The Single Milf
Anon was in an... odd position at first. The last thing he remembered, he was on his way back to his apartment from his deadbeat job, and now the next thing he knew, he was in a strange world full of bipedal horse people... or ponies as they referred to themselves. He wasn't sure what to expect, but he definitely wasn't expecting to be welcomed into their society so quickly. The world he was in wasn't quick to judge him or assume things, even if he was alien from another world.
That could be thanks to the Princess of Friendship: Twilight Sparkle and the School of Friendship which was meant to be welcoming to creatures of all species alike. Something like that anyway. Though to say that the people... er, ponies were welcoming would be an understatement. He made a nice Home in Ponyville and had settled in pretty quickly, making friends with the locals quickly.
Anon decided to spend some time hanging around with Button Mash and his family... that is him and his mom: Cream Heart, as they were really the only two members of the family. Button seemed to have grown used to having him around. Without whoever his father was, he saw the human as a sort of father figure. He assumed that Button just saw him as an older brother because that was what he'd expect from somepony his age.
Cream didn't mind having Anon around, especially because of how helpful he was not just with taking care of her son, but also with helping around their home in spite of her insisting for him not to. Hey, Anon was a nice guy, and he liked hanging with the kid from time to time.
The human and the young colt were in the living room, currently playing one of his fighting games. He was in his gray pajama shorts and his large pajama shirt.
Anon went easy on Button so that he wouldn't lose... at first... but then once he started playing like a pro player, the human stopped going easy on him. However, even though the colt was twelve years younger than him, even though he was trying his hardest, Button was straight up kicking his ass without even trying.
"YAY!" The colt cheered as Anon’s character got K.O.'d the second time.
"You win!" The tv announced.
"Dang kid, you're pretty good." Anon says to him.
"Eh, I'm just doing my best." He says all innocently as the screen showed that he won thirteen matches and the human... lost thirteen matches... and had the same amount of wins as he had losses.
"Having fun you two?" Cream says while entering the room, wearing a purple shirt along with a black knee-length skirt.
"Yeah! Everything is awesome with Anon over." Button says happily as the teen rubbed the back of his head.
"That's good to hear." She picked up her purse before making her way over to them. "I'm gonna be home late tonight, so just remember to get ready and be in bed by the time I'm back. Okay?"
"Yes, ma'am/mom." Anon and the smaller pony say.
"Good." She then bent down to her little foal which caused her skirt-covered ass to almost be in Anon's face which he quickly turned away from. "Bye sweetie, love you." She says while kissing her son on the head.
"Bye mom, love you too." He says as she leaves. "So, wanna play again!?" He then said, beaming with glee.
"How about we play a different game, Mash?" The human says, sweating.
"Okay." He says before he picked up a case. "How about this?" He asked showing a game that had a co-op mode where the players work together.
"Yeah, that looks like fun." Anon says as he happily went over and put the game in. "Ready, little dude?"
"Yeah! I'm ready! We're gonna stay up all ni-!"
(Several hours later)
In spite of his claim, after a few hours of playing, Button was out like a light. And just in time for bed as the princesses: Celestia and Luna had already lowered the sun and rose the moon sometime back. Anon sighed before getting up, turning the tv off, and picking up the unconscious foal, taking him to his room. The colt was much smaller, but that didn't mean that he wasn't heavy.
After getting him into pajamas, putting him in bed, and tucking him in for the night, Anon left the room, keeping an eye on him while closing the door to make sure he wasn't faking it. He kept it open a crack for a second before fully closing it.
With a sigh, he turned to go to the couch, only to bump into something that made him step back a bit before looking at what he collided with. Boobs covered by a purple shirt. Looking up, Anon saw Cream Heart looking surprised and his face burned red because he literally just bumped, face-first into her bust.
She muttered something under her breath that he couldn’t hear. "Thank you for putting Button to bed, (Y/N)." She says, brushing off what just happened.
"Uh, n-no problem. It wasn't trouble." The human says before wondering just how she got in without him even noticing.
"Usually, he stays up much later than this. One time he's stayed up for an entire night."
"Sounds... tough." He didn't know, how his being there really changed anything, but... it did somehow.
"It's been really hard to take care of him alone. He spends so much time playing games that it's impossible to get him off of them." She says before looking towards the console. "You didn't play for too long, did you?"
"Not really no." That was merely a half lie. Anon did stop in order to have bathroom breaks, dinner, and stuff, but for the most part, all he did was play games.
"Oh good." She sighed.
"Alright, well I should get to sleep." Anon says as he starts to go back to the couch.
"Actually-" Cream then grabbed his arm. "I don't think it's right for someone such as yourself to sleep on the couch." She says.
"Uh, Ms. Heart, it's fine. It's actually-" Before he could tell her that the couch was comfy, she cut he off.
