Jessica - The Making of a Cockslut

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18-year-old Jessica loses her virginity.
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Dillinger
Dillinger
308 Followers

(This is a prequel to "Jessica's Big Dick Adventure" and the first new erotic story I've written in nearly four years. In this story, and perhaps others to come, I want to explore Jessica's earlier adventures, prior to her marriage and when she was just developing into the magnificent cockslut that she became. I've often thought that, there being nothing pee wee about the COCKs that Jessica encounters, this series would make a more entertaining, and certainly a moreTitillating movie than "Pee Wee's Big Adventure." What would you rather see... Big Dicks or Pee Wees?

This story was written after all the stories in "Jessica's Big Dick Adventure" but chronologically takes place before those stories. There will hopefully be more installments of her earlier adventures and then perhaps I'll go back and write about her newer adventures. I guess I've kind of got a George Lucas thing going here... but with a lot more sex. Actually, with pretty much nothing but sex... and absolutely no light sabers or Ewoks.

Please don't forget to vote and, for any of you horny readers who are kind enough to send feedback, I'd be very curious to know who you think should play Jessica in the movie version of these stories. My guess is that most of the guys who respond will say Angelina Jolie. Of course if Angelina took the part she'd have to get a boob job to make her tits bigger, but for the sake of her art I'm sure she'd have no problem with that. Just let me know who you'd cast and I'll write a letter to whichever actress gets the most votes and see if it can be arranged.

As far as the enormously endowed men Jessica seems to draw to her in droves, they're all modeled after me, of course, and I'm personally claiming first dibs on the lead male role in the movie - especially if Angelina Jolie wins in the voting. In fact I'd be happy to play ALL the male roles in the movie. I've been practicing and have trained my cock to take on 3 uniquely different roles... Big, Damn Big and... Holy fuck that thing is HUGE!!!)

In The Beginning: How Jessica Lost Her Virginity.

Jessica was jogging along a path in the local park when she noticed that a young man she'd never seen before seemed to be following her. He jogged along at a distance behind her for a long time, slowly gaining on her until he was just a few feet behind her. She could feel his eyes taking in every inch of her lovely young body as he sped up just a bit and was suddenly running right next to her.

She glanced at him. Jessica was often approached by young men when she was alone. Often they got tongue tied by her beauty and became shy. What was different about this man was that he looked a bit older than most. He also was very good-looking and obviously in excellent shape. Jessica actually found herself a little bit flattered by his attention and when he invited her to join him for a rest just off the path on the grass behind a few trees, she quickly accepted.

Sitting there Jessica became very aware of how her ass checks bulged suggestively out from under her tight shorts. They were so tight that the outline of her pussy was clearly visible through the tight material as well. Her large full tits hung heavy inside the tight halter, shimmying and shaking each time she moved, quivering with each deep breath she took.

"You have incredible tits!" he said suddenly, as he ogled her unashamedly. "They're really fucking huge!"

Jessica couldn't believe he was saying this to her or that anyone could be so bold (especially someone whose name she didn't even know yet), but she knew he was right. Jessica knew she was a knockout. She had a gorgeous face with full, pouty lips and thick, lustrous, reddish-brown hair. She had great legs, incredible legs in fact, and a nice tight firm body with big tits. Really BIG tits. She was what you call stacked. Totally.

The two of them were lying on the ground behind a couple of trees, not far from the path. He had been lying on his side and staring at her hungrily while she blushed. Jessica now found herself blushing even deeper at his unexpected and outrageous remark. She was caught off-guard and had no idea what to say to something like that. Jessica suddenly felt very self-conscious.

"I mean your tits are amazing, they're not only big but they look incredibly firm," he leered. "Not many women with your bust size could get away without wearing a bra. Hell, not many women even have anything close to your bust size!"

"And your ass," he continued "is terrific too! It's the first thing I noticed about you when I saw you jogging in front of me. With those cock-teasing little shorts you're wearing your butt cheeks were damn near falling out! I started getting a hard-on just looking at them!"

