You are a pretty normal student at Canterlot High, except for your hidden talent for playing chess which most don't really know about. Though you only ever played it more for a hobby rather than pursuing it. Not like you didn't have a lot of friends to play with anyway, that is until Sunset Shimmer who was the school's biggest bully who turned over a new leaf invited you to her friend group.
It was definitely awkward for a bit since you were hanging around all these popular and beautiful girls, so to say part of it being awkward was because of all the jealous stares you got from the other guys would be an understatement. Though you did start getting bullied by some of those guys your new friends would always show up and defend you, none more than Sunset. You had started developing a huge crush on her and not just because you thought she was hot, but because ever since she got with her friends she seemed to grow into a strong woman.
Ever since that Homecoming, she seemed more mature than her age, and how she handled situations was what did it for you. Since she had brought you into her friend group she really did show you how much she had changed, and as you grew closer to her the more you liked her. Though you found it difficult to tell her your feelings and it is why you had thought of a plan, even if it didn't pan out the way you wanted.
You knew Sunset was a good chess player and so far you've managed to avoid playing with her and instead you've been studying how she plays. Though you knew this wasn't fair it was an essential part of your plan. Granted you knew she might see through your ploy but you also knew she would be too prideful to back down from the challenge.
"Hey! Sorry, had to help Twilight return her last pile of books!" Sunset said as she walked up.
"No probs, did you get everything done?" You asked as you leaned against a pillar.
"Yup, so what's up?" Sunset asked giving you a warm smile that made your heart flutter a bit.
"Um, well I was thinking about playing a game of chess and wanted to see if you wanted to be my opponent?" You asked which got her to raise an eyebrow at you.
"You know how to play?" Sunset asked with an inquisitive tone.
"Hmm, you could say that but I just don't want to play a normal game. How bout a little bet?" You suggest making Sunset give a little smirk.
"Depends on the bet." Sunset replied through her smirk.
"Well, let's say the loser has to do anything the winner says for about a week. I know it's a pretty basic bet, but I think this'll be fun!" You said as you looked at her. She was wearing her normal jacket with her purple sun shirt and orange skirt.
"Hmm, yeah I think that's fine," Sunset said with a bit of a mischievous look but you weren't too worried.
"Alright, so wanna come to my house to play? My parents are out of town for the next two weeks," You suggested making Sunset give a little sideways look before she gave you a smile.
"Sure, let's go so I can kick your ass and have you do my laundry!" Sunset said as the two of you started walking toward your house.
It didn't take too long since you only lived about four blocks from the school in a nice two-story house which still seemed to impress Sunset every time she came over. Unlocking the front and entering you offered her something to drink which she took up, and after getting the both of you something including a snack you got your chess set. Sitting it down Sunset whistled as you opened the case.
"This is a Starswirl original, these things cost a fortune!" Sunset said sounding very impressed. "Shit, if Twilight knew you had this she would be begging you for it. You might even get her to do anything for it."
"Uh-huh, but yeah it actually belonged to my great-grandfather first and it's been passed down since. So, you ready to play?" You ask making her give you a confident smile as you both start setting up the board.
As you put your last pieces in place the game started and the room fell silent except for the sound of the pieces being moved as the both of you were in extreme focus mode. Thirty minutes rolled by without signs of who was winning as each side took their time with their movements. Once both sides start to widdle down Sunset piped up.
"So, about this bet... When you said the loser has to do anything the winner says, are there restrictions to what the winner can ask?" Sunset asked making you smile.
"Well, nothing illegal, but other than that you can ask anything and the loser has to do it. Granted you don't have to do it if really isn't something you're comfortable with of course," You replied, and as you looked up from the board you saw how she sitting with her legs spread open a bit where you could see up her skirt. To your surprise, she was wearing a pair of purple panties as well and with the little view you got you could feel yourself stiffen a bit.
"Hmm, well can't wait!" Sunset said as she moved her piece into the position you were hoping for. Though it took a second for Sunset to scan over the board and realize the trap she had just fallen for. "Well shit, I guess this is game."
"Yup, check and mate!" You say as you moved in.
"Ugh, well guess I will be your ever-humble servant for the next week!" Sunset said as she stood up to stretch, which revealed how short her shirt was on her as it went pretty far up on her. "So, what do you want me to do?"
It had only been two days since you won your bet with Sunset, and you've kept the things you asked her to do pretty tame at first. Though you've been getting bolder and bolder with the request which she followed without question. You were getting impatient though, and so on the third day was when you decided to make a move since she didn't seem to mind what you asked so far. Even if those things were a bit tamer than what you had in mind.
"So, what would you like me to do now?" Sunset asked as she walked back in with a drink for you. She was wearing the same outfit she had on three days ago at your request.
"hmm, well come over here with me for a moment," You say as you got up and walked over to the staircase where you had a pair of handcuffs waiting. Upon seeing what you grabbed Sunset hesitated a moment.
