18 year old Dawn was very satisfied, very satisfied indeed. She had, in the past week, jumped her hot older neighbour Eric Sherburn, and he had given her not one, not two, but three mindblowing orgasms the first time they had sex. She could never sleep with other high school boys again, if this was what she could look forward to!

But alas, the problem with living under her parents’ roof was that she couldn’t come and go as she pleased and they still insisted on knowing where she was at all times.

This made it hard for her to hang out at Eric’s place for long periods of time. Sure, 30 minutes was enough for a quickie, enough for him to plow her young pussy and rip another orgasm out of her trembling body, but it wasn’t enough for all the other things Dawn wanted to do.

Like anal orgasms, for instant. She watched porn, just like all other young people did, and had seen porn actresses squealing and screaming as their assholes spasmed on the thick cocks invading them. While she knew pussy orgasms were definitely possible, she wondered if anal orgasms were just a myth sold by porn companies to generate more sales.

Eric had told her it was possible, though he had been hesitant on fucking her ass because he thought she was ‘too young’ and ‘too unprepared’ for anal.

What kind of preparation would she need anyway? All the porn stars just shoved it in, surely it couldn’t be that hard?

She had begged and pleaded and wheedled Eric until he agreed to fuck her in the ass before she left for college in the fall. Dawn didn’t know what kind of preparation Eric wanted her to do, but they only had a little over four months to do it and she honestly couldn’t wait.

In the meantime, she would settle for a taste of his lovely big cock whenever she could manage.

A week passed quickly. Dawn started to get up earlier to pretend to walk to school when in fact, she snuck over to Eric’s house for a morning fuck. There was nothing like a good, long, hard, orgasm to wake her up each day! After a quickie in the kitchen or the living room, Eric would throw a blanket over her in the backseat and then drive her to school.

Dawn’s mom and dad, bless their souls, never noticed. They never suspected their sweet young daughter of doing such a thing with the neighbor!

Eric was also very careful to let Dawn out of his car a block away from school so she could walk the remaining distance.

Even though Dawn was already 18, they were aware that not many people would understand their sexual connection. Eric loved Dawn’s young enthusiasm, and Dawn loved the way he could fuck her through multiple orgasms.

On Friday afternoon, Eric waved at Dawn from his backyard, motioning for her to come over.

Mom had a dentist appointment so that would take forever, and her dad was still at work. The both of them wouldn’t be home until later in the evening. Dawn put on her oversized hoodie and quickly made her way to Eric’s house.

She had barely time to knock before Eric was yanking the door open and pulling her inside. His mouth was on hers immediately, kissing her passionately. Dawn kissed back, eager for another round of amazing sex.

“Wait, wait,” Eric pulled away breathlessly. He smiled down at her and pulled her towards his bedroom.

Dawn blinked in surprise at the multiple packages strewn across the floor.

“Since you’ve been wanting to try anal, I thought it would be best if I bought some tools to help train your little butthole,” Eric said, walking over to the bed. He picked up a shiny little egg shaped device and showed it to Dawn.

Dawn was touched! She wouldn’t consider herself in love with Eric, and neither would he be in love with her — they were just enthusiastic friends with benefits. So she hadn’t expected him to go all out and purchase so many items just because she wanted to try ass-fucking!

“So this is the smallest one, and the next size, and we’ve got four here, I think if you do one a week, you can get up to cock sized ones within a month. This small dildo is for your ass only … Dawn are you alright?” Eric stopped halfway through his eager introduction of all the toys, looking at Dawn with concern.

She wiped at her eyes.

“You didn’t have to go through all this trouble for me, Eric!” she said, feeling a little emotional. Eric opened his arms and enveloped her in a tight hug.

“Of course I did, Dawn. You’re a young girl who wants to experience new things! What sort of friend would I be if I didn’t do it properly?” Eric reassured her.

Dawn grinned up at him through watery eyes.

“Thank you, Eric,” she said with a big smile.

“Don’t thank me just yet, Dawn. There’s one thing I think you might not like!”

Eric picked up a big squeeze bag. It looked vaguely familiar. Dawn scrunched her nose up, wondering where she might have seen something like it before.

“It’s an enema bag,” Eric explained “Anal means fucking the shit hole. If your ass is full of shit, you betcha my cock won’t fit.”

Dawn snorted at his bad rhyming, then took the enema bag from Eric with a doubtful look.

“How do I use it?” she asked.

