The gray Pegasus landed front of a small house as she retrieved a small padded envelope from her messenger bag on a cool autumn day. She seemed to stretch her wings before folding them into herself. She approached the door and knocked like so many times before. And like always she also forced a weak smile. The door was answered by a common magic user standing almost a foot taller than Derpy, not counting the horn. In her normal day she had made it a point to not make eye contact, but sometimes she would, just to see, just to hope, that maybe this time she won’t get that look. The strained lips, the bunching under the eyes while looking away, or at anything else when talking to her. The look he was making now. “Package for Mr. mustang” she had said trying to be cheerful past the expected disappointment. He accepted the package without a word. And started to retreat into the house. But did not close the door before Derpy had started to turn around. He watched her as she walked away, and rightfully so. From any angle not including her eyes she was very easy on the eyes. Just the right amount of hourglass figure and exquisite hindquarters that would place in any contest. But perhaps her most noteable asset was her rack. Larger than average for most mares but that meant absolutely huge for a pegasus who were typically very flat-chested. All Pegasus tended to be very short and ‘aerodynamic’, which had become a euphemism for a chest that did not require a bra.
Stepping away from him in her backless shirt, a very common shirt for a Pegasus. Well, common for a female Pegasus, most of the male Pegasus are most often found going shirtless whenever they could. Actually all Pegasus preferred shirtless, and pantless, and all other form of garmentless. At least when flying. Something about the wind and the way it rolled along their bodies tickling some deep instinct that none could explain their aching for. Often this itch would be fully scratched at night when it was safe-ish to risk the flight without running afoul indecency laws. The next best thing in daylight was thin, flimsy, lose fitting clothing. This meant the clothes could wave like a flag in a breeze allowing for a cheap imitation of nude flying. It was better than other clothing, including the ultra tight catsuits of the wonderbolts. Who only wore them for photo events and for the performance they offered at the high speeds necessary for the acrobatics they did. But they very much hated them, often resulting in all of them stripping bare in front of each other before the locker room doors were even closed. At least that’s what the gossip magazines would claim.
The unicorn just ogled her as much as he could while she chose the next address. While he was leering he could not help noticing her bra strap, and how it ruined the lines of her otherwise very shapely back. Always a trashy look to have the bra visible, but made worse by the backless shirt. Like socks with sandals it signified this person does not care about their appearance. But that was not the case for Derpy, she needed a bra, and she needed the backless shirt for her wings. This fashion faux-pax did not help her reputation. Her crossed eyes, her slightly clumsy demeanor, and her misunderstood ‘fashion sense’ otherwise made her a social outcast. Except for this, the next name on her package delivery tour. Applejack, well any of the apples really. It wasn’t so much AJ that Derpy was excitedly jumping into the air to take flight, so much as it was the brother. Whenever there was mail to take to the farm it meant Derpy would have a chance to see Big Macintosh. Perhaps a silver lining to the curse of her eyes was that she could always tell if someone had a kind soul. By simple virtue that they did not look away or squint or outright cringe at Derpy. Big Mac was one of those souls that made the short list of Derpys favorite deliverys.
More than just a kind soul Big Mac was easily the most visually pleasing stallion this side of Equestria, maybe even in Canterlot too. And while standing next to him two feet under his full height was a treat all unto itself for any mare, it was all the more special for Derpy who immediately after visiting the stud had learned to go straight to Sugarcube corner. Flying there straight from the farm was always the highlight of the week for Derpy as she was often the only one to see the farm isolated stud most weeks. Mares had learned the unofficial ceremony of Derpys flight from the farm straight down mainstreet to the corner. If they were nearby and had seen her, there would be a small stampede to gossip about the stud and just what his choice of clothing was for the day. Was it a plain undershirt? His Rarity fitted flannel? Or perhaps the greatest of occasions when the day was a hot one and he would be as bare-chested as he was in their dreams? Such days Derpys face would be as red as the gossip target. She played such events up a bit to encourage more small-talk, usually about what he was working on but more often was the smell of the hard working stallion. Which would usually result in a few mares immediately trotting out to the farm for a few extra apples, an ‘unexpected party’ being the usual excuse. It was by far the most social interaction she would ever get any other time. For that alone she would forever hold the stud a special place in her heart.
