A Glass of Bubbly MILF

by Steel Quill

Rating: mature
Tags: Slice of Life, Featherweight, Anthro, Porn, My Little Pony: Friendship is Magic, Fetish, Romance, Derpy Hooves, Sex
Length: 9847

For this New Year's Celebration, Featherweight finds himself in some motherly, loving company.

When you celebrate New Years, you can always expect a few things. There's the grand celebrations all throughout town to ring in the new year. There's feasts, and drinks, and plenty of merriment to go around. Even a few explosive fireworks, usually placed safely. For Featherweight, he wants to try and capture the high spirits of New Years to show his photography skills and celebrate in his own way. But when everypony he talks to is apparently too busy to help him, he's left feeling a bit adrift. But fate has other plans in mind, in the shape of one caring, wonderful, bubbly mail mare.

A for-fun New Years themed story I came up with on the fly. Pre-read/edited by Sockpuppet! Artwork by Longinius! Featured 12-31-21, thank you! And happy new year!

Kinks/tags: MxF, New Years theme, Age difference, older mare/younger stallion, MILF, first time, Huge tits, tender sex, grinding/dry humping, oral, blowjob/deepthroat, titfuck, cunnilingus, cowgirl position, tit worship, sex positivity, v-card cash in, cumshots, creampie, one damaged chair, happy ending.

Published 2021-12-31 16:30:01 UTC
Last updated 2021-12-31 16:30:01 UTC

A Glass of Bubbly MILF

You’d never think a town like Ponyville would actually run out of people, but it was a problem Featherweight found himself facing while wandering through the town square.

The amateur photographer had come up with a fairly simple idea: New Year’s Eve was right upon them, and one could see plenty of folks setting up their own celebrations. The market stalls were already starting to close up, eager to get to their own celebrations and parties. Almost every few feet, you could see somepony carrying grocery bags full of food and drinks for tonight. Heck, it was already news all over town how Applejack had sold off her whole cider stock in a matter of hours, earning her family a fairly nice end of the year mint. Featherweight was sure at one point, he saw Trixie planting mortars on the outer limits of town, but who knew what the stage magician had in mind?

It was the perfect opportunity to work his photographer magic and build up his portfolio by doing some holiday work. And you’d imagine that surely there’s a pretty mare or two who might want a proper photo done before the drinks hit too hard later on. But as Featherweight came to discover, there wasn’t as much interest in a freshly 18 year old amateur for family pictures. Pictures had already been made early on, or they just weren’t interested, even with him offering to do it for free.

“C’mon, man,” Featherweight muttered with his gaze downcast at the dirt path before him, “can’t a guy try to make his mark somehow? Even Tiara said no, and she takes every chance she gets to be in the spotlight. What’s a guy gotta do to - Oof!”

Featherweight found his train of thought and his world go sideways as he collided unexpectedly with another body. Being on the slim and shorter side as he was, he didn’t have a lot of mass to try and resist with. He fell to the ground, protecting his camera at the expense of his back, and groaned for a moment before righting himself. “Sorry!” He declared.

“Oh goodness, I’m so sorry! I didn’t see where I was going!” The female voice felt familiar to Featherweight’s ears, the brunette looking up but finding his vision obscured by Celestia’s sun overshadowing her. Only when she moved closer and squatted down in front of him could Featherweight see who it was, and who it was had him paying full attention.

“M-Mrs. Hooves!”

“Featherweight? Are you alright?” Her concerned tone matched the pleasant voice that the stallion could now place. One of the more present figures around in his life alongside his childhood friends, Derpy Hooves was always like the extra mother everypony had and cherished. He went to school with Derpy’s daughter Dinky, and Derpy had always been an active school parent.

The blonde pegasus’ pretty features were turned into an expression of concern as she inspected him still sitting there on the ground. Blonde wispy hair was brushed back, kept out of her face in a semi-cowlick style that suited her. She kept it cut to just past her shoulders, so it wouldn’t blow in her face when she flew, he recalled. The motherly mare wore a pair of glasses, which didn’t quite solve the dilemma of her wandering eye and yet looked cute on her. Take into account the earrings she had and the light touch of lipstick, and you could tell she was a mother.

If you went off the rest of her though, some could argue she was a mom from your private dreams.

Featherweight had done his best to be a good mannered kid growing up, but no colt going through puberty could ignore the kind of figure Derpy boasted. Even standing upright, she was taller than him by a good head and a half, putting the smaller pegasus’ view at chest level. And Celestia, what a chest. Even the bulky winter sweater Derpy had on couldn’t hide the bountiful bosom she boasted, only serving to make her look all the more homey and appealing. Combine that with the healthy, wide hips and long legs complimented by her faded jeans, and one can see many reasons to be distracted by her.

“I-I’m fine, Mrs. Hooves. I wasn’t paying much attention to my surroundings,” He replied, “I didn’t hurt you, did I?”

“Nope!” She smiled wide, relief crawling into her as she folded her arms over her pronounced chest. “I was just busy thinking on tonight. It’s New Year's tomorrow, can you believe it?”

“It sure doesn’t feel like it. I feel more like I just got done with Nightmare Night just a week ago!” He joked.

Derpy laughed into her palm and shook her head. “Time always flies when you’re having fun. Heck, it flies better than I do most days!”

Featherweight chuckled. “So what brings you out here? Everywhere I’ve gone today, I see ponies with bags full of snacks and meals for tonight. Did you get yours already?”

“Oh, I don’t need all that much. With Dinky off with friends and my coworkers occupied, I don’t really have to prep for anypony this year,” she explained. “So really, after cleaning up at home, I thought to get out and have some fresh air. What about you, Feather?”

She always called him that. It felt like an easier nickname for her to remember, not that he minded. Seeing her smiling expression made him feel happier inside. “Well, to be honest? I’ve been kinda bummed. See, I’ve been trying to get some more of my photo portfolio made, right? Like that Spring set I did a few months back.”

