Anal Training Sex Story 2024 – Y2-Stories

A simple story. A girl asks her older sister to help her prepare her ass for her first anal fuck.

“K-Katy? Can I ask you something?”

Katy looked up from her physics homework. Her little sister May came closer, all nervous, looking down and biting her lips.

“Sure, little trouble! What’s up?”

“I… I lost a bet. You know…” May stuttered.

Katy grinned.

“Again? One day you’re going to end up in big trouble, little trouble! Just remember when they made you stand on the roof of the school wearing only your panties and screaming “Look at me, everybody!…” Whatever. What’s this time?”

May took a deep breath.

“Well… Do you know three boys from my class? Ryan, Justin and Jake?”

Katy nodded. She knew them well enough. They were tall, actually nice, very popular, and always surrounded by girls who swooned over them. And, like almost everyone at twelve – including May – they were already obsessed with their first thoughts of sex, but too scared to start yet.

“Yep. They were the ones who made you strip down to your panties, weren’t they?”

May nodded, shivering.

Katy grinned again.

“What have you lost this time? First blowjob? Striptease dance in class?”

May shook her head, blushing. She seemed unable to speak.

“What then? Uh… you’re really shaking, little sis! Calm down!”

Katy hugged her sister, and May clung to her, trembling. Then she whispered in Katy’s ear:

“I have… I have t-to… f-fuck them! T-Tomorrow! All th-three!..”

Katy frowned and patted May’s shoulders.

“Ouch. You’re not wasting your time, kiddo, are you? Isn’t it too fast?”

“M-maybe…” May stuck her nose into Katy’s chest.

“Aren’t you still a virgin? Or did I miss that moment?”

“I am…” May whispered. “That’s why I need your help.”

Katy frowned again. “I could come with you and tell them it’s too soon for you. I’m sure they’d listen to me.”

“B-but…” May looked up at Katy, still biting her lip, but with a mischievous twinkle in her eyes. “I… I don’t want to back out! I really want to try!”

Katy laughed and hugged her little sister tighter.

“Such a naughty girl you are, little trouble! So, let me guess, you want me to…”

May nodded.

“…deflower you and teach you a few women’s tricks?”

“W-what?” May looked surprised. “Oh… not that I w-wouldn’t like to… But, really… they’re only d-doing my ass tomorrow.”

“Oh.” It was Katy’s turn to look surprised. She had never yet tried anal herself. “So what exactly do you need?”

“T-teach me how to relax my ass… when a thing goes inside,” May whispered. “A big thing, probably. Th-three big things…”

Katy laughed, rather nervous and excited herself.

“Okay, kiddo. Let’s do it. Get undressed while I prepare…”

“W-what?! Right now?”

“Why wait, little trouble? The parents will only be home in the evening. We have three safe hours ahead of us, I bet that would be enough!”

“Three hours?!” May blushed deeply. “R-really?”

Katy nodded confidently. “Some time to prepare, and the rest to fuck your little ass to some nice orgasms! Come on, get undressed!”

Nervously, as if preparing to jump into an icy pool of water, May took off her robe and pulled down her panties, revealing a slender naked body that only suggested her future female shapes. Kate dived into the secret depths of her desk box and returned with the bottle of lube and a thick, long, rubbed and elastic two-sided dildo that looked more like a fat snake.

May widened her eyes.

“That b-big! I did not know you had such things! Are you going to t-to… to stick it… it… all inside…”

Katy laughed and tried the dildo on her sister’s body. It reached from her hips to almost her throat.

“It’s my new one! Don’t tell the parents! And no, of course you won’t fit in it whole. Just…” she squinted slyly, “about one-third, maybe…”

“Ouch!”

May trembled and blushed, and it wasn’t just out of fear.

Katy put the dildo down and hugged her sister again.

“Let it wait for its turn. Come on, relax. We’re taking it slow…”

With a moment’s thought she undressed, too. Of course, the sisters hugged a lot (when they weren’t fighting) and practiced kissing each other, but this was the first time they got naked together, not just for the common bath, but for something more intimate.

Kate hugged May and held her little sister close, skin to skin. Then they began to kiss. Nervously at first, then passionately, then deeper and stronger. Their nipples brushed against each other and became erect, rubbing and pinching. May moaned softly into Katy’s mouth and involuntarily ran her small palms around Kate’s teenage curves, sliding along her narrow waist and caressing her bottom. Katy squeezed May’s butt as well. They both felt the arousal rise in them – a familiar thing for Katy and a new one for May. Katy slid her fingers between May’s legs and touched her pussy, which was already wet. She began to stroke it lightly, and May began to moan louder, clinging tighter to Katy and pressing her own pelvis harder against Kate’s fingers.

