Starting My Anal Training to Accommodate My Neighbor’s Massive Cock

While I loved having my pussy stretched and split wide open on his large cock, having my asshole stretched and split wide open felt different. Marius slipped the metal plug in, my sphincter instinctively clenching around the narrow neck, keeping it firmly inside.

My eighteen-year-old self was delighted. In the past week, I had jumped my hot older neighbor, Marius, and he had given me three mindblowing orgasms.

But the problem I was facing, while living under my parent’s roof, was that I couldn’t come and go as I pleased and they insisted on knowing where I was at all times. Even though thirty minutes was enough for Marius to plow my young pussy and rip a couple of orgasms out of my trembling body, it wasn’t enough for all the other things I wanted to do.

Like anal orgasms, for instance. I watched porn, just like all people my age do, and had seen porn actresses squealing and screaming as their assholes spasmed on the thick cocks invading them. While I knew they might be faking it, I couldn’t stop thinking about the sensation and how it would feel having Marius’s cock in my tight ass, and maybe, just maybe, I could get an anal orgasm, just like those girls did.

Marius had told me it was possible, though he had been hesitant about fucking my ass because he thought I was ‘too unprepared’ for anal. I had begged Marius until he finally agreed to do it, but not without preparation. What kind of preparation would I need anyway? All the porn stars just shoved it in, surely it couldn’t be that hard…

On Friday afternoon, Marius waved at me from his backyard, motioning for me to come over. Mom had a doctor’s appointment, and Dad was still at work. They wouldn’t get back home until later in the evening so I put on an oversized T-shirt and quickly made my way to Marius’s house.

I barely had time to knock before Marius yanked the door open and pulled me inside. His lips were on mine immediately, kissing me passionately. I kissed him back, eager for another round of amazing sex.

“Wait, wait, I have a surprise for you,” Marius said after pulling away.

He smiled down at me and pulled me towards his bedroom. I blinked in surprise at the multiple packages laid across the bed.

“Since you’ve been wanting to try anal, I thought it would be best if I bought some toys to help train your little asshole,” he said, walking over to the bed.

He opened the first box, picked up a shiny little egg-shaped metal device, and showed it to me. I was touched! I hadn’t expected him to go all out and purchase so many things just because I wanted to try ass-fucking!

“You didn’t have to go through all this trouble for me, Marius,” I said, feeling a little emotional.

Marius opened his arms and enveloped me in a tight hug.

“Of course, Anna. You’re a young girl who wants to experience new things! What sort of friend would I be if I didn’t help you?” he reassured me.

“Thank you, Marius,” I said with a big smile.

“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,” he stopped halfway through his eager introduction of all the toys and just looked at me.

“How do I use it?” I asked enthusiastically.

Marius laughed and motioned me to get undressed. I stripped off my clothes and then Marius pointed to the bed. I lay on my back as instructed and he pulled my knees up to my ears, exposing my bald pussy and asshole. He reached for a bottle of lube and started greasing the smallest toy.

“Are you ready?” he asked.

I was very nervous but really wanted to know what anal felt like so I nodded firmly. Marius kneaded my firm ass cheeks for a moment before he started licking my asshole tentatively.

His wet tongue on my anal ring felt unexpectedly pleasant. I hadn’t considered the fact that my sphincter had many nerve endings and would be so sensitive to pleasure. I couldn’t help but moan as his mouth plundered my asshole, kissing it and tonguing it so deeply that it felt like a sloppy make-out session. Only unlike a sloppy make-out session, this was igniting a fire in me. My pussy juices gushed, flowing out from my hole like a small stream.

Getting my asshole french kissed was a whole new experience and I loved it. I moaned and squirmed and tried my best to stay still while Marius tongue-fucked me.

“Oooh, ooh, ahh!” I cried out, trembling with pleasure.

Marius pulled away for a moment, grabbed my hands, and placed them on my ass cheeks. I immediately spread myself so that he could have even better access to my brown hole.

“I’m going to enjoy fucking this tight hole when the time comes,” Marius said.

He took the lube and smeared it generously all over his fingers and my asshole. Then, without further warning, he pushed his forefinger into my twitching asshole.

“Mmmm,” I moaned as his finger went in all the way,

Marius moved his hand, slowly at first, then faster and faster, pumping his finger in and out of my tight, virgin asshole. Then on one of the outstrokes, he put two fingers together and jammed them in.

“Oooh!” I whimpered.

One finger felt like a light stretch, only a little bit of discomfort, but somehow, two fingers now felt like my hole was being torn apart.

“Do you see why I said we couldn’t do anal immediately?” he asked patiently, thrusting his fingers in and out of my stretched hole.

“I do now,” I sobbed, biting my lip.

While I loved having my pussy stretched and split wide open on his large cock, having my asshole stretched and split wide open felt different. Marius took pity on me and didn’t add a third finger. Instead, with one smooth move, he slipped the metal plug in, my sphincter instinctively clenching around the narrow neck, keeping it firmly inside.

“Oh, oh oh!” I gasped and moaned as my rectal cavity was filled.

The feeling was incredibly pleasant and my nipples hardened immediately while my cunt become even wetter.

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

I nodded through teary eyes, breathing through the strange sting of having my anal passage plugged up. While it was uncomfortable, I was the one who requested that we work up to anal so I had to take it like a big girl!

