Chapter 16

Chapter 16 - First Time (3)

"Ughh!"

I had my second ejaculation today. It happened within about 20 seconds while Lily was stroking me. It ended so quickly that even Lily seemed surprised.

Despite being turned on from kissing and hugging earlier, it shouldn't have led to ejaculation this fast from Lily's inexperienced touch. It was me who had moved my hips and couldn't hold back, resulting in this outcome.

From Lily's perspective, as soon as she grabbed my penis, I started shaking and ejaculated on my own. It must have seemed quite comical.

But that's fine. The overwhelming arousal burning in my brain was settling down. If I kept holding her like this, she would end up in pain again just like the first time.

I wiped the semen off Lily's hand and faced her.

"Lily, please be honest. How much did it hurt earlier?"

"...It didn't hurt that much. Just a bit."

"What would you do if I said I wanted to have sex with you every day?"

"...I'll let you."

Lily's gaze momentarily wavered. It was clear that it had hurt quite a bit.

"Lily, I want to have sex with you a lot. But I don't want you to be in pain."

"Mm."

"Do you know how we could make it less painful for you?"

"...Kiss a lot?"

"…"

She said such an adorable thing. I instinctively hugged her tightly and gave her a peck on the cheek. I repeated it over and over, and finally kissed her cheek with a strong suction.

"No, it's about getting your body used to it."

From my knowledge (source: erotic books), girls are supposed to feel more pleasure than guys once they get used to it. Even if it wasn't to that extent, I wanted Lily to experience at least a tenth, no, a hundredth of the pleasure I had received.

Of course, being a virgin just moments ago, I had no idea how to make her feel good.

"So, Lily, can you tell me how I can make you feel good?"

◇◇◇◇◇◇◇◇◇◇

"Hngh..."

"Sorry, did that hurt?"

"Yeah, a little."

I sat Lily on my lap, playing with her daifuku-sized boobs. I thought I was gently touching them, but somehow, I seemed to have become more forceful.

When seen directly from the front, Lily's boobs weren't that prominent, but when seen from the side, there was a definite swell. Her nipples were slightly raised, and the color deepened as they extended. They weren't that big, just enough to be cupped by my fingers, but they were soft and supple, clinging to my fingers and remaining captivating no matter how long I touched them. [T/N: To be more precise, a daifuku-sized boobs look like this.]

My erection was still rock hard and pressed against Lily's ass and back. Every time Lily shifted, my penis responded, making it difficult for her to find a comfortable position.

"Is this much fine?"

"Yeah, that's fine."

"Does it feel good?"

"...Not really."

I continued to caress her for a while, but Lily's response remained unchanged. I had figured out the right amount of pressure, so the fact that I could do this without causing her any pain was a significant achievement.

However, I love boobs a lot. I wanted to touch them all over. From now on, while I was captivated by her boobs, it would be sad if Lily remained completely unresponsive.

"Is this better?"

"Mmhn!"

I changed my position and latched onto Lily's boobs. I sucked on it slowly and traced it with my tongue.

Instantly, Lily reacted. She let out a sound, which was a far cry from her previous quiet and passive demeanor. When I pressed my tongue against her nipple and licked it forcefully, Lily squirmed multiple times.

I couldn't tell if it felt good or ticklish, but her inability to suppress her moans turned me on so much. I focused solely on licking and nibbling at Lily's boobs.

"Lily, is this painful?"

"Mhnm... I'm fine."

After savoring her with saliva until things got quite wet, I finally released my mouth from her boobs. Because I didn't switch the boob I was sucking on halfway through, there were several hickeys left only on the left boob. The before-and-after of the left and right boobs looked somewhat erotic, in an odd way.

Upon closer inspection, only the left nipple was standing erect. Perhaps she felt something significant.

"I'm sorry, Lily, I got too carried away."

"No, it's okay. It didn't hurt."

"That's good. So, did it feel good?"

"I don't know. It was kind of... ticklish."

