This is really it, huh? Troubleshoes thought to himself, his eyes locked on the mare in front of him with that small silver square in her mouth, no doubt whatsoever what it was or what was insinuated by its presence. "Applejack, y' SURE..." he started softly, but was interrupted by Applejack walking over and putting a hoof on his muzzle.

"Would'jya give that a rest already?" Applejack asked with a smirk, her speech slightly slurred by the package she was holding; "Now gimme a hoof with this condom. Ah got no idea how in tarnation this 'Madam Lovehoof' expects us Earth Ponies to open these thangs alone." she finished, holding an end of the package towards him. As Troubleshoes reluctantly gripped it with his teeth, Applejack moved her muzzle a little closer to get a better grip – only to softly bump muzzles with him.

Both pulled, tearing the package opem, and Applejack gave a soft chuckle after she set the now–open condom down. The muzzle–bump sent an uncommon shudder through her – and not one of simple lust. "Look lover–boy, we can do the lovey–dovey stuff AFTER ya rut me to the Moon and back, alright?" Applejack said with a snicker – but got a rather serious nod from Troubleshoes. As much as she almost hated to admit it, Applejack eagerly decided to hold herself to that promise, now looking forward to the promised post–snuggling almost more then the main act itself.

Applejack told Troubleshoes to go lay on his back on the bed a moment later, then picked the condom up in her mouth when he had, placing the tip inside and the main ring between her front teeth. She then placed the condom on his stallionhood and got a light twitch from it in reaction, using her hooves and some fancy tongue-work she'd learned during her time with the few other stallions she'd been with to get it on him, rolling it over and down his stallionhood...well mostly at least.

It would seem that the extra-large condom that her brother reported fit perfectly on him only managed to fit two-thirds down Troubleshoes' apparently above–extra–large stallionhood, also seeming to be slightly stretched by his girth as well.

"Uh, ain't it supposed to cover t' whole thang?" Troubleshoes asked, getting a bad feeling again as he noticed just how snug it felt on him and how it barely fit over his medial ring. What if during his climax it...

"Ah don't worry 'bout it Sugarcube. Even with it bein' so small on ya, 'the condom material is magically reinforced t' keep its hold no matter how far it stretches, fer added security' – at least that's what the package says." Applejack comforted him. Applejack thought; <he just needs to live in the moment for once and simply enjoy this time with a mare instead of worrying about the worst possible outcome of everything!>

As Applejack gave Troubleshoes' now-wrapped glans a kiss through the latex and moved aside, she felt him shift and soon after get to his hooves. Apparently now that he was wrapped, it was time to get on to the main act Applejack had realized... and much to her delight, at that! Troubleshoes watched as Applejack went and lay down on the bed on her belly, spreading her back legs then flagging her tail up at him, his jaw dropping and eyes springing to her sopping crotch as she so obviously and fully presented herself to him again.

After some seconds of not being mounted, Applejack wiggled her rump and winked her marehood to the stallion behind her, making her offer the most obvious she possibly could. When there still was no reaction from Trouble, she looked over her shoulder to him. "Y' comin' Troubleshoes? Ah can't exactly have sex with mahself now can Ah..." Applejack said, noticing he still was where she'd left him, a very nervous expression on his face.

"C'mon it'll be fahn. Even if th' worst DOES somehow happen, Ah still ain't in heat. Ah promise, it'll jus' be a bit o' fun... an' that's comin' from the Element of Honesty, y'hear?" Finally, Applejack saw Troubleshoes starting to approach her, that final assurance seeming to at last break his unease.

Troubleshoes mounted Applejack carefully, his rather large hooves planted to either side of her on the bed, having to bend his back legs slightly to line himself up. "Mmm, 'at's right, c'mon big boy..." Applejack encouraged, and soon felt Troubleshoes' partially-flared glans rub against her slit, feeling just as huge as it had in her mouth and throat. Perfect, right on target. "Ooh, you know just what yer doin, don't ya Clyde? Ya know how to rut a mare jus' right too, alongside givin' her the best eatin' out she's ever gotten?"

