gay first time, coming of age, romance

A young man loses it…

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Cherry

Jimmy lay face-down on the bed, his head turned almost 90% and resting on the pillow. He stared at the wall, waiting.

Behind him, Theo rested, his weight supported on his forearms, and his curled toes in a push up position. Jimmy felt the insides of Theo’s calves brushing against the outside of his own. Theo was a little hairier than Jimmy, with a soft,  light brown coloured down all over his legs, but neither of them were particularly hirsute.

But it wasn’t the warmth of Theo’s legs or the light hair on them that occupied Jimmy’s attention; it was the hot object pressing between the cheeks of his bottom. Jimmy felt almost unnaturally aware of every detail of the penis pressing gently against his hole. He’d seen it before he laid down. The glans was large, shiny, smooth, and surprisingly dome-like, partially hidden beneath a soft, loose foreskin.

Jimmy had been first to undress. He wondered if he was being too eager. He stood naked, resisting the urge to cover up his shaved groin. This was his first time naked in front of anyone sexually, but a lot of the coolest guys at school shaved their dicks, and Jimmy had instinctively mimicked them.

His own penis was very different from Theo’s. It was tightly circumcised, with a rocket-shaped head that was much smaller than the shaft. It was impressive even when it was flaccid; five-and-a-half-inches of brown floppy flesh, bouncing above a pair of plum-sized nuts in a soft bag.

Theo looked down at his groin and grinned.

Jimmy looked down at Theo’s cock as he undressed. It was still soft, but just the sight of it excited him wildly, filling him with desperate adolescent lust. His cock rose in half a dozen heartbeats, then continued getting harder and harder.

“Like what you see?” Theo asked.

Jimmy swallowed hard, then licked his lips lightly, his gaze fixed on his friend’s cock.

He nodded.

“How big does it get?”

“Little bigger,” Theo responded, taking his meat in his fist and slowly pumping.

It didn’t take long to respond, quickly filling with blood. He let go and allowed Jimmy to see its five-and-a-half-inch length.

“It’s beautiful,” Jimmy said in a low, reverent tone.

“Thanks bro. Nowhere near as big as yours but it works just fine.”

Jimmy’s cock stood up at the kind of angle that only the horniest of young men could achieve.

“It’s not how I imagined it would be.”

Theo grinned.

“You’ve been thinking about my dick?”

Colour flared on Jimmy’s cheeks and he grinned bashfully.

“Yeah. Few times. More than a few.”

Theo moved close, and their dicks bumped, like the booms of two small yachts swaying against each other. Jimmy almost came right then and there, as he felt his friend’s cock bounce against his own. The weight and mass of it, though not exceptional; considerably smaller than his own in fact, made the reality of the situation more tangible. He’d never imagined the thrill he would feel at the mere act of feeling his friend’s cock nudging his own.

Theo looked down at him with warmth. He was just a year older, but there was six inches in difference between their heights. Jimmy looked up like a baby bird waiting to receive food from its mother. Theo opened his mouth and their lips pressed together, then their cocks. Theo pushed his groin forwards, and Jimmy rose on tiptoes, grinding his. Theo’s tongue entered his mouth. It was hot and slippery with an aftertaste of mint.

They tongue wrestled slowly for a few minutes, and Jimmy almost passed out from the pleasure of it. He was willing to let his friend fuck him, just for the experience of having Theo inside him, but this cock-pressing, lip-grinding kissing was more than he had hoped for. They had been friends a few years, but Jimmy assumed that the deep affection he held for Theo was one way. He’d never dared hope that it might be reciprocated in anything more than a mano-a-mano, rough-and-tumble kind of way. And now, Theo was showing him the kind of tenderness that he had only dreamed of.

Jimmy stepped away, and Theo frowned, bewildered.

“What’s wrong?”

Jimmy grinned sheepishly.

“Nothing’s wrong. It’s great. Better than great, but I’m gonna nut if we keep kissing.”

Theo looked down at Jimmy cock. It was straining upwards so hard, and a fine, clear string of precum dangled from the end. Jimmy’s nuts had pulled up so high that they rested on either side of the root of his shaft, compressed tightly within his bag. Theo reached down, and rubbed them gently with the tips of his first two fingers.

“Nuts gonna disappear inside you if they get go any higher.”

“You make me crazy horny.”

“So why didn’t we do this a long time ago?”

“I didn’t know if you; if you were interested, and I didn’t wanna lose you as a friend.”

“And I didn’t want you to think I was using my age to pressure you.”

Jimmy grinned.

“Dude, it’s only a year.”

“Yeah, but still…”

Jimmy’s hard dick twitched, catching Theo’s attention. He glanced at it grinning.

“You ready,” he asked.

“Will it hurt?”

“I don’t know. I only fucked a few times, and he never put his dick in me. I was always the one who did him.”

“Was that with Mark?”

“Yeah. You guessed?”

“You were besties when we met. You still think about him?”

Theo shrugged and smiled softly at the fond memory.

