Part 1
Anon was in a dry spell. His wildest dreams had come true and it still felt incomplete. He didn't remember how he got to Equestria, but he'd been there a few years so he'd ruled out dreaming.
In that time he'd become a part of the ponyville community. They loved him around town, but certainly not as a potential love interest. That dry spell would attest to that. In all three years he hadn't gotten laid once, and he was not "above" nailing a pony. With how long he'd been here as the only human he'd practically become a "ponysexual."
He wasn't ugly, he wasn't incredibly handsome, but he wasn't ugly either. It also wasn't from lack of trying. He'd lobbed a few softball pickup attempts at ponies he thought might go for it, but no luck. The majority of them just didn't seem to see him as a potential lover.
He was staying in the guest room at Sweet Apple Acres, helping out around the farm for food, board, and some spending money.
"Anon?" Called Applejack, "ain't yuh finished with them weeds yet? Get the lead out, yuh gotta watch the castle for Twilight!"
He begrudgingly plucked the last few weeds he needed to pick as the sun beat down on his back. She worked him hard, and she wasn't always nice about it. He figured she was holding him to the physical standards of hard working horses and didn't care that he was an out of shape monkey boy.
He didn't want to argue with her, he didn't know where he'd go if he couldn't stay here so he dumped the wheelbarrow and grabbed his sack from his room. He headed out without a word.
She shouted after him, "hey did y'all dump the wheelbarrow where-"
"Yes!" He snapped over his shoulder. "Goodbye Applejack!"
He was in a terrible mood. The bright and beautiful day did nothing to help. At the very least he'd be staying in the castle for a few days and he wouldn't have to deal with her chores. He was fed up with the way things were going. He was in his dream world but he wasn't living the dream.
"Liquor, " he thought to himself. "I need a goddamn drink." The ponies actually enjoyed the occasional drink believe it or not. They didn't have a lot of hard liquor aside from what the occasional moonshiner distilled, what was widely available was wine and it was better than nothing. He made a stop at the town market and picked up a few bottles and a corkscrew. He opened a bottle and had a bit during the rest of his walk. He wouldn't have much else to do this weekend.
He scaled up the steps and into the castle. His steps reverberated off the vaulted walls and mixed with the sound of several voices talking. He followed them into the map room.
"So Spike will be back on Monday, " said Twilight. "All you have to do is water the plants and make sure no fillies wander in and get lost."
"I can handle it dear." Velvet replied.
"I know mom, are you sure you don't want to come with us?"
"Oh, no dear, you and your father have fun."
They finally noticed Anon in the doorway. "Oh! Anon! I totally forgot I'd asked you for help, uh," Twilight fumbled with her words. "My mom actually decided to stay here so... you can go home if you want?"
"Twilight, " he sighed. "I really don't want to go back to Sweet Apple Acres. Applejack's been getting on my nerves lately."
"Oh no, what's going on?" She asked worriedly.
"Well," he sighed "I guess I'm just tired. I get that they're all hard workers, but she could cut me some slack once in awhile."
He looked at Velvet. "I don't suppose you'd be ok with some company? Maybe just for one night? I might be feeling better by then."
"Oh I don't mind at all!" She replied sweetly. "We haven't really had a chance to get to know each other well, have we?"
His heart skipped a beat. He'd only met her a couple of times and they never had a real conversation. Now that he got a good look at her Twilight's mom was actually kind of hot. She definitely looked great for her age.
"You can come camping with us if you want." Offered Night Light. "Velvet likes her space to be honest."
He saw her glare at him. Was something going on between them? "Uh, I think I'm good sir thanks for the offer though." Anon played it off.
"Well, alright, your loss." Twilight chirped cheerfully. "Come on dad, let's get going."
"Lead the way dear." He replied cheerily. They grabbed their bags with their magic and headed for the door.
"Well, " Velvet said once they were gone. "Shall we see what's in the fridge? I'm actually a pretty good cook!"
"Yea that would be great." Anon replied. "No hay thought, can't digest it."
She made a fantastic dinner, he offered to help but she wouldn't let him. They talked about what Twilight and Shining Armor were like as kids, and he told her stories about growing up in the human world. She was fascinated, but she didn't pry too deep into his past.
