My Childhood Bully is a Mafia Boss-Chapter 60

Ivy

Aidan’s fingers brushed against my skin as he reached for the bedside table. My pulse quickened, and I found myself holding my breath in anticipation.

I told him it was okay, but now I am wondering if I had lost my mind when I agreed to this....act.

"Are you scared, Ivy?" drawled.

Irritation flickered in my mind at his amused expression. He was enjoying this way too much.

"This better not hurt too much, jerk," I snapped, making him chuckle.

"And you better not break something," I blurted out.

His eyes lit up with more amusement. "Break something? I think your body can take more than you think. You are not made of glass."

"I appreciate your confidence in me, Aidan. But I’ve never done this before, and I am not sure I trust you completely," I said.

I was scared, but more than that, I was turned on, and that was the strange aspect of it. I have never been this adventurous in bed.

I looked into Aidan’s eyes. The thought of his thick cock in there thrilled and terrified me at the same time. He would tear me in half!

He slowly got up and grabbed a tube of lube and a condom he kept in his dresser.

I furrowed my brows. "Why do you have that ready? Do you make a habit of bringing girls here and fuck them in the ass?"

Aidan laughed. "Oh, no, sweetheart. You are the only one I’d do this for."

I rolled my eyes. Such a smug little bastard!

"Spread your legs and arch your back," he ordered. He could barely hide the eagerness in his voice. I didn’t make another sound and did as I was told.

He suddenly grabbed my ass and squeezed them, making me yelp. He spread my butt cheeks and stared at it directly. "What a pretty pink hole you got there. I’ll have a lot of fun playing with it."

Heat crept up my neck and cheeks at his vulgarity. I flinched as he softly rubbed his thumb over it.

He put his hand between my legs. My sex was slick with my juices.

"You act all scared but so turned on by this. Is my sweet little Ivy secretly a bad girl?" he teased.

I bit down on my lip, fighting back a moan. Damn him, he knew how to turn me on with his dirty talk.

"It’s been a long time since I’ve felt this..." my words trailed off.

He chuckled and gave me a searing look that made me shiver with desire.

He squeezed the lube and rubbed it all over his dick, making the slick sound travel through my heated veins.

He suddenly lowered his head and pressed his mouth on my vagina, then licked me from behind.

I moaned and thrust my hips towards his face, allowing him to bury his tongue deeper inside my core.

"Aidan, wait..." I croaked out and gripped my pillow tightly as if I’d float away if I didn’t.

But Aidan wasn’t waiting for anyone. He spread me apart some more and dragged his tongue across my mound, licking and sucking. He reached under me and grabbed one of my breasts, then squeezed while thrusting his tongue inside.

"Ai...Aidan..." I said in a hoarse whisper. Warm liquid poured out of my entrance, and my body writhed under him as I came.

"Alright, my sweet Ivy, it’s my turn to feel good now. I hope your tight little ass can take my cock because I’m planning on putting it all the way in," he whispered in my ears, then lightly bit my earlobe.

"If you don’t stop being a jerk, I will change my mind," I hissed.

Aidan chuckled in amusement. He spread my cheeks apart again.

"Just so you know, I wouldn’t do this for everyone else," Aidan crooned.

"Do wha....ohh?" My incomplete sentence ended in a confused moan as he started to lick my asshole.

Oh, god...does he have no shame!?

I tried my hardest to suppress my screams of pleasure as he swirled his tongue around my rim. I yelped as he thrust a finger inside.

"You like this, don’t you? My dirty little Ivy," Aidan added one more finger, then another, and thrust harder. He moved them around, stretching me out.

"Tell me if it’s too much," he murmured. I shivered as I felt his breath on my neck.

"It’s okay," I assure him, my voice shaking with the intensity of the moment. "Just... take your time."

He rubbed some lube and thrust his fingers in me again. After a while, I felt the head of Aidan’t penis entering my rectum and gasped. I tensed up, bracing myself for the pain I knew was coming.

"Just breathe, Ivy. Do not tense up, or it will hurt a lot more. Just relax and let me in," Aidan whispered in my ear.

"That’s easy for you to say," I mumbled. "You’re not the one who’s about to get a fat cock shoved up your ass...."

