It was late Friday night at The Cove as Pip stood behind the bartending station, getting ready to call it a night. The Cove had a bit of a swashbuckler theme going for it. The dozen or so tables scattered about looked like the steering wheel of a pirate’s ship. All of the seats, including the ones near the bartender’s station, looked like they were made from barrels or driftwood to go with the theme. On the walls were several pictures depicting drunken sailors from various eras of Equestria’s history. Some of the older ones showed sailor ponies with missing teeth, harassing the serving wench while spilling there apple rum all over the place. The newer ones, by contrast, looked more like photograph depicting the sailors in more modern day attire playing cars and sipping hard cider. Also on the wall were pictures of Princess Luna and Princess Twilight. The two had been recently asked by the owner a few weeks ago to have their pictures taken for The Cove while wearing pirate attire. Since they had known the owner for years they agreed and now those picture were on display. Luna’s had her wearing an outfit that exposed her sexy cleavage while holding a cutlass in her teeth. As for the adorkable purple princess, she was wearing a similar get up but showing her midsection instead as well as holding two pistols. Also hanging on the walls were various items like cutlasses, pirate flags, a phony treasure maps. In the middle of the bar were four pool tables that were in prime condition, just waiting for a group of ponies to play a friendly game on them.

It had been Pip’s parents who had bought this place back when he first moved to Ponyville from Trottingham. Back then, the zoning laws had kept any establishment like this from being in town and thus forcing them to be situated in its current location. But this didn’t stop ponies from coming all the way out here to get a good buzz. No, every day ponies would be milling about the place laughing and having a good time with plenty of beverages to choose from. And Friday night, that was their biggest night of the week. Ponies would come here to start their weekend off with a good kick, drinking and playing games until the owners had to close for the night. It never got to the point where ponies were destroying property or anything like that which was the good type of fun you’d expect from the ponies that lived in Ponyville.

It was only a few years ago when Pip’s parents had decided to retire and move so some southern beach town while handing over the keys to The Cove to Pip. At first, Pip had hesitated in taking this position. It had always been the pinto’s dream to sail around the world and perhaps have an adventure that involved finding some long lost treasure or the like. Or, perhaps, join the Equestrian Navy for a few years just to get sea life out of his system. Yet the more he thought about it the more running this place made sense to him. Buying a sea worthy boat was going to be expensive. Then there was all of the supplies he would need not to mention help. At five feet tall and having the build of a twig, he would need all the help he could get. So Pip quickly came to the idea that if he ran this place well enough he could make enough money to get everything he could need and in the meantime do something about his lack of muscle.

And, at first, business was looking really good. That was until a recent event. A few months back the zoning laws had changed for one reason or another. This allowed new business to enter the town and that, sadly, included bars. And it didn’t take long for a stallion name Kegger to open up his own place in town called Wild House.

Pip had been in this place only once so far and, for him, that was enough. With its bright flashing lights that would threaten to give a foal a seizure, loud music that hurt his ears if he stayed in there too long, and a hazy mist that hung in the air so much it made it hard to see he felt sure the place would bomb. And it probably would have if not for the trilogy of cheap booze, convenient location, and serving mares in skimpy attire.

Now Pip was serving a third of its usual crowd. These were ponies who were loyal friends of his, wanted to go someplace where you could hear the pony next to you, or simply preferred good drinks instead of the watered down stuff they served at Wild House. He wasn’t making as much as he used to, but thankfully he wasn’t in the same position Rarity had been a few years back. He was still making enough to pay the bills to keep the place running while also putting food on the table.

Right now there were only two ponies in the bar, Snips and Snails. Both of them were at the pool table, arguing about something. Neither of them had been served anything other than water since they had yet to pay their tab. Something that Pip made sure to remind them every time he saw the pair.

Just when Pip was about to tell them he was closing for the night the door suddenly opened. Turning his head, Pip saw a shiny crystal unicorn mare with a pink coat and aqua blue mane who was wearing a bright yellow dress that gave her just enough warmth during these early spring nights. Besides her was another pony whose identity was hidden behind a cloak and hood.

“Pip, darling,” said the mare loudly as she enter and made her way to the bare while her companion followed. “Oh it has been far too long since we had last spoken.”