"Sweetie, there's a room you can stay in, instead of the couch." She insisted before tugging him along. "Trust me, you deserve it."
'Deserve it?' He thought to himself but dropped it as he figured it wasn't worth arguing with her.
Perhaps she was leading him to a guest bedroom or something, at least that's what he expected. Though he was surprised to find that she actually led him into her own room. This confused him for a moment.
"Uh, ma'am, this is..." Anon began to say before she stopped him with a hand on his shoulder.
"As I've said, it's been hard trying to raise him on my own and for all you've done to help, I don't believe the money would be enough of a reward for all your efforts." She says which he still didn't understand, but then she cupped his cheeks and moved her face closer to his, which made him blush harder. "So, how about I make it worth your while?"
"Uh, M-Ms. Heart, I-" Before he could say anything further, he found his lips were soon captured by her own.
Anon froze, eyes widening at the moment. He was shocked to say the least, though he slowly started to melt into the kiss, not thinking of what he was doing. Just as his hands were about to move up and cup her face, she pulled away and stared at him.
"Please, just call me Cream, dear. ~" She then says in a sultry tone.
... Oh, fuck it. Not like he’d get a chance like this again, right?
"When do you wanna start?" That smirk on her face was enough.
So, Cream stood back up, walked over to the bed, turned around, then pulled her shirt off, revealing her huge J-cup breasts with her pink nipples poking out of her fur. Immediately his pants felt tight as all hell. Sure there were mares that had breasts that not even humans can compare to but she had a bust bigger than any other he had seen.
She laid on the bed, then motioned with her finger, beckoning the man to come over. Anon didn't hesitate, making his way over and getting onto the bed before reaching out and taking ahold of the large jugs and feeling them. They were soft and very squishy, and his fingers practically disappeared into her fur and flesh.
Damn did they feel good. The pony milf put a hand on the back of his head and moved his face down to one of her nipples. He took it inside his mouth, sucking in an instant as she gasped a bit, but let out a slight giggle before caressing his head. She also reached down to rub his back through his shirt.
He looked up and saw her staring back down seductively. Saying he wasn't turned on by this pony milf would be an absolute lie. Then he felt some liquid begin to enter his mouth. It tasted creamy with a hint of sweetness.
It didn't take a genius to know that it was milk, especially since it squirted out of her other breast down the back of his other hand. However, it took him by surprise to know that she was still capable of producing milk past her pregnancy, but he wasn't complaining. He pressed his head further into her boob until your face disappeared.
"You're a feisty one aren't you? ~" She says, hand still on head.
Cream’s soft skin and fur against Anon’s face felt like heaven and her milk sure as hell tasted like it. Not to mention, she had a motherly touch that was unrivaled by anything he’s experienced before. Anon wanted to stay like that and keep having that nice drink, but unfortunately, he needed to breathe, and his face was getting hot, so he pulled away and panted for air.
"Goodness, did you enjoy it that much?" She asked with a hand on her cheek.
"Sorry, I just don’t know the next time I’d be able to do something like this. Honestly, it tasted nice." You tell her as she giggles.
"Is that right? Well, before we continue, could you also remove your clothes? It would be embarrassing to be the only one naked."
Anon looked down, seeing the bulge that was begging come out. He started by removing his shirt, then pulled down his pants, boxers, and socks as his member sprung free. Cream Heart was in awe at the sight then her smile returned before she reached down and began to feel his member which only caused it to harden.
"So, this is what a human cock looks like." Cream says before rubbing the tip. "A big one at that."
She then continued to rub the base and he got the feeling of her soft hand against his member which only hardened it further. Still, the human had tried to keep it together despite feeling relief shoot through his body. She stopped and stood up before taking off her skirt and letting it drop onto the floor.
Anon then got a full view of the mare’s body. She had a nice hourglass figure and a dripping entrance that would’ve made a stallion or a man in Anon’s case, have a massive nosebleed. Either she managed to regain her shape years after giving birth to her foal, or she somehow kept it despite post-pregnancy. Whatever the reason, the young man couldn’t say for sure.
“See something you like? ~” Cream says in a suggestive tone.
“Y-yeah.” He mustered out.
She giggled before straddling him, aligning his member up just with her lower soaking lips. The teen was hoping for a little more foreplay, maybe having her use her breasts to pleasure his member, however then again, Button surely would hear and the last thing you’d need is him being traumatized and learning things too early.
“You know, Button’s always wanted a little sibling.” Cream says as Anon’s eyes met hers in surprise.
“Woah, woah, I thought this was just a reward or something.” He says as he leaned back a bit.
“Of course it is, but to be honest, after seeing how fond he’s become of you, I may have started to become a bit attracted to you myself.” She says before brushing a hand down his chest.