Her comment was a bit ambiguous, but I thought her response was not bad. I wasn't sure if Lily herself was aware of it, but towards the end, she was pressing my head against her chest. At least, it wasn't a bad stimulus. Someday, making her climax with her boobs might not be just a dream... or so it felt.

As much as I wanted to continue playing with her right boob, my attention shifted to another part of Lily's body.

"Lily, is it okay if I touch here too?"

Saying that, I placed my hand on Lily's lower abdomen. Of course, I didn't mean to touch her abdomen, but rather the area below that.

I wanted to see it, I wanted to touch it. During the first time, my mind was occupied with the act of penetration, and I didn't have many memories of it. When Lily saw my heated gaze, she nodded slowly.

"Is this okay?"

"Yeah, just stay in that position."

Lily, in a position similar to a sitting stretch, toppled over onto her back. She had taken a similar posture during the first time as well, but being scrutinized this closely seemed embarrassing for her. She turned her face away. Her ears were bright red. [T/N: Her pose is basically like this but instead of sitting, she's lying on her back. *the photo is not related to this novel.]

"Lily, if it hurts, you have to tell me."

I had made her cry when I first penetrated her. I couldn't afford to make the same mistake again. Suppressing my desire to tease and experiment, I cautiously touched Lily's vagina.

It was already hot, and engorged. It was much wetter than during our first time. While it wasn't pleasurable for her this time, the effects of the boob stimulation were apparent. Knowing that Lily's body was in a state of sexual arousal, I involuntarily swallowed.

I stimulated her genitals by tracing, poking, and pinching while checking her reactions. Her love juices were slippery, sticking to my fingers and forming strings when I pulled them away. I was certain that penetration would definitely feel pleasurable. 

"Lily, does this feel good?"

"Mm, not really."

"How about this?"

"Mmm, a bit lower, there, that feels good."

I continued caressing her while Lily instructed me. As my actions grew more intense, she didn't show any signs of pain. She started mixing her breaths with small moans, igniting my brain.

"How about this, Lily?"

I inserted a finger into her vagina. I needed to prepare her quickly; I wanted to penetrate her soon.

Her inner walls were incredibly warm. They clung tightly to my finger, and the pleasure of penetration from the first time came rushing back. Mindful of my penis's size, I slowly moved my finger around inside her.

"It's a little painful, but it also feel a bit good."

"How painful is it?"

"Uhm, it's like being lightly pinched."

"In that case, sorry, Lily. Can I insert it inside you now?"

I had intended to pleasure Lily through penetration only after properly preparing her, but I was already at my limit. I had no choice but to give Lily pleasure through direct penetration.

Without waiting for her response, I aligned my erect penis with Lily's entrance. Her slippery love juices were overflowing, and just rubbing against her entrance made me shudder in response. Slowly exerting my weight, I gradually let the tip of my penis slip into her entrance.

"Uooh!"

I unintentionally let out a loud voice. Lily's vaginal walls felt much more pleasurable than the first time I penetrated her. It was hot and slippery, her love juices wrapping around my penis along with the folds of flesh. It felt incredibly pleasant, as if I were soaking in warm water. The deeper I went, the finer the folds became, increasing the stimulation on my penis.

"Haruki, does it feel good?"

"Yeah! Of course!"

Lily asked as if it were a matter of course. I was on the verge of cumming, but I managed to hold back and started moving my hips slowly. Taking my time, I slid my penis inside her, inch by inch, and then withdrew at the same pace.

After repeating this process many times, I gradually grew accustomed to the stimulation. I quickened my pace, but I didn't feel like I was about to cum immediately. It seemed like I would last a while.

"Lily, do you know how I should move to make it feel good?"

"Mm uhm, I want you to rub me around here…"

She said that and pointed to the area just above her mons pubis. It was a substantial load on my penis, but I managed to stimulate the area she specified. Lily's voice became increasingly sweet, but she still seemed to be in some pain.

"Lily, anything else you want me to do?"

