Shy Ronny Pt. 02 - Beach Date

As she spoke, she tossed his stained shorts towards her bag and straddled him, grinding herself along the length of him as she leaned forward, hiding most of his erection with her body. She worked the rest of the sunscreen into his front, once again enjoying the feel of his muscles, her pussy throbbing as she ground herself against him, trying to remember if he felt this big before, and cursing her bet with Lexi under her breath. Eventually, she had worked every drop of sunscreen into his skin and was worried one or both of them might pop if she kept up her grinding. Instead, she stood, admiring how every inch of him was outlined against the fabric of his suit before he rolled over, grunting a bit as he hid himself against the sand.

Amanda giggled, moving to her picnic basket and fishing out the sandwiches, snacks, and swamp juice she had packed, laying down next to him, and setting the food within easy reach of them both. For a time, they just chatted, getting to know one another. She learned he worked as a mechanic, played football in HS, and was generally as big a nerd as she thought he might be. They enjoyed their sandwiches, and she laughed at him once more when he realized the drinks were alcoholic. "Just relax, silly," she teased him, "You gotta relax a little."

For his part, Ron just enjoyed her company, she was fun to talk to, and he found himself sharing more about himself then he almost ever did. He had always been painfully shy, bigger than everyone else since forever, and worried about hurting folks, so he stayed quiet, careful, and slow. All the attention from someone like Amanda was almost overwhelming, but he had to admit to himself he was enjoying it. With a bit of a buzz on from the drinks, and after sufficient time to digest their lunch, he happily agreed when she suggested they go cool off with a dip in the lake. It was only when he stood up that he realized he did still have one rather large problem.

"Um... Amanda..." he trailed off, looking around the beach, which had started to fill up while they were eating, and then down to the still very prominent bulge in the thin trunks he wore. She giggled, just grabbing his hand and tugging him toward the water. He resisted for a moment, but standing up, he was already exposed, and the water was the closest place he could hide, so he just let her tow him to the beach, trying to ignore the shocked, or admiring glances being thrown his way from some of the other beachgoers.

"Just relax, big boy. Someone your size has nothing to be embarrassed about, you should be happy for a chance to show off that big package." Amanda teased him as the hit the water together, wading out and heading for the deeper, and still mostly empty adults only end of the lake's swim area. As the water got deeper, Ronny relaxed as his "package" was once again out of sight, though he was soon distracted by the sight of Amanda's ample assets, bobbing enticingly in the small lake waves. Following his glance, she giggled, putting her arms together and pressing offering him an even more impressive view. "I bet you wish you could paint these with more than just sunscreen, huh?" She teased him, one foot flicking out under the water and unerringly tracing the bulge of his erection.

"Amanda... um..." Ron stuttered, embarrassment making his face flame as he looked around, ensuring no one else was particularly close to them. He looked down and realized that the water was just dark enough he could not see what her foot was doing, just feeling her rubbing along his shaft. "There are all those people... back there." He pointed back toward the beach, feeling incredibly exposed with the buxom girl floating before him. When she made no move to stop, her foot idly tracing him from root to head, he realized he was about to have another problem. "If.. if you keep that up.. um..." He trailed off once more, looking down into the water and biting his lip.

"Oh don't worry, Ronny," Amanda teased him, sliding closer to him and, wrapping one arm around his neck, carefully turning him around to face away from the beach, putting his broad back between the other beach goers and herself. Her other hand slipped down, working under his trunks to wrap around his thick shaft, once again finding it hard to believe how little of it she could grip. "I remember you're a bit of a quick trigger on the first pass, but that could be a good thing. I used to be a lifeguard, and on the swim team... but I can still only hold my breath for so long." With a wink, and a deep breath, she let go of his neck, and splashed back into the water, pulling herself down even as she pulled his cock out of his trucks, letting it bob free in the warm water.