"A-and what are those for?" Sunset asked as you turned to her.
"Well, come over here and stand by the staircase with your arms up please?" You ask making Sunset bite her lower lip before walking forward and turning around lifting her arms up as you asked.
"Like this right?" Sunset asked with a flirtatious tone.
"Yup, now stay like that..." You said as you quickly went up the stairs and stopped where her hands were and quickly fasted them together with the cuffs.
"Hmm, me oh my, I do wonder what you have in mind?" Sunset asked as you came down the stairs.
"I think you have a pretty good idea. Now, you are going to let me do anything I want to do. Do you understand?" You asked putting as much confidence in it as you could muster.
"Y-yes master, my body is completely at your disposal..." Sunset said with her eyes lowering and pretty much purrs as she spoke. "B-but please be g-gentle master, t-this is my first time!"
"Oh, you mean too much to me for me to hurt you, my little servant," You say as you stepped closer. Though you did have to wonder if she was just role-playing or if was serious about it being her first time. There was one way to find out, and with how you had her she was now sitting down comfortably.
Once you were right in front of her and locked eyes with her as she gave you a cute innocent look which only made you gulp a bit. You took a deep breath before squatting down in front of her still maintaining eye contact while placing a finger under her chin. Gently rubbing under her chin before going in for a kiss Sunset returned in full.
Breaking the kiss you leaned back looking at her in her vulnerable state, from the way her shirt was pulled up nearly revealing her perky breast to how she had her legs positioned as if she was a helpless victim. She really was a good actress but you knew now wasn't the time to admire her, it was time to take advantage of the situation. You reached out your hands cupping her breast under her shirt which she was wearing a purple lacey bra.
"O-oh master..." Sunset gave a little moan as you grouped her. You quickly undid her bra and realizing with her jacket and shirt on you wouldn't be able to fully get it off. "P-please d-don't cut it..."
"A-are you sure?" You asked, but you shook your head knowing you had to keep the act up, even if she was playing along. "Of course, I'll cut it off!"
You quickly grabbed your pocket knife to cut the straps of her bra and tossed it to the floor and put your knife back into your pocket. Now that her breast was fully exposed you resumed playing with them for a bit. Though you were growing impatient once again as your own needs were growing so you stood up making Sunset give you a frightened look that was mixed with excitement.
Grabbing your shorts you pulled them down revealing your hardened dick as it bobbed in front of her, but once she registered it and how big it was she let out a gasp. For a moment she seemed genuinely concerned with it, and sure you were above average on the size you didn't think it was that big of a deal. Though it did hit you that she must have been telling the truth, this will be her first time.
"This really is your..." Sunset only nodded at that as looked away for the moment. "Not to worry little servant, I very much prefer not to break my favorite toy."
Before she could speak again you went in for another kiss, this one turned far more passionate than the first one, and as you broke the kiss again, this time with a trail of saliva between the two of you. Standing back up you lined the tip of your member with her mouth and gently pressed inside of her mouth. She didn't offer any resistance as you entered her mouth and with her mouth around your member, you moaned out.
"Oh fuck Sunset..." You said as you pushed even deeper into her throat, which caused her to gag a bit but after a moment she seemed to grow accommodated with it. The feeling was pure bliss for you even as you begin to withdraw from her lips though she seemed to follow you a bit which only made you shiver.
She seemed to moan around your tip making you thrust a bit back in making you moan louder and looking down and locking eyes with her only made it that much more pleasurable. You really hadn't realized how badly you had been neglecting yourself as you were already starting to feel the pressure building. What's more, was that she was keeping up your rhythm and after a few thrusts she made sure to take a little extra which finally got you to bust the dam.
"S-suunset!" You moaned out as you grabbed the back of her head holding her still. She let out a gasp as you unloaded into her throat making her swallow rope after rope. "Y-yeah... d-drink up... fuucckk!"
You pulled out as you went half limp looking at the beautiful girl in front of you and wondering why she would let you do this to her, but at the same time, it did make you wonder how far you could push it. Once she managed to catch her breath you helped her stand up and as she locked eyes with you once more you moved in for another kiss, this time pushing your tongue into her mouth making her give a slight moan. As you were doing that you placed one hand on one of her breasts to fondle it while the other slipped between her legs and up her skirt.
"Nnggh!" She moaned out breaking the kiss as you traced her slit through her panties. "Y-you have such a... nngh-ah!.. touch!"
"Thanks, I've been taking some lessons on massages," You bragged as you pressed deeper into her making her squirm and moan louder. It was really hard to control yourself from just taking her as she was making such cute faces just from your teasing.
Though your skills haven't been fully explored yet as you moved her panties off to the side to allow your fingers better access to her soaking-wet entrance. You gave her a sly smile as you traced her slit with your bare fingers making her moan even louder as it allowed you to press deeper. Eventually, two of your fingers sunk to the first knuckles which seemed to drive her crazy.