“Evening Miss Matchmaker,” said Pip respectfully as the two took seats at the bartending station. He then turned to the stallions. “Ok guys, time to hit the road.”

“Ah, can’t we stay a little longer?” begged Snips. “Please?”

“Sorry, but we’re closed now,” said Pip as he shot his thumb towards the door.

“Ah, but what about them?” asked Snails.

“They get to stay because we have business to discuss,” said Pip. “Now go on. I know you both have work in the morning.”

Pip waited as the two newcomers took up seats at the bartending station. As they did that, he kept his eyes on the two who were leaving, wanting them out of here before he spoke to Matchmaker. What he was doing right now wasn’t outside the law nor was it anything that might get him in any trouble, but it also wasn’t something that he wanted the whole town to know about. It was only when the door closed that his attention returned to the two seated in front of him.

“Can I take this off now,” said the pony in the cloak. Judging by the sound of the voice, it belonged to a mare. There was something about the voice that was almost dreamlike due to its beauty and made Pip want to see who was beneath the hood.

“Not yet dear,” chided Matchmaker. “Let us settle our business here first. Then Pip can see that darling face of yours.”

As the cloaked mare moaned right before planting her face on the bar table’s surface, Matchmaker’s horn began to glow. A moment later a stack of documents appeared in front of her. Looking down, Pip saw that each one had ‘Matchmaker’s Mail Order Brides’ written in big friendly letters at the top of each page.

Some would say that what Pip was doing right now was the act of a desperate stallion. And, if Pip was being perfectly honest, he was. Ever since he was in school, very few mares ever gave him a chance manly due to his size. He had gone on a few dates, but they were pity dates. As time went on he tried things like speed dating and placing a personal ad in the paper in the hopes that there would be some mare in the area who would give him a chance. With each failure drove Pip into a silent desperation until he considered getting a mail order bride.

Matchmaker Mail Order Brides was the best in Equestria. Heck, Princess Cadence even gave this agency public approval which was saying something. However, despite this, Pip still felt uncertain so he decided to head up to the Crystal Empire to talk to Matchmaker in pony. After talking to each other for over two hours, Pip left the agency with a much lighter wallet and the promise that she would find him the perfect bride.

“Now then,” said Matchmaker as she went over her documents. “Finding you a bride was, admittedly, trickier than I had thought. Normally, most of my mares aren’t that picky and would love to have a stallion as young as you are how owns his own business. Yet your size did give them doubts, I’m afraid. But, when I talked to this little gift from Celestia she wanted to head over here right away and meet you. Isn’t that right dearie?”

“He is cuter than what you described,” giggle the cloaked mare and causing a warmth to spread through Pip’s body.

“Y-You really think so?” asked Pip as he leaned a bit closer.

“I said it, didn’t I?” she purred. Her voice, it was just…seductive. There was no other way to describe it. Even though he had never seen her face, a part of him was already falling in love. He didn’t care if it was a changeling under that cloak, he would gladly give her all the love he had as long as she continued to talk to him like this.

“Alright then,” said Matchmaker as she slid a form in front of Pip and then another in front of the cloaked mare. “I will need you both to sign this before we get…” Her voice trailed off as the other mare had already scribbled her name at the bottom so quickly that the other two ponies were surprised the paper didn’t burst into flames. “Er, started. But before you sign, I want you both to know that there is a trail period of three months before this is finalized. Just so you can both familiarize with each other. Once the three months are over I will be here with the needed paperwork so you will both be legally married. Now, are there any questions darling?”

The cloaked mare shook her head, however Pip did have a concern. “I know we talked about this last time,” said Pip. “But, just as a refresher, what happens if one or both of us realizes this isn’t going to work?”

“Well,” began Matchmaker, “things like that do tend to happen, I’m afraid. And if it does, all you have to do is send me a letter and I’ll back here on the next train. I will then try to find you both new matches. Or if Pipsqueak here doesn’t wish to try again I will give him an 80% refund. Now I hope that settles any concerns you might have.” Pip simply nodded. It was then that Matchmaker placed a hand on the cloaked mare’s should. As if this were a cue of some sort, the mare took off the hood to reveal her smiling face.