“Course. He was sweet. Kind. We were just out of junior high. I missed him when his family moved. Then you and me started getting closer. But I’ll always have good memories of him. You’re not getting jealous already are you?”

“What, whu… what?! Jealous? No, not at all,” Jimmy said flustered. “Well maybe just the tiniest bit.”

“You don’t need to be.”

Theo moved close and their boners brushed again. He gave Jimmy a gentle kiss on the cheek. Jimmy smiled happily as his friend stepped back, and squirted something onto his palm.

“What’s that?” Jimmy asked.

“Lube. I bought it at the drug store when you said you wanted me to fuck you. I figured it would make it easier for you.”

He smeared it on his dick, unsheathing his glans.

“Big helmet,” Jimmy said.

“I don’t think so really. It’s just that the rest is thinner.”

“Oh. Shall I lay down?”

“Unless you want me to do you bent over the desk?” Theo asked, smirking.

Jimmy grinned back.

“That wouldn’t be very romantic.”

He lay prone on Theo’s bed, his boner pressing up against his stomach. Theo lay on top of him, his own hard penis sliding between the crack of his friend’s bottom cheeks like a perfectly fitting woodwork joint. Jimmy let out a shuddering sigh of contentment, turning his head to the side. Theo kissed him tenderly on the back of the neck.

“You like romance?” Theo asked.

“With you, definitely. Is that really gay?”

Theo chuckled.

“Dude, my dick’s resting in your butt cheeks; I don’t think we could get more gay.”

Jimmy grinned.

“Hah, guess not.”

Theo kissed his neck tenderly again then lifted his body off his friend. He reached down and spread Jimmy’s cheeks, positioning the head of his penis so that it touched the exposed sphincter.

“Ready?” he asked.

“Uh hmmm,” Jimmy responded.

He was apprehensive but also excited. The warmth of Theo’s body gave him a deep sense of happiness and closeness. Then Theo started to lower his body.

Jimmy looked at the wall, evaluating every second of the experience.

“Relax. It goes in easier,” Theo suggested.

He supported himself on one hand and tenderly stroked Jimmy’s long dark hair away from his face. Jimmy strained to look over his shoulder, giving his friend a warm smile. Theo smiled back.

Jimmy let out a long breath, forcing himself to relax as the air left his body. At the same time, Theo lowered onto him, his cock sliding inside as though pushing the air from him. It went in easily, with just the slightest hitch as the glans breached Jimmy’s sphincter. Then the rest slid smoothly in, all the way, until Theo rested on him with the concave curves of his groin, matching the convex of Jimmy’s bottom.

“You alright?” he asked.

“Yes. Are you all the way in?”

“Uh huh. How’s it feel?”

Jimmy sighed.

“Wonderful,” Jimmy said.

He was aware that it wasn’t a very cool teen word to use. He should have said “sick” or “phat” or “on fleek,” but it was the only word that expressed the glow of pleasure he felt and he didn’t care about trying to impress Theo.

“I can feel you filling me up.”

“That’s good.”

“And I can feel your helmet pressing my insides.”

“How does that feel?”

“Weird. Like it’s making me want to piss. Or jizz. But also pushing against my organs. It’s… well weird. Unique.”

Theo lay fully on top of him now, the curves of his belly pressing against the arch of Jimmy’s back, his chest pressing between Jimmy shoulder blades. Jimmy let out a long groan as the air was pushed out of him.

“You okay?”

“Yeah, it feels great being so close.”

“Dude, I’m inside you. Don’t get any closer than that!”

Jimmy focussed his attention on the hard organ that filled his rectum.

“Yeah.”

Theo started slowly pumping, moving just his groin, maintaining constant contact with the rest of his body. Jimmy closed his eyes, while his mind ascended to heaven. The feeling of giving himself completely to the person he cared so much about, was satisfying; almost spiritual. He could feel the hard cock sliding up and down along inside his rectum, the enlarged glans making every millimetre of its passage known.

“Do you want me to do anything?” he asked Theo, his eyes still closed.

“Like what?”

“I dunno, squeeze or push back or something?”

Theo stopped pumping and lay on him again, peppering the side of Jimmy’s peach fuzz covered neck and cheek with tender kisses. Jimmy could feel his friend’s warm breath.

“Dude, you’re perfect the way you are. You don’t have to do anything else.”

Jimmy opened his eyes and looked over his shoulder, beaming with happiness.

Theo started pumping again, initially keeping his stomach pressed to Jimmy’s back and pumping his hips sinuously, then lifting his entire body onto straight arms, gradually increasing his tempo.

“Your dick is so nice,” Jimmy murmured. “It feels so good inside me.”

“Not hurting at all?”

“No, not at all.”

“See, told you it wasn’t big.”

“No, I didn’t mean…”

Theo cut him off.

“I was just kidding Jimmy. I’m totally cool with the size of my dick.”

“It feels so good.”

“Mind if I go harder?”

“Sure. Go for it.”

