Your Sister's Friend

by Kerberos

Rating: mature
Tags: Twilight Sparkle, My Little Pony: Friendship is Magic, Rainbow Dash, Other, Romance, Sex, Slice of Life, Human
Length: 3588

You try to get some sleep when someone (Twilight) comes in for a surprise.

You try to get some sleep when someone (Twilight) comes in for a surprise.

Published 2014-08-06 20:30:06 UTC
Last updated 2014-08-06 20:30:06 UTC

Time for Bed

Anon POV

You are laying in your bed, trying to get some sleep. It doesn't help that your sister is throwing slumber party in the room over. She invited all her friends from Canterlot High. You were actually surprised when she said she was throwing one. She isn't the most popular girl around. What friends she does have aren't all that attractive either, so you are not in some kind of dream situation.

You roll over, trying to find a more comfortable position. They haven't shut up all night. True, you don't have school tomorrow, but you love your sleep. That's when the door to your room slowly creaks open.

You crack an eye open to see who it is. A girl slowly peeks her head in. Her hair is a dark purple with a pink highlight while her skin is colored lavender. She looks cute. Even her face is flawless, not a pimple to be seen. She looks around your room, then settles on you. Your eye is barely open, so it still looks like you are sleeping. Thinking that she is in the clear, the girl opens your door a little wider and steps in your room. Finally being able to see her figure, she looks pretty hot.So, how does she know your sister?

She tip toes closer to your prone form. You make sure to keep up the appearance of sleeping. You want to see what she is going to do. All she does is get really close to your face. She stays that way for about a minute, exchanging her breath with your's, before she moves to your dresser.

She was probably checking if you really were sleeping. Opening each drawer, it looks like she is searching for something specific. Then, she finds your underwear drawer.

"Finally." She immediately cups her mouth and looks back at you. You haven't moved an inch since she walked in the room.

She holds up one of your favorite pairs of boxer briefs. Alright, you don't care that a hot girl comes in and looks around to see if she finds anything she likes. In fact, you encourage it. But, you don't let anyone take your underwear.

You sit up on your bed as you watch her close the drawer. She turns around with a huge smile on her face. That is, until she sees you.
"Ahhh-" You rush over to her and cup her mouth.

"Shhh. You don't need to scream." You listen to see if any of the other girls heard her. Their usual chatter doesn't change, so you doubt that they did. You look back to the girl in your grip.

"You're not going to scream again, are you?" She does her best to shake her head no. So, you release her from your hands.

"Sweet Celestia. I thought you were sleeping." Giving her an 'are you serious right now' face, you answer her.

"How could I when all of you are talking all night long?" She slightly blushes and kicks the ground.

"S-sorry. I can tell them to quiet down a little." The girl tries to back herself through your door. You aren't going to let her leave quite yet though. So, you get behind her and shut your door.

"Not so fast. Now, what are you doing with my underwear?" Holding your hand out, she gives you your underwear.

"It was for a dare." She is blushing like mad. She must be really embarrassed about this. You give an amused snort.

"Is that it? If it's just for that then here." You hand your underwear back to her. She looks at you with a shocked expression. It’s not everyday when someone hands you their underwear.

"T-thanks." She takes your underwear in her hand.

"By the way, my name's Twilight, Twilight Sparkle." She holds out her other arm. You give her a handshake.

"Anon." You both stand there, not sure what to do next. Eventually, she breaks the silence.

"I guess I should be getting back. It was nice meeting you." She moves towards the door but you grab her hand.

"Wait, you don't have to go. Do you want to, sit and talk. I don't think I will be getting any sleep tonight anyways." That gets her to blush as she pulls some of her hair behind her ear. God that's cute.

"S-sure." You both walk over to your bed and sit down. She seems so nervous. So, you give her a smile to help ease the tension. When she smiles back, she relaxes a little.

"So, truth or dare huh?"

"Y-yeah."

"What's the worst dare you have gotten?" She fiddles with her hands.

"Stealing your underwear." You give a chuckle.

"That's it?" She huffs at you.

“Yes it was. What was the worst thing you were dared to do?" You lean back and remember the dare that would forever be burned into your head.

