The Chaperone

Coach does whatever it takes to help the star basketball player get some sleep before a big day.

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Inspired by the “Just For One Night” porn scene with Jodi West.

“What is it, Blake?” I said. We were halfway through the campus tour, standing on a corner near the commons while a guide rattled on into a microphone. Blake was beyond distracted though. He kept fidgeting, shuffling on his feet, grimacing as he adjusted the front of his shorts again and again.

“Nothin, Coach,” he said, but I watched his eyes stray toward one of the women on the tour, sun illuminating the copious breasts in her low-cut blouse.

Blake was our star basketball player. I’d been tasked with showing him off to prospective colleges, and we had an appointment the next morning to play for some recruiters. He’d nearly kept me up all night, tossing and turning in the king-sized bed we were sharing in our hotel room. Now I was getting a sense for why.

“I know you didn’t get enough sleep last night,” I said. “Are you sure nothing’s wrong? Big day tomorrow.”

“Yeah, I’m fine,” Blake said, and again he pulled at his distinctly swelled-up crotch, his eyes continuing to stray.

I let him have a few sips of my wine at dinner that night.

“Are you missing your girlfriend, Blake?” I said.

“I guess so, yeah,” he said. I was aware that Blake had his first serious girlfriend. Thankfully it hadn’t affected his performance on the court, yet. “Mom and Dad let her spend the night a lot, so I’m pretty used to, you know, that.”

“That’s progressive of them,” I said.

“They’d rather I do...stuff...under their roof, I guess,” he said.

“I see,” I said. “Well, it’s just one more night. But we definitely need to get some sleep tonight, with the exhibition tomorrow. Think you can manage?” I said. Blake nodded, but I could see the frustration in his eyes. I sympathized, knowing how it could be at that age.

We took a walk around the lake before heading back to the hotel. I flipped on the TV while Blake showered, then I took one too and we settled in to sleep. But it wasn’t a few minutes after we turned out the lights that Blake started shifting around. At first he was tossing and turning, then kicking at the sheets. Then he let out the most frustrated sigh.

“Still can’t sleep?” I said, flipping the light on next to the bed.

“Yeah,” he said, staring up at the ceiling.

“Is there anything that would help?” I said. Blake shrugged.

“I have a boner. It won’t go away,” he said, looking resigned and a bit ashamed.

I took a deep breath. “I see,” I said. “Can you think about other things? Distract yourself?”

“I’ve tried,” he said, squirming under the sheet.

“Well, let me take a look,” I said. I guess I was a bit frustrated myself and not thinking clearly. I tossed back the covers to reveal Blake’s young, mostly-nude body, the boner in his boxers painfully obvious.

“Coach!” he said, shifting his legs to try and hide it.

“It’s not like I’ve never seen an erection before,” I said. “I suspect you’ve had that most of the day. It’s not healthy to be excited like that for an extended period of time.”

“I know,” he said, his cock throbbing under the thin fabric of his shorts. “Jenny and I, we have sex before bed pretty much every night. I can’t sleep without it anymore.”

“You don’t, you know, take care of your own needs?” I said, watching Blake’s thick cock pulse and throb. A wet spot was forming near the fly.

“It’s not the same,” he said. I sighed. All I knew was that the longer this went on, the less sleep we would get. So I didn’t overthink it when I made the decision to pull back his boxers and free his desperate boner.

“What are you doing?” Blake said as his slick rod pounced out.

“If we don’t take care of this we aren’t going to get any sleep,” I said as I took him in my hand and began to stroke. Blake gasped, then groaned. “Just lay back and think about Jenny.” The kid closed his eyes and soon his breathing ramped up. He stretched out his lithe musculature as he began to enjoy what I was doing. “It’s helping, right?” I said.

“Y-yeah, a little,” Blake said, his barely-opened eyes rolling back in his head as I stroked down to the base of his fat dick then upward till precum was oozing out the tip. I smeared that around the head before giving him another pump with my fist. “Usually I need lube,” he said with a pleading look.

I sighed again. “Well, we don’t have anything like that,” I said. I considered for a moment what to do next, then decided I might as well go for it if I wanted to take care of the problem. “Here,” I said, and throwing caution to the wind I leaned forward and sank Blake’s fat dick between my lips and past my tongue, all the way until it was buried in my throat. I kept my lips tight as I came back up. The taste of his precum was so tangy it seemed to sear my tongue, and the kid’s cock was so thick - much bigger than my own - that I really had to strain to get it all down my throat. But I did my best, taking him into my mouth until my nose was pushed into his bush of pubes, then repeating the process.