Pip could feel his jaw drop as he looked into her smiling face. She had a simple grey coat with a long, black, and bouncy mane that went well past her shoulder. It wasn’t a very unusual coloration, he had seen many mares that looked very similar. However it was her other features that marked her as a thestral that drew his attention. Like her golden slit eyes that commanded his attention or her cute, tuffed ears. Even her tiny fangs seemed to enhance her features. Pip was so taken by her that he failed to notice when Matchmaker pushed the document in front of him. Now he knew why she had been wearing a hood up until this moment. Had she not, all of Pip’s focus would have been on this mare.

It took Pip three tries to sign the document, mainly because he didn’t want to take his eye off of her for a moment. The first time he signed the bartender table and the second time his signature was so illegible that he had to cross it out. Each failure earn him an enchanting giggle from the mare.

Sweet Luna, it’s like she has a spell over me, thought Pip as he finally managed to sign the document.

“Congratulations Pip,” said Matchmaker as she took the document. “For the next three months you will be the husband of Succubus.”

“And this is where we will be living,” said Pip as he opened a door at the end of a stairway leading up from the bar. For Pip the place was fairly average and bare. Just a kitchen/family room with three bedrooms and a single bathroom. Furniture wise there wasn’t much as his parents had taken most of it leaving him with a couple of beds, a couch, and a few bookshelves. Not that he really needed them or anything since he only came up here to eat, sleep, and shower.

Yet the bareness of the place didn’t upset Succubus. She let out a squeal of joy as she raced into the kitchen and began to examine everything with a large smile on her face, as if she were seeing everything for the first time. She even hugged the tea kettle as if she had just found her long lost teddy bear!

Looking at all of this, Pip couldn’t help but wonder about his new wife as he gently closed the door. Along with this behavior, he noticed that Succubus hadn’t brought anything with her. Not a suitcase, backpack, or even a plastic shopping bag of personal items. The only thing she seemed to own were the clothes on her back.

Maybe she came from a poor family, thought Pip as he watched Succubus head over to the couch where she proceeded to bounce up and down on it. I did hear that some mares sign up to become mail order brides in order to escape poverty. Maybe-

It was then that Succubus tossed aside her cloak while happily laughing, causing Pip’s brain to crash in mid-thought. Under that cloak the thestral mare was completely naked! Every inch of her body was completely exposed for him to see. Her breaths were huge, at least a large D or perhaps an E in cup size that bounced along with her. Pip felt his mouth open slightly as he saw that her large coral pink nipples were stiff as if begging to be stuck on. This was odd since thestrals shared the same lean, aerodynamic bodies that pegasi did. The only exception that he had ever seen before was Fluttershy.

Slowly, Pip managed to pry his eyes away from the bouncing jugs to look at the rest of her. Her stomach, he noted, looked soft and rounded to the perfect feminine shape. Resting on her fine flank was her cutie mark which looked like a heart with one side red while the other was black. Her legs were neither too fat nor too skinny, once again giving her that perfect feminine figure that any stallion would drool over.

“You like what you see?” asked Succubus. Pip jumped slightly at her voice and quickly focused his attention up to her face. Her expression was one of delight with eyes that seemed to sparkle with pure happiness. If he were to look down once more, Pip would have spotted a thin trail of juices running down her legs.

“Y-Yes,” said Pip with a gulp.

The smile on Succubus’s face seemed to double in both size and joy when she heard him say that. She then jumped off the couch towards him with wings extended. When their bodies collided Succubus wrapped her arms around his neck while bringing her lips to his. Pip didn’t seem to notice that he had crashed against the ground or had the weight of a full grown mare on top of him. All he could registered at the moment was her softness. Both her lips and arms felt so full and soft against his body that he closed his eyes while getting lost in his first real kiss.

It was then that Succubus pulled back from the kiss and moved her head slightly so that her mouth was next to his ear. “Don’t close your eyes sweetie,” she whispered. “I love it when you look at me.” To this, Pip obeyed and was rewarded with another kiss. This time was different as she added her tongue, licking the outside of his lips in a slow manner.

Pip opened his mouth to moan as her tongue created small bursts of pleasure only to be silenced as she invade this open mouth. Her tongue was now tracing everything from the roof of his mouth, to his teeth, and even his own tongue. Several times the small station let out a whimpering moan as he did his best not to close his eyes. The sensations she was creating felt so different and new that it was overwhelming. Then, after what felt like hours, Succubus pulled away while leaving her our tongue pointing out so that it created a strand of saliva.