“Lie on your back…” Katy whispered. “I’m going to show you some tricks…”

May obeyed and lay down on her sister’s bed, spreading her legs, panting and red with excitement and embarrassment. Katy lay down next to her and continued to tease her pussy until it was completely wet, then parted May’s labia.

“Oh, sis, what a beautiful thing you have here!”

May’s tiny clit was fully erect and red. Katy leaned down and began to kiss it, biting it with her lips and teasing it with the tip of her tongue. Then she added two fingers, rubbing the opening of May’s vagina and gently pushing deeper until she felt her sister’s hymen. Katy licked May’s clit faster and faster as she stroked her hymen from the inside with two fingers. Eventually May couldn’t resist anymore. She threw back her head, closed her eyes and moaned loudly, twitching and arching sharply, and suddenly Katy felt a surge of hot fluid under her fingers.

“Ohhh, sis, so you are a squirter!”

And with a sudden impulse, Katy pushed her fingers all the way into May’s pussy, tearing her hymen. May screamed briefly and opened her eyes wide in surprise. Katy smiled wickedly, moved her face closer to May’s and kissed her. Then she pulled out her fingers, smeared with a bit of blood, showed them to May, and slowly and teasingly licked them clean.

“Ouch! Katy… what did you…”

“I just thought you wouldn’t wait long to start fucking all the holes, so I prepared you for that too.” Katy giggled. “Don’t thank me!”

May blinked nervously and blushed, but made no further protest. Katy lay down next to her, nuzzling and kissing her.

“Did you like your first orgasm, little one?”

May nodded, shyly hiding her burning face in Katy’s neck.

“Th-that was cool…” she admitted. “But… w-will I orgasm tomorrow too? With boys in my ass?”

Katy laughed and kissed May again, running her hands down her sister’s thin young body.

“Of course you will, after today’s training! And for now…” Katy lay on her back and spread her legs, “warm me up too…”

And May leaned against her sister’s crotch and did her best to repeat what Katy had just done to her. Soon Katy was moaning and squirming too, grabbing May’s hair with both hands and trying just not to push her little sister’s face too deep between her legs. When May pushed her fingers deep into Katy’s hole, she shivered all over and let out a loud moan.

“Ohhh… sis, sis… don’t stop…”

May didn’t stop. Katy squeezed her sister’s body with her legs and soon came as well. She sighed deeply and stroked May’s hair. Then she rolled onto her side and hugged her sister tightly. The girls rested for another five minutes, cuddling and whispering something silly into each other’s ears.

“You’re so good at this, little trouble…” Katy kissed May gently. “And you will be so much better… It’s a shame we didn’t start earlier!”

May giggled happily and kissed Katy back.

“Then… shall we continue?” she asked shyly.

Katy winked happily and sat up.

“We do! To the bathroom!”

“To the bathroom?..”

“Yes, sis. Let’s get you deep clean.”

In the bathtub, Katy showed May how to remove the shower head and teased her sister’s anus with the stream of warm water from the hose.

“Now relax…”

And she pushed the hose gently but steadily into May’s sphincter.

“Ow!” May twitched from the scratching pain in her anus.

“Hush, pumpkin…” Katy cupped her shoulder with one hand and kissed her back. “Relax. Relax… It will feel good soon…”

And she pushed the hose a little deeper. Sprinkles of warm water dripped from May’s anus around the hose.

“Relax…”

May jerked and squealed again.

“Ouch! Katy!”

She felt unusual warmth and pressure in her rectum. Her belly began to slowly bulge out. May panicked, imagining the tube stretching her intestines inside and going deeper into her body, but Katy held the tube tightly near the outlet. The warm water poured straight into May’s rectum, filling her colon. May took a deep breath and relaxed her abdomen. The unpleasant scratching sensation disappeared, leaving only an unfamiliar fullness. Katy kissed May’s back again.

“Relax, pumpkin…”

“Katy… Ow… I’m so full… I can’t hold any more…”

“You can, pumpkin!” Katy laughed softly, stroking May’s round belly. “You’re a real pumpkin now! Just a few more moments…”

“Katy! I can’t!..”