Ron could only gasp in shock as he felt her mouth press against the head, her hair spreading out in the water, hiding whatever else she might be doing from his view. He failed to hold back a groan as her warm, wet lips spread as far as they could, trying unsuccessfully to take his head into her mouth. As if realizing he was too big to swallow, she settled for sucking on what parts of him she could, both hands working the rest of his shaft, as if trying to milk him into her waiting mouth. Her tongue swirled around the head, and even teased his cock slit, making him stiffen at the unfamiliar sensations. After all her teasing though lunch, he felt his balls tighten, and before he could stop himself, the first thick shot of his load was pouring into her waiting mouth. He expected her to pull away in shock or disgust, but instead, she held herself in place, continuing to stroke his cock as he unloaded shot after shot into her, wondering if her cheeks were swollen, or if she was swallowing. Eventually, he got his answer, as she detached herself from his cock as his last few shots came free, bursting back to the surface to take in a gulp of air, not a trace of his load to be found, save for a few strands that quickly disappeared into the waves.

"Mmm fuck," Amanda gasped out, licking her lips and running her tongue along her teeth. "You don't taste half bad, big boy... though you have got to stop letting yourself get so pent up like that... not fair to drown a girl." She giggled as he tried to stammer out an apology, pressing one finger to his lips to shush him as she reached down, carefully tucking his softening dick back into his trunks. "There... now that you can be at least semi decent in public for a while, let's go take a walk, OK?" Wrapping her arms around his neck, and her legs around his waist, she rode him piggy back out of the water, and back to their blanket, dropping off and toweling them both off, before packing away the remains of the lunch, slipping back into her coverup and wiggling her feet into her sandals before packing away the blanket as well. "Come on, they have some nice walking trails back in the forest where it will be more private. I think we have both had enough sun, huh?"

Ron slipped his shirt back on, though he chose not to put his shorts back on over his still-dripping trunks, and was happy to follow along when Amanda slipped her hand into his, and set off at a casual pace towards the tree line, letting him carry the bags in his other hand. They chatted a bit, she told him more about her time as a lifeguard at this very lake, keeping things light as they disappeared down a shaded forest path. After about thirty minutes of walking, Amanda leading the way, she suddenly tugged Ronny off the path, leading him through the brush, until they came out in a small clearing.

"here we are!" Amanda cheered happily, tugging him into the center of the clearing. "Nice and private. This was my favorite place to come with my old boyfriend." She paused for a moment, seeing Ron's puzzled expression. "It's far off the main trails, the ground is soft, and the trees will block off a lot of sound... so it's the perfect place for you to fuck me up the ass again, big boy!" Ron's jaw dropped, evidently not realizing there was more to their date then beach going and a quick underwater BJ. "I have been dreaming of that monster cock of yours since the last time, Ronny, and if you think you're taking me home without working every last inch up my backdoor again, you're dreaming." She wiggled out of her coverup as she spoke, tossing it into one bag and she pulled the blanket back out of the other, along with the bottle of lube.

Spreading the blanket, she turned to face the still stunned Ron, rolling her eyes. "Come ON... less drooling, more lubing!" Tugging the bags out of his hand, she set them aside, and lead him onto the blanket, pulling him down next to her as she wiggled out of her barely there bikini bottoms, letting Ron see she was, indeed, totally shaved, of course she would have needed to be to pull off that bikini in the first place. "Now, no ropes this time... I'm going to trust you to take it slow, and give me the time I need to open up, ok? I have been practicing... but I was not wearing a plug all morning like I was last time, so be a good boy and don't rush things"

Ron's cock was ahead of the rest of him, already rising in anticipation of stretching out Amanda's asshole once more, and Ron finally shook himself, smiling a bit. "You're sure about this? Out here in the woods?" When she simply nodded and rolled over onto all fours spreading her legs and looking back at him invitingly, he realized he needed, perhaps the first time in his life, to take some initiative. Nodding, he moved behind her, ignoring both the lube, and the erection pressing against the mostly dry cloth of his swim trunks, to place both of his hands on the cheeks of her ass, spreading them wide, and enjoying his first real unobstructed view of the hole he had crammed so full weeks before. Before he could second guess himself, he leaned forward, running his tongue between her cheeks, teasing just the very bottom edge of her pussy, before sliding along the skin between, and over the tight rosebud of her backdoor, marveling that she had managed to take him into such a tight little hole. More licks followed, as he, inexpertly, but enthusiastically, started to rim the surprised Amanda.