Eric motioned for her to follow him into the toilet. Dawn stripped off her clothes as Eric filled up the bag with warm soapy water. The bag was connected to a long tube, which had a nozzle attached. Eric pointed to the bathtub. Dawn got in and lay on her back as instructed, shivering when her bare skin came into contact with the cold porcelain. She pulled her knees up to her ears, exposing her bald pussy and asshole. Eric hooked the bag of soapy water onto the shower curtain rod, leaving the tube dangling downwards. He grabbed a bottle of lube and greased up the nozzle.

“Are you ready?” he asked.

Dawn was very nervous, but she really wanted to know what anal felt like, and if this was part of the process, then so be it!

She nodded firmly.

Eric pressed the nozzle against Dawn’s sphincter. Unlike her sopping cunt which was meant to take cock all the time, her asshole was resistant, only used to expelling things and not receiving things. Dawn had to take deep breaths and consciously unclench before the nozzle could breach her tight rosebud.

The nozzle was very slender and with the lube, it didn’t hurt. It felt foreign, but that was just about it.

Dawn looked at Eric expectantly.

Eric stood up and unclamped the tube.

Immediately, Dawn felt a gush of warm liquid pour into her waiting asshole! Her mouth fell open in surprise as the warm soapy water obeyed the laws of physics and flowed downwards. Without anywhere else to go, it went directly into Dawn’s tight hole.

“Oh, oh oh!” Dawn gasped as her rectal cavity was filled with liquid “Oooh aaaaah!” she moaned. The feeling was incredibly pleasant. The warmth of the water contrasted the cold of the tub on Dawn’s skin. She felt her nipples harden immediately and her cunt become even wetter.

“You like that!” Eric exclaimed, surprised but pleased.

“It feels good,” Dawn said breathlessly, her eyes watching the water levels in the bag slowly decrease. At the halfway mark, her bowels started to feel very full and she started to squirm, but Eric leaned over the side of the tub and pinched her nipples.

“Hold still,” he scolded lightly, “It won’t be effective if you just do half a bag. Just hang on a little longer, alright?”

Dawn moaned. The pleasant pressure was starting to feel a little unpleasant. It was pressing against all corners of her insides, making her feel as if she was a balloon, swelling up and about to pop. Eric slid one hand down to her bald cunt and pushed two of his fingers inside, curling them upwards against the front of Dawn’s pussy. She moaned, mind temporarily taken off the uncomfortable liquid filling her bowels.

“That’s it, you’re doing so well,” Eric praised her, gently fingering her young cunt while her ass was filled with water.

“How much more?” Dawn panted, wanting, but also not daring to look.

“A little more,” Eric reassured her. Dawn bit her lip. She thought of the porn actresses who took cock in their assholes as easily as breathing. She wanted to know what that was like. She had to know what that was like! And to do that, she would have to endure this enema!

Dawn moaned again. Eric pinched her clit lightly, making her jump and clench around the nozzle.

“Just a little, little bit more aaaaand, we’re done!” Eric proclaimed. He smiled down at Dawn. Eric reached to the side for a little silicone plug and lubed it up. With one smooth move, he pulled the nozzle from Dawn’s shithole, and then slipped the silicone plug in. Dawn gasped, her sphincter instinctively clenching around the plug. It was only a finger thick, with a flared base and narrow neck that prevented it from slipping out. The pressure from inside her hole had it jammed uncomfortable at Dawn’s anal ring, unable to be expelled or pushed inside.

Eric picked up his phone and set an alarm for 20 minutes.

“20 minutes, alright? We give it time to soften up all the nasty shit in your ass so that it’s clean for fucking later.” Eric reached down to stroke Dawn’s soft blonde hair, then left her to squirm while he washed and put away the enema bag.

Dawn had never felt so full in her life. Her flat stomach was bulging with the amount of liquid Eric had poured inside her! It looked as if she had somehow gotten pregnant. Dawn kept her hands on her knees and tried to concentrate on something other than the unpleasant pressure in her bowels. She recited all her Spanish conjugations and then mentally went through some trigonometry before she heard Eric’s phone chime loudly.

Eric appeared at the bathroom door.

“All fours,” he instructed, turning on the shower so that there would be running water “Since it’s your first time, I don’t think you’ll be able to aim, so you can shit in the tub, When you’re more used to it, you can use the toilet.”

Dawn nodded to indicate that she heard him.

