Jerry Ch. 01: Little Buddy

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Jerry gives his first blowjob.
4.5k words
4.43
28.8k
36

Part 1 of the 10 part series

Updated 06/09/2023
Created 12/29/2018
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Jerry happened to glance out of his second story window as he was straightening up his bedroom. Not that it was terribly messy, but he didn't want to gross out his new friend. Tom was coming over for the first time after his football practice. Jerry hadn't yet been to Tom's house, so he didn't know how his room would compare with his friend's. Anyway, it only took a few minutes to put away the few clothes that had been strewn about. He wasn't a neat freak, but he wasn't a slob like his sister either.

It was his sister that caught his eye with that glance out the window. There she was, laying out in the late afternoon sun. She was wearing a tiny string bikini which barely covered her pert bottom. He frowned when he saw her, but said to himself, "At least she's not naked yet." He looked at her for a full minute and wondered what Tom might think of her.

"I suppose he might like the view," he thought. In fact, he was counting on it. Despite the fact that she was his older sister, he had to admit the sun bronzed young woman laying face down on the towel in the backyard had nice curves. "Well actually great curves," he whispered to himself.

His study was interrupted by the doorbell. "It's Tom," he said aloud. He glanced at himself in the full length mirror on the back of his door. Reflected back at him was a slightly built 18 year old high school senior. Smaller than average with average looks. "That is me," he thought in despair. Then he opened the door and clumsily hurried down the stairs.

Ding Dong ... Ding Dong ... Ding

Jerry reached the front door and pulled it open.

Dong

"It's about time dude!" said a sandy haired young man. Tom stood on the porch as if he were a linebacker. Which he was. His handsome face wore his trademark grin. "I guess it would be too much to ask for a beer?"

"Yeah! It would!" replied Jerry aghast at the thought. "But we have coke."

Barging through the door he forced his smaller friend to give ground. "I guess a coke would be good. I've got to piss" He peered over Jerry looking around for the nearest bathroom.

"Oh, the bathroom is at the top of the stairs. You can't miss it." Jerry pointed towards the stairs and added. "I'll get us a couple of cokes."

"I'll try not to!" Tom quipped. When he saw Jerry didn't get it, he said "I'll try not to miss it! The toilet!"

"Jeez Dude, for a whiz-kid you can be kinda slow." He stated as he began to bound up the stairs.

"Yeah! Well go take your whiz and I'll be up in a sec!" Jerry shot back.

A loud snort of laughter came from the top of the stairs. A moment later a surging slashing noise of a fire-hose stream of liquid shooting into the toilet came from the bathroom. Evidently Tom had neglected to close the door. Jerry reached into the refrigerator, grabbed a couple of cans of soda, and shook his head in amazement as the sound from above went on and on. He went to the sliding glass door to check on his sister Diane. She was still there though she had turned over onto her back. Now her ridiculously pert breasts where prominent. "At least she has her top on," he thought.

He couldn't tell how long he stood there, cokes in hand, but suddenly he became aware that the noise from above had ceased. He shook himself and headed toward his room. He was looking forward to helping his friend with his Geometry homework. Of course, he had taken Geometry as a Sophomore and was now in an Advanced Placement Calculus class, but he really enjoyed looking back at those proofs from the old days. The fact that his tutoring had blossomed into a friendship with the popular Tom was a unbelievable bonus. His nerd friends looked at him with a kind of wonder whenever he received a high five from the handsome broad-shouldered athlete when they passed in the hall.

So with a warm feeling of anticipation he started climbing the stairs. "Sorry I took so long ...," his words stopped when he saw his friend standing in the bathroom with his head thrown back. Jerry's mouth dropped open when his mind registered what he was seeing.

His friend was standing in the bathroom in a team T-shirt and matching red and black baggy gym shorts. To Jerry's eyes he appeared to be huge in the small room. The hamper which was half filled with soiled towels was open. Head thrown back, Tom had one hand held to his face. A small scrap of pink was entwined in his fingers close to his nose. "What in the world?" Jerry asked aghast.

"Damn!" Tom said and sniffed at the fabric deeply once again, before dropping his hand. "Sorry about that. Just couldn't help myself!" His hand slipped into one of the pockets in his shorts quickly and came out empty.