"Gah! C-cum..." She moaned out tensing around your fingers making you smile as it told you how sensitive she was as her juices splashed down your hand.
"And here I thought I was the only one who was a bit sensitive," You chuckled as she rolled her eyes.
"I-I haven't touched myself in awhile master, I-I was hoping you would take advantage of me like this..." She said that in a teasing tone as she stood there with shaky legs.
"That must have been intense since it seems you're already having a hard time standing. Now I wonder what would happen if I stuffed this inside of you..." You said as you stepped forward pressing your rehardened dick between her thighs and rubbing against her slit making her moan and you shiver. "Now, it's time to get rid of these panties, they're way too in the way."
"Y-you just have a magic... ngh... touch master," She said as she shimmied her hips to help you remove her panties. Before she could say another word you kissed her once more, which was broken up by her moan as your pressed your tip against her entrance.
You locked eyes with her and she nodded giving you permission to enter, and you both let out loud moans as you stretched her entrance around you. She strained her arms in her cuffs a bit as you pushed further inside. Eventually, she yelped in pain making you stop mid-thrust looking down at her and seeing her grimace as you moved a bit making you realize you had just popped her cherry.
"M-master... i-it hursts b-but feels so g-good..." She moaned out, though you could tell it hurt more than she let on. So you gently gave her a kiss playing with her breast waiting for her to adjust to your girth. "I-I think I-I'm ready m-master..."
Hearing that and looking at her you knew she was telling the truth and so you pulled out a bit making her wince slightly before thrusting back inside. This caused her to let out a long moan as you managed to get a little more than half inside of her. She was extremely tight around you and you couldn't believe you manage to fit so much inside of her, and the feeling made you moan out yourself.
"Y-you're so dammed beautiful!" You moaned out as you slid back out and slammed back into her and fully bottoming out in her.
"Gggaaahhh!" She screamed out which transitioned into a silent scream as she came around you. Her tunnel squeezing and convulsing around you and made you nearly bust right then, but you managed to hold out until she finished.
You gave her a smirk as she looked up at you through somewhat tired eyes as you pulled back making her wince before moaning out once more as you began to go into a rhythm. Though you knew you weren't going to last long as with her tightness and her recent orgasm you were already close again. Though as you thrust back into her she let out another ear-piercing moan as she clamped down around you once more.
"S-Sunset... g-gonna..." You started to moan out.
"P-please m-master, I-I w-want t-to feel it..." Sunset managed to get out in between her moans which caused to bottom out in her and unload deep inside of her. Her eyes rolled to the back of her head as her tongue lolled out of her mouth as the pleasure overwhelmed her as rope after rope of your cum shot into her.
As the two of you came down from the bliss of your shared orgasm you once again kissed her before pulling out of her making her moan as a loud pop echoed through the room as you popped out of her. A rush of your cum came flowing out of her as she lost balance making you catch her. It took her another few minutes to recover enough to stand on her own.
"T-that was r-really intense..." She said as she leaned against you.
"Oh, it's not done yet. I think I can go one more round, how about you?" You ask making her give you a slightly concerned look, but after a moment she nodded her head. "Good, now let me undo these handcuffs first then I want you to bend over the couch."
"Y-yes master..." She responded, a bit of hesitancy in her voice though she did as you asked.
You walked over to her as she bent over revealing her round ass which you promptly grabbed making her jump a big. Moving her skirt up to reveal her skin you really did have to appreciate how nice her ass was as you slid your length between her legs sliding against her slit once more. This caused you both to moan out once more, though you were only doing it to get more lubed up.
"I hope you're ready for this next part my servant," You whispered into her ear as you pulled back and lined up against her tight asshole.
"M-master, I-I d-don't think... Nnggaaahhh!" She screamed out as you pressed and entered her tight hole making you moan out. "P-please... t-too b-big..."
You stopped where you were which was about a quarter of your length and as you looked Sunset had some tears forming making you realize it was hurting her. Though you really wanted this, so you wrapped a hand around and started rubbing her slit causing her to moan out. It wasn't long before she started to loosen up allowing you to push deeper into her ass making her moan more in pleasure now than pain.
"M-master!" She moaned out once more, her body going completely stiff and it seemed as if she had stopped breathing as she was letting out a silent moan as her ass clenched around you.
"Ffuucckk!" You moaned out as you once again unloaded deep inside of her ass, and your orgasms seemed to last for an eternity until finally, you both came down.
You both collapsed to the floor in complete exhaustion as your dick finally began to shrink and eventually pop out of her ass on its own. She cuddled up to you which got you to embrace her and really you just couldn't believe it actually happened. As the two of you lay there on the verge of sleep Sunset spoke up with the word you had been hoping to hear.
"I am really glad you finally made your move, 'cause I really do love you..." She said as she started drifting off to sleep.
"I love you too my little servant..." You replied and joined her in sleep.