"Well the worst would have to be kissing some dude. Now the best was making out with a girl in a closet." You smirk, knowing you won this round. Twilight's blush also increased at least ten fold. She turns away from you and looks at her hands.

"I've never kissed a boy before." And so starts the teenage hormones. Your heart starts to speed up as you think about taking an opportunity.

"I could always... fix that." God, you may want to be an alpha, but you just sounded like an obvious beta. You are glad Twilight didn't catch on when she looks at you.

"You want to kiss me?" You give her the best smile you can.

"Why not? You are obviously smart if you are friends with my sister. Plus, you look beautiful." That's all it took for her to start twirling her hair.

"O-okay." She closes her eyes and puckers her lips. It looks like how a little girl thinks kissing should be. You had to keep yourself from laughing at the poor thing.

"Stop. Just stop." She pulls back with a sad look.

"I-I'm sorry if I messed up. It's just, I'm so nervous and-" You stopped her rambling with a kiss. Twilight actually jumps when your lips meet, but the hand behind her keeps you lip locked. Her fear eventually melts into bliss.

Since this is her first kiss, you don't want to go too far. So no tongue. You stay like this until you need to breathe. Even when your face leaves her's, she stays in the same position. It doesn't take her long to realize the kiss has ended.

"I guess you liked it." She nods her head. "Did you want another?"

You get your answer when she pounces on you and kisses you hard. Not wanting to be outdone, you cradle her head and hold her by her waist. She just grips the sides of your head.

As the kiss goes on, you can feel Twilight's tongue try to push past your lips. You give her some help by parting your lips. You're still not all that experienced with kissing yourself, so your tongues just moved around randomly.

She moans into your mouth as you continue your battle. She must really be getting into it. The slight dampness on your leg gives you a hint as well.

Well, you can't blame her. You are pitching your own tent.

It's not long before you both need some oxygen. You both separate again, but she still stays on top of you.

"I think... I really like... kissing." Twilight's heaving breathing is just so hot, it is making you even harder. It even pushes against her leg, and she notices. Instead of a lustful smile, like you were expecting, she looks even more nervous than she was about just kissing.

"I-Is that... what I think it is." She looks down to where her leg is touching you. Your little friend is indeed trying to give her a friendly hello.

"Y-yeah." You are a nervous about how she would take it. But, you were just making out, so she would understand.

Right?

"Could I... ummm... see it?" Her voice was so quiet, you almost missed what she said. But you did, and that make it pulse.

"S-sure." Now you are no stranger to kissing, but anything beyond that is out of your zone of knowledge. You reach down to pull down your shorts, only to be stopped by Twilight.

"L-let me." The feeling of her fingers touching your skin sends shivers down your spine. This will be the farthest you have ever been with a girl.

She hooks her thumbs under your waistband and starts to pull. Twilight moves down along with your pants until she reaches the bulge. She takes a deep, shaky breath before pulling them past. Your dick springs up and stands proudly. Twilight's eyes widen in surprise at seeing a penis for the first time.

"It's um... big." You never thought you were that big, but you let her stroke your ego. "Can I touch it?" Speaking about stroking.

"Y-yeah." Times slows as she reaches out her hand. When she comes within inches, she pulls back, having second thoughts. Before you can say anything else, she pushes forward and makes contact. The feeling is like nothing else you have ever felt before. Her soft, petite hand wraps around the shaft, feeling how hard it really is.

"It's really warm." She eyes every little bit about your dick. Every subtle shift makes your grit your teeth in pleasure.

"You can move your hand if you want." She looks up at you, then back down to your dick. Her hand starts to move up and down, in a pumping motion. This is 100 times better than doing it yourself. You face give her an ego boost, thinking she is doing it right on her first try.

She goes a little faster and some pre cum leaks out of the top. Thinking about some stuff Rarity had her read, she runs her hand over it and uses it as lubricant. The new feeling almost makes you cum on the spot. It is hard to think about anything but the girl giving you a handjob. That pressure you were holding back, now starts to build up.

"I... I don't think I'll l-last much longer." You either think she can hear you or doesn't care when she keeps beating your meat. Gripping the sheets you get ready to become a fountain. She lowers her head towards your strained dick. Then, she opens her mouth and takes in the head.

