Chapter 1
Well... today was the day. The day that all foals both dreaded and welcomed.
The first day of school.
Pickle Barrel stared at the classroom door, 2-B, the same room as the one his older brother and twin sister told him to find, even giving him a note with it written on it. Feeling a bit nervous to see who's in his new class, he sighed and entered the room.
He noticed some kids from his class last year, although he never really became friends with them. The teacher was a dark blue earth pony mare, and from reading the chalkboard her name was Mrs. Essence.
His twin sister sat at the back left of the classroom, and supposedly left a seat empty for Pickle Barrel. So the colt trotted over quickly and said hi, taking a seat next to her.
He opened his saddlebags and pulled out a book, his diary. He rolled his eyes before closing it and beginning to pay attention in class.
School Day 1: Hello, Diary. Still can't get over the fact that my older sister bought me this instead of a journal, but hey I can't get mad, she still got me something to write in.
Anyways, this year I've decided to write every day after school about my day. I got the idea from my other sister Barley, my twin. She told me that it's good to write to keep myself busy and that it helps with my social anxiety.
Speaking of my twin, we somehow got lucky this year and we're in the same class. It was bound to happen eventually, we both went through grades without being in the same class. But it's still great to happen this year.
The first day of school wasn't that bad, (it's a Wednesday by the way) but could have been better. I don't get the point of everypony introducing themselves on the first day. Mrs. Essence, my new teacher, had everypony play a game... which wasn't really a game. We all had to take turns telling everypony our names, where we're from, and one of our hobbies. Long story short, I froze when it was my turn, and I got funny looks as usual. Luckily, my twin sister introduced us together, which made me feel better.
Day 2: Hey, Diary. Haven't made any friends yet, but we finally started some lessons in school today, Math and Equestrian. I helped my sister with Equestrian and she helped me on math, the same thing as last year. I'm honestly so lucky we're in the same class, otherwise, like before, I would have to wait until lunch or when we got home to get some help. She always had a friend in her classes to help her out which made me a bit jealous.
Day 3: Nothing interesting happened at school today. Instead, when I came home, my older brother and twin sister disappeared for the entire night. I wondered why because I needed help with some math. I can't get over the fact that we already got homework, even if it's the weekend. But thankfully, my older sister helped me out.
Day 4 (Next week Monday): Back in school today, writing before class starts. Honestly not feeling well today, should have stayed home. I want to write about something that happened to me on the weekend, but I don't want any secrets on this diary, in case some sneaky twin sister of mine tries to read it.
Day 5: Okay, screw it. On Sunday morning I woke up later than usual, and my... private parts were acting weird again. I can't believe I'm writing this down, but hopefully, no one gets ahold of this and reads this. Maybe I should get an enchantment that locks the book unless it's me or something, but that would probably cost a lot of bits.
Day 6: So I think I'll have to ask someone when this is going to stop. My private parts I mean. I remember looking at a book in the school library about it in the summer when it first started, that 'sex' and 'puberty' thing. But apparently, everyone in my grade knows about it already. (I didn't ask them directly, I overheard some colts talking about it and some fillies giggling about it.) I could never approach them about something as embarrassing as this.) I might ask my big brother about it tonight.
Day 6 (Midnight): So that was a lie, I didn't have the guts to ask him about it. Now I would've had to wait until after school to ask my big bro. But now we're starting something in school called 'Sex Ed'. So I might not have to after all.
Day 7: Our class started the new subject today, and most were mad that we had to substitute gym for this course. I think I was one of the few that didn't complain.
Also, something weird about my twin was happening in Sex Ed. She usually tried her hardest in all of the courses she was apart of. But today she looked so bored. Like whatever the teacher said didn't matter to her. I'm honestly kinda worried about her. Maybe she's sick.
Day 8: It's Friday, and there was a Sex Ed pop quiz! Yay! Being sarcastic by the way. I didn't do terrible on it, I got a B. The question I got stuck on was something about safety. Apparently eating some medicine is more helpful than I thought. But something that was shocking, was that my twin got a perfect score. Yesterday and earlier today she didn't pay attention at all, instead deciding to play with a pencil, or draw something on her notebook. When I asked her how she did it, she shrugged and told me she learned all about this stuff last year. Then after a while, I eventually asked her, (when we were alone,) if she knew anything about my private parts since they still kept getting hard at home. (Thank goodness it never happened at school, minus when it happened when I was in the washroom.) She told me that she could show me how to deal with it at home.
