Breaking Bernie’s Cherry

By Simon Peter

Jake squeezed a generous glob of lubricant into the palm of his hand as he gazed down at the exposed fuzzy butt cheeks between his knees. He rubbed the lube up and down his thick cock shaft and around the mushroomed knob, thinking how sweet this moment came to be, how he had ached for it to come, how he had lusted to grease his cock and bury it into the firm tight cherry butt now inches under him.

But this moment came quite late in the relationship. Bernie wasn’t too excited about anal sex. Both he and Jake had enjoyed each other in a multiple of methods, but anal had not been considered seriously. A couple of hints from Jake, how firm Bernie’s butt is, how sexy his fuzzy cheeks and hairy crack were, how stimulating Bernie looked lying on his back with his legs spread and Jake sucking on his dick and licking his balls and lifting his butt to slobber into his crack. Jake had often rubbed Bernie’s hole, feeling it twitch and squeeze, which had made him mad with lustful desire.

“But you can’t stay virgin forever, Bernie,” Jake said as he lay on his back, his arms behind his head, his flat stomach glistening and heaving after a long session of making out and of a final explosion of his seed down Bernie’s throat.

“Uh…” Bernie said, still tasting the thick cum inside his mouth as he rested sideways on an elbow staring at Jake’s naked body. “You know. No. I guess not. Maybe.”

Jake snickered. “Look at my dick, baby. It’s aching to own you.” In response, Jake’s thick 8-incher quivered.

Bernie moaned, reaching out to grab the semi-hard slimy cock shaft, feeling the veins starting to throb, the cock coming back to life.

“But you’re so big, Jake.”

“Well, you don’t seem to mind swallowing it, babe. You take it all the way to the base.”

“Mouth and throat are different, Jake.” Bernie looked up to meet Jake’s lustful look as Jake’s cock thickened and hardened. Bernie stroked the erecting cock lovingly, lubed with spit and cum. He leaned and licked around the nipples, then followed the hair trail down the belly, took a deep scent off the thick curly pubes, until his reached the cock and hungrily took it between his lips.

Jake moaned, but he grabbed Bernie’s head with both hands and pulled him up on top of him, raising his head to kiss Bernie, tongue deep.

Bernie melted. His own cock was still hard as he pressed onto Jake’s crotch. The two man cocks rubbed and grinded as the two boys kissed.

“You will love it, baby,” Jake had tried his best to sound convincing.

“Jake, it gonna hurt.”

“What’s a little hurt for the pleasure of taking cock the first time? I wanna be your first, Bernie. I wanna break that sweet cherry of yours.”

Oh, Jake,” Bernie moaned, grinding on Jake’s crotch. “Me too. I want you to be my first. I want you to break me. But your fucking dick is gigantic and it scares me.”

“You love my cock, Bernie,” Jakes laughed reaching down to slap Bernie’s firm butt cheek. “As I said, you cannot remain virgin forever.”

This conversation was repeated a few times until finally Bernie acquiesced.

“Let’s do it.”

Bernie had not said this lightly. He had said it with trepidation. He knew that at some time he was going to take cock up his virgin ass, that he lusted to take cock up his ass, but also that the first time was going to be excruciatingly painful, and Bernie hated pain. He had played with his finger every now and then. His ass had twitched and squeezed like crazy and his dick throbbed as he worked his finger in and out and around. But a finger was not a man cock, was no way like Jake’s monster cock. Even when he used the dildo that he had bought some time before to try to feel what it was like, to experiment, it wasn’t too pleasurable, with some pain. Jake’s cock? Oh, God! Bernie had trembled all over as soon as he uttered the words of agreement. He was going to be fucked.

That had been around half an hour ago, Jake thought as he rubbed the lube up and down his cock. He had squirted some inside Bernie’s crack and started to finger the hole, feeling it twitch. They had made out and stripped and kissed and licked until Bernie became so horny that he couldn’t wait any longer in spite of his consternation.

Jake contemplated which position he was going to take Bernie’s cherry. The easiest was for Bernie to ride his cock, taking his time, not forcing it in. But looking down at the naked body under him, Jake decided he would want to own Bernie. He would want to lie flat on top of Bernie and prod his hole, trying to stretch it little by little until it sucked him in. He didn’t want to cause Bernie any unnecessary pain, but he well knew that Bernie will hurt, a lot, once he started fucking him.

Resting on both arms, Jake lay down on top of Bernie, flat, full weight, his cock slipping inside Bernie’s greased ass. Jake moved his hips slowly to hump the slick crack as his mouth found the side of Bernie’s neck. He licked and kissed and humped.

Bernie moaned and squirmed under the weight of his man. He felt the hardness between his ass cheeks and he quivered all over, his hole twitching like crazy. Bernie was scared, but turned on. Jake’s licking and kissing on his neck and shoulder, Jake’s naked hairy chest plastered onto his back, Jake’s arms encircling his chest and fondling his nipples. Bernie was going to be fucked. By a huge cock. Bernie was really scared. Shitless scared. Bernie was also in a fully excited mode. He squeezed his ass cheeks tight around the bone humping his crack.

Jake reached down to fist his cock shaft and guide it onto the spasming hole. He prodded. Bernie moaned. It wasn’t that bad, Bernie thought as he felt the pressure against his ring muscle. Actually, Bernie thought, this felt quite good.

