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Featured: True Stories of First Gay Anal Sex — Editors’ Pick

Featured: True Stories of First Gay Anal Sex — Editors’ Pick

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I never planned to tell anyone about that night, but some memories demand to be spoken. I was twenty-three, living in a cramped apartment above a coffee shop in Portland, still telling myself I was mostly straight even though the curiosity had been gnawing at me for years. Mark was the one who finally pulled the thread loose. He was thirty, quiet, with a slow smile and hands that looked like they could hold anything steady. We had been circling each other for weeks through mutual friends, trading glances that lasted a second too long.

The evening it happened, we ended up alone in his studio after everyone else left. The rain was steady against the windows, and the only light came from a single lamp by the bed. We talked for hours, voices low, until the space between us disappeared. When he kissed me, it was careful at first, then deeper, his tongue sliding against mine with a hunger that made my knees weak. My cock was already hard, pressing against my jeans, and I felt his through the fabric, thick and insistent.

We undressed each other slowly.

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I remember the exact moment my fingers wrapped around his shaft for the first time, how hot and heavy it felt, the way the head flared slightly and a bead of pre-cum welled up. He groaned when I stroked him, and the sound went straight to my gut. I had never touched another man this way, but my body knew what it wanted.

Mark guided me onto the bed on my stomach, his palm warm between my shoulder blades. Tell me if you want to stop, he said, voice rough. I nodded, face pressed into the pillow, heart hammering. He spread my cheeks with both hands, and the first touch of his tongue against my hole made me gasp. It was wet, soft, circling and pressing until I was pushing back against his mouth, desperate for more. He licked me open for what felt like forever, saliva running down my crack, his fingers eventually joining, one slick digit sliding inside while his tongue worked around it.

By the time he reached for the lube, I was trembling. The cool gel against my skin made me shiver, and then his finger pushed in deeper, crooking to find that spot that made my cock twitch against the sheets. He added a second finger, scissoring gently, stretching me while he whispered how tight I felt, how beautiful I looked opening for him. The burn was there, but it melted into something hotter, something that made me moan into the pillow and rock back onto his hand.

When he finally positioned himself behind me, the blunt head of his cock pressing against my entrance, I held my breath. He went slow, so slow, one hand on my hip, the other stroking my lower back. Breathe, he murmured. I did, and the pressure built until the head slipped past the ring of muscle. The stretch was intense, almost too much, a deep ache that bordered on pain, but he paused, letting me adjust. Inch by inch he sank into me, filling me until his hips met my ass and I felt completely taken.

The fullness was overwhelming. Every nerve seemed lit up. When he started to move, shallow thrusts at first, the friction sent sparks through me. My own cock rubbed against the mattress with each push, leaking steadily. Mark leaned over me, chest to my back, and reached around to stroke me in time with his thrusts. You feel so good, he breathed against my ear. So fucking tight around me.

I lost words after that. The rhythm built gradually, his cock sliding almost all the way out before sinking deep again, hitting that same spot inside me that made my vision blur. The initial discomfort had vanished, replaced by a rolling pleasure that started low in my belly and spread outward. I pushed back to meet him, greedy for every inch. Sweat slicked our skin. The room filled with the wet sound of his cock moving in and out of me, the slap of skin, our ragged breathing.

When he angled his hips differently, the head of his cock dragged directly over my prostate with every stroke. I cried out, the sound raw, and came hard without touching myself, my cock pulsing against the sheets in long, shuddering waves. My hole clenched around him, and that was enough to push him over. He buried himself deep, groaning my name as he filled me, hot pulses I could feel deep inside.

We stayed like that for a while, him softening inside me, his weight a comforting pressure. When he finally eased out, I felt the slow trickle of his cum, and the sensation made me shiver again. He cleaned me gently with a warm cloth, then pulled me into his arms. We didnt talk much afterward, just lay there listening to the rain, my body sore in the best way, already wondering when we could do it again.

That first time didnt make me instantly certain of anything, but it opened a door I had kept locked. The memory still surfaces sometimes, the exact stretch, the heat, the way surrender felt like coming home. I tell it now because some truths deserve to be spoken out loud, even years later.

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