First Times Series | Book One: Intro and Applejack

“Y’sure about this?” Applejack asked, once again feeling the weight of an older colt on her back, and the warmth of another against her chest as she squatted over and laid chest to chest on her brother, legs spread to the colt atop her and beneath her both.

“Sure Ah’m sure,” Braeburn replied, looking down on her as he took the opportunity to mount her again, “Ah read about it in a magazine, an’ it seemed like a lotta fun fer all involved. But ya need a lotta lube t’ go in somepony’s anus, else it’ll hurt a lot. An ya got a lotta lube right…down…’ere.” He ground his flare against her cum-oozing pussy, emphasizing his point.

“Well…hurry up’n get on with whatever yer doin’! Ah want more sex!” Applejack groused, though her attitude sure changed as she felt him easily slip into her pussy again, sliding all the way to his balls into her, him savoring her warm, clenching depths, and her his filling dick, for a moment, before pulling out again.

“There we go, all lubed up. Now then…” Braeburn said, feeling quite eager as he heard his little filly cousin, whom he’d seen grow up into the beautiful young mare she was now, literally begging for his cock up her ass, who was Braeburn to refuse her offer, he thought. So, with a firm push of his hips, he pressed against her virgin ponut.

Brae started cramming his cock more firmly against Applejack's pucker, trying to enter, but found that it was tighter than her pussy was. Way tighter. "Oh c'mon!" he grunted in frustration as he tried to enter her rear, to no avail. That round pucker just wasn't giving in to his flare's demands, even with all of the lube he had on it.

AJ wiggled her butt impatiently in response, her desire to get back in the action, to be penetrated and filled again growing to be intolerable, the burning in her pussy growing as it was left empty. "Put it in already, Brae-Brae!" Applejack said urgently, pushing back onto the flare against her asshole.

Getting frustrated, smelling the heated mare beneath him, hearing her beg for his cock, and wanting to get his dick inside her again, Brae pulled back a little, preparing to enter her with more force. As he rammed his hips forward, he felt that seemingly impenetrable sphincter's tightness nullified under the force of his thrust and the lube. While it worked, and Braeburn felt the warmth, and a tightness he couldn’t have even imagined compared to her marehood, of his mare surrounding his colthood again, it didn't lead to the desired result from Applejack.

Applejack loudly cried out in pain, with Braeburn's penetration feeling like she'd just gone a massive number two, but in reverse. Her bowels strained at the sudden intrusion, it felt like when Braeburn had suddenly entered her pussy, her lower belly aching once more. "What the buck, Braeburn! Ya just...rammed it in meh again?! That hurt like Tartarus!"

Despite the pleasant tightness and rippling contractions around his upper shaft and flare, Braeburn's mindset immediately changed to being worried about the mare his dick was stuck halfway into now, not moving at all, not wanting to potentially cause any more pain than he already had.

"S-sorry cous'!" Braeburn said, feeling guilty that his rashness had hurt his cousin for the second time that night.

"S-stop, jus'...don't move. Gimme a sec," Applejack said, then, when her overeager cousin did as he'd been asked to do, she let her body adjust to its intruder, just like she had when he'd taken her vaginal virginity, meanwhile testing various muscles in her abdomen to find the right ones to relax. As she untensed a specific group of them, sure enough, it started to hurt less as she gave him more room, and her body adapted to being filled there too.

"Sh-should I pull it out again?" Braeburn asked worriedly, despite that being the last thing he really wanted to do.

The offer of Braeburn wanting to pull out triggered something inside Applejack; she did NOT want him pulling out, leaving her empty again. "NO!" Applejack sharply exclaimed, before clearing her throat, her cheeks flushing a bit at her outburst, "What Ah meant is, ya don't gotta pull out, but please start pushin' in slow when ya do...or at least slower, yeah? Or do ya even know what slow is, Mr. Freight Train?"

"Sorry..." Braeburn said, giving a small indignant huff at the unwanted nickname, before starting to slowly slide deeper. The lube had started to dry out a little bit, making his lower shaft tug some as he entered her further, but it wasn't enough to be painful, simply making more friction.

