DxD: My Main Skill is Winning Hearts

"Is this your first time, Leo? Or do you have experience?" Rias asked me.

She was literally riding me, her white panties on my lap, over my cock. She must have felt the bulge in my pants, which was why she looked so flushed and embarrassed. That was probably also why she was sure I would approve.

"It's my first time."

"It's my first time too... Since we're going to do it all the way and neither of us has any experience, it's best to start slow." She said as she took one of my hands and placed it on one of her breasts.

When my hand touched them, it was infinitely better than what I had fantasized about on my own. It was very different from feeling it over her bra because there was an exchange of heat. As the warmth of Rias' breasts transferred to the palm of my right hand, a shiver ran down my spine and spread through my body. Rias' eyes met mine and I could see the pleasure in them.

"That time you just stared at them while I slept, didn't you?" Rias whispered. "How does it feel to finally touch them?" She held my hand, forcing me to touch them.

Her breasts were soft and firm at the same time, but my right hand sank down as if touching a pillow. "It's-it feels incredible."

She smiled slightly. "Let's explore these new sensations together, shall we?"

She took my left hand and led it to her other breast. My hands began to move naturally, massaging gently as I watched her every reaction, trying to learn how breasts worked.

Rias arched her back slightly and let out a sigh of pleasure.

"That's it... that's good, Leo..." Rias' voice trembled slightly. "That's it~ Keep it up."

My eyes met Rias's again, and I saw something more than just desire in them. She felt pleasure, but it wasn't natural, not like when Akeno and Asia deliberately wanted to do sexual things with me. Rias looked at me differently. There wasn't that sparkle of curiosity or excitement. This lack of sparkle was a silent plea for something beyond what we were about to do.

Still, I didn't want to let go of this opportunity. Ria's beauty was breathtaking, her parted lips inviting. I leaned forward, smelling the sweet scent of her hair, and kissed her neck. Her skin was warm and soft, and I could feel her pulse racing as I massaged her left breast.

Rias let out another soft moan, encouraging me to continue, but at this point I realized that as much as I really wanted to continue, and Rias didn't seem to be that uncomfortable, it wasn't best in the long run to do it here and now.

I didn't want to be the man who stole Rias, I wanted to be the one who fought for her. And what was the point of possessing her like that? I would lose my virginity to the woman I wanted most in my life because of a desperate request from her, not because of a feeling of unconditional love.

Yes, I could feel Ria's heart beating fast, even with all the flesh on her chest. Her heart was beating even faster than mine.

I took a deep breath, trying to calm the storm of emotions inside me.

"Laugh... I... I can't."

Her eyes widened slightly, and a shadow of disappointment crossed her face. Before she could say anything, I removed my hands from her breasts.

"Not like this, not like this. I don't want this to be a thoughtless act out of urgency or necessity."

Rias blinked a few times, processing my words. Then something changed in her expression. Her face softened to understanding and perhaps relief. She sighed deeply as she leaned forward to embrace me. She wrapped me in her arms, placing her breasts on mine and intertwining our hearts. I could feel the rapid beating of her heart gradually slowing.

[You chose OPTION 2 at Choice Point 3.]

[You received 2 hearts from Rias Gremory].

"Leo..." she whispered against my neck. "I... I'm sorry. I almost forced you into something you didn't want..."

She pulled away slightly, just enough to look into my eyes, and I could see the gratitude reflected in them, along with the sparkle of the other girls usually had.

"Thank you, Leo. You really are a special servant." She gave me a shy smile, the kind that makes any guy feel a wave of tenderness.

I was about to reply when she moved closer again, her gaze dropping to my lips, then meeting my eyes again.

"Can I... can I at least kiss you, Leo?" Rias asked, but the truth was that our faces were so close at that moment that she didn't even have to ask.

I knew I'd made the right decision in refusing her at that moment, but now that I'd already won the hearts, a kiss wouldn't change anything for the system. So I grabbed her neck and pulled her in for a kiss.

Our lips touched and the kiss quickly became intense. Her taste was sweet, a mixture of strawberries and something unique to Rias. And from the way she kissed me, Rias seemed to understand that I wasn't rejecting her because I didn't like her, but because of the context and her emotional state.

When we finally broke apart, we were both panting. Rias leaned her forehead against mine, looked at me and said:

"Anyway, you got something from me today that I've never given to anyone else, Leo. That was my first kiss."

Her words made me even more excited. But an intense glow that filled my room again interrupted the silence. Another magical circle formed on the floor as a figure began to materialize in the center.

When the light finally faded, a woman with long silver hair and intense blue eyes was revealed. She was dressed in a maid's outfit, and a cold air of seriousness emanated from her.

"I seem to be a bit late."

"Grayfia..." Rias said, looking at the woman with a little disgust.

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NEXT CHAPTERS:

Chapter 34 - Challenge
Chapter 35 - Raiser Phoenix, The Worst
Chapter 36 - Boosted Gear X Phoenix
Chapter 37 - Explo... sion?!
Chapter 38 - Devastation of Destruction
Chapter 39 - Gremory Mansion
Chapter 40 - System Update
Chapter 41 - Your chances? Very High! (R-18)
Chapter 42 - Asia Deep Throa... Khum! (R-18)
Chapter 43 - My First Time with a Nun (R-18)
Chapter 44 - Rhythms & Poses (R-18)
Chapter 44.5 - Asia Argento POV (R-18)

Chapter 45 - Attribute Points

Chapter 46 - Welcome Back

Chapter 47 - Collecting Artifacts

Chapter 48 - New System Challenge!

Chapter 49 - Heating Akeno (R-18)

Chapter 50 - Tight Walls (R-18)

Chapter 51 - Arara~ (R-18)