For her part, Amanda had not at all expected the aggressive tongue bath from the usually shy and reserved Ron and was too shocked to respond as the first sensations washed over her. She had never had her ass eaten before and was finally marshaling her voice to protest when Ron forced the tip of his tongue hard against her asshole, and she felt it sliding open. Instead of her planned protest, a low moan slipped from between her lips, and she decided maybe letting Ronny explore was not such a bad idea after all. "Mmmm fuck, Ronny... where did you learn to do that, you naughty boy..."

Ron's only answer was to continue his exploration, alternating between long licks, and teasingly working his tongue against her hole, until it was opening willingly, letting him work the questing tip of his tongue deeper into her backdoor. Eventually his tongue tired, and her asshole opening easily, he pulled back with a grin. "You did say I needed to help you open up, right?" Ron surprised them both by teasing her slightly, even as he worked his way out of his trunks, his oversized cock bouncing free. "Think you're ready?" He asked with more of his usually-cautious tone, as he reached over to the bottle of lube, and drizzled some of it into the crack of her ass, before coating himself liberally with the thick liquid.

"Mmm, fuck, I'm not sure, but I need that cock of yours inside me... I am so fucking horny and teasing you all morning has not helped." Amanda all but growled, reaching back to rub the lubricant across her backdoor, working three fingers into her surprisingly relaxed hole giving Ron a bit of a show as he lubed himself up. "Don't keep me waiting" She whimpered as he made no move to step forward, pulling her fingers free and reaching back with both hands now, putting her head down on the blank and spreading her cheeks wide. Ron, finally realizing this was his cue, dropped back to his knees behind her, rubbing the flared head of his cock between her cheeks, carefully lining it up with her rosebud. The size difference was obscene, and if he had not seen her take it a few weeks before, he never would have tried to make it fit now. But with another whimpering order from Amanda, he gripped himself tightly behind the head, and started to push.

Amanda groaned, struggling to hold herself still as the pressure grew. She knew she could take it, and she was desperate to feel that filling sensation from the last time, but between the position difference, the lack of a few hours of plugging or something else, he felt bigger than ever, and her asshole was resisting, refusing to open wide enough. Ron paused at her groan and she panted, finally grinding out. "Keep... fucking... going." Still he hesitated, and she growled in frustration, trying to push herself back, struggling to force herself open. Finally getting the hint, Ron started to push forward once more, and she felt her asshole starting to give way. It spread, stretching around his head bit by bit, the tight ring of muscles starting to ache, and then burn as he pushed her to her limits, and still he was not fully inside... but along with the growing burn was a matching frisson of pleasure from her long-denied pussy, something about that pain mixing in her brain, turning her on just enough to keep her from stopping him.

Ron watched, transfixed as Amanda's tight little asshole spread slowly to accept his cock. He was mindful of her words, not rushing, just slowly working more and more of his head inside, trying to ignore how the overtight hole was almost painful as it squeezed along the crown of his cockhead. He also tried to ignore Amanda's whimpering grunts as she stretched even wider, seemingly stuck around the widest part of his oversized head, the poor muscles of her backdoor stretched taunt around him. Instead of stopping, however, he thrust, just a bit, but it was enough. They both cried out as his head popped into her ass, him in pleasure, her in an aching mix of burning pain and triumph as her abused anal ring clamped and spasmed around the still massive, but slightly thinner shaft of his cock.

She managed to gasp out a mangled "Hold it!" Stopping him from pushing any further as she worked to once again adapt herself to his overwhelming thickness. Her asshole on fire, but her cunt was also spasming, the head of his cock pressed hard against her g spot, the pressure there turning just enough pain into pleasure to keep her from blacking out. Struggling, she worked to calm her breathing, and then to relax her straining muscles, not just her asshole, but the long muscles in her thighs, her fingers digging into her ass where she was still holding herself open for him. Minutes (though they felt like hours) later, the aching, burning, clenching pain subsided, melting into that overwhelming full feeling she had remember, and been craving ever since their first time together. Blowing out a long breath, she spoke. "oof, fuck big boy... that first step is a doozy." She managed a weak giggle, trying to get some of her equilibrium back. "You can move now, but just a little... and remember... SLOW"

