Breaking In the Birthday Boy

The last two weeks before Jacob turned 18 seemed to drag on and on for him. He was precocious and seemed as though he had been sexualized at a young age. He tended to wear tank tops, displaying armpit hair that started coming in at about 13. Not long after, he grew a faint little happy trail and took to walking around the neighborhood shirtless and spending a lot of time at the community pool in the summer. He would wear short little navy blue trunks while he sprawled on a lounge chair soaking up the rays. Then he’d take a slow walk over to the stairs leading into the pool and gradually enter, then lean against the side with his elbows up on the ledge and survey the area. His black, wavy hair always seemed to fall just right even wet and his piercing, ice-blue eyes could practically be seen from space. And I swear those eyes spent more time glancing my way than anyone else’s. I could sense them lingering on my chest and stomach while I was tanning. I kept myself in pretty good shape with cardio and I was proud of my muscular legs and the fact that my ass was still winning the battle with gravity.  

I admit, I spent some time looking at the kid. Shit, he was beautiful. He and his mom had moved into the neighborhood about six months after I did. Jacob was about 12 then and even at that age he exuded a raw sex appeal. His features were even, he had perfect hair and teeth, and his skin was smooth and golden after days spent in the sun. Almost immediately, I sensed he was gay. He never hung out with girls and he was always striking up conversations with the dads at the pool. They probably figured it was because his own father was absent, but I was sure he had a different motivation. I recognized some of myself in him.  

Over the six years since he’d arrived, I’d watched him grow up from two houses down. He’d hit a growth spurt at about 15, but even then he never had the gangly awkwardness of most teenagers. He projected a confidence beyond his years and seemed to grow more handsome every day. His shoulders and legs started developing from shooting hoops in the driveway and playing on the junior varsity team. He also rode a mountain bike around the neighborhood a lot before he got his driver’s license. A couple of his buddies were over at his house nearly every afternoon, and they rode their bikes up and down the street. A couple of times a week, they’d ride off into the woods behind our cul-de-sac and not come back for an hour or so. I had a pretty good idea what was up those days. It hadn’t been that long since I’d been a horny gay teenager and I knew what I did in the woods with my “special friends.” 

Jacob talked to me every once in a while when I was out in the yard and he rode by. And he’d made conversation a few times at the pool or when I ran into him at the grocery store just outside our neighborhood. He was vaguely flirty, always complimenting my on my shirts or telling me my new haircut was nice. He had a slightly unnerving way of making total eye contact and he would often casually lift his shirttail to scratch his stomach, giving me a glimpse of his flat little belly and shallow navel. 

I’ve never actively tried to hide the fact that I’m gay, but I don’t go around wrapped in a rainbow flag sneezing glitter either. But people knew. I openly dated men and sometimes brought them to neighborhood functions. So Jacob had to be aware and it just reinforced my conviction that he was into guys. 

I found out for sure one night when I was scrolling through Grindr. (I know, I know.) I got a message from a pictureless profile with a username of simply “J”. 

I know that’s you, Eric. I recognize the chest hair in ur profile pic. Plus you’re close by.

It was followed by a selfie of Jacob, shirtless in his bathroom. And sure enough, the location on his profile said he was 460 feet away. And my profile pic was just my torso from neck to navel. 

No sense trying to deny it. What are you doing on here? I responded. 

Probably same thing you are, lol. Looking for dick.

Uh, you’re a little young!

I’ll be 18 a week from Sunday. 

Why’d you message me?

I really dig older guys.

At 31, I didn’t really consider myself “older,” but to him I guess…

And how many older guys have you been with? I asked.

Longer pause. I wondered if he’d gone. Then:

Well, none. But I really want to. Can I suck your dick?

Jesus, this kid was really horny tonight. In spite of myself, I was getting hard and I stroked my cock through my gym shorts. 

You’re jailbait, young man. 

It’s less than 2 weeks! Like it matters.

It would matter a lot to the cops.

Are you saying I can suck your dick when I’m 18?

We’ll see.

That’s what my mom says when I ask about getting my own car. You know you want it. 

Why do you say that?

I’ve seen you check me out just as much as I check you out. I love that hairy chest. I bet you’ve got a big one too. Send me a pic?

