Chapter 1 — I Want to Fuck a Woman, But I Also Want to Fuck a Man

It wasn’t that long ago. We’d been together for a while, and by then we’d tried nearly every position and act imaginable.

We hadn’t done anything extreme, but since he was just as twisted as I was, the more time passed, the more we both craved something fresher, something new.

We had this small dildo we used to play with, and he loved tormenting me with it. It wasn’t huge, and the vibration wasn’t bad at all—so for me, it brought pleasure without much pain.

Sometimes, even more than his cock, his mouth, or his hands. But then, one day, curiosity hit me. I had plenty of gay friends, and I’d watched more than my share of intense Western porn.

If men can clearly feel sexual and psychological pleasure through anal stimulation, why haven’t we ever tried it? The thought hit me suddenly, and that very night, I said it straight out.

“I want to try something.”

“What?”

“I want to fuck your ass with that dildo.”

I wasn’t joking. I said it dead seriously. He froze, unable to answer. Realizing I might’ve come on too strong, I started coaxing him with a sweetness I never used, trying to soften him up.

“Men do feel it there, you know. Just once. Let’s try it just once.”

“No! I’m not gay!”

“Hey, do only gay guys do anal? Plenty of straight guys do it too!”

“Ugh… still, no.”

“Come on. Girls do anal all the time. You see it in pornos. Why can’t a guy?”

“It’s weird!!!” He finally screamed it out. “No! It hurts! It’s weird!!!”

“If it hurts, I’ll pull out right away. I promise, seriously!”

“…Why do we even have to do this…”

“It’s not like I’m asking for forever. Just once. Just one time. I’ll put it in and pull it right back out. Just once.”

Who would’ve thought I’d be the one saying “put it in and pull it out”? Maybe I had too much testosterone in me, but as I kept repeating those words to convince him, even the act of persuading him became a kind of foreplay for me.

He realized he couldn’t win against my stubbornness. Finally, with a deep, exhausted sigh, he muttered, “Fine… just once,” and gave in.

After showering, we lay side by side on the bed. He glared at me like he wanted to murder me, his eyes burning with resentment as I clutched the dildo tightly in both hands, staring at him with wide, eager eyes. Then, with the deepest, most human sigh imaginable, he turned over and got on all fours.

“No, you need to do the cat pose.”

“What’s that?”

“You know, the one I do when you’re behind me.”

Trying to ease his tension, I spoke in a deliberately sultry voice. Normally, he’d have smirked at that, but now his face was blank as he lifted his hips and raised his upper body.

Ah, the strange thrill I felt then! Seeing a strong, fully grown man, cock dangling beneath him, exposing his bare anus so openly in front of me—it was indescribable. Was it tension from awkwardness? Was it something strange? Or just unfamiliarity? Whatever it was, my heart began pounding wildly.

“I’ll go slow. Very gently.”

I poured a generous amount of lube I’d prepared earlier between his plump ass cheeks. He flinched, his hips jerking involuntarily. Once the clear, sticky liquid had thoroughly coated his opening, I carefully brought the dildo close.

“It already feels like it hurts.”

“Stop whining. I haven’t even put it in yet.”

I said it firmly, then slowly applied pressure. He started groaning, “Ugh… ahh…” And then, I experienced something astonishing.

His anus began sucking the dildo in like a black hole, pulling it in with surprising force. Ah, so this is why men love anal, I thought cautiously.

“Does it hurt?”

I asked after about half of the 15cm-long dildo had slipped inside. When he didn’t answer, I started a gentle piston motion. And then, I was shocked all over again.

“Mmm… c-can you… go a little harder?”

What the hell?! (Not judging gay guys—I have plenty of gay friends. Just a joke.) He was actually asking me to go harder!

I smirked slightly and increased the speed and force. His groans shifted—“Ah… ah…”—from pain to excitement, gradually transforming.

We stopped speaking altogether. I focused on thrusting, and he on feeling. Wanting to give him even greater pleasure, I reached around with my other hand and started stroking his cock.

“Ugh… stop… stop…”

When I touched his rock-hard dick, he almost sobbed, but I didn’t stop. I kept going, swinging my wrist like it might break, using every bit of my barely existent biceps to keep the motion going.

“Agh!”

Suddenly, he screamed, springing forward like a released coil. Startled by his sudden reaction, I panicked—had I hurt him?—and quickly pulled out the soaked dildo to check. Instead of blood, thick, glistening liquid dripped heavily from it. Lube? Or something else?

“Why? Are you okay?”

“Ah… uh… hah…”

He kept making strange, unexplainable sounds. A sudden wave of guilt I’d never felt before crashed over me, and I pulled him tightly into my arms.

“I’m scared…”

“Scared of what? Did it hurt too much? I’m sorry…”

“No… not that…”

“Then what? Tell me. It’s okay.”

“It’s… it’s too good… too good… it scares me.”

After that night, I never brought it up again. For days afterward, he complained to me about feeling confused, like his sense of identity was unraveling.

Eventually, we stopped seeing each other for other reasons. But since then, with every man I’ve dated, I’ve asked—just once—if I could do the same. So far, I’ve been turned down every time.