Diving with Jessica Ch. 02

After watching the erotic, kinky show for a while you cough, making your presence known. Her smile widens, otherwise there is no reaction of her. She keeps masturbating anally her other hand brushes a few loose strands of her behind her ear.

"Found something?" she finally asks.

"Yeah!" you answer proudly, lifting the tube, even though her eyes are closed, "KY! The Cadillac among the lubricants!"

"That's awesome!" she replies, her eyes still shut, her fingers still pressing into her ass, "I took the liberty to start without you! Come around the bed, big boy!"

You walk around the bed until your erection is bobbing inches away from her face. Finally she opens her eyes and reaches for your dick with her free hand.

"Gimme some!" she orders, removing her fingers from her ass and holds her palm open for you before going down on your cock, taking it deep in her mouth and getting it wet with her saliva.

Hastily you unscrew the tube and squeeze a generous amount into her palm and watch as she rubs her hands together to spread the cool gel out, then wraps them around the base of your cock, the sensation eliciting a sharp intake of breath from you, and massages it into the parts that her mouth isn't currently servicing.

You moan at the sloppy blowjob she is giving you and have to take a couple of deep breaths to focus your attention again on the task at hand. You squirt a large portion of jelly into your palm, then you throw the tube carelessly away.

Leaning forward you take a glob of gel out of your hand with your fingers and apply a thick coating onto the soft, brownish skin around her asshole. Carefully you work it in, always working towards the puckered opening in the center, massaging it in and getting a good layer of lubricant on her rosebud.

As soon as you're satisfied with it you scoop the rest of the jelly out of your palm and begin to push it inside her butt. Her bowels have to be lubed up, too and so you begin to use your fingers to embrocate the inner parts of her ass thoroughly.

Meanwhile Jessica is done with your dick. She quit using her mouth a while ago and now she uses both hands to spread the lube over your whole shaft, paying special attention to your bell-shaped head until she finally gives it a Finished-kiss.

"I'm done here," she moans, your treatment of her ass already got her rolling again. Her voice is a little shaky as she asks the determining question: "You wanna start?"

You look down at her, your fingers carefully slipping out of her relaxed butthole. Slowly you kneel down in front of her until your faces are level, gently take her face into your hands and place a soft kiss on her forehead. "Don't worry!" you whisper, "You'll love it!"

She gives you a weak half-smile and answers, "Just please start gentle! It's been years!"

You smile soothingly, then you straighten up, walk around her and get on your knees on the bed. Slowly you shuffle forwards until you're kneeling between her spread thighs. When you look up you can see the reflection of Jessica's face in the mirror. You're going to take her expressions as an indicator on how to proceed.

After taking a couple of deep breaths you begin. You reach forward with your left hand and grab her buttock to spread her ass-crack. With your right you grab your cock around the base and guide it up until it is placed against her asshole, lining yourself up.

"Ready?" you ask, your heart beating about a million times a minute.

"Just do it already!" Jessica growls, her voice muffled by the cushion she bit down on. Her hands have reached forward and now she tightly grips the edges of the same cushion to brace herself against what is coming.

Slowly you start to apply some pressure, careful, not wanting to act hastily. At first you think nothing is going to happen, but then you feel Jessica's sphincter widen and give way to your cock. Jess squeezes her eyes shut, whimpers audibly into the pillow and her knuckles turn white as your helmet pops past the closing muscle and gets swallowed by her ass.

You pause for a second, gritting your teeth as you face the incredible tightness of Jessica Alba's butt, then you push forward, taking care to be as gentle and cautious as possible. Slowly you manage to sink another three inches within Jessica's smooth ass.

"Halfway there, beautiful," you whisper and look into the mirror. Jessica looks agonized. Her teeth are grit and tears have formed in the corners of her eyes because she snapped them shut so hard.

"You okay?"

"Oh, I'm awesome, thanks for asking!" Jessica gasps out, sarcastically, as she tries not to clench her sublime ass with your cock shoved up there...

Taking her sarcasm as a good sign, you focus on the task again. It takes another two careful thrusts, but finally your groin is pressed firmly against her buttocks and your dick is buried all the way inside her rectum, your ballsack laying snugly against her wet pussy-lips.