Big Mac, meanwhile, waited throughout all of this, pinned beneath the two fucking ponies. His desire to penetrate his sister again was slowly beginning to grow stronger and stronger, and he was starting to struggle with containing himself. As he heard her in pain, however, the empathy he felt for his sister in this situation showed in a kind of wholesome, brotherly way, his forelegs reaching around her neck, embracing her and rubbing over her crest as Braeburn slowly went further into AJ's ass. Being hugged while she was trying to get used to the new, somewhat strange, still mildly painful, but nonetheless enjoyable sensation helped Applejack more than she'd ever admit. Leave it to her usually-rival brother to be there for her when she needed him most.

Simultaneously as he held her, Big Mac's member was ever so slowly teasing AJ's clit as it flexed in anticipation, gently rubbing against and over her vulva, since his natural desire to penetrate the mare in heat never escaped his mind, and less so his body, entirely.

Every slow motion, every gentle thrust Braeburn penetrated AJ with, got her more and more used to her ass being filled, until eventually the initial pain from her cousin's inexperienced entry faded away entirely. Meanwhile, Big Mac's patience slowly came to an end, his cock drooling precum with each throb. Feeling through the bulge it made in her belly against his own that Brae was then going in and out of Mac's sister at a reasonable pace, and the quiet moans those thrusts got from both of them, he figured she couldn't be hurting that badly anymore.

"I'm waiting for yer OK, sis! Ya ready fer me ta get back ta fuckin' yer pussy too?" Big Mac asked, not so subtly hinting towards his burning desire to join back in on the action. AJ was apparently a little too focused on relaxing the right muscles, and the pleasure, then to think about there still being another member to enter her needing fillyhood.

"S-sure, go 'head, bro!" Applejack moaned out, winking her clit against her brother's tip in invitation. She was meanwhile getting used to the new feelings of Braeburn taking her in the asshole; it wasn't quite as pleasant to her as having a dick in her pussy was, but it felt...different. It had the same feelings of fullness that she craved, and it kind of was like when a penis was in her foal-canal, but...not; it was more of an echo compared to the much stronger pleasure she felt when she was being penetrated in her fillyhood. But even a bit of that feeling was still quite nice.

Mac pressed his flare to Applejack's winking pussy, awaiting the right moment to enter. He observed Brae's pace for a short while, trying to follow the agreement that they had made to have only one penis inside AJ at any time. Timing it as Braeburn pulled out, Mac pushed in. As wet as everything was - including AJ's regular juices, those from her most recent orgasm, as well as most of their cum still sticking around - and with her looser from them already having had their first little experiences of getting into AJ's passage, it was a smooth entry, Mac sliding balls-deep in seconds.

It took a while for the colts to get the pattern down, each craving to be buried into the warmth of the filly they were sharing: either one started to penetrate while the other was inside, one enjoying Applejack's warmth for too long that they didn't pull out in time, or neither thrusting before the one hesitantly did as they forgot their order, but eventually they got the hang of it.

Braeburn, meanwhile, couldn't believe how much tighter Applejack's rear hole was, with the lesser lubrication, and thereby higher friction, also letting him feel the texture of this new hole better than her pussy. Unlike said pussy, her rectum was much smoother than her ribbed vaginal walls, though still had these little curves in it that still gave plenty of stimulation. Every time he entered, her anal walls would ripple along his dick, as though trying to push him out. It was almost a sheer contrast to her pussy seeming to pull him in, though it was not a contrast he minded much, as he just pushed harder against the contractions, getting deep into the warm tightness his colt-dick craved.

Despite the rocky start to Braeburn entering her, Applejack groaned at the sensation of being filled like this now, the feeling of taking it in two holes at once while so sensitive from her estrus, of how filled it made her constantly feel. Before, when only one stallion was in her pussy, there was always a delay before the colthood within her would enter again after each thrust, while with the alternating thrusts Big Mac and Braeburn were taking into her, she was never left empty.

While Big Mac loved the tightness of his sister's little fillyhood squeezing around him, he was unsure how Braeburn was doing; but if the utterly blissed-out expression on his face was any indication, he must be feeling at least as good as he was. After blowing his first quickshot load, Mac was lasting much longer his second round, as he found it always was, quite enjoying his mare's canal now that he actually had the time to savor more than just six thrusts, giving evermore when it came his turn to enter the heated filly's pussy again.

