Stealing Spree

As our kiss deepened, I resolved myself to finish it in one thrust.

With my cock lodged at that small entrance to her narrow and unexplored cave, I thrust my length in one strong push, tearing away the thin film that tried to block my way, squeezing inside the narrow pathway to her depths...

Tears instantly stained Nami’s eyes as a pained expression filled her face along with her hands strongly tugging at my hair. Furthermore, because of our deep kiss, Nami also couldn’t help but bite down on my lips. She gritted her teeth as a means to endure the pain that coursed through her whole body.

Compared to the pain that she’s currently enduring, the pain I felt from those two instances was nowhere close to it.

“Ugghh... I-it hurts, Ruu.” Nami painfully whispered as I saw her forehead creased from the pain.

With my cock firmly thrust up to its base deep inside her, Nami’s lower body kept on convulsing as she involuntarily tried to squirm out of it to escape the pain she was feeling.

I released her legs from my hold which immediately enclosed around my back. Despite the pain that she’s feeling at the moment as well as her body’s involuntary reaction from it, Nami also didn’t want me to pull out.

Following that, I slipped my arms beneath her head and back, hugging her tightly.

“Un. I told you, didn’t I? It’ll hurt a lot. But soon, it’ll ease up. I did it in one thrust so it’s swift but truly painful. I won’t move yet and I’ll keep holding you like this. Feel it clearly... our connection.”

I caressed her face, trying to ease up her pain even just slightly. Unfortunately, I am aware that it’s close to impossible.

Nonetheless, Nami forced a smile to not let me worry about her.

From down below, I could feel her insides tightly clinging on me as it also tried to push my cock out of her. However, with the vaginal fluids she produced, it’s more pleasurable than painful for me. Unfortunately, that’s not the case for Nami.

Although there were times where I used my fingers to pleasure her, it couldn’t reach her depths. What she’s feeling at the moment was like being impaled by a foreign object. Moreover, with my blood focusing on my cock to make it that erect, it’s scorching hot.

A little movement from me was enough to evoke a reaction from Nami, be it pain or pleasure, that’s kinda foreign to her yet given how sensitive her vaginal walls are.

After a while, Nami bravely looked down to see the place where we’re connected. Seeing how there’s a slight bulge on her navel, Nami was slightly amazed. “You’re really inside me... Ruu.”

“Un. Yes, I am. And you’re squeezing me tight. It felt so good for me.”

Slowly the pain was gradually easing up for her. Nonetheless, it would persist even after we finished.

“R-really?”

“Look at my face. What do you see?”

“... You’re red. Ruu. What is this? It’s painful but...” She placed her hand on top of that bulge and rubbed it. “... I want to see you move. Show me how you do it.”

“Alright. I’ll start moving then. Hold onto me. Don’t be afraid, I’ll keep holding you. It’s painful for now but once you get used to it...”

“... It will feel good to me. Is that what happened with Saki?” Nami finished my words and even threw a question.

I always tried not to talk about other girls when I’m with them but in this case, she brought it up herself.

“Yes. It’s also painful for her when I did it. And... I wasn’t that gentle with her. Fortunately, she didn’t blame me for it.”

Back then I was so lost with my lust that I only paused for a while before I began moving after tearing her hymen. I felt a little guilty for that, that’s why when we did it in her room, I gently did it for her.

“I see... Then Ruu, don’t worry about me. You warned me not just once. I invited you here for this so I prepared my heart for this. Let me feel you.”

This girl, by mentioning Saki, lit up her slight jealousy to give her the determination she needed. Perhaps in her mind, she’s thinking that if Saki could endure it, why couldn’t she?

Naturally, I wouldn’t mention that to her so... to answer to that determination, I moved my hips, pulling my cock slightly before thrusting it once and in full force.

Her twin peaks trembled and her breathing turned ragged.

And like I expected, Nami’s insides instantly constricted, squeezing me tightly. And even though Nami’s moan escaped her lips, the pain was still written on her face.

