Chapter 4: Deflowering Chinatsu [R-18]

Natsumi smiled and said, "Sure."

Without her glasses, her face took on a different allure. She looked surprisingly sexy without them. When she wore glasses, she had a more intellectual and sophisticated aura. I wondered if it would be interesting to do it with her while she wore glasses, but that was a thought for another time. Right now, my focus was on Chinatsu. I knew that indulging in such fantasies could lead to developing more fetishes, like a glasses fetish, on top of my existing preferences for stockings and pantyhose.

I guess it would just make me a little more unique in that regard.

But back to the task at hand. I turned my attention to Chinatsu, ready to make her experience as comfortable and pleasurable as possible.

"Natsumi, let's get her aroused."

"Huh? Wait, what?!" Chinatsu's voice sounded alarmed. Emotions seemed to be running high today...

"Relax, Chinatsu-chan. I'm just assisting Tsubasa-kun to make things more comfortable for you."

"I get what you mean, but what exactly are you planning to do to get me aroused?"

Natsumi pondered for a moment. "Well, maybe something like this?"

She put her nipple in her mouth and began to suck on it.

"Ah!"

Chinatsu's body trembled beneath her.

"I'll take care of the other one," I chimed in, leaning in to capture her other nipple.

"Ahh! No!"

We both focused our attention on her nipples, gently caressing them with our mouths. As my hand traveled up from her calf to her knees and further to her thighs, her body reacted with soft trembles.

"Nghhh..."

Her shivers intensified beneath me, and I noticed her nipple becoming harder in my mouth. It was a clear sign of her growing arousal.

Simultaneously, my hand crept up her thigh until I reached her vagina. I lightly traced her lower lips with my finger.

"Nghhh?!"

Her reaction was intense this time. The finger I glided over her wet folds came away moist, and her skin radiated heat. Her uneven breaths hinted at her escalating desire.

"Ahhh, Tsubasa... Natsumi..."

Despite the building excitement, I knew it wasn't time to proceed yet. I wanted to ensure she was properly aroused before we went any further. I hadn't breached her hymen yet. Rushing it now would only cause her pain, and that wasn't what I wanted. I wanted Chinatsu to experience pleasure, just like me. It was about both of us, not just my own satisfaction.

"Nhhha!"

I began to stimulate her clitoris, rubbing it gently. With both Natsumi and I attending to her pleasure, I could feel Chinatsu's growing arousal. And it wasn't just her; my own desire was intensifying, and I could sense the same from Natsumi.

After a while, her wetness increased as I continued to stimulate her clitoris. Natsumi released her hold on Chinatsu's nipple and spoke, "I think she's ready."

I released her nipple as well, nodding in agreement.

Her wetness indicated that she was now prepared for penetration. However, Natsumi had more in mind.

"But we still need some more preparation."

"Preparation?" I questioned.

Before I could fully comprehend, she instructed, "Stand up, Tsubasa-kun."

I rose to my feet as she instructed, and she did the same. Her hands reached out and held my cheeks, drawing me closer. She initiated a passionate kiss, and her tongue immediately sought entrance to my mouth. Natsumi was always a fan of deep kisses, exploring each other's mouths eagerly.

"Puhah!"

She released my mouth, and a faint blush colored her cheeks as she took a quick gasp for air. I was sure that my own face mirrored hers in its reddish hue.

"I'm going to prepare you as well," she announced with an alluring determination.

So, that was the kind of preparation she had in mind. Without hesitation, she knelt down before me, forming a circle with two fingers around the base of my dick, and her tongue began to caress and lick it.

"Nhhh, nhaa, ahh, tsuuu..."

"...Gn." I couldn't help the involuntary shudder that ran through me when the warmth of her tongue connected with my member. This was my first time experiencing oral pleasure.

My gaze flickered to Chinatsu. She was observing us with an intense stare, her throat audibly gulping. Perhaps she was curious about trying it too?

Once she had thoroughly coated my length with her saliva, Natsumi stood and smiled angelically, her voice a seductive whisper, "Preparation complete. Now, devour her."

Her appearance might have been angelic, but the way she combined her actions with her words was nothing short of seductive – a playful duality that only added to her allure.

I approached Chinatsu, her arms wide open...no, her legs were the ones inviting me.

"Chinatsu..." I leaned in and claimed her lips, our mouths coming together in a passionate kiss. I exchanged my saliva with hers, the intimate exchange making our desire even more palpable.

"I love you, Tsubasa..." She broke the kiss, her voice heavy with emotion.

"I love you too," I replied as I positioned myself at her entrance. The instant the head of my erection made contact with her wet lower lips, her arousal coated the tip of my member, and I felt her welcoming me in. Holding back in this moment was practically impossible. "I'm going to enter you now."

"O-Okay..."

With gentle pressure, I began to slide inside her, feeling her inner walls embrace and yield to my intrusion. I held her hand and our fingers intertwined, an expression of the emotional connection between us. I was anxious about causing her pain, so I proceeded slowly.

"Kuh...!" A slight grimace of discomfort crossed her features.

"Are you okay?"

"It's fine. Keep going."

Following her reassurance, I continued my descent, until I encountered a barrier that marked the threshold to her most intimate depths.

"Ahhh!"

She moaned in pain as her hymen offered resistance. This was the moment where her innocence would be relinquished, where I would claim her as my own in the most intimate way possible. The woman I cherished, the one who had been my companion since childhood, was now about to undergo a profound transformation under my touch.

A mixture of happiness and excitement flooded over me, an intense emotion that words couldn't capture. It was a sensation of unparalleled dominance and connection, something utterly unique to this moment.

A muffled sound emanated from within her body, and in an instant, a rush of warmth enveloped my length.

"O-Ouch! I-It hurts! It hurts! Uuuuh..."

Tears welled up in her eyes, her face contorting with the pain she was experiencing. I couldn't help but feel a surge of guilt mixed with arousal. The warm sensation spreading through my member was her virgin blood, an undeniable sign of her innocence being lost. The crimson liquid trickled from her pussy, staining the bedsheet beneath her, marking the moment in vivid red.

"I've heard from Chika-chan that the first time having sex is painful, but I've never thought it would be this painful," she said, her voice shaky as she wiped away the tears that had welled up.

"Are you sure you're okay?"

"The pain has subsided a bit, so I think you can start moving now."

With her pale expression slowly regaining a hint of color, I sensed that her initial discomfort might have lessened. Perhaps a new kind of arousal had taken its place.

"I'm going to start moving now."

And so, I began to move, finding a rhythm that I hoped would cause her less pain.

"Ahhh, ahh, uuh," she let out strained moans, her expression still contorted in discomfort.

I paused my movements, concerned. "Chinatsu, please don't push yourself too hard."

"I-I'm okay. It hurts when you move, but I can manage. Don't worry about me."

"But—"

Before I could respond, Natsumi interjected, "It's fine, Tsubasa-kun. You don't have to focus on her pleasure right now. That's just the norm. Most women don't experience pleasure during their first time. There are exceptions, of course, but Chinatsu-chan is clearly not one of them. You can proceed with what needs to be done. After all, you still have one more woman to attend to. Or are you going to stop now?"

Natsumi's words acted as a catalyst, pushing my hesitation aside and urging me forward. I resumed my movements, my hips thrusting against Chinatsu's in an increasingly forceful manner.