Applejack felt pressure building in her lower belly faster than with either colt, her inner muscles squeezing down frequently and randomly, her clit a flurry of near-constant winks.

"G-guys...oh mah Celestia YEEEEEES..." Applejack forced out in the most lustful, adoring tone a filly could make, feeling so good as both colts pistoned in and out of each of her holes. Unable to even warn them with how suddenly it came on, Applejack let out a feral whinny as her third orgasm, this one stronger yet than either of the others, overtook her just as Big Mac entered her to the hilt again, with his flare pressed to her cervix. The pleasure rolled through her whole body as her walls started squeezing down rhythmically on her big bro's cock again, soaking his and Braeburn's balls with her squirts of marecum. Her body was trying to have a repeat performance of getting him to blow his load in her early once more, though that was not to be this time.

"There ya go, let it all out...holy hay yer tight li'l number clenchin' down on me feels so good..." Big Mac said, and, as he felt his sister cumming again, he nuzzled into and kissed her neck, rubbing her back as she trembled in his grasp. Her whole self quaked, with Applejack unknowingly having her first-ever full-body orgasm. Mac meanwhile enjoyed the feeling of her vaginal walls milking his dick, giving a quiet 'mmm' as it throbbed in return, depositing yet another glob of precum onto, and into, her relaxed cervix.

Braeburn felt as she squeezed too, but only on his flare, though what he did feel was like her ass was squeezing the life out of him. "Holy hay ya can squeeze, cous'!" Braeburn exclaimed, though neither of the other ponies were really in the state of mind to respond to him; one cumming her brains out, and the other enjoying the milking on his dick and the quaking mare pressed against his chest. Brae nuzzled her crest as she squirmed and shivered, waiting for her orgasm to end so he could get back to fucking his cousin up the ass.

AJ's body was visibly shaking from the pleasure, taking a few seconds after to regain her balance as she was panting, the exertion that such an overwhelming release caused making her enter a state of exhaustion that didn't feel like when she worked, but enjoyable.

Seeing and feeling that Applejack had recovered from her orgasmic journey into bliss, Braeburn could feel how the extremely tight grip of AJ's anal canal loosened some around his flare, allowing him to slowly push his member back into her, temporarily forgetting about their previous agreement, only wanting to feel the warmth of the filly's rectum surrounding him again.

Big Mac was still deep inside AJ, able to feel how much tighter her pussy got as Braeburn entered at the same time, as both were in AJ to the hilt simultaneously, neither noticing their balls pressed firmly together until one's pulled up slightly when their dick throbbed. Not that either really cared, with it just being more stimulation to their frazzled young minds.

Applejack moaned loudly with as much as this was stretching her; it didn't feel bad though, now that her body was more adjusted to being penetrated, and she in fact found herself rather enjoying the almost, but not quite, painful stretching.

"W-wow..." Applejack said, her voice having the same awe-struck tone it had held when she'd seen the giant rainbow explosion that had guided her home, and led to her getting her cutie mark.

"Yeah, 'wow' indeed..." Mac replied, his hooves wrapped around Applejack's neck, hugging her softly to him, and her burying her muzzle into his chest.

Both colts also realized then just how thin the inner walls of a mare were, and how easy it was to feel through them; with their shafts only separated by a thin wall of flesh, that fact really came to bear. Each throb the one's dick made was felt by the other, and it was a new sensation to them; unexpected and kind of weird, but not entirely unpleasant. Braeburn felt Mac pulling out, with him following suit, and soon they both adjusted back to their original technique and pace.

"Hey, uh...how bout ya both go int' me at th' same time 'gain? That felt...wow..." Applejack said a few alternating thrusts later, wanting to get that ultimate, satisfying fullness again.

"Uh...sure, iffin' ya think ya can take it," Braeburn said, and Applejack snorted at the challenging tone.

"Bring it on!" Applejack said back with as much confidence as her tired body could muster, which wavered slightly as both colts rammed into her at the same time. She could only groan deeply, her hind legs quivering, her small holes and pelvis straining to contain both colts' cocks at the same time. But holy Celestia what a rush it was! She came a second time when both cocks filled her again, still sensitive from her previous orgasm, her whole body quaking in another full-body climax as she gushed her filly-juices all over both colts' balls, milking both colts at the same time.

