Kerberos177 - Your Sister's Friend (Twilight)

>Be Anon
>And you are trying to get some sleep.
>It doesn't help that your sister is throwing slumber party in the room over.
>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 peaks her head in.
>Her hair is a dark purple with a pink highlight.
>She looks cute.
>Even her face is flawless, no pimple to be seen.
>She looks around your room, then she looks straight at you.
>Your eye is barely open, so it still looks like you are sleeping.
>Seeing 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.
>You release her from your hands.
>"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.
>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 seems really embarrassed about his.
>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.
>Not everyday when someone hands you their underwear.
>"T-thanks."
>She takes your underwear in her hand.
>"By the way, my name's Twilight."
>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.
>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?"
"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 your teenage hormones.
>Your heart starts to speed up as you 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 she 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 have 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.
>She 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 her 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."
>Her 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 warps around the shaft, feeling how hard it really is.

>"It's really warm."
>She eyes ever 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 more than 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 really heavy after that.
>You lean up as much as you can and give her a smile.
"By the way, that was amazing."
>She 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 starts going faster 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.
>She makes no move to stop you.
>As soon as you make contact, she lets out a small gasp.
>Deciding to experiment, you start to squeeze and massage her boobs.
>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.
>Putting more pressure than 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.
>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.
>You speed up going faster with every time your fingers hilt.
>Adding another finger you start to go faster.
>"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 one 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.
>She 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 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 the more you go.
>"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.
>He walls 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 ever 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.
>Must be a spooner.
>You oblige with being the big spoon.
>She wraps her legs around one of 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.