In the last week, Darryl and I had fucked almost every day, and every time felt like the best sex I had ever had. Even though we mostly met up to fuck, we had also spent a lot of time talking afterward; we got along really well. Even though my pussy was sore all the time from being stretched and pounded by his massive black cock, I could never say no when he called or texted me. I needed his cock too much; I was addicted to it.
That night I was at his place; I had been there a few times before. He was on top of me on his king-size bed, kissing me as his hand rubbed my wet pussy. We were both naked, his hard cock was pressed against my stomach, but he didn’t seem to be in a hurry to get inside me.
“Put your ass up,” he whispered to me as he got off of me. I did as I was told, and he got behind me. Instead of pushing his cock inside me like I had thought he’d do, he leaned in and started to eat my pussy from behind. I moaned quietly, loving the way he pushed his tongue deep inside me, swirled it around before pulling it out and flicking my clit with it.
He wrapped his arms around my ass like he was hugging it, and suddenly I felt his tongue gently swiping over my hole. I gasped. We had done a lot of things by then, but we had never done any kind of anal play. Darryl licked over my hole again.
“Oh!” I gasped. He pulled away a little bit.
“Is this okay?” He asked.
“Yes, you just surprised me,” I answered.
“I couldn’t resist this delicious-looking little hole anymore,” he moaned before leaning back in. He started to lick it faster, rubbing his tongue against my hole, moaning loudly. He grabbed my ass cheeks so he could spread and squeeze them as he continued licking my hole eagerly. I started to moan, loving the feeling.
I had gotten my ass eaten once before by my ex-boyfriend, but he wasn’t really into it and had given me just gentle, barely-there licks for a few minutes before he was done. This was completely different; Darryl seemed to be really into it━after all, he was the one who started to lick my hole without me even having to ask him to.
“Fuck, that feels amazing,” I moaned loudly. It made him lick it even faster, pressing his tongue against my hole harder.
He brought his right hand down to my pussy and pushed two fingers inside me, fucking me with his fingers while his tongue worked on my hole. It felt heavenly, it felt so good that I probably could have climaxed just from the anal stimulation, but his fingers inside my pussy made my orgasm build up faster.
My upper body collapsed down on the bed when my orgasm hit me, and the only reason why my ass was still up in the air was that Darryl was holding it up, his face still buried between my cheeks, his tongue still working on my hole all through my orgasm. His fingers were still inside me but they had stopped moving.
Finally, he pulled away and laid down next to me, a wide grin on his lips. I was still breathing hard.
“I guess that felt pretty good, huh?” He smiled.
“Yeah, it felt amazing” I nodded.
“I want to fuck your ass so bad,” he said quietly. My eyes widened.
“Do you realize how fucking huge your cock is?” I asked, making him chuckle.
“Yes, I’ve noticed. I didn’t mean now, but if it’s something you’d want, we could like… train your ass to be able to take my cock,” he said, his tone curious and hopeful. I thought about it for a moment.
“It would take a lot of training, I haven’t done anal in a while, and I’ve never had anything nearly as big as your cock in, well, any of my holes before I met you,” I said.
“It’s okay; I’m very happy with your pussy and mouth,” he smiled.
“Darryl, I didn’t say no,” I grinned. The look of surprise on his face was hilarious.
“Really?” He asked, sounding so excited.
“Yes. I assume that you’ll help me with the training, and I know it’ll take a long time, but I want it; I want to be able to take your cock in my ass,” I smiled at him.
He pushed me onto my back, got on top of me, and started kissing me. I could feel his smile against my lips.
“Fuck, I can barely wait. You’re so fucking hot, holy fuck,” he moaned. I could feel his hard cock pressing against my lower stomach right before he pushed inside me with one quick movement. We both moaned as he pushed inside my tight, wet pussy.
“I can’t even imagine how huge your cock is going to feel in my ass,” I moaned as he started fucking me.
“It’s going to be so amazing. I want to start your training as soon as possible,” he panted, thrusting into my tight pussy faster.
“Me too,” I nodded. Neither of us was able to talk much after that. That night Darryl came faster than he ever has with me before, and I knew it was because he was so excited by the idea of one day fucking my ass.
Two days later, I was doing the dishes when my doorbell rang. I wiped my hands on a kitchen towel before heading to the door. Darryl was looking excited, barely able to stand still as he asked if he could get in. I stepped to the side and he rushed in, immediately turning to face me.
“What’s up?” I chuckled.