"Then, let's kiss."

"Hmm? Okay."

I intended to ask about the rhythm and speed of my movements, but for now, I did as she said and kissed Lily.

I also liked kissing. As our tongues intertwined, Lily's tongue responded eagerly to mine. We tangled, sucked, and explored each other's mouths.

"Mmm... schlurp, ngh... "

Kissing Lily genuinely felt good. It created a sensation where our hearts and bodies seemed to blend together. Lily hadn't shown any resistance to kissing from the beginning. I'd be pleased if she enjoyed kissing as much as I did.

"…Mmm, …smooch… suck, lick... haa... ngh...♡"

If I pressed in forcefully, Lily would gently accept and when I pulled my tongue away, she'd initiate more passionate tongue movements.

At first, both Lily and I felt embarrassed by the sensation of our breaths mingling, so we resorted to breathing through our mouths. But, soon, it became troublesome to keep parting our mouths with each breath, so we shifted to breathing through our noses. Neither of us cared whether our breaths were touching or not; we simply wanted to continue kissing for a long time.

"…Nnn, …slurp♡... smooch... ngh... nghm... smooch♡"

The creaking sound of the bed snapped me back to reality. I had inadvertently increased the intensity of my thrusts. I quickly assessed Lily's condition, but she didn't seem to be in pain at all.

"…Mmnf haah... ♡ Haruki?"

"Lily, is it not hurting?"

"No, it doesn't hurt at all."

"Really?"

"...It's starting to hurt a little. Can we kiss again?"

"...Lily!"

I had been foolish, too focused on external stimuli.

It appeared that what Lily had said about kissing alleviating the discomfort was indeed true. I remembered something about endorphins and oxytocin, the so-called happy hormones.

In essence, when Lily kissed me, any minor discomfort would be forgotten in the blissful mood that followed. My affection for the adorable Lily was overwhelming.

"Lily! I love you!"

"Haruki, me too... ngh... smooch... suck, lick... haa... ngh...♡"

I resumed my thrusts. Maybe due to the influence of the happy hormones, it was the most pleasurable experience I'd had so far. I accelerated my hip movements, prioritizing my own pleasure that I had set aside until now.

"Schlurp... suck, lick... ngh...♡"

The bed was creaking loudly, echoing throughout the room. It seemed fine to overlook this fact for a bit, but this was probably crossing the line.

"...Ngh... smooch♡ ...ngh... haa...♡"

I would likely face the inn owner's anger tomorrow. I should consider changing accommodations. A room with a bath would be nice.

"...Faa...♡, haa...♡...schlurp, ngh♡"

I should let Lily indulge more. I couldn't offer her any more food, but she seemed interested in clothes and accessories.

"Nn...♡ ...schlurp♡ ...smooch... ngh...♡"

What kind of clothes would suit her? A modest dress would probably suit her well. I'd like to see her in Gothic Lolita attire as well.

"...Nhhaa...♡ …ah... nnnh...♡"

I reached my limit quickly. However, there was no need to hold back. From now on, anytime, as much as we wanted, Lily and I could enjoy sex.

"Uoogh!"

I came deep inside Lily. Even though I already came twice before, it seemed my stamina hadn't decreased at all.

My penis trembled as if in spasms, releasing a copious amount of semen that struck against Lily's cervix.

Simultaneously, I thrust my tongue into Lily's mouth, engaging in a tongue-twisting kiss while exchanging a significant amount of saliva. Lily swallowed the saliva with little gulping noises and, intertwining her legs, trapped my semen to fill her vagina.

A sensation as though I had dominated every part of Lily overwhelmed me, and a pleasure so intense it felt as if my consciousness was drifting away enveloped me.

After a prolonged orgasm, even after expelling all the semen, our tongues remained entwined.

My penis, which had been trembling like crazy after cumming, finally calmed down. Lily released her legs from around my waist, her pounding heart gradually returning to its regular rhythm. At last, we separated our tongues that had been entangled for so long.

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