Independent Study Pt. 03

"I know I'm in good hands," he bragged as he finished the job and pressed my sheathed cock head to his lips.

"Is there a particular position you want me to take you in?" I asked when he turned to face me again.

"You have all the experience. I trust your judgment," he said.

I could see the reality of getting fucked for the first time beginning to register on him.

"Lube me up, then, and let me think on it," I said handing him the gel, "Use as much as you want or think you need. Anal doesn't have to be painful...and shouldn't be...especially with this being your first experience."

I watched him carry out my instruction. I could see he was nervous as he assessed the size of what I would be fitting into him.

"I promise to make you feel good," I bolstered him as I stroked his back.

"I believe you," he assured me.

"I think the best position for your first time would be to lie on your left side and draw your right knee up toward your chest," I guided him.

He got in the position I'd described and asked, "Like this?"

"Perfect," I confirmed.

I squirted a liberal dollop of lube in his parted crack and began working it in.

He sighed as he discovered how pleasurable the pressure of a finger gliding over his pucker could feel.

"That's nice," he said.

"Good, it should be. Now, at this point I want to work it up inside you. It will feel best for you if you push down on your rectum for me," I instructed him further.

"Okay, I'm ready," he nervously told me.

"Push down harder," I said, still feeling some resistance to penetration.

When I felt his ring give I quickly inserted my middle finger to the first knuckle. He gasped and tightened up on it.

"Relax and keep pushing," I told him as I barely twisted my finger around.

When I felt his hole relax I began gently stretching it with a circular motion.

"Oh, Matt! That's fantastic!" he sighed.

I watched all the tension in his body fall away.

From there my much thicker thumb went in easily. I pumped it in and out a few times and then switched to two fingers.

By the time I succeeded in getting three in to the first knuckle I could see he was ready to receive me.

I straddled his left leg and mounted him with my right fist on the bed at his chest and my left behind his head, the crook of his neck curled against it.

"Your belly feels good," he sighed as I leaned in.

I slid my generously lubed cock head into his slick crack, quickly locating his sphincter and gently pressing for entry. He was still resistant.

"Push down," I reminded him.

I felt his ring push out toward me and quickly pried him open on my glans. He groaned as I pushed it through past the corona and then I felt a flurry of clenches that were likely painful for him.

"Steady, Mike, steady," I coached him, "I'm not going any deeper until you tell me you're ready. Remember to push down."

I couldn't recall when I'd been in someone so tight. It was all I could do to fight the temptation of just digging on in.

I steeled myself to the urge.

He wrapped both arms around my right one, upon which I braced myself most heavily, and clung to it tightly. He whimpered as he bravely tried to bear down on his tightly stretched orifice.

I finally felt it give a bit and he said, "Okay, more."

I pushed a couple more inches up into him. He groaned again, but almost immediately managed to relax around me.

"That's good...stay relaxed like that. Here comes the rest," I warned him.

I pressed on in till my balls nestled into the backs of his thighs. Air rushed out of his lungs in a pained groan.

"That's all...I'm in...you okay?" I asked, huffing from my restraint.

"Yes, sir," he responded, "Your balls feel nice."

"Good, focus on that...I'm going to start fucking you now," I told him.

"Yes, sir, I will," he affirmed.

His tightness already had me unbelievably close to another climax. With deliberately slow strokes I worked my cock in and out of him until I was able to utilize all the shaft behind the head I could reach up into him with.

My experience was almost working against me. The instinct for self-fulfillment had me craving the sensation I knew was available by bloating my cock to its maximum girth and cutting loose in him.

Again I fought it back.

He began pressing his ass back against my loins at my deepest penetrations and singing out his lust in impassioned moans. I began to reap the rewards of focusing on his pleasure and fulfillment.

His anus milked me like crazy as his chute formed to my probing phallus. Its velvety softness drew me into its tight fit like a magnet. I praised him for it.

Before long I felt the onset of what I knew would be my final orgasm of the day. I let my weight rest on him more completely than I had at any other point in our coupling and tucked him back against me with my right arm as I succumbed to it.