“I-I mean I guess, but I’m only eighteen. And plus, I don’t know if we can crossbreed.”
“Well, it’s worth a shot surely. Also…” She then leaned down, pushing her bust against him as his face turned even redder. “You don’t seem to mind getting it on with this old mare. ~”
Damn, that tone was really getting to him. Anon thought, screw it. He was thinking of having kids sometime later in life, and he was technically an adult, at least by his world’s standards, so what’s the big deal if he does have any early? Well, if he could with this mare anyway.
“Alright, you convinced me.” He says while grabbing her hips, then lifting her over his member.
She leaned down, nuzzling her snout against his nose while her tail started to swish left and right. He reached up and gripped her ass just where her cutie marks were, giving them a nice squeeze before pulling her down onto him, pushing his member right into her snatch.
She yelped a bit while he grunted. She was tight, with not a hint of looseness.
“Oh, great Celestia.” She moaned out, clutching the man’s shoulder tightly.
‘Shit, I wasn’t prepared for this.’ He thought to himself.
Anon was about to ask Cream if she was okay but then felt her shifting in his lap before wiggling her hips a bit as if making sure it was snug inside. Well, it did allow his member further entrance until his tip pressed against her womb entrance.
“Alright, I’m ready now.” She says as she stops.
Anon took a moment to adjust before taking hold of her hips and reeling his own back before repeatedly and slowly thrusting back up into her. She let out soft moans that were thankfully quiet enough so that her son wouldn’t hear, but enough for the man to hear. A part of him was still a little worried that maybe Button could wake up in the middle of the night for another reason, though brushed off the idea and hope that it wouldn’t happen.
Honestly, the thought was starting to get him a little more excited and encourage him to keep going. Cream didn’t seem to mind and even got a little excited herself. She nuzzled her nose against his before lifting her chest and putting her untouched nipple in his face.
“There’s still some left. ~” She says.
The man didn’t wait for a second and latched his lips onto her nipple and began drinking more of the milk. He grabbed the boob that he had thought to have already drunk dry before and began fondling it in his grasp. Her moans did become louder but still weren’t loud enough to alert the attention of her foal in the other room.
Anon was becoming harder and pressing more against her cervix. He got a little careless and started thrusting faster and faster which made her gasp between moans. She grabbed his shoulders and flipped, pulling him on top of her, causing him to detach from her breast and stop thrusting.
He took a second to catch his breath before looking into her eyes, and she returned eye contact with a hint of seduction. He looked towards the door as if making sure her foal wasn’t awoken by any means before sighing and started thrusting again at the same speed.
Cream pulled his head down against her collar bone, hugging him tightly as her breasts hit his cheek with each passing second. She gave him a kiss on the top of his head before locking her legs around his waist whilst he kept rhythm with his hips. Although, he was starting to feel something coming up.
“H-hey I… I’m getting close.” Anon says.
“Don’t stop. Let it all out into me.” She says through her moaning.
Well, she said it. He then started thrusting even faster in her which caused her to moan louder. His hips moving like a piston seemed to have triggered something as he suddenly felt her pussy tighten around his member. He grunted a bit, but didn’t stop.
Then he realized something and looked up, now listening. Her moaning was surely loud enough to alert Button now and and with the creaking of the bedframe, he couldn’t let that happen, especially now. Thinking quickly, he slowed his thrusting for a moment before leaning up and capturing her lips in a kiss before he went faster again, her moaning now silenced with his mouth.
He further attempted to quiet her by dominating her tongue with his own, arousing both of them even further. After a while, her entrance soon had a vice grip on his member before she screamed into his mouth while her eyes rolled up and she sprayed his member with her juices.
Right as she did, he blasted his load right into her womb. Her legs and arms hugged him tighter than before. Neither could see it, but her belly was slowly expanding before stopping. The grip the mare had loosening as a trickle of cum made its way out from her lowerlips. His member softened and slipped out of her, leaving a trail of his load to follow.
Then they separated and gasped for air, looking right into each other’s eyes.
After catching their breaths, Cream smiled then pulled Anon in for another hug and turning to lay on their sides.
“I haven’t felt that good since my younger years.” She says while cheerfully snuggling against her human. “Oh, it makes me so excited to have another foal.”
The human grunted a bit as she was hugging a little tight, but he sighed and hugged back. He snuggled into her ‘pillows’, falling into a deep slumber.
Honestly, this was an amazing few months in Equestria for him. He had made some friends, gotten himself a place to stay, and now got to lose his V-card to a lovely and sexy mare. If he wasn’t leaving anytime soon, and if this was gonna be his new life, he was happy to live it. He didn’t know what good he did to get this lucky, but he sure as hell was grateful to whatever god brought him here to this world.