That does it.

Your balls tighten and you start to shoot your seed inside her mouth. Her eyes go wide at the first shot, but she doesn't more her head from your dick. You ride out your orgasm in pure bliss, each shot of cum less powerful than the last. When you pump out the last shot, Twilight moves her head off your dick and swallows.

That's hot.

After you watch her gulp down her mouth load, she licks her lips and fingers.

"That actually tasted good. I thought it was supposed to be really salty."

"I've been eating... more fruit lately." Your chest feels heavier than normal after that. You lean up as much as you can and give her a smile.

"By the way, that was amazing." Twilight blushes at the complement. "Do you think I could return the favor?" She bites her bottom lip and nods her head. You both trade positions, so she is now laying down. Reaching for her pants, she grabs your hands.

"W-wait. Let me take off my shirt." Your heart skips a beat when she lifts up her shirt. She's not even wearing a bra. Her breasts are what you guess a large B cup or small C cup. Big enough to be squeezed, small enough to still look perky. You can't help but bring your hands to them, and she makes no move to stop you.

As soon as you make contact, Twilight lets out a small gasp. Deciding to experiment, you start to squeeze and massage her tits. She lays her head back as small moans escape her throat. You make sure to pay extra attention to her nipples. They just feel so soft, it's like nothing you have ever felt before. You were probably doing that for a few minutes before he puts her hands on top of yours.

She pushes your hand off her glorious mounds and down her stomach. At first, you were disappointed, but you saw exactly where she is pushing you. As soon as your fingers hit the waistband of her pajama pants, you curl your fingers under the elastic. You continue your movement and bring her pants to her ankles. Her panties are soaked, but that isn't what you are looking at.

You are looking at her glistening womanhood. Now, you have seen videos and pictures, but seeing a vagina in real life is something else. It even smelled good.
You pull her pants and underwear off her. She then spreads her legs, giving you a better view.

"I... ummm... wow." She giggles at your expression.

"Now you know how I felt about your's." You inch your hand towards her sweet spot.
She bites her bottom lip in anticipation. As soon as you make contact, she lets out a larger gasp.

It is wet.

Really wet.

You can't even bring yourself to move. You are just so transfixed with how it feels. Taking a bit more charge, Twilight starts to move her hips under your hand. This breaks you out of your trance and you put more pressure on her pussy. Mistaking the amount of force you intended along with Twilight moving her hips, one of your fingers slips inside. She stops with a sharp breath and her walls clench around your finger. She is awfully tight, and you still don't know exactly what to do.

"Move it." It's like she is reading your mind. You pull out and push back in. She lets out moans and massages her own breasts. You can feel yourself start to harden again. So, you speed up going faster with every time your fingers hilts. Then, you add another finger.

"Mmmmmmm yes. Right there." You keep up the assault on her nethers. "Oh, fuck me right now." She is getting louder. You hope she doesn't alert your sister. Your thoughts are interrupted by her grabbing your dick, which has once again become rock hard.

"You. In me. Now." What happened to the girls that had never kissed before? She pulls your dick to her entrance. You start to panic.

"W-wait! Aren't you a virgin?" Your dick is now prodding her entrance. Wrapping her legs around you, she pulls you all the way in.

"Not anymore." Her face contorts in pain and her eyes start to tear up. You know about popping a cherry, but her pulling you all the way in on the first try has to hurt. Without disturbing your union, you lean over and hug her. Twilight puts her arms behind your back and digs her fingernails in. It hurts, but she is probably in more pain than you will ever experience.

You kiss her neck and tell her that everything will be alright. As fast as the pain came, it left her. Then it turned into pleasure.

"O-okay. You can move now." You stay in the same hugging position as you start to pull out. Once you get all but you head out, you slowly push it back in. You don't want to hurt her any more than she already was. Twilight hums into your neck as you continue to go in and out. Her vaginal walls squeeze and massage your member every time you enter her.

They don't like it when you pull out.

