The Student - Friday Night at The Windjammer

Roger was sitting on the big, soft couch in the living room wearing just his jeans and shoes, sipping champagne when Jessica came out of the bedroom a short while later.  She was wearing a pair of skin tight dark blue high-waisted “short-shorts” in the style that was popular in the 1950’s and a white midriff top that tied at the bottom just beneath her big breasts and buttoned up the front.  Of course, all of the buttons were open and her mammoth globes were being held in only by the knot at the bottom, but Roger was quite sure that’s just what Jessica had in mind.  The top was, in typical Jessica style, at least two sizes too small which meant that it hugged every curve and swell of her big, heavy breasts.  And of course she wasn’t wearing a bra, her nipples clearly visible beneath the white cotton fabric.  She was barefoot, and Roger noticed for the first time that her toes were painted red.  She smiled at him as she padded barefoot across the room, and by looking at her you never would have known that a mere 10 minutes earlier they were fucking their brains out in that very room.

“Nice outfit,” Roger said, smiling back at her.

“I’m glad you like it” Jessica replied, stopping at the coffee table and bending over to pick up the glass of champagne that Roger had already poured for her.  She gave Roger a clear view of her spectacular cleavage as she did so, and of course she was doing it on purpose.  Jessica was a natural tease, and Roger liked it.  “I thought it was appropriate considering that we are, after all, at the beach.”  She paused as she took a sip of champagne, looking over the rim of her glass with hooded eyes at Roger as she did so.  Roger took another sip from his glass as well, watching Jessica as she walked over to the big sliding glass door leading out to the balcony.  She slid the glass door open, letting in the night breeze and the sounds of the ocean.  Jessica took a deep breath of the night ocean air and sighed, a smile crossing her lips.

“I just love the beach!” she said, looking out over the water.  “It’s my favorite place in the whole world!  No place else on earth makes me feel as relaxed and comfortable as the beach,” she said, turning around to face Roger.  “Don’t you like the beach, Roger?” she asked, her hair blowing slightly in the breeze coming in from behind her.

“I love the beach,” he replied.  “I feel the same way you do about it, only maybe not quite as passionately.  Then again,” he continued, pausing to take another sip from his glass, “you seem to be quite passionate about anything that interests you.”

“Or anyone,” she replied, smiling coyly at him as she continued.

“And yes, my pet, I’m quite passionate about everything I do.  Life is too short to take anything for granted, and if you’re going to get anything out of the short time you’re alive you’ve got to take advantage of it.  Wouldn’t you agree?” she asked.

“Absolutely,” Roger replied.  “Of course, being rich helps!” he said, grinning at her.  Much to his relief she grinned right back at him.

“Yes, being rich helps!” she agreed, her green eyes sparkling. 

“And being drop-dead gorgeous and incredibly sexy helps, too,” he continued.  She gave him a sexy smile as she replied.

“In some instances, yes it does,” she said in a low, sultry voice.  “You’re not too bad yourself, you know.  I’ve never met a man with your – shall we say, ‘special talent’ – before, but I’m certainly glad I did!”

“So am I,” he replied, meaning it.  They looked at each other in silence for a few more moments, neither of them saying a word but speaking volumes to each other.  A knock at the door broke the spell.

“Room service!” a muffled voice called out from the other side of the door.  Jessica looked past Roger at the door to the room, and the corner of her mouth turned up in a slightly evil smile as she had an idea.  Roger knew immediately what it was, even before she spoke.

“Shall I answer the door, Roger, or would you like to do it?” she asked.  Roger returned her slightly evil smile as he replied.

“You do it,” he said.  “Give the poor guy a thrill, something to talk about with his buddies when he gets off work tonight.”

Jessica’s evil grin got bigger as she walked across the room, placing her champagne glass on the coffee table as she passed by.  She pulled the sides of her open shirt further apart, baring as much of her mountainous breasts as she could, and Roger could see that her nipples were hard and poking out with excitement.  He felt his own cock stir in his jeans as he got a look at her ass wiggling as she walked by.  She passed out of his sight in the short hallway leading to the door, and Roger heard the door open a moment later.

“Room ser – holy shit!” he heard the waiter exclaim, and he chuckled to himself.  He could just imagine the look on the young man’s face when the door opened and he got his first look at Jessica and her humungous boobs. 

“Why, thank you, sir,” he heard Jessica coo at the waiter in her usual sultry voice.

“Will, uh, can I – is there, uh,” Roger heard the waiter stammer.  He was obviously losing the fight to maintain his self-control, and Roger knew just how he felt.