“I got you something,” he said. Before I could ask anything, he pulled something out of a bag he was carrying and handed it to me.
“Anal training set,” I read the label.
“It has three different sized anal plugs; it’s meant for beginners. Oh, and I got lube!” He dug the tube out of the bag and handed it to me.
“Oh, Darryl, you didn’t have to; I could have bought these myself,” I said, feeling bad that he had used his money on me. He waved me off.
“Don’t worry about it; I wanted to buy these for you. Besides, we are going to need a lot more toys, so it’s only fair that I buy some of them,” he said.
“Do you wanna try these out right now?” I asked with a smirk on my lips. I’ve never seen him that excited.
“Can we?” he asked. I nodded. “Yes!”
He got out of his jacket, went to wash his hands, and then we rushed to the bedroom. He was practically ripping my clothes off of me while kissing me, making me giggle with how eager and excited he was.
Once he had me naked, he laid me down on my stomach and got between my legs. He spread my cheeks so he could lick my hole again, getting me warmed up. After a moment, he pulled away, spit on my hole, and started to rub it with his fingers, adding a bit of pressure but not pushing his finger inside quite yet.
“How do you feel?” He asked. I raised my head to look at him over my shoulder.
“So good. The lube and toys are next to me; please, finger my hole,” I moaned.
Darryl reached for the lube, poured some on his fingers, and gently rubbed it on my hole.
“Are you ready, babe?” He asked gently.
“Yes, push one inside,” I nodded.
It had been so long since the last time I had felt anything pushing into my ass. His finger went in easy, pushing past the tight muscle. I moaned quietly as he slowly pushed his finger in deeper.
“Fuck… It’s going to take so much training to fit my cock in this tight hole; it’s even tighter than I imagined,” Darryl moaned.
“And I’m going to love every moment of it,” I smiled at him. He had been staring down at my hole, but when he heard my words, he looked at me. A smile spread on his lips.
“Me too.”
Darryl moved his finger inside me in a circular motion, stretching my hole open before pushing another thick finger inside. I could feel my hole stretching around his fingers.
“Your ass feels so good; it’s so soft and smooth inside, so warm,” he said as he kept slowly fingering me.
“I can’t wait for you to feel it around your cock,” I moaned.
“Me neither. Are you ready for the smallest plug?” he asked. I opened the package and dropped all three plugs on the bed. I handed him the smallest one, asking him to please put it in me.
He pulled his fingers out slowly, covered the plug in lube, and started to push it inside. It slipped in easily; it wasn’t any thicker than Darryl’s two fingers that had already stretched my hole open a bit.
“Beautiful…” He said so quietly that I just barely heard him, staring at the heart-shaped sparkling base of the plug. He leaned down to place a kiss on my ass cheek, making me giggle before he grabbed my hips and gently lift my ass up.
“I want to fuck you,” he said as he rubbed his thumb against my soaking wet pussy. “I want to fuck you from behind while you have a plug in your ass; I want to see it.”
“Fuck me,” I said. His cock slid inside me easily, my pussy still tight around it but more used to his size by now. He held my ass cheeks spread the whole time as he thrust in and out of my pussy, his eyes glued to the pretty plug.
“We need to get you some dildos, big ones. And a plug with a wide base, so it keeps your hole stretched,” he spoke as he fucked me.
“Mmh, fuck! Feels so fucking good,” I moaned, enjoying his cock too much to concentrate on what he was saying.
“Your ass looks so fucking good with a plug in it,” he moaned.
“It’s going to look even better with your big black cock in it,” I winked at him from over my shoulder.
“Fuck,” he grunted and started to fuck me harder.
Even though the plug was small, I felt so full with his cock in my pussy and the plug in my ass. I could feel my orgasm building up, and I could tell that it was going to be an intense one. Darryl kept fucking me hard, pounding my pussy from behind.
“I’m about to cum!” I screamed.
“Cum! Cum on this fucking cock while your ass is plugged,” Darryl groaned, smacking my ass.
I screamed as my orgasm hit me━it was so intense; it felt so different from my usual orgasms. I could feel my hole pulsating around the plug. My entire body was shaking and twitching as endless waves of pleasure washed over me, each one stronger than the one before.
“That’s it, that’s a good girl,” Darryl praised me as he fucked me through my orgasm.
“Holy fuck, that was so strong,” I gasped.
“Was it because of the plug?” He asked, slowing down a bit.
“Yeah, I think so,” I nodded.
“Good, that’s good,” he smiled, gently running his hands up and down my back.