I held his balls in my hand as I sucked him, thinking of how full they were and how the job wouldn’t be finished until they were empty. I decided that I was prepared to take that load in my mouth if it would save us the time of having to clean up afterward. But after about ten minutes of me sucking his cock both deep and shallow, stroking him as I sucked, it didn’t seem like he was any closer.

“Can you cum like this?” I said, slapping Blake’s meat against my sloppy mouth and stubbled dad-jaw.

“Not usually from head,” he said.

“Well, how do you usually cum?” I asked.

He took a moment before he answered. “Inside,” he said.

“Well we’re certainly not doing that,” I said, continuing to stroke him and suck on the head. “What if I keep stroking you like this?” I said.

“I don’t know...” Blake said. I could tell that it was helping at least somewhat, so I continued to alternate stroking his cock with long dives of my mouth down to the base of his teen rod. The night was wearing on, though, and my jaw began to get tired.

“Alright, let’s try something else,” I said. I turned on my side and popped my briefs down over my muscle butt. “Get up against me...there you go. Put your cock right up against my ass - there you go, just like you’re going to slide it into Jenny. Ride it against my butt like you’re with her.” Blake gripped the sides of my hips as he got into position, and then I felt that hot rod press against my hole, the shaft of it fitting snugly in my deep crack. Blake began to hump against me, the throbbing heat of him sliding down and back up against my hole. I figured he could shoot his load like that - it would land on my back and ass but that would be easy enough to clean up. Then it would be all over and we could get some sleep.

But Blake just kept humping. Even as I felt my fuzzy ass slicken with his natural juices, I could tell he wasn’t ready to bust.

“Dang it, Blake, don’t tell me this isn’t working either?” I said, pushing my butt back against him to try and provide more friction and sensation.

“It’s not...” Blake said, and just then the juicy head of his prong caught against my hole. “...too bad,” he finished, and held his cock there, where it prodded against my hole. I think both of us lost our breath for a second. I involuntarily relaxed, but then some of him began to inch inside of me. Feeling that, I tried to back off of him but Blake kept pressing forward.

“Careful,” I said, moving more decidedly so that his cock head sprung out from where he’d been pushing into me. “You almost went inside.”

“Sorry,” Blake said as we re-positioned and he again began to hump against my rear.

“Here,” I said, grabbing his hands and bringing them up to cup my furry muscle tits. “Pretend they’re Jenny’s...tweak my nipples...there you go.” By now the kid had a steady rhythm going, but more and more often the head of him would catch on my hole and try to push inside. Finally he held it there again and pushed.

“Why do you keep doing that, Blake?” I said.

“It’s helping,” he said. “It makes me feel like I’m teasing Jenny’s pussy.” I signed and relaxed to allow a bit more of him to push just inside me. It was really just the tip, so I figured it wasn’t that big of a deal.

“There,” I said, out of breath from allowing Blake to push inside me just that much. “Will that do it?”

“I think so,” Blake said, grabbing at my tits as he maneuvered his cock, shallowly pushing it in and out so that my tight hole gripped the head again and again. “Oh man, Coach, it’s just like I’m with her,” he said, and leaned forward to suck my neck.

“That’s it, son. Oh!” I said, feeling another inch of him push into me. There must have been seven more inches beyond that, so I let him have it. “Not too deep, Blake, okay?”

“Okay,” Blake said, holding his cock steady and licking at my neck in a way that gave me goosebumps. His cock pulsed and I felt it stretch my hole. Then warmth seeped into me - I figured it must have been his precum, of which he clearly produced a lot.

“You can get close like this, right?” I said.

“I think so,” Blake said, breath hot against my ear. He groaned and sucked on my earlobe. “It’s definitely helping,” he said, and I felt another inch go inside of me. “It’s soo good,” he groaned, and continued to press harder.

“Blake!” I said. His hands were tight around my pecs.

“It’s really working,” he said, breathless and continuing to push.

“Are you sure?” I said, feeling more of him breach my hole, so much fat teen dick that I had to call out.

“It’s...” Blake said, and flicked his fingers against my nipples in a way that scrambled my brain. Another inch went inside of me. Then I felt it, the unmistakable brush of his bush against my rear. He was inside of me, completely.