He ground against me as I spilled my load and I saw him press his lips to my right arm while he clung to it. I sank down and thrilled to his fervent writhing on my flexing member.

At last I slowly withdrew and sat back, peeling my condom and its modest catch off my dick and pitching it in the trash can.

I reached across him for a wash cloth and wiped my deflating organ clean. I let it go and it plopped down onto the back of his left thigh.

I triumphantly studied his motionless form.

Refolding my wash cloth, I tenderly swabbed his ass clean of the copious amounts of lube we'd used, and the deep anal juice I'd dragged from his chute with the churning of my cock.

"Oh-h-h-h-h-h, Matt!" he sighed, "What an incredible feeling!"

I rolled over and stretched out behind him, placing my hands behind my head and smiling up toward the heavens from my sense of accomplishment.

He turned and cuddled up to my side, alternately stroking my belly and fondling my spent genitals.

"Thank you!" he said in a breathy moan, "You were magnificent...so gentle!"

"I tried to be," I assured him.

I placed my left hand on his back and pressed him against me. He rested his head on my shoulder, fairly purring as he continued groping me.

"I've never felt so...safe...so...secure...with anyone," he enthused, "So full of cock...while you cradled me with your balls and belly...it was...I can't even find words."

"You don't have to," I told him as I stroked his back and kissed the top of his head.

Once I saw that he was coming down from his high I asked, "Anything else you'd like us to cover?"

He thought for a couple of minutes.

"Would it be asking too much for you to teach me how to give a blow job?" he meekly asked.

"I'd say you're primed for one," I replied with a laugh, "Stack the pillows so you can watch and I'll explain what I'm doing and why as I go."

"Unbelievable!" he almost shouted, "You mean I'm getting a blow job from you?"

"I don't think you'll ever get to sleep tonight otherwise," I said, "You're hard as steel."

I rolled a condom on him and he inspected it.

"It's still rolled up at the bottom on me," he said sounding disappointed, "Yours rolled all the way out way above the base."

I got in position between his legs and thumped his tasty looking morsel on my outstretched tongue to his amused giggles.

"This isn't a contest, Mike," I assured him, "Trust me...you've got plenty. And by the time I'm done with it you're going to know without a doubt it's all any man needs."

He was beaming with pride as I went to work on him. I paused in a few strategic places to explain what I feel are the key elements of my technique. He watched and listened intently.

As charged up as he was to begin with, I quickly had him squirming and filling his condom with the biggest spurter he'd probably shot in his young life.

He fell back into the pillows exhausted and pulled his condom off, then pitched it in the trash to join mine.

I crawled up and stretched out beside him on my back. I asked him to dispose of our used condoms in the toilet to spare the cleaning crew the indignity.

He fished them out and did as I asked, pausing to clean his cock with another wash rag before rejoining me.

"Can I try giving you one?" he pleaded as he stretched out beside me and ran his hands over my chest and belly.

"I don't think I have another hard-on in me tonight, Mike," I confessed.

I was almost unable to believe it myself after the day I'd had.

"I understand," he said, running his hand up onto my beard.

The disappointment in his voice was obvious and, again, I found him tugging at my heart strings.

If I'm honest my judgment was probably more than a little clouded by his worshipful gaze. I'm not above a good ego stroking.

But beyond that, this was no ordinary chance encounter. He was a good and sweet boy; handsome and eager to learn about himself.

He obviously saw me as a mentor and I felt imbued with a sense of responsibility to finish the job he'd asked of me.

I thought a minute longer and then said, "It's getting late. If you'd like you can stay the night here and take a swing at it in the morning."

"You're the best!" he gushed.

"Let's trade places," I said, "I'll probably have to get up at some point in the night."

He slipped a pillow out from behind him and pushed it toward me. Rolling out of bed he allowed me to scoot over and then crawled back up between me and the wall.

"Thank you SO much!" he said as he fondled my cock and balls again.

I turned out the bed lamp and felt his hand creep up onto my chest. He rested his head against my shoulder.

"You've definitely earned an A+ for our little independent study course here," I praised him.

He chuckled as I laid my hand on his and we drifted off.