“I love your ass, baby,” Jake whispered as he resumed working Bernie’s neck and shoulder with his mouth and tongue and teeth. “You’re gorgeous, baby.” He repeated over and over.

Bernie pushed back onto Jake’s prodding crotch. He turned his face sideways to meet Jake’s mouth and they kissed. Jake pushed his tongue inside Bernie’s mouth and simultaneously thrust into the hole.

Bernie screamed.

Jake pulled back.

“Fuck! What…?” Bernie cried out, flipping onto his back and throwing Jake off of him.

“Easy, baby. You know it would hurt. Don’t be a wimp.”

“Fuck that, Jake. No way am I gonna take this cock up my ass.”

Jake laughed and climbed on top of Bernie, straddling Bernie’s crotch.

“You will take it up your ass, babe, and you will love it, too,” he smirked, stroking his greased cock. Bernie stared at Jake’s cock inches away from his face, now threatening rather than exciting. This was going to penetrate his body: this huge and thick and hard member was going to pierce and stab his hole, mercilessly no doubt. His eyes shifted up to gaze into Jake’s face, noticing the smirk as Jake stroked slowly.

“You’re fucking enjoying this, aren’t you?” Bernie mumbled.

“Fuck, yeah, baby. I’m hard and ready.”

Bernie squirmed as Jake held him down, sliding back on Bernie’s legs using his knees to spread Bernie’s thighs apart, his cock back inside the crack. Bernie squirmed some more. He looked down between their two naked bodies, and the sight of Jake’s ripped chest, the hair trail, his own dick plastered on his belly, and he thought “what the fuck… let it happen!”

Jake was again prodding the hole with his round knob.

“Relax, Bernie. I’m coming in.”

Jake pressed and started to stretch the tight hole. With a powerful hip thrust, the cock head popped into the rim muscle.

Bernie screamed.

Jake pulled out.

“God, that hurt,” Bernie moaned. “You just broke my cherry, Jake.”

“No, Baby. It was just the head.”

“No fucking way. It felt like a foot of cock went inside my butt, Jake.”

“Turn around, Bernie, on your knees. No more fucking shit from you. Baby, I’m gonna fuck your ass, and you’re gonna take it deep.”

“No, Please, Jake. That would be rape. Please, it’s too painful.”

Jake slapped Bernie’s butt and forced him onto his hands and knees, kneeling behind him and applying more lube onto his throbbing cock and on Bernie’s hole.

Bernie tried to resist, but only half-heartedly in spite of the burning pain in his ass. Only the head? And it was that agonizing?

Grabbing Bernie’s hips, Jake aligned his cock and pushed in. When he penetrated, what came out of Bernie this time was more of a grunt than a scream. Jake held his cock head just inside the rim muscle, leaning on top of Bernie’s back to work his mouth on Bernie’s neck. Slowly, the gripping ring around his cock ridge started to loosen. Unlike the initial thrust, the push into the hole was now slow and gentle, letting the ass suck in the cock shaft.

Bernie slumped down onto his belly, his knees unable to carry the weight as he felt himself impaled. There seemed to be to end to the bone that was ravaging his body. Jake kept the pressure. Deeper. Halfway in, Jake’s cock head hit the inner ring. He pulled his cock shaft and then back in without pushing any further, the ass stretching and contracting with each thrust. He could feel Bernie’s outer ring spasming on his cock shaft and he throbbed and got harder in anticipation of burying into the fuck tunnel under him.

Bernie was moaning loudly, as the thick cock worked his ass. Now his cherry was broken. By beautiful Jake. By beautiful Jake’s cock. His own dick was half-limp but he felt it leaking onto the floor. He so wanted to reach out and stroke, but he felt too weak to do that as Jake kept the rhythm of fucking. Bernie didn’t realize that Jake was not completely in, that it was only half of Jake’s cock that was moving in and out of his ass.

Grabbing Bernie’s throat with one hand, he turned Bernie’s face towards him and started sucking on the lips. His other arm snaked under Bernie’s chest to fondle and squeeze on the nipples as Bernie moaned into his throat. Jake felt the resistance against his prodding cock head loosen. Holding Bernie tight with both arms, he thrust into the inner ring penetrating it and kept the pressure until he buried all his 8 inches of man cock inside the fuck tunnel. Bernie’s grunting scream was muffled by Jake’s sucking mouth.

“Fuck, baby, now your cherry is broken.” Jake groaned.

Bernie was unable to reply, unable to breathe, his body on fire, his ass on fire, his whole being burning with pain, and… “what? Pleasure? Fuck. Oh, fuck” he thought and then whimpered out loud: “Jake, fuck, fuck… me…” That was no finger, no plastic dildo. That was Jake’s cock filling him. He felt the pulsating cock shaft through the pain and he pushed back onto Jake’s hairy crotch to get more of the beautiful cock into him, now that he was ravaged.

Jake fucked. When he finally dumped his load deep inside Bernie’s bowels, he grunted and stilled keeping his throbbing cock in, not wanting to pull out. Bernie lay under him like a rag.

“I love you, Bernie.”

“Jake, oh God, Jake. Keep it in. Fuck me more. Jake, baby. Fuck.”

Jake erected without pulling out and gave the offered ass a pounding that rocked Bernie’s body from head to toe.

Done. Cherry broken. Bowels filled with man sperm. Beaming Bernie. Panting Jake.