Jerry Ch. 04: Team Work

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Jerry gets double teamed.
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4.59
15.5k
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Part 4 of the 10 part series

Updated 06/09/2023
Created 12/29/2018
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Jerry Ch. 4: Team Work

Disclaimer: It should come as no surprise to anyone who has read any of the previous Jerry stories what themes will feature in this one. Gay and Bisexual actions feature strongly. Even those of you who enjoy those aspects may be put off by an incestuous twist or a touch of cross dressing. Also at the risk of spoiling the story, anyone afraid of a little romance might want to skip this one.

Apologizes may be in order to my fellow nerds out there. Remember this is just a silly story. Any resemblance to any real nerds is coincidental.

On with the play.

-----------------

"Wow I can hardly believe this is my room!" Diane said when Jerry arrived at her door.

Just returned from taking the vacuum cleaner back downstairs, Jerry hoped she was satisfied with the job he'd done. He watched his gorgeous sister twirl with arms outstretched like a dancer might do. She was a dancer after all.

"It's so clean, it feels twice as big!" she said with a big smile.

"So, you like it?" he asked.

"Yes! I can't believe the difference it makes," she replied. "It is too bad it can't stay this way forever," she added.

Jerry knew that was impossible. She was such a slob, the room would back to its usual mess in a matter of days, not weeks.

"So, will you do it today?" he asked, impatient for her decision.

"Well, you did a nice job. I have to admit, but ... like I said, it would be nice if it was kept this way," she said with a coy smile.

"Okay! I'll do it! Jeez." He gave in to her hard bargaining.

It required two evenings of work to clear up the huge mess. Both of them spent largely in sorting and washing the vast quantity of clothes piled around the room. Those clothes were now neatly hung up in her closest or carefully folded in her dresser.

He wouldn't want his sister to know the pleasure he enjoyed while putting the dresses away. Pleasure made possible because both his sister and mother worked those evenings. This meant he was alone in the house with permission to handle the sexy outfits. Even with the fun as an offset, it was a huge job. With the big clean up done it would only take him a few minutes a day to keep the room clean.

"Thank you!" She hopped up and down, smiling at him with joy. In her delight, she looked years younger than her age of 21.

"So, will you do it? Today?" he asked again, unable to keep the pleading tone out of his voice. He was again the little brother begging his big sister for something she had that he wanted.

"If it will make you happy," Diane said.

"Great!" the slender 18 year-old exclaimed. "He will be here in less than 20 minutes. I'll let you get ready."

With that Jerry left her room and entered his next door. He wanted to clean up and change into more comfortable clothes. He knew his friend Tom would arrive wearing gym shorts and T-shirt like always, so he decided to wear them as well. They would be much easier to get out of than his jeans.

He stripped off his school clothes, button down shirt, white undershirt, dress shoes, black socks, and the aforementioned jeans. Standing before the full length mirror on the back of his door, he studied his reflected image. Short, skinny, with red-hair, he knew he was nothing special to look at, but Tom didn't seem to mind. At the thought of Tom the small penis reflected back at him began to stiffen.

Remembering time was short, he hurried to the bathroom at the end of the hall. He gave himself a quick wash at the sink, paying particular attention to his armpits, crotch and crack. He rubbed some of his sister's deodorant on under each armpit. Someone looking at him might notice that he was remarkably hairless, but it was his natural state so Jerry thought nothing about it. As fresh as he could be without taking a shower, he left the bathroom and reentered his room.

It only took a minute or two for him to dress in his brand-new gym clothes. He was excused from PE so he got them only in the last week. This was the his first opportunity to wear them. The same went for his tennis shoes, they were dazzling bright white, brand new.

Before putting them on he slipped his feet into a pair of little pink ankle socks. He found them tucked inside a pair Diane's old gym shoes when straightening out her closet. He liked how cute they looked and once the tennis shoes were on they couldn't be seen anyway.

When he stood before the mirror again he noticed his shorts were short. They didn't cover down to below his knees like Tom's did. They ended at least six inches above his knees. He came to a horrifying realization. They were girls shorts. His legs were skinny for a man, but not bad for a young girl. He blushed, totally embarrassed. At least he'd been right about the socks. They were low-cut enough they didn't show.

He was thinking about changing back into jeans, when he heard the doorbell.

Ding Dong.

He quickly checked to see that the door to Diane's room was open a crack, then hurried down the stairs. The friction of his naked penis against the fabric of the gym shorts was maddening. He felt his member harden until a noticeable bulge appeared in the shorts. He couldn't understand how Tom was able to walk around in public without underwear, but knew his friend did just that.

Jerry should have known it wasn't Tom at the door. The doorbell wasn't ringing impatiently. If it was Tom it would be. He didn't realize his mistake until after opening the door wide. This allowed his nerd friend, Sidney, an unobstructed view of his new outfit and his aroused state.

He couldn't help but think of Sidney as a nerd. They were part of the same chic of high-school outsiders, but Sidney was the nerdiest of them all. He was obsessed with public transportation. Could you get more nerdy than that?

"What are you doing here?" Jerry asked the tall, skinny, bespectacled black teenager who stared with opened mouth.

"I thought we'd do the usual, you know, thing," said the awkward lad. "You look ... different, but nice," he added staring at Jerry from head to toe. He seemed fascinated by Jerry's naked legs.

"Thanks," Jerry replied absently, polite as ever. "No, I told you that I was tutoring Tom in Geometry this afternoon."

"You have an erection. Is your sister outback as usual?" Sidney asked pointing out the obvious fact of Jerry's boner like the nerd he was. No judgment, no emotion just the fact stated in a neutral tone.

"No, she isn't sunning herself anymore. It gets too cold for her," he said truthfully. He didn't feel obligated to tell the nerd his sister was going to put on an indoor show.

"Then why do you have an erection?"

As if specifically summoned for the purpose, the deep rumble of Tom's Trans-Am announced his arrival. It gave Jerry an excuse to ignore the uncomfortable question.

"Well, Tom's here so you better go," he said.

"Why do you have that erection?"

One thing everyone knew about Sidney, once he got an idea in his head there was nothing on earth which could shake it out again. Whatever it was had to be dealt with before he could move on.

"I don't know. Sometimes it just happens," Jerry said with a shrug.

"What just happened?" Tom asked in his deep voice. "Hey there ... er, Sidney isn't it?" he greeted the nerd and to Jerry's chagrin, put a big arm around the shoulder of the unwelcome teenager in his friendly way. By doing so, Tom seemed to be including him in whatever would come next.

Though only slightly taller than the black teenager, Tom's powerful build made