She cooed sensually, feeling him grind against her slit and lubing the condom up a bit more, small tingles of pleasure already working through her at the simple contact. Finally, Trouble started to slowly undulate his hips against her, tapping her slit as he now worked to enter his mare for the evening.

Applejack cried out as she felt his huge flare finally pop into her; it felt like he'd put his whole hoof inside of her! "Y'alright?" Trouble asked nervously, only getting a rapid chain of nods from Applejack. Content he wasn't hurting her, he continued on slowly, gently sliding into her, not wanting to be too rough with her at the start. He knew he was larger than the average stallion, in more than one way, and knew also that Applejack hadn't done this for a while. As such he was being extra careful at the start despite wanting to ravage her silly, his instincts screaming to breed her already and give her what she wanted; to fill her full with his cum.

"Y', y' can go a bit faster 'n' that, Sugarcube." Applejack said when he'd entered her only three inches nearly a minute later, a tone of impatience in her voice.Troubleshoes took the hint, entering more of his wide stallionhood into her and earning a long moan as another inch was swiftly introduced. "Mmm, 'at's a good pace. Keep goin' like that." Applejack encouraged, her pleasure slowly rising, feeling him steadily sliding into and stretching her more as he delved deeper.

"Aaaah Applejack, yer too tiiiight!" Trouble said as he had to increase his force to get himself further into her and reached his medial ring, feeling her tightly gripping him and making his entry both difficult and very pleasurable; constantly afraid he couldn't get too much deeper in her, but glad that every further inch he claimed proved him wrong. He gave a good ram of his hips and forced the wider medial ring into her upon reaching it, making her gasp sharply as it roughly rubbed her clit, her passage responding with a wink and squeeze.

"N–no Sugarcube, yer just too buckin' huge!" Applejack exclaimed, feeling a twitch from him inside her at the compliment, that sensation making her moan as he slowly went deeper. It felt like he was straining her passage a bit, her feeling like a whole foreleg was buried inside of her and stretching it nearly to its limits, but she knew she could handle it; plus it felt heavenly.

Moments later Applejack gasped again as she felt Trouble's glans hit something deep inside of her, her breeding instincts flaring hot now as she felt just how deep he was. "W-well Sugarcube, looks like ya finally hit th' end a th' line..." Applejack said, her tone deep and throaty. As she reached a hoof back and felt he still had quite some more to give, she was fairly surprised. She knew he was huge, but not so huge he couldn't even hilt her! she thought, <it'd be a lot less fun if he couldn't even get that far!>

Applejack felt as Troubleshoes' rod gave another gentle pulse in her, moaning deeply into and squeezing very tightly to her muzzle the nearby pillow she'd grabbed as she felt her inner muscles trying to work over his huge stallionhood, her body struggling to adjust to the stretching its rather large guest gave her. Never before had she felt so utterly full as she did now, all of her previous stallions lucky to be half Trouble's girth.

Hearing his mare moaning and squeezing on him like that made Trouble really want to continue, barely resisting the urge to start rutting her hard as his instincts demanded he do. "How do ya want me t' start?" Trouble asked, finding that keeping himself still was becoming harder and harder as he felt her hot, slippery passage gently contracting around him constantly, his haunches quivering lightly and his back hooves stepping in place as he became antsy; eager to rut this wanting mare.

"Mmm Trouble, Ahm happy with whatever you wanna do – rut me, make love t' me, I'll love it either way. An' dun worry 'bout givin' me th' rough lovin' neither; remember, Ah can take it, Ah promise. Jus'...whatever yer doin', Ah need it now!" Applejack virtually growled, feeling herself literally encased by his larger form and feeling his warmth on all sides of her as well as very deep inside her – needing him to do something already, her arousal uncomfortably high now as he simply stayed still inside her.