“I remember those! Dinky told me about them, they looked so pretty! You made Ponyville park look so much brighter and colorful than I thought it could be. You’re so talented with that camera of yours!”

Featherweight felt his cheeks warm at the praise from the pretty, older mare. “Thank you, ma’am. But I needed more than just those. A portfolio has to have range, so I’m trying to include other things too. But I’ve run into a problem; nopony wants me to be their photographer tonight. So I’m kinda at a dead end.”

“Aww! I’m so sorry, Feather. You work so hard at that,” Derpy lamented. “No one at all?”

“Nope. Seems I’m a solitary soul today,” Featherweight replied, only to pause and look at Derpy again. The woman was busy looking to fret, as if she needed to be ready for a possible helping hand to give to Featherweight. But in his eyes, the helping hand was right there in front of him.

“Say, Mrs. Hooves; how busy did you say you were again?”

That evening

Standing just past Sugarcube Corner, Featherweight waited patiently for Derpy to arrive. He hadn’t dressed up too much himself, merely adopting a button up long-sleeved shirt and black pants. Keeping it simple like that made him feel more relaxed than wearing an entire suit like he’d seen others do. There was plenty of foot traffic at the business, with ponies going to the Pinkie Pie party in the front but some going to the back to pick up catering for their own parties back home. It was the perfect kind of scene to snag in some shots that he wanted, and with Derpy as well.

Part of him still couldn’t believe he’d asked her to be his model. It was out of the blue to him, but in all honesty, it was an idea he was warming up to. He’d harbored some affection towards the mailmare and all-around neighborhood figure ever since he was a kid. She was kind to him always, mindful of his health and always being a positive supporter even when others wouldn’t have. She was the neighborhood mom, and now he had the chance to do a kindness for her and let her be the star of his photos.

“I’m here! I made it!” Derpy’s voice called out to him. He turned to his left and saw the pegasus approaching, almost stumbling as a heel caught in the road but catching herself in time. He had to remind himself not to stare too hard: Derpy had gone and fit herself into a black number that hugged her curves almost too well. Featherweight’s trained eyes could tell that the dress was a comfortable fit on her, and tailored for her figure from the way it didn’t hike up or stretch too tight over her middle. Her lower half let her legs show off, a pair of stockings slipped on over her legs and a pair of heels to walk in. Her upper half was a bit teasing, but kept decent thanks to the white sleeved and thin jacket. Even with that, there was no disguising Derpy’s blessed proportions.

“Hey!” He greeted when she did reach him, smiling up at the older mare. She’d foregone her glasses and even did a little makeup as well, a touch Featherweight appreciated from her. “You’re looking wonderful, Mrs. Hooves. I feel under-dressed in comparison.”

“Oh, stop it,” she dismissed with a wave, but smiling at the compliment, “I just had this in the closet and thought it might work. It’s a real big show in there, it sounds like.”

He had noted the ambient noise as well, but tried to take it in stride. “Well, it is New Year’s Eve after all. If there wasn’t some noise, you’d almost think something was off.”

“I guess so. I’m not too much for noisy crowds. I used to be, but an older mare like me gets wore out now sometimes.”

“You’re not old, Mrs. Hooves.” He said before pausing and clearing his throat, “I mean, Derpy. I bet you’d prefer that.”

“I would, actually. Thank you.” She agreed with a smile at him. Her happy expression made something stir in him, and he turned aside before he imagined he’d be blushing.

“Now, the easiest way to make this work is just spur of the moment timing. People are celebrating, having fun, ready for the new year. So all we have to do is get in, snap some shots together with some willing folks, and then we’re free to enjoy the rest of the night.”

“Ok! We can do that!” Derpy clapped her hands together. “I just hope I don’t break anything this time. Last time, I had to pay for a few tables. And glasses. And replacing a prosthetic leg.”

“I’m sure nothing will go badly here this time. We got this.”

It was an hour later that found Featherweight almost stomping out of the building, Derpy following after him albeit much more contained, if perhaps a little downcast. The male pegasus had the will enough to put his camera aside before sitting down on a nearby bench and resting his head in his hands. Derpy was there beside him a moment later, and brought her own hand onto his back in a consoling fashion.

“I’m so sorry, honey.” Derpy said softly, prompting Featherweight to look up at her.

“It’s not your fault. You didn’t do a single thing wrong. Those people in there, half of them don’t even live here. And the ones that do, I mean…come on!”

*********

“Hey Pinkie! Pinkie Pie! Can we have a photo-”

“Maybe later! Gotta prep the party cannon for party people and party ponies! Then when the fruit punch runs out, we’re gonna really have fun!”

“Ok, but it’d just be for a minute, you’d actually like this and-” Featherweight was cut off as a small sea of ponies suddenly hovered Pinkie away, leaving the pegasus to watch as she vanished amidst the crowd. A feat, given how much she usually stands out.

“...ok then.”

*********

“Hi, Mrs. Rich, would you like to-”

The fashionably dressed and permanently resting bitch-faced earth pony took one look at Featherweight and Derpy, gave a single sweeping observation of their attires, and slid back at least two steps before giving them a haughty look in silenced judgment.

“I think she’s wanting to be left alone, Feather.” Derpy said, tapping his shoulder. “Let’s try someone else.”

*********

“Listen, guys, I just need one good group photo and then you can go on your way. C’mon Rumble, you owe me.”

“Hey, ish that, ish that Derpy Hooves with chyou?” Rumble questioned. His standing sway told Featherweight the pegasus had been at this long before the gathering had even started.

“...yeah, it is, so what?”

“W-where's Dinky?”

“Oh, Dinky is off and out with friends tonight.” Derpy replied, taking a mindful moment to move behind Featherweight. “This party is definitely nuts, huh?”

“No don’t say that-”

“Dinky dese nuts!” A nearby Button Mash said, making both stallions laugh in drunken humor.

