Jackin' Jill
Copyright© 2015 by Les Lumens
Chapter 4
Erotic Sex Story: Chapter 4 - 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 pulled up in front of the dorm, his stomach doing flip-flops. Jill had carefully selected his rental car, leaning toward the higher end without crossing the line to a sports car or luxury model. His outfit had likewise been chosen to edge toward the popular styles without contrasting too much with his normal, comfortable mode of dress. Despite Jill and Watch both giving him seals of approval, he was still worried that he looked like a nerd masquerading as one of the cool kids.
You can do this. Don't puke, he thought. After a deep breath, he opened the car door and climbed out.
Denise appeared almost immediately at the front of the dorm and headed toward him. "Is that yours?" she asked as soon as she was within earshot.
"Nah, it's a rental," he answered, drinking in the sight of her in Capri pants and a sleeveless top - her blonde hair rustling in the wind. After a second or two of staring with a silly grin on his face, he remembered to walk to the other side of the car.
"That looks really good on you," he said when she reached him and he opened the car door, as Jill had suggested.
Her grin widened when he opened the door. "Thanks." She reached out and ran her finger up his shirt. "This is new, isn't it? I like it."
"Yeah. Thanks. So, ready to go?"
"Mmm hmm. I'm starving."
She sat down and Rodney closed her door before crossing back to his.
"I love new car smell," she said, and then laughed as he climbed in.
"Yeah, it's always a bummer when it fades." He started the car and checked behind him for traffic before pulling out.
"So, when you met your friend from online, how did you do it?"
Coming out of the blue as it had, Rod wasn't quite ready for the question. "Huh? Oh. Well, he said that he was going to be in Galveston, so I suggested a Tex-Mex place we could meet up at."
Denise nodded. "I guess somewhere public is a good idea."
"I wasn't really thinking about that, but yeah, it's probably a good idea. Thinking about meeting someone from online?"
"Mmm hmm. I'm nervous, though."
"Probably different for a girl, I guess," he said, praying that this friend wasn't a guy.
"I'm not really worried about her being crazy or anything."
Yes! One prayer answered.
"I'm just ... I don't know. I'm worried that it will be different in person."
"Do you talk to her a lot online?"
"All the time."
"Don't worry about it then. As long as you're being honest with each other, it's only better in person."
She looked over at him and flashed a grin that made him want to melt in the seat. "Well, I know I am. Honest, that is."
"There you go."
"I need to think about it some more, but thanks. It's not quite as scary since I know you've done it and everything turned out okay."
Okay doesn't even begin to describe it, he thought as he flipped on his turn signal. "No problem."
She moaned when they turned into the parking lot. "It's been too long since I've been here. I don't like coming here alone. It feels weird."
Rod chuckled. "I'm the same way."
"Thanks for asking me."
"Thanks for coming out with me." He found a parking space and shut off the car.
"You can get my door again, if you want," she said, still sporting a radiant smile.
"Coming right up."
Rodney was still chuckling from the last story Denise had related about two girls in a virtual cat-fight on Facebook when he parked in front of her dorm. The entire evening had been filled with such stories, once she sparked the back and forth with one. The only thing Rod lamented was that his best stories were ones he couldn't tell, because they arose in Jill's chat room.
Once again, he got out to open the door for her. Jill had suggested that he go with full-on chivalry, and it appeared that whatever research she had done to come to that conclusion was spot on. Denise never failed to flash him a smile every time he opened a door, pulled out a chair, or stood up when she left the table for the restroom.
Denise climbed out of the car and stood close to him - well within the personal space bubble he'd once assumed was a perfect forcefield for repelling females of the species. "I had a really good time tonight," she said, wearing her heart-stopping smile.
"Me too. I think I ate too much, though."
She giggled and nodded. "Mmm hmm. It was just so good, though."
With her standing so close, the newfound confidence he'd acquired since meeting Jill almost made him lean in for a kiss. He certainly wanted to, but second-guesses kept him from following through. In order to break what was close to becoming an uncomfortable silence, he said, "So, I guess I'll see you in class tomorrow."
Denise bit her lower lip for a moment and said, "Actually, could you take notes for me? I think I'm going to go meet someone tomorrow before I lose my nerve."
"Sure. Don't worry. I bet you'll have a blast."
"I hope so. I'd hate to break such a run of good luck."
Rodney's heart nearly jumped out of his chest when she slipped a hand behind his back and lifted up on her toes. He melted into the brief, but incredible kiss, feeling as if he was hovering several inches off the ground.
"Send me a text tomorrow when you get out of class for the day?" she asked as their lips parted.
"Sure thing."
Denise giggled again, a little color flooding her cheeks. "Okay. Bye. Don't forget."
"I won't. Bye."
She turned and walked toward the dorm, leaving Rod watching her and trying to process the reality of the kiss. She looked back over her shoulder after a few steps, smiled, and waved before continuing on. He stood rooted to the spot until she vanished inside, and then finally returned to the driver's side of the car, fighting off the urge to dance all the way.
