Oliver and Wren’s First Time

by Jinxy198

Our story begins one night in Applebridge.
It was a cool autumn, leaves have already started falling. A symphony of crickets was the only thing breaking the serene silence of a quaint neighborhood.
In one house a boy named Oliver was snapped out of his sleep by a sound. It sounded like a grunt. He glanced over at his sister’s bed. It was only recently that him and his family moved into the neighborhood. Due to lack of rooms him and Wren were forced to share the same bedroom. Any 11 year old would be annoyed at the lack of privacy but it couldn’t be helped. He heard another grunt, this sounded almost like a groan coming from her bed. Was his sister having a nightmare?
“Wren?”
He saw the bed shift as the auburn hair of his big sister peek out of the covers.
“…”
“Wren?”
“…”
“WREN!”
The person in the bed jumped up from the sudden shout. Soon he saw green eyes glaring at him through the darkness. The only source of light being the glow of a streetlight peering through the blinds. The sixth grader would’ve thought she looked pretty if she didn’t look like a bear that was woken up from hibernation.
“What the heck Ollie?” She hissed. The low voice wasn’t necessary due to their parents being out for the night, leaving Wren in charge of the house till morning. The boy fidgeted in place nervously.
“I thought you had a nightmare Wren. You always comforted me when I got one.”
“Well it wasn’t so keep it down and leave me alone. Some of us have practice tomorrow.”
“Then what was with that sound you were making? It sounded like you were in pain.”
Wren’s glare suddenly cracked and showed a twinge of fear. Fear of something she didn’t want him to know, or rather something she didn’t think she should let him know.
“It’s… it’s nothing.” She said with flushed cheeks. Actually now that Oliver thought about it, from the dim light of outside, she looked rather frazzled. As he subtly leaned closer he noticed her pulling the blankets closer around her body as if hiding something. The curious mind of a child overcame his common sense.
“Are you hiding something?”
“N-no.”
“Is it something bad?”
“Well not exactly…” The words came out of her mouth before she could think.
“Aha! There is something!” He said as he jumped on the edge of the bed. “Let me see it!”
“No!” She said childishly as she buried herself under the covers. The truth was that she was touching herself. She couldn’t help it, growing into a teen has left her with a major libido for her own little brother no less. She knows it’s wrong but she’s always been in love with this cute boy that’s been a part of her life. She always tried to hide it but now that they share a room together it’s been getting more and more difficult. She would give her own soul if she would be able to try those things she saw in those videos with her bro. But life isn’t that simple.
“Wren, let me see!” Oliver whined as he fondled around the bundle of covers to find an opening. He found one and began wriggling one of his hands in.
“W-Wait, stop! That tickles!” She said suppressing her giggles.
“Then let me in!” The brown haired boy demanded.
“Never!” Oliver shrugged.
“Alright, you asked for it.” He wriggled both his hands into the space between the bed and Wren. He didn’t know what part of her he was touching but it seemed to be doing the trick.
“No! Cut that out! Please!” She shrieked as she began thrashing around under the covers. Deep down she was enjoying this. She was getting turned on, not from the tickling but from being so close to her lil bro. The thrashing got more wild as they were getting closer and closer to the edge.
“I’m not stopping till you s- GAH!” He shouted as him and Wren fell off the bed and landed on the floor with a thud. He let out a groan as he realized the situation they were in. Wren was sprawled out on the floor, finally free from the blanket. Though the lack of cover revealed a little secret, she wasn’t wearing any pants. He got a perfectly good view of her hairless slit, something he hasn’t seen since kindergarten when they used to share baths. But now that he’s looking right at it, it instilled something in him he didn’t know what to call it.
“Sis… why aren’t you wearing pants?”
Wren was mortified being exposed like this. She couldn’t think of a good alibi so she had no choice but to come clean.
“I… I was playing with myself.”
“Playing?” Oliver arched his eyebrows. Wren gave a nod in response. “Can I see?”
The older girl gave a look of disbelief and excitement.
Perhaps it was that simple after all. Whatever the case, this is a chance she isn’t going to pass up. “Um. Ok!” She squeaked. She sat up on the bed, her legs dangling over the edge.
Oliver watched with more focus than he puts into his soccer matches at his sister’s glistening pussy and as her finger went into the slit. Wren closed her eyes as she began pumping her fingers in and out slowly at first then rapidly. Her legs twitched in pleasure every so often as she tried in vain to stifle her moans.
“Wow, what are you doing?” Oliver asked.
“I’m fingering myself. It’s one of the ways you can play with yourself and it feels real good when you do.”
“Can you show me how to do it to myself?”
Wren laughed. “You don’t have a vagina dummy.”
Oliver pouted and crossed his arms. “I know that but there has to be a way for me to feel good as well. Wouldn’t be fair if you had all the fun.”
His sister tutted her lip. This was a threshold she has already decided to cross. “Alright here’s the deal, if you finger me I’ll show you a way I can make you feel good, alright?” Oliver eagerly nodded, anime stars in his eyes to match his determination. He scooted over to her on his knees, Wren’s hairless slit a foot or two away from his face. He sniffed, her musk was pleasant and fragrant like a rosebush. He slowly brought his fingers near her slit and felt a wetness around it, it was what he was smelling. He rotated his slickened fingers counter clockwise around the edge of her pussy. Wren’s toes curled everytime her little brother brushed against her clitoris. Her breathing increased as he continued to play with her. Then he inserted his index finger right into her vagina and she freely let out a moan into the night.