However, still following what she wanted to happen, I moved once more, burying my cock deep inside her. By now, she’s slowly being molded to my shape.

And while I’m at it, I watched her reactions carefully to find her sensitive spots.

At each thrust of my hips, my cock would be squeezed tightly but at the same time, Nami’s painful expression was slowly changing to her face when I was eating her out. Her beautiful face was sexily contorted from pain and pleasure.

When she reached in for another kiss, she would whisper her love for me along with how much she waited for this night.

And a few minutes into our intercourse, the occasional thrusting of my hips gradually quickened. Pushing my way through her extremely narrow insides that’s either trying to push me out or suck me in, Nami slowly but surely eased up.

At this point, I already raised my body and held her by her hips. With the pillow supporting her back, I kneeled in front of her as my hips continuously thrust forward and backward, plunging in her depths.

Watching the girl clawing and gripping at her bedsheet, I couldn’t help but admire how sexy she looked. Her disheveled hair, her extremely flushed face and her sweaty body. At times I would lean down to suck on her nipples or lock her in a kiss, heightening the pleasure for her.

Even though she’s still not accustomed to it, Nami’s moans and the sloppy sounds being produced by our connection were the only noises filling our ears.

Since this was her first time, I decided to finish without changing our position. However, I was wrong.

Perhaps frustrated that she couldn’t reach me with her hands when she’s about to cum, Nami lifted her body to cling onto me as she forcefully pulled me down with her, returning us to the same missionary position.

Her arms and legs then locked me in while her lips prevented me from pulling away.

“S-stay like this, Ruu.” She begged.

And with those words, I surrendered.

A few thrusts later, Nami’s body shuddered from the pleasure as her love juices spilled on her bed along with the blood from her hymen.

As pleasure superseded the pain, Nami reached her first climax.

Seeing that it’s a success, I smiled and let her rest for a moment. And once I resumed plunging and grinding her sensitive depths, Nami also resumed her uncontrollable moans.

“Ahn... Ahhh... Ruu...!”

With my name mixed in with those moaning sounds produced by her, I eagerly quickened my pace as I aimed to finally finish with her.

Five minutes later, I felt Nami’s lower body trembling uncontrollably for the second time as the pleasure she felt peaked once more. A few seconds after that, I did one last thrust as I buried my cock deeply before releasing what I accumulated inside Nami.

I tried pulling out but Nami just shook her head, preventing me from doing that.

After a few more twitches of my cock and a few more squeeze by her vaginal walls, I pulled it out of her as I laid down next to her.

But instead of laying on my back, I pulled on her arm, enclosing her in my embrace.

The mix of my semen and her love juices was flowing out of her at the moment but... that’s irrelevant for now as Nami and I snuggled to each other, feeling each other’s heartbeat.

“You filled me up.” After a while, Nami seductively whispered as I felt her hand lovingly brushing my hair. “I love you, Ruu.”

“Mhm... I love you too, Nami. What if we sleep like this?”

“Not what if, let’s sleep like this... with you next to me” Nami partly jokingly and partly seriously said before continuing as the red of her face hadn’t faded yet. “It still hurts but when I get used to your... thick length grinding inside me... I felt really good.”

“If it still hurts, do you remember what you said earlier?”

“Y-you pervert! I did say that but can you still get it up?”

“Give me 30 minutes.”

And with that answer of mine, Nami giggled and turned into a burst of clear laughter. Although I’m not joking with that statement, it probably came off like that for her.

Once we rested enough, Nami picked up her bag and brought out the box of tissues she bought earlier. Wiping our sweat and most importantly, that part of hers that’s still leaking.

Right. She prepared for this. I also bought a box of condoms. However, I actually forgot I did that... I already got too used to doing it raw. It’s dangerous, true... But with those pills, it hadn’t failed me yet.

“Ruu, let’s take a bath...” After dumping the tissues into her trash bin, Nami then declared and without waiting for me to respond, she grabbed onto my hand and pulled me up. “... together.”