“It feels good,” I said breathlessly, and he leaned over to pinch my nipples.

I moaned again when he slid one hand down to my bald cunt and pushed two of his fingers inside, curling them upwards against the front. I bit my lip, thinking of the porn stars who took cock in their assholes as easily as breathing. I wanted to know what that was like. I moaned again, louder, when Marius pinched my clit lightly, making me jump and clench my sphincter around the plug.

Marius patted my ass cheeks and I let my legs fall back on the bed.

“Fuck my pussy now?” I asked, hopefully.

Marius laughed and pulled off his boxers, revealing his lovely hard cock.

“I thought you’d never ask!”

All the discomfort in my ass hadn’t stopped me from getting really wet so Marius didn’t have to lube up at all, just line up his beautiful cock with my cunt and thrust himself all the way into my eager hole.

However, this time it felt slightly different. My eyes flew wide open when he began to pound my pussy. I could feel the anal plug in me, through my pussy walls. Marius’s thick cock could barely fit in my young and tight pussy, stretching me to my limits. Each thrust rubbed my pussy walls against the plug inside my ass, the sensitive membrane between my pussy and asshole was pressed and rubbed over that metal toy repeatedly, lighting up my nerves.

I whimpered, keeping my legs high up in the air so that Marius could hit me at the perfect angle.

“Oh, fuck, the plug is making you so much tighter,” he growled.

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

The sensations in my cunt and ass sent me into a powerful orgasm that wracked my whole body and had my holes clenching and spasming around the intruders penetrating them.

When my involuntary spasms slowed and stopped, Marius was still deep in my cunt, fucking me through the aftershock of my orgasm. He gently pulled out and ran his cock head over my clit and I shivered as my body responded to his touch.

“You’re really amazing,” Marius said and trailed his hands over my smooth belly and put his cock back in my pleasure hole again.

“Fill me with your cum,” I said keeping eye contact with him.

Marius smiled, grabbed my hips, and pulled me onto his cock. He then took a deep growl and blasted my sopping hole with his cum. Rope after rope of his seed coated the depths of my hole and I just stood there, playing with a strand of hair, waiting for him to finish cumming.

“That was incredible,” I said, stretching my legs and arms out.

After that day, I started wearing anal plugs wherever I went, even at school. I would lube it up well before slipping it into my hole and then pulling my panties up over it.

The first day had been hell. I hadn’t considered the fact that having something in me for so long would need extra lubrication and had ended up with a pink, puffy asshole, rubbed almost raw by the metal plug. That evening, Marius soothed my hot hole with his tongue.

The next day, I put lube into a travel-sized squeeze bottle and reapplied lube every two hours. It was significantly more comfortable than the first day, even though my hole was still sore when I got home. When I was at home, I would leave the plug out for a few hours so that my hole had a chance to rest, then, I would finger my hole a little and plug it back up.

I also decided to start sleeping with the buttplug in so that I could train my asshole faster and by the end of the first week, I was already able to slip the largest plug into my eager asshole.

Marius and I were at his house, after school, when I pulled out my plug, looking on getting a bigger size. After I realized there was no other size to go up, I frowned at the box full of toys.

“Looking for this?” Marius asked.

It was a cute pink dildo that resembled a natural cock. It was smaller than Marius’s cock, but I wasn’t complaining. I just smiled, filled with anticipation and nervousness, wanting to try fitting that into my asshole. Would a dildo feel any different than the plugs I wore to school daily?

Marius put a pillow on the bed, and I quickly assumed the position, lying down with my hips on top of the pillow, pushing my ass upward for easy access.

“Here goes nothing!” Marius said, pressing the lubed-up toy against my asshole.

My little hole yielded easily, having gotten used to opening up for intruders over the last weeks. The only difference now was that the dildo was a uniform thickness from base to tip and this meant that my anal ring had no time to relax at all, it would be stretched out and then kept that way.

“Oh! Oh! Oh!” I whimpered as the dildo slid in and out of my tight ass.

It wasn’t uncomfortable, or unpleasant, it just felt different. But it was rapidly becoming good and soon I started moaning as he fucked my ass with the dildo.

“Oh it feels… it feels good!” I panted.

Marius chuckled, then pushed the dildo all the way in, keeping it pressed inside with one hand, while the other fumbled with some sort of leather harness that not only held the anal intruder in place, but it also allowed access to my pussy.

I was flipped over, and Marius pushed my legs wide apart to enjoy the look of my bald cunt. I gasped when he pushed my legs up. The dildo was longer than the plugs and I could feel every inch of it rubbing against my anal walls.

“Fuck! You’re so tight…” Marius growled as he shoved his cock balls deep into my young hole and I squealed with surprise and pleasure.

He panted, my juices letting out squelching noises as he pounded my eager cunt. Soon, my pussy was clamping down on the cock invading me, milking and squeezing Marius’s cock, trying to empty his balls. He shot his load in my pussy with a long, drawn-out groan, hips humping forward as he pumped his seed into me. I wrapped my arms around his shoulders and smiled up at my neighbor, relishing the feeling of his cock pumping my hole full of cum.

“Do you think I’m ready?” I asked as he pulled his softening cock from my sloppy hole.

Marius pushed my legs up and pressed a finger inside my asshole, alongside the dildo. It slid in with a little bit of resistance at first, but my hole eagerly slurped up his finger.

“Soon,” he said with a big smile.

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