"Hey dude, what the hell? You've been holding out on me!" He stepped out of the bathroom and strode towards Jerry. Before he knew it Jerry was held under Tom's strong left arm as the right hand mussed his red hair. The cans of sofa fell to the floor, bounced and rolled across the hallway into his room. "You didn't fucking tell me you have a sister, little buddy!"

"Och!" said Jerry. Tom had tightened his grip.

"What's her name?"

"Diane." Jerry replied between clinched teeth. The hold didn't quite hurt, but it was far from comfortable.

"How old is she?"

"Older than me." Then after a tightening of the hold Jerry added, "Twenty-one ... she's twenty-one!"

"SWEET" was Tom's reaction to the news. "Is she hot?"

"I don't know." Again that squeeze. "I suppose so!"

"Where is she now?"

A rush of feelings welled within Jerry. Sudden fear for and a desire to protect his sister was among them. Tinged with a tiny bit of what? Jealousy? Since the start of the interrogation his eyes had been squeezed shut. Now he opened them and realized that his face was nearly at the level of Tom's crotch. He struggled against the hold, which only resulted in more tightening. He realized that there was no way his meager strength could free him.

Tom chuckled with good humor trying a different tack, "Come on little buddy. Where is she?" Again he ruffled Jerry's mop of hair.

Jerry's senses were overloaded by the solid body he was pinned against. Its heat made him feel very warm indeed. "Ah, come on Tom! Let me go and I'll tell you." he pleaded.

He crumbled to the carpeted floor when released from his friend's hold. Now at Tom's feet he looked up. His eyes were drawn up to the thing inside the gym shorts his friend was wearing. "No underwear," he thought when he saw the thick hanging penis inside the shorts. How could Tom walk around in public like that. With no supported at all. Especially with such a big thing. Shouldn't he at least be wearing a jock strap? All this flashed through his mind in less than a second.

"Well, little buddy, where's your sister?"

The red head tore his eyes away from the huge penis and to the face so far above him. The face was smiling down at him. The smile seemed to be asking another question as well, "Do you like what you see down there?"

Jerry decided after a moments hesitation it was only fair that he tell. Besides it was the real reason he'd invited his friend over. It was just the larger man's sudden forcefulness that scared him a little. "She was in the backyard sunning herself a few minutes ago." He pointed into his bedroom and added, "Go in there. You can see if she is still there."

"See! That wasn't so hard was it?" his friend asked, reaching out his hand to help Jerry up. A moment later he was back on his feet. Tom gestured with his arm miming, "After you." As the red head entered his room he stooped to retrieve the sodas.

"Oh, I better go and get some more soda, cause these have been shaken up." He turned to head back downstairs, but his friend grabbed him by the shoulders and turned him back toward the window.

"Let's see what the view is like, little buddy."

Jerry walked to the window very much aware of the bigger boy behind him. Sure enough, Diane was still out there. Now she was sitting cross-legged on her towel speaking on her smart phone. She was much less exposed, bending forward at the waist her breasts were hidden. Cascading thick golden blond hair was her only visible charm.

"Um, I was hoping that she was a ginger," came a disappointed voice from behind him. "Like you."

"Set those cans down," Tom said as he ran his fingers gently through the red head's hair.

After placing them on the window sill, he dropped his hands back to his side. He was surprised when his right arm encountered something very warm rubbing against it. "What the heck," he thought. He turned and looked down. "Tom! You're naked!" exclaimed the smaller man. There rising lewdly from his friend's groin was an awakening penis.

Somehow Tom had managed to strip off his clothes in the time it took to cross the room. Tom's response was a denial, "Don't be silly little buddy. I still have my shoes on!"

Half aroused when first seen, the penis grew, stretching straighter. It went from a slightly downward curved appendage to a ramrod straight tower of flesh as Jerry watched spellbound. It twitched with life as it came to attention. It was breathtaking and he felt a little dizzy.

Jerry tore his eyes away from the massive penis. He took in the sight of his friend's muscular body. It was like a wall of smooth warm flesh. He could feel heat radiating from it. He felt himself blushing bright red. Then with a quick glance back down at the stalk that was the rampant erection, he turned away and stared out the window again.

It took a few minutes before his mind was calm enough to see what he was looking at. When he did he saw his sister laying out on her back again. Done with her conversation, she was relaxing behind sunglasses, perhaps even asleep. "She has a nice tan, but she's going to have tan-lines." Tom commented.