Jessica blushed yet again. Why was he talking to her like this? In all her previous experience the young men who tried to approach her got tongue-tied and had trouble with any kind of conversation at all because she was so gorgeous and so sexy. They merely ended up staring at her tits, unable to tear their attention away from her incredible chest long enough to look her in the eye. This guy was unlike anyone she had ever met. He was using words like "tits" and "hard-on" without any embarrassment at all. Jessica was shocked. She knew in the back of her mind that she should probably just get up and leave, but this was so outside of her field of experience that she had no real idea how to respond or react. Plus, she had to admit to herself, she was flattered. No one had ever talked to her like this and she found that she was enjoying the comments, even if they were lewd.

"And," he went on, "you have these long sexy legs and this tiny little waist with the biggest, fullest tits I've ever seen. You're a total fucking knockout!"

Jessica still didn't say anything. She gazed down at her feet and was very conscious of how fast her heart was beating. She found herself still unable to look him in the eye.

"I bet you're a virgin, aren't you?" he teased. "I bet you haven't even let anyone touch those magnificent tits of yours."

"Yes I have!" she exclaimed. For some reason Jessica didn't want this older guy to think of her of as an immature or inexperienced young girl. "I have too let someone..." she hesitated "... touch them!"

She looked up defiantly and her lovely green eyes finally met his briefly, but then quickly she looked away. She didn't know why but she wanted to impress him. Maybe because he was a little older and more self-assured than the other young men she usually came in contact with. "This is silly, Jessica," she said to herself. "You don't even know him."

"Have you ever let a guy play with them, let him fuck those luscious tits of yours?" he persisted. A wicked glint appeared in his eyes as he continued to tease her. "Have you ever felt a guy's big fat cock between your huge tits and let him fuck them? Let him fuck your tits until he shoots a big load of jizz in your face? I bet you've never done that!"

Jessica didn't say anything in response but had to confess to herself that she never had. Were there really people who did such things? She imagined what it would be like to have a guy fuck her tits and cum in her face. What an incredible thing... and what a dirty thing to do. She had never before imagined such things in her wildest dreams yet the image of a penis, a cock (his cock?), fucking her tits wouldn't fade out of her mind's eye.

"I bet you've never even given a guy a hand job... jacked off a big hard cock, have you? You're not fooling me. I bet you've never even had a cock in your hand!"

"I have, too!" she sputtered. "I have too had a guy's thing... uh... c-c-c-cock in my hand!" She found herself stuttering foolishly at the word "cock."

"OK then, show me," he grinned, knowing he had her backed into a corner. "If you've done it before, held a big cock and jacked a guy off, then go ahead and prove it. I don't believe you!" He shifted his weight and pressed his crotch up toward her as he grinned hungrily into her pretty eyes and then let his gaze slowly lower to stare at her big tits.

Jessica hesitated; she was now caught up in her own lie and her own stubborn insistence not to let this guy think she was inexperienced. Now she didn't know how to respond. She glanced over, and then stared at the throbbing cock-bulge in the front of his pants. It looked so big, ridiculously big, it looked absolutely massive. Jessica was nervous breathing heavily now. She knew that once she started this there would be no going back. Jessica took a deep breath... then another, slowly reached out her hand, hesitated, and then gingerly gripped the clasp of his fly cautiously, as if it might bite her.

The young man was smiling to himself and wondering just how far this obviously inexperienced young woman would allow herself to go. When she actually tugged on the zipper and slowly pulled it down he felt the blood begin to surge into his giant cock and shivers run through his balls. He leaned back and relaxed, determined to let her do all the work, despite the overwhelming desire to grab her and ravish her.

Jessica stared at her hands in amazement, her eyes wide, her mind not comprehending what she was seeing her own hands doing... how had she got herself into this situation? She finished unzipping him and she then nervously unsnapped his jeans. With shaking hands she gripped the top of his pants and tugged on them, pulling them down. Then he waited patiently, grinning, while she stared at his briefs and wondered what to do now.

"Oh my god, it's so big! It's huge! Oh my god, oh my god, oh my god..." Jessica trailed off staring at his crotch. Even though she could not yet actually see his cock it was bulging out ridiculously, immense beneath his tight black briefs. She could actually see it pulse. "I can't believe it; I can't believe it's so big! It can't be that big! Oh my god, oh my god, oh my god..."

"Take it out, it's ok. Go ahead and take it and look at it. Play with it," he encouraged. His cock was throbbing inside his tight briefs. She continued to hesitate, to just stare at the pulsing mass of manhood that was barely contained by the material of his briefs, so he decided to pressure her a bit. "I don't think you really know what you're doing," he teased. "You've never even seen a cock before let alone played with one. Go ahead and admit you don't have a clue what to do with it."

