Anal Confession with My Dominant Best Friend

Darío, my best friend from university, was the one who introduced me to the pleasure of pain. We were both adults, already past twenty-five, but we still carried that strange mix of anxiety, exams, poorly paid jobs, and long nights that leave your head full of noise.

Darío had a strange way of calming himself. When stress overwhelmed him, he sought out an intense physical sensation that forced him back into his body. At first, he frightened me. I didn’t want to hurt myself the way he had before; I didn’t want wounds or marks I’d later have to explain. But I did discover that controlled pain had an effect on me: it put me in order from the inside out.

It started with my nipples. One afternoon in his room, he saw me rubbing my chest through my blouse and asked whether they hurt. I told him no, that I liked feeling pressure there when I was nervous. Darío gave a faint smile, as if he had just found a door I myself hadn’t known was open.

“Let me try,” he said.

There was no ceremony. He unbuttoned my blouse with clumsy hands, lowered my bra, and took one nipple between his fingers. At first he squeezed slowly, gauging my reaction. Then he pinched harder. The pain rose through my chest like a hot current and left me breathless.

“Like that,” I whispered, embarrassed by how much I liked it.

From then on, whenever stress tightened around my throat, I ended up in his room with my skirt raised or my blouse open, letting him bite my nipples until they were hard, red, and sensitive. We weren’t a couple. We were friends, I kept repeating to myself, even though every bite of his made my legs grow wet and every silence afterward brought us closer to something neither of us named.

One Friday he arrived with a small box wrapped in silver paper. He set it on his bed and looked at me with that calm of his that always seemed to conceal a command.

“I brought you another way to feel,” he said.

Inside was a small metal plug, heavy for its size, with a pink heart-shaped stone at the base. I took it between my fingers, and the chill of the metal made me shiver. I had never put anything in my ass. The idea frightened me and, at the same time, turned me on so clearly that I had to cross my legs.

“Do you want to try it?” he asked.

I nodded before I could invent a dignified answer. We locked ourselves in his room. His grandmother was in the living room watching television, which made everything feel more forbidden, even though no one was coming in or out. I took off my underwear, leaned against the bed, and lifted my skirt. I felt his gaze on my buttocks before I felt his fingers.

Darío couldn’t find any lubricant and returned from the kitchen with some butter in a container. I laughed nervously, a silly laugh that was cut short when he spread my buttocks and rubbed the metal against my vagina. The cold made me moan softly.

“It’s not supposed to go there,” I said, trying to sound calm.

“I know,” he replied. “But you liked it.”

I was embarrassed because it was true. He ran the plug over my wetness and then brought it to my ass. I felt the rounded tip pressing, insistent. I opened myself with my fingers, gave him permission with a roll of my hips, and bit the bedspread when he began to push.

It hurt. Not like a blow, but like a slow invasion, a pressure splitting me in two from a tiny point. Darío moved slowly at first, but when the wider rim resisted, he placed one hand on my lower back and pushed all at once. The plug slid in with a dry burn that tore a muffled moan from me.

I remained on all fours, trembling, with the pink heart showing between my buttocks. I felt it inside me with every breath. It didn’t fill me much, but my body recognized it as something foreign and squeezed it involuntarily.

“Look at you,” Darío said, running a finger around the base. “So serious on the outside, with this stuck in your ass.”

Those words burned more than the metal. I lowered my face to the pillow and squeezed my thighs together. I wanted to deny it, to pretend to be offended, but I was wet.

Afterward we ate with his grandmother as if nothing had happened. I sat at the table, answering simple questions, while the plug pressed inside me every time I shifted position. Darío watched me from across the table and smiled faintly. He knew exactly what I was feeling.

When we returned to the room, I tried to take it out myself and couldn’t. I grew nervous. Darío knelt behind me, told me to breathe, and carefully took hold of the base. He pulled slowly, but the pain still bent my back. When it came out, I felt a hot emptiness and a sharp pang that made me close my eyes.

“Now you have another way to calm yourself,” he said, washing the plug in the bathroom.

I didn’t answer. My face was burning and my legs were weak. The worst part was that I already wanted to do it again.

***

A few weeks later he told me he was leaving. He had found a job in another city and had to move in with his mother while he looked for an apartment. He said it as if it were an ordinary fact, but it landed in my stomach like a stone.

That last Friday I waited for him outside campus with my nipples swollen from pinching them so much during my final exams. I had the plug in my bag and a little bottle of baby oil wrapped in a scarf. I had decided to give him something he couldn’t forget. And although I was afraid to admit it, I wanted to keep one of his marks on me too.

We walked to his house almost without speaking. His grandmother wasn’t there. His room was filled with open boxes, folded clothes, and a half-packed suitcase. That farewell disorder made me sad and horny at the same time.

I came up behind him, bit his earlobe, and placed his hands on my buttocks.

“I want you to fuck my ass before you leave,” I whispered in his ear.

Darío went still. I felt his fingers sink into my skirt, gripping the fabric and the flesh beneath it.

“Are you sure?”

“Yes. I want it to be you.”

He spun me around and kissed me with a force he had never used before. He bit my lip until I cried out, and that cry changed his expression. He was no longer my curious friend. There was something harder in his eyes, an authority that made me obey before he said a word.

He sat me on the desk and spread my legs. He pushed my skirt up to my waist, took off my underwear, and left it on the chair. I was unbuttoning my blouse with clumsy fingers while he poured oil into his hand and rubbed it over my vagina, my swollen lips, and my ass, still tense at the memory of the plug.

“You came prepared,” he said. “You like to play calm, but you’re a pervert.”

