Breaking In the Birthday Boy

Naked in his bed after midnight, Jacob propped himself against his headboard and brought his knees up. He reached between his legs and pressed Eric’s dildo against his well-lubed butthole and pressed gently. He had been regularly fucking himself with it for a few weeks now, trying to make himself into an acceptable bottom so that he could be fully versatile and give himself to Eric. 

He still felt that searing pain as the head of the dildo entered him, so he let it rest for a moment just barely penetrating him and did his best to relax his muscles. Soon, he felt more comfortable and pushed the rest of the shaft into his hole. Then he began to work it in and out, gently at first and then a little more aggressively as the lube coated everything. 

The backdoor stimulation got his dick rock-hard (hell, at 18 years old, everything got his dick rock-hard), so he continued assaulting his ass with the dildo with his right hand and began to jack his cock with the left. He worked up a good rhythm, synchronizing the strokes of each hand. He felt his orgasm rising and he concentrated on not crying out as he came, so as to avoid waking up his mother down the hall. 

He took a wet wipe out of his nightstand and cleaned the sperm off his belly and hand, then tucked the dildo into a box under his bed. He would clean it in the morning. He was satisfied that he was getting more and more comfortable with having something up his ass, but Eric had such a thick fucking cock he wasn’t sure he was ready to take it quite yet. But it was getting to the middle of summer and he was determined that he and Eric would fuck several times before he went across the state to college in the fall. Jacob thought back to the rainy night a few weeks ago, his 18th birthday, when he had gone two houses down to Eric’s at midnight. He had such a crush on his older neighbor, with his sandy, dark-blond hair, green eyes, and beautiful patch of soft hair across his chest. 

Eric had taught him how to give a great blowjob that night, then he had let Jacob fuck him. Jacob masturbated frequently thinking about the feeling of having his penis inside this handsome man who was so skilled and experienced in gay sex. 

Since that night, Jacob had practiced blowjobs with his friend Nate, a tall, skinny kid who’d been his jackoff buddy for years. They would go off into the woods behind their development to a quiet stream that was almost always deserted. Nate usually just wanted to masturbate, but Jacob had talked him into oral sex. Nate was kind of skittish and Jacob got the feeling he didn’t want to admit to himself he was gay. And getting his dick sucked by another guy was definitely gay, but his hormones took over and he let Jacob blow him a couple of times a week. Jacob thought he’d gotten pretty good at giving head, if he did say so himself. He had figured out how to bring Nate to the edge and then back off, building him up to a big orgasm. Jacob wanted to try swallowing Nate’s cum, but Nate always pulled out and turned away when he came, jacking himself the last few steps to completion, his skinny ass muscles dimpling as he pumped his load onto the forest floor. 

Jacob had thought about trying to talk Nate into fucking him as a sort of practice run. Nate had a smaller cock, much smaller than Eric’s, and Jacob wondered if it might be good to get a little live experience. But he didn’t think Nate would go for it and the more he thought about it, the more he wanted Eric to take his ass cherry, even if it hurt.

Saturday morning, I got a text from Jacob asking if I was free. I hadn’t actually seen him since the night he’d shown up on my porch in the rain, basically begging for sex. But he had texted me some pretty graphic messages, telling me he was training his ass with my dildo so he could take my cock. 

Yeah, just hanging out, I texted back.

Meet me at the trail over on Brookside?

The trail led into a wooded area bordering our development. What did you have in mind?

U’ll see. (Teenagers and their text spelling. Jesus.)

Half an hour?

K. See u then.

Jacob was already standing at the trailhead when I got there. He was wearing a sleeveless Nike shirt and some basketball shorts. His soft cheeks had the barest hint of beard and his thick dark hair was still a little damp. It was nearly noon but he probably had just gotten up when he texted. 

We walked for a few minutes, then he broke off from the main trail and set off across open woods. 

“Where are we headed?” I asked him.

“To a private little place,” he teased. “I think you’ll like it.”

A few minutes later, we came to a streambed about ten feet across and five or six feet deep. . There was just a trickle of water running through and it had a little spit of dirt in the middle of the base with a few roots and larger rocks dotting it. We stopped at the edge and I looked around. The overhead canopy was thick, so it was cool and shady and quiet. 

