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...
He woke up the following morning with a headache, it actually wasn't as bad as he was thinking it would be. What he truly dreaded was the state he would find Velvet in. He'd been really pushy, like, border line rape pushy.
He was in the guest bedroom. He searched the floor for his clothes, he slipped on his pants but couldn't find his shirt. He noticed another bag open on the floor, was it Velvet's? When he finally gathered the nerve, he stood up and left the room.
He heard the sizzle and smelled cooking food. He made his way to the kitchen, and to his surprise, she seemed to be in a great mood.
"Oh! Good morning!" She greeted him sprightly. "Breakfast is almost ready, you must be starving after the night we just had!" She giggled.
She was merrily cooking him breakfast like a newlywed house wife, and that wasn't all. She was inexplicably wearing a set of nylon stockings.
"Uh... hi." He rubbed his eyes and tried to process what was happening. He fully expected to find guards waiting to clap him in irons for rape. Had it been more mutual than he remembered? "What's with the stockings?"
"Oh these? I had them in my overnight bag." She brushed back her bangs. "What do you think?" She asked bashfully.
"I vaguely recall you saying you didn't want to do it again, " he said and tried to adjust the hard-on in his boxers out of an uncomfortable angle. "Did you mean that or not? Because the stockings are really doing it for me..."
"They are!?" She chirped excitedly, then restrained herself and played it cool. "I mean, of course they are why wouldn't they? Why do you think I put them on?" She ran her hoof up her hind leg to her rump and gave it a little smack.
He stood up abruptly and marched over to her. She flinched, unsure of what he was going to do. He knelt down and scooped her up in his arms, "HeeEEEeeey!?" She shrieked. "Y-y-you can't just pick me up! Where are you taking me!?"
He carried her to the bedroom and dropped her on the bed, it creaked as she bounced. "Hey wait-" but he didn't, he crawled on top of her again and started kissing her neck.
"Wait..." She murmured softly. "I left food in the oven..."
"Fine, hold that thought." He groaned as he got up. On his way out he stopped at the door and turned back, "in fact, I want you to masturbate."
"Wh-what!?"
"You'd better be rubbing your pussy when I come back in, " he said with a deviant grin. "You're mine this weekend, get it? You'd better do what I say or I'll have to punish you..."
He could see her excited smirk as he turned to leave the room. He walked as briskly as he could out to the kitchen. He quickly twisted then knob and headed back to the guest room. When he got close he crept up to the door and peeked around to see what she was doing.
"I thought I told you to masturbate?" He said wickedly as he came into the room. He was having a lot of fun with this.
She fidgeted on the bed, "well I-... I guess I need to be punished then?"
He knew what she wanted, he sat down next to her and pulled her over his lap. He gave her a hard spank "AH!" She yelped.
"You want another one don't you?"
"Y-yes..."
"Tell me you've been a bad mare."
"I've been... I've been a bad-... I can't do this it's embarrassing!" She covered her beet red face. "I'm a gradmare!"
He was trying really hard not to laugh and she noticed. "You're laughing at me!?" She whined.
"I'm sorry," he stifled his laughter. "Lay on your back, I've got another idea."
He stood up and walked around to the other side of the bed. To her confusion, he leaned over, grabbed her arms and dragged her to the edge of the bed so her head hung off the side. "Hey- what are you-"
He let his pants and boxers drop around his ankles. She gazed upside down at his hard dick twitching over her face. He placed a hand on her chin, gently opened her mouth, and softly placed his balls in. "Suck." He ordered, "uh... please."
He wanted to play the dominant role that he had instigated, but it was still Twilight's adorable mom. It was hard to bring himself to be mean to her.
She on the other hand, seemed eager to play along. She enthusiastically sucked and mulled his balls in her mouth. He let out a moan that wasn't very manly. He cleared his throat and grabbed one of her legs. He kissed and ran his cheek up and down it.
He placed his hand on her chin and carefully pulled his balls out. He backed up, she hung her mouth open and stuck her tongue out encouraging him. He slid his cock deep into her throat.
He drew it out and pushed it in, slowly at first. He grabbed her legs and licked her hooves. As his thrusting got progressively faster the slurping got louder. He was sucking them now, and as he inched closer to orgasm he let her legs go and wrapped his hands around her throat. He didn't pull out, he pumped it all down her throat, and as soon as he was done he quickly pulled it out.
She coughed and choked, but she wasn't mad he made her swallow it without even asking first. "I think I'm in love..." he thought, as he crawled onto the bed next to her. They spent a while catching their breath, and she cuddled up next to him.