“Blake! My god, you’re all the way inside of me.”

“I know, but don’t make me stop. It’s really helping, I can definitely cum like this, it’s what I do with Jenny...”

“Don’t tell me you put it inside of her without a condom on?” I said.

“Well, sometimes - I always pull out, though,” he said.

“Well, don’t move too much,” I said. “And definitely don’t thrust. I’m glad it’s helping but this is wrong, we should really stop,” I said, but even as I said it I felt Blake’s cock swell inside of me and somehow it made my hole tighten back and sent a wave of pleasure through me. Blake was fondling my tits and licking the back of my neck. “I...” I said, faltering. “We can’t do this...but we gotta get some sleep. Just get close and pull out and cum on my ass. You understand?” I said, and Blake’s cock swelled in me again. Despite myself, I moaned.

“You got it, Coach,” Blake said. He pressed his body into mine, his smooth chest and stomach sliding against my broad back. Though I hadn’t thought there was any more of that dick left to go inside me, more did, a half-inch of thick teen cock root that stretched me to the limit and hit me hard.

“Oh, god!” I called out.

“I won’t fuck,” Blake said, nibbling on my neck. He twisted my nipple just enough so that I reared forward and inadvertently slid several inches of him out of me. I immediately pushed my ass back so that he went fully inside.

“Fuck, Coach!” Blake said.

“Oh Blake,” I said, aware that something in my body was taking over. I couldn’t resist that sensation and again I reared all the way forward until his cock was almost completely out of me, nine inches of glistening teen rod with just that bare pulsing end still lodged inside. “Does it feel good for you? As good as Jenny’s pussy?”

“So good,” Blake said in my ear. I rocked my ass, teasing the tip of him with my hole. Then I backed up and slid him all the way inside of me again.

“Oh my god, Coach,” Blake said, his voice quavering with pleasure. I felt his hands travel down my torso across my thick stomach, until one hand wrapped around my briefs-clad cock.
“I play with her clit,” Blake said as he began to stroke my rod. I began to lose all reason, backing on and off the kid’s cock with abandon.

“Show me how you fuck her, Blake. If that will help. Just for a bit,” I said into his ear.
Blake groaned as he began to thrust. I was shocked at how good it felt. There was barely any resistance as he pushed all the way into me, then back out. I suspect all that precum had lubed me up well.

“Do not cum in me, Blake,” I said. “Just use me to get close. Oh fuck,” I said, reacting to a certain spot he kept hitting every time he went deep, which seemed to melt my whole body.

“Okay, Coach,” he said. “Don’t worry I cum quick like this every time. Especially when I really pound her,” he said, and taking hold of my hips he began to thrust hard and deep.

“You’re really fucking me, Blake, oh god...you gotta stop,” I said.

“Getting closer,” Blake said, slowing down just enough to keep a steady, pounding rhythm on my hole. He kept his steady grip on my cock as he fucked, and I found myself pushing back into him, matching him thrust for thrust.

“Getting really close,” Blake said. “I always pull out with her.”

“You've got to pull out," I said.

“I don’t want to this time, Coach. Come on, let me do it. I need to, it’s the only thing that’ll work...”

“Oh fuck it, cum inside me Blake. Deep as you can,” I said, beyond reason. Blake began to call out. He pushed into me all the way and I felt his cock swell.

“I’m gonna blast in you, Coach. Fuck!” Blake said.

“Do it, kid. Shoot inside me. Get me pregnant,” I said. Blake’s mouth found mine and as I felt the first shot swell his cock up and shoot out of him and into me, we made out like lovers. Teen jizz was shooting into me like a water hose, the root of his rod swelling to absurd proportions as he seeded my insides.

“I’m blasting my babies into you, Coach. Fuck!” Blake said, continuing to curse like a sailor as he unloaded every drop of his cum into me.

And then he was done. He released his hold on my cock and tit. I grimaced as he slid out.

“Thanks, Coach,” he said, letting out a big, satisfied sigh. “Goodnight.”

“Uh...goodnight, Blake,” I said as he turned away from me and settled in. I reached over to to turn the light off, then pulled my underwear back up over my butt. My head was reeling and Blake’s cum was leaking out of me. My cock was still rock hard. And as Blake began to snore, I laid there with the realization that I was going to be the one struggling to sleep, now.

To be continued...


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