Trouble responded by pulling out and entering Applejack again with a rough hump, hearing her cry out softly. He was getting less nervous now at her sounds, not halting upon hearing another quiet cry as he pulled out and entered her again with a harsh thrust, realizing they were sounds of pleasure and letting himself start to get more into it instead of worrying about her. He was quite enjoying the warm, tight softness of a mare's passage surrounding him again for the first time in many, many months, as well as the rather cute whines and pleasured cries of the mare beneath him, his body finally feeling the full embrace of Applejack's innards once more.

"Ah Yer doin' –mmmh– y-yer doin' GREEEE-AT Sugarcube. K-keep at it!" Applejack encouraged, each pull out making her feel like he was dragging half her body out with him in the best possible way, each thrust in making her feel as stuffed as she'd ever felt. She was beyond satisfied as he started a pattern of slow but deep humps into her instead of the infrequent experimental thrusts he'd been giving her before, unable to help but constantly moan as his thick medial ring rubbed her clit with each thrust in, its re-entry bringing with it a snake of pleasure up her spine.

Applejack was somewhat disappointed when Trouble slowed down to a softer, slower pace for a moment a number of minutes in, her pleasure softening from the jagged surges to gentle ripples and her moans softening as she felt his thrusts become less forceful. Before she could question why he'd slowed, she suddenly felt him bite on her crest as a wild stallion would a few seconds later, her rather loud moan from that sensation echoing through the small room as she felt his thrusts suddenly increase in force. She felt his medial ring constantly rubbing her clit, whining again as she felt her pleasure swiftly rising, her passage constantly clamping down as she was given the best rutting she'd ever had.

"Goo-good gravy, yes! J-Jus' like that!" Applejack exclaimed, feeling her pleasure ramp up as her stallion started to get rougher, his love bite and less-than-gentle pulling on her crest sending tingles of pleasure and slight pain along her neck as her inner muscles started squeezing against him more frequently, making him lightly moan in turn. She felt so dominated by Trouble, so owned by this stallion in the best way.

From the way he was going at her, this was definitely not something anypony could call 'making love' – no, this was being rutted like an animal, being bred out of heat...and she loved it. Applejack groaned deeply as the bed started to rock with the force of Trouble's thrusts, with him apparently working on instinct to claim her as his.

"Ahhhh! Y-Yeah! Ahm yer mare! M-make me yer mare!" Applejack heard herself crying out encouragingly, her pleasure starting to really well up now, her hips starting to arc up against him to make his thrusts angled deeper, her lower muscles working hard to keep him as deep within her as they could when he tried to pull out.

A minute or so of the rough humping later, Applejack felt Trouble slow down to rest again; somewhat disappointed, but finding that she loved the soft, slow pace just the same as the rutting. Her pleasure softened again along with her moans as well, feeling his thrusts become slower and more meaningful.

Applejack then felt his bite on her crest grow looser as well before stopping altogether, with him apparently no longer working to claim her and instead planting tender kisses on her crest and neck now. She gave him softer moans now as she was pleased more lovingly instead, quite enjoying herself all the same either way but actually preferring this now. Now THIS was making love.

Minutes turned into what felt like hours, with Trouble switching between rutting Applejack like she was in heat to slowly making love with her, driving her mad with the variations of pace and positions. Every so often he would plant kisses along Applejack's neck again, making her shudder and breathe shakily, rolling her over on her back so he could start planting soft bites on her neck and kisses on her muzzle while rutting her hard.

About a half-hour in, in their starting position again, Applejack felt herself tensing up again, her inner muscles' squeezing starting to become more insistent as she felt her pleasure peaking. She was so close...so...

With a muffled, very pleased whinny into her pillow Applejack came hard, squeezing said pillow tightly with her forelegs as her inner muscles started working his penis inside her, unbelievably high swells of pleasure rocking through her as she buried her muzzle into the pillow and let loose another loud, if muffled, whinny. Her whole body was lightly trembling at the feelings surging from between her legs, her hips rhythmically grinding against Trouble on instinct, her widely-stretched muscles clenching as well as they could on the huge mass they contained as her mind blanked and her vision pulsed with white.

