First of a multi-chapter story chronicling Jeffry's adventures.
Jeffry and Billy 1 (mm, masturbation, voyeur)
Summary – Jeffry and Billy spy on Billy’s sexy sister and become aroused.
Note – This is a work of fiction, make-believe and sexual fantasy. It is not based on real people or actual events. You must be 18 or over to read these stories. The author does not condone any sexual activity among persons under 18 in real life. Also, the author does not condone unprotected sex in real life. It is OK to have fantasies, but turning a fantasy into reality can destroy lives. Don't fuck with other people's lives!
Billy and Jeffry were friends from school. Billy was almost a year older than Jeffry, but they were still in the same class. Jeffery had started school earlier than he should, while Billy’s parents held him back a year. Being one of the older boys in class, Billy was very confidant, strong and popular. His jet black hair, handsome face, toned body and demeanor marked him as a typical, although young, ‘alpha’ male.
Jeffry was nearly the opposite; being younger, he was smaller than the other boys in his class. He was also, thin, weak, and unsure of himself. He was cute enough, with his unkempt sandy blond hair and dimpled smile, but he was insecure and lacked confidence. Not wanting to ever make a scene, he was a bit submissive and always went along with the crowd. He was just happy to have friends and never wanted to disappoint anyone.
That is why Jeffery and Billy had started hanging out together. They were drawn together. Bill liked to take charge, and Jeffry liked to hang out with Billy and do the things Billy wanted to do, meekly, without question. Billy liked that. Jeffry really admired Billy and tagged along whenever he could. Billy was cool, funny, strong and handsome. All the things Jeffry wished he could be. He so badly wanted to become Billy’s best friend.
However, their friendship changed drastically one hot, late summer afternoon.
Billy had invited Jeffry to go swimming at his house that day. His family owned a large, built-in swimming pool – perfect for a cool dip on a hot, summer day. And the best part was Billy’s parents were rarely home – both of them having demanding jobs that kept them away for long hours during the week-days.
The two friends had a good time playing together in the pool, and even got a bit naughty as they admired Billy’s older sister, Becky. She was sixteen and beautiful. Becky was sunning herself on the pool deck, wearing a skimpy bikini that barely covered her full, round, tits and well trimmed pussy. While she sunbathed with her eyes closed, the boys began goofing around.
Billy thought his older sister was sexy as hell and was always trying to leer at her without being caught. First, Billy made hand gestures as if he was grabbing her breasts. Jeffry stuck out his tongue like he was in the throes of orgasm and started making humping motions. Then, they both pretended they were fucking her and groping her tits. Billy even crept up behind her, grabbed his swelling crotch and humped the air behind her head!
They later whispered together in the corner of the pool, staring at her, and making dirty comments about how they wanted to see her naked. They discussed her hard nipples and admired her prominent camel toe, bragging about how hard they would fuck her and make her cum with their hard cocks.
They both began to get stiff in their swimming trunks but pretended not to notice each other’s growing bulges. However, Jeffry found himself stealing glances at Billy’s crotch, fascinated by the very large bulge that was developing in Billy’s swimsuit. Jeffry began to look whenever he got the chance. Billy’s dick was obviously so much bigger than his own. Intrigued, he began to wonder how big it really was and what his friend’s cock looked like.
Billy noticed Jeffry’s glances and became oddly amused by his friend’s attention. Billy was very proud of his muscular body and his big cock which he knew was longer and fatter than all the other guys at school.
Jeffry’s attention triggered something in Billy. His cock size had always made him feel superior to the other kids, and with Jeffry’s obvious curiosity, he felt proud, superior, and a little more arrogant. He liked the feeling. He began to get even more aroused. Billy decided to show off for Jeffry.
Billy turned his head and pretend to look at something off in the distance with his very chubby cock pressed against his swimsuit. From the corner of his eye, he saw Jeffry staring openly at his crotch. He began calling for Jeffry to watch as he made silly poses, then dove into the water; making sure he nearly lost his swim trunks in the process. He showed off his handsome ass crack by quickly climbing out of the water and letting his trunks fall down and then pull his suit up into his crack before adjusting it properly. As his cock grew firmer, he finished by standing on his hands in the shallow water, his long, hard, lump clearly visible in his tight swim-suit, dangling just above the water line.
Jeffry’s cock became rock-hard watching his friend’s antics and he had to wait until it subsided before climbing out of the pool. Billy’s large cock had quickly become an obsession for him and he felt strangely compelled to see what it looked like. His small penis was never a source of embarrassment to him, until now. He really wanted to see how big Billy’s cock was, especially compared to his meager package. Jeffry quickly devised a plan to catch his friend naked so he could see Billy’s cock.
