Playing Games and Riddles With Alumni.
By BEWD 4133. Listen to the Podcast at Explicit Novels.
"Fuck, almost there, keep going Ashley," he grunted, "I love the way I feel can feel how much you're fighting not to choke on my big cock, not just for your pride but because you love it that much. There's nothing like how my girth feels prying open those pretty lips and my length feels busting into your throat. Of course, you should just think of it as a preview for what I'll do to your pussy soon. Ah fuck, here it is, swallow as much as you can."
His hand carefully but firmly found a position against the back of her head to ensure the smoothest transfer of his essence to her mouth and stomach as possible. Ashley received the creamiest ropes of semen she could've asked for as Derrick furiously let loose with his first ejaculation. He remained mindful of just how much he was shooting out but maintained confidence in her ability until he actually saw his cum leaking from her lips, at which point her let her go to process what he had given. She gulped down the excess as efficiently as she could until she was able to open her mouth to show off the rest of the helping Derrick had provided her, to which he was all too eager to take another picture."Fuck yes, that's what a blowjob on a real man should be like," Ashley polished off the remainder as Derrick sent the latest photo to Aaron again.
"Good to see you got enough. I still wanted to hold most of it back until the real thing," he recomposed himself, "Even Aaron is saying here he knows I can still cum more than that."
"Well, you can't go and make your friend out to be a liar now, right?" Ashley was quick to dispose of her remaining clothes as Derrick did his as well.
She plopped herself onto the nearby bed and Derrick was on the very cusp of joining her until he noticed notifications he had neglected while fooling around with Aaron. Seeing who they were from prompted Derrick to promptly return the phone to its rightful owner.
"I think it's best if you handle this one," he took a seat by her side to peak over her shoulder.
"Who is it now?" she noticed the several incoming texts from her group of old but familiar high school contacts.
"You didn't say it was me, but you couldn't help letting them know that it is one of their fellow graduates."
I couldn't help it," Ashley looked over an array of disbelieving responses.
The conversation was a mix of speculation and mystery, both at the owner of the immaculate member and how a dick this big had supposedly slipped entirely underneath their radar. In particular, their not-so-fondly remembered classmate Sherry seemed particularly motivated in her investigation.
"Well, it's nice to know what the most popular girl in school would've done with my dick. On the other hand, that personality is a major boner killer. Why do you still talk to her?"
"You can't pick your graduating class, Derrick. You make do with who you've got. We've been together too long for me to simply cut her off."
"So, what do you plan on doing now? I don't think they'll let you off without an answer," he noticed the reply chain still continuing even without their further input.
"I'll leave that up to you, big guy," she patted him on the back, "I say it's a chance for you to make up for lost time."
"Hm, well, I might end up regretting this, but what fun would life be without a little risk," he pondered momentarily, "Answer them back with a question from me.'
"Which would be?"
"Who in the school had the biggest dick they knew, have them send a message with the object they'd compare it too, and their best guess who my dick really belongs to."
"Consider it done," Ashley fulfilled his request as he prepared himself for further action.
In the time awaiting their replies, Derrick provided Ashley with her own private performance, keeping his dick primed for the next round through the use of his own hands, giving her his own insight on his manhood to keep her womanhood adequately soaked for the impending intrusion.
"What does it even feel like having your dick turn into that. Is it ever painful?" she looked over his towering length from between his spread-out legs.
"Close your mouth and gradually puff out your cheeks with air until they're full."
Her face beamed with enlightenment as she actually followed through on his suggestion. Even so, she knew it still wasn't an adequate comparison to his size and endurance.
"Wow, I honestly am now able to get what you're trying to describe with this example, but I still can't imagine doing it with something that large for so long."
"I almost can't either," he held up his tool which was as swollen as ever, "When alone it can seem like a pain in the ass. It messed up the zipper on those slacks long before you ever got a look at them."
"I see," she nodded, "Guess it's only fair with what fast-developing girls like Sherry have to go through with their bras."
"Perhaps, but, it's your eyes that are really doing something to me here, Ashley," Derrick admitted.
"My eyes?" she questioned, "Not my butt or boobs?"
"I know you're already aware that you're not the first to see it, but you're the first to look at it quite like that," he resumed his monologue.
"I'm just trying to feel out how much I can stare before it comes off as rude. I never imagined any man could have such a perfectly formed dick. Most as long as you lack the girth to maintain an appealing shape, and the other ones only exist in pictures that I always suspect are photoshopped, " she crawled closer to him, "If you couldn't tell by the photos, I could pretty much look at it all day."
