hard my nipples are," she said while reaching up to tease one with her finger. "Ooo! Mmm, these gloves were a good idea." She stroked her breasts with both hands, arching her back to thrust them toward the camera. "A very good idea."

Rodney could feel the chilly spot in his underwear from a drop of pre-cum having seeped from the swollen head of his cock. His pants weren't even unbuttoned yet, and he already felt as if he weregoing to explode.

"I know I should tease some more, but I can't wait." Jill walked toward him, her heavy breasts swinging and jiggling with every hip-swaying step. She aimed the remote at the camera, panning and zooming as necessary until she was in frame, on her knees in front of his chair.

She stroked her fingers up his legs, looking up into his eyes. "It's just like Christmas. I can't wait to open my present."