“Poor baby,” she said while moving to straddle his waist, her fingers now wrapping around the bottom of his shirt. “Why are you still dressed? Here, let me help you.” With one swift motion she pulled upwards on his shirt to expose his non-muscular chest. Soon the shirt was completely off of him and thrown…somewhere. Pip didn’t know because he was too focused on Succubus had instantly leaned forwards again so that she could kiss him while her hard nipples pressed against his chest.

While Pip did his best to keep his eyes on Succubus as he lay there, still struggling with the realization that this was happening. He was clueless as to what he should do or even could do for that matter. He knew that with some mares a single mistake could ruin the mood. And that was something that the pinto stallion really, really didn’t want. He wanted to continue feeling her warm, soft body against his. To feel her tongue as it explored his mouth.

After a while, Succubus removed her tongue from Pip’s mouth. Before Pip could let out a moan of disappointment, the mare was already planting small kisses from his cheek to his neck. Pip couldn’t help but squirm as he felt a mixture of lips, tongue, and fangs against his neck. With her lips pressed tightly against his coat, Pip could feel Succubus grinning at what her actions were doing to him.

Soon she was on the move again, kissing and licking his chest. Her hands softly traced his sides for a while, moving up and down in slow motion. Eventually they found their way to his pants and before he knew it they had been removed without her ever taking her body away from his. Now his stiff member was pressed against her body which slowly continued to slide down his. With his lower body free of any type of clothing he could feel her wetness against his legs as she made her way to his upper pelvis, kissing it tenderly along the way.

Craning his head, Pip watched Succubus as she continued downwards towards his hardened rod. He could feel it as his member moved through the valley of her soft mounds as her lips made their way closer to his groin. As got to his hips, Pip fought hard not to buck up hips upwards as bolts of pleasure were created with her kisses alone. Then, finally, his member was sadly freed from the confides of her breasts. Succubus then lowered her head and, for a time, just stared at it with an odd expression on her face. As she did, fear and panic made their way into Pip’s thoughts. He knew he wasn’t as big or as thick as other stallions. Let’s face it, not every stallion will be as gifted like Big Mac or those stallions in the porno magazines.

Succubus then used her hands to take hold of her breasts. Pip’s eyes widened as she took her right breasts and pressed her nipple against his shaft before. Slowly she then began to trace it up and down his rod while her left nipple was brought to her mouth. He watched as she stuck out her tongue to circle around it slowly while moaning. Pip longed to sit up, reach out, and use his tongue instead. Or perhaps they could both swirl their tongues around the same nipple. Was that even possible? However he found himself unable to move as he continue to watch her as she switched breasts.

Eventually, Succubus decided to shake things up a bit. Bringing both hands to the tips of her breasts she then brought her nipple together right above the head of Pip’s cock. With a smile she then pulled them apart a tiny bit before lower them. Pip let out a shudder as he felt her rock hard nipples as they traced the side of his cock and then another as she pressed them together at the middle of his member. As she did this, Succubus brought her face closer to the head of his cock until she was so close he could feel her hot breath against it.

“I’ve never done this before,” she said. “I hope you like it.” With that said, Succubus opened her mouth to take in the tip of Pip’s member while stroking it with her tits.

Pip’s answer came in the form of both a shutter and a moan. He could feel both the hardness of her nipples as well as she softness of her breasts as she made her slow motion strokes. And then there was her mouth. By Luna her mouth! It was so warm and moist that soft whimpers of pleasure were constantly escaping his mouth. He could feel Succubus sucking on the head softly as her tongue twirled around the head. It took every ounce of self-control he had not to throw his head back.

As Succubus continued to pleasure Pip, the blissful stallion began to notice something about her tits. For some reason they seemed to be a bit moister and that at the end of the nipples seemed to have small white spots on them as if she were lactating. As he stared at them, he imagined himself taking charge for a moment resulting so that he could suck on those tits and drink her milk. However, when Pip blinked he saw that the white spots were gone making him think that what he had seen was simply a trick of his horny mind.

After a while, Pip clenched his teeth to keep his orgasm from happening. He could feel his pre-cum leaking out and, from the look in the sexy mare’s eyes, Succubus knew it to. She released his member from the combined hold of her mouth and breasts allowing it to smack against his body. She then took one of her breasts and placed it against the exposed underbelly of his cock. For a moment or two she just kept it there, waiting for Pip’s breathing to become more controlled. Once it did, she placed a hand on her breast to move it up and down his shaft in an effort to stroke him.