"I can more than see that in your eyes, and that's what's got me going here like never before," his hardened appendage rose further as if deliberately aiming to meet her stare, "My very body aches to show you want to see. The look on your face each time you see it twitch or grow even just a bit more shakes me to my core like nothing I've ever experienced. I don't think I would ever stop getting harder for you as long as you kept looking at it like that. It wears me out, yet it fills me with an invigoration I've never found anywhere else in my life."
Derrick grit his teeth as they exchanged looks before both going back to one another's loins. Derrick's proud cock soaked in her gaze so acutely that she thought his veins would burst with how they billowed up at once before her eyes. The way her pussy visibly leaked at the sight was a further contributing factor towards his nigh immeasurable excitement.
"Shit, at this rate I'll be remeasuring you by the end of the night," Ashley ran a hand through her hair to keep from inwardly overheating, "I only feel even worse now for needing this to finally pay you some real mind and notice you in the correct way, but I can't help myself. Sorry, if you ever felt I was neglecting you."
"That's on me for being too passive, but I'm going to change that from now on and give a girl I truly like what she truly wants. No further questions asked."
"Speaking of which, that survey you ran has come back in full," Ashley picked up her beeping smartphone.
"And what do we have."
"Mainly names you might vaguely remember as acquaintances like Ken and Dan, most of them paired with electronics like tv remotes, iPhones, and old video game controllers."
"And Sherry?" Derrick expressed particular interest.
"Ben, with a photo of her Dad's eight-inch adjustable wrench. Easily the largest object sent back to us."
"Really? Ben? I remember him being cursed with inherited health and weight issues from his family. Nice guy but unfortunate as they come. Glad to see even the genetics lottery will dole out consolation prizes. Surprised that a shallow girl like Sherry fucked him. I never saw them dating so I wouldn't have thought that she had it in her to do charity like that. Good for her."
"Hold your praise. There's probably more to it than that."
"If you say so," he shrugged, "So who do they suspect my dick belongs to."
"The overwhelming winner there is Aaron."
"What? But he's gay."
"They know. It would explain why it's a dick none of them recognize and they think it's the sort of prank I'd pull on them."
"Any other guesses."
"A few for well-known jocks because of stereotypes I guess..." she paused briefly, "Hold on. I've got one in here for Derrick from... Josie!"
"Josie the valedictorian?"
"That's the one."
"The one who narrowly edged you out for the spot? I'm glad to see there's no bad blood there."
"There isn't, but the reminder wasn't needed," she leered at him.
"So, what drove her to single me out?"
"Let's find out..." Ashley keyed in another text and read off the reply, "It would seem she caught you standing at attention once or twice in the few honors classes you shared. She didn't want to go spreading uncorroborated rumors, especially since it made your lenis genuinely look huge and didn't want to nonchalantly mess ul your sex life with false expectations."
"And how are the others taking it," Derrick noticed Ashley suppressing a laugh, "What is it?"
"They said they forgot but remembered that you were Aaron's closeted boyfriend so it would make sense," she couldn't hold back at least one chortle at his expense.
"Ah, so that's how it is..." he rolled his eyes, "Guess it's time for me to come out of the closet then..."
"How so?" Ashley grew inquisitive.
"Up for one or two more pictures with me?"
"Just tell me where and how," she consented.
"A few selfies," he signaled her to approach him, "One with my dick and your forearm and another with my dick and your head."
"And your adorable face?" she added.
"As you see fit," they posed for the photos together with the aid of a nearby mirror.
Not only did Ashley's phone blow up mere seconds later, but Derrick heard his phone ringing with messages from Josie, who had his number for an old group class project.
"Oh, now you've rocked their collective worlds," Ashley scrolled through the pile of fresh texts.
"Ah, that figures," Derrick checked out his own phone.
"What?"
"That girl I took to the movies last winter? It was Josie."
"Really?"
"She got into John Hopkins but is living at home. I didn't want to mention her by name since I was calling her a bit boring."
"Smart move."
"Now she's saying she had a crush on me even back in the day. She knew full well what she saw and was scared to have it go around and have me get taken by someone else. Her parents forbade her to have a boyfriend amidst her applications for college, but hearing I was gay right before graduation scared her off from asking about a serious relationship even when she did happen to want to see a movie with me. She didn't want to see closed-minded."
"The social hierarchy can be so fascinating at times," Ashley sighed, "So what are you gonna do?"