~

Trouble was forced to stop hilted inside Applejack as she climaxed, feeling her grip him incredibly tightly within her as she started milking him, unable to continue thrusting as her passage simply gripped too hard for him to even move within her. He easily held out as she came and remained deep in her, letting her feel him inside her during her orgasm, the pleased whines and quiet whinnies telling him she loved having something big and hard and alive to clamp down on during it. The feeling of her winking clit and the gush of wetness against his crotch once again told him he had pleased his mare well, knowing she'd likely reached orgasm because of him once more.

As Applejack finished her climax quite some seconds later she fell limp beneath him, panting and still lightly shuddering as she recovered. "W-wow Sugarcube. A–Ah ain't cum that hard in y-years, and never outside a a heat!" Applejack said in a slightly quivering tone, undoubtedly having to force the words out. Trouble nodded, gently kissing her on the cheek before she turned and brought her muzzle to his then kissed him. She kissed him for a long while before breaking it, then bracing herself again.

When she re-positioned herself onto her back again, made herself more available to him, and again gave him a nod, Trouble continued to mate his mare, starting slow before swiftly getting to a rutting pace again. Applejack could only accept each thrust as she was gently pinned against the bed, each deep thrust forcing her into the mattress a bit. "H-Hey S-Sugarcube, could y' stop please? Ah...wanna try somethin' else." Applejack suddenly asked after a few humps, an idea coming to her. Trouble really didn't want to leave her wet, warm body again but pulled out regardless, his soaked stallionhood slightly chilled by the air now as her mare-cum started to dry on him, getting up and now standing behind her.

Applejack got up off the bed and stood beside Trouble, slightly confusing him. "Ahl-right, mah turn. Lay on yer back." Applejack said, with Trouble nodding. Eager to continue, Trouble got onto the bed and lay on his back as asked, his breeding rod sticking tall and proud in the air. After giving it a pleased look-over, Applejack quickly got onto the bed herself and straddled over him, having to raise her rump rather high just to line herself up just right. Moments later, Applejack started to slowly descend on Trouble's cock without hesitation, swiftly making it disappear again into her wet, eager folds.

"Ohhh by Celestia! Yer the best stallion in all a' EQUESTRIA!" Applejack nearly shouted as she started to ride her stallion, feeling him going deeper than before into her as gravity helped her get him further in, his glans pressing tightly, and somewhat painfully, against her cervix with each measured drop she made on him. She felt that pain mix with her pleasure however, that sensation only making her keep going, making her want more and continuing to drop deep on him.

While she rode him, Trouble let his forehooves wonder over her body, feeling the tight, well-toned muscles he'd earlier only observed under her coat. As his hooves worked over her tight belly, he felt and watched the slight bulge his cock left as it went in and out of her, mesmerized at just how far open he stretched her and just how deep he went. He then moved his hooves lower and made her shudder, reaching them to her crotch and gently playing with her teats again. As his hooves made his way to her haunches shortly after, he felt as she put those powerful muscles to good work, roughly thrusting herself down on him, pounding him against her cervix each time.

"Ah yeah, get along mah little bull. Ahm gonna ride ya 'til Ah win a blue ribbon – er at least another cum!" Applejack said with a chuckle, Trouble responding with one of his own. "YEEHAW, GET ALONG!" she again called out, her next laugh interrupted with a moan as she hit a particularly sensitive spot inside herself on her next drop, thinking that was enough novelty for now and not enough rutting. She felt his glans starting to swell up now, his urethral process starting to softly tap at her cervix, making her shudder instinctively each time it did, knowing he was getting closer too if his body was preparing for the final step; inseminating his mare as deeply as possible by his process meeting or slightly entering her cervix. Judging by the rest of him, likely the latter.

Some time of riding him later, one of Applejack's back hooves slipped, making her drop sharply with all her weight onto Trouble, suddenly forcing his stallionhood deeper into her. "Ah BUUUCK!"Applejack cried out in an intense mix of pain and pleasure as she felt a very deep and sudden spreading, feeling Trouble bypassing something previous stallions couldn't have dreamed of even reaching.