“Oh god Ollie that feel so g-OOD! Fuck!” She cursed as she felt Ollie insert his middle and pointer finger as well and began wriggling them like a worm. While she already know the feeling, the fact that another person was inside her excited her to no end. She just wished it was a different appendage in her. Then after several minutes of this going on he suddenly stopped. She looked at him and he had a face she’s never seen on him before. He was panting, face red, and his eyes looked half glazed. “What is it?”
“My penis feels funny…” Ollie whined like a hurt puppy. Wren could not deny him when he looked so lewd.
“Alright your turn, it’ll be easier if we are naked.”
Oliver nodded as the two kids began stripping down. Wren already had half the job done, she just removed her pink top showing off her developing breasts to the night air. She looked over and saw her brother take off his pajama shirt. She saw his smooth belly and chest, the slightest hint of muscle behind his leftover baby fat, it looked so delicious to her. Next he took off his shorts, not wearing any underwear. She saw his beautiful, hairless, 4 inch penis sticking out into the air, the head was peaking out of his foreskin. He shuffled his feet, not sure what to do next.
“You know you look really sexy Ollie.” Wren said walking up towards him. “I always wanted to do this.”
“Wren…” He moaned as she leaned into him. She kissed and sucked his neck before moving down to his nipples and taking them into her mouth. Her hands roamed across his sides as her tongue trailed across his slim belly. “That tickles big sis.” He giggled at the feeling.
It quickly turned into another moan as her face reached his shaft and began playing with it, it jumped at the feeling of her soft hands. She pulled the foreskin back and his toes curled as she played with the tip. She licked her lips in anticipation and gave it a few strokes before she brought her hands to his silky smooth buttcheeks and squeezed them while at the same time taking it into her mouth. Oliver bit his lip at the feeling of his dick being sucked on like a lollipop. He had no idea it would feel this good. Her tongue swirls around the cockhead, licking the sensitive underside between the foreskin and the head. The sensation made him slightly back up but then he felt a finger enter his butthole and he threw his head back, legs trembling at the feeling on both ends. Wren was eagerly sucking licking and bobbing her head back and forth, Oliver put his hands on her head to urge her to keep going. To an onlooker it would be hard to imagine this was her first time doing this. He felt something building up in his dick, like he had to pee but this was somehow different. Suddenly he remembered something from his health class.
“Big sis, it feels so good! I’m going to ejaculate!” Wren pulled her mouth off of his and gave him a smile.
“It’s called cumming Ollie, and it’s not time yet.” She said grasping the shaft and tickling his balls. “I want you to put it inside my pussy.”
“I want it too.” Oliver moaned as his sister stood up and wrapped him in her arms. Their skin felt so warm pressed against each other. Next thing they knew they were rolling around on the bed, kissing each other passionately with tongues wrestling against each other. Soon Wren was laying on her back with her legs spread and Oliver positioned right above her. His dick was rubbing against her pussy.
“I… I’m putting it in.” Oliver said. Just like that he pushed into his sister’s pussy, the folds opened up to his dick and in that moment they were no longer virgins. Wren’s hymen was torn and it did sting a bit but she was already mentally prepared for this. Her walls clenched tight on his dick but he pushed on, until he bottomed out in her. They both let out a gasp at the feeling unlike anything felt before.
“Ah, You’re inside me Ollie.” Wren whispered. “Please keep going!”
Oliver answered with a clumsy thrust making his sister gasp again. A few more thrusts later he started to get a rhythm to it. Their breaths quickened as their bodies were moving faster. Wren felt so good and tried to meet his thrusts by squeezing her pussy making it harder to pull back adding extra pleasure to Oliver. If their parents were home they would definitely hear the loud moans coming from their bedroom. The bed was squeaking with the force of each thrust. Wren was writhing on her back, trying to resist rolling her eyes as she wanted to look in her little brother’s face. Oliver’s face was red as he was panting like a dog. They were both covered in a thin layer of sweat.
“It feels so good Wren!” Oliver moaned. “AH! My penis feels so good!”
Wren smiled and wrapped her arms around the back of his neck. “My pussy feels so good to Ollie! I want to do this everyday with you!”
“Me to sis!” Suddenly his eyes widened. “Sis, I think I’m going to cum!”
“Do it Ollie, cum in me!” Wren begged.
Acknowledging her request he started thrusting rapidly and sloppily. She could feel his body start to tremble. The floodgates were at it’s limit, ready to burst.
“WREN!”
“OLLIE!”
They both screamed out as Oliver hilted himself inside her and he threw his head back, Wren’s eyes rolled back as hard as she could as her body arched forward. She felt his penis swell and pulse, shortly after she felt a warmness seep into her and that’s what it took to make her cum. Her walls contracted around him, squeezing like a vice as her juices gushed out. Despite being hilted inside Oliver instinctively thrusted forward in order to push out all his cum. His scalding hot load released for the first time inside his big sister. It was like Oliver’s entire being was being pushed inside such a small opening. The feeling was so intense and new, his senses were being overwhelmed as he scrunched up his face in pure bliss. And then it came to an end.
Drained of energy, Oliver collapsed on top of his sister. She was exhausted as well but had enough energy to lightly caress the warm and smooth body laying on her. The boy hiccupped with the afterglow settling in, nuzzling into his sister’s breasts like they were pillows.
“That was so good Ollie. I love you.” She whispered kissing his forehead.
“Mmm, love you to sis…” He mumbled before fulling falling asleep on top of her, not even pulling out. Wren smiled and stroked his soft brown hair. As she to drifted off to sleep, not even thinking about what they were going to say in the morning, she thought of one thing. That she had finally fulfilled her dream, the itch has been scratched.
And like all itches once you scratch it one time you will want to scratch it again.