Theo increased his pace from a leisurely one stroke per second, then one-and-a-half, then two. His breathing became audible.

“You’re sweaty,” Jimmy observed.

“Yeah,” Theo panted.

His pace increased as he hammered into Jimmy’s virgin asshole. He exceeded three strokes a second, aggressively pounding the hot hole beneath him. Jimmy started grunting softly as Theo repeatedly smashed down on him, driving his pelvis into the mattress.

Theo was like crazed thing now, adding his own louder grunts to the mix, as the slippery heat surrounding his cock drove him wild with excitement.

He arms started trembling under the strain of supporting his weight, and he managed to find even more speed for a few seconds as he felt the physical elation flowing from his brutally hard pole. The cum surged from him, flooding into Jimmy’s body.

And then it was over. Theo’s energy left his body as quickly as his cum had. He let out one long sigh and collapsed on top of his friend with all weight.

Jimmy lay pinned like a trapped animal beneath him, but it was a confinement he was ecstatic to experience. He lay, eyes open now, a gentle smile on his face, looking at the wall. There was a game poster there; Grand Theft Auto. He didn’t know it at the time, but he’d forever have a positive association with the game; reminding him of the night he lost his cherry to his best friend.

Above, his friend was dripping with sweat in the warm spring night. It ran off him in rivulets. Their squelching bodies were pressed tightly together. Theo lay, breathing heavily, his consciousness temporarily elsewhere in the post-orgasmic fuzz. Jimmy was happy to lie on his stomach, with his friend’s exhausted face resting near his, their slippery bodies pressed together. He could feel Theo’s continuing hardness deep within him, and it gave him a feeling of unity with his friend that he had never imagined possible.

Theo’s breathing gradually slowed, then his eyes flickered open.

“That was fantastic. You okay?” he asked.

“Yeaaah,” Jimmy said dreamily.

He resisted the urge to declare his love for Theo on the spot. He didn’t want to scare him off.

“Your dick feels so nice.”

“It does?”

“Yeah. It’s like we’re almost one person. No, not that; that sounds dumb. It’s just; well; I can’t think of the words but it feels great to be this close to you. Feeling you inside me; making you feel so good; well, it just makes me really happy that’s all.”

Theo kissed his neck repeatedly.

“Makes me happy too. Look sorry I came inside you. I should have asked first.”

“I’s cool. I was glad you did. It’s like another part of you in me. I hope it melts into me, then I’ll have you with me all the time.”

“Dude, I didn’t know you felt like that about me.”

“Yeah, you’re… you’re terrific.”

Jimmy struggled to express his feelings without using overly romantic or clingy language.

Theo snuggled against his back.

“Was it good for you too?” Jimmy asked.

“Dude, you have to ask?! I’ve never cum so hard. I totally blacked out at the end.”

Jimmy grinned at the wall.

“That’s good.”

Theo clambered off, his erection losing its hardness. It pulled out with a slurp, and a quiet popping sound.

Jimmy made a sound of disappointment as he felt the turgid glans pass by his sphincter like a cork unstoppering a bottle.

“Ohh.”

“What’s up?”

“I liked the feel of you in me.”

“I’m losing my boner.”

“Yeah, but I can still feel your warmth. Now I feel empty.”

“We can do it again. Lots of times if you want.”

“Yeah, definitely. Now?”

Theo chuckled.

“Dude, I think I just blew a month’s worth of spunk. No way I could go again now.”

“Yeah, course. That was dumb.”

“Not dumb. Sweet. I love that about you. Come on, your turn. I’ve never been fucked before, but you can if you like. Just don’t go too hard with that boa constrictor. Or I could give you a BJ?”

Jimmy grinned.

“It’s not THAT big. Eight inches. Anyway, you don’t have to worry.”

“What do you mean?”

“I already came.”

“You did? When?”

“When you started making those grunting noises and going fast.”

Even though Jimmy was still facing the wall, Theo grinned sheepishly. He gripped his friend’s pelvis and rolled him away from the bed. Jimmy’s cock was still fiercely hard. It sprang up, free of its confinement against the bed.

Where the head had been pressed into the duvet, there was a wet patch as large as a dinner plate, with a glistening creamy puddle in the centre, soaking in.

They both looked down at it.

“Sorry, I messed your quilt,” Jimmy said.

Theo grinned.

“I don’t care about the mess, but dude, how much did you cum?!”

“Dunno, but it went on for a long time. It was nice. I never had someone in me before. I’m glad you were the first.”

“So am I.”

Jimmy lay on his back looking up at his friend, his thick, still-hard dick lying on his stomach, balls a little looser now at the base. His genitals were a golden colour, much darker than the rest of his skin.

Theo looked down at him smiling, and picked up Jimmy’s cock in his fist.

“Jimmy, I’ve been hoping for this forever.”

He leaned forwards and kissed Jimmy’s helmet, and Jimmy let out a trembling sigh of pleasure.

“Yeah, me too.”