After they were done he insisted on helping her clean up. They cleaned the dishes together, then retired to the living room. It didn't have big vaulted ceilings, so it felt cozier. There were a few bookshelves in the room and several couches.
Velvet grabbed a book and chose a couch. Anon didn't feel like reading, he chose the couch next to hers and set his bag down at the foot of it.
"So, how are your studies? Is Twilight a good teacher?" Velvet asked as she flipped through pages. "She's as stubborn as her father, if she ever gets too pushy just tell her you'll tell her mama on her." She giggled.
"I'd like to see the look on her face." He chuckled. Since he'd arrived in Equestria he'd been taking friendship lessons from Twilight. He wasn't "required" to, but there was surprisingly little to do without technology and Twilight was pretty cute.
He glanced over at Velvet laying on the couch. His glance became a stare, he was enthralled by her curves. How old was she anyways?
"Would you grab me the next volume of this dear?" She asked, passing him the book she'd been reading.
"Yea, sure Twiligh-" he stopped short.
"What's wrong?" She asked.
"I already know a Twilight." He replied. "Would it be alright if I called you Velvet?"
"Uhm, " she briefly considered it. "I usually only let Night Light call me Velvet..."
"Well, " Anon replied "I could just call you ma'am or Mrs. Twilight, but I'd feel a lot closer to you if I could just call you Velvet."
She looked a little worried as she applied some serious consideration to it. Eventually she put on a comforting smile, "you know what? I'm alright with you calling me Velvet, Anon, I hope we can be great friends."
There was another hard thump in his chest. "God she's cute, " he thought.
He put the book back and took out the next book in the series. He handed it to her and sat back down.
"So what was up with your husband earlier?" He tried to ask casually.
"Oh." It seemed to have made her a little uncomfortable. "Well, once Twilight left home things between Night Light and I got a bit... stagnant."
"Stagnant?"
"It's nothing really." She dodged. "It's old mare problems dear, nothing you'd be interested in."
"I am interested ma'am." He stood up, walked over to her couch and sat next to her. "You think he's not attracted to you anymore?"
"Well-" she stammered. "Not exactly it's just... slowed down quite a bit, but it's nothing you need to worry about Anon. You're a good boy for worrying about me though." She gave him another sweet smile.
"What did he mean by you like your space?"
"Uhm, " she started awkwardly. "Whenever I... oh how do I put this? Whenever I... want things from him he's usually dismissive, and when I kept getting upset he decided I was just "moody" and it would be best to just give me space."
"You mean when you want sex right?" He scooted closer to her. "That's what you meant by stagnant... he doesn't want to have sex anymore?"
"This-" she scooted away. "Isn't something you and I should be talking about."
"Shot down again... " he thought. He slumped back on the couch and rubbed his eyes. Why was he doing this, he wondered. Was this really who he wanted to be? The scumbag who hits on someone's married mom? Was he just desperate for any kind of connection?
She climbed off of the couch and put her book back. She glanced worriedly over her shoulder at him, he just sat there letting the self loathing wash over him.
After a moment she came back over, "Anon I wasn't trying to hurt your feelings." She said humbly, "please don't take it personally. It's really a personal problem it's not you..."
"You know... I've been pretty lonely for a long time." He admitted defeatedly. He wasn't sure why he was suddenly opening up to her. "It's hard being the only human here. I'm a young man, I want love... I have needs..."
She listened with quiet concern as he continued, "none of the ponies see me as a potential lover. I guess I can't really blame them, I'm not even the same species... am I doomed to be alone forever?"
"No!" She implored, and climbed back onto the couch next to him, "you're a fine young man Anon, you'll find somepony!" She put a hoof on his shoulder. She got a listless look in her eye, "if I were to be honest... I'm quite lonely myself."
"What?" He asked, "why?"
She rubbed her arm and hung her head painfully as she reminisced, "things used to be so good when we were starting our family... when Shining was a little colt we couldn't wait to have another... what happened?"
"Nothing," he replied dryly. "Sometimes... as time goes on... guys just lose the attraction they once had for somebody. You didn't do anything wrong, it's just life, and sometimes it's unfair."
