Something Better Ch. 03

Any tenseness to his body faded quickly, only to be replaced by this sweet, soothing sensation that dripped small droplets of fuel onto the embers of arousal growing in his loins. Casey was horny enough to begin with, but her touches were starting to make his cock leak. In addition to her fucking glorious tits that hung beneath her whenever she leaned over him to work the lotion in. His chest rose and fell with shallowing breaths, he could feel his prick twitching with excitement. Even more so as she crawled further down, applying more liquid onto her hands and dabbling some helpings of it on his bare thighs, then resumed rubbing it in down his legs.

"Uuhhn..." Involuntarily the moan escaped Casey before he could hold it back. Her feminine hands just seemed to know every correct spot to touch in order to make him quiver. His inner thighs were laced with sensitive nerves that seemed to be wired directly to his prick, he was sure there was a small leak of precum dripping down him down.

Gabbi didn't comment or say anything flirtatious, she just smirked and resumed massaging his upper, then lower legs. All the way down to his feet she went, picking them up and rubbing the oil in, squeezing his toes and alternating between both feet. She was very thorough in her work and left no stone unturned.

Except...she hadn't touched his cock.

He only noticed this now as he had been so wrapped up in her nakedness and the general incredibly good sensations running all over wherever she touched. But as he grew hornier and hornier, he finally seemed to realize that she had skipped over his erect penis entirely. Massaging all around it, but not even giving it a casual caress.

"Why didn't she...?" Casey thought confused, and a little desperate. Ever since the movie theater, he looooonged for her to touch him there again. And the key to his fantasies coming true were right there, only inches away as her hands ran up his form again. Fingers splayed out and palms down on his slippery flesh, sliding up his legs, passed his thighs...passed his cock, and back over his belly to his chest and nipples again.

Casey bit his lip, "Nnf...Gabbi..." He lifted his hand and reached for his cock, intending to stroke it and hoping that she would get the message. Outright asking for her to jerk him again might have been a little too embarrassing to ask.

But to his surprise, just as he felt his fingertips touch the base of his hard member, he felt Gabbi's hand give them a quick playful slap. He jumped from this and looked back up to her face, her eyes staring at him with a knowing and slightly snarky smirk that she'd given him before.

Then her index finger was lifted up in front of him, and she waved it back and forth, followed by shaking her head slowly 'no.' "Mmm mmm..." Was all she offered him, but Casey understood. He wasn't allowed to touch his cock. At least just for right now, as she had gladly encouraged him to jerk off before. So today she must've planned on shaking things up. "Not tonight baby...now...turn over..."

His heart skipped a beat when he heard that, "On...on my stomach?" He asked cautiously.

Gabbi's smile grew into and almost evil one and she quirked an eyebrow just for a moment before shaking her head again. "On all fours Casey..."

"Oh God..." Nerves were building up again, he swallowed hard and he felt his adrenaline going hard. But he nodded, "O-okay..." His hands shaking, he lifted himself up, and carefully flipped his body over.

Moving into an even more humiliating position, doggy style. A very common position for normal and...anal sex.

He put his hands flat down on the bed, and got situated on his knees. Risking a glance over at Gabbi's waist where he knew the 'key' to his virginity was, and just as he suspected...

It had grown to its full size, fucking huge and thick. Hard between her legs as she clearly got just as aroused as he had during his massage.

Now that he was looking at it again, he almost felt his heart wanting to burst at how big it was. Surely it wasn't that big before, right? ...Right?? Why did it feel like it was the biggest dick in the universe now?

He blew air out from pursed lips and stared back down at the blankets, he could feel his dangling cock still stiff and ready. Practically a fear boner at this stage as reality started to set in.

Thankfully though, as Gabbi sat up on her knees, she didn't move behind him, she just leaned over him and squirted more oil on his back. Then started to rub it in there too, his massage was not done yet apparently.

"Wait was she...was she just fucking with me?" He turned his head to look at her, a cocky smile on her lips. She looked back down at him and gave him a quick wink. "Ugh, this woman is the death of me." His head fell back down now realizing that she was just teasing him.

Gabbi was still going to fuck his fucking brains out of course, but not until his massage was done.

