Tell Me When

“I know this way I can help you get off,” my buddy Andy said to me one night when we were jacking off in his dorm room.

“What’s that?” I said. We were side-by-side on his floor, amongst pizza boxes and video-game detritus, naked, our hard bodies flexing and straining as we pulled on our fat, shaved dicks. He’d brought the lube out earlier and cued up some porn on his TV. He’s always coming up with ideas to help us get off faster.

“Easier if I just show you,” he said, and he got up on his knees and came over to me. He put some extra lube in his hand then applied it to my cock. It was really the first time he’d ever touched my cock and I tried not to act like it was a big deal. “Better if you’re really lubed up,” he said, never really looking me in the eye. Then he got some more lube on his fingers and I watched as he applied them to his asshole.

So I had some idea of what was coming next. I mean, I always knew he liked to play with his asshole when we jacked off. He was kind of cagey about it at first, and would take his finger out whenever I looked at him. But it was pretty obvious.

He was the one who got me into shaving, anyway. I just liked the way it looked on him, his hard, muscled body all smooth, just bare, sheared skin above his cock. When he showed me he shaved his asshole too I was surprised at first. But that looked pretty hot as well so I started doing it.

Andy kept my cock in his hand as he straddled my legs. He pointed the tip of it to his hole and bore down. The tip of it disappeared inside of him. I felt the tight warmth of it, gripping the end of my dick. Fuck it was good. But Andy was kind of panting.

“Does that hurt?” I said.

“Just at first,” he said. “It’s cool. I’ve put stuff up here before, it’s no big deal.” He slid a couple more inches inside of him. “Believe me, I’ve tried this before and it makes you cum, like, instantly,” he said, and with some effort he was able to sit down on me fully.

I watched the sides of his torso, the ridges of his rib cage as he breathed heavily from taking my cock inside of him. Then he started to ride it – up and down, all the way. “Feel good?” he said to me.

“Yeah,” I said. “Definitely.”

“See? I told you. Just let me know when you’re about to cum.”

“Okay,” I said. Wondering if we should be using a condom, but Andy made it seem like we weren’t even fucking. Maybe he just didn’t want any cum inside of him? Andy was always a little mysterious. I knew he dated girls and stuff but we’d been doing this stuff with each other for the last two semesters.

“Damn, man, it feels really good,” I said as Andy began to get a rhythm on it. Honestly it was partly the way it felt, but mostly the way it looked – my big, raw dick splitting open his tight little ass. I’d only fucked a few times before this, and I’d never fucked anyone in the ass. I couldn’t believe how good it looked, his hairless hole wrapped around my fat dick.

“Awesome, man. Just tell me when you’re close, okay?” Andy said as he bounced on me. He wasn’t jacking off anymore, he wasn’t even hard. He was even holding his cock in his hand so it was sort of invisible, like he was all about his ass.

“Have you done this before?” I said.

“Just a couple times,” he said. “With my old friend in high school, the one I told you about,” he said. He’d said he used to jack off with someone in high school but he’d never told me he’d done anything like this. “We used to do it for each other. Just as a way to get off quicker, you know?”

“Yeah,” I said, nearly breathless from the way his tight asshole was gripping my cock with each bounce of his ass on my pelvis. He was facing away from me so I couldn’t really see his face. “I can see why.”

“Right?” Andy said, bouncing away. “It’s like the best feeling.”

“So your friend used to do it for you?”

“Yeah we’d do it for each other. I mean you don’t have to. I’m used to it and everything,” Andy said.

“Cool,” I said. Andy started taking these slow strokes, pausing with the tip just inside him then taking his time going down. Then sitting there and flexing his hole around the base in this way that was making me feel like he was gonna just milk the cum out of my nuts. It really felt like that: like my cock was being squeezed to extract the juice.

“Alright man, I’m getting close,” I said.

“Are you?” Andy said, and if anything he sped up on my cock. He was really impaling himself with it.

“Yeah...pretty close,” I said, feeling my balls start to pull tight to my body the way they do when I’m ready to blast babies.

“Tell me when,” Andy said, if anything bouncing faster on my dick.

“I’m gonna,” I said, and felt my mind start to scramble.

“Tell me when,” Andy said again, and his voice was more insistent. But hadn’t I just told him? He was still bouncing like he wanted to take my load.

“Okay. Now,” I said.

“Now?” Andy said.

“Like right now,” I said, because I felt the first shot of my cum unleash and go right up into him. “I’m cumming man.”

“You gotta tell me when,” Andy said, still bouncing on my dick.

“I am, man. I’m cumming,” I said, my cock pulsing as more and more of my load spurt out of my balls and into Andy’s incredible hole. Andy bounced a couple more times and then he came off of it. I watched as a creamy stream oozed out from his hole and glazed down my still-pulsing shaft. I only had a couple shots left and they spurt out a few inches into the air as Andy took hold of my prong and jacked it. His hole was still dripping with cum – did he not realize he’d taken most of my load?

“Nice, man,” he said. “See? Works like a charm.”

“Yeah,” I said, head spinning from one of the best orgasms of my life. “Really does. Fuck!” Andy jacked me some more then, in one unexpected motion, he leaned down and cleaned off my cock from base to tip, taking into into his mouth and slurping off the remaining cum. “Uh!” I gasped. Andy smacked his lips and let go of my cock.

“Thanks man,” I said.

“Any time,” Andy said. “Like I said, my friend and I used to help each other out like that all the time.”

“That’s awesome. I might have shot some cum in you, though,” I said.

“Really?” Andy said, reaching back and feeling his hole. “Oh. I thought I told you to tell me?”

“I did,” I said. “But you kinda kept going.” Andy got a brief scowl on his face. Had I done something wrong? But the scowl went away as quickly as it had arrived.

“Oh well. I guess a little bit isn’t a big deal,” Andy said, though I doubted he had a little bit inside of him. I always shoot huge, and I had a good sense of what my loads looked like. I bet he had twice as much still inside him as what had already slipped out. “Just make sure you tell me next time, okay?” he said.

“Sure man,” I said.

“No big deal,” Andy said, wiping off his ass with a pair of his dirty underwear he plucked from the floor.

“Is it cause it’s not safe?” I said.

“Safe?” Andy said. It was like he didn’t think what we’d done was sex at all. “No it’s just a personal preference,” he said. “No big deal, though.”

“Cool,” I said, and even though I was still plenty confused, I felt satisfied, and we went back to studying and pretending like it had never even happened.