When Applejack recovered, practically limp as both colts pulled out, then hilted balls deep, their nuts crashing together each time, they could feel their cocks rubbing against one another's within her, feeling a hard dick on their own only separated by AJ's wall. It was weird, and felt kinda good, though the extra tightness of them both sharing the space at the same time made it quite worth the weirdness.

Eventually, the sensations of fucking AJ led Mac and Braeburn close to their second orgasms, both colts physiologically and psychologically drained, but they still had the energy to keep going. Eventually they both hilted again, panting from the exertion of all the thrusting, with even their earth pony stamina having its limits, and not helped by their sexual inexperience. Unsure if they should pick up the pace and finish in AJ’s warm pussy and ass, or if they should slow down and try to drag this out more, Mac leaned up and nuzzled Applejack's cheek to get her attention.

"H-hey AJ? Y'need some more...?" Mac asked weakly, but didn't receive a response. Applejack looked almost catatonic from cumming twice in a row, in a pleasured daze as she was so widely filled with cock, and squeezed over them with her fillyhood greedily.

"C-cum in meh again...please...both'a ya..." Applejack begged. Her womb was burning hot from her two orgasms without a colt's seed accompanying them, and she wanted to feel that relief again. She could feel them both flaring in her, making her mind even more frazzled as she was overstimulated by that extra stretching. At the same time, her instincts were overjoyed as she felt her stallion flaring in her pussy again, his urethral process pressed against her cervix, ready to douse her heat with his virile sperm once more.

"Alright then! C'mon cous', let's pick up the pace!" Brae responded, only too eager to feel the wonderful sensations of pumping his cum into Applejack's womb again, and immediately beginning to thrust down into her ass with the speed of an overly excited colt. Big Mac followed this narrative without hesitating, eager to feel his own orgasm, even if his endurance was waning.

At this speed, their hips crashing into Applejack at the same time, both stallions struggled to keep pace, all but wildly humping into their shared mare whenever they could at that point. She groaned in mild pain at the rapid stretching - further than ever before, with their swollen flares pummeling her insides at the same time - but mostly pleasure, now that she'd gotten used to it. The overwhelming stimuli left her struggling not to just collapse onto Big Mac with each thrust of the two who mounted her. Her legs certainly shook heavily though, threatening to give out on her, as did, unknown to her, Braeburn's.

His member quickly stiffening even further, his flare growing even thicker, Big Mac knew he was right on the edge. After only a few thrusts more, his orgasm was approaching fast and, instinctively, in order to make sure his sperm was going right where it belonged - as deep into his mare's fertile tract as he could make it get - he thrust deeply one final time. Big Mac saw white as his balls pulled up to his body and his cock stiffened, before it started throbbing rapidly. He felt as he slid past that ring-thing deep within his sister’s core again, and something firm pressed to his flattened flare.

For the second time within an hour, Big Mac's body proceeded to release his virile genetic payload against the back of his little sister's womb. Wrapping his forelegs around her tightly, Big Mac groaned as he pressed his head back into the pillow. The sensations were almost overwhelming, but his body was staying almost entirely still as his cock rapidly jerked inside his mare, except for the mild spasms he inevitably underwent, his muscles locked in place to force him to keep seeding his mare.

The feeling of having her estrus quenched with a colt's foal-gravy pouring deep into her burning belly again made Applejack moan in pleasure, her body set over the edge once more as she received another intrauterine injection of her brother's soothing balm. Her body, tired as it was, twitched in another powerful orgasm as her foal-passage milked her stallion dry of everything he had left to give her...and, despite it being Big Mac's second climax in so long, what he had to give was quite a lot, pump after hearty pump of his seed messily splattering into her ripe-for-foal core.

As Big Mac kept filling his sister's womb with his smaller - but still plenty virile - batch of foal-cream, Braeburn, who'd been close to cumming too, was sent over the edge by the sight and feeling of Big Mac's orgasm, and felt himself flare fully. Mac's cock throbbing rhythmically against his own through that strip of flesh that separated them, the thought and memories of how it felt to fulfill this desire of throbbing his own seed deep into a mare in heat's womb, tipped Braeburn over his edge. Well, that, and the fact Applejack's ass was milking him tighter than even her fillyhood could as she came. Tensing his kegels to practically force himself to cum as he so wanted to, to climax in time with his cousins, Braeburn thrust as deep as he could before coming at a standstill at the deepest point in' AJ's colon as he released his semen into her, only mildly delayed with Big Mac's orgasm.