“So, is this where you and your buddies…”

“Jerk off? Yeah. Careful, years of our cum is all over the ground,” he laughed. 

“Looks like a nice little spot.”

“Yeah, and nobody ever comes out here since it’s so far off the trail. I’ve never seen anybody else.” Jacob walked a few feet to where a thick, ropy vine was hanging down from the treetops. He tugged on it and gave it a test. Then he looked over at me and held my eyes as he peeled off his shirt, then stepped out of his shorts and tighty-whities. He was naked except for his tennis shoes and socks, his penis beginning to plump. 

He took hold of the vine and got a running start of a few steps, then swung out over the bank of the stream and dropped neatly down to the patch of dry ground in the middle. “Come on down!” he called up to me. 

“OK, Tarzan. I’m not sure that would be as easy for me. Looks like you’ve had practice.”

“You can come down the rocks over there,” he said, pointing to a point where some rocks and cinder blocks had been piled up, providing a makeshift set of stairs. “If you want to be a pussy.”

I made my way down the rocks carefully and went over to where he stood. Jacob’s hand went to my waistband and made quick work of the button and zipper on my shorts. Then he pulled down my boxer briefs and my cock sprang free into the warm air of the woods. 

He ran his hand over my bush. “What happened here?” he asked. “I like it.”

I’d forgotten that he hadn’t seen me naked since I’d given Eric Jr. his summer haircut. I’d trimmed my brown pubes down to just a little triangle right at the base of my dick. 

“I like to clean things up for the summer,” I told him. “Keeps it cooler.” I glanced around us a little nervously.

“No need to be nervous,” he said. “It’s totally private out here.”  

Jacob dropped to his knees and held my stiffening rod in his right hand. Slowly he lowered his lips over my head and partway down the shaft. I came to complete erection in the heat of his young mouth. He began to use his tongue to great effect and used one hand to gently stroke my scrotum and fondle my balls, occasionally running his fingers over my trimmed bush. Soon he had my entire shaft wet and shiny and was alternating between working my nuts and gently probing my asshole with his left hand. 

His skill as a cocksucker had increased exponentially since the clumsy blowjob he’d given me during our first encounter earlier in the summer. He’d definitely had practice. As I could feel my orgasm building, he used his left hand to reach between his legs and jack his own cock as he worked mine over.

A couple of minutes later, I reached the point of no return. I didn’t know if he was a sperm swallower or not, so I gently pulled my dick from his mouth and began to jerk it. “Buddy, I’m gonna blow,” I told him. He stayed right where he was, his face right at my crotch. About six jerks later, I fired my load right onto his face, splattering his cheeks, nose, lips and chin. One glob landed at his temple and clung to his hair, There’s Something About Mary-style. 

“Fuck!” I gasped as my abdomen tensed from the orgasm and the last bit of my nut butter oozed out of my piss slit. 

“Liked that, I see,” he grinned as he stood up.

“Yeah,” was all I could say as I caught my breath. “You’ve been practicing.”

“Little bit.” He bounded up the rock staircase and went over to where he had shed his clothes. He picked up his tighty-whities and used them to wipe the cum off his face. Then he slid the jizz-splattered Jockeys on and pulled up his shorts. He tossed his muscle shirt over his shoulder and watched as I joined him on the bank of the streambed.

“That’s not the only thing I’ve been practicing,” he said.

“Oh?”

“I’ve been working with your dildo too.”

“And how’s that been going?”

“I’m ready to graduate to the real thing now.”

“You’re sure?”

“Very sure. I want to feel your cock in my ass.”

“When do you want this to happen?”

“Next weekend. I want you to get us a hotel room for the night. A nice one. Downtown. I’ll tell my mom I’m at Tyler’s. That way we can take our time and fuck the whole night.”

“You’ve got this all planned out, I guess.”

He held my eyes with his. “I’ve been thinking about it for a while. I’m gonna give you my cherry. I want it to be special. Now let’s head back.”

He turned and began heading across the woods back towards the trail. I could hardly believe I was making a date to fuck a teenager in the ass. But that’s what was happening, so I shrugged to myself and followed him out of the forest. 

