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Chapter 37 Our First Challenge Together

Our First Challenge Together

Maybe because the next day was New Year’s Eve, the subway was relatively empty during our commute and we were able to get seats.

We held hands the whole time, both while moving and while sitting. Iroha-san was smiling all the time, looking so happy. Seeing her like that, I was happy too, and I could tell that my face was softening.

But Iroha-san was always looking at something while talking.

When we arrived at our destination, the restaurant was crowded and all the table seats were full, so we were directed to a counter seat.

However, we were lucky enough to be able to sit down without having to wait.

While leaning our shoulders together and looking at the menu, Iroha-san ordered a Mont Blanc and milk tea, and I ordered a Kiwi roll cake and cafe au lait.

While we waited for the waiter to leave, we continued to chat, but Iroha-san kept looking at something.

When the cakes were brought, Iroha-san’s eyes lit up, and she exclaimed several times, “It looks so delicious!” and took several pictures of the Mont Blanc with her smartphone.

The Mont Blanc in this restaurant has a lot of cream and is quite impressive.

It looks like a bald head? Its size is huge, and it’s piled high with chestnut cream. I took two pictures of the cake and Iroha-san with my smartphone, but it’s about the same size as Iroha-san’s face.

Iroha-san ate it all.

I only had one bite to taste, but really, just one.

For someone so small, she loves sweets so much.

She was smiling the whole time and seemed really happy, so even though it was a day late, it was totally worth it to take her out to celebrate her birthday.

Then, after we finished eating and left the restaurant, we went back to my place after window shopping, but even during that time, Iroha-san was smiling happily but looking at something.

So when we got home, I turned on the heater, got dressed, went to the kotatsu, and while taking a break to drink tea, I gave her some advice.

By the way, in the kotatsu, we sit side by side and close together.

It’s just like our current loving distance.

“I want to give Iroha-san some advice.”

“Yes? What is it?”

“Iroha-san, today you’re too aware of my…You’ve been looking at that the whole time….”

“No! I wasn’t looking!”

Before I could finish, she denied it.

“No, you saw it, didn’t you?”

“I didn’t!”

“The fact that you are getting so worked up is suspicious.”

“I’m not getting all worked up, and it’s not suspicious!”

They say that Columbus insisted that America was India until his death, I wonder if it was something like this.

When I looked at her suspiciously, Iroha-san quickly looked away.

“Are you worried that it’s getting hard again?”

“Just a little, but! It’s only for academic purposes! I just learned about the mechanics of the male body, so isn’t it natural to be curious?”

“Oh, I think you’re being honest. I’m not saying it’s completely wrong. But it’s one thing to do it at home; it’s inappropriate to keep staring at a man’s thing during a date.”

“Ugh! It’s embarrassing….”

Iroha-san, perhaps overcome with embarrassment, buried her face in the kotatsu, her ears turning bright red.

I found her so cute and amusing, but I didn’t want to tease her, so I decided to comfort her.

“Well, you’ve just started studying, so it’s natural to be curious. After I kissed Iroha-san, I wanted to kiss her more and more. It’s the same thing, isn’t it?”

“Ugh, please don’t say that….”

“So tonight we’ll do some practical training.”

“Practical, you say?”

While keeping her face down, Iroha-san looked up at me.

“Yes. You didn’t see it directly, did you? Shall I show you after my bath?”

“R-Really?”

Iroha-san’s face lit up when she heard my suggestion.

She really likes the idea, doesn’t she?

“Yeah, well, if we’re going to do it at some point, we’re going to have to show it to each other at some point. If I’m always embarrassed, I won’t be able to move forward.”

“I see… I understand. I can’t be embarrassed either. Let’s look at each other tonight. Let’s carefully observe and learn about the differences between male and female bodies.”

Iroha-san pushed up her glasses with her right index finger, regained her composure, and began to speak in a serious tone.

“Eh!? Iroha-san will show me tonight too?!”

“Yes. Since I was the one who suggested that we study together, it’s only fair. Besides, if we’re both n🬀🬀ed, we might feel a little less embarrassed, don’t you think?”

"Yes… I think you’re right."

So the second night, Iroha-san stayed at my place.

We undressed and exposed ourselves to each other, looking at each other and touching each other a little.


The morning of the third day.

When I woke up, just like yesterday morning, Iroha-san was fast asleep with her head on my arm.

But we weren’t n🬀🬀ed.

It was too cold and embarrassing, so we slept in our pajamas.

And unfortunately, as soon as I woke up and was surrounded by Iroha-san’s scent and felt the warmth of her body and her softness, I started to get excited again.

Last night, before I went to sleep, I locked myself in the bathroom and masturbated.

As expected, last night the stimulation was too strong, and I couldn’t stop myself.

I had told Iroha-san before, “I can’t control myself, so I’m going to relieve myself in the bathroom,” and she agreed and said, “I’m sorry,” so I think she understood that it was an inevitable natural phenomenon. I’ve been thinking about it since the day before yesterday.

And now I’m getting excited again.

I mean, aren’t I excited?

This isn’t just morning wood.

I used to be so afraid of s🬀x, but now I’m aroused by Iroha-san.

Maybe it’s a reaction to what’s happened so far, but I feel a little too energetic.

Somehow I feel like we could do it soon.

No, even if I think I’m ready, Iroha-san might still be unsure.

After what happened yesterday, there’s no doubt that she has an extraordinary interest in the male body.

But that doesn’t mean we’re going to do it right away.

After all, it’s painful for women.

But this could be an opportunity.

Even pain is something you have to overcome at some point.

If I continue with the flow of the last two days, I might be able to have good s🬀x.

I might even be able to have a successful s🬀x.

So after Iroha-san woke up and I gave her a good morning kiss, I proposed.

At first, Iroha seemed hesitant, but when I showed her my hard thing and said, “This is what it looks like now,” she stood up and said, “I will prepare a safety,” and came back with a c🬀🬀dom and put it on it.

By the way, it took a while to put it on, but after some back and forth, she managed to get it on.


And… as expected, our first real challenge didn’t go well.

Seeing Iroha-san’s painful expression, I gave up trying to continue.

I tried to do it while repeating “gently and carefully!” over and over in my head, but I couldn’t do it well.

However, Iroha-san, who must’ve been in great pain, was much more positive than I was. She said, “It’s natural that we can’t do it perfectly right away because we’re beginners. But think about it; this is a big step for us! Let’s try again tonight. I’m sure I’ll get used to the pain too.” Then she kissed me for the first time to cheer me up.

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