"I do too!" she said, tilting her head to the side as if trying to get another angle on the massive bulge in front of her, sticking her tongue out from the corner of her full lips as she did so. Jessica nervously raised her hands to the top of his shorts. Slowly, hesitantly she pulled down on them. His cock had grown so large now that for a second it looked like she wouldn't be able to get his briefs off without ripping them. Suddenly, catching her off-guard, his cock sprang out over the top of his shorts practically smacking her in the face. His cock was vibrating with life, it was huge... thick, hard and throbbing.

Jessica leaped back in surprise, fearful of the massive weapon that had exploded from his shorts, aimed right at her face. "OH MY GOD!!!" Jessica exclaimed. She was absolutely astounded at the size of his prick. Not only was it amazingly long, but it was thicker than her forearm. It wasn't a penis, it was a club, a rocket, a tree-trunk, a... COCK!

"Do you like what you see? Do you like my cock?" he prodded. "Go ahead and touch it. See if you can wrap your fingers around it. Go ahead and play with it. You're not shy, are you?"

On autopilot now, following his directions, Jessica reached down and attempted to wrap her fingers around the huge shaft of his throbbing erection. There were several veins running up the trunk of his prick and she could feel them pulsing with blood as she squeezed his cock in her hands, her fingers not even beginning to reach around the diameter of the massive organ. The large majority of it thrusting out from above her hands and looking as if she was holding a baseball bat.

"Do you have any idea what to do now?" he taunted her. "Huh? Do you?" He was curious to see if she had any clue at all what to do with his big cock, now throbbing in her hands. He shifted his weight a bit, moving a little closer to her and making it easier for her to get at his cock.

Jessica murmured something inaudible and then, slightly louder; "Of course I do... I know. I do to know what to do!" she managed to say almost defiantly. Then she began to erratically pull on his cock, tugging it first in one direction, then another. He gasped in pain as she awkwardly mauled him.

"Fuck! Take it easy! Slow down! Handle it gently. It's a cock, God damn it, not a friggin' pump handle" he nearly shouted. Just as he was about to reach for her hand and pull his cock out of her grip she suddenly began doing what she was told, running her hand gently up and down the thrusting shaft, almost tenderly now. She pumped his cock slowly as she leaned forward a bit to get a closer look at his stiffening cockmeat. She was amazed that, as big as thick as it was, it was obviously still not fully erect. It was growing bigger and bigger, and in no time she was going to have him primed to his full size and hard as a rock.

"Oh... my... God! It's so big! And it's getting bigger, it's getting even bigger! Oh... my... God, I can't believe how BIG it is!" she muttered, her eyes growing wider and wider in astonishment.

"Oh, Fuck! Ohhh, fuck yes!" he moaned as he thrust his hips toward her. Damn, she was good... really good! If this was her first time handling a cock then she sure was a quick study, a natural.

"Does that feel good? Do you like it? Do you like what I'm doing? Does it feel good when I jerk it up and down like this?" she asked innocently, tearing her off his cock for a just a moment to look up into his face.

"Hell yes, girl, I'll say it does... oh fuck yeah!" he grunted, staring down at her tiny hands pumping away at his massive dick. "Why don't you go ahead and play with my balls too?" he encouraged.

With great enthusiasm Jessica now returned her attention to his big cock, one hand stroking the thick shaft while she brought her other hand up to his proportionately large balls. His hugely swollen nuts bumped together as she alternately lifted and dropped them. They rolled around against each other as she cupped them in her hand, feeling so very heavy as she lifted and weighed them. She thought this was really neat. How truly wonderful! And so big, just like his cock. She was beginning to gain a real appreciation of the male body!

"Oh yeah, oh yeah, that's it... just like that! Oh yeah!" he encouraged. "Don't stop what you're doing, that's perfect. That feels so great. Keep jerking my cock and playing with my balls at the same time! Damn, you're good!"

Jessica smiled happily to herself, a thrill shooting through her as she realized she was truly pleasing him. She didn't have nearly as much experience as she had pretended in fact, she really had no experience to speak of, but it seemed that didn't matter after all. She was pleasing a man for the first time, and obviously doing it quite well by the way he was reacting. He seemed to really be enjoying the way her hands worked his manhood.