Regardless of her toying, her hands continued rubbing all up and down his back. Applying pressure with her thumbs and swirling them along the sides of his spine, she could feel he was still tense and did her best to coax the tension out of him. Moving her hands to his lower back and almost audibly going 'aww' as she noticed he had two cute little dimples there. Right above the swell of his ass on the love handles.

"Perfect to rest my thumbs in while I'm railing you." She thought deviously.

She skipped over his butt intending to save the best for last, and went down to the back of his legs. Starting at his calves, and gingerly moving upward, reupping her oil whenever she felt she needed more. Leaving Casey feeling slippery all over, and a little frustrated.

When she got to the back of his thighs, it was pure torture. Her digits kept getting so damn close to his cock and balls, but never touching it. "Urrrggh..." He moaned again, but it had a little rasp to it. And Gabbi again felt her ego swell as she heard the frustration in his voice. She was turning him on like crazy, and the evidence as both in his voice, and in the swinging string of sticky precum that leaked down from his little tip.

"Veeery excited I see. Excellent..." After intentionally taking some time on the back of his thighs, she finally moved up to her favorite part.

It was time for that ass of his.

She picked up the bottle and held it high above his booty, intentionally drizzling it from a dramatically high point like they do in porn. Then set it back down to get in there with her hands, not being too graceful about it. She palmed both of his pillowy cheeks and gave them the most delicious squeeze she could.

Casey jumped, his head flinching upwards and his eyes opening wide again as he felt her giving his bottom the attention. Working the oil in all over it, making it shine with the fluid and toying with the bubble butt. Wiggling one cheek in her hand before rubbing the oil in a circle, rotating his cheeks around and squeezing them. Loving how the flesh squished between her fingers. Such a big butt for a boy his size, it had to be destiny.

There was no way such a perfect ass could be sculpted like this, and then not get fucked day in and day out. This needed to happen, Gabbi's erect cock was aching for it, she was also dripping clear pre-seminal fluid with how horny she was. She wanted to just stick it in now, but wasn't finished juuust yet.

"Okay Casey...this feel good?" She asked, still massaging his butt, squeezing and playing with it to her hearts content. Pulling apart the cheeks and looking between the valley of his ass, finally spotting the tiny star he had hidden from her for far too long. "Fuuuuck yes, there it is..." She thought looking at it, his little love hole. It looked so small, and so tight, it would be a miracle if she could fit.

He nodded, trying to glance back over at her beyond his longish black hair, "Mhm, yeah it really does."

"Good...now. This might feel a little strange at first...but relax, I promise you'll like it." She gave him a heads up, licking her lips.

"Wh-what will? Ahh!" He yelped, flinching again as he suddenly felt a warm, slippery appendage suddenly start sliding up and around his asshole. He looked all the way back over his shoulder to see Gabbi's eyes staring at him behind his rear, but the rest of her face was buried between his cheeks, French kissing his star.

Another warmth spread out inside him, but different from the warmth the oil provided. This was a new, and strange sensation that swam through him in a rush and brought a chill to his spine. Gabbi swirled her tongue around the pretty clamped shut hole, gently trying to weaken it's resolve so that she may go inside and taste his innocence.

She smacked her lips against it a few times, kissing his love hole tenderly like it was Casey's lips. Poking her tongue out and giving it good long licks up and down, slathering it up with her saliva rather than the oil. And to her surprise, he seemed to relax quickly, maybe due to the entire massage but regardless, she felt his barrier weaken.

Casey's breath shuddered, and he stared into the mattress, fists gripping the mat tightly. Her tongue's moistness and intimate skills felt so...naughty.

"..Aaaahhaaaaaa..." He breathed out, then closed his eyes and let his lips part wider. "Aaaaaaahhhhh..." The first sound was a little nervous, but the second moan, there was no denying the pleasure it was laced with.

This was noted by Gabbi as she felt his sphincter unclench, and using the opportunity, she pushed her tongue firmly against his entrance. Quickly breeching it, and dipping inside, tasting cute little Casey's most sacred place. "Mmmmm..." She moaned, vibrating his lower body with the sound.

