Gay Sex Stories
Editors’ Pick: Gay Anal Sex First Time: The Night I Finally Gave In — Featured

Editors’ Pick: Gay Anal Sex First Time: The Night I Finally Gave In — Featured

Discover “Editors’ Pick: Gay Anal Sex First Time: The Night I Finally Gave In — Featured” through this featured story. The page keeps the focus on the central topic while providing clear routes to related categories, tags, and recommendations across the site. Visit the complete entry for every available detail and continue browsing other carefully chosen posts from the same collection.

I had been thinking about it for months, the way the thought would hit me late at night when my hand was already wrapped around my cock. I was twenty-three, straight by every label Id ever used, but the fantasy kept coming back stronger: another man pushing into me, stretching me open, filling me until I couldnt think straight. When I finally messaged Derek on the app, my fingers shook. He was older, thirty-one, calm in his texts, and he didnt push. We met for a drink first, then another. The third time he invited me to his apartment I said yes without pretending I was only coming over to watch a movie.

His place smelled like clean laundry and something darker, like leather. We kissed on the couch before I could overthink it. His mouth was firmer than any womans Id kissed, his tongue direct, his hand already sliding under my shirt to feel the heat of my skin. I was hard so fast it embarrassed me. He noticed and laughed low against my neck. Been thinking about this, havent you? I nodded. Words felt too big.

He took his time undressing me, then himself. His body was solid, a little hairy across the chest, cock thick and already leaking when he freed it. I touched him first, curious, wrapping my fingers around the heat and weight. He let me explore, then guided my hand lower, showing me how he liked to be stroked. When he reached between my cheeks and pressed a fingertip against my hole I tensed, but he didnt push inside yet. He just rubbed slow circles until I started rocking back against him without meaning to.

Bed, he said. I followed.

He had lube and towels ready. That small detail made me feel both cared for and filthy at the same time. I lay on my stomach first, face turned to the side so I could breathe. Derek knelt between my legs and spread my ass with both hands, looking at me openly. Pretty, he murmured, and then his tongue was there, wet and insistent, licking over my hole. The sensation shocked me. I moaned into the pillow, hips lifting on their own. He licked and sucked until I was pushing back, begging without words.

One slick finger pressed in. It burned, but the burn turned into something hotter as he worked it deeper, crooking it until he found the spot that made my cock twitch against the sheets. I was leaking steadily. He added a second finger, scissoring me open, talking the whole time in that low voice. Youre tight. Gonna feel so good around my cock. You want that, dont you? Want me to fuck this virgin hole? I answered with a broken sound and pushed back harder.

When he finally rolled me onto my back and knelt between my thighs, I was shaking. He slicked his cock thickly, then pressed the blunt head against me. Breathe, he said. Push out a little. The pressure built and built until the head popped inside. I gasped at the stretch, the burn flaring sharp. He stayed still, letting me adjust, one hand stroking my cock to keep me hard. Inch by inch he sank deeper. Every time I thought I couldnt take more, my body opened a little further until his hips met my ass and he was all the way inside.

We stayed like that for a long minute, both of us breathing hard. I felt split open, full in a way Id never imagined. When he started to move, slow shallow thrusts, the burn eased into a deep, rolling pleasure that spread through my belly and down my thighs.

Thumbnail image: Editors’ Pick: Gay Anal Sex First Time: The Night I Finally Gave In — Featured

I reached down and grabbed his hips, pulling him deeper on the next stroke. Harder, I heard myself say. The word surprised me, but once it was out I couldnt stop. Fuck me harder.

Derek gave me what I asked for. He hooked my legs over his shoulders and drove in deep, the slap of skin loud in the quiet room. Every thrust rubbed that spot inside me until my cock was dripping onto my stomach without being touched. I was making noises I didnt recognize, raw and needy. He leaned down and kissed me while he fucked me, tongue matching the rhythm of his cock. I came first, untouched, pulsing hard between us, my hole clenching around him. The orgasm felt endless, like it was being pulled from somewhere deeper than my cock.

He followed soon after, groaning into my mouth as he pushed as deep as he could and pulsed inside me. I felt every throb. When he finally pulled out I was empty and sore in the best way, come leaking from me onto the towel hed spread. He cleaned me gently with warm cloths, then pulled me against his chest. We didnt talk much at first. I just lay there listening to his heartbeat, feeling the ache inside me and knowing Id want it again.

Later, when I could stand, he made us water and we sat on the edge of the bed. I told him it had been my first time. He smiled, not surprised, and kissed my shoulder. You took it like you were made for it, he said. The words went straight to my spent cock. I knew Id be back.

We fucked twice more that night, once with me riding him so I could control the depth, once with me on my knees at the edge of the bed while he held my hips and took me harder than before. Each time the stretch was easier, the pleasure sharper. By morning I was walking a little carefully, but I felt loose and satisfied in a way nothing else had ever given me. When I left his apartment the sun was coming up and I already had plans to text him again. I wasnt straight anymore, not after that night. I was just a man who knew exactly what he wanted: to be opened, filled, and fucked until I forgot my own name. And I had the perfect person to do it.

Gay Sex Stories
Gay Sex Stories
Dive into thousands of free gay sex stories. Explicit erotic tales, steamy gay fiction, and adult short stories updated daily. Read the hottest gay porn stories online.

Related Stories