Chapter 20 – Jessica

“Shit, baby girl,” Ben groaned as he repositioned me at the center of the bed and brought a hand to my pussy. “I love when you call me that. I can’t even tell you how many times I’ve jacked off to thoughts of you calling me daddy while my cock was moving in and out of this sweet little pussy.”

His confession made me bite lips while the circular motions of his fingers against my clit made me grow even wetter than I already was. I had started calling him daddy as a joke meant to remind both of us of how forbidden our involvement was. However, as our relationship changed the meaning of that word changed as well. It became a teasing thing, a way for me to establish myself as the innocent little girl in search for his guidance and love, and for that reason, it became sexy as fuck itself.

“So have I,” I replied honestly. “Now, please, fuck me and let me make both our fantasies come true.”

A huge smile curled up on Ben’s lips as he wasted no time to pull his hand away and replaced it with the tip of his cock. After over two decades as the world’s biggest virgin, I was crazy nervous about what would happen next. Yes, in the last two days I had masturbated for a Ben’s viewing pleasure, been finger-fucked in a hallway and orgasmed into his mouth while he simultaneously fingered my pussy and ass. Still, I had heard horrible stories about first times and, considering the sheer size of the monster between Ben’s legs, I had to assume it would be a painful fit.

My body involuntarily stiffened as Ben curled his hips, pushing the thick tip of his cock inside me. The sensation was odd and a lot more intense than what his fingers had felt like inside of me, but it wasn’t painful. At least, not yet.

Clearly sensing how tense I was, Ben combed the hair away from my face and brought his lips to my ear. He delivered a soft kiss to the sensitive spot just below my lobe and whispered, “Hush, baby girl. I’ll take good care of you. We’ll spread that pussy nice and slow, okay?”

With my heart planning a riot inside my chest, I bobbed my head and took a deep breath. He held his position, keeping just the very tip inside but pushing no further as kissed my neck and ear. His kisses were, as per usual, delicious and with each one, I felt my body relax a little more.

As my muscles softened, Ben pushed himself a bit further inside me. My lips parted with a gasp as my inner walls spread to welcome a little more of him. There was still no pain, but rather a strange sensation of fullness that was stronger than any word I could use to describe it.

Once more, he dotted slow and comforting kisses across the skin of my neck and jaw until my body was prepared to receive more of him. Then, he pushed himself even further. The odd feeling of being stretched and filled was still there, but now that I knew what to expect, I was no longer afraid. I was just hungry and desperate for more.

Just as before, Ben stopped and held perfectly still to give my body time to adapt to his. As he did, his eyes fluttered and a groan reverberated from somewhere deep in his chest. “Hell, Jess . . . You’re so wet and tight. I’ve never felt anything as good as you, and it makes it hard to stop.”

His words made me feel incredibly proud of myself, like I had made a mark as strong and deep in him as he had on me. That feeling was overwhelming which combined with the growing need I felt was almost too much to take.

Curious and excited to know how intense it would get, I pulled in a nervous breath and said, “Then don’t. You’re not hurting me, and I want more. Keep going. Please, daddy.”

Another groan echoed through the vast room as his lips crashed into mine once more. Ben’s kiss was deep and passionate, as was the roll of his hips that finally pushed his cock all the way inside of me.

“Oh . . .” I cried as he filled me completely, effectively making me no longer a virgin.

Every inch of my body erupted with goosebumps and shivers, but Ben still felt the need to look into my eyes and ask, “You okay, baby?”

I bit my lips and nodded. “Yeah,” I moaned. “More than okay actually. I feel complete for the first time in forever.”

“You’re so fucking perfect it’s addictive,” he said as he kissed me once more.

As we kissed, Ben started pulling his hips back. Each inch that left me made me feel a little emptier and, after experiencing the incredible fullness of our connection, his absence was almost painful. However, before I had a chance to complain and beg him to fill me again, Ben entered me once more.

This time, the roll of his pelvis was harder and faster, filling me completely all at once. It was intense and exactly what I had dreamed that sex would be like. Loud as fuck moans reverberated from my chest as my fingernails sank on the skin of his back.

Understanding my request, Ben did it again. And again. And again. Each time he entered me was better than the last, and before I knew it, my toes were curled, my breaths had turned into pants, and that familiar warmth had taken over my entire body.

“Ben, I’m so close,” I begged as the first sparks of an impending orgasm ignited inside of me.

“Me too, baby,” he admitted in a strained tone.

His voice still hung in the air when he straightened his spine and sat on his heels. He held me tight by the hips, rose to his knees and brought my hips up along with him. As a result, each roll of his hips drove his cock even deeper inside me.

I watched him intently as he kept fucking me with strength and vigor that were unmatched. My body felt like it would explode and my cries became animalistic sounds that matched his primal groans. Then, just as I couldn’t take any longer, Ben pounded his hips against mine one long and final time and I couldn’t contain my voice.

“Oh, my fucking god! Daddy . . .” I shrieked.

And, with that, Ben closed his eyes and called my name while he filled me with his seed.