“This is fine, thank you,” Jessica said, laying it on thick for the waiter’s benefit.  “If we need anything else I’ll be sure to call you!” she said, and a moment later Roger heard the door close.  Jessica walked back into the room, pushing the room service cart and giggling to herself.  She was literally glowing, her nipples two hard pebbles poking out against the cotton fabric of her top, and Roger was pretty sure she was wet between the legs as well.  Her giggles turned into a soft laugh as she came into the room.  She parked the cart next to the coffee table and then plopped down on the couch next to Roger, her huge mounds bouncing inside her top as she did so.  She was still laughing at what she had just done.

“Enjoyed that, did you?” Roger asked, smiling over at her as she finally got her laughing under control.

“Oh, my, that was good!” she replied, stifling a giggle.  “The look on his face was priceless!”

“I’m sure you made his night, Jessica,” Roger said, smiling at her with genuine amusement as he got up and walked over to the service cart.  The aroma of the meal made him realize just how hungry he was, and he was ready to eat. 

“I’m sure I did!” she said, stifling another giggle as she looked up at Roger.  The right side of her face was covered with her long, auburn hair as usual, and Roger thought that she had never looked sexier – or prettier.

“Shall we eat?” he asked, motioning to the service cart.

“Yes, let’s,” Jessica said, sitting up on the edge of the couch.  “And after that, let’s go for a walk on the beach!  I love walking on the beach at night!” she said, the excitement in her voice plain.

“Sounds like a plan to me,” Roger said.

A little more than an hour later Roger and Jessica were walking on the beach in the moonlight, Jessica’s long auburn hair blowing in the gentle night ocean breeze.  They were both barefoot, having left their shoes in the room, and Roger had put on his polo shirt before they left.  The beach had always been his favorite place in the whole world, especially at night, and he was glad he had found someone who shared his passion.  He looked over at Jessica and saw the smile on her face as they walked along.  She was obviously at peace, enjoying the moment as much as he was, and her smile grew a bit bigger when she looked over at him and saw him looking at her.

“Penny for your thoughts, my pet,” she said as they continued to walk in the soft sand.

“I was just thinking how peaceful and happy you look right now, walking along the beach like this,” he replied.

“I am, very much so,” she said, looking up into his eyes.  “But I’m going to be even happier in a few minutes.”

“And why is that?” Roger asked, genuinely curious.

“See that lifeguard house just up ahead?” she asked, pointing down the beach to the small wooden building set on stilts about twenty yards or so ahead of them.

“Yes, I see it,” Roger replied.

“I’m going to be happier in a few minutes because when we get to that lifeguard house I’m going to take you inside and suck on that wonderfully large cock of yours, and I’m not going to stop until you cum in my mouth!” she said, giving Roger a seductive, slightly evil smile.  Roger felt his cock stir in his jeans at the thought of what she had just said.

“You are, huh?” Roger said, playing with her.

“Yes, I most certainly am,” she replied, playing back.  “Would you like that, my pet?  Would you like me to suck the cum out of your cock?” she asked, her voice going low and sultry.

“Very much,” he replied, looking down at her.  He felt the tube of his cock begin to swell as the anticipation of what was about to happen set in.

“Good!” she said, looking up at him as they continued to walk towards the lifeguard house, the desire in her eyes plain.

A few minutes later they were at the lifeguard house, and Roger stepped back and let Jessica go inside first.  He couldn’t help but notice the rounded globes of her firm ass flexing as she climbed the short staircase leading to the door, and she must have known he was looking at her ass because she glanced back at him over her shoulder and smiled.  He followed her inside, closing the door behind them as Jessica walked across the small room to the shelf below the wide window facing out towards the ocean.  She turned and leaned against the shelf, placing her hands on the edge and straightening her arms which effectively pushed her huge breasts together.  Roger could see the hard nubs of her already-erect nipples pressing against the cotton top, and he could see the tops of her breasts moving up and down as she breathed.

‘Damn, she’s beautiful in the moonlight!’ Roger thought to himself.  ‘Hell, she’s beautiful in any light!’

“Come here and kiss me, Roger,” she said in her usual low, seductive voice.  “I want to feel your lips on mine before you feel my lips on your cock!”

She held her arms out to him, and Roger crossed the small room to walk into them.  He slid his arms around her young, firm body as she did the same, embracing him and pulling him close to her.  He felt the firm mounds of her large, heavy breasts press against his chest as he lowered his mouth to hers; their lips touched, soft and gently at first, Roger marveling again at just how soft her lips were.  Jessica pulled him closer to her as the kiss deepened, her tongue  snaking into his mouth as she pressed her entire body up against him.  He could feel the heat emanating from her pussy as she pressed against him, sucking his tongue deep into her mouth.