“Do you want to switch the position?” I asked.
“No, I’m close. I wanna see your plugged ass when I cum,” he said.
“Already?” I grinned.
“You should see my view; I could’ve filled you up as soon as I pushed inside,” he chuckled, defending himself.
“Okay, I understand. Go ahead, fuck me,” I smiled.
Darryl started pounding me again; I could feel him pressing on the base of the plug as he fucked me. He lasted longer than I had expected him to. When he came, he pulled out and sprayed his cum all over my ass and the base of the plug.
“Fuck!” He groaned, admiring the view that was now even better than before. I knew he would have wanted to look at it for even longer, but I wanted to suck his cock clean, so I turned around and took his cock into my mouth. He moaned loudly, pressing his hand on the top of my head, and thrust in a little bit.
I sucked his cock for a moment, licking it from balls to the tip until it was all clean. He got a towel and wiped his cum off of my ass.
“Do you want me to take the plug out?” He asked.
“No, not yet; I want to keep it in a bit longer,” I said with a small smile on my lips. We laid down on my bed, facing each other.
“You’re fucking amazing; you know that?” He said gently. I smiled.
“So are you, Darryl.”
He leaned in to kiss me.
During that week, he used his fingers and the plugs to stretch my tight hole every time we had sex, and he spent more time eating my ass than my pussy. Darryl was keeping me fully satisfied, I didn’t feel the need to masturbate, but I still found myself rubbing my hole while in the shower most nights, craving that stimulation.
Once we had worked my ass to the point where I was able to take the medium-sized plug easily, I went shopping for more toys. That night when Darryl came over to my place, I had my new toys lined up on my bed. His eyes widened when he saw them.
“When did you get these?” He asked.
“Earlier today, I got some help picking these up from a very nice lady at the sex shop downtown,” I grinned.
Darryl picked up one of the bigger toys I had gotten.
“I know I’m not able to take all of them yet, but I figured that it would be better to have them ready for the moment when I will be able to fit them inside,” I explained.
“I can’t wait to use these on you,” Darryl said, examining closer a big, wide-based plug.
“Well, which one do you want to start with?” I asked. He looked at the toys before picking up a suction cup dildo; it was about seven inches tall and a bit thicker than any of my old dildos.
“Do you think you could take this one today?” He asked.
“If you work my hole open, yes,” I winked.
Darryl did just that. We got naked quickly, and a moment later, he already had three fingers inside my tight ass. I was moaning loudly, one hand teasing my nipple, another one rubbing my clit. Darryl finger fucked my ass deep and fast, his fingers deep inside me.
“Make me cum, please make me cum,” I whined, so close to my first orgasm of the night. Darryl grabbed my wrist and gently moved my hand away from my pussy. I looked at him. “No, please, let me touch it; I need to cum!”
“You’re so close already; you can cum just from my fingers; I know you can. Relax and concentrate on my fingers in your ass; I know you can cum just like this,” Darryl told me.
At first, I thought that I wouldn’t be able to, I had never come from anal stimulation only, but suddenly the familiar feeling started to build up inside me again. By now, Darryl knew how my body moved, how my breathing changed, what kind of sounds I made as I was about to cum.
“That’s it, cum for me, cum from me fucking your ass with my fingers and nothing else,” he cheered me on gently. A moment later, I came, my body spasming as a different kind of orgasm washed over me. I was gasping for air, unable to believe that he had just made me cum just from anal stimulation.
“There you go, that’s my good girl,” Darryl smiled at me.
“Holy fuck,” I breathed out.
“That was so fucking hot. I knew you’d be able to do it,” he smiled, still moving his fingers slowly in and out of my now stretched hole.
“I’ve never been able to do that before,” I told him. He smiled at me gently as he pulled his fingers out. He picked up the dildo we had decided to use.
“I’m so proud of you. Now, do you think you’re ready for this one?” He asked, holding the toy up. I nodded.
“Yes, just start slow with it,” I nodded.
Darryl covered the toy in lube, squirting some straight into my open hole, too, before starting to push the toy in slowly. My hole was already open from being fucked by three of his thick fingers, but I could still feel it stretching a little bit around the sizeable toy.
“Good girl, it’s sliding in so easy,” Darryl whispered, pushing the toy in deeper before pulling it halfway out. He slid it in and out slowly, gently, watching my reactions.