Applejack stayed still for a while as her vision whited and her body trembled, soft, involuntary whimpers of both pain and pleasure coming from her between pants as her mind virtually exploded from all the sensations now rushing through her. As her mind came back to her and she felt just how deep he was in her belly, she realized what must have happened, no real doubt about it. Clyde had fully penetrated her cervix, full flare and all.

~

Trouble initially panicked when he felt that deep spreading of something very, very tight inside Applejack, feeling himself going deeper still and entering unfamiliar territory, knowing what that likely meant as Applejack then sat hilted on him now; hearing whines and whimpers coming from her, feeling her trembling but not knowing what it all meant. "Applejack, y'alright?" Trouble finally asked in a tone higher-pitched than normal, afraid he'd really hurt the mare straddling him. Soon after, and much to his relief, Applejack stopped whining and trembling and instead started panting hard as she then looked at him, her open eyes lidded and her tongue hanging out. The look of pure ecstasy.

Applejack answered by quickly meeting her muzzle with his, giving Trouble another deep, passionate kiss. A few seconds later she broke the kiss and nodded, then getting back to work lifting and lowering herself, moaning even deeper than before as she hilted him with every drop now, feeling his glans rubbing inside her very core now and her pleasure nearly unbearable.

The feeling of him being so deep inside her, stimulating every inch of her whole tract, made Applejack tense up again in no time, and with a few more downward thrusts on him, Applejack moaned deeply as her body went rigid again. "AAAAAAH–IIIIIM–AHM CUMMIN'!" Applejack squealed out, feeling her entire tract now literally suckling his cock and begging for his seed as she was overtaken by another mind–blowingly intense orgasm, her inner muscles kneading him of his life-giving sperm. She felt his flare swelling HUGE so deeply inside her belly, with his easily the biggest she'd ever taken, even among the other Earth-pony stallions she'd been with before; Earth-pony stallions well known for their huge flares and virility.

~

This time, the feeling of being so very deep inside his mare, hilted and feeling her milking him again finally set Trouble over, making him unable to hold back anymore as he felt his cock pulsing more, his flare swelling even more. "C–cummin'!" Trouble grunted himself as he felt that growing tautness in his pelvis snap, feeling Applejack's very womb grow tight around him as his head flared massively in her, hearing Applejack cry out again as she felt herself being stretched so deeply, his glan's ridges pressing into her womb's lining.

Seconds later Trouble let out his first massive gush of cum, his hooves tightly wrapping around Applejack's hips and croup in a tight hug as he felt the accompanying burst of orgasmic pleasure that joined it, holding her sealed against him as he came as deep into her as a stallion possibly could into a mare. Gush after gush was pure ecstasy for both as Applejack felt that satisfying warmth so deep inside her, feeling each hard spray through the condom and each hard throb of his cock along her entire passage, more then noticing as the condom started to balloon out as his cum inflated it – and her womb along with it.

Pop

As both heard that subtle popping sound, Applejack moaned deeply and tapered it off into an intense whinny as she felt a sudden flood of hot wetness explode deep inside her abdomen, her body going into double-time as she started to milk Trouble more as her third orgasm was set off by that warm, thick, creamy feeling so deep inside her.

Neither could think what any of that meant as Applejack remained planted on Trouble, feeling gush after gush of his warm, thick, sticky cum deep inside her womb with each throb of his...

Wait.

That wasn't supposed to happen. Trouble wasn't supposed to cum inside her!

He was wearing a condom, wasn't he?!

Applejack quickly pulled off of him with some effort, with his massively flared head swollen up and anchoring him inside her womb, continuing to pulse his virile load as deep inside of her as possible, making it a much more difficult than expected – and as she felt a sticky-slipperiness as she pulled him out, the sensation of a cum-coated stallionhood sliding out of her was quite distinct. "Ah horseapples..." Applejack cursed, looking back to see Trouble's whitewashed cock with only half the condom on it. "...looks like ya came inside'a me..."

Author's Note

Yep. They did the do in breeding season and the condom broke. Well at least she's not in heat, right?