Derpy was flying just a little higher than normal to reach her next destination. But she needed to, so often the Apples were out and about on the farm. Her eyes may have been crooked but her vision was as sharp as any falcon, appropriate as she felt she was scanning for her prey. If she happened to spot the two luckiest mares in ponyville she would make a note of it in case she reached the house before spotting Big mac and he wasn’t home. But there was no sight of anyone. In her excitement while approaching the farm house, she had landed a little harsher than she wanted. *Snap* went the bra. The bra was well engineered for anyone walking on the ground. But not so much for the rare well-endowed pegasus flying in the horizontal. The bra having to deal with the full weight of her bosom, combined with stiff landings her bras didn’t last long. She quickly and quietly slipped it off which was not a challenge in her backless shirt. But the last time it happened she had forgotten to replace her spare. Her arousal peaking now that her thin shirt was a little more pointy than normal, blushing hard and feeling far more exposed than she was used to. She took a deep breath stuffed it in her bag, brought out the small box and got ready to knock on the door.
She was now knocking for the third time. Two times was the most typically afforded most mail recipients. But this was a chance to see Big Mac, a third wouldn’t hurt. But there was no response. Feeling slightly defeated by the empty house she began to flap her wings and fly back to town for her next stop. She was so disappointed, but that’s life sometimes, ignoring you when you are down. Derpy decided to have a rest anyway, but not at sugarcube corner. She didn’t want to share her disappointment with the other mares of the town as they rushed her for news. Fortunately she knew of Rainbow Dashes favorite ‘I’m not sleeping!’ spot on the farm, and that tree wasn’t really out of the way at all. She still kept an eye out, scanning in case she might still have a chance to interact with Big Mac. As she approached and descended to the tree she still kept looking out over the farm in what was a desperate final hope to catch him. But then, a moment before she had expected to land on the tree she realized her horrible mistake. In her desperate search for the stallion, she had completely neglected to even look at the tree she was approaching, if she had she would have noticed the resting spot she was seeking was in fact occupied. And not by some cyan pony but by the hulking red beast himself.
It was too late, the collision was already happening. She felt her full weight press into the stallion. He though for his part was not completely asleep, eyes closed he did not see the incoming disaster. His wits though, sharp as could be. Without skipping a beat he shoved is leg into a split in the branch giving him the purchase he needed to keep his balance, and now also the balance of an unexpected pegasus. He quickly placed one hand under the branch and his other hand on the small of her back to keep her steady and hopefully prevent her crashing to the ground. She had briefly tried to flap up to get herself off him but it was a futile effort as perhaps Big Mac did not know his own strength. He kept her in place resting squarely on top of him. As Derpy realized her situation she couldn't help but be aroused again. She now having stopped her squirming noticed the stallion beneath her was in fact shirtless, a fact accentuated as her harding nipples were making themselves known to Big Mac though her thin shirt. They struggled to stay hard against his warmth. Then it was the warmth of his hand she noticed next, firm against her back. The strong hand not just keeping her from falling but also kept the rest of her body in close contact with his, her slender body yielding to his washboard abs. She could feel her heart rate increase, the blood rushing to her face. There were no words, all she could do was stammer sounds that had a vague resemblance to speech. And all that handsome bastard did was give her that usual stoic smile that he always had.
Derpy continued to try finding the words to apologize for the impromptu lesson in why one should look where they are going. She continued to fail, but her series of half syllables were soon silenced by the appearance of another hand on her back. This one slightly higher just below her wings, but more importantly followed by the first hand slowly making its way down to her haunches. This couldn’t possibly be, it couldn’t possibly be that ponyvilles most eligible was giving a signal like this. Derpy was wishing she had more knowledge about initiating sexual situations. The odds coulden’t possibly be in her favor, but the payoff was too high to ignore. She gently, slowly squirmed again, this time bringing herself up, face to face with the stud. But before she knew it his smile was gone and he was closing his eyes. She closed her own eyes knowing the object of his displeasure and began hating herself, for giving herself the hope that she could be so lucky. She could feel the sadness and fear welling up in her, the fear that she would in fact be alone forever. She was about to squeeze out a single word apology and fly away before it happened. A warmth against her lips. Her eyes shot open and indeed there was no mistake, he was sharing his lips with hers. She reclosed her eyes and began to tremble as she returned the kiss, feebly as she could, practicing with stuffed animals didn’t leave much for feedback on the improvement of her kissing skills. But she did her best and he gave no sign of disapproval.