Eric patted her back comfortingly, then put his hand on the base of the silicone plug.

“On three,” Eric said “One -, two-”

He yanked hard before he said three! Dawn’s eyes flew wide open as her anal ring was pulled sharply outwards. The warm soapy contents of Dawn’s bowels immediately came spurting out, spraying all over the white sides of the tub.

“Unngh! Annngh!” Dawn moaned as the shit in her rectum came blasting out in a dirty yellow-brown mess! The shower water beat down on her, washing all the disgusting filth down the drain. Dawn’s hole clenched and twitched. Every single squeeze of her hole seemed to blast out more excrement.

Dawn felt her face burn in embarrassment, having shit herself in front of a man she respected and liked.

Eric didn’t seem to be embarrassed at all. He picked up the bidet and started to spray down all the crap that was still on the sides of the tub, directing the flow of shit to the drainage pipe.

“You doing alright?” Eric asked. Dawn nodded, feeling shy.

Eric rinsed her off with the bidet, then bade her to take a quick shower.

Dawn stood up under the spray of hot water. Her face was bright red from what she could see in the mirror. She had never thought she would ever get an enema, but here she was. She bet that none of the other girls in her school had ever done something like this!

She shook her head. It was over, and for her to achieve her anal goals, this was only a small step. Dawn soaped herself up quickly with Eric’s body wash, then rinsed herself off, careful to wash between her legs and around her asshole.

When she got out of the tub, there was a fluffy towel waiting. Dawn dried herself off and then stepped into the bedroom completely nude.

Eric had cleared up the floor while she was in the shower. He left only the smallest plug and the lube on the bed.

“Come on, face down over the pillow, legs apart.”

Dawn obeyed, putting the pillow under her hips and spreading her legs apart. Eric kneaded her firm bottom for a moment, savouring the sensation of young nubile flesh under his hands, bent his head to press a kiss to the bottom of her spine. He kissed each of her buttcheeks, then licked at her butthole tentatively.

Dawn gasped. The wet rasp of tongue on her anal ring was unexpectedly pleasant! She hadn’t considered the fact that her sphincter had many nerve endings and would be so sensitive to pleasure. Dawn couldn’t help but moan as Eric’s mouth plundered her asshole, kissing it and tonguing it so deeply that it felt like a sloppy make out session under the bleachers with one of those overeager football players. Only this time, unlike those sloppy make out sessions, this one was igniting a fire in Dawn’s belly. Her cunt juices gushed, flowing out from her young pussy like a small stream.

Getting her asshole french kissed was a whole new experience and Dawn loved it. She moaned and squirmed and tried her best to stay still while Eric tongue fucked her shithole.

“Oooh ohh, ahhhh!” she cried out, trembling with pleasure.

Eric pulled away for a moment. He grabbed her hands and placed them on her buttcheeks. Dawn immediately grabbed at her flesh and spread herself so that he could have better access to her brownhole.

“I’m going to enjoy fucking this when the time comes,” Eric said. He took the lube and smeared it generously all over his fingers and Dawn’s asshole. Then, without further warning, he pushed his forefinger into Dawn’s twitching asshole.

“Eeeeehhhh!” Dawn squealed as the finger went in all the way. Her hole had been loosened by the enema and the vigorous tongue fucking. With such a large amount of lube, it didn’t stand a chance against a solitary finger.

Eric moved his hand, slowly at first, then faster and faster, pumping that finger of his in and out of Dawn’s tight virgin asshole.

Then on one of the outstrokes, he put two fingers together and jammed those all the way into Dawn’s hole.

“Oooh ahhh!” Dawn whimpered! One finger felt like a light stretch, only a little bit of discomfort. But somehow, two fingers felt like her hole was being torn apart!

“Do you see now, why I said we couldn’t do anal immediately?” Eric asked patiently. He thrust his fingers in and out of Dawn’s eager hole.

“Yes, I understand now,” Dawn sobbed, biting her lip. While she loved having her pussy stretched and split wide open on a large cock, having her asshole stretched and split wide open felt quite different.

Eric took pity on her and didn’t add a third finger. Instead, he just slid the anal plug in all the way and used a damp washcloth to wipe away the excess lube all over Dawn’s buttcheeks.

The anal plug was slightly smaller than the circumference of Eric’s fingers. Dawn’s hole clenched weakly around it once, twice, then settled around the narrow neck, keeping it firmly inside.