Now, Pickle Barrel sat in his and his sister's room on their bed, his red sweater that was not being worn was placed on the ground next to his sister's clothes. He patiently waiting for his twin to come back after she said she'll grab something. He watched her enter their big brother's room and heard her looking for things. But one thing was on his mind, she told him to "think about what you like the most about fillies." That was when he realized he didn't know what he liked about fillies his age. They were cute and adorable, and sometimes annoying, but that's all he could think about.
His train of thought was interrupted when Barley Barrel came back, with something in her hoof.
She smiled up at him and climbed the bed, Pickle Barrel noticed that the thing she was holding was a magazine with a beautiful mare on the cover. She looked down at Pickle's crotch which was still nothing special, her twin oblivious as his eyes were on their brother's adult magazine.
"So? What do you like about fillies the most?" Barley asked.
Pickle Barrel scratched his ear, thinking for a second. "I don't know. They're cute I guess?"
Barley looked at him for a second, before giggling. "I meant body parts silly! Do you like butts or pussy?"
Pickle tilted his head. "Pussy?" He asked, and was slightly confused at the 'butts'.
Barley laughed. "I told Drum Barrel we should have included you. But he said you weren't ready yet."
"What? Included me where?" Pickle asked at the mention of their brother.
"Anyhow." Barley sat to Pickle's left, her side brushing against his, a little too close Pickle thought. She laid down on the bed and Pickle followed suit. She then opened the magazine, and immediately PIckle blushed.
There were multiple mares showing themselves off in the book, in the strangest positions.
Slowly, Pickle's colt part grew in size, and he noticed instantly.
"It's happening again!" He reached over and covered himself with his blankets so his twin couldn't see.
Barley chuckled. "That's normal, Pickle. I was trying to get it to do that."
"Why?!" He asked.
"Because that's how sex works!" She enthusiastically said.
Pickle was confused so Barley did what she thought was best, and pecked him on the cheek for reassurance.
"Can I show you?" She asked.
Her twin, after contemplating for a bit, finally said, "Sure."
"If you want me to stop during any of this, let me know, okay?" She told.
He nodded.
Barley carefully removed the blankets off of Pickle. Revealing his crotch and hard dick. It pulsed as soon as it was exposed to the air and Barley's eyes.
"Sit back and relax okay?" She said, and he complied, laying back and spreading his hind legs a bit with the help of Barley's hooves.
She sat down on her haunches between his legs, licked her lips and started stroking his dick.
Pickle recoiled a bit but realized the sensations weren't painful but in fact, felt good. He found it a bit weird that his sister was touching him in his most private of areas, but since this was 'sex' and it was normal, he had to trust his twin and let her continue.
"You like it? Want me to stop?" His sister kindly asked.
"Y-yes." He said. "I-I mean! Keep going please!" He said with a moan, which his sister thought was cute.
"Okay." She said before starting to use two hooves. Stroking him up and down.
Then, mere seconds later, she bent forward and licked the tip of his dick, tasting some of his precum.
"Ah!" Pickle jolted. "What was that?"
Barley just continued, licking his dick like a lollipop, starting to have longer licks from the base of his shaft.
Then she again changed her methods, opening her mouth and starting Pickle's first blowjob.
He moaned, confused as to why his sister was putting something so dirty in her mouth but didn't ask any questions since it felt amazing.
She bobbed her head up and down, sucking her brother for the first time. She had to admit, she was enjoying herself too. Every time she bobbed her head down she took him in a little bit deeper.
Before she continued any further, she stopped sucking and asked, "Would you like to see something cool?"
Still in a daze of pleasure, Pickle nodded.
She let go of his dick, much to his displeasure, and turned and showed him her butt and own filly parts.