He heard a sniff beside him, and looked over to see her head down and trembling. Tears dripped down her snout onto the couch cushions. "You're right, " she croaked "I knew it, but I didn't want to believe it... He's tired of me isn't he?"
He reached out and placed a hand on her head. He gave her a few pets, then to his surprised she slumped forward over his lap.
He lethargically stoked her mane for a while as she cried herself out. "I was trying to feel sorry for myself you know?" He sighed sarcastically.
"I'm sorry, " she blubbered as she sat back up and strenuously dried her eyes. "I'm unloading all my baggage on you aren't I? I've just been burying my frustrations for so long, as soon as I start opening up it just comes pouring out..."
He stood up without a word and walked over to his bag. He knelt down and rumaged through it. He pulled out a bottle of wine, set it on the table in front of them, then sat back down.
"We both need this..." He said, seemingly to himself. After a moment he turned towards her with a determined look. "I've got three bottles of wine. We don't need to give them an excuse for why we drank them, but they can be a perfect excuse for why we forgot if we need it."
"I don't really get what you mean," but it seemed like she did get it. It seemed like she was trying to act like she didn't get it.
"Maybe we drink this wine, " he started and glanced at the bottles, then back to her. "Maybe we do some stress relieving things we desperately need... but maybe we don't remember it so well?"
"It's-" she stammered nervously. "It's not that easy Anon. He-... my husband does't deserve this."
"Yes he does!" He shouted. "If he acted like your husband and gave you what you needed you wouldn't even consider this, would you!?"
"I'm... I'm not considering it..." The dodgy tone of her voice gave away her dishonesty.
He'd had enough of this back and forth, it was now or never. He gently, but purposefully laid her on her back as he crawled on top of her.
"H-hey..." She wimpered meekly, "we shouldn't... we can't." He could feel and smell her warm breath as he inched closer to her quivering lips. When he approached for a kiss she hesitated, but after a moment she closed her eyes and gently pursed her lips.
When their lips finally met it was incredible. They were soft and a little moist, very much like a person's. He gave them a few gentle pecks, then started prodding with his tongue. She briefly resisted, but shortly gave in, letting his tongue slither into her mouth.
He held his middle and index fingers up and opened his mouth signaling he wanted her to do it. She hesitated, but reluctantly opened her mouth like he wanted. He placed his fingers into her mouth, and explored it. When they were dripping wet with spit he dragged them down her belly and placed them gently on her pussy. He buried his head into her neck and bit sofly while he rubbed.
He rubbed in small circles focused at the top. He wasn't sure if ponies had a clitoris it was his first time touching one. He got a hint of the pungeant smell, and the urge to taste it struck him. He brought the fingers back to his mouth and sucked off the juices.
"Hey!?" She bemoaned with hushed unease. "Don't taste it... I'm not exactly fresh out of the bath."
He locked his stare on her and drug his hand back down plunging his fingers deep inside her. "Ah..." He wriggled his fingers around, and when they were covered in her juices again, he brought them back to his mouth and sucked on them purposefully.
He was getting impatient. He started crawling backwards, kissing down her chest to her belly before clamping on to her pussy. He lapped it up with vigorous fervour as she squirmed and moaned. When he was done with the lips, he plunged his tongue deep inside.
He could feel her squirm and hear her squeak. He was encouraged when he felt her hoof message his scalp. "She has to like this, right?" He thought, "if she really didn't want me to keep going she'd be more adamant about stopping me wouldn't she?"
He needed to come up for a breath, but when he started pulling away he felt a hoof on the back of his head push him back down. It took him a couple of tries to finally pull away, "Velvet I can't breath!" He gasped. "I thought you wanted me to stop?"
She was beet red and tearing up. "Ok fine! You want me to admit it!?" She shouted, and grabbed his head pulling him back down. "I need this, I really really need this!"
She squeezed her thighs around his head, "some days I get so pent up I burn everything I cook because I'm just so horny I can't think straight!" Her passionate fervor desolved into bitter resentment, "... and it's all HIS fault!"
She began to move her hips, her legs were a vice grip on his head. "twenty years and you're still burning dinner?" She sneered. "Well maybe if you would FUCK ME once in a while I wouldn't be so scatter-brained!"
