What did he mean?

Sex Stories - A Fantasy - 5 Aug 2026

We cracked open a couple more beers and settled back on the couch, the TV playing with another video. Conversation flowed easily. After a bit Gary switched to porn, a threesome with two guys and one woman working hard between them. We sipped our beers and talked about how she handled both of them, her flexibility and stamina.

Gary grinned and said, “Feel free to wank if you want.” I laughed it off at first, but he was already undressing, his cock hardening in his hand as he stroked it slowly. The sight made my own pulse quicken. I hesitated, then took off my clothes too, joining him in the nude on the couch with my hand around my own cock.

He swapped the video for a home movie next. It showed Gary with a younger couple, his cock sliding between them as he took turns fucking the guy and the girl. I watched, first surprised, then alarmed, then curious, my hand still moving on cock. Gary glanced over and asked if I had ever had fun with a couple like that.

“No, never, but it’s okay… I mean, what is it like?” I managed, think I said.

Instead of answering, Gary slid off the couch and got on his knees between my legs. He said something about a condom that I didn't quite understand before he pushed my hand away and took my cock into his mouth, as he began to suck. My body tensed, heart pounding with a mix of fear and sudden excitement. I couldn’t process anything, but I didn’t push him off. His tongue worked my shaft, and after a while the alcohol helped me relax into it. I reached down to rest my hand on his head.

“It’s okay. It’s… nice,” I said quietly, letting him continue. My cock grew very hard under his attention, he was sucking while his fingers squeezed my balls. Thoughts swirled, i was excited, scared, frozen. But i liked it. My mind flickered back to what he had said about the condom. His words were plain enough, but my brain couldnt tell me the meaning.

Gary worked hard. He sucked me for a long while but in my state of nervous excitement I didnt or couldn't cum. Then i surprised myself. I gently pushed him back and said, “My turn.” Gary stood, and I dropped to my knees in front of him, staring at his hard cock up close for the first time. I nervously wrapped my hand around it and began to stroke it, like a friend, feeling it throb as I got him fully erect. My mouth hovered inches away, nerves, fear and excitement mixing with curiosity. I leaned in, careful with my lips, and took him in, sucking up and down while holding his balls. Sucking my first man.

As I tried to work Gary's cock his words still bounced through my head, this time forming meaning. He had said "a condom for sex". Oh, I thought, what he meant was "when i have sex with you I will wear a condom." Oh shit, anal sex, with me! The image of his sheathed cock pushing into my ass, filling me, fucking me, hit hard. My own cock that had failed to cum under Gary's blow job suddenly jerked and I started spurt right there, shooting onto the floor in heavy pulses while my mouth stayed around him.

The embarrassing moment after I realized he was planning on having anal sex with me was a blur. I came, I tried to clean up, I apologized, reassuring Gary I was ok. I got dressed as quickly as I could and fled.

Gary called me the next day. And the day after. I didn’t answer him. I didn’t think about it. It never happened. I'm not gay.

A week later I got the courage to call him. We talk about nothing for a while, as if the evening had never happened. Then I blurted it out… I was scared, and very excited. I enjoyed it. I was thinking about what he had said, concentrating of sucking my first cock. And when it hit me, that he was going to fuck my ass, i came with excitement. I couldn’t explain it. Bu it was ok.

I asked him bluntly “I was turned on by the thought that you would fuck me, I’m still turn on by it. Do you think I’m gay?”

He suggested I come over to talk about it. “When” I asked “Now” he said. I went over to his place, entering his den by the back laneway.

We talked. Gary was older and more experienced. He reassured me. I was probably just curious, open. It didn’t mean anything. Sure he would have done it, but it didn’t mean anything. I would have lied it he said.

Gary went to get a cold bottle of wine. I sat with my thoughts as I waited for him to return. I undressed, get naked for him, kneeling on my hands and knees on the floor, ass pointing to the door. When Gary returned he was confronted my my naked body, my anus up for him.

We didnt talk. He undressed and went for some lubricant to grease me up for action.

Cool lube stuck to my hole. His fingers followed, spreading it in slow circles before one pushed inside me. I let out an involuntary moan. The stretch made my breath catch. He worked the finger deeper, twisting and sliding until my body loosened around it. Then a second finger entered me , scissoring to try to open me, filling me in a way that made my cock twitch.

"You came over here thinking about this," Gary said, voice low. His fingers kept moving into me, stretching me wider. "Wanting my cock in your ass."

I nodded, still ashamed to admit it, forehead pressed to the floor. My anal ring stretched tight around his fingers, wanting him deeper. As he fingered me he felt around my rectum and told me how he was going to have fun fucking me. Eventually he pulled them out and wiped his hand on a towel. The sound of the condom wrapper tearing made my stomach flip. He rolled it down his shaft, the latex snapping into place, then added more lube over the tip.

Gary knelt behind me. The blunt head of his cock pressed against my hole, firm and insistent. He pushed forward steadily. "Relax" he said "You'll love this". The pressure built until my anal sphincter gave up, and the head cock slipped inside me. I groaned, fingers digging into the carpet, he felt so... big. He paused, letting me adjust, then sank deeper inch by inch working himself into me slowly.

He gave me time to relax and breath, pulling back then working forward again. Eventually he started to fuck me. The sounds of his efforts and my moans filled the room, mixing with the wet sound of lube. My cock hung heavy between my legs, half erect. He reached around and wrapped his hand around it, pulling me as he fucked me.

"You like that," he said, not a question, as he fucked harder, driving his cock deep. "You like getting fucked."

I couldn't answer. The sensation overwhelmed me, the stretch, the fullness of his cock in me, the way his cock rubbed a sensitive spot over and over. My orgasm built. I came with a choked sound, cum spurting onto the carpet while Gary kept working his cock into me. My hole was tight around him, pulsing as I spurted cum.

Gary didn't stop. He fucked me through it, getting more urgent, rougher. His hand left my cock and gripped my hips instead, pulling me back onto him with each thrust. He wanted to be in me deep. The condom shifted around his shaft, slick with lube, sliding in and out of my stretched hole. He grunted and tensed up as he entered me deep one final time, his cock pulsing inside me as he came.

When he pulled out, I stayed on my hands and knees, breathing hard. Gary peeled off the condom and tossed it. He sat back on the couch, observing his trophy.

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