Pickle blushed. Her filly parts were coated in something that he couldn't recognize, it was dripping onto the mattress they were on. And if he took his gaze off his sister's behind, he would have noticed the little wet spot on the sheets right where she was sitting.
"You like it? If you lick my pussy it makes me feel good too you know." She said before stepping back and pushing her backside into Pickle's face.
"So this is a pussy..." He noted, starting to lick into her cunt and tasting her nectar, causing Barley to moan, which was a great sign to continue.
Meanwhile, Barley resumed the blowjob, this time having a better angle so she could take more inside her throat. She could see Pickle's hind legs squirm in pleasure, which meant he was getting close. She sucked on him hard and licked his tip every time she bobbed her head him, earning a moan from her twin brother.
Pickle was too focused on his job, and he grabbed her behind with his hooves and hugged her closer. He hadn't noticed the stirring in his loins that kept rising in power until it was too late. He tried to get his face out of his sister's ass, but she wouldn't let him, and that was when he erupted, spurting his goods all inside Barley's mouth.
And she drank it all, it tasted so sweet to her. Almost divine. When his first orgasm ended, she pulled her head up and his cock popped out of her mouth as she began panting after swallowing his delicious cum.
"Oh my, Celestia!" Pickle started when he got his face out of his tired sister's pussy. "I'm so sorry sis! I didn't mean to pe-"
Barley turned her head, locking her lips into his and sitting on his lap, his soft dick slightly touching her pussy. Their kiss was deep and was another of Pickle's firsts tonight. The two moaned as they kissed for a while, Barley taking the lead and Pickle always following suit, getting a bit of the taste of his cum off his sister's tongue.
Soon, though they needed to breathe, so Barley ended the kiss. "That..." She panted with a lewd smile. "...wasn't pee, Pickle."
"It wasn't?" He asked, equally as out of breath as her.
She shook her head. "That comes out when you feel so good you can't contain it anymore. It happens to Drum Barrel every time! It's called an 'orgasm'."
"Really?" He huffed. "Wow."
That wasn't the end of it, however. Barley wouldn't let it stop there.
She pulled the blankets up and over the both of them and told Pickle, "Now do me, please. Make me orgasm!"
So with her head against the pillows, her twin dove down under the blankets and started to lick her again when she guided his head with her forehoof.
"You can- ung! Go deeper with your tongue." She said, pushing her brother down between her legs.
He grabbed hold of her legs and kept going, sticking his tongue out as far as he could. Hearing his sisters moan louder.
"That's perfect! Keep going!" She yelled.
Pickle stroked her leg as he ate her out with his right hoof, and grabbed her butt with his left.
His sister's moans were at her peak, and after a scream of pleasure, she squirted towards her brother's mouth.
Following what she did when he orgasmed, Pickle opened his mouth wide and let her cum rain down, drinking it up greedily, but didn't swallow it all, wanting to give some of the sweet juices to its owner.
Shortly, she was finished and pulled her brother up to lay next to her, initiating another kiss on the lips. This one didn't last as long as their first, but it wasn't any less incredible. The two tasting each other's saliva mixed with some of their cum still in their mouths. Between the two mouths, they swished the fluids like mouthwash and moaned loudly while doing so. Eventually, however, they had to catch their breath.
"That was amazing, Barley." Pickle said to his cute as fuck sister, laying on his side facing her, his hooves being used as another layer of pillows for his head.
"Wasn't it?" She said, her forehooves curled up to her chest, before noticing that her bro's dick has begun to harden again. "But that isn't why your privates get so hard."
Pickle blinked. "It's not?" Blushing as his erection was full mast between the two.
"Nope." Barley blushed as well as she began to rub circles on his tip with her hoof, Pickle flinching at the pleasure but keeping his hooves as pillows. "We're supposed to put your private inside of mine." She explained.
"H-how?" He asked. "It's too big!"
Barley stroked his cock with her left hoof as she reached over with her other hoof and grabbed the magazine again. She flipped over to a page and stopped stroking, showing her brother a picture. "See? That's how it looks. And it might not look like it, but my privates can stretch a lot. I've put... bigger things in there before."
"T-then let's do it!" Pickle said, showing more spirit than usual.