He felt her tongue enter him, quickly wriggling its way inside and looking around, making itself a home in his tight depths. More rushing sensations radiated throughout his body and Casey felt himself push his butt back into her face on reflex. "Ooohh...aah." He moaned a little more freely now, relaxing into the thrilling waves coursing through him. All the little nerves around that area were gladly responding to the attention, his muscles squeezed around Gabbi's tongue practically trying to pull the appendage deeper inside. Her lips also continued to smooch all over his entrance, literally making out with his hole and dipping her tongue into him every chance she got.

"Fucking fuuuuck he tastes so good." She thought, greedily lapping at the sweet taste he sported. It was unlike anything she'd ever had before. Her cock however was getting very jealous of her tongue and it ached more and more trying to send signals to her brain that it wanted to get up in there.

But not yet, he needed to be prepped first.

With a wet smack of her lips, she gave his puckered hole a few more sloppy kisses before leaning back and picking up the massage oil once again, this time drippling the lotion directly onto his entrance. Casey squeaked from the coolness of it at first, but then cooed as it quickly warmed to him, and was completely unaware of Gabbi soaking her middle and index fingers in the oil as well.

She ran them over the dab of oil, smearing it all over the star and coating her digits in it too. She could see Casey's toes curling and uncurling as she did this and the string of precum from his dick grew thicker until it couldn't support its own weight and broke off into a smaller one. His arousal was key, she wanted his first time to be incredible. Anything to ease him up and into this giant step in their relationship.

And hear was the moment of truth, carefully with her middle finger only, she drew small circles in the center of his star. Applying a tiny bit of pressure, relaxing, then repeating a little harder, pushing only centimeters of her finger in for a few seconds to open him up.

Then with a bite of her own lip, she pushed it in.

Sliding smoothly through his weakened passage passed the first knuckle, then the second and stopping halfway to the third.

Casey's jaw dropped in a silent gasp, he felt the cool sensation of the oil entering him, but it was not alone. It was carried in by a small invader, pushing through his gates and inside of him. It didn't take a genius to realize what she did, she was fingering him.

He was very surprised that he didn't feel any pain...at all. Just a slightly strange popping feeling almost. Or rather an opening sensation down below, he could feel her finger squirming about inside of him. Lathering up his insides with the oil to lube him up for the main event that was surely to come.

Carefully, she pulled her digit back out to the first knuckle, then pushed it back in. This time going all the way down to her third knuckle, and curling her finger when it was all the way in.

The boy's baby blue's closed and his lips remained parted from the swimming sensations in his loins. Quiet gasps and unexpected pleasure gently crawling up and down his form, it was foreign and strange receiving these feelings from his butt. However, that didn't mean he was rejecting them, in fact, he felt his lower half once again push backwards on reflex, seemingly wanting more.

"Is that okay baby?" Gabbi asked, he seemed to be handling it well, but she just wanted to make sure and hear it from him.

He nodded, "Uh huh..."

She continued this gentle sawing motion with her finger, twisting it around and curling it at every angle, hoping she would find his P-spot. Then the real fun could start.

But during this, she seamlessly integrated her middle finger into the penetration as well. On one of the push ins, she added the second digit, cautiously wriggling it inside the slicked-up entrance and gaining access to his hole with now the both of her fingers.

That time Casey felt the slightest stretching of his ass, but again, it wasn't painful. It was pleasant, he was so lubed up that there was very minimal effort on his anal muscles part to have to accommodate her intrusions. They were able to easily slip inside his tight passage and playfully dance about inside him.

"Ooouuuu..." He moaned again, lowering his upper body a bit and leaning on his elbows. Not having much upper body strength to keep him in the doggy position for so long, he opted to go face down, ass up. Practically full on presenting himself now, but he didn't care, the soothing and sweet feelings she was delivering with her attention was relaxing and exciting him to no end. The urge to touch his cock was unbearable, it twitched and drooled his precum, but she said no touching it, so he did his best to oblige.

Suddenly there was an intense jolt of electricity that rocketed up his body, surging into his cock and up his spine. Casey let out a sharp gasp and gripped the mat tightly, Gabbi's fingers curled downward and had just the right position and thickness with her two digits to touch the tiny, walnut sized gland in his rectum that created the sudden blast of bliss.