Velvet held up her leg and gazed at the stockings sorrowfully. "I wear these for Night Light all the time," she sighed. "I wish he liked them the way you do..."
"Velvet, I don't know what the hell is wrong with your husband but I think he's lost his mind. If I was your husband you'd have to beat me off with a stick everyday."
She giggled, "oh yeah, we never really discussed what we'd do if, well, If I get pregnant."
He laughed, but cut it short when he saw that she wasn't amused. "Well, in the human world people can't produce viable offspring with ponies. I don't see why biology would be much different in Equestria. I don't think you have to worry about it."
She sighed, "if you say so."
He placed a hand on her belly and gave it a playful rub, "well if I'm wrong I already know you're a great mother."
"I'm still married Anon, " she pouted. "I don't want to have a baby with you. I still don't know what I'm going to do about Night Light..."
"I'm not gonna' tell you what you should do," he said and brushed her disheveled bangs. "It's your decision, and I definitely have ownership in this. If you decide to tell him what happened I'll be there with you. I won't let you face it alone."
She smiled gently, "you're a sweet boy Anon. I don't understand how you could be having trouble finding a good marefriend." She thought it over for a moment, then seemed to come to a realization, "what about Twilight?"
"Huh? What about her?"
"I know she's a princess now, I bet that makes asking her out kind of intimidating, but I'm sure she'd love to have a special somepony as kind as you."
"Oh man," he fantasized "a threesome with Twilight and her mom? I'd be the luckiest bastard alive."
She gave him an icy cold glare. "I'm- I'm obviously joking!" He laughed it off nervously. "I think she's out of my league anyways."
"That's not true..." She replied gently. "But, on second thought maybe you should stay away from my daughter." She added coldly.
He couldn't get upset, he'd definitely earned that. The breakfast she was making had gone cold by the time they came back to it. He took the blame, apologized, and had some anyways.
For two more days he savoured her... as often as she would let him. The overwhelming stress and hopelessness he'd wrestled with felt like a distant memory, like another life. By Sunday night he was already planning his apology to Applejack. He'd been so pent up for so long that it hadn't even occurred to him that he should just try to level with her. For the first time in a long time he had hope for his future here...
....................................................................
Monday morning... After obsessively cleaning every inch of the castle they'd come into contact with, they stood anxiously at the base of the steps to the castle waiting to greet Twilight and her father as they returned.
"Thank you..." He said out of nowhere. She gazed up at him, perplexed. "I know you probably think I only said most of it to get you to sleep with me, but I really did need that. I've been bottling up a lot of anger and doubt... I was worried about how much longer I could keep it up. I think I'll be ok now thanks to you."
He met her gaze with a genuine smile, "if it doesn't work out I'd marry you in a heartbeat." He said jokingly, but part of him actually meant it.
"You're a sweet boy Anon," she replied, "but I'm an old maid now. You'll find a nice young mare soon. Just treat them like you treated me and I promise it'll happen." After a moment of consideration she added, "on second thought, maybe don't come on quite as strong..."
They shared a laugh, and when they were done they could make out two ponies coming down the road with bags in tow. As they closed in she nuzzled his leg and whispered "thank you for the wonderful weekend, I won't forget it" and she rushed off to meet them.
"Hi dear, " she greeted her husband nervously and gave him a big hug. "How was your trip? Did Twilight have a good time?"
"Yea we had a great time, " he replied. "You're in a good mood huh? You two must have had almost as much fun as we did."
Walking up behind her, Anon couldn't resist the urge, "I think we had way more fun than you guys." He said with a big grin.
Velvet shot him a murderous glare, her eye twitching with rage.
"Really?" Twilight asked sincerely. "That's great mom, what did you guys do?"
"Um-" Velvet panicked, "n-not much dear, we just... talked. He's a great listener."
"Well maybe you guys could hang out more often?" Twilight offered. "Everypony could use a good friend."
"Especially your mother, " said Night Light. "I was thinking about getting her a cat just so she'd have something to do besides lounge around the house all day."
Anon watched Velvet. He expected to see her pained or furious, but she was neither. She was gazing at him, she turned to her husband and said, "you know what dear? You deserve to have fun. Whenever you feel like going out I'll see what Anon is up to, how does that sound?"
Night Light was surprised, but he smiled. "Well, Anon, I know I'm putting you on the spot here, but you think you could keep her company if I decide to go out?"
He and Velvet locked eyes, and with a devious grin he replied, "sir, it would be my pleasure..."
