Author's Note

Writer: Blue Breeze

Trigger list: Anal, butt massage

Beach Shack

Well, you didn’t picture this for your weekend off. Reclining in an inner tube, sun beating down on you from above in a comforting warmth, gently swaying in the water as you listen to others enjoy themselves around you in a frenzy of fun and excitement. The weather was nice for a mid-summer day as you watched all of your friends and classmates enjoying the private island Diamond Tiara invited you all to. Maybe she was actually changing into a half-decent pony? Maybe not, but at least you’re enjoying yourself without having to worry about school or summer jobs or anything of the sort.

You had imagined after school ended you’d be busy all summer working under a relative, filling out applications, or trying to hide from all that nonsense. After all, this had been your last year of high school. College and adulthood were only around the corner now, so you had to savor the time you had left. You weren’t entirely sure why Diamond Tiara of all ponies would shell out for the class to use her father’s private resort, but why complain?

“So, you enjoying yourself?” Silver Spoon asked from your side. “Looks like you’re relaxing a little too well.”

You open an eye quizzically toward the mare, a bit bothered to be taken out of your bliss. “What makes you say that?” You question.

“Well, everypony else is running around and you’re just sitting there. You gonna get up anytime soon?” She replied.

You shrug, grinning as you go back to your blissful position. “Hey, ponies have their own ways of enjoying time off. This is my way.”

“I see.” Silver Spoon looked down at the sea. “Mind if I grab a tube and sit with you?”

You thought it a bit odd she wanted to join you of all ponies, but you saw no harm in it. “Sure, help yourself.”

She did just that and floated next to you, occasionally bumping tubes together. The warm sun and the tropical feel in the air made you feel calm and cool, and so did Silver Spoon from the looks of it.

You had known Silver for a number of years, since about middle school when you moved from Fillydelphia to Ponyville. You were only kids then, but now you had both matured into young adults. It was funny how fast life seemed to fly by.

After a few minutes of silence between the two of you, the mare next to you brushed her hand next to yours, which you didn’t mind, until she attempted to hold your hand. You instantly pulled it away, but Silver didn’t notice.

Thinking over a thought you had, you decide to break the silence. “Hey, Silver?” You ask the filly, opening your eyes to look towards her.

“Y-yeah?” Silver looked back, staring into your eyes.

Oblivious to her stare, you continue. “You’re Diamond Tiara’s best friend. Any clue why she brought us all out here?”

“She was acting super nice to the Cutie Mark Crusaders, and she invited them to this island, but one of them wanted every student in the high school to go, so she brought us here.”

“And why has she been so nice lately?” You continue. “Not to sound rude, but she’s not exactly known for her generosity around the school.”

“I dunno what’s gotten into her lately. She just seemed so nice and friendly.” She answers.

You further thought it over. It was hard to wrap your head around, but maybe Diamond really was turning over a new leaf… Or this was some sort of elaborate ruse to prank everypony. Too soon to tell, so you were gonna keep an eye out.

“Any other questions you’re dying to get the answer to?” She asked slyly.

You take a minute to ponder anything else, but decide to let it go and keep enjoying this time while you have it. “Nope, carry on.”

“Good.” She simply said as she stared off into the sea, still floating next to you.

Without you really noticing, the ocean waves begin to pick up a little bit. Before long, you feel your tubes rock back and forth a bit more forcefully. Soon after, a large wave crashes into your tubes, sending you and Silver both off of your tubes as the waves forcefully push you to shore.

As you feel yourself stop on the sandy beach, you feel something sizeable on top of you. Coming to your sense, you open your eyes and blush furiously at you see. Silver Spoon is resting atop you, still shaken up by the wave. Her perky breasts are lightly pressed against your chest, giving you a view of between what cleave she has. You guess they’re about B’s, but a strong B.

But what you really take notice of, as you realize where where you’re holding, you have one hand cupping the filly’s soft rear end. You're not sure what to make it, but your body does. The softness of her fur against your fingers and the slight give it has beneath you drives your brain crazy.

You resist getting a rock-hard boner, which rubs on her panties, and probably her possibly wet vagina inside the blue bikini bottom. You know you’re just about to get made fun of, but the sensation of her breasts on you, holding her ass, and the boner brushing feels so good and so right, but you could care less right now.

You’re only able to enjoy this moment a bit longer before you notice Silver starts getting up, making you promptly remove your hands before anything incriminating can come about.

Silver takes a moment to realize what happened before turning rosey on her cheeks, quickly climbing off you. “Oh, I’m sorry!” She says frantically. “I hope you’re okay. Are there any broken bones or anything?”

You shake it off as you pull yourself up, dusting the sand from yourself. “Nah, I’m good. Just got some water in my ears is all.” You joke as you tilt your head, trying to remove the water that was never there. Hopefully she doesn’t realize you just felt her up.