It was only a few seconds, or maybe half an hour, she had completely lost track of time for the most passionate kiss of her life. Before long Big Macs two hands were both at the small of her back again, between her backless shirt and capri pants. This time they pressed firmly against her, fingers tracing around her pronounced dimples of venus, a feature Big Mac had a secret weakness for, a feature always on display with pegasus. Making their way down the firm yet shapely rear of the gray mare, this time under her pants and her underwear. His intentions no longer in question made Derpy sit upright, and take the unbelievably bold move to untie her shirt. First untieing the bottom, then at the top. She lowered the top slowly, nervous as can be for a first time exposure. But exposed she was now, her own smile grew to match his, little bigger than his usual stoic smile he was quite pleased with what he saw. His hands then move to inspect the beautiful orbs, thumbs orbiting, massaging the pink nipples. From her new seated position legs now dangling, fully sitting on the stallion, she now felt a growing warmth bulging beneath her tail. She took a deep breath at the size of the beast she felt now trying to free itself from its confines. She turned to see the prominent bulge placing a hand on it and surprised at the warmth radiating through the pants.
She placed her knees on his abs to better raise her hips to better reach the button and zipper keeping the most oft gossiped member of ponyville hidden beneath her. While she fumbled with the out of sight button, Big Mac made quick work of her own button and zipper and then finished his zipper after Derpy managed the button. She slipped her pants down to her knees as Big Mac raised his buttocks to lower his, his member now fully free but still growing behind the mare. She needed to sit in order to remove her pants, and sit she did. She felt the flesh of his shaft split the lips of her soaked nethers with ease as the medal ring pressed even firmer into her nub. She had to take a moment as this was the first real contact with a stallion, or anyone, a moment she thought would never happen.
She had to fight the urge to cry, and she did well. Only a pair of small tears of joy could be seen, but only if you looked closely. This was the first time in her life that she felt sexy, that she could be more than her eyes to someone, she stretched her back and curved her spine as she began to grind on the meat of the stud beneath her. During the brief grinding she had looked down only to freeze with fear, or awe. The meat she was grinding was so much bigger than she had expected. Was this thing really supposed to fit inside her? Was this going to be a back door adventure? She didn’t know, all she could do was let him take the lead. Seeing her hesitation at his size he took one of her hands and placed it on his shaft, where she felt his warmth coated in her juices. He then grabbed behind her knees and slid her forward exactly to where she hoped he would stop. With her silken entrance right above the head of his member. She began grinding again coating the dry part of the shaft quickly, but not enough to get the penetration she was so aching for. Maybe it was the angle or perhaps she was too tight to allow such easy entry.
Big Mac sought to remedy both problems as he grabbed her shoulder pulling her down into a boob squishing hug with one hand and firmly taking one of her buttcheeks in the other hand. He could feel his shaft was now in the perfect position, and adequately lubed. He began to press her down while also pushing up into the untouched mare. Fortunately, he was not fully stiff or this would have been more painful for the tight mare. Just soft enough to make it past the lips and rest the head just inside the nervous mare. It was already the most pleasure she had ever known. Mouth open she wanted to howl but was too focused on the sensation, trying to memorize every detail. She finally noticed that he stopped, he had noticed the sudden tightness to her tunnel. He smirked as if to ask ‘ready?’