Placing his hands carefully on her hips, Ron, who had frozen in dread when she told him to hold it, allowed himself to relax, glad he had not hurt her as badly as he had feared. Slowly, carefully, he started to push himself forward, the lube allowing him easier passage as he slid an inch of himself inside her, watching her wide stretched hole swallowing him. He shivered, pulling back even more slowly, tugging the head of his cock back against her asshole until she whimpered, and told him once again to stop. Sensing that was going to be too much, he pushed forward again, working a slow rhythm, pushing in a bit further each time, pulling out until he felt the resistance of her tightly stretched hole, and then sliding forward again. Beneath him, Amanda had gone almost limp, just accepting the slow widening of her insides as Ron worked himself further in with each stroke.

Amanda was lost in some sort of anal daze, her pussy flattened, her g-spot crushed deliciously every time Ron's mushroom of a cockhead slid across it, on both the out stroke and the in stroke. She could feel him opening her up, her asshole relaxing even further as she melted into the delicious sensation of being so completely full. Before she knew it, she felt his hips brush against her ass, and realized he had managed, by slow inches, to work himself balls deep. She let one hand slide down her belly, swearing she could feel where the head of his massive cock pressed out, buried deep in her guts, while she pushed herself back up with the other, pushing back into him, taking every last inch of his cock into her.

"Mm fuck, Ronny, taking you is not easy, but it's SO worth it... Now... I want you to fuck me hard." As she spoke, she pulled her other hand down, bracing herself, and wiggling her ass back at him.

"Are... are you sure?" Ron's hesitation was back, and Amanda rolled her eyes, shocked that someone could be that passive while balls deep in her ass.

"Yes, I'm sure, big boy... I'm horny as fuck, the hard part's over, now fuck my fucking brains out!" To make her point, she pulled herself forward, groaning as his cock slid though her insides, and then slammed backward, grunting as she pounded his cock back inside herself, her pussy clenching once more at the painfully pleasurable sensation.

"As you wish, Miss." Ever the pleaser, Ron clamped his hands down around her waist once more, gripping her more firmly, and did as he was told. He pulled back, inch after thick inch, until only the head of his cock remained inside, tugging almost painfully against her anal ring, and then he slammed forward, with most of the power in his strong thighs and toned back. Amanda grunted, feeling as if he pounded the air out of her lungs, but her pussy pulsed, and her asshole clenched greedily around him as he pulled back and thrust in again, even harder this time, his hips slapping loudly against her ass, and his balls swinging forward to crash against her empty cunt. He built himself into a pounding rhythm, the earlier blowjob giving him just enough control to fulfil her wishes, slamming into her over and over again, as the signals of pleasure and pain swirled and melded, building up inside Amanda.

If she could have pulled together a coherent thought, 'be careful what you wish for' might have been high on Amanda's list, and Ronny showed her what he could do, fucking her harder than she had imagined possible, stretching and reshaping her insides to fit his cock, and flattening her empty cunt and thrumming gspot over and over again. Grunts, whimpers, moans, and the occasional "oh fuck" were all that could slip past her lips, as Ron pounded her relentlessly, until she could not even hold herself up any more, collapsing to the ground as the first anal orgasm ripped through her, his balls slapping into her clit the extra stimulation she needed push her over the edge. One melded into another, the new position letting him hit newer, deeper spots and causing nerves that were never meant to be stimulated this way to get tied up in the mixed up pleasure pain centers of her brain, as she orgasmed over and over again from the endless anal abuse.

Finally, as Amanda whimpered and moaned and twitched underneath him, Ron reached his limit, slamming himself balls deep once more, his balls tightening and pulsing as he unloaded into Amanda's ass, holding onto her tightly as he drained himself, shot after thick shot filling her, until with a last groan, he collapsed, slumping down over her as Amanda's ass and pussy clenched and twitched through the aftershocks of her last orgasm, milking the last drops of cum from Ron's softening cock as they both struggled to regain their breaths.