After they were finished swimming, the two boys headed back into the house. Jeffry followed closely behind his friend to make sure they were together when Billy stripped off his swim-suit. Jeffey pushed his way into Billy’s bedroom before Billy could shut the door.
“Brrr! I’m cold,” said Jeffry, excited and nervous at the same time. He was about to see Billy’s dick!
“Me too!” Billy added. He saw Jeffry glance at his crotch again. He turned his back and dropped his wet trunks on the floor, allowing his friend to gaze at his smooth, firm ass. Billy bent over slowly to pick up his clothes from the floor, letting his heavy balls peak our from below his ass and then quickly whirled around, catching Jeffry staring hungrily at his ass and then watch his gaze shift to Billy’s balls and then his chubby, naked cock.
Jeffry never even looked up. He slowly dropped his own wet suit on the floor, hypnotized by his friend’s nakedness.
“Wow, Billy! Your dick is a lot bigger than mine!” Jeffry said, unashamed. He walked over to Billy and compared their cocks. Billy wasn’t fully erect any longer, but his perfect penis was plump and long, with a thick shaft and fat head. Jeffry’s small cock was hard and stiff and his tiny nuts were shrunken from the cold. The two teenage peckers were a mere foot from each other.
“Wow! Your cock is huge, Bill!” Jeffry said, coming closer and openly admiring his friend’s cock.
“Yours is pretty small, Jeffry. I bet you wish you had a cock as big as mine.” Billy flexed for his friend and thrust his hips; his thick pole flopped up and down. ‘Smack, smack!’ as his cock slapped his belly and then his heavy balls.
Jeffry wiggled his hard little cock back and forth, trying to join in the fun. The two naked boys giggled. Jeffry moved even little closer. He looked at his friend, then his friend’s cock. He was awe-struck. He unconsciously began to reach out his hand. He badly wanted to know what a big cock like that felt like compared to his diminutive one.
“Can I…, can I touch it, Billy?” He looked in Billy’s eyes, seeing him frown as he considered the request.
“Well, I don’t know…” Billy said. He was not gay and he was starting to get a little uncomfortable. He had enjoyed being admired and showing off his cock, but this was different.
“Just for a second, please Billy?” Jeffry didn’t wait for an answer. Something inside of him was controlling him. He was hard and horny and mesmerized by Billy’s cock.
Jeffry reached over and touched it. He slowly slid his fingers gently up and down his friend’s fat shaft. Billy froze.
“Wow…” he said again, staring at his friend’s large cock watching his small fingers touching it. Jeffry’s breath became labored. He licked his lips, nearly in a trance. He slid his fingers down to Billy’s swollen ball sack. “Your balls are huge too!” He ran his fingers over and under Billy’s balls and then cupped his sack with his palm, feeling their weight. “Wow, they are so heavy!” Jeffery caught his breath, nearly shaking with excitement. After fondling Billy’s nuts, he moved his hand back to the shaft, encircling it with his fingers, gripping it softly and began to stroke it up and down like he did with his own cock (though he usually used two fingers, not able to wrap his entire hand around it like he was doing now).
He felt Billy began to harden in his hand. His friend’s cock felt alive as it pulsed and thickened in his soft grip. He traced a finger around Billy’s expanding gland and then gripped it firmly. He began to jack his friend off, becoming extremely aroused.
Jeffry moaned. “Ohhh! It feels is so hot!” He reached out his other hand intending to feel Billy’s balls sack again while he stroked his friend’s hard cock. He wondered how much cum Billy could shoot.
“Hey!” Billy said suddenly. He pulled away, realizing what was happening between the two of them. Jeffry’s hand felt nice, but, Billy wasn’t gay. He felt ashamed for getting turned on and letting Jeffry stroke his cock.
“That’s enough, Jeffry! I didn’t say you could play with my dick!” Billy quickly put on his underwear and shorts, hiding his stiff cock. Jeffry watched his prize disappear, oddly licking his lips as he saw a fat drop of pre-cum ooze out of Billy’s cock-head just before it disappeared.
“Are you gay, or something weirdo?” Billy spat.
“Uh, I’m sorry, Billy. It’s just…, it’s just that your dick is so big, and mine is so small!” He hung his head down, suddenly noticing his nakedness and wilting pecker. He quickly got dressed, feeling ashamed. “I just wanted to know what a big dick felt like, I guess…”
“That was really weird, Jeffry. I think you better go home now.” Billy was confused. Jeffry had made him feel so good, but it was so wrong!
“OK. I said I was sorry!” Jeffry paused and looked at Billy. “You won’t tell anyone, will you?” Jeffry asked.
“Tell people I let you play with my cock? I doubt it, Jeffry.”
Jeffry left quietly. He could feel the wetness oozing from his shriveled dick, cooling in his underwear. He hurried home and went straight into his room. Still feeling horny from perving on Billy’s sister and touching Billy’s cock, he dropped his pants and smeared the remaining pre-cum around his stiffening cock-head.