He chuckled and trailed the tips of his long, graceful fingers down my spine. "Now, this is important, Ivy. Every time I push in, you’ll push out, all right? Can you do that for me?"

"Yes," I whispered.

He hadn’t moved yet, and only the head of his cock was in, but the pressure was near unbearable. It wasn’t painful, really. It was just uncomfortable, and I wanted him to get going already.

I heard a squirting noise and realized he must be putting on more lube. He grunted and tossed the tube where it landed on the mattress next to my body.

"Push out," he ordered, sounding as though he was gritting his teeth.

I took a deep breath and obeyed. It hurt, but not as badly as I imagined. I bit into the pillow as he once again stopped. I realized he was letting me get used to the feel of him. He was being considerate.

He grabbed my hips and ordered me to push out again while he advanced a bit more into me. "Good girl. You’re doing so well. I’m halfway in already." His voice was rougher now, barely recognizable as his speaking one.

I was in pain, but it wasn’t horrible and I could breathe through it. He was only halfway in? Jesus, how much more dick did he have?

I felt him pull out a little before pushing back in again. It was such a tiny move, but the odd combination of pain and something that resembled pleasure took my breath away.

"My sweet, sweet Ivy," he crooned as he began to massage her lower back by kneading the flesh with his thumbs. "Don’t fight it, love. I’m already in your ass. You might as well take the rest of it."

I relaxed and let go, reflexively pushing out as he surged inside. I gasped as his pelvic bone hit her ass.

Aidan’s penis had invaded my rear. He was deep inside me, big and throbbing, threatening to split me in half.

"Good girl, Ivy," he growled somewhere in the vicinity of my ear.

I allowed myself to go limp as Aidan took my weight by grabbing my hips.

"Are you okay?" he asks, his voice filled with concern yet still laced with an edge of desire.

"Y-yes," I stammer, my breath coming in short pants. "It’s starting to feel good now."

"Good," Aidan murmured. As the pleasure built, I found myself lost in this new sensation, the connection between us deepening with each passing moment.

I could hear his hard breathing. He was struggling to keep control. God, when he entered me again, I almost moaned out loud. On his way back in, I felt it in that secret spot inside my vagina that when hit right, made me see stars.

"I want to see your face while I fuck your ass, Ivy. Turn around and get on your back." He carefully pulled out of me, making me whimper. From pleasure or pain, I didn’t know what.

"Ready for more?" he whispers seductively into my ear.

"Please," I beg, my voice shaky from the anticipation.

He took off the condom he was wearing and put a fresh one on before getting back on the bed and between my legs. He grabbed my thighs and pulled them over his, spreading me wide open for him.

The half-smirk on his face made me a little nervous. In the moonlight coming through the windows, he looked like a very handsome devil.

"Take a deep breath for me, Ivy," he commands softly after applying more lube on me, and I obey without hesitation, trusting him completely.

As he guides himself slowly inside me, I’m struck by the intensity of the sensation – it’s unlike anything I’ve ever experienced before. It takes all my willpower not to tense up, remembering Aidan’s earlier reassurances.

"Doing so well, Ivy," he praises, allowing me time to adjust again before continuing.

I couldn’t describe the sensation. He was hitting all the right spots he would be if he had penetrated my pussy instead, but there was an element of darkness to having sex this way that made it more... delicious.

He was fucking my ass, but I was looking right at him. He wasn’t behind me, so I couldn’t hide from him.

Just as he promised, he started slow—unbearably slow—pulling halfway out before pushing it back in. From under the veil of my eyelashes, I could see the strain on his face. He was really struggling to control himself.

And I was starting to feel really, really good. When Aidan increased the tempo of his thrusts, I could no longer help the moans that left my mouth.

Aidan was kneeling in front of me and he had my thighs draped over his as he surged in and out of my ass.

It was the most erotic thing I had ever seen in my life. When Aidan reached down and began to rub my clit, I lost it and had the biggest orgasm of my life. And then, another.

Aidan just kept going, fucking me while I screamed his name and probably told him I loved him and would have ten of his babies if he would just keep doing what he was doing. And then I came again. And again.

Finally, Aidan reached his own orgasm and froze above me. He said, "Oh, God, Ivy. I love you so much."