Reaching up she could only respond with a kiss, brief yet sweet. She then moved with his direction to tear the last vestiges of her loneliness. Now with nothing in the way he began the slow dive into her warm silky passage. She was reeling in sensations, the warmth of his breath, the musk of his body, the strength and gentleness of his hug, and now the heat of his shaft as it spread her most sensitive of organs in the most lewed ways possible. He was taking her slowly, giving time for the juices to spread and give the best coverage possible. Then came the medal ring, it didn’t require more effort but it was a momentary highlight as it lightly kissed its new friend entering her passage. Derpy squeaked as it entered. But he hadn't slowed, he was surprised that she was taking so much of him, but then again he was only just reaching full stiffness. Derpy was barely clinging to sanity as the fullness of his shaft filled her so completely, as she finally hit the base of his shaft. There was so much in her she felt like her breath had to be shallow to accommodate his size. After a moment to let the sensation settle, Big Mac began in earnest. Rocking the gray mare back and forth, his shaft came out just enough for the ring to be felt sitting outside her entrance before immediately getting shifted back inside.
It didn’t take long for the Pegasus to straighten her wings signaling her partner that she was about to burst with pleasure. She began twisting and twitching under his embrace. Clenching his member as tightly as she could within her body. Big Mac had stopped the rocking so she could ease through her first orgasm without risking hurt to the inexperienced mare. As she came down from the overwhelming sensation, she began to notice he was still buried fully within her, still stiff as when they started. She bit her lower lip showing she was eager for more. She sat up, still fully filled, and began shifting her legs over and around the stud until she was positioned facing away from the stud, giving him a view of her backside. She had always considered her own backside to be her best angle, confirmed when he massaged and traced her curves earlier in their little session. And he began massaging them again. Her shapely behind pressed against his groin was a sight indeed for the stud as he seemed to throb in her tight passage. She wasted no more time and began lifting herself up wings flapping, letting herself drop back to fullness. The sight and sensations was going to be a losing battle for the stallion as she pulled her tail to the side to let the stud watch his member disappear fully within the shapely mare.
The deep red beast wasn’t the only one set to lose his battle with pleasure. Big Mac wasn’t the only one treated to a pleasing sight. She had looked down to better see the balls of the stud only to notice the intruding member of the stallion was bulging her belly with each intrusion. The new sounds of their most sensitive regions slapping together was an unexpectedly erotic trigger for the gray mare. She was desperate to find a new thrusting angle to make it last longer, she even tried slowing down her pace only to find his grip tighten around her waist in protest as he took command of the thrusting. His strength lifting and dropping her without need of her wings to assist. She was already losing her own battle and now was being rushed over the edge. Letting out a moan and again stiffening her wings she was joined in her choir by Big Mac with his own deeper groan indicating his approach to the edge. Not but a few thrust later and the slapping stopped as Big Mac pulled her down for one final thrust, the deepest thrust made so far. She felt his head throb and grow inside her instinctively knowing what this meant was the last straw for Derpy. As his hot seed flooded into the burning mare, she began clenching in concert to his throbbing. The first pulse of fluid filling the remaining crevices before the flared head forced the second, third, and following pulses into the eager womb. Derpy had thought when they started she was a full as could possibly be, this new flooding sensation was an unexpected delight that stacked another orgasm on top of her current blissful convulsions.
Now Ditzzy with pleasure she managed to turn around again and rest herself on the chest of the stud beneath her, she shared a kiss with him as they settled from the mind numbing pleasure. As he softened she could feel the seal his member made in her break as the torrent of seed deposited now had a free escape. She clenched in a vain attempt to keep as much inside as possible. After a few minutes they seemed to catch their breath and could feel each others heartbeats settle, Big Mac gripped her into another hug as he lowered them to ground level so they could retrieve their dropped clothing. Now standing she could feel the weight of his seed inside her and its warmth as it drooled down her inner thigh. Realizing she would need to go home for a change in clothes or the cumstain would be visible, to say nothing of the delightful smell as she sneaked a taste while dressing. She gave him a final hug and grabbed her bag to go home. As she flew off, somehow, she knew she was now a mother, smirking at the thought she went there to give a package and got one instead. Realizing she still had the package she almost turned around only to realize it was a great excuse to visit him tomorrow, and if she was lucky, she would forget to deliver that package again.
Author's Note
I fell asleep the day we covered fanfiction dialogue in english class.