He vividly relived the experience of touching and fondling Billy’s cock and balls. He remembered how hot and heavy his friend’s cock and balls felt while he jacked his own painfully hard, thin shaft. He licked his slimy fingers and wondered if Billy’s pre-cum would taste the same? He stroked himself, fantasizing and imagining the two of them had done even more sexy acts. He quickened his tempo as he imagined Billy urging him on. “Oh, if feels so good! Do it some more, Jeffry! Stroke my cock, play with my big balls, Jeffry, make me cum!”
His fantasy intensified; he could still feel Billy’s cock pulsing and throbbing in his hand. He imagined Billy reaching out and gripping his own hard little dick. He stroked Billy faster and imagined his hard, fat cock growing thicker and harder in his hand. He imagined that Billy began to moan and then started to cum; his friend’s thick cock was spurting forcefully in his hands and arcing into the air, splattering thick cum everywhere; on his hands, his arms, his chest, his face! OMG!
Jeffry was furiously jacking his own cock and began spurting his own boy juice. Spurt after spurt landed on his belly and covered his fingers with thick, white goo. His orgasm was huge, and he smiled to himself as he felt the warm cum quickly cooling on his body, his chest heaving.
“Wow that was awesome!” He knew he was going to have many more orgasms thinking about his friend’s big cock. He licked his slimy fingers as he began cleaning up his cummy mess. He found himself wondering what Billy’s cum tasted like? Would it taste like this? Maybe Billy would let him touch him again? He knew Billy liked it when he was stroking his shaft. Maybe he could convince Billy to do it again? Maybe he could offer to do a little bit more to make his friend feel good? He licked his lips and thought about what his next fantasy would be…
Billy was horny too. He had tried to ignore it after his friend left, but playing around in the pool, fantasizing about his hot sister, and having Jeffry play with his cock was too much for him. He was soon naked on his bed, his stiff cock in his hand. He didn’t want to admit that his friend had gotten him aroused. He began to masturbate and tried to fantasize about the girls in his school, imagining their firm titties and tight pussies, trying to drive away the images and feelings of Jeffry stroking his shaft.
However, when he thought of the girlish hands stroking his fat cock, the image quickly shifted, and Jeffry was stoking his cock again. He imagined red lips sucking his dick and licking his cock-head, but it was soon replaced by images of Jeffry sucking his cock; longingly and lovingly, with those halves-closed, cock-hungry eyes. As Billy continued stroking his cock, feeling his orgasm build, he realized that Jeffry would have continued jacking him off until he came. Jeffry really admired his cock. No, Jeffry wanted his cock. In fact, Billy came to the obvious conclusion that Jeffry would probably do anything just to get his hands on his cock again.
Billy suddenly realized he could easily manipulate his weaker, timid friend and make Jeffry do things for him that Billy could never get the girls at school to do. Sex things. Why, now that he thought about it, he was sure he could turn Jeffery into his own perverted, sex toy and make him do all kinds of sex things. Nasty, perverted sex things, if he really wanted him to. He recalled how badly Jeffry wanted his fat cock. He remembered the look in his eyes, his moans, and his obvious sexual hunger. Billy began to jerk his throbbing cock harder, imaging Jeffry on his knees, admiring his cock, telling him how awesome it was. Jacking him off, then sucking his cock. It felt a little gay to him, but then, he had an idea. A fucking great idea! What if he pretended Jeffry was a girl? He had the body and long hair for it. Yeah! He could make the little cock-craving pervert wear red lipstick and even panties too! That way, Billy could pretend he was having sex with a real girl instead of a weak-willed, cock-sucking, faggot, sissy-boy-toy!
“Suck it!” he cried. “Suck my cock, Jeffry, you fucking faggot!” In his mind, Jeffry was wearing panties and a bra, with bright red, very slutty, cock-sucking red lipstick. Jeffry’s panty covered ass wiggled happily as he slurped on Billy’s cock. He was going to get a blow-job. A real blow-job! Billy felt the cum surging up his fat shaft. “Ah, take it…, take my cum, Jeffry!” Hot cum blasted from his cock-head as the orgasm rolled over him. His first shot ejected forcefully from his cock in a tall, wide arc that landed on his upper chest. His large balls tightened again and his prostate squeezed repeatedly, sending spurt after spurt of hot, thick teenage splooge erupting from his balls, shooting into the air and covering his naked body. The last few spurts pumped weakly from his cock, then even more oozed thickly from his piss-slit and dripped down to his now emptied balls. He smiled contentedly, breathing heavily.
Finally, he said aloud, in a commanding, haughty voice, “Now…, lick me clean, bitch!”
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