“Okay. Now…”

Katy removed the tube from May’s anus. Immediately, brownish water rushed out, carrying bits of feces and splashing the girls’ feet.

“Eek!” May shuddered with embarrassment.

“It’s okay. Push. Let all the water out of you…”

Katy stroked her sister’s body and washed her clean while May tensed up and pushed the water out. Then Katy set the shower hose aside and began to massage May’s stomach to ease her discomfort. Finally, she kissed May again and whispered:

“Now the second round. Let’s get you completely clean inside…”

And she pushed the tube back into May’s anus. This time it went smoothly. May felt no pain, just the pleasant warmth and stretching. She held her bulging belly with both hands and laughed as she felt it grow.

“Katy… I think I’m going to explode!..”

Katy laughed too and kissed her sister’s back again.

“No, pumpkin, you won’t! I promise!”

May pushed and the water flowed out, clean this time.

“Perfect, sis!”

Katy waited for the jet of water to subside, then kissed May all the way to her anus, sticking her tongue in and tickling May’s sphincter. May squealed happily and twitched. Katy continued to lick her sister’s anus, pushing her tongue deeper, then pulling it out, then putting it back in, playing with May’s asshole until May was moaning and wriggling again.

“You taste so good, sis… I love you…”

Katy turned May over and kissed her on the lips. May responded reluctantly, but there was no bad taste in Katy’s mouth.

“Now sis, do the same to me.”

Katy stood on her four and turned her ass towards May.

“To you? Why?”

“I’ve never had anal either,” Katy winked. “Today will be the first time for both of us, little trouble!”

May stared at Katy’s anus – pink, clean, and cute. A small, wrinkled sphincter glistened with moisture. Hesitantly, May took the shower hose and pushed it into her sister’s ass. Katy moaned softly and spread her knees wider.

“Further… Deeper… Ohh, pumpkin… Yesss… That’s great…”

May pumped water into her sister’s ass as she watched her belly bulge. Katy was older and bigger and could hold more water, but soon she also was moaning louder and biting her lips.

“Ohh… May… I’m close…”

May immediately pulled out the hose and let Katy empty herself. Just as her sister had done before, May cleaned her with the water jet, then pushed it back in and filled her sister again, and let her push out the clean water. When they were done, Katy turned and hugged May and kissed her.

“Wonderful, pumpkin…”

The girls washed and dried each other thoroughly. Warm, flushed and excited, they ran back to the bed.

“Now for the main event!” Katy laughed. “Stand on your four and spread your knees. Wider… Yes, that will do!”

May trembled with excitement and fear as she watched Katy lubricate the end of the dildo.

“Katy… It’s so thick… How will it fit?”

“Easy, little trouble! You have practiced well today! Relax and it will slide into you without any problems.” Katy slapped her sister’s ass playfully. May twitched.

“Ouch!”

“Get used to it, sis. Men like to slap girls’ butts!”

And Katy pressed the tip of the dildo against May’s anus and slowly pushed it in.

“Ow!”

“It’s okay, sis… It’s okay… Relax…”

May relaxed and listened to the unusual stretching sensation at her anus. It wasn’t painful, but it stretched so much… May relaxed even more and suddenly the thing slipped in. May gasped. It was inside… In her ass!.. Katy grabbed May’s waist with one hand, holding the dildo with the other, and began to push it deeper and deeper. May managed about three inches before the dildo touched the soft obstacle inside. She couldn’t hold back a soft moan. It was… it was pleasurable!

“Katy… I’m so full… I’m going to poo…”

“There’s no poop, sis!” Katy laughed. “Just that nice thick long thing up your ass! Relax and get used to it…”

Katy waited a minute, then moved the dildo back and forth a bit. May moaned again as she felt the obstruction give way and stretch even more. She felt a slight tickle in her pussy.

“Mmm… Katy, do it more…”

“Wait a bit, I have an even better idea!”

And Katy lubricated the other end of the dildo, bent it and pushed the tip into May’s pussy. The hole was almost as tight as the anus, and now it was squeezed by the dildo in the ass, but Katy pushed and managed to get the dildo into May’s pussy as well. May gasped loudly. She felt stretched to the limit, almost torn apart, but there was no pain, just increasing arousal and tickling pleasure. Katy pushed deeper and May’s little pussy took a full five inches into it! She felt that there was simply no room left inside for anything else. Katy chuckled happily and began to move the dildo back and forth, in May’s ass and pussy at the same time, slowly and carefully at first, then faster and harder, using both hands to pump the dual-edged curved dildo into her little sister’s holes.