Eric patted Dawn’s shapely buttocks, then rolled her over.

“You okay?” he asked. Dawn nodded through teary eyes, breathing through the strange sting of having her anal passage plugged up. While it was uncomfortable, she had asked for this. She was the one who requested that they work up to anal so she had to stick with her guns!

“Fuck my pussy now?” Dawn whined hopefully.

Eric laughed and pulled off his boxers to reveal his lovely hard cock.

“It would be my pleasure!”

All the discomfort hadn’t stopped Dawn from getting really wet. Eric didn’t have to lube up at all, just line up and thrust himself all the way into Dawn’s eager cunt.

However, this time was slightly different. Dawn’s eyes flew wide open when Eric began to pound her pussy in earnest. She could feel the anal plug in her through her pussy walls! Eric’s thick rod could barely fit in Dawn’s young and tight pussy. It always stretched her to her limits. Now, each thrust rubbed her pussy walls against the plug inside her asshole. The sensitive flesh between pussy and asshole was pressed and rubbed over that metal toy repeatedly, lighting up the nerves there with equal parts pain and pleasure.

Dawn whimpered, keeping her legs high up so that Eric would have a better angle.

“Oh the plug is making you so much tighter,” Eric growled, enjoying the increased tightness of Dawn’s cunt. Dawn moaned.

“Ohhh ohh ohh, your cock feels bigger too!” She exclaimed “Oh oh oh I’m cumming!”

The sensations proved too much for Dawn’s young pussy to bear, sending her into a powerful orgasm that wracked her whole body and had her holes spasming on the intruders penetrating them.

Eric obligingly fucked Dawn through the aftershocks of her orgasm, then growled deep and animalistic before unloading his balls into her sopping hole.

Dawn wore the plugs to school. She started off with the smallest one, lubing it up well before slipping it into her hole and then pulling her panties up over it. Eric had been delighted when he shoved his cock into her pussy that morning and found it tighter than before due to the presence.

The first day had been hell. Dawn hadn’t considered the fact that having something in her for so long would chafe something fierce so she didn’t bring extra lube, and had ended up with pink puffy asshole, rubbed almost raw by the metal plug. Eric took pity on her and soothed her hot hole with his tongue. The next day, Dawn put lube into an unmarked travel-sized squeeze bottle that she usually used for her toner, then reapplied the lube every two periods. It was significantly more comfortable than the first day, even though her hole was still sore when she got home. When she was at home, she would leave the plug out for a few hours so that her hole had a chance to rest. Then, she would finger her hole a little and plug herself back up.

Dawn also took to sleeping with the plug in so that she could train her asshole faster.

At the end of the first week, she swapped her size 2 anal plug for a size 4 and slipped it into her eager asshole at Eric’s house.

They celebrated her graduation to a bigger plug with a passionate 69 session followed by a good, long, hard, pussy pounding.

As Eric had predicted, it took Dawn about a month to train her asshole to accept regular cock-sized dildos. Like previous times, Dawn snuck out to Eric’s house and then pulled out her anal plug, fully intending on getting a bigger size. Only then did she realize that there was no bigger size. She frowned at the drawer full of toys.

“Looking for this?” Eric asked. Dawn’s head snapped over to look at him.

It was a 5 inch dildo that was only an inch thick. It was smaller than the regular sizes that Eric had promised, but Dawn wasn’t complaining. She wanted to try fitting that into her asshole!

Without wasting any time, she went to the bathroom and prepared her enema.

The 20 minute wait was torturous. She was filled with anticipation and nervousness. Would a dildo feel any different than the plugs she wore to school on a daily basis? The question plagued her as she expelled the contents of her bowels and dried her cute derriere before strutting out into the bedroom.

As ever, the pillow was ready for her. Dawn assumed the position quickly, lying down with her hips on top of the soft pillow, pushing her ass upwards for Eric to access.

“Here goes nothing!” Eric said, pressing the lubed up toy against Dawn’s asshole.

The little hole yielded easily, having gotten used to opening up for intruders over the course of four weeks. The only difference now was that the dildo was a uniform thickness from base to tip. This meant that Dawn’s anal ring had no time to relax at all! It was stretched out, and then kept that way.

“Oh oh oh!” Dawn whispered as the dildo slid in and out of her tight bottom. It wasn’t uncomfortable, or unpleasant, just different. But it was a kind of different that was rapidly becoming good.