Both colts proceeded to empty themselves into her, their balls and cocks throbbing against each other, but neither even noticed that, the only thing they were focused on being the fireworks of bliss going off in their brains. They gave Applejack everything they had, and her body only too greedily took it, her rhythmic contractions working to draw out every drop it could.

As their powerful orgasms ended some time later, Applejack collapsed down onto Big Mac, and Braeburn onto her, sandwiching her between them and turning them into a particularly pleasured pile of ponies, all three gasping for air as their bodies finally came down off their highs. Both colts were still hilted balls-deep into their mare, their flares still swollen huge in her - Big Mac's plugging up her cum-filled womb from the inside her cervix again, and Braeburn's just beneath Mac's as he contained his own load in her colon. The sensation of being so utterly corked with cock and cum was a satisfaction that went beyond just a simple orgasm for Applejack. That fullness, and the fact that she'd been bred again, too.

Braeburn nuzzled into Applejack's neck as he held her barrel loosely with his forelegs, and Big Mac had his own forelegs wrapped loosely around her crest. As she lifted her head and looked at Mac, he met her eyes, seeing in them exhaustion, and a kind of satisfaction a brother should never see in his sibling's eyes...especially not while hilted balls-deep after cumming deep inside of her. Before he knew what had happened, Mac was surprised as he suddenly felt her lips on his, her forelegs wrapped around his neck and pulling him into it.

When he recovered from the shock of Applejack stealing his first kiss so suddenly, Big Mac pushed back into it, tightening his grip on his sister and pulling her tighter against him too. They kissed for a while as they enjoyed their afterglow and first kisses, lips softly smacking together as they did so, eyes softly closed in pleasure.

Eventually, Applejack pulled back, a thin strand of saliva still joining their lips, before it soon after snapped. "Wow, so that's what kissin's like..." she mused, having just given her first kiss to her brother, "...Ah think Ah like it," She paused, before sticking her tongue out to lick her lips, getting a taste of her stud. "Hmmm, ya taste good, bro."

Big Mac was just lying there stunned, a combination of his sister's and his drool on his lips. For some reason, even after rutting her brains out twice, something as intimate as a kiss was what broke his brain. "Ya taste good too, sis, but...what was that fer?" Big Mac asked after getting some semblance of thought back.

"That, was a thank ya fer helpin' me with mah heat," Applejack replied, giving a little smile, "Ah owe Brae-Brae one too." With that, she turned her head to where Braeburn's head rested on the floor beside them, lidding her eyes at the colt looking back at her, before pressing her lips to his too, exchanging their tastes with one another for a little bit.

Soon after Applejack broke her kiss with Braeburn, both colts slid from her, Braeburn's member seemingly spent and starting to retreat into his sheath...but Big Mac's still stood semi-hard. She still found herself wanting more despite her tiredness, her instincts seeing a stallionhood ready to give her more sperm, but she couldn't will herself to move. Maybe in a little while, after some rest, she'd ask Big Mac if he wanted to go again. Braeburn, meanwhile, seemed completely done, his colthood sheathed again, his forelegs folded under himself and looking on the verge of falling asleep, so she decided to not bother asking him to go again.

Big Mac however...

"Wanna go again, after a little break?" Applejack asked a few minutes of rest later, getting an eager smile from her big brother.

"Well, Ah did promise t' help ya with yer heat until yer satisfied..." Big Mac said, getting a small smile back from the filly beneath him. "...an' with how good yer fillyhood feels, Ah'd be a plum fool t' refuse gettin' ta feel yer pussy again."

After both had caught their breath, Big Mac at full hardness again thanks to his little sis's rubbing hoof, she leaned over the edge of the bed this time, with her hind hooves on the floor and her forehooves folded under her chest. As she looked over to Braeburn, sure enough, he was snoozing peacefully, and AJ smiled at how both handsome and cute he looked at the same time like that. "C'mon bro. Think ya got one more in th' tank?" Applejack asked, and got only too eager of a nod from Big Mac as he stood from the floor, then walked behind her before rearing and once more mounting over his sister, his shaft resting over her croup.

"Eeyup."