Sitting in the car, he finally checked several text messages that had come through on his phone while they were at the restaurant. As he expected, they were all from Jill, asking how the evening was going and growing more impatient with each message.
He quickly typed a reply to the last one. "Just dropped her off. It went great."
In an example of how quickly she could text, a tone sounded from his phone with her response moments later. "Did you get a kiss?"
Cheeks burning, he typed back, "Yes."
"Oh my! Get back here. Now! Be careful, though."
"I will. On my way."
With that, he started the car and began the long drive back to the hotel.
"Yeah, buddy," Watch said as soon as he opened the hotel room door, and held up a fist.
Rod bumped it and chuckled as he walked in. Jill closed a window on her laptop and spun around to say, "Okay. Spill!"
Climbing into the bed next to her and accepting the beer Watch held out to him, Rodney launched into the story. Jill guided the tale by asking questions all the way through, helping him to remember a few things that he'd only noticed in passing.
"And, that's when she kissed me," he finished.
Jill shivered and moaned. "Was it a good kiss?"
"Incredible."
"Better than mine?"
Rod's mouth dropped open. He had no idea how to respond to that.
Jill broke out into laughter. "I'm just teasing. She doesn't know how lucky she is yet, but she's obviously figuring it out."
Watch jumped in with, "Told you that you just needed to loosen up. I could tell that she was into you when I saw you walking back from the movies the other night."
"And I told you she'd swoon when you started opening doors for her," Jill added.
"How did you know that, anyway?" Rodney asked.
Jill winked. "I have my ways."
Rodney lay back on the bed and sighed. "I can hardly believe it's real. It seems more like a dream than reality."
"Oh, it's real," Jill said, and then reached out to trace her finger over his crotch. "And you know what else? I'm really horny."
Rod groaned, hardening instantly from her touch.
"There are still a couple of firsts I haven't claimed yet. Want to check one off the list?"
"Like what?"
Jill quickly swung a leg over Rodney's body to straddle him and dipped down for a long, hungry kiss. Gyrating atop him, she asked, "Do you want to fuck my tight little ass, baby?"
"Oh yeah," he answered while squeezing her tits.
She let out a sexy growl, and then kissed him again. "Let me go get cleaned up and changed. Help Jeff set up the lights."
Rodney shook his head as he sat up, realizing that he wasn't even remotely worried about fucking her on camera. He was even excited, knowing that there would be guys everywhere jealous of him when they saw the video. Watch tossed him a tripod and Rod slid off the bed to set it up.
After a few minutes, they had everything in place and ready to go around the bed. Rod was already rock hard, but when Jill stepped out of the bathroom and asked, "What do you think?" he really started throbbing.
She was wearing a lacy white bustier with half cups, so it only supported her breasts and did virtually nothing to cover them. Below that, she had on matching stockings supported by a garter belt - and nothing else.
"Whoa," Rod breathed, a wide grin spreading across his face.
"Damn," Watch agreed. "That is fucking hot, babe."
Jill chuckled and walked toward the bed. "And this isn't all I bought today. I went a little crazy when Gina showed me this place."
"Bet you make it all up in privates within two days," Rod said as she stepped up next to him and squeezed his hard-on through his jeans.
"Sooner than that. I got everything half price because Gina and I posed for pictures in everything we bought, for the owner to use on his website. He saw me holding this up in front of me and his jaw hit the floor. I'll probably go back and stock up before we leave."
"Cha-ching," Watch said before breaking out into a laugh.
Jill leaned in closer and traced a finger down Rod's chest without releasing his cock. "So, do you think you might be able to handle Jeff working one of the cameras while we play?"
Even he was surprised when he answered, "Sure," without the slightest hesitation.
"Oh my, oh my," she moaned, and then licked her lips. "So get nekkid. You'll know when I'm ready for you."
Rodney sat down in a chair to pull off his shoes, and then went to work on the rest of his clothes. Jill climbed up on the bed and coordinated with Watch to make adjustments to the lights and cameras. Once they were both satisfied, she rose up onto her knees at the head of the bed and gave a nod.
"Hey everybody! Guess what? I got some new naughty things. Want to see?"
She paused for a moment, and Rod looked at the laptop situated near the foot of the bed. His friend was zooming out from a close-up of her face to show off her body.
She let out a theatrical gasp as the slow widening of the view revealed her prominently displayed breasts. "Boobies!"
She laughed and swayed back and forth while the camera continued to pull away, until she was fully visible on the screen.
"This actually came with crotchless panties, but what's the point of that? May as well not wear any at all." She reached down to part her nether lips and arched her back - moaning.
"I think I'll wear this on my first day back on cam after vacation, so you all better be ready to chase off the lame beggars. As soon as one of them sees tits, ass, and pussy in free chat, they're going to come out of the woodwork."
Jill turned around and dropped down onto her elbows, giving an even better view of her folds and showing off her bare ass. Rod's cock throbbed like mad, because he knew that before long, it was going to be deep inside that sexy ass.
