Chapter 6: Deflowering Natsumi [R-18]

I held onto her shoulders and gently pushed my penis forward.

"Hnggg?!"

Natsumi let out a cry of pain as I slowly continued to enter her tight passage. I could feel the resistance, so I paused, not wanting to hurt her further. But I knew we were close.

"I-It hurts, Tsubasa-kun."

"I'm almost there, Natsumi."

As the head of my penis finally entered her, the tightness persisted.

"Calm down, Natsumi," came a voice from behind. I glanced slightly to see Chinatsu, who then held my face by the cheeks, forcing me to focus on Natsumi. "And you, Tsubasa, look her in the eyes."

Chinatsu's words resonated as her breasts pressed against my back.

"Natsumi wasn't calm, so her pussy was resisting. You need to help her relax," Chinatsu explained.

Natsumi not being calm was a surprise. The person I knew to be the calmest in the world wasn't calm? Was this some kind of cosmic event?

"Look her in the eyes and say, 'Calm down, Natsumi. I'm here,' or something."

Chinatsu's gaze fixed on Natsumi.

"Natsumi's scared right now. That's why you have to keep reassuring her and help her relax."

Scared? Seriously? But she had been so composed throughout this whole experience.

"She might have seemed composed, but deep down, she wasn't. She was just suppressing her fear so you could have your way. Natsumi acts like an older sister to us, even though she's the same age. She wants you to enjoy yourself and has been forcing herself to accept the situation, even though she's scared. But now, her body is showing the truth, more than her words ever could."

I looked at Natsumi. She had a surprised expression on her face, but then she smiled.

"You're right, I guess, Chinatsu-chan. Don't get me wrong, though. I am fully prepared to have sex with Tsubasa-kun right now. But..."

"You're scared of feeling pain, aren't you?"

Natsumi averted her gaze.

Oh, I see... I remembered that Natsumi was kind of fearing pain. There was an accident back then when we were kids that probably scarred her mentally.

"If you're not comfortable with it, we can stop."

I attempted to withdraw, but Chinatsu pressed against me, and despite her discomfort, Natsumi wrapped her legs around my waist.

"Don't be absurd, Tsubasa-kun. I said I'm already prepared to have sex with you. I didn't say I hate it, I'm just scared, but I believe you have the ability to alleviate that fear in me." Her hands extended toward me. "Hold my hand," she requested.

"That's right, Tsubasa. And isn't there a saying that it is a man's shame to ignore a woman's advances? If you stop this now, you'll be shaming yourself, you know," Chinatsu added playfully.

I nearly chuckled at her remark. I kissed her on the lips before turning my attention back to Natsumi.

"Alright, I'll do my best to make it as comfortable as possible. Just let me know if it hurts, okay?"

I released my grip on her shoulders and shifted my hands to hold hers. I realized that my previous grasp on her shoulders might have been a factor in her fear; it could have given her the impression that I was trying to force her down for penetration. While my intentions weren't to overpower her, I hadn't fully considered her perspective.

As I held her hands, she nodded, indicating that she was ready. I sensed her vaginal muscles starting to relax, indicating that she might be more receptive now. It was tempting to thrust and begin moving inside her, but I resisted that urge. It wasn't just about what I wanted; I had to consider her feelings too.

Pushing forward with force might lead her to associate sex with fear and pain, possibly causing vaginismus. While I knew that our love could still thrive without the physical aspect, there was a unique connection that came from the intimacy of our bodies joining together.

When my glans finally made contact with the barrier preserving her innocence, a wince of pain crossed Natsumi's face.

"Take a deep breath. This is going to be very painful," I advised her. While I could only speculate about the intensity of the pain associated with deflowering, considering I am a man, I understood that the experience could be quite uncomfortable.

Natsumi followed my guidance and inhaled deeply, her vaginal muscles gradually relaxing in response. The membrane before me felt fragile, as though it might rupture with further pressure. I approached with careful intent, aiming to create minimal discomfort.

"Ouch... It hurts," Natsumi expressed, her voice strained.

"Don't worry, Natsumi. Tsubasa will be gentle," Chinatsu reassured her, her tone filled with confidence.

"Y-Yes, I understand," Natsumi replied.

Chinatsu's unwavering confidence in my ability puzzled me, but I was determined to proceed without causing undue discomfort.

As I continued to push, Natsumi winced with each incremental movement. I could see the tears welling up in her eyes, a visible testament to the pain she was enduring. And then, with a final push, the barrier gave way.

"Ouch—!" Natsumi cried out in pain as her hymen tore. Instantly, blood flowed from her vaginal opening, staining the bedsheet beneath us.

"I'm finally inside you... Are you holding up, Natsumi?"

"Y-Yeah. It was really painful, but...at the same time, I'm happy that I'm finally experiencing this with you."

"Truly? That's a relief."

I let out a sigh of relief. It seemed that her fear was not as pronounced as I had anticipated. I waited for the initial pain to subside and inquired, "Is the pain still intense?"

"It's still there, but... I don't want you to be overly cautious. You can start moving now."

Her smile was as radiant as ever. My arousal surged as I gazed at her mixed expression of pain and pleasure. With that encouragement, I initiated my movements.

"Ahhh!"

Her cry was a blend of pain and a hint of excitement as I began to move within her. I took care not to be too forceful, prioritizing her comfort as we moved together. Despite her discomfort, her eyes seemed to urge me to be more assertive, so I gradually increased the pace of my thrusts.

"Ahhh!"

Though it was her first time, and this was essentially my second time, I was determined to make her experience pleasure amidst the pain.