"Simple," he smirked while operating his phone, "If after that, she still had an interest in me, wouldn't that imply that she really likes them big?"
"Quite the observation."
"I look forward to her answer, but I'm here for you and ready to explode."
"Shall I help you impress even more of your old classmates?"
"Sure," he approached her from above as she laid back for him.
For his personal coup de grâce, Derrick lined his dick up over her abdomen for one last snapshot showing just how easily his length reached up to her belly button as a warning to himself and others just what Ashley and any future comers would be in for with him. He could hear the phone blowing up even more than before, but paid it no mind as making deep love to the girl before him stood as his only remaining objective, which he had already taken more than enough time to ready himself for. The swirling tones of local gossip seemed to have increased Ashley's eagerness as well.
"I'm sure none of them can even fathom just how far I'm about to get plowed into," her body tingled with his first prods at her moist entrance.
"Tell them as much as you want but be sure they know I'm trying to make it special for you," Derrick grabbed her ankles as he made his great plunge into her.
Even as he paused to enjoy the moment, the continued squeezing around his member firmly demonstrated the great thirst growing in her increasingly impatient loins and persuaded him to get back to plowing his way through the tunnel of flesh. They hadn't lost any of their tenacity even after the pounding he had delivered last time, but anything less would not be satisfactory to get him to achieve the scale of orgasm they were both aiming for here.
It wasn't his first foray inside of her, but it was the first where he could see her face and it made all the difference in the world to him. Looking at the expression of a woman pushing her body to its limits for him was difficult to fully comprehend. Going at her from above also let him view just how her vagina split and her abdomen bulged when stuffed with his cock. Even buried within her, the look in her eyes that he had spoken of before persisted and was aided by the sound of her voice coming in to communicate her feelings. It started as tiny gasps and moans, but Derrick immediately knew that he wanted more.
"Tell me, Ashley, please," he begged between heaves, "How is it different having it inside than outside. It's borderline euphoric for me. I need to know what it's like for you..."
Ashley's thoughts proved difficult to collect with each thrust he made scrambling and rescrambling them, but she took in a breath to give Derrick the talk he needed, the words floating in the back of her mind since they had started.
"Oh shit, it's like I'm going to split in half. It's such a marvelous thing!" she shouted, "I'm so privileged to have someone like you ravage my insides with such a monstrous cock. Your pulse rushing through every fat inch is unlike any I've ever felt in me. I don't care if you end up ruining other men for me. I live with the thought that I found such a great guy with a dick like this and didn't take full advantage. Please leave your mark on me however you wish!"
"Yes, I love how perfectly tight your pussy stretches around me!" he called back to her, "Whether it be pants or condoms, nothing ever really fits on this dick, but I can tell how badly your insides want to! Every move I make rearranges everything I feel in you until it's completely snug on me once again. I think of what kind of hole I'm leaving behind and would love to see another man try to fill that gap, but, for tonight, this cute, sexy body of yours is mine alone. It was made to be filled with this big cock of mine and it's doing a damn good job of it!"
"Yes, Derrick, but it's not just this ridiculously huge cock of yours at work but those fat balls that go with it. I need to feel just how much cum it can really shoot. Let it loose in me. It's your duty as a man!"
Derrick took his duty quite seriously as he felt his greatest eruption yet building within. He pushed himself harder and harder just as his mass was doing to the girl beneath him. As he got into his rhythm, it awed him just how easily he was lunging himself all the way into her and how good each one felt. He was so zeroed in on getting to his climax though, that he found himself utterly blindsided when her entire form, inside and out, began to tremble and undulate around his manhood all at once.
"Oh, I'm cumming," she moaned, "I'm cumming so hard that I wouldn't dream of taking another, lesser cock."
"Well, you'll sure as hell never get that from me, he switched to holding her hips.
Her climax subsided just before the sensation of her quaking around him brought him to orgasm as well, but he was still only a mere handful of thrusts away from hitting his peak anyway. After all he had done for her, Ashley was content to have him take hold of her almost limp body and use it as he needed to relieve himself. She could still make out the heavy pulsing in his dick ticking down to total release and she loved the energetic expression adorning his face as he made his way there. As he drove further and further into her deepest regions, the walls just before the end of her vaginal canal started to grip onto the flesh just beneath Derrick's glans particularly tightly, he felt himself beginning to twitch with the first hints of a climax but was stunned to feel her pussy pick up on these clues perfectly and react with astounding pressure.
