Vanessa Pursues

Authors Note: All characters in this story are over 18 and are consenting adults. Please read "Vanessa's Awakening" for an introduction to Vanessa.

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Not long after their lazy Saturday afternoon in the Newman's backyard Vanessa set her sights on a new person to pursue. All through high school Vanessa's tender heart always came back to Jacob. Jacob was a fellow graduate from high school and someone who she never approached beyond a classmate level of friendship.

Jacob turned 19 that January and stood a little over 6'1" in height and had what could be called a husky figure that made him look like a man who could be a stand in for a young Hugh Jackman. Jacob was smart and witty but also shy despite his hulking figure. Vanessa just loved his dry humor and how carrying he was.

Vanessa knew she had to let Jacob know how she felt about him before he and his friend Zach started their Pleb year at the US Naval that August. After speaking with Cassidy as how best to do it, Vanessa came up with a plan. She only hoped it would work.

Jacob got a call from Vanessa as he was leaving work on a Wednesday evening. After an 8 hour day in the heat of July cutting grass, Jacob was really tired. All he wanted to do was to go home, take a shower and eat something before crashing in his bed to be up early for work the next day.

Jacob heard Vanessa's voice say, "Hey Jacob! Hows it going? I was wondering if we could get together sometime soon?"

All thoughts of sleep and rest left his mind as the girl he was too shy to speak with, just called him out of the blue. "Hi Vanessa, I would love too. How does this Friday sound?"

The two made plans for Jacob to pick up Vanessa at seven that Friday evening. Jacob's dad congratulated Jacob on his date and allowed him off a few hours early so he could get ready. Jacob pulled up to Vanessa's house 5 minutes before seven in his ten year old F-150 pickup. Jacob nervously shook the shifter as he checked himself in his visor mirror and popped a Listerine strip in is mouth before exiting his truck and knocking on Vanessa's front door.

Vanessa answered the door in a mid length sun dress and sandals, her glasses highlighting her bright green eyes that shined and accented her big smile when she saw Jacob at the other side of the door.

"You look great Jacob! You clean up really well!" Vanessa told him as she closed the door behind her.

"Vanessa, you look incredible!" Jacob told her, his face flushed red as he spent a lot of his strength facing her and not turning away in embarrassment.

"Thank you Jacob! That means a lot to me," as she takes his offered hand as he leads her to the passenger side of his truck and opens the door for her.

Jacob can't take his eyes off of her as he slowly closes the door for her. He walks in a daze to the driver's side and climbs in and asks Vanessa, "where too?"

"Take us to Mariner Point Park."

"Okay," Jacob says as he pulls away from the curb. His mind shifts the truck's gears from muscle memory, as the girl of his dreams sits less than a foot from his side.

With in 20 minutes Jacob pulls into the long driveway of the park and takes both of them to the back parking lot where he pulls into a space by the pavilion. Jacob got out and helped Vanessa out of his truck and smiled as she led him past the pavilion on to the asphalt trail towards the back of the park grounds.

The couple strolled slowly together as the setting sun highlighted the shadow under the trees that covered the trails as they approached the observation deck near the train bridge that crossed the Susquehanna River. Vanessa motioned for Jacob to sit beside her as they saw a Amtrak train crossing the bridge. A breeze off the water blew a strand of Vanessa's curly light brown hair into Jacob's face. Jacob went to brush it out of his way when he turned to face when Vanessa faced him and kissed him full on the lips.

Vanessa was just as frightened as Jacob. When the noise of the train came around the wind blew her hair towards Jacob as she turned toward him. Vanessa partly raised herself up and kissed him. Jacob returned her kiss and they both opened their mouths to the other, as their tongues wrestled amongst themselves. Jacobs hands held Vanessa against him as she had one hand on his strong thigh and another holding his rough cheek, that moved to run through his short brown hair.

Jacob wouldn't dare take advantage of a woman. His up bringing and beliefs he held to growing up stopped that but when Vanessa's small hand found his and moved it over one of her large breasts and held it there. He could feel her nipple poke out against the fabric of her dress as she aggressively kissed him and began to bite his lips.

Jacob was at a loss. His cock was hard and pressing against his khakis rather painfully. His right hand was grasping his first ever breast of a girl he has had a crush on since Sophomore year. Jacob was at a loss of what to do next.

Sensing his hesitation, Vanessa pulled away some and looking Jacob directly in the eye, pulled down her dress straps, and freed her 42DD breasts from her bra. As she moved both of Jacob's hands onto her firm chest. Jacob saw her dark freckles mixed with goose bumps as Vanessa told him,

"Touch me wherever you want! I want you Jacob. I always have. I have just been too scared to tell you."

Jacob said, "I have the same problem. I am way better at electronics then with people,"

Jacob gingerly holds her breasts in both of his rough hands. Vanessa looks at him with such love and bites her own lip as he massages her mammaries with such care that he reads her face and sees what each pinch, and movement of his hands does to her face and her slowly squirming body.