While not as intense as what he had already received, Pip found this to be very enjoyable as well as erotic. It was keeping him well aroused while not being strong enough to push him over the edge. Soon she switched breasts, kissing his cock and then her breast right before doing so.

“Do you want to cum soon baby?” she asked as she rubbed her breast against his cock, her voice so sultry that it made him harder. Unable to say anything, Pip simply nodded. “Oh, that’s good because I want you to cum baby. But not now. Just hold on until you’re inside of me so you can fill me up with all your delicious cum!”

With that, Succubus removed her breast from his member causing Pip to groan in frustration. But that feeling was soon replaced with anticipation. If what she said was any indication that meant that he was now going to lose his virginity!

Yet Succubus neither stood up nor crawled on top of him. Instead she crawled backwards soon more so that now she was in-between his legs. Very soon he felt her breath against his balls followed by her hand lightly cupping his sac.

“Oh my,” she purred right before giving his sack a quick lick. “Look how big these are. And soon all of that will be inside of me!” She paused once more, this time taking one of his balls into her mouth. He could feel her fangs lightly against the skin of his sack which added to the excitement of what was happening. Then he could feel her tongue as it tasted this previously untouched flesh, causing her to moan while sucking on it slightly. Pip could no longer contain it as he let out a scream of pleasure as his head fell back to hit the ground. Once the scream ended he began to pant wildly as his hands dug into the carpet.

Succubus released her hold on him before standing up. As she did, Pip noticed that there was a light sheen of sweat on her that caused the lights to reflect off of her coat. It was then that he realized that he too was covered in sweat and that the temperature of the apartment had risen significantly. Funny how he didn’t seem to notice until now. All of his focus had been on Succubus.

It was then that Succubus took a small step forward so that her hips were above Pip’s. Both of their breathing increased as she did this. Pip could feel himself getting hotter and he could tell her body was getting warmer as well. Large beads of sweat were now appearing all over her body. Several of these beads rolled down her lovely breasts where they pooled at her nipples before falling onto him. Succubus then reached down to her lower lips with both hands and spread them apart for her new husband to see.

“Do you see this?” she whispered in a husky tone as she lowered herself downwards. “This is where your dick is going to go to make me your mare. And I’m going to make you my stallion. It will make me very happy.” Once she was low enough, Succubus reach out with one hand to gently take hold of Pip’s dick and position it so that it was standing upwards. Slowly she continued to lower herself, stopping only when her moist petals touched his rod. She then looked at him.

“Is this what you want?” she asked, her voice almost sounding fearful. It was like she was afraid he’d reject her.

It was then that Pip knew that he had to do something other than lay there. Taking a breath, he moved his arms so that his hand could touch her hips. He caressed them gently before saying “Yes”.

Smiling softly, Succubus began to lower herself to allow Pip’s cock to enter her. As soon as his flesh entered her the two hissed and groaned in delight. Pip fought hard not to close his eyes, to keep them on his wife as she so very slowly descended. The texture of her inner walls was like nothing he had ever felt before. Warm, silky, and wet all at the same time. It was both amazing and instantly addicting.

Then, Succubus stopped as Pip’s member hit a wall. He blinked in confusion for a moment, wondering what this was since he was sure he could go in a bit deeper. He watched as the mare above him raised herself a bit, took a breath, and then lowered herself with enough force for his dick to break through the barrier. Succubus’s hand flew to her mouth as she suppressed a scream and Pip could see the tears beginning to appear in her eyes.

“Are you alright?” asked a worried Pip as he tried to get up. “I-If I hurt you I’m sorry. Bli-” Before he could get any further, Succubus flung herself forwards to wrap her arms around his neck while forcing them both against the ground.

“I-I think it-t’ll only hurt for a bit,” she whispered into his ear. “At l-least tha-at’s what I w-was told w-when you lose your v-virginity.”

Pip’s eyes widened at the reveal of this new information. It was her first time as well? He never would have guessed that based on how she had been acting so far. It just seemed like she knew what she was doing a bit too well. Pip turned his head to look at her to ask her a question, but the sight of her face caused him to forget it. Her eyes were closed with a big, goofy grin covering her face. Slowly she began to nuzzle his face for a bit before her eyes half opened so that she could gaze at him.