"Faster." She whispers into your ear before nibbling on you earlobe. You don't even think before your body starts to move on it's own. You are a slave to her desire, and you don't mind one bit. You speed up, making a slapping noise with your bodies. It's starting to get a bit hotter.

"K-keep going." Her breaths are hot and heavy. She must be getting closer to the edge. You're not to far behind either.

She starts to gyrate her hips every time you push into her. Her walls soon start to convulse.

"A-anon. I-I-I'm going to-" She doesn't get to finish when her walls clamp down on your member. A hot rush of fluids coat your dick.

It's too much for you. You try to pull out before you become a father, but her legs keep you locked inside.

"F-fuck!" You fill her with your seed as her walls milk every last drop out of you. Once you both rode out the last of your orgasm, you fall down beside her. Looking down at your work, a little bit of cum leaked out. Your eyes go wide and you get ready to panic, but she puts a hand on your chest.

"Don't worry. I'm on the pill. It helps with... lady things." All you needed to know was the pill before you slump back down.

"Could have told me earlier." She rolls on her side.

"Too tired, will apologize later." Chuckling, you take off your shirt and cuddle up next to her. She feels warm, and you like it.

Twilight turns to her side and pushes up against you. She must be a spooner, so you oblige with being the big spoon. Her legs intertwine with your's, keeping you close. You grab the covers, and pull it over your naked forms. Just in time to, because at that moment, your door opens to reveal a group of nerdy girls. Not the Twilight nerdy, your sister type of nerdy.

"Anon, we heard someone shouting wha-" You sister stops dead when she see's Twilight against your chest, under the covers. "Anon! What the hell do you think you are doing to my friend!?" You bring up a finger to your lips.

"Shhhh, she's trying to sleep." Your sister turns red in anger while all her other friends turn red for a very different reason.

"Ugh!" You sister stops back to her room, leaving you with the group of not all that attractive girls. One of the steps forward.

"H-hey Anon."

"No." She hangs her head and closes your door. You wrap an arm around Twilight, just under her bust and hug her close. Now you can get some sleep.

The invitation.

Twilight Sparkle POV

"I'm sorry Twilight, but I just don't understand the fascination with the Astronomy club. I mean I know you are an egg head, but still. They are even more egg headish." Rainbow leans back in her chair and takes a bite out of her sandwich. She has been getting more and more on your case about hanging out with your other set of friends. To be honest, you are starting to think she is getting jealous.

"Rainbow, why do you care who I hang around with? They have the same interests as I do. Plus, can't I have other friends beside you, Rarity, Pinkie, Applejack, and Fluttershy? Heck, you hang around Spitfire and Soarin enough." Rainbow huffs at your point. She never could outsmart you. But she could easily out sport you.

"That's different. We have to practice and train so we can win games. You just look at the stars and play connect the dots." You narrow your eyes.

"And all you do is kick a ball. But I don't want to fight with you right now. I was just trying to tell you th-" You were interrupted with a tap on your shoulder. Turning around, you see that it's the Astronomy club president. "M-miss president. What are you doing here?"

"I just wanted to hand you this." She hands you an invitation to a star watching/slumber party at her house. You make sure the it is on a Friday before you take it. "I hope you can make it."

"I will have to ask my parents, but I am pretty sure they will let me go." While you are keeping a calm collective mind on the outside, On the inside, you were screaming like a five year old. This would be the first time in your life you were invited to a slumber party. Even your other friends never invited you to one.

In fact, you don't think they ever threw one before. They were always hanging with their own cliques. If it wasn't for being friends in junior high, you doubt that you would still be together. Canterlot high has really put a strain on your friendships. Well, all except Rainbow. She is as loyal as a dog.

"Cool. The door is open at 7:00. I hope to see you there." She waves goodbye and heads back into the lunch crowd. You couldn't keep your smile off your face. Turning back to your food, you almost forgot Rainbow was still here.

"So... sleepover huh?" You give her a sheepish smile.

"Yeah. My first one." Rainbow immediately puts an arm around your shoulder.

"Well, then we have to make sure this is memorable, so I will come too. She has a brother right?" The president has only talked about her brother a couple of times. Nothing to really go off of though. So, you nod your head. "Great. Do I have a game for you."