By now his cock seemed to have grown to its full size. It had to be, there was no way it could possibly get any bigger or any harder. It was immense and it was throbbing delightfully in her hand. Jessica's self-confidence was growing quickly now as he started to groan.

Hearing his groans Jessica stopped shucking his shaft and looked into his eyes. "Am I doing something wrong? Did I hurt you? I'm not hurting you, am I?" she asked, her self-confidence slipping away as quickly as it had come. "Am I jerking it too fast, too hard?"

"Hell no!" he enthused. "Are you kidding? You're fantastic. You're great! You're absolutely amazing! I have to admit, you really do know what you're doing. You're the best!"

Jessica smiled brightly, her self-confidence back in full measure, she had pulled it off and he really did think she was experienced! So up and down, up and down, her hand flew over his cock, faster and faster. And, amazingly, his already immense cock actually seemed to be growing even larger... expanding, thickening, and forcing her fingers even wider apart. She felt like she was trying to grip a tree trunk it was getting so big!

As she played with his cock he had been ogling the bouncing globes beneath her tight halter. "I want to see your tits! Let me see your big fucking tits!" he exclaimed suddenly and immediately reached for her halter-top; slipping his fingers underneath it and pulling up. He had to tug hard to get the tight material off of her incredible chest. All at once her big gorgeous tits were free, bursting out and bouncing up and down, shimmying and shaking from side to side.

"Ohhhhhh!!!" she gasped in shock, surprised to see her luscious tits bouncing free. Yet even so, she didn't miss a stroke on his cock... she continued to pump it up and down, up and down. She loved the feel of it, she loved how big and hard it was and she loved how it throbbed in her hands.

"I don't fucking believe it!" he exclaimed. "Your tits are amazing!" He pulled her halter-top all the way up to her chin. "They're fucking perfect... big and firm! And your nipples are as hard as rocks!"

He was now squeezing the pillowy flesh of her breasts, running his hands over them, playing with them. He dug his fingers into the pliant flesh and squeezed them. As big as his hands were they still seemed small compared to her full heaving breasts. He ran his fingers in circles around the hard buds of her nipples, he pressed them in and then pulled them out, he pinched them lightly and she squealed with pleasure. He pulled on her tits to bring her closer to him and she leaned forward helpfully as he did so.

"OH MY GOD!" she exclaimed, as his mouth pressed against one of her erect nipples and sucked on it. "Oh yes... YES! Suck my nipples! Suck them. Oh God... Yes!!!"

His tongue was flick-flick-flicking against her stiff nipple, up and down, back and forth, running circles around them, then poking at the tip, and then running circles again. He began to gently nip at them with his teeth, pulling on the nipple as he held it in his mouth, scraping his teeth against the hard sensitive bud.

"Oh God, Oh God, Oh God yes it feels so nice! Oh God yes!" she moaned, as her fist continued to jerk the thick throbbing shaft of his cock, her hands moving up and down in a blur of motion. "Suck them, suck them... suck them! Suck my tits! Suck on them!"

He drew his mouth slowly off the nipple he had been working on and began licking his way over to the other one by licking down and up her tits, he returned for a moment to the first nipple and sucked on in before licking and kissing every inch of her tit-flesh. Then buried his head in her cleavage and used his hands to press and squeeze the large globes against his face. Finally he licked his way over to the second nipple and began to suck on it. Shivers ran through her body as a slight wind blew her wet, shiny flesh dry.

The veins on his cock were now bulging out, seemingly ready to burst under the built up pressure. The head of his cock had turned a deep red and a huge pearly drop of pre-cum seeped out of the tip of his cock and fell in a gooey string across her fingers as she continued to stroke the massively thick shaft. Jessica thought it felt warm and sticky, enjoying the sensation of the hot liquid against her skin. She had heard about guys cumming when they got all worked up and figured this must be it. But what he said next surprised her more than anything that had happened so far.

He pulled away from her tits and looked her in the eye. "Gotta fuck you!" he grunted. "I have got to fuck you, you hot little slut! That amazing hand job of yours has built up a huge load of cum in my balls and I'm ready to fill your hot little cunt with it!"

Dillinger
Dillinger
308 Followers