*********

“I’m so sorry about them. They were rude, and drunk, and just…I’m sorry.”

“It’s alright, really! I’ve seen and heard worse things than a few rowdy kids,” Derpy assured him. “I’m just sorry your plan didn’t work out. I guess everypony’s just kinda stuck in their celebrations, huh?”

“I know, just…I’m sorry if I wasted your time.” He told her, looking up at her again from his lap. “I imagine this is hardly fun for you. I mean, here you are looking fantastic, and yet those ponies couldn’t spare two minutes to stand still. Don’t even get me started on Spoiled in there.”

“Yes, well…she always was a bit of a sourpuss,” Derpy noted.

“That’s to say the least. Like a walking figure of expired milk.”

Derpy giggled at that, and the pair was left quiet for a moment before Derpy spoke up. “What’re you gonna do now, Feather?”

“Well. Frankly, I don’t know.” He told her, looking out at the town while he spoke, “My folks are away today, out of town. My friends are in there being drunken idiots. Which, again, sorry.”

“No harm done.”

“Really, I’ve got nothing. What about you, Derpy?” He asked. “You said Dinky was out doing her own thing. So what does that leave for you?”

“Well…” she trailed off, making him raise an eyebrow, “...to be honest? I really only had the thought to get out a bottle of wine, maybe some cheesecake, and just see what comes on TV tonight. I’m not…all that much for big crowded areas or parties. I tend to cause accidents in one way or another. So tonight might be better for me to just keep things on my own. Dinky is able to celebrate with the Cutie Mark Crusaders in Canterlot, seeing the Princesses ring in the new year, so I’m happy she gets to do that.”

No. This just wouldn’t do.

“I got a better idea.” He declared, standing up and making Derpy look at him in surprise. He held out a hand to her and she looked down at it, one eye still looking elsewhere before she gazed back up to him.

“If everypony else is gonna go have their own good time…then we can go have one ourselves.”

“Ourselves?” She repeated.

He nodded. “To be honest, I can stand having my own night not go well. But I can’t stand seeing somepony I care about have no chance to celebrate. And since we clearly don’t do well with these crowds, well, then I say we make things go our own way. You can come by my place, and we can do…well, whatever we want to to celebrate. Pictionary, Gin rummy, whatever you might want to do.”

Derpy seemed genuinely surprised at first, but a smile crept onto her features after a moment. “Are you sure you’d want to celebrate with an older mare than with friends your age?”

“The ponies here didn’t deserve to be in a photo with somepony as lovely as you. So if they won’t take up that chance, well…I will.” He declared. As he spoke, he kept his camera pointed at her. Even if he wasn’t taking photos then, it still felt natural, keeping the large diameter lens in her direction. It was a much bolder declaration than he had meant to give off. His cheeks burned a little under Derpy’s stare, but he felt himself relax when she took his hand gently and stood with him. For a moment, her other hand reached over and caressed the camera he was holding, as if the item was making her decision for her.

“Well then, Featherweight; what’re we standing around here for?”

She smiled. And he smiled back, the night suddenly looking better in one single expression from the mailmare.

There weren't too many games one could do with only the two ponies to play for New Years. But in a way, it seemed to be better that way from Feather’s perspective. Sure, most folks would rather have a lively, noisy house with multiple people having a party and being ready to celebrate the new year. But given what he and Derpy saw outside, this was much better for the pair of them. The older mare seemed to be more relaxed with just the two of them, and had fun doing the games they did play out. Darts, ping pong improvised on a dining room table, even playful charades that had both of them laughing at the silliness of the other was a breath of fresh air.

By the time they were getting closer towards the final half hour before the new year would arrive, he and Derpy had gotten into a little bit of the celebratory wine. The pair kept the drinking light, since Feather was new to it and Derpy herself admitted she wasn’t much of a drinker either. Stories were shared between the two, and Feather couldn’t shake his grin off no matter what could’ve happened. “So you managed to somehow bust through the wood stage and all the way to the basement, but not a single scratch?”

“I know, right?” Derpy laughed, jostling her wine glass a little before settling. She’d foregone the white jacket while indoors with Feather, exposing her arms and the upper half of her chest. Feather was making a conscious effort to not look down at times, as whether Derpy intended it or not, the dress made her cleavage only more pronounced. “Rainbow made a lot of jokes about it. But I’m just happy nothing else broke. I don’t even know how I did it!”

“I’d rather you not be hurt either, frankly. If that happened to me, I’d probably have a broken arm or something with my luck.” He said. In front of him and her, the TV was set to a broadcast out of Canterlot, where masses of ponies lined the streets and shops leading towards the castle district. Although they weren’t there themselves, one could still easily sink into the view of seeing the large, lit up city with all its revelers. Feather gestured at the screen with his glass. “Do you think you’d ever see yourself out there in all that?”

“Only with friends, and even then, I’d keep off the street. To tell the truth, I’m never one too much for being front and center. I’m used to watching from afar, for some obvious reasons.”

He looked over at the mare and saw her gesture with a finger at her wandering eye, making the stallion shake his head.

“I can get that. It’s never bothered me, as a truth from me.” He told her. “I just see you, Derpy.”

“I’m glad. Growing up, there were an awful lot of ponies who liked to crack the odd joke or two behind my back. Sometimes I could laugh it off with them; I mean, I’m not exactly a crack shot or ball thrower,” she said while leaning back against the sofa, “and sometimes I’d go home and wonder if I could ever afford an operation to help myself. But I’m thankful there’s folks like you who don’t mind it.”

Feather nodded and tried to think of what to say or carry on from there. It clicked in his mind suddenly, and he pointed at the busty mare to get her attention. “Hey. Let’s try one more game, for fun until they start the countdown.”

“Ooh! Whatcha got in mind? It’s not creative darts again, is it?”

“Forks work just as well as darts with enough force,” he insisted, earning a snicker before he continued, “but what about a good, old-fashioned truth teller game?”