18!! I added a cop icon for good measure. 

He didn’t respond to that. But God, he had me worked up. I knew it was wrong and I felt like a dirty old man, but this kid was so ripe… I stripped off my shorts and spit in my hand and started furiously working my cock, forbidden images floating through my mind. Jacob lounging at the pool, jerking his teenage dick in bed, trading blowjobs with his friends in the woods… Two minutes later, I roped out wads of sperm, splattering my T-shirt from neckline to hem.

 *****

A couple of Saturday nights later, I was hanging around the house watching SNL and waiting for Colin Jost on Weekend Update. (I have a thing for dorky smart guys with great hair, sue me.) It was pouring rain outside and I could hear it hammering the windowpanes and roof. Just after midnight, my doorbell rang. I had no idea who it could be and immediately my mind went to the dark side. An emergency? A home invasion attempt?

I went down the hall to the foyer and looked through the peephole. Jacob was standing on the porch, his hair and T-shirt soaking wet. What the fuck? I opened the door.

“What are you doing out in this storm? Is something wrong?”

He just grinned, water droplets running down his face. “Happy birthday to me.”

I looked at my watch. It was 12:01. 

“I’m legal now,” he said. “Can I come in?” He didn’t really wait for an answer, but brushed past me into the entryway. “I want my present.”

“But you’re…” I wasn’t sure what I was trying to say.

“But nothing. I’m 18 now and I can do what the fuck I want. And what I want is you.” He stared at me a moment, breathing heavily from running through the rain, then he grabbed the neck of his T-shirt and pulled it over his head. A beat later, he kicked off his sneakers, then he unsnapped the waist of his board shorts and dropped them to the ground, stepping out of them. He was commando, so now this beautiful young man was stark naked in my foyer, dripping water all over the hardwoods. But my attention was more focused on the hard wood pointing at me from his crotch.

I couldn’t help just looking at him, up and down. His hair was wet and tousled and some drops of water ran down his face, tracing over his collarbone to his nipples. He was legally a man now, but still had some of the physical features of a boy. His cheeks were soft, because his beard was still peachfuzz. His chest was perfectly smooth. His belly was lean, but didn’t have the muscular definition in the abs he would probably gain soon. 

His penis wasn’t boyish though. Six inches of perfectly circumcised meat pointed my way. His shaft was medium girth and capped with a luscious, fleshy mushroom head that begged to be sucked and licked. His cock sprouted out of a thick nest of untrimmed black hair and his scrotum was tight against his balls from the cool rain. He held my eyes for a moment, then came over to me and stood close, so close I could feel his breath on my cheek. He lifted the hem of my polo shirt and ran his hand up my chest underneath it, his fingers finding my left nipple and pinching it. Then he used both hands to pull up the shirt; I raised my arms and he tugged it all the way off. His hand went back to my chest, gently rubbing back and forth across the patch of hair between my nipples.

“So manly,” he whispered. 

Then he lowered his hand and cupped my crotch through my basketball shorts. I was freeballing, so he got a good feel of my stiffening rod. He grabbed the waistband and began to pull the shorts down, stopping as my thick brown bush was exposed. He traced his finger across my pubic hair, then sank to his knees as he pushed the shorts to the floor. 

I was fully hard now, the slightly chill air like a physical touch on my cock. Jacob was eye-level with my six thick inches of manmeat and he just stared for a moment. Then he slowly reached out and traced a finger up the underside of my shaft. Tentatively, he put his tongue out and licked my frenulum. A moment later, he moved forward and tried to take my entire shaft down his throat. He swallowed it quickly and I felt the tip hit the back of his throat as he began to choke a bit. His teeth scraped my dick a little as he valiantly tried to gulp down too much too fast. Textbook signs of an inexperienced cocksucker. He looked up at me as he continued trying to take my cock all the way down.

“Hold on,” I said gently, pulling out of him and gesturing for him to stand up. “Try it like this.”

I took my place on my knees and took the base of his steel-hard cock in my hand. I put my tongue out and gently licked his balls, rolling his tender young plums around my tongue, then gently licking my way up his shaft. I tasted the drop of pre-cum beading in his piss slit. It was as refreshing as a mountain stream. Then I took his mushroom head between my lips and licked it with a circular motion, getting it soaked with my spit. Then I gradually moved down his shaft, inch by inch, warming and wetting his dick with my mouth. His eyes rolled back and he made soft little moaning sounds of pleasure. He touched the top of my head and stroked my hair as I got the last of his shaft moist. 