Once the toy was sliding in and out of me easily he suddenly pulled it out and got off the bed. I looked up confused, wondering what was going on. Darryl bent down and smacked the dildo’s suction cup onto the floor, making it stand up proud, pointing up towards the ceiling.
“Come here,” Darryl said, holding his hand out for me, helping me off of the bed. He tossed a pillow on the floor in front of the toy. “Sit on the toy.”
I positioned myself on top of the toy, guiding it back into my waiting hole. Darryl stood in front of me, patiently waiting as I got comfortable with the pillow under my knees, the toy back in my ass. Once I was ready, I looked up at him. He smirked at me as he brushed my hair out of my face with his fingers.
“Open up,” his thumb brushed my lower lip, his hard cock in his other hand. I opened my mouth wide, ready for what was coming next.
Darryl pushed the tip of his cock between my lips, allowing me to swirl my tongue around it, making it wet and slippery. I kept my eyes on him the whole time, knowing how much he loved eye contact while his big black cock was in my mouth.
“I want you to fuck your ass with that toy while I fuck your face; I want you to do your best to keep riding it no matter how hard or deep I fuck your throat, do you understand?” He asked. I nodded, not letting his cock slip out of my mouth. “Good girl.”
He grabbed the back of my head and started to push his cock deeper into my mouth. I moved down, taking the dildo deeper into my ass before moving upwards. Darryl was fucking my mouth slowly at first, allowing me to get to a nice rhythm on my toy before he started to move faster. His hand grabbed my hair, pulling my head back and forth, his cock forcing its way down my throat.
“That’s it, fuck your tight fucking hole with that toy, ride that fake dick while I fuck your pretty face, that’s my good girl,” Darryl moaned. My eyes were already watering from how hard he was fucking my throat.
I started touching my tits, playing with my nipples, loving all the different kinds of stimulation. The toy felt amazing in my ass; I was doing a good job at fucking myself with it even though Darryl was fucking my throat brutally hard. Drool was dripping down from the corner of my mouth, all the way to my tits, working as a lubricant as I kept rubbing my hard nipples and squeezing my tits.
“Fuck, you look so amazing like that, with my cock deep down your throat, that toy deep in your ass. Come on, keep going, cum on that fucking dildo, I know you can,” Darryl groaned.
He was right; I could feel my orgasm getting closer, building up inside me quickly. The toy was massaging my walls perfectly; my hole stretched wide around it. The way Darryl was fucking my throat was turning me on like crazy; I knew I’d cum any moment now.
Even though I had felt it building up, my orgasm still took me by surprise, mostly because of how strong it was. My body shook and twitched uncontrollably with an orgasm that seemed to last forever. Darryl pulled his cock out as I moaned and screamed through my climax.
“Ass up, now!” He said hurriedly, helping me up and off of the toy. He manhandled me into the position so that my face was against the floor, my ass high up in the air. He was stroking his cock hurriedly.
“I’m gonna push the tip in; I want to cum in your ass, is that okay?” he asked. I nodded, still lightheaded from my orgasm.
Darryl spat on his cock and slowly pushed the tip in. It was even thicker than the toy I had just bounced up and down on, the stretch made me wince a little bit, but Darryl kept his promise and didn’t go deeper than that.
“Fuck, it’s still so tight,” he grunted right before he filled my ass with a huge load of hot cum. I could feel it spraying deep inside my stretched, wide canal.
He pulled out slowly, and I could feel his cum dripping out of my hole down to my pussy and the floor. I was too exhausted to move just yet.
“Fuck, you look amazing like this… Is it okay if I take a picture?” He asked.
His question made me giggle and I nodded. He told me to stay still while he went to get his phone. Once he got back, he took a few pictures of me just like that and some closer photos of my stretched, cum filled hole. Then he asked me to reach back and spread my hole even wider for him for a few more photos. Once he was satisfied, he picked me up from the floor and lowered me gently onto the bed. He laid down next to me.
“How do you feel?” He asked. I smiled.
“Good. I still can’t believe that I was able to cum from anal only, and I did it twice!” I said.
“It was amazing and so fucking hot! I don’t think it’ll take much longer until you’re be able to take my cock in your ass; you’ve been making progress way faster than I had expected,” Darryl said.
“I think you’re right, it did hurt a bit when you pushed the tip in, but it wasn’t too bad. I’m sure that you’ll be able to pound my ass soon,” I grinned at him.
“I hope so; I can barely wait,” he smiled and leaned in to kiss me. That night he fell asleep next to me, making it the first time he’d ever spend the full night at my apartment.