“Hmm…alright. But no mail secrets; I have a job oath to uphold!” Derpy proclaimed while straightening up and raising her right hand, as if defending some great honor in the postal service. Really, all it served to do was make her chest stand out more, making Feather momentarily distracted before he focused again on her face.

“Alright. So you can go first, and we’ll use the songs on TV,” he gestured at the display showing Coloratura on stage setting up, “as our timers. Until the song is done, you can’t say an untruthful thing about something or somepony. Could be coworkers, could be about work or Ponyville, anything at all.”

Derpy smiled at his idea and nodded. “Hmm…then I’ll start with saying thank you,” she replied as Coloratura started to sing in the background.

“Thank you? To me?” Feather questioned.

“Mmhmm. Because you’ve been the most genuine stallion I’ve seen in months,” she said, sipping from her wine again before continuing. Coloratura's voice carried on, but Feather tuned in harder to Derpy speaking. “Most guys would be bored with me, or making fun. Among other things. But I’ve watched you tonight and it reminded me of all the things I’ve liked about you growing up. You’re honest. You’re passionate about what you do. And I admire somepony willing to go after their dreams and take that chance I never could. I want to see you succeed, because even if I am just a neighborhood mom and mailmare, I can still care. And you all deserve the best you can get.”

Feather was left genuinely surprised at the sincerity coming off of Derpy, directed at him no less. He didn’t think he’d mattered that much to the pegasus. “I…I didn’t think you did care that much, Derpy.”

“I do. I care a lot about all of you. Just because the world likes to be mean and sassy sometimes doesn’t mean you can’t be kind to others,” she replied, smiling at him. His cheeks colored and he tried to search for something to say in the remaining depths of his wine glass as he drank from it.

“I also imagine I’m a distracting mare to look at sometimes. For two obvious reasons.”

This made Featherweight cough into his glass, splashing cabernet on his front and making Derpy laugh right as Coloratura finished her number to applause and confetti on her stage. Featherweight spluttered and pouted over at the amused mare.

“So not fair! C’mon!”

“You said to tell the truth! And I did!”

He barked out a laugh at that, and so did Derpy. When he settled, she looked at him expectantly, making him take a moment before he realized - with a gulp of trepidation - that he had to take his turn. He looked at the TV set, and saw another musician going up but the tempo of their song suggested a longer piece.

“Ah. Alright. Well…” he trailed off before taking a breath and just letting his words flow out. “I think I’d like to say the same as you, to say thank you. Because you’re willing to spend time out of your night with somepony like me. I knock myself sometimes because I can’t help it, but when I look at you, it makes me think I’m a really lucky guy. Here I am with this heart-of-gold, beautiful, nicest mare I’ve gotten to know. She could be with anypony else right now, but I got the fortune to be next to you tonight. Frankly, I’d say that’s a blessing more than anything. Because…because I think you’re just really wonderful. In all kinds of ways.”

He kept on as the music filled the room from the TV, keeping his eyes on the coffee table. “A lot of guys my age don’t notice it, but I pay attention to my surroundings. You put in so much work to keep a good life going for Dinky and yourself. You dedicate so much time for others, and sometimes, they can be downright jerks in response. And yet you keep smiling that beautiful smile. You inspire a lot of us to keep going when we think we can’t. If I was to pick any sort of mare who’d be a good role model, it’s you.” He stopped to drink from the wine glass, absentmindedly noting the song was taking forever to finish.

“F-feather-”

“And that’s not even going into your looks. Beyond the obvious things, because I can think with more than just one part of me. Any stallion worth their salt would know they’d have the best in you, because you do your best all the time. I’m used to being alone, and it’s something I’ve grown up with being an only child in my family. But you deserve to have the best. And to not be alone. I’m not some like, studmuffin, but…if it was me? I couldn’t ask for anything else.”

The song finally ended, and Featherweight sank back into the sofa. He looked over at Derpy and did a double take, seeing her eyes looking watery and a tear streak on the side of her cheek. “Derpy? Oh, shit, did I say something wrong?” He sat his wine glass aside and turned to her, a hand meaning to reach for her cheek. She caught his hand, but held it there between them for a moment. “Derpy?”

“Do you mean it?” She questioned. Her voice quivered with emotion, and Featherweight didn’t dare look away from her. “Do you?”

“I meant…every word. I wouldn’t lie to you. I couldn’t.” Featherweight said. He squeezed her hand as a means of reassurance.

“E-even with…you know…” Derpy gestured at her wandering eye.

“I don’t see problems,” Featherweight replied, looking her in the eyes, “I just see you.”

He was caught off guard as the tall mare embraced him, almost throwing him back but keeping himself upright as she held onto him. She was sniffling, and he did his best to hold onto her and run a hand along her back slowly. He wasn’t sure what to say, or if he somehow insulted her, but he didn’t have to wait too long. They stayed there together for a few moments before Derpy lifted herself back up, wiping at her face. You could hardly tell she had cried, save for her sniffling and brushing at her cheeks.

“...thank you.” She finally said, smiling at him. “You’re…you’re really something else, Featherweight.” She continued to stay close to him, and he gave her a smile.

“What, a guy who’s had too much wine and made a pretty mare cry? Doesn’t sound too special.”

Derpy hiccuped and then giggled, before hugging him again. This time, he felt his face warm as he rested under her chin, the mare nuzzling the top of his head. “Most men talk without meaning what they say. They’re…rough, sometimes, like that. Saying what they know they can say to be nice, but only saying it because it helps them. You mean what you say. I saw it in your eyes.”

He glanced down at her grey fur and swallowed. “W-well…I did. I just hope I didn’t go too far.”

“Not at all, young man. If I heard that every day, well…I’d be mindful to not let go of you.” She replied. Her head turned as she looked at the clock, and she gave a light gasp. “Oh! It’s almost time! C’mon, c’mon, the fireworks will go off outside!”