He kept moving with baby pulses against me as we both basked in the beautiful afterglow of out orgasms. Then, sated and exhausted, Ben lay down beside me and pulled me into his strong chest. He held me so close and so tight I could hear his heart beating and marveled that it was racing as fast as mine.

As I closed my eyes and gave myself to the comfort of his arms, I couldn’t help but feel like I was dreaming or living someone else’s life. Everything that had happened between Ben and me over the last two days was too surreal for me to believe it was true. Still, the possibility that it wasn’t filled me with the most intense fear I had ever felt. After everything I had experienced, there was no way in hell that I could just go back to my ordinary virgin life and be even close to happy with it.

Worried tears prickled my eyes and a knot formed in my throat, but just as I was about to give in to despair, I felt Ben’s warm lips kiss my forehead and his voice echo around me. “How do you feel not being a virgin anymore?”

The reassurance that it was all amazingly real made my heart skip a beat as I opened my eyes to look at his handsome face. With warming cheeks, I said, “It feels amazing and surreal, actually.”

“So, it was that good, eh?”

The mirth in his voice made me smile as well. “No, it was better. Especially because it was nothing how I thought it would be,” I said playfully. Suddenly stricken by a wave of insecurity, I felt the need to check. “Was it good for you?”

“It was too good, baby,” he assured me with honesty in his eyes and a broad smile on his lips. “But now you’ve peaked my interest. How did you think it would be?”

“Awkward, painful and unsatisfying, like most women’s first time,” I deadpanned.

He laughed at my honesty and gave me a kiss while squeezing my ass. “I don’t ever do awkward or unsatisfying, baby. You can rest assured about that.”

“But you do painful?” I asked with real curiosity and a raised brow.

Ben chuckled. “Only under request.”

Completely oblivious to what he meant, I felt my cheeks flush even more as I asked, “What does that mean? Why would someone ask for pain?”

“Because when done the right way and under the right circumstances, it can make sex a lot more fun and even more pleasurable.”

Without thinking, I shook my head and blurted out. “That’s not possible. What we did—what you did to me—there’s no way to improve it.”

“I’m happy you feel that way, baby,” Ben said with a chuckle and a kiss. “But it’s not about improving. It’s about different sensations.”

Still confused, I frowned begging for an explanation. Ben smiled and rolled me onto a pillow. Then, he turned on his side facing me and propped himself on his elbow. In silence, Ben slid his hand to my breast and clamped his finger on one of my nipples. He pinched and rolled it as he had done before, only this time it was harder. Too hard actually.

I opened my mouth to complain about the pain, but before a word came out, Ben said, “Pain is the only sensation as intense as pleasure, and for that reason, when employed correctly, it can amplify an orgasm in ways you can’t imagine. Like your nipple, for instance. I bet it’s smarting as hell now, right?” he asked and, like an obedient girl, I nodded. With a smirk, he continued, “But tell me what you think of this.”

As soon as those words passed through his mouth, he released my nipple. Suddenly, the pain was replaced by wonderful little tingles. I pulled in a deep breath through my mouth at the surprising pleasure. Clearly not satisfied with my reaction, Ben leaned forward and took that nipple into his lips, intensifying the sensation even more.

I moaned and tangled my fingers into his hair, wanting more of that. To my disappointment, Ben pulled away from my breast as quickly as he had latched on to it. He looked me in the eyes and asked, “How did you like that?”

“A lot,” I said in a shaky voice. “I liked it a lot.”

His smile widened. “Now, imagine feeling like that while I’m fucking you. Imagine your whole ass smarting while I’m sliding in and out of you, or being tied and unable to move while I’m going down on you. Imagine how much fun that will be.”

Dry as the desert. That’s how my mouth felt at the image Ben was picturing. In contrast, my pussy had never been wetter. I pulled in a deep breath and nodded, “Yeah, I think I want to try that.”

Once again, Ben chuckled and gave me a peck. “And we will,” he said against my lips, but when I tried to deepen the kiss and get this show running, he shook his head and pushed me away. I looked at him through displeased and narrowed eyes, but he ignored the expression and said, “It’s late, and we have busy days tomorrow. Besides, it’s bad enough that I’m fucking you with your mother in the house. I’m not going to fuck and spank you with her here.”

Although I agreed with his point, I couldn’t help the disappointment I felt. “Fine, but I expect to be fucked and spanked tomorrow. You’ve awoken my curiosity Ben, and I hate to be curious.”

He looked at me with admiration and awe for a few seconds, then said, “You have my promise. Before you go to bed tomorrow night, your ass will be pink, and your pussy will mine. Again.”

Exhilarated by his promise, I pulled him in for a passionate kiss. Once we parted, I kept my lips pressed against his and whispered, “I’m gonna anxiously hold you that promise, Daddy. Good night.”

With that, I got out bed and walked butt naked out of his room. After all the night’s activities walking felt funny, but I enjoyed the feeling for it reminded not only that I was no longer a virgin but also of where my lover—my daddy—had been. Those were my new favorite memories, and I would cherish them forever.