Vanessa unbuttons Jacob's shirt and caresses his hairy chest, pulling on the hairs and running her small finger nails downward which causes Jacob to moan into their kiss. His straining cock is begging to be touched. As if reading his mind, Vanessa stands up and steps out of her dress, leaving her in only her pink panties and sandals.

Vanessa pushes Jacob back on the bench and kneels before him with a devilish look in her eyes. Her hands move to his bulging crotch where she slowly undoes Jacob's belt buckle and unzips his fly. She reaches through the fly and grasps his cock through his boxers. Jacob cries out in a yelp as her cool small hands come in contact with his 8" shaft.

Unable to bend him through his boxers she pulls down his boxer shorts and gasps as she sees his cock spring out at attention. Pre-cum is beaded on the slit of his cock head. Vanessa swipes it up with her pointer finger and looking Jacob in the eye, smiles as she licks it off her finger. Jacob can't believe what is happening.

He tells her "I've never done anything like this before."

Vanessa tells him, "I have a little bit. In a way, I have learned about all of this for you."

Not understanding that statement Jacob groans when Vanessa takes his cock in her mouth. Vanessa licks up his shaft and swirls her tongue around the mushroom head. Then she slowly gets a slow rhythm of bobbing up and down on his cock. Her cheeks bulge out like a chipmunk as she sinks her mouth down to his curly pubic hair as she deep throats him. Looking Jacob right in the eyes. Jacob looks down at her and mouths that he is going to cum soon as Vanessa bobs a few more times in his cock. Vanessa feels his cock tense in her mouth as Jacob splashes the back of her throat with his seed, as she pumps her hand on his cock. She gets every drop in her mouth. Vanessa looks at Jacob as she swallows his cum. Jacob moves her towards him and kisses her deeply.

Jacob pulls away and looks her in the eye and asks. "how can I pleasure you?"

Vanessa moves his hands to either side of her large curvy hips and has him lower her panties to her feet so she can step out of them. Vanessa pulls Jacob on top of her as she pushes his head south of her waist. Jacob can see his first ever pussy glistening in the waning light of dusk. Jacob tentatively moves between Vanessa's legs and smells the musky sweetness of her womanhood. Vanessa's small hands guide his mouth into herself as Jacob open french kisses her bald sex.

Just as he was with her breasts, Jacob takes his time getting to know the rest of Vanessa's body. Vanessa moans and sighs as he licks her. He brushes her lips with his finger and pushes into her. His mouth finds the erect nub of her clitoris and he sucks on it as he fingers her upper muscle finding her g spot. Vanessa arcs her back and moans in pleasure as Jacobs plays her like a harp. Vanessa holds Jacob's head in her hands as he eats her out.

Vanessa tells him how to touch her with his mouth by the sound of her coos and moans. Her hands hold his face against her sex as Jacob tongues her engorged clit causing Vanessa cum all over his face. Jacob relishes giving pleasure to the woman of his wet dreams.

Vanessa holds him as she regains her breath. "My you are very talented doing that. Care to use your cock inside me," Vanessa grins wickedly as she spreads her legs inviting Jacob's hardening 8" cock to her moist entrance.

Jacob lines up the head of his shaft to her pussy and at her urging eases in slowly to her sex. Jacob groans as she envelopes his member inch by agonizing inch until his balls rest against her taint.

"My Jacob you have filled me up. Care to fuck me now?" Vanessa says with a twinkle in her eyes.

Jacob slowly moves in and out of her. "Am I hurting you?" He asks, concern on his face which Vanessa sees is full of love and care for her well being.

Vanessa shakes her head, "Don't be gentle with me Jacob. We can be gentle later. Ram that hard cock into me as hard as you can. I can take it!"

Jacob moves against her harder. His cock slides in and out of her as he feels the walls of her vagina close around his thrusting cock as he nearly enters her cervix. He pounds her hard enough that his balls slap against her ass.

Vanessa bares her teeth as sweat drips down her face onto her full breasts that rock back and forth with each thrust. Vanessa urges Jacob to fuck her harder. She is so close to cumming again.

"I am almost there Jacob. I love how your cock is beating my pussy to submission! Cum in me Jacob! Make me your woman!"

Jacob complies as shoves into her as hard as he can and can hold it in no longer. Vanessa's dirty talk contrasts so much to the sweet girl he knew in school so much that Jacob finally lets go of what he is holding back. Jacob moans in almost roar as he releases inside of Vanessa who half a second later him clamps down around his cock and convulses as her own very powerful orgasm takes over and both ride out the waves of pleasure that roll through the both of them.

Jacob holds her face in his hands and kisses her deeply embracing her. He sits next to her as the sun goes below the horizon of the train bridge and a cool breeze blows across their mostly naked bodies as they embrace and whisper how much they love each other.

An hour passes as they slowly get dressed and make their way back to his truck. Jacob takes his time driving her home. He walks her to the door and kisses her deeply as both lovers find it hard to let each other go.

When Jacob gets home and in his bed he finds a text from Vanessa with an attachment included. Jacob opens the text to find a puncture of Vanessa laying on her own bed breasts exposed and the biggest smile he ever saw on her face. "Good night lover!"

The End