She got up, and the smaller pegasus followed after her, not minding how she wouldn’t let go of his hand. They went to the window while the countdown was announced on the TV behind them. In front of them, unobscured by curtains or other lights outside, Luna’s starry sky shined above in wait for the impending fireworks to be launched.

“Good thing we went here instead of out where everyone else is. All those lights and bodies would’ve made it hard to see the stars and the fireworks,” he commented.

“You’re right, Feather. Just think: a whole new year in just a few seconds,.” Derpy noted.

“Kinda crazy when you think about it. But we made it a holiday for a reason, right?” He asked.

“Ok ponies, here we go! Count her down!” He could make out the newscasters’ voices as they started to count down. “10, 9, 8, 7,”

“Thank you for being with me, Derpy. You’ve made tonight better than anything I’d have expected.”

“6, 5, 4,”

When Derpy didn’t say anything at first, he thought she might’ve been waiting out the count. But when he glanced to his left at her, he saw her watching him, cheeks glowing.

“Derpy?”

“Who said the night was over?”

“3, 2, 1!”

There was a sudden explosion of noise from two solid directions. One came from the TV as the ball in Canterlot finally dropped down, signaling the end of the countdown and the start of the new year. At the same time, outside, fireworks began to rocket off into the skyline, bursting in bright flashes of white, red, pink, and green. The glow from the fireworks shone into the house, but all of it was lost as his world became centered on Derpy kissing him square on the lips, catching him entirely off guard.

He was so surprised, he nearly forgot how to respond. But his instincts finally kicked in, and he managed to press his lips back to hers before she pulled away slowly, moving only just an inch back from him to stare down at him. Now both of their faces were glowing red, and not just from the rockets exploding outside.

“D-D…Derpy? I…”

“You’re a wonderful young stallion, Featherweight. The others might make fun of you, but I see somepony special right here with me. Somepony who made my whole night go from melancholy to uplifting. Somepony who appreciates me and listens to me, and makes me feel special for the first time in a long while. In the way only a real stallion can.” Her soft tone was like honey on his ears, and he stayed frozen in place as she moved closer.

“But you know…just because the countdown’s done, doesn’t mean our night has to be over. Right?”

“R-right?” His cheeks burned as her perfume reached his nose from being so close, a smell of lilac and something else that made his dry mouth suddenly water.

“Do you think you might want that? To keep tonight going with an old mare like me?”

“Y-you’re not. Old.” He managed to get out as comprehension worked its way through his nerves to his mind and back. “B-but if you’re asking if I want to…want more with you?”

She nodded slowly. A flash of green reflected off her earrings, and he breathed in deeply.

“…I want…you.”

The admittance pushed them into another kiss, this one a little clumsy from Featherweight’s inexperienced rushing. But if Derpy minded it, she showed no trace of it, only resting a hand on his shoulder while the other found his cheek. It helped to keep them from moving awkwardly, while the stallion found himself more drawn into the kiss from the taste of her lips. It was like a mix of strawberry with the pinch of wine still resting on her lips, a blend that surprised him and made him yearn for more.

He bore no resistance as she moved him, getting him to take a seat in one of the dining table’s chairs before she followed him, moving into his lap with a surprising grace that he wouldn’t have expected. The weight of her on his lap was enticing, a feeling that along with the kissing was getting him worked up already. He did his best to steady her, hands running along the back of her dress while they continued the liplock. It felt as if Derpy was as hungry for him as he was for her, pulling back for air and licking her lips as she looked down at him. The red coloring of her lipstick, this close up, only made them look all the more inviting and tempting.

“T-this is real, right?” He murmured. “I’m not…passed out at home? I know I’ve had a lot for a first timer…”

“If you are, I’m right there with you. But I’m real. All of this,” she took one of his hands and brought it to just above her chest, letting it press into her fur gently, “is real.”

He kept his hand there for a few seconds as she kissed him again, only now, there was a new hunger to her that had him grasping for her side. It was a slow, intentional movement but the mare had her rump in his lap and was grinding against his front in a tantalizing, slow drag that was making him groan in his throat. He was already hard, his length pushing against his boxers and pants leg and throbbing with a need she inspired. She had to have felt it, from the way she was working herself against him.

“I didn’t think I could make you so eager.” She whispered when she pulled back. The dull booms of the fireworks beyond the house were still sounding off, but there could’ve been a full-scale war going on as far as Featherweight cared. His eyes watched as she rocked side to side in his lap, making him squirm as she pressed against his erection. “Do you like me that much?”

“Y-yeah. You feel…mngh.” He broke into a mumble as she suddenly muffled him by slipping his face into her cleavage. Her height advantage came well into play then, letting her move him right into place while she leaned down to whisper in his ear.

“You wanna feel ‘em? See ‘em?”

Not trusting his words, he nodded, unintentionally brushing his face further into her chest. She giggled.

“There’s a zipper at the back. Can you get it for me?”

His hands were quick to scoot up from her sides and latch onto the zipper. He calmed himself a little as he pulled it down, managing to move his head back and look at her face as he tugged the zipper down as far as needed. It went three quarters of the way down before she got him to stop, a shimmy of her shoulders making the cloth give way and slip down to reveal her bare bosom.

With nothing covering them or holding them back, Featherweight found himself savoring the sight of Derpy’s heavy mounds. The weight to them was obvious in how they drooped down, but their heft only appealed to him all the more. Capped with large, darkened areola and nipples, he couldn’t try to guess a proper comparison for size, only appreciate what he was seeing. Derpy moved for him, straightening up a little to raise their height and then bury his face truly in the midst of them.