"Goddammit, baby," you breath looking down at how wonderful your cock looks buried in Jessica's smooth round ass; you then pat her ass-cheeks comfortingly as you enjoy the massaging contractions of the strong muscles of Jessica's booty. Her pussy felt like heaven, tight and warm, but her asshole bests that in every aspect. You feel like you're going to burst with joy from the combined sensations- the firm grip of her butt and the incredible ego-boost of having sodomized Jessica Alba, a fucking big-time Hollywood-star.

Jessica meanwhile pants heavily as she tries to handle the situation and you give her time to get accustomed to you. After all, you want her to enjoy this session and you have as much time as you need...

After a while she calms a little bit. She opens her eyes and looks at you through the mirror. Her gaze is wary with nervousness and her face is flushed red, beads of sweat run down her brow and there are streaks of tears. In a strange way, she has never looked more beautiful to you.

"Okay," she whispers in a shaky voice and swallows hard before giving you her permission, "I'm ready..."

You nod, then you slowly begin to move your hips back and forth, always pulling your cock just a little out before pushing it back in, all the while carefully watching Jess' reactions. She huffs hard and at first her face still contorts with pain every time you thrust in, but soon the pain seems to fade away and she finds pleasure in the gentle anal stimulation.

After a while little moans of delight escape her lips as she manages to relax more and more. Her grip on the pillow eases and she turns her head to the side, resting her cheek on the soft cushion.

"H-harder..." she urges you, and you are happy to oblige, increasing the length and speed of your thrusts. The KY does the trick perfectly and you manage to pull your dick out half way every time and shove it back in smoothly, your pelvis slapping against her bum every time.

Grabbing her hips, you're pulling her up into a new position that presents her ass in a submissive way while her head still rests on the bed. This allows you a deeper penetration of her asshole and Jessica's moans turn into yelps of pleasure as you continuously pick up speed. She asked you to fuck her like a bitch, so you won't deny the lady such a wish.

Reaching forward you grab Jessica's right wrist tightly and guide her hand down to her pussy.

"Touch yourself, Jess," you snap through clenched teeth, your dominant side getting the better of you, "Finger your cunt, you little slut!"

You can hear wet, squelching sounds as she energetically begins to rub her pussy while her free left hand travels up to fondle her tits.

From time to time you pull your dick out of her ass completely and enjoy the sight of Jessica Alba's gaping asshole. For a girl with such a tight ass who gets sodomized at such an unregular basis she manages an impressive gape...

You're now pumping into Jessica's ass as fast as you can and she seems to be on a completely different level of pleasure, her screams fill the room along with your grunts and the slapping of your groin against her ass. Ahab said the cabins were soundproof, but you wouldn't be surprised if everyone on the boat had heard the two of you by now...

You can feel Jessica tense up a little and notice a few things: her breath becomes unnaturally short, her brow furrows and her sphincter clenches spastically... all of those are signs that Jess is about to tumble over the edge and experience a monster orgasm.

Yet you decide to be cruel, using your dominant position to show off the power you have over her. Never missing a beat you lift your hand and bring it down in a stinging spank.

"Don't you dare to cum without permission!" you growl, emphasizing the threat with another couple of heavy-handed smacks that make her ass jiggle and soon her buttocks glow in a bright shade of red.

Jessica squeals with frustration, then she bites down on the sheets once again to master the control over her urges.

Grinning manically you change the position again, getting up to your feet so that you're now squatting behind Jessica's ass while holding on to her hips. The new, better angle allows you deeper, faster thrusts and you take extensive advantage of that fact.

Jessica had let go of her clit a while ago, she couldn't handle that much stimulation now, instead she reaches back with both hands and grabs her buttocks. Spreading them apart as far as possible allows you to watch how her sphincter stretches tightly around the base of your dick and you can penetrate her ass even deeper.

You reward her initiative with a last hard spank, then you lean forward, grab her by her tussled curls and roughly lift her head up.

"Cum!" you hiss into her ear.