Silver Spoon looked away in embarrassment and ran away, probably to her rich pink mare friend. Before too long, the sun began to set, prompting Diamond to invite everyone in for the remainder of the night. It was more of before, with mares and stallions partying, listening to music, enjoying food, and playing a few party games. Snips and Snails attempted some tricks for the crowd, but that resulted in a few broken vases. Nothing that couldn’t be replaced.

As the night went on, everyone soon became worn out, retiring for the night. Luckily there were two cabins to stay in; one for boys and one for the girls. You unloaded your stuff below your bed and tucked yourself in, planning to get a good rest for tomorrow.

You felt a light tug, then your whole body gets thrown into your own sheets, being wrapped inside like a taco. You felt the temperature drop some, realizing you’re outside and you’re being kidnapped by somepony, or some ponies. You attempt to struggle free, but that only results in them dropping you with a thud before attempting to carry you again.

Within a few more moments, you feel yourself get placed down on a surface-a bed of some sort. You hear a door shut and a light flicks on. With a flick, your sheets are removed and you can see again.

“What the hell is going on?” You say in frustration, not seeing your assailants yet. You rub your eyes to adjust to the light, revealing Silver and Diamond, still in their swimwear as they smile deviously at you. This only leaves you more confused.

“H-hey.” Silver Spoon shyly waved.

“So, you want to fuck my best friend, right?” Diamond Tiara asked, snarky.

“Wait, what?!” You ask in further confusion. You look towards Silver, who blushes as she looks back.

“I-I sorta told her about what happened e-earlier on the beach.” She explains.

The realization hits you almost as hard as your blush does as you look away and rub your neck awkwardly. Guess she did notice.

“You have to go through certain...tests, if you wanna ever take each other’s virginity.”

Diamond untied her bra and fully took it off, revealing her C cup breasts. You started to get a boner from her bright pink nipples staring at you. You didn’t know why, it just turned you on, even if you weren’t fond of the mare they were attached to.

The pink mare pulled down her panties and picked up her feet to grab the bikini and throw it on the bed, fully revealing her ravishing nude and ungodly sexy body.

Diamond snickered as she saw you lose yourself to her nearly flawless figure. She knew they had you to do with as they pleased. She decided to lie on the bed beside you, getting flat on her stomach and moving her tail aside to give you a nice view of her firm ass. A lifetime of dieting and trying to keep up her figure gave her bottom a shape most mares only dream of.

She whistled, getting you to look at her eyes. “Silver tells me you have a thing for a fine ass. Since I see you staring, why don’t you give mine a nice rub down?” She commanded, lightly brushing her tail across your face, getting you to blush again.

“W-what? Really? C-can I get naked for this, or is that too far?”

“Hmmmm, nah. I don’t want your little friend coming out too soon.” You look down, noticing your stiffy rubbing against your pants. “Now rub my ass.” Diamond commanded again.

You walk over and get on the bed, still staring at the beautiful behind that belongs to the rich mare.

“Don’t be shy. Put your hand on it and start rubbing. I won’t bite.” She winked, getting another rise out of you.

You look over to Silver, who’s just sitting there, watching you intently. You feel some kind of romantic connection with her when both her and your eyes meet.

You look back, placing your hands on Diamond’s fine rump. It was warm, not too warm though, but you enjoyed the heat of it. It felt fuller than Silver’s, filling out your palms and curving around your fingers. You start by rubbing up and down her twin cheeks, feeling them move to your touch. Diamond merely hums in pleasure as the nerves in her rear relax and sway.

As you move your hands around, your arousal only increases as ever jiggle and jostle of her ass makes you more and more desperate to dive in. But you get a hold of yourself and begin to rub in circles, making sure to feel up every inch of her curvacious backside.

“Go a bit harder. I really wanna feel you get into it.” Diamond further demands, getting excited herself.

You begin pressing your hands more firmly, squishing her butt down a bit as you really knead her booty. As you rub and push more forcefully, you can catch glimpses of her moistening slit and pink star. It makes your mouth water at the sight.

“Now, I want you to get a little dirty. Silver, please wait outside for a bit. We’ll call you in when we’re done.”

Silver Spoon simply walked out of the shack, a bit jealous of Diamond getting to go first. She knew she’d get her turn, though.

“I want you to… hit me from behind. I want you to get out of those clothes and stick your cock in my perfect, pink ass.”

That set you off. Without wasting another moment, you quickly tear off your clothes, soon leaving you in nothing but your birthday suit with your little friend sticking up loud and proud.

Curiously, Diamond took your dick in her dainty hand and rubbed it, sizing it up and driving you wild in her grasp. You wanted her to do more to you, but you’re saving yourself for Silver Spoon.

She eyes it for a moment before releasing you. “That’ll work.” She turns back around and leans over the bed, raising her glorious glutes up to you as she slyly watches you from over her shoulder.

You were ready to dive in, but you knew you were no animal. You noticed a bottle of lube on the side table and quickly grabbed it, using a good helping to slicken you up for entry. Now properly lubed, you take position behind the mare, lining up your flared erection to her puckered hole.