He struggled and finally pried her legs apart and freed his head, "Are you trying to suffocate me!?" He snapped and gasped for air.
She grabbed the bottle of wine with her magic and took a long, and loud guzzling drink. When she was done she pushed it into his chest, "drink up Anon-" she slurred "it's yer' lucky day!"
"Uh... you ok?"
She sloppily wiped her chin and then reached for his pants. She started fumbling with his belt, "I'm saying you get to fuck me, that's what you wanted isn't it? Or were you just teasing a washed up old mare?"
He was shocked, he'd never have guessed she had this side to her. She had such a sweet motherly personality. "Uh, no... I think you're beautiful-" he stammered.
"Well then let's see it!" She shouted, getting frustrated with his pants. "Come on, momma needs some lovin'!"
"You could just use magic, " he scoffed to himself. He took a big drink from the wine and leaned over to set it on the table, then pulled his shirt off and tossed it away. He quickly and easily undid his pants and let his erection flop down onto her belly with a satisfying slap.
"Oh..." She cooed and rubbed it with both hooves. Her eyes widened, she bit her lip and spread herself open, "come on... I can't wait anymore."
He spit into his hand and moistened his cock with it. He held himself up with one hand, positioned his dick into the entrance of her pussy with the other, and as he laid down on top of her he slid it in as far as he could get it.
"Mmmmmh" she pleasantly moaned, and draped her arms around his neck.
It had been way too long, her warm, wet pussy felt better than anything he'd ever had even before he came to Equestria. "Oh god, mare pussy is the fucking best" he said under his breath as he thrusted as hard and deep as he could.
She squeeked and cooed in rhythm with his thrusting. He felt it coming, and he knew already it had gotten away from him. It was too late to stop it, and after only a few moments he blew his load in to her pussy. He trembled and collapsed on top of her.
"What?" She asked worriedly, "what's wrong, what happened?"
He didn't want it to be over already. He caught his breath for moment, then gave it few test thrusts. It still felt amazing. "Nothing, " he panted, "roll over."
He helped flip her on to her stomach, propped her up a bit, and kept going. Taking her from behind made it even tighter. He could hear the squishing of his cum as he thrusted, it just made it even better.
"Wait, " she said between pants "it feels like you already came..."
"I did, " he grunted, and gave her flank a hard smack. She stifled a squeek by biting on one of the throw pillows, "and I'm gonna' do it again!" He added aggressively.
He gripped the base of her tail and used it to pull her back into his cock. "Hey, " she said softly "d- do it again?" She asked timidly and rubbed her flank.
He gave her rump a brisk smack. He heard her yelp with pleasure despite trying to push her face in to the cushions to muffle it. "You like being spanked? You're someone's mother you dirty mare." He teased her.
He picked up the pace, giving her a periodic spank to her muffled approval. He loved watching the glistening pink flaps of her pussy drag out across his dick as he pulled back, as if they were clinging to him.
He decided to stop for a moment. He pulled out and just gazed at her open pink hole. "Hey," she asked "why did you stop?"
He brushed his fingers through her mane as he laid back on top of her. "What do you think of my young cock ma'am?" He teased her.
She avoided his gaze, "don't ask me that idiot..." After seeming to get her embarrassment under control she gave him an arrogant smirk and wiggled her rump against him, "is that all you've got? It's not nice to keep a mare waiting."
He sat back up on his knees and pulled her butt up higher. "I guess you won't care if I stop holding back then?"
He was much more aggressive now. He yanked hard on her tail, and smacked her ass as hard as he could. He squeeled and moaned "harder... harder!"
"I'm cumming again, " he said breathlessly. "I want to see your little pony pussy overflowing with my cum."
"What!?" she whined sensually, "what if I get pregnant?"
"It's too late for that," he replied and gripped her hips tight. "You just enjoy this warm feeling you're about to get."
He thrusted fast and hard, the rhythmic slapping reverberated around the room. He only faultered when he began pumping his cum into her. He got a few final thrusts in before they both collapsed into a quivering, sweaty mess.
"Just... just this once... Ok?" She panted.
He wouldn't remember much of the rest of the night. They drank, he knew that much. The other shoe would have to drop eventually, but for now they didn't have a care in the world...