After giving him a quick peck, she pulled herself up so that she straddled him again. Still looking at him through half lidded eyes, she slowly rose upwards before lowering herself again. As she did this, both of them gasped as small bursts of pleasure erupted. Succubus leaned backwards, pushing her breasts into the air while Pip’s hands once more made contact with her hips. Pip could hardly believe that that single motion could make him feel like that.

Eventually, Succubus moved again with her wings extended outwards. Her movements were slow so that the two of them could take in the full amount of delight they had while they were connected. With each bounce Pip would watch as her breasts jiggled and swayed. He licked his lips and wished right now he could reach out to them. To kneed them or suck on them while Succubus rode his cock. Perhaps, he thought to himself, she’ll let me do that in the future.

As time went on, Succubus’s movements were becoming more wanton and carnal. She was now bouncing up and down at a rapid pace with glazed over eyes with her hips gyrating every so often. Sweat was constantly forming and being flung from her body while a pool of the same liquid stained the carpet around Pip. The room was now being drenched in their combined love order but neither seemed to care about anything other than their quickly approaching climaxes.

“Pip, oh buck me!” screamed Succubus as she suddenly shut her eyes tightly. “Buck! I…I’m so bucking close. Please, mark me as your needy mare so nopony else will think about claiming me. I’m yours Pip! All you have to do now is unleash that big load I know is waiting for meEEEEEEEEEEE!” It was her words that had done it, pushed the smaller stallion over the edge to unleash all of his saved sperm into her. Pip could feel a single massive rope of cum blasting into her seconds before her walls clamped around his member. The stallion took a massive breath as he felt their combined liquids splash around his cock and leak out through the cracks.

As their orgasms began to subside, a wave of fatigue hit Pip. Even though it was becoming harder for him to keep his eyes open he could tell the same thing was happening to his wife. A smile managed to cross his face as she leaned forwards to wrap her arms around him again. While pressing her body against his, she gently kissed him on the lips before they both faded into a dreamless sleep.

Pip awoke several hours later to the sound of his alarm clock. Not feeling like getting up just yet he attempted to hit the snooze button without opening his eyes. When he felt carpet instead of his wooden nightstand, Pip’s eyes opened quicker than a sonic rainboom explosion. He looked around to find himself on the floor with Succubus lying half on top of him with her arms still wrapped around his next.

As his memories returned about the previous night, Pip sadly broke free of her hold so that he could turn off his alarm. As he looked at the clock he knew it was still dark out, but in an hour he would need to open up the bar for the Night Guard. That left him just enough time to make breakfast and get a shower in.

As he turned around he noticed his wife shivering without him there to supply heat. So, before heading into the kitchen, he snagged himself a spare blanket and placed it on top of her.

About fifteen minutes later, Pip had put on some shorts and had several pancakes on the skillet. Seeing that it would take awhile he turned around to set the table only to see Succubus standing a few feet behind him in the nude. Looking up at her face he could tell that she wasn’t fully awake. Her eyes were half closed and her mouth was slightly open allowing some drool to escape.

“Is breakfast ready Miss Night Shift?” she asked. She then slowly shook her head. “Never mind, just bring the food to my room when it’s done. That way mommy and daddy won’t see me.”

“Ah, who’s Miss Night Shift?” asked Pip. Succubus, who was in the middle of turning around when he said this, jumped into the air at the sound of his voice. Quickly she turned around while rubbing the sleep from her eyes. When she brought them down and saw Pip standing there, a fanged smile appeared on her face.

“It wasn’t a dream!” laughed Succubus as she hugged Pip tightly, his face being pushed into her bosom. Said stallion began to flail his arms around in a desperate attempt for air which was ignored. “That means that we really are married and this home now! Say are you making pancakes?” She then let go of Pip so that she could move closer to the skillet.

Taking several deep breaths, Pip turned to look at his wife who had was currently staring at the half cooked pancakes. She began to bounce around excitedly as her tail swished back and forth. While Pip still didn’t know much about his new wife, it made him happy to see her like this. In time he knew that he would learn more about her and work hard to keep her like this. But, for now, everything was alright.