“Go ahead, stick it in..” Diamond muttered, eager to get filled.

You start by leaning in, using your hand to properly guide yourself to her upper hole. Your head makes contact with her tight rosebud, feeling it nearly resist you, even with the lube. As Diamond relaxes her body, her asses loosens for you, allowing your head to pop inside her tight canal.

You both shudder at the foreign sensation, but only embrace it as you feel pleasure rocking through your bodies. You slide in further, inch by inch being swallowed by her accepting ass until you feel yourself hilt inside. You can feel the heat of her pussy wafting over your balls as they rest against her.

Diamond moans your name several times as you begin to thrust inside her back door. You had to take a little advantage to the situation, so you rub her thighs and slightly squeeze them. You moaned your partner’s name as well. You couldn’t help it; your basic instincts made you.

Having felt left out, Silver Spoon cracks the door open to peer inside. What she sees sends her mind somewhere she never thought of before. Without even thinking, she draws a hand down into her panties, lightly massaging her engorging mound as she wishes she could be Diamond right now.

Hearing the noise despite your own, you look back while continuing to thrust to see Silver stimulating herself. She instantly squeaks in surprise, but you simply smile at her.

“Feel free to join in.” You offer her, motioning her to join. Silver gulps in excitement, quickly stripping herself of her swimwear and rushing over to you.

Diamond was currently too distracted by your humping to care that Silver had wandered in. While you continued to bang Diamond’s butt, you wrapped an arm around Silver and brought your lips together for a passionate kiss that neither of you could break.

It wasn’t long now, as Diamond could feel her climax building in her snatch. She panted from below as she rocked her hips against your thrusts.

“C’mon, hurry up! I’m close!” She ordered weakly. “...You can do it inside.”

Not wanting to keep the mare waiting, you increased the power of your thrusts, getting as deep inside her cavern as you could get yourself. Your balls furiously slapped against her tight slit as you tried to give her your all. With a deep thrust in, you buried yourself inside as you groaned out with sweet release.

Diamond moaned so loudly, you thought ponies would investigate by now, but luck is on your side for tonight. The mare’s own damn bursted as you filled her, making her entire body tingle. You take your wet dick out of Diamond’s sexy butt, making a wet noise with a strand of semen stuck to her buttcheek and the head of your cock, eventually separating.

“Y...You can have Silver for the night.” Diamond said as she got up shakily, putting on her bikini once more and leaving the shack, leaving the two of you alone.

Now with Diamond gone, you looked to Silver, who shyly looked back at you. While you were still shining in your afterglow, Silver’s body felt needy and begged for attention.

“T-Think I can have a turn now?” She asked you coyly, kissing you once more.

As the kiss broke, you took a seat on bed, spreading your legs to give her full access. “Sure, but I’m still a bit out of it. Think you can handle this one?”

She nods in response, turning around to let her butt face your half chub. Silver took her trim ass and rubbed the crack of it against your shaft, sandwiching it between her buns as they worked you to full size once more. You were still slick from your previous session and were now coating her butthole and lips with your sloppy secretions as she hotdogged you for a minute more.

Now with you fully hard again, Silver lowered her hole on your tip and cooed as she allowed herself to slide down your rod for the first time. She moaned a bit, but became silent. This didn’t feel lustful; it felt intimate and romantic, and the both of you knew this felt so right, even more than Diamond.

It wasn’t long before she took you to the hilt, feeling more full than she ever has before. She quickly began to slide up and down, raising and lowering her ass as it lightly bounced in your lap. She didn’t have quite the same figure as Diamond, but it rocked you to the core all the same.

The mare soon got into a rhythm of rising and lowering, always stopping at your tip just to slam back down again as she impaled herself on you. She handled it expertly for being her first time, and the tightness was almost numbing, it was so intense.

Wanting more stimulation, she went back to playing with her dripping marehood, rubbing her fingers against her stiffened nub, wanting nothing more than to share a mind-shattering orgasm with you.

You knew you weren’t going to last much longer. The building pressure in your tool told you an even bigger load than before would be on its way soon.

Taking one final shove of you, all the way down to your balls, Silver’s walls clenched tightly and she moaned out your name as her orgasm washed over her like the earlier wave. The clench sent you over the cliff as you released your cum inside of the sexy, silver mare that was right in front of you.

You both rode out your shared climax together before you collapsed onto the bed, leaving your shaft to slip out of her. Both exhausted and spent, you cuddled up to the mare from behind, spooning her into your embrace.

Silver Spoon adjusted so she was facing you, and caressed your cheek. “You’re so adorable up close, y’know?”

You chuckled to her and pulled your bodies closer, pressing up against one another. “You’re not so bad yourself.”

The two of you close your eyes and lean in to share a gentle kiss, softer and more intimate than before.

“I… I love you.” Silver muttered to you.

You softly smiled at the mare, kissing her head as you close your eyes to fall asleep. “I love you too, Silver.”