"Actually she usually sunbathes in the nude." Jerry replied truthfully.

"That must be hard on you little buddy." the taller man said in a quiet voice.

"Sometimes." Jerry whispered. Especially when he had friends over. They always stood where the two of them where now and stared. Of course none of his other friends would have stripped down displaying their erections. Or if they had, he suspected theirs would not be as large, as powerful.

At some point his friend had wrapped his arms around him. He could feel the heat of the naked body even through his clothes. Jerry had dressed carefully before the visit, choosing a simple but nice button down shirt and his newest jeans. Now because of his nervousness and the real warmth produced by the body contact, he could feel the sweat beginning to mess up his clothes. He was glad he was wearing an undershirt to stop it from soaking through his clothes.

"Tom must have taken a shower after practice," Jerry thought as he caught a whiff of soap and deodorant. He wished he had showered.

"Here, let's get this off." Fingers began to undo the buttons of his shirt from the top down. He thought about protesting, but it would feel cooler. He even reached down and helped by pulling the shirt out from the jeans. Then after the last button had been undone he slid his arms out of the sleeves while his friend held it for him. It was much cooler once it was off.

"Thanks," he said.

In the yard below, Diane had evidently woken from her nap, because she had untied her top and was now topless. "Nice tits!," came the voice behind him. A change in the tone and intensity of the voice betrayed Toms growing interest in the view. Another softer sound made it clear that his friend was taking an interest in something else. His penis. A slow steady sound of skin sliding on skin came from behind.

A drop of sweat rolled down Jerry's forehead ran along his nose and dropped from its tip. He shrugged out of his undershirt and tossed it to the floor. It felt deliciously cool to be free of the damp shirt, even more delicious to be half naked with his friend. His hand moved to the front of his jeans. He felt his hardness through the thick fabric as he tried to secretly rub its length. His penis had escaped his jockey shorts, but it was trapped within the confines of his new jeans. Still as uncomfortable as it was, Jerry's eyes closed as he rubbed the hard bump down his leg.

"Mmm," sighed his friend behind him. "Feels so good doesn't little buddy?"

The red head answered with a nod. Realizing he had been caught red-handed so to speak. He squeezed his penis more firmly, no use trying to hide it now. It would be so much better if he pulled down his pants, but he just couldn't. It would be too embarrassing.

"It'll be better if you lose the jeans, dude," Tom pointed out. "Look at her."

Jerry opened his eyes and saw his sister had slipped off the black bikini bottom. Her legs were closed so her private place couldn't be seen, but enough was visible for them to see she obviously shaved down there. It was something which pleased Tom as his exclamation make clear, "Sweet. Shaved pussy!"

Jerry realized that naked genitals must one of his friend's hot buttons He couldn't get the smooth hairless groin which he'd seen out of his mind. In fact it was only the fear of dying of shame which kept him from turning and studying the huge erection he knew was behind him. He longed to take a closer look at that amazing penis and the shaved balls which hung beneath. Maybe when Tom's attention became riveted on the scene below.

"'What the heck," he thought as he unfastened his belt, unsnapped and unzipped his jeans. He grew redder if it was possible as he began to push them down his slender hips. He looked down and remembered he was still wearing his shoes. Bending over to untie them his butt bumped into Toms thighs.

"Pardon me," he said absurdly polite given the situation. The taller man stepped to his right and Jerry was able to reach his shoes. It took longer than usual to complete the operation because he was distracted by the sound of masturbating so close to him. Finally after almost falling over he managed to remove his shoes. He straightened up and continued pushing off his jeans until he kicked them from around his ankles. Now he was standing in just his underwear next to his naked friend.

Embarrassed? Yeah, but also thrilled and turned on like he'd never been before. He reached into his shorts and adjusted his erection until it stuck out from the elastic band on top. He wondered what Tom would think of it. Probably nothing at all since the naked man was fixated on his sister. She had opened her legs a little, enough to show off her pussy. Tom felt a stab of guilt for thinking of her thing as a pussy, but Tom thought of it as such. He watched until one hand slowly glided from a hard erect nipple, down her flat tummy onto the mound which was her pussy.

"You're a lucky guy, little buddy! Must be nice to have such a gorgeous sister!"