"Fuck Ashley, you'll make me cum. You're gonna make me cum!," he panted as her flesh struck his weakest spots like magic, "Get ready to take it all in that perfect pussy!"
His gargantuan penis began an all-out rampage inside the girl he had kept his eyes on for so long, thick with anticipation, as they both counted down to his climax. Derrick felt the pressure building within him while Ashley made note of every warning signal she could notice. Each twitch of his dick was met with a shiver, each swell was met was a squeeze, and every gasp and groan from Derrick prompted Ashley to pull him just a bit closer with by shooting up her legs to lock around him. Soon enough Ashley got the sign she was truly waiting for was his entire member bloated within her.
"Oh fuck, there it is," Ashley groaned, "You're getting bigger and biggeeeer. You're about to let loose with all your hot, sticky cum, aren't you?"
"Yeah, I'm about to explode, but when I do it'll be so much you won't know what to do with it!"
"Bring it on! Bring it all on! I'll cum right with you!"
"Here it is!"
Derrick's second orgasm of the night struck with a vengeance. It released heap after heap of seen into the girl with every blast hitting squarely against her cervix. Despite his bold words, what mattered most to Derrick now was filling her with as much of his sperm as he could muster. Taking his load was as much her pleasure as it was free as his semen finally burst forth. His torrential release made quick work of filling the space his mammoth meat hadn't already, but it wasn't long at all before she felt his leftover spunk leaking out of her as he just kept on cumming and cumming. She never doubted Aaron's instincts but the way she felt him just keep on going and going soon shifted from impressive to truly awe-inspiring. His monsoon only ceased when he finally collapsed on top of her entirely, frantically gasping for air.
"That was utterly amazing, Derrick," she lifted a hand to rest in his hair, "I doubt anyone will believe me even when I tell them."
"I'm just glad to have made a believer out of you here and now," he shifted back down to his typically more relaxed personality.
"Aaron would've been proud," she joked.
"Yeah, he's not getting anything like that out of me anytime soon," Derrick rolled back off of her after one more kiss on his cheek.
Ashley turned her own head to see her own phone glowing with new messages. She saw Derrick's phone doing the same and stretched to fetch it for him.
"Let's see what we have here now," Ashley skimmed through her phone as Derrick looked at the mess he had left behind all over her crotch. By the time he had noticed her grinning at the screen, she had already clicked away from what she had been reading.
"Anything good?" he then decided to check his own inbox.
"Sherry's salty again, but when isn't she?" she remarked, waiting to see what it was Derrick had gotten, the identity of which had his eyes widening significantly.
"What did you get?" she questioned until he held the phone up to her.
What she saw was the sole text Josie had sent since Derrick's last message. It simply contained her full bared vagina next to the largest dildo Ashley had ever seen in real life. It had numbers written on it to show dimensions of nine by six inches with a message stating "Yes, but I didn't like them big enough apparently." Derrick humored her with a simple "lol" but was quickly answered with a text now reading, "I can't find easily one larger than this, but I guess that there's no substitute for the real thing." Even at his most awkward, Derrick would never have been dense enough to miss this.
"It's always the ones with the strict parents," Ashley observed.
"I guess," Derrick's mind became stuck on the proper response.
"Well, technically she did see you first," she acknowledged the truth, "I have no real right to complain about her wanting her shot."
"But I'm here for you now," Derrick rebutted, "No point worrying about the past. I have no problem taking you as my girlfriend."
"Thanks, but I still have to head back up north when the new semester starts. Even if I'll never be able to forget the fuckings you gave me, I've learned that long-distance relationships aren't my thing."
"I have no intention of going anywhere, so I'll almost certainly be here when you're done."
"And what you do until then is your business, but I'll gladly keep you in mind."
"But we've still got not only a lot of summer left, but a lot of this night left," he reminded the young college girl.
With a gesture of his hands, he guided her attention back to where his erection had already reawakened for her.
"It would seem I've sorely underestimated you," Ashley confessed.
"Are you disappointed?"
"Not even close," she got ready to get back into gear with a playful crack of her knuckles, "Who knows where we'll be a year from now, but I do know that I'm nowhere near done with you yet."
"I look forward to seeing who will be done with whom first," Derrick shot back from gusto.
Just as Derrick and Ashley shared a long night together, they were more right than they would have guessed in predicting the long summer that waited ahead.
To be continued.
By BEWD 4133 for Literotica.
Source: ex-plicitly-novel