“You just sit right in there. Momma knows what to do.” She said as she resumed grinding on him. He moaned weakly, surrounded from both sides by warm tits that even bore her fragrant scent he had picked up earlier. The way she rubbed up against him, continuing to caress him both around the head and within his pants was mind boggling. His hands couldn’t help but to try and caress her, running along her bare back with one hand while the other reached and squeezed her thigh past the end of her dress. Her skin was smooth and soft as his fingers glided along the expanse of her bare backside. The smooth stockings she had on greeted the touch of his other wandering hand, making him squeeze harder as he felt himself throb against her.

“They’re a little big, I know. But sometimes bigger is better, right?” She asked. The rhetorical was left unanswered as she brought one hand to the back of his head, the other encircling under her breasts to lift them up and surround him better. He couldn’t help a tentative lick and kiss of what was in front of him, the yearning to taste her calling from his baser instincts. It was all proving to be overwhelming for the inexperienced stallion. His hips started to jerk up in time with her movements, making more delightful friction between the pair and coaxing a moan from Derpy. A strangled cry came out of him and he tensed up, his muscles locking up before his climax started pulsing out of his cock and into his boxers and clothes.

The buxom mare picked up on this and slowed her grinding little by little until he stopped moving. When he did, she was slow to extract herself from his lap.

Rational thought came back to Featherweight along with fresh air, and he spoke up. “I-I’m sorry. You just felt so good. I-I’ve never…this is all new.” He fumbled through excuses before a hand on his thigh got him to stop.

“I know. And that’s ok.” She told him, smiling with flushed cheeks up at him as she settled between his legs. “I had a hunch you weren’t exactly going around town. I’m glad.”

“Y-you are? Why?”

Her smile made his whole body warm as she eyed his groin where his cock was still hard. “...I wanna take it myself.”

With that declaration, Featherweight offered zero resistance as she helped undo his belt buckle and fly, his pants easily sliding down to his ankles and the floor. His boxers bore a dark stain at the right leg and his groin, making him almost embarrassed before his whole face flushed red as Derpy leaned in and pressed her nose to his bulge, inhaling deeply. Her shudder made him twitch against her, and she gave him a kiss through the cloth before helping to tug them down as well.

He had tried to get an idea of how he compared to the average stallion before this moment - really, what colt doesn’t check at least once? - but knew he wasn’t the biggest. He did have an idea that he wasn’t lacking, at least; his pinkish-red colored length laid against his bare thigh for a moment before Derpy’s head moved in closer. Her tongue’s sudden contact against the sensitive head made his legs twitch, and she giggled at the reaction before continuing to lick and clean his cock of the essence that stained it still.

“I-is this…ok? For you?” He attempted to ask, albeit between groans of appreciation for her tongue’s dexterity. She stopped for a moment, his cock clean of all but her saliva for now as she stroked him with one hand.

“It’s wonderful. I don’t like them huge. I like them at a good size, like this. Wanna know why?” Her playful whisper made him nod slowly as she lifted his cock up, pointing it at her waiting lips.

“Because they don’t mess with my gag reflex when I do this.”

He watched with wide eyes as the blonde mare opened her lips wide enough to slip into her maw, his tip greeted with the tingling sensation of wetness and warmth surrounding it before she slid more of him inside. Down and down her red, soft lips went, caressing every inch of his cock as she slipped more of him into her mouth and even into her throat before resting at his base. Her nose slowly shifted about as she turned her head this way and that, nuzzling into his groin and giving off an appreciative moan as he throbbed in her oral grasp.

Featherweight couldn’t help but to throw his head back, closing his eyes and enjoying the way she so easily worked his cock over, pulling back and sucking hard before diving back down. It was a slow, almost loving bobbing motion she made, and every tender pass had him quickly returning to being rock hard again. It didn’t deter Derpy in the slightest, only seeming to entice her more as she basked in the taste of him. One of his hands came up and ran along the top of her head, brushing through her blonde hair and moving it aside when it threatened to get in the way of her mouth. She rewarded him with a harder suck as she pulled back all the way to the tip, coming off with a pop and making him moan in earnest.

“Derpy, you’re…you’re amazing.” He breathed out, his cock throbbing as it pointed at her, still wet with her spit. She eyed his tip first before looking up at him, taking hold of his base before squeezing him gently. “S-shouldn’t I…do something?”

“You can. Soon. But I like getting to be in control like this. I…haven’t in a long time,” she told him as she kissed his tip, making it throb again. “You’re making me so wet, Feather. Your cock smells so good. He tastes like a treat.”

“...n-not stopping you,” he mumbled.

“I know, silly,” She giggled before shifting closer, “but I needed him back up so I could do something really nice for you.”

He wasn’t sure what she meant at first until the mare brought her chest up and pooled it onto his lap and over his cock. With a little effort on her part, he slipped right into her valley with little effort, completely engulfing his member between her large breasts and encasing him in a warm sensation he’d never imagined before. He gripped the chair’s armrests tight as Derpy wiggled and shifted her bosom around, stimulating him further.

“Do you like it?”

“H-holy Celestia, yes! It’s…y-you’re incredible!”

“I’m glad. Some stallions get put off from how big I am. I’m not for everyone.” Her wandering eye seemed to look to the floor while her normal eye centered on her cleavage where his cock was buried. “But if you like it…I’m glad. I want to keep making you feel good.”

She started to work her tits up and down in a rubbing motion, the sheer mass of her breasts keeping him trapped between them. He let her set the pace, taking in the sight of how her tits enveloped his lap with ease as well as his cock. Even when she was on a downward stroke, he could only just barely see his tip peeking out before it was swallowed up again. Feeling her soft breasts work around him was heavenly, and had him hungry for more and more of the MILF before him.

“Derpy…you feel so…so good!” He exclaimed.

The blonde mare only smiled and worked harder on him, bouncing her tits around his cock as she worked to milk him. The earlier climax was giving him a little staying power, but only so much. He couldn’t help but to react, reaching out to also squeeze her tits around his cock as his hips started to thrust up into her cleavage. It didn’t deter Derpy in the slightest, only making her giggle playfully at his yearning for her.