Jessica felt her desire welling up inside her with astonishing speed, and she moaned softly as she hooked a leg around one of Roger’s legs behind the knee to pull him closer to her.  She had been with many men during her short life, but there was something about Roger that sparked a fire deep inside her, deeper and faster than any other man she’d ever known.  Part of it was his big cock, to be sure, but there was something more than that.  Something else, and Jessica was having a hard time putting her finger on just what it was about Roger that affected her the way it did.

But right now all she wanted was his cock in her mouth.  She slid her hand down between them and grabbed the big, hard bulge of his cock from the outside of his pants, and she heard him moan as she gripped it firmly.  Her hand firmly locked on the bulge in his pants, Jessica broke off the kiss and slid her tongue up the side of Roger’s neck to his ear.  She ran her tongue around the outside of his ear twice, and then plunged it into his ear.  She was pleased to feel Roger jump and hear him moan, and she felt a distinct jumping of his cock in her hand as well.  She slid her limber, wet tongue in and out of his ear for several long, enjoyable minutes, and was pleased to hear Roger’s breathing begin to quicken. 

Roger tightened his grip on Jessica as she slid her tongue in and out of his ear.  His ears had always been a very sensitive erogenous zone, and only two or three women had ever discovered it.  His cock was now rock-hard and throbbing beneath Jessica’s palm, and he felt it jump every time she slid her tongue into his ear.  He slid his hands down her body and gripped the firm, rounded globes of her ass in both hands, pulling her off of the shelf and squeezing her ass hard in his hands. 

“You keep that up and I’m gonna cum in my pants,” he gasped as he squeezed Jessica’s ass in his hands. 

“We can’t have that, now can we, my pet?” she whispered breathlessly in his ear as she continued to grip his cock outside of his pants.  “I want you to cum in my mouth, not in your pants,” she said, nipping on his earlobe for emphasis.  She sucked his earlobe into her mouth briefly before placing both hands on his chest and pushing him away from her slightly.  She looked into his eyes, and the moonlight shining on them from behind her showed the fire of desire and lust burning bright in his eyes.  She was quite sure he saw the same thing in her eyes and only paused for a moment before slowly dropping to her knees in front of him.

Jessica looked at the large bulge of Roger’s hard cock pressing against his jeans, and she ran her palm over it before reaching up with both hands and unfastening his jeans.  While she worked at the buttons on his fly Roger pulled off his polo shirt and dropped it on the shelf behind her.  She had his jeans open in a matter of seconds; as usual, Roger wasn’t wearing any underwear, so as soon as she pulled open his jeans his cock sprang out, nearly hitting Jessica on the nose in the process. 

“Oh!” she exclaimed, then she giggled as she wrapped a hand around the throbbing shaft of his fully erect cock.  “I see you’re ready to go!” she said, looking up at him and smiling as she squeezed and tugged on his shaft. 

“You bet I am!” he replied.

“Good!  That’s just the way I want it!” she said, her smile broadening as she pumped his cock again.

Jessica turned her attention to the big, throbbing cock in front of her, and she was pleased to see a large drop of pre-cum forming at the tip.  She squeezed Roger’s cock harder and pumped it again, making the drop get bigger.  Just before it dripped from the tip of his cock Jessica’s tongue shot out and she licked it off; she loved the salty taste of his pre-cum.  She slipped her full, soft lips over the head of his cock and sucked firmly, pumping her hand up and down his shaft at the same time to draw more of the clear fluid from him. 

Roger moaned slightly as she sucked on the head of his cock, and he felt the pre-cum being sucked from his cock.  He looked down and watched as Jessica sucked on him, her lips firmly wrapped around his cock, the head of his cock fully inside her wet, sucking mouth.  She reached up and grasped his big, heavy balls in her other hand, rolling them around in her hand and squeezing them gently as she pulled yet more pre-cum from his shaft.

Jessica had Roger so excited that a steady stream of pre-cum was flowing out of his cock into her mouth, and she felt his cock jump in her hand and her mouth as she gripped his balls with her other hand.  Her pussy was sopping wet by now, her own excitement at a fever pitch, but instead of needing his cock inside her pussy she needed it in her mouth and down her throat instead.  She looked up at Roger, the head of his cock still in her mouth, her hands still on his shaft and balls, and was pleased to see him watching her intently.