Jessica lets go of all control of her body; sighing in a yearning way. Her eyes roll into the back of her head and she sucks air in until her ribcage is almost bursting. Her feet are kicking against the mattress uncontrollably and her neatly polished fingernails dig deep into her butt-cheeks. Then she lets out a long, guttural, almost inhuman scream. Her sphincter clamps down on your cock, locking it in place. Her vagina spasms, then a long, thick shot of girl-cum shoots out of her cunny-tunnel and soaks the sheets of her bed.

You watch in awe as the beautiful Hollywood-star turns into a madwoman right beneath you. A sight- a feeling- you'll remember for the rest of your life, as her ass milks your cock for all it is worth.

When she finally relaxes her ring muscle enough for you to slip out you hurry to get around her. Kneeling in front of her you grab her by the hair with your left hand and lift her head up while you frantically jerk yourself off with your right, aiming at her beautiful, sweat-soaked face. Jessica is too out of it to notice that you want to finish your intense session with a crowning finale.

You don't last five seconds before you tense up with a growl and your load shoots out of your dick. Carefully aiming you plaster first her left, then her right eye shut, then you aim your next four shots over her cheeks and the bridge of her nose before you push your member between her lips and let the last, weaker strings of cum flood into her mouth while she feebly sucks on your dick, apparently not caring that it was balls-deep in her ass moments before.

After she swallowed the last droplets of your load you pull your spent dick out of her mouth and let go of her hair. Her head slumps down onto the bed and she stays in that position with her ass high in the air, her well-fucked holes on display, too tired to move.

Gently you sweep a curly strand of hair that was stuck in the cum behind her ear and give her a light kiss on the sweat-drenched forehead.

"I'll let you rest... See you tomorrow, my little buttslut," you chuckle and you can make out a weak, satisfied smile on her face.

Quickly you get up from the bed and pick up your shorts and the ruined remnants of your shirt, then you hurry to the door. Just as you are about to slip out you turn around for a last look. Jessica is facing away from the door and everyone who would come in to check on her would be greeted by the sight of her upraised butt with her twitching asshole and drenched little pussy, dripping with her cum.

You can't resist and quickly pull your cell phone out of the pocket of your chinos to take a snap of the inviting sight. Jessica didn't notice and anyone who'd stumble over it wouldn't be able to make out the girl's identity(and even if they could, they'd never believe it, they'd think it was one of those nude celeb fakes floating around on the net), so you can't see a problem with that...

Quickly you close the door, hanging a "Do not Disturb"-sign to the knob- just to be sure- before rushing into your cabin for a shower, grinning like a kid on Christmas.

-

Half an hour later you sit in the saloon, freshly showered, drinking a victory-beer as Jason sits on the bar-stool next to you, his eyes fixed on the display of your iPod.

"I can't believe it," he utters finally as the video ends with a zoom-in of Jessica's cum covered face.

"If it helps you, neither can I," you answer as you take the device out of his hand and take a big swig of your bottle, "The little sonofabitch wanted to blackmail her into sex using this!"

"What a little rat!" Jason growls, "I guess you prevented that? Anyway, you won! Fair and square! So here she goes..."

With that he fishes the keys of his Harley out of his breast pocket, places it on the bar and, after a moment of solemn grief, slides it over to you.

With relish you finish your beer, then you place the empty bottle on the bar.

"Keep them, bro," you smile, "I got enough prices with this bet!"

He looks at you surprised as you get up and slap him amiably on the shoulder. "I gotta go get some sleep, man. Had some serious activity over the last couple of days..."

You turn towards Ahab, who serves behind the bar like every night. "Good night, buddy! Bring my friend here another beer, please. He just won a Harley!"

"Yeah, son," the old captain replies while drying of a glass, "Get some good rest because tomorrow we'll get the opportunity for a little walk on this beautiful little island! We'll see caves and little lakes and waterfalls and the most stunning beaches you'll ever see!"

"Sounds great," you smile and give him a quick salute.

With that you leave the saloon and stroll down to your cabin, your chest swelled with pride of the events of the last couple of days, your mind already all over the opportunities of the next day...