Like the dozen or so times before when he'd had a friend or friends over, Jerry turned away from the spectacle. She was his sister after all. Just like all those other occasions his visitor became oblivious to anything except the sight of a gorgeous woman giving herself intense pleasure. What was different about this occasion was today's visitor was providing a spectacle Jerry could watch. Indeed, one he would savor.

Jerry first hurried to the bed room door, and quietly shut it. Then he turned back towards the window and stared at the beautiful naked athlete who stood before him. Now that he was clearly out of his friend's sight, he felt better about getting naked himself. He slid his underwear off his slender hips, down his skinny legs and stepped out of them. According to Tom's definition he still wasn't naked. After all, he still wore his black dress socks. Gosh he felt so naughty and turned on.

His penis stood at an acute angle to his stomach. Not quite half the size of the bigger man's erection, it was much harder than it had ever been before. So hard it ached. He grabbed it with one hand and stroked it which seemed to help. In less than a minute he had to let go, because he could feel himself about to shoot. It was much too soon for that.

He studied the naked muscular shoulders, back, and buttocks of the man. He studied the strong thighs and huge bunched calves. The sight was like a young Greek god in running shoes. Best of all Jerry was sure he could savor the sight for as long as it took for his sister to climax. It was time to get closer.

"Oh yeah ... finger your cunt," his friend said.

Jerry stepped forward, moving as silently as he could. Once when his knee made a popping noise he stopped, afraid his friend would turn around. Then realizing the man was absorbed in his lustful thoughts and actions, Jerry continued forward until he stood only a couple feet to the left of his target. At last he was able to see the magnificent erection.

"She's got three fingers in it!" Tom exclaimed in amazement.

Seen from the side, even the large pumping fist could not totally obscure it. A good two inches of penis flesh extended beyond the man's circling fingers even when they rose nearest to the tip. An incredible five inches were exposed after a downward stroke. Over and over again, up and down went the hand with a steady rhythm, hypothesizing Jerry with lust. It was the most beautiful thing he had ever imagined, let alone seen.

Bending at the waist, Jerry brought his face closer to the engorged head. He was amazed at the size and shiny red color. As he watched a pearl of clear fluid emerged from the hole at its tip, he found himself leaning closer.

"She's .. so ... fucking ... hot."

The drop slowly sank down lower and lower glistening in the light. It was attached to its source by a thin strand which stretched until it reached the breaking point. The strand snapped and the drop fell to the carpet. His gaze followed its fall. "What a waste," he thought.

How would it have tasted? Would it taste like his own? The questions ran through his mind. He felt himself blush all over again, which was silly. "He can't read your mind," he told himself.

His was drawn quickly back to the cock. "Yes it was a cock," he acknowledged to himself. A wonderfully meaty cock, thick, long and pulsating.

"Mmm ... she ... is ... so ... slutty!" his friend said and something about the way it was said made Jerry realize time was running out. He also noticed a subtle change in the way the man was moving. Instead of pumping his fist up and down, he was now using a back and forth thrusting of his hips. Holding the cock in a motionless hand resulted in the same rhythmic sensations to the organ.

Wanting to memorize every detail of the scene for mental playback at a later time, the red head moved as close as he dared. He took hold of his own throbbing penis, knowing time was short and his hair trigger wouldn't matter now.

"Mmm ... she ... is... about ... to ... cum!" said his friend.

Then Jerry realized he had an extreme closeup head on view of the engorged cock. His friend had turned towards him, confronting him with his beautiful cock. It was there in all its live glory, inches from his lips on its forward thrusts. Whether Tom was aware he was there or not, didn't enter into the mental math which drove Jerry's decision. It was more a question of clean up. If he didn't do it, Tom's mess would get everywhere. At least that is the way his mind rationalized what he was about to do.

Timidly he stuck his tongue out and touched the cock's crown as it came towards him. He was amazed at the heat of it. Then it was gone as the hips that powered the thrust pulled it away. Jerry waited opened mouth for its return.

"Mmm ... I'm ... going ... to ... cum!"

When the cock returned his lips were forced wide, stretching to accommodate the powerful thrust. He was surprised not by the crown's hardness, but its smoothness. He wasn't able to engulf more than the head before drawing back his own head for fear he wouldn't be able to breathe. He found the taste to be overpoweringly erotic. Instead of again pulling away with a backward thrust, the cock seemed to press forward .

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