‘Time to get serious!’ Jessica thought to herself as she turned her full attention towards Roger’s cock.  She ran her soft, wet tongue along the underside of the head of his cock as it was still buried in her mouth, then ran it around the head several times before she started to slide her mouth down the shaft of his throbbing cock.  Jessica tugged on Roger’s balls as she slid her mouth slowly down the length of his shaft, sliding her tongue along the underside of his cock as she slowly worked more and more of his nine-plus inches into her mouth.  She kept up the suction on his cock, feeling the pre-cum continue to flow out of his shaft.

Roger watched in amazement as Jessica slowly but steadily slid her mouth down the length of his cock, tugging on his balls as she did so.  He was amazed that she was able to maintain the suction on his cock as she swallowed him, but she did – and the feeling was nothing short of amazing!  She had more than half of his shaft in her mouth now and was still going, still slipping her mouth further and further down his length, getting closer and closer to the base of his cock.  He felt the head of his cock nudge the back of her throat, and Jessica never paused for so much as a second as the head of his cock slipped past that point and probed deeper down her throat.  A few moments later Roger was amazed to see Jessica’s mouth pressing against his abdomen as she took the last little bit of his cock into her mouth.  She swallowed around the thick shaft filling her mouth, and Roger jumped as he felt her throat close briefly around the head of his cock.

Jessica was in heaven as she took the last of Roger’s big, thick cock into her mouth and down her throat.  There was a moment when she thought that she wouldn’t be able to do it, but she never hesitated in her efforts to swallow him whole.  And now she had done it!  His entire cock was in her mouth with the head of his cock down her throat, and she paused for a few moments to catch her breath and adjust her breathing around the thick shaft filling her mouth and throat.  She swallowed once and felt Roger’s cock jump as she did so, and she would have smiled if her mouth hadn’t been stuffed full of cock at that moment.

Jessica paused for only a few moments before she began slowly, very slowly, sliding her wet, sucking mouth back up the length of Roger’s shaft, sucking on it all the way.  She ran her tongue along the underside of his cock as she slipped her mouth back up his cock, keeping up the suction the entire way.  She stopped when just the head of his cock was in her mouth, pausing to breathe and run her wet tongue around the head of his cock once before sliding her mouth back down on his shaft again.

Roger watched in amazement as Jessica slid her mouth back down onto his shaft again, the skin of his shaft glistening wet with her saliva in the moonlight.  He wondered how she was able to maintain the suction on his cock and manage to breathe at the same time, but as long as she was able to do so he really didn’t care how she did it.  He watched as she once again took his entire length into her mouth, the head of his cock pushing down into her throat as her nose bumped against his abdomen as she reached bottom.  She gave his balls a firm squeeze before sliding her mouth slowly back up his cock again, slathering her tongue over and around the shaft as she sucked on it hard.  She looked up at him as she slipped her mouth back up his cock, and the look of pleasure in his eyes made her happy.  This made her want him to cum in her mouth even more, and even though her pussy was wet and begging for attention, she focused her entire attentions on Roger’s cock and making him cum.

Jessica fell into a smooth, steady rhythm, sliding her mouth up and down Roger’s cock in steady, even strokes.  She kept up the suction on his cock as she slid her mouth up and down his shaft, massaging and squeezing his balls with both hands now as she gave him a “hands-free” blowjob.  Roger loved seeing her full, soft lips sliding up and down his throbbing shaft, and it was obvious to him that she was enjoying what she was doing to him almost as much as he was enjoying it having done to him. 

She slid her wet, sucking mouth up and down the length of his cock, taking the entire length into her mouth and down her throat with each downward stroke.  Roger’s shaft was glistening with Jessica’s saliva as she deep-throated him over and over again, her head bobbing as she worked on his cock.  Each time she slipped his cock deep into her mouth and down her throat Roger felt his cock bump against the back of her throat, and each time this happened it sent an electric-like shock up his shaft straight to the base of his balls.  Roger knew that he was in the mouth of a true blowjob master, and he also knew that it wouldn’t be long before he was blowing his load down her throat.

Jessica was intent on making Roger cum, and she could tell by the way he jumped each time she deep-throated him and by the increasing tempo of his breathing that it wasn’t going to be long before the big, thick cock she was working on was pumping his cum into her mouth and down her throat.  She increased the intensity of her motions, sucking harder on his cock and pulling more firmly on his balls as she picked up the pace of her mouth sliding up and down on him just a bit. 