Then I moved my mouth back so that just his head and the very upper part of his shaft were in my mouth. I wrapped my right hand around the base of his meat and began to jack it as I bobbed up and down on the tip. Here I was, naked on my knees in my foyer, sucking off a neighborhood twink. I didn’t really care what it looked like or what it implied, I just wanted to give him this experience. And he was softly grunting his appreciation.

With my left hand, I reached around and kneaded his rump. His asscheeks had some nice taut muscle, but still had the skinniness of youth. I moved my hand back around and cupped his nuts, gently stimulating them. Then I gradually worked my fingers back to massage his taint, still double-timing his cock with my mouth and other hand. Jacob grabbed my head and rose up on his toes, starting to buck his hips a little and fuck my mouth.

I moved my finger further back his taint and found his anus. As soon as my finger touched his backdoor buzzer, he jumped like he’d been shocked. I could tell from the clinched tightness of his pucker that this was virgin territory. So for all his projected confidence and bravado, it seemed Jacob was quite inexperienced in the ways of man-to-man sex. Suddenly, I knew what I needed to do for him tonight. 

I pulled off his cock and looked up at him. “So you’ve never had anyone explore your ass before?”

He stalled a beat, then: “No.”

“Ever felt another guy’s asshole?” He shook his head. “Not even when you head off in the woods with your buddies?”

“You mean Tyler and Nate?” He snorted. “Those guys are pussies. All they ever wanna do is jack off.”

“You’ll be going off to college in a few months,” I told him, “and a whole world of opportunity to explore sex with guys your age is going to open up. Assholes are going to be a big part of that. You’re going to get and give a lot of pleasure from them.”

“I know,” he said. “I’ve just never had the chance…”

“You’re going to get the chance now,” I said. “Follow me.”

He looked a little nervous, so I reached out and grabbed hold of his erection and pulled him behind me to the bedroom. 

“Wait here just a minute,” I said, as I went into the bathroom and closed the door. I made sure everything in the backyard was clean and presentable, then grabbed a tube of lube out of the medicine chest and rejoined Jacob in the bedroom.

“I’m going to walk you through this,” I said, “and I think you’re going to have fun.” I knelt in the middle of the mattress on all fours, pointing my manpussy right at him. I turned to look at him over my shoulder and he was standing a little slack-jawed, transfixed on the sight of my pucker. “First,” I said, “just take a good look. Go ahead, pull my cheeks apart and look.”

I felt his fingers tentatively touch my ass, then he put his thumbs in my crack and pulled me wide open. After a moment, he lightly touched my hole with a fingertip.

“That’s it,” I encouraged. “Feel that manhole.”

His finger made circles and prodded at my balloon knot.

“Now, taste it.” 

His finger stopped and he seemed uncertain. “Taste it?”

“That’s right, rim me. Lick my asshole. Don’t you want to?”

A long moment, then he whispered, “Yes.”

“Go for it.”

Another moment, then I felt the lightest of touches, like a butterfly landing on my rectum. He flicked his tongue all over, then began to moan a little as he worked it more aggressively.

“That’s it, get in there, Jacob. Fuck my ass with your tongue. Push it in.” As he really got into his rimming, I realized my dick was practically streaming pre-cum. Jacob was a born ass-eater, taking to it like a cat to a bowl of cream. I glanced back at him; his face was buried between my cheeks and he was jacking his cock while he munched.

After a few minutes, he backed off and let go of his dick. “I was about to cum,” he said. 

“Not yet,” I told him wickedly. “You’re going to cum in my ass.”

“What?” He was stunned.

“Do you want to lose your virginity tonight?”

“I’m not a virgin! I’ve done stuff.”

“Well, however you want to define it, you’ve never fucked a man. Tonight, it’s time.” I hopped off the bed and took a Trojan from my nightstand and handed it to him with the lube. “Now, first, get me nice and slick with that. Put some on your fingers and work them into my hole.” I got back into position and Jacob popped the cap on the lube. A moment later, I felt the cool moistness of the lube as he began to work it around, then penetrated me with his pointer finger. “Use two fingers,” I said. “Really get in there.” I wanted him to feel how my hole would open up to accept his cock in a moment.