"Ohhh there it is..." Gabbi whispered huskily. Sticking her fingers in deeply, as deep as her hand would allow and wiggled them along his special spot.

Immediately Casey started to mewl and squirm, "Mmm, aah...oh...oh Gabbi...oh my God..." His words were breathless, the sudden pumping she did and shocks of delight were setting his body on fire. His cock now crying under him, and oddly enough it felt so good that Casey believed if she kept doing that...he might be able to cum.

Never in his life did he have a no hands orgasm, but just judging by the feelings she gave him when she prodded him there. It felt as if he could actually reach an orgasm that way with enough attention and focus on it. His breath making the mat by his face hot, and his knuckles turning white where they held the crumpled material.

"Okay, I can't take this anymore, and I think he's ready..." Gabbi thought, unable to handle the nearly painful throbbing of her womanhood any longer. She was rock solid, veins bulging and angry, hungry for this boys ass, and the way it welcomed her fingers and tongue, she knew his innocent little hole was hungry for her too.

It was time to feed them both.

Gabbi leaned up, giving a few more quick strokes with her fingers inside, before pulling them out to reach one last time for the lube.

Casey made a noticeable whine as she extracted her digits, "Nnng, Gabbiii..." He glanced back again, only to see her applying the oil to her cock.

The situation just got very real.

"It's time baby..." She worked the lubricant all over her meaty shaft, rubbing it all over her dick. Applying it over her tip, jerking her cock with it a few times and then squirting a little more directly onto his hole.

Casey gulped, "Oh...okay..."

She dropped the oils and placed her hand on his lower back, "I promise you I'll go as slow as you want. It might hurt at first, but just keep relaxed, and it'll feel amazing. Much better than what my fingers could do honey." Her voice was calming, careful and genuine, she didn't want to hurt him, no matter how badly her cock hurt.

He nodded, his doe eyes blinking a few times and he blew air from his lips again. Heart accelerating, "Okay...I'm ready."

Gabbi climbed high up on her knees behind him, stroking her dick a few more times, lube mixing in with her precum and making it extra slippery. Oh was she ready for this, she had been waiting for this for weeks now. Eager to finally sink herself balls deep in this boy pussy, but she would show restraint and not lose her shit. Again, she wanted his first time to be nice and memorable. Not awkward and painful like most first times unfortunately were.

She placed the shaft of her cock between his cheeks, and hot dogged it a few times. Running her length up and down his crack, teasing it and mixing the lube even more. The heat of her womanhood almost startling Casey, he'd felt it before but not in such a tender area.

Then, she took hold of her dick, angling it downward, tip aimed directly at his love hole. "Alright baby...here it comes..."

The final shaky breath was drawn in hotly from both parties, ready to finally do it. After all the flirting, teasing, sexting, it was time for them to become one.

Her head pressed against the oiled-up entrance and Casey gripped the mat with renewed strength, her mushroom shaped tip prodding him, asking permission to enter. Gabbi felt him tense up, but all it took was some more pushing in a little, and pulling back out a little like she did with her fingers for him to relax again.

She held her breath, and pushed down on her dick, feeling his asshole slowly giving way. "Nnnng..." Casey squealed, the anticipation killing him, he could feel it pushing. The pressure getting harder...and harder...and harder before finally...

The opening sensation he felt from before was quadrupled in intensity as his anal ring gave in to her cock. Allowing the intruder to break inside, and slide along his slippery insides, parting the muscles as her dick sank into him a few inches. His asshole popping open, and Gabbi penetrating him for the first time.

The first time together.

His jaw hanging open, eyes wide open, and asshole pulled open. Casey felt his muscles stretch, an achy almost burning sensation from his first time accommodating something so large. He could feel the shape of her tip, the lines of her veins, his passage quickly clamping down on her and squeezing every inch that entered.

Carefully Gabbi guided in her length, pushing inch after inch of her meat into his tight love hole. Slowly...oh so slowly.

The intense heat of his body enraptured her, her own lips were parted and her vocal chords were fighting the urge to moan. But she was concentrating, she wanted to enter him fully. Carefully rocking her hips after every few inches to help his inner muscles adjust to the invasion. But her dreams and fantasies were wrong about how good his ass was going to feel.