"I get so turned on when I'm wearing something new and naughty." She rolled over onto her back and demonstrated that by tickling her folds with her fingertips. Rod could see shimmers from the lights between her nether lips - evidence of how wet she was.
"Mmm, this isn't enough," Jill said while giving her clit a few quick, circular rubs. "I guess it's a good thing I got myself a treat while I was out buying this treat for all of you."
Rod's curiosity piqued as she rolled over to reach beneath the bed. When she came back up, he recognized the Hitachi Magic Wand because he'd researched it after hearing about it on chat.
"I know a bunch of you have been suggesting one of these, so I got one. I couldn't resist getting the rabbit attachment for it, and I think it's going to be perfect for what I have planned for today. You don't know how hard it was to resist trying this out, but I haven't even turned it on yet. I wanted you to see the first time."
Jill flipped the switch and her eyes shot wide open. She held her palm against the phallic part of the attachment and let out a broken moan. "Oh. My. God. This is almost as strong as a sybian. And no batteries to go dead on me at just the wrong moment, either."
The high-pitched hum of the toy died down when she turned it off. "I know I'm going to love this, but guess what? It's only the gravy for the meat course."
As she'd told him, Rod knew his cue when he heard it. Erection bobbing, he took the few steps to the side of the bed and climbed in.
"Mmm, see how hard he is for me?" Jill said as she reached out to stroke his cock. "I bet you're wondering what I'm going to do with it, huh?" She held up the wand with her other hand. "There's a part to go in my pussy, and one to tickle my clitty, so what do I do with this big, hard cock?" She paused for a moment and then said, "He's going to stuff it in my tight little ass, and you get to watch."
Jill sat the toy down on the bed and leaned over to the bedside table. Out came a bottle of lube, which she popped open and held over his cock.
Rod stiffened and gasped as the cool liquid drizzled over him, prompting a laugh from Jill. "I know it's chilly, but we have to get you nice and slippery." Before the lube could dribble down to his balls, she wrapped her hand around his cock and spread it over his shaft. A second squeeze of the bottle and more stroking left him covered in a thick glaze.
Jill handed him the bottle and turned around to face away from the camera. She lowered her face to the pillow, reached back, and spread her ass cheeks wide. "Now me."
Rod saw Watch flip on the other, stationary camera before moving to the foot of the bed with the one he held. Rod took aim at the puckered iris of her ass and squeezed.
Jill let out a yelp and jumped. She had a shiver in her voice when she said, "Oh, that's colder than I thought. Push it in with your finger."
His eyes widened when he felt the resistance to his finger, despite the large pool of lube. With her ass so tight around that single digit, he wondered how in the world he could possibly force his cock inside her. After several more applications of lube, she nodded her head.
"I'm all nice and slippery now. Mmm ... Do you have your cocks out? You'd better. Squeeze them nice and hard and pretend you're fucking my tight little Milf ass too. Are you ready to fuck my ass, baby?"
"Yeah," Rod answered, moving in behind her.
"Oh! I almost forgot." She giggled and grabbed the pillows, situating them beneath her. After a few adjustments, they provided a perfect platform for her to rest the wand on, and she slid the silicone phallus into her canal.
"There. Now I'm ready. Go slow. You're going to have to push hard at first. Hold it right behind the head."
Though he felt as if he was as hard as a steel bar, her suggestion proved useful, because his shaft tried to bend as he pushed against her forbidden entrance. Holding it still, he pushed harder and gasped as the head popped into her ass.
"Oh! Mmm, it's been a while since I've done this. God, it feels huge. I love it. More."
Though she still felt incredibly tight, it was far easier to feed his cock into her than it had been to pass the initial resistance. In addition to the tightness, her ass had a far different texture than her pussy, but it still felt incredible. Inch after inch, he sank into her back door.
"Ohhh, he's so deep. So deep in my tight little ass. I'm so full. Does it feel good?"
"So tight," Rodney grunted, and then groaned as his balls tapped against her nether lips.
"Ah! Oh, that whole big, hard cock is stuffed in my ass. It feels so good. Give it to me, baby. Fuck my ass."
Rodney started and Jill squealed when she flipped on the magic wand. He could feel the powerful vibrations running through her body, tickling his buried member as he withdrew, and then thrust again.
Jill looked back at him. "That's it. Fuck me, baby." She then turned her attention to the camera. "He's fucking my ass so good, and my new toy is setting my pussy on fire. Stroke your cocks. I want you all to come too. I want to imagine every one of you spraying me with cum - covering me in it from head to toe."
Rod picked up the pace, grunting with effort every time he forced his cock into her ass. It felt hotter than her pussy, and there was certainly more friction. After only a few strokes, he pulled back just a little too far. It felt as if she was squirting him out when he slipped free.
"Some more lube before you put it back, but hurry."
Rod snatched up the lube bottle from where he'd dropped it. Once again, she spread her cheeks wide, revealing that she was gaping from his girth inside her. She squealed loud and long into the covers as the cool liquid streamed into her ass. After a generous amount had dripped inside her and welled up into a pool that ran down the cleft between her cheeks, he put the bottle down.
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