He slipped both fingers in and thrust them in and out, the lube getting nicely distributed. “Mmm, feels amazing,” I told him. “Now put on the rubber and get it lubed too.”

I heard the package tear and turned to look as he unrolled the condom down his shaft. He squirted more lube on the end, then spread it down. 

“OK, you’re ready,” I said, waggling my ass at him. “I think instinct will take over from here.”

He moved up behind me, holding my hips. I felt the touch of his gloved-up cock press against me, then he pressed.

“Fucking Christ!” Jacob blasphemed as his young mushroom head popped past my assring.

“That’s it,” I said. “Keep going. Just little by little until you’re all the way in.”

Slowly he moved into me. His breaths were quick as he felt a man’s cunt enveloping his fuckstick for the first time. Then his balls came to rest against me and he was completely inside. Then he began to move in and out, guardedly at first, as if he was judging how far out to pull before pushing back in. He used short strokes at first, then began to lengthen them as he realized the added friction increased the pleasure. I kept quiet, letting him find his own way and rhythm. I have to admit, I was also enjoying having this desirable young man fuck me, taking his virginity in the process. His penis was the perfect size – big enough to stretch me a little, but not so big that it was too hard to take. 

Jacob began to growl low in his throat as he pistoned my asshole, then he began to mutter, “Oh, Eric, Feels so good, feels so good, feels so good,” over and over again like a mantra. Then he began to really slam it home in me, giving me the full force of his barely-legal cock as he began to yell out, “FEELS SO GOOD! FEELS SO GOOD!” After a dozen or so of his most energetic thrusts, I could sense his orgasm overtake him. He fell forward onto my back, his dick completely buried in me as his load spilled out in several pulses I could feel ripple in my guts. When he finally finished, he pulled out, panting.

“I was supposed to do it longer, wasn’t I?”

“There’s no set time. Plus you had a lot of buildup. And it felt really good.”

“But you didn’t cum. I want to see you cum.”

I flipped over and sat next to him on the side of the bed. I reached over and touched the tip of the Trojan, still sheathing his cock. I moved my hand down to the base and gently worked it off him. There was an almost absurd amount of semen in it, coating the inside. Ah, to be that young and full of cum again.

I gave Jacob a sly look and worked the used rubber down my cock, fully inserting it. Then I began to masturbate my diamond-hard dick, using his ejaculate as lube. Jacob watched me wide-eyed as I raised my hips off the bed and assaulted my prick with my hand, furiously jacking myself. It only took a couple of minutes, then I exploded into the rubber as well, our loads mixing and threatening to overflow the Trojan. 

After I was finished, I removed the rubber and tied off the end. It was about half full of our combined jizz. I held it up for him to see and said, “That’s pretty impressive.”

I had one more gift for Jacob tonight. I was desperate to fuck his fine young rump, but I knew after all his excitement and having felt how tight he was, I would not be splitting that virgin cunt right away. He needed some work, so I went to my closet and opened a wooden box on one of the shelves. 

I had a collection of three dildos and selected one for him. It was pretty regular-Joe, just average length and width but plenty for him to work with. I went back to the bed and handed it to him with the lube. 

“Work on yourself with this. Go at your own pace and take things slow until you get used to it. But by the end of the summer, you’ll be able to take my dick up your ass like a champ.”

He took it and turned it over in his hands, checking it out. “I can’t wait to feel you inside me.”

“I’m looking forward to it too. But it’s probably about time you headed home – I don’t even want to know what your mother would say.”

“She’s been fast asleep for hours. No worries. Hey – can I have a beer?”

“Not until you’re 21.”

“So it’s fine for you to take my dick up your ass, but you can’t give me a beer. That’s fucked up.”

I shrugged. “Agreed. But you’ll have to settle for fucking for now.”

He gave me a teenage eye-roll and got up. I followed him down the hallway to where he had shed his clothes. As he started to get dressed, I took one more look at his body, seesawing between boyish and manly, and thought of all the things I planned to teach him over the course of the summer…