Roger was watching Jessica intently as she sucked on his cock, her cheeks hollowing in drastically as she pulled her mouth up the length of his shaft.  This was when the suction on his cock was at its peak, and each time she did it she brought him closer to orgasm.  He felt the first familiar tingling at the base of his nut sack, and he knew it wasn’t going to be long before he came.  The fact that she appeared to be genuinely enjoying herself only made it more erotic and more exciting.  He knew that Jessica was just as turned on as he was, as the scent of her musk had filled the lifeguard house they were in. 

Roger felt his balls shift as the tingling hit him once again, and Jessica felt his balls shift as well.  He was quickly building to orgasm and would be shooting his cum down her throat in a matter of seconds now, and that’s just what she wanted.  She pulled and tugged on his balls a little harder as she increased the suction on his cock, making Roger moan.

“I’m gonna cum!” he moaned, leaning forward and placing his hands on the edge of the shelf Jessica had been leaning against for support.  Jessica continued working on his cock without pause, sucking as hard as she could while tugging on his balls with both hands.  His cock was literally dripping with her saliva by now, running down her chin and dripping onto her breasts as she worked his cock over.

Then she felt his cock widen in her mouth and knew that Roger was about to cum.  A split second later Roger moaned loudly as his cock erupted, the first stream of cum racing up his shaft and blasting out of the tip of his cock and straight down Jessica’s throat.  Jessica flinched as the first blast of hot, thick cum hit the back of her throat, but she never stopped her efforts.  She released Roger’s balls from her hands and reached around to grab the back of his legs, pulling him towards her and holding him in place and in her mouth as his cock pumped again and again.  She drove her mouth all the way down onto his cock, forcing the head of his pumping, spewing cock past the back of her throat, and held her breath as his cock shot stream after stream of cum into her mouth and down her throat. 

Roger gritted his teeth and groaned with the intensity of his orgasm, gripping the edge of the shelf firmly as his cock emptied itself into Jessica’s wet, sucking mouth.  He felt her swallow around his cock and looked down just in time to see a very small amount of cum slip out of the corner of her mouth.  She swallowed the rest of his huge load with no problem, keeping her mouth clamped around his cock at it throbbed and pulsated again and again, his balls draining themselves into her wet, waiting mouth.

‘My God, he’s cumming buckets!’ Jessica thought to herself as Roger’s cock continued to pump its load into her throat.  She hung on to the back of his legs, keeping his cock buried in her mouth and maintaining the suction until she finally felt the pulsing of his cock begin to slow.  Roger’s legs were trembling as his orgasm finally slowed, and he jumped as Jessica swallowed around his cock again.  When she felt his orgasm slowing Jessica slowly slid her mouth back up the length of Roger’s cock until just the head was in her mouth, and she sucked as hard as she could as the last bit of his cum spit out of his cock and onto her tongue.  She released the head of his cock from her mouth with a loud ‘pop!’ and then sat back on her thighs, releasing her grip on his legs as she sat back on her thighs.  She looked up at him and opened her mouth, showing Roger the last of his cum resting on her tongue.  She closed her mouth and swallowed, still looking into his eyes, then licked her lips and smiled at him.

“Mmmm, delicious!” she said, her green eyes sparkling in the moonlight.  She had left Roger panting and gasping for breath, leaning against the shelf for support, his jeans down around his ankles, droplets of sweat on his forehead. 

“Holy crap!” he said, gasping as he tried to catch his breath.  “I don’t think I’ve ever cum that hard from a blowjob before!” he said, and Jessica’s smile broadened at this.

“That’s because you’ve never had one of my special blowjobs before, my pet,” she said.  “And I can promise you that it won’t be your last, either,” she continued.

“But what about you, Jessica?” Roger asked.  “You need to cum, too, right?”

“Yes, my pet, I do,” Jessica said as she got to her feet, standing up between his outstretched arms.  Roger could see the streams of her saliva glistening on her breasts as they rose and fell with her breathing. “And as soon as we get back to the hotel I’m going to lay you down on the bed and ride your lips and tongue until I cum all over your face!” she said, wrapping her arms around his neck as she spoke.  Then she gave him a quick, soft kiss on the lips before continuing.

“Unless you can get hard again and want to use that big, wonderful cock of yours on me instead, that is!  What do you think, my pet?” she asked in a low voice.

“I think we need to get back to the hotel and find out,” Roger replied.

“Then pull up your pants, my pet, and let’s go!” Jessica said, giving him an impish, slightly evil grin as she ducked under his arm and started walking towards the door.

“Your wish is my command!” Roger said, quickly reaching down and pulling up his pants, nearly tripping over them as he hurried to follow her.

To be continued…