The next Saturday, I had booked us a room in a large convention hotel downtown. I figured we could blend in better in a crowd. Even though Jacob was now legal, it still felt kind of forbidden and naughty to be taking him to a hotel explicitly for sex. Even though he was begging for it, I still didn’t want to advertise what we were doing. 

I had splurged on a high-floor room with a sweeping city view, but even that wasn’t quite enough for Jacob. The little extortionist hit me up for a sushi dinner as well. I love a good spicy tuna roll, so I acquiesced and we had a nice meal before returning to the hotel and boarding the elevator for the trip up to the eighteenth floor. The parallel between the floor and the age of my companion wasn’t lost on me as I hit the button. Two other couples got in the car and stood in front of us as the doors closed. We began to ascend and suddenly I felt Jacob’s hand surreptitiously cup my ass. He began to squeeze my left cheek just two steps behind the other couples. Meanwhile, he looked up at the floor numbers as they blinked by with an innocent look on his young face. 

We stopped on sixteen and one of the couples got off, then two floors later we were exiting. As soon as the doors closed behind us, Jacob grabbed my arm and turned me towards him. He moved in quickly and kissed me, his tongue probing my mouth right there in the elevator lobby. His hand went to my crotch and I’m sure he could feel the effect his kiss was having. 

“Christ, you little exhibitionist,” I laughed. “Let’s take this to the room.”

“Don’t you want people to see what a hot little piece of ass you’re getting?” he teased. 

I decided to call his bluff. There was no one in sight, so I pushed him to the wall and put my leg between his, spreading his hips apart. I ran my hands up and down his sides and over the bulge in his khakis, then around to his ass. I leaned in and sucked on his neck as I kneaded his glutes. “You like this, buddy?” I whispered intensely. “You want me to bend you over and take you right here in the hall?”

He devoured my mouth again. “Fuck, that’s so hot,” he said. “OK, let’s get to the room and get this show on the road.”

As soon as we got in the room, he was all over me again, kissing me, gently biting my lower lip, licking my neck, grabbing my dick through my slacks. 

“You’re a dirty boy,” he said. “I think you need a shower.”

With that, he kicked off his shoes and turned to saunter to the bathroom, unbuttoning his shirt and pulling it off on the way. When he reached the door, he glanced back over his shoulder at me, gave a stripper-bump of his hip, and dropped the shirt. 

I followed him over to the bathroom, pulling my own shirt off on the way. When I got to the door, he had removed his pants and folded them on the counter. He stood with his back to me, clad only in a pair of dark blue Jockey shorts. He slowly slid them over his hips and let them drop to the floor, his slender bare rump now seeming to glow in the low light cast by the fixture over the mirror. 

Slowly, he turned around to face me. Of course, my eyes immediately zeroed in on his cock, moving to full erection. Even in the lower light, I could tell he had trimmed his own dark pubes into a narrow patch above the base of his penis, in homage to my summer grooming habit. 

He gave me an eyebrow raise, then went to the walk-in shower and turned the faucet. As soon as it warmed up, he stepped under the spray. I was almost mesmerized watching his supple young form with the water cascading down it, running in rivulets across his shoulders, down his nipples, and over his shallow, slightly elongated navel to points south. I was overcome with lust and yanked off my remaining clothes and marched naked to the shower, my erect prick pointing the way.

Under the shower spray with him, I squirted the body wash from the wall unit into my hand and began to lather his torso from armpits to waist. Then I sank to my knees and slowly took his raging hardon in my mouth. I loved the clean taste of him and his spongy knob was a perfect lollipop for my tongue. I kneaded his ass and enjoyed hearing his moans of delight mix with the sound of the water. 

After I had him worked to near orgasm, I backed off. I stood and turned him around, this time soaping his back, working my way down to his ass and gently probing his crack with my fingertips. I separated his cheeks and let the water sluice through. He was as neat and tidy back there as he was up front. 

“It’s time,” he said finally and turned the water off. We got out of the shower and dried each other with the big fluffy bath towels on the wall rack. Then Jacob went out into the bedroom and I followed. He sat on the side of the bed nearest the window and laid back. Then he pulled his knees up towards his chest, opening his beautiful hairless cunt to me. He had a perfect oval of light pink with his tight little button a slightly darker shade. 