Barley beamed. "Then what position do you wanna do?"
"Position?"
"Yeah, we can put your dick inside my pussy at different angles. Here..." She flipped through the book again and showed her brother a variety of angles.
"U-um..." Pickle stuttered as he looked through them all. 'Cowpony.' 'Dog Style.' 'Slope.' 'Shuttle.' Then he said. "I wanna do it... while looking at you."
"Why?" She asked, genuinely. "Still nervous?"
Pickle shook his head. "I want to see you feeling good, it makes me feel nice."
Barley smiled with a blush. "O-okay then." She turned so she was laying on her back. "Come above me." She instructed. "We're gonna try the one called 'Missionary.'"
After taking a quick glance at the magazine and the picture showing the stallion on top of the mare, he got up and over his sister. Like in the picture, he leaned down and hugged her, legs under and around her hoof pits to hold her shoulders, giving her a quick kiss on the lips. He then looked down and aimed his dick at her pussy. "Tell me if I need to stop, okay?" He insisted.
She nodded.
So Pickle began to move his hips forward, his rock hard cock entering her folds. She squirmed a bit under him but told him it didn't hurt that much, only a bit in the beginning. He kept going deeper inside her, his medial ring nearing her entrance. It felt so warm inside of Barley. So warm and extraordinary. At that moment he knew he never wanted to come out of his sister.
She raised her hind legs in reaction to the pleasure of her brother getting deeper into her. Her right hind leg twitched as she felt his medial ring spread her for a second before entering her, signaling that he was close to his max potential.
Then, their crotches hit each other and to the both of them, it felt like they were bonded for life. Barley moaned, kissing Pickle again. "You did it." She said.
"W-what now?" Pickle asked.
"Keep moving your dick in and out. But try to keep inside of me."
"Like a drawer?" He asked.
"Y-yeah. And when you're going back in, go a bit faster."
So Pickle did just that. He brought his hips back and stopped before his dick was free of his sister. He was a bit disappointed that her warmth left him, but as soon as he humped her, he didn't regret it. He felt insane amounts of pleasure and watched his adorable sister's blushing face twist up in bliss when he struck her.
"Faster." She said.
The brother picked up the pace. He fucked her more quickly as was his breaths. The two moaned as their crotches kept slapping against one another, the yellow fur above their privates brushing against each other but not quite tickling.
Pickle could feel his sister's hard teats every time their bellies came together, the thought of touching his sister in the most explicit ways in the most explicit places was making his hard-on throb instantly.
Barley moaned louder as her brother pounded into her. She felt his balls slapping against her ass and anus every time, and she was loving it! After this, she wanted to suck on his sweaty balls like the greatest sister she could ever be.
The two stared at each other, blushing madly, before both diving in for another big kiss. They moaned into each other, and never want this to ever end.
Pickle felt his sister's hind legs at his sides and flushed at the intimacy in this situation, for how close the two of them ever were. Then he felt it, that sensation again. He was about to orgasm again.
He pulled back from the kiss. "Sis! I'm close!" He told her.
"I-... Inside me!" She shouted back.
And Pickle didn't refuse. He made one last push forward and nutted deep inside Barley's pussy, and into her uterus, curling his hind legs from the heavenly feeling.
Barley wrapped her hind legs around her brother's back, and hugged him close, giving one last soft moan as she felt his load bursting inside her.
The two laid there together for some time. Barley's legs dropped as she couldn't keep them in the air anymore, and Pickle didn't want his weight to hurt his sister, so he slid his now flaccid dick out of her with a pop, and flipped off of her to her side.
Without words, the two laid in the afterglow of the amazing sex they just had, and Pickle Barrel reached outward and grabbed his sleepy cute sister, her behind covered in their cum, hugging her close to his chest, his wet dick felt a bit cold on both their bellies, but they didn't care.
He too felt a bit drowsy and didn't know why, but he took his blankets and covered the two to get warm. Barley moaned one last time and snuggled up in her brother's chest, her wet and used pussy against his wet and soft dick, before the two fell asleep.
Day 8 (After School): I just had an amazing day with my sister today...