“I like it when you tell me that.”

He grabbed my hair, not to truly hurt me, but to force me to look at him. With his other hand he brought the plug to my ass. The tip went in more easily than the first time, but the pain was still there, bright and precise. I bit my tongue and kept my eyes open.

“Don’t close your eyes,” he ordered.

He pushed until the pink heart was pressed against my skin. Then he put two fingers in my vagina. I was so wet they slid in with an obscene sound. He began moving them quickly, curling them inward, while the plug opened me from behind. The combination made me clumsy. My legs trembled on the edge of the desk, and my hands searched for something to hold on to.

“Look at what you’re becoming,” he said. “It hurts you, and you’re still soaking wet.”

All I could do was moan. He took one nipple between his teeth and then bit it harder. The pain pierced my chest and went straight down to my belly. I came like that, without warning, squeezing his fingers with my vagina, my ass clenched around the plug, my mouth open against his shoulder so I wouldn’t scream.

Darío stepped away and unzipped his fly. It was the first time I had seen his cock. Big, hard, heavy in his hand. It frightened me. I didn’t hide it.

“It’s going to hurt,” he said.

“That’s why I came.”

He put on a condom, laid me on the bed, and positioned himself between my legs. First he penetrated my vagina. He went all the way in with a slow thrust that made me arch my back. I was already sensitive from my orgasm, and every movement drew louder moans from me. He covered my mouth with his hand.

“Quiet. If my grandmother comes back, I don’t want her to hear you.”

I nodded against his palm. He fucked me like that for a few minutes, hard, stretching me with his cock, getting me used to his size. I scratched his arms and moved my hips, seeking more, but I knew that was only the beginning.

When he pulled out of my vagina, I felt cold. Darío turned me facedown, lifted my hips, and pulled the plug out with a slow tug. The burning returned immediately. He spread my buttocks with both hands and placed the tip of his cock against my ass.

“Don’t stop looking at me,” he said.

I turned my head on the pillow to see him. He pushed lightly, and my body closed around him. It hurt more than the plug, much more. The tip wanted to enter and I felt that there was no room, that he was going to split me open. Darío didn’t move quickly at first; he pressed, waited, and pressed again. I breathed as best I could, my face buried in the pillow.

“Open your ass for me,” he murmured.

I obeyed with my body, pushing back even though it burned. The head of his cock crossed the first ring with a brutal stab. I moaned into the fabric, almost crying. Darío held me by the waist and continued entering inch by inch. Every advance filled me with pain and a hot humiliation that made me wet again.

When he was finally inside, he remained still. I felt his entire cock buried in my ass, hard and enormous, forcing me to open around him. He pinched my nipples from behind, one in each hand, and the pain blended together until I no longer knew which part of me burned most.

“This is how I wanted to remember you,” he said. “Open, trembling, and mine.”

He began to move. At first the thrusts were short, almost cruel in their slowness. He went in and out without withdrawing completely, stretching me and making me feel every brush of him. I bit the pillow and made muffled sounds. The burning was intense, but beneath it was pleasure, a filthy, deep current I was ashamed to acknowledge.

Darío noticed. He grabbed my hips and began to pump harder. Every thrust pushed me against the mattress. My buttocks slapped against his pelvis, and the dry sound filled the room. I cried a little, not from regret but from excess. It was too much pain, too much cock, too much desire accumulated over all those months of pretending we were only friends.

“Tell me you like it,” he demanded.

“I like it,” I said into the pillow.

“Louder.”

“I like you fucking my ass.”

That turned him on. He lifted my hips higher and penetrated me with deep blows, not letting me escape. I gripped the sheets while I felt my ass yield, burning as it received him all the way. Every time I tried to close my legs, he spread them with his knees and kept going.

Then he pulled out suddenly. He left me empty and throbbing, and turned me onto my back. His eyes were dark and his breathing ragged. He thrust into my vagina again in one motion, and the change tore a freer moan from me. By then it wasn’t only pain. It was direct, wet pleasure, a delicious friction after so much tension.

He fucked me hard, gripping my thighs and watching my body take every thrust. I begged him for more without thinking. He gave me more. My second orgasm arrived in a violent convulsion, my nails buried in his back and my nipples burning from everything he had done to them. Darío pulled out at the last moment, removed the condom, and came over my buttocks, leaving my skin hot and sticky.

He lay down beside me, exhausted. Neither of us spoke for a while. I could feel my ass swollen and sensitive, as if every pulse reminded me of what had just happened. I also felt a soft sadness, because I knew that getting dressed would begin the farewell.

I cleaned myself, put on my blouse, and looked for my underwear. Darío had it in his hand.

“Leave it with me,” he said. “So I can remember.”

I didn’t argue. I left his house with my skirt straightened, my legs weak, and my ass aching. I left the plug and the oil behind in his room, although sometimes I think it wasn’t really an accident.

Darío left two days later. Years passed without our seeing each other. We spoke little, then not at all. I continued using clamps and suction toys on my nipples whenever work stress overwhelmed me, and more than once I thought about that pink heart hidden among his things.

A few months ago he wrote to me again. He didn’t begin with nostalgia or apologies. He only asked whether I still liked pain. It took me an hour to reply, but the truth had already been in my body from the very first second.

Last week a package arrived at my apartment. Inside were a bottle of oil and a metal plug with a pink heart, just like the first one, but much larger. There was also a note in his handwriting: “For our future encounter.”

I held it in my hand for a long time. It weighed more than I remembered. It frightened me. It aroused me. And as I put it away in my nightstand drawer, I knew that if Darío knocked on my door, I would open it.