I dove on it like the rimming fiend I was, circling it with my tongue and lapping at it like it was the most luscious caviar. Finally, I pushed my tongue inside him and felt him relax and sigh with pleasure. I knew it was time, so I stood and looked down at him, my cock as hard and ready as I could remember it ever being. I moved to the nightstand where I’d placed my intimacy supplies earlier. 

“Eric… fuck me bare,” Jacob said. “Fuck me bare and put your raw load in me.”

Oh fuck, my dick was now even harder, feeling as though the air itself were pressing against it. I picked up a small tube of lube and went back to my waiting partner. I slowly worked a small dollop into his pucker and slicked his passage, inserting a second finger to test his readiness. He didn’t flinch, so I squeezed out a stream onto my head and shaft and coated the full length. The touch of my fingers was electric and I would have to concentrate on not cumming as soon as I entered Jacob’s hole. 

I settled between his legs again and gripped his thighs, pulling him closer to me. I angled my cock slightly down so that the tip was just knocking at his back door. Jacob could feel the touch and his eyes closed as held his breath. I pressed forward firmly but not harshly and the thick head of my penis slid through his ring. He gasped and tensed for a moment, but then he let his breath out and relaxed into the fuck as I gradually worked my full six inches into him. As my balls came to rest on his taint, a grin spread across his face.

“You popped my cherry good, bud.”

“I’ve just started, kid.”

With that, I began thrusting. I gave him long, full strokes from the beginning. He had primed himself with my dildo for weeks and he was obviously up to the task of taking a cock-pounding. As I worked him over, his mouth opened and he let out soft grunts of satisfaction. I leaned forward and propped myself on my elbows over him. I moved my face in close and kissed him while I continued to take his ass like a giant pipe cleaner in a test tube. He thrust his tongue in my mouth and pumped it nearly as hard as I was pumping my cock into him. 

We rutted like that for several minutes, though time seemed to stand still. Then Jacob propped up on one of his arms and locked one of his legs over mine. “I want to ride you,” he said.

We did a sort of tandem roll and he wound up on top without my cock ever leaving him. He began to bounce up and down, throwing his head back as he found all of his best pleasure spots with my cock. Soon, his right hand began jacking his dick while his left pinched his nipple. 

The warm silkiness of his inner flesh was making magic on my fuckstick and I could feel my balls starting to tighten, sending a tsunami warning up my shaft. Jacob’s pre-cum was shining in the glow of the bedside lamp too. “Fuck my ass, fuck my ass, fuck my ass,” he began to repeat over and over. He had done much the same kind of thing as he reached climax earlier in the summer when I had let him top me. 

“I think we’re about to ride the roller coaster together,” I told him. 

Jacob just grunted in return and jets of his milky spunk began to spray like a lawn sprinkler. One jet hit my lower lip and I lapped up a taste. It was sweet, bitter, salty… like a sugared pecan. His sphincter squeezed as he came and that was all I could stand. I held his hips tightly as the floodgates opened on my ball reservoirs and I began launching my seed into his colon. I fired off so much it felt more like I was pissing in him than cumming. I came so hard my toes curled and I thought my calves were going to cramp from the muscle tension.

After our orgasms subsided, he collapsed on top of me, his head against my collarbone as my penis slipped from his anus with a wet-sounding plop. We both panted from exertion and the sheer physical pleasure of our coupling. Just a few minutes later, we were asleep. 

I woke early the next morning, my naked body still tangled with Jacob’s. At some point during the night we had pulled the sheet over us to the waist. I stretched an arm that had gotten stiff. He began to stir as well and sleepily ran his hand down my chest and stomach to my cock, then briefly tickled my balls. He slid to the edge of the bed and sat, his feet on the floor. 

“I gotta piss. Then I might let you fuck me again before we check out.”

I reached over and playfully slapped his bare rump as he stood. “What makes you think I’d even want to fuck your skinny ass again?” I teased.

He nodded toward my crotch. “Your boner,” he said.

I looked down and saw my morning wood tenting the sheets very obviously.

“Guilty,” I laughed.

Jacob stretched, then with a naughty glance over his shoulder he took one asscheek in each hand and parted them, giving me a look at his no-longer-virginal young cunt before heading off to the bathroom. When he got back, I was going to show him a thing or two about vigorous wake-up sex – doggy-style.

Damn, this kid was going to be a handful when he got to college.