May closed her eyes and grabbed the sheets with both wrists. Katy fucked her fast and steady. May felt waves of pleasurable sensations rise from somewhere in her belly to her whole body, washing everything else away. It got hotter and brighter with each thrust and May felt something strange coming from deep inside her, so strong and pleasant… May shook, curled her toes and screamed loudly, feeling something explode inside her and spread throughout her body… And as soon as Katy pulled the dildo sharply out of her pussy, May squirted profusely, gasping and squealing.

Katy continued to pump the dildo hard and fast into May’s ass, forcing her sister to wriggle, scream and moan, arching and curling, and squirting in orgasm after orgasm, until finally she collapsed limply on the wet bed with her ass up, exhausted, breathing heavily and barely moving. Katy pulled the dildo out of her ass and leaned over May’s back, hugging her sister and gently biting her neck, shoulders and earlobes, purring with excitement.

“So how was it, little one?”

“Goooood…” May murmured through her teeth. “Sooo gooood… Thank you… Will it be so good tomorrow when they fuck me?”

Katy giggled and kissed May again.

“It will be even better, believe me! Just wash your ass before you give yourself to them and lubricate their dicks. They would love it!”

“How do you know? Have you ever fucked guys?” May opened one eye and looked at Katy curiously.

Katy laughed again.

“Little trouble! I’m fourteen already! Of course I’ve fucked guys! It’s the best thing in the world! Only… I only gave them my mouth and my pussy so far. Help me train my ass too!”

And Kate stood on her four and eagerly pointed her ass up. May took the dildo and lubricated its tips. Slowly and carefully she pushed it into Katy’s anus.

“Further… Keep going… Pumpkin… Yes! Ow! Deeper, push it deeper!”

Katy’s ass took six inches of the dildo, and seven more into her pussy before she moaned with pleasure as the dildo tips touched her cervix and sigmoid simultaneously. It took almost the full length of the dildo. May pumped it back and forth, learning to control the force and speed of penetration, listening to Katy’s instructions and comments, which quickly turned into pure gasps and increasingly loud moans. Within minutes, Katy reached her first anal orgasm and screamed with pleasure. May, remembering how Katy had done her, did not stop, but continued to pump her sister’s holes as hard and fast as she could. Kate’s moans turned to growls, she tensed in a full body spasm, only whispering hoarsely: “More… more…” – between her grunts and screams.

May’s hands grew tired before Katy finally collapsed on the bed, convulsing and whimpering. Then May pulled the dildo out of her sister, cuddled up to her and started kissing her sweaty body all over. Katy barely opened her eyes and turned her head to face May.

“Sis… Little trouble…” she whispered hoarsely, smiling blissfully. “You’re the best… You are the real gem… No one has ever fucked me so well…” She kissed May’s lips. “I love you…”

“I love you too!” May eagerly returned the deep kiss.

Katy hugged May and held her tighter. Then they fell asleep almost immediately, exhausted. May lay on her sister’s chest, stroking Katy’s pubis with one hand and playing with her nipples with the other.

They slept a little and awoke from the cold of the wet sheets just in time to clean up the mess, hide the dildo and change the sheets before their parents returned.

“Why are they so wet?” May asked. “Did I pee on the sheets? So embarrassing…” She blushed.

“No, pumpkin!” Kate laughed and hugged her. “It’s called squirting, not all women can do it. I can’t, for example. I’m so envious of you! Men love it, it shows them that your orgasm is not fake, but the real thing.”

“Fake orgasm? What’s that like?”

“You don’t need to know!” Kate laughed again. “You are so orgasmic that you are exploding like fireworks! You’ll always have lots of real orgasms!”

***

Later that night, when the sisters were already in their beds, May crawled over to Kate and pulled off her nightgown. She was already naked herself.

“Kate! I can’t sleep! I want to do it again! Let’s do it again!”

Her sister giggled softly.

“Of course, little trouble! Anytime, as much as you want! Just be quiet so our parents don’t hear…”

And the sisters entwined themselves in a tight embrace, rubbing each other’s clit and labia fiercely, their mouths sealed with a deep mutual kiss to muffle their moans.

The next day the boys were just stunned. They expected May to hide from them, maybe even fight back, but instead she willingly took off her panties, grabbed the bottle of lube and laughed: “Your dicks, boys! Who’s first?”

They did not need a second invitation and each of them came in May’s ass at least twice. But that’s a story for another time.