“That’s it honey. Gimme all you gotta give. Use momma’s tits all you want to.” She encouraged. He realized that calling herself a mother was for both their benefits, that maybe she knew all too well she was labeled as a MILF by the more crude stallions. If so, it didn’t take anything away from her. Featherweight only thrust harder, giving in to his lusts and trying to rut her tits like it was all he had.

The way they bounced and shook from his efforts just made his lust rage all the more. His hands would slip, and she’d be there to keep the squeeze tight around his cock before he had his hands overtop hers again. He panted for air, the room feeling hot and musky from their efforts so far. The wanting expression on Derpy’s face was a tipping point for him, seeing her almost begging for him to finish. He could only manage a few more hard thrusts before he tensed up, pushing his cock up as far as he could.

Without clothes to get in the way, his seed was allowed to fire off freely. The first thick salvo of cum arced up and out of her cleavage, splashing her cheek and chin to earn a squeal of delight from the buxom blonde. Another two spurts made it out, staining her neck and the top slope of her chest. From there, the rest squirted out into her cleavage, the sticky streams filling her valley and leaving her to toy with him by keeping him squished around from all sides before finally letting him withdraw out the bottom end.

“Ooh…so warm…” Derpy said as she brought a hand up to collect the seed that had splashed her face. A dip of his sperm into her mouth made her hum, before pulling out the finger, clean as anything. “And delicious!”

Featherweight spared himself any commentary right then, focusing on falling back into his chair and panting for breath. He could feel himself sweating from exertion, yet the tingles of sexual excitement still coursed through him. It was enough to get him to open his eyes and watch as Derpy stayed put while kneeling in front of him, running a hand along the inner slope of her breasts to scoop up more of his seed. The sight of her drinking his essence with clear enjoyment prompted him to sit up, getting her attention on him as he spoke up finally.

“You’ve gotta be the most amazing mare I know, Derpy.” He declared, making her beam at him. If not for her topless, sex-ruffled state, the look would be entirely innocent on her face. “I…what can I do for you, though?”

“For me?”

“Yeah. I might be a…virgin. For the moment. But I can’t just make you do everything.”

Derpy grinned at him. “For the moment, huh?” He blushed but she didn’t turn the idea down. Instead, she stood up and let her dress slip down her figure, the black material pooling on the floor at her feet like his pants had. It left her in a matching black pair of lace panties, a sight he appreciated particularly as they were clinging to the outline of her marehood tightly. Featherweight watched with rapt attention as she ran a finger along the front of her panties, a small shiver running through her before she looked down to him, waiting.

“Come over here and help me with this, hun.”

Instinct suggested he adopt a kneeling position like she’d done, something that put his head right at her crotch height. The smell of her perfume was enriched by another scent coming off her, one he found growing stronger as she slowly moved her panties down to expose herself. His jaw dropped at the alluring sight of her folds, the darker grey lips looking plump and inviting to touch. A tiny tuft of blonde hair, echoing her mane, sat just above it. He leaned in to move closer, but Derpy moved first, positioning herself up against the table before he could get ahold of her.

“Have you ever heard of a stallion going down on a mare, Feather?”

He shook his head slowly. “It doesn’t sound like a bad idea though. All things considered.”

Derpy smiled and nodded, using two of her fingers to rub along her front again. He watched as a little moisture - her own arousal, he realized - pooled over her fingers as she teased herself. “A good stallion treats his partner equally. I’ll let you try it out for yourself though. There’s not really a wrong way of doing it. Except, you know, not doing it at all.”

Feather managed a snort before moving closer to her. He took a moment to think about just what he should do, and looked up at Derpy’s eyes. The mare’s one-eyed stare held his gaze, and it helped him decide what to do first. It led Featherweight to lift up just a little, and to first kiss the spot just below her tuft of blonde above her marehood. The action made Derpy coo lightly, a hand coming down to run through Featherweight’s hair as he peppered all around her with loving kisses.

“W-what’re you doing?” she asked when he stopped.

“Showing my appreciation,” He replied, “to a beauty like no one I’ve had on camera.”

His words made more color rise in Derpy’s cheeks before he moved down and faced her marehood properly. Knowing she was waiting, he chose to take the deep plunge and burrowed his muzzle up against her marehood, his tongue pushing out and probing into her depths. Derpy’s gasp above him felt muffled in his awareness as new tastes and textures caressed his tongue. She was warm, the wetness of her pussy greeting his tongue straight away. The flavor of her was an interesting mix, a little bitter and yet a delight to encounter. Encouraged by this, Featherweight brought his hands up to her hips, giving a light squeeze as he pushed his tongue further into her.

“F-feather! That’s…that’s good, honey, keep going!” She breathed out. The hand at the back of his head pushed harder, more firm in its grip on him as he worked his tongue out as far as he could reach before needing to pull back. Every bit his tongue touched was wet, a sensation he could compareto nothing else. But knowing it was for Derpy, pleasuring her, drove him on to do more. His hands continued to gently knead and rub her hips and then her thighs as he worked his tongue back and forth in slow strokes she enjoyed.

The table she was resting on creaked a little as she leaned against it more, her hand that had been bracing her joining its partner in stroking and pushing on Feather’s head. The pegasus tried to think out what else he could do to please her, and it came to him as he moved one of his hands to join near his face. With a light push, he was able to spread her wider apart and soon dipped his finger in to partner his tongue in pleasuring her. It was the right move, he discovered, as Derpy’s whole body shook from his efforts.

The surprise came when he found himself needing a little air, withdrawing himself a little but keeping his fingers working in and out. The brush of his tongue against the roof of her marehood hit something that felt softer, and different. Derpy gasped, and he looked up at her from her groin to see one eye closed, the other watching him in sheer lust. “D-do it again!”

“Do what again?”

“Your tongue, sweetie. Your…oh, heavens, it hit just right then.” She breathed out.

He nodded, and dove back in again with a fresh breath of air in him. His fingers continued to work at her wanting marehood while he let his tongue explore again. It took a few moments, but exploring the top part of her tunnel again yielded good results when her hips bucked up into his face. “Yes! Yes please, right there! Oh please!” Her beckoning had him circle the spot he’d just passed, and soon, he had her shaking and gripping his head almost too tight. But knowing it was his efforts making her almost scream made him endure it.

“Feather! Oh, please, Feather, more!” She cried, chest heaving as she gasped for air. Adding a second finger to join the first, he worked out a rhythm between pumping his fingers in and out while also working her sensitive spots with his tongue. Derpy’s words fell into a cacophony of syllables and moans, all the while her juices flowed into Feather’s mouth and even down his chin. When she started to gasp in rapid breaths, Featherweight took the chance to finally toy with her clit, the erect bud getting his thumb on it and toying with it in a tender fashion.

“FEATHER!” She exclaimed between high pitched gasps as her juices splashed onto his tongue and mouth, catching the young stallion off guard. He couldn’t pull away due to her grip on him, but he could envision her pleasure-stricken expression as her orgasm rocked its way through her body. By the time her grip eased up on his head, he was a little light-headed but recovered once he pulled back. Wiping at his chin, he just smiled up at the flushed face of the buxom mare.

“So…did I do good?” He asked. “Or should I go again to make sure I got it right?”

Derpy took a moment to answer, still getting light gasps of air in her lungs. Surprising Featherweight though, she moved - if on wobbling legs - towards him and brought him up to kiss him deeply. He had a brief moment to wonder if she minded the taste of herself, but from the way her tongue snaked its way around his, it wasn’t an issue. Before he could realize it, she had him in a chair again, claiming his lap for herself and keeping his now rock-hard member squeezed between their bodies.

“Feather?” She whispered when the kiss ended, her lips hovering in front of his as she stared down at him again.

“Yeah?”

“Before…I just wanted to say. You’ve done so much to make tonight wonderful. But this is your first time. If you don’t want it with me…”

He fixed his grip on her body, one hand finding purchase on her hip while the other took hold of a healthy heft of butt cheek. “I think you can tell my answer there, Derpy.”

There was a light glisten of water in her eyes, before Derpy kissed him again. He welcomed it, letting her take the lead as she shifted about in his lap. With a little stretching and some help from her wings, the busty blonde rose up and aligned his cock with her entrance. In a surprising feat, she never stopped the kiss, making him moan into her lips when she took him into her and sunk down. She didn’t stop until he was fully buried within her, leaving her to wrap her arms around his shoulders and sticking his head in her cleavage. The sweat and smell of sex emanated from them both, yet it only enticed the young stallion for more of her. He yearned for every bit of her he could touch and hold and feel.

With a silent signal, the mare rose up and started to pull him out from her tight marehood, only to stop halfway and rock back down in an easy riding motion. The rhythm was established after a few passes, letting Derpy control their speed while he lavished her body with what attention he could give it. His lips and tongue worshiped every inch of her tits he could attach to, eventually finding his way to a bouncing nipple before latching onto it and suckling hard. Derpy’s cry of delight had him tease at it more, using his tongue and teeth in equal shares to stimulate her better.

“Feather, oh stars, it’s so good. So hot inside.” Derpy said as she continued to ride his cock. The slap of her ass cheeks bouncing off his lap was as equally arousing as the wet sounds she made around his cock with her marehood. Her hand found its way to the back of his head, pushing him harder into her breast. “Suck mommy’s tit, baby! It’s so good!”

The chair bounced and creaked in time with her riding him, and Feather’s lust started to catch up with her as well. He started trying to thrust up on her downward bounce, pushing himself deeper into her and being rewarded with a moan of want from the busty blonde. Swapping breasts, he used his other free hand not holding onto her tit to keep her steady on top of him. The added help of pulling her down on his cock was a bonus as well. Every thrust was a slice of warm, wet heaven for the cherry popped stallion.

“Yes! Yes, Feather! Gimme all of it! I want your cum!” She beckoned, moaning loud enough that Feather almost worried for his neighbors. But he chose not to care, enjoying everything Derpy had to offer way too much to mind. Let her be noisy, his lust decided; they both deserved to indulge.

He could only hold out so long, however; he was still inexperienced in sexual stamina, and knew it was coming as he throbbed in her depths. But his efforts to try and last were in vain when Derpy kissed him again. He wanted to surrender everything to the mailmare, and with a final thrust, he did.

Featherweight’s load had nowhere to splash but within Derpy’s marehood, every inch of her seemingly clamping down to milk his cock as it burst with his seed inside of her womb. Derpy seemed to realize it only just barely, instinctively hilting his cock into her depths and clinging right to him as he rode out his climax. Head buried in her cleavage and feeling her embrace him, he gladly let go and allowed himself to bask in the glow of ecstasy while filling her with his essence.

Even after his climax had dwindled down to a dribble of fluid, they never parted. Derpy only stayed with him, refusing to let go. With a labor of effort and will, Feather removed his sweat-glazed head from her vast cleavage to look up at her properly. She looked as winded as he felt, but utterly content.

“Derpy?”

“Yeah, Feather?” she whispered.

“That was…amazing. Thank you.”

She smiled at him. “No. Thank you, Feather, for-“

Whatever was meant to be said was momentarily lost, as the outside world erupted with a momentous and huge rocket burst that filled the room with red and white color. At the same instance, the chair they had made love in could finally take no more, the wooden legs crashing apart and bringing them both to the floor. Feather laid under Derpy’s body, staying still to not accidentally hurt her.

“Oops!” Derpy let out, making Feather laugh as she leaned up to fret over him since he caught her. He could only embrace her, and Derpy returned the hold as they sat there together.

“You really are something, Derpy. Happy New Years.”

“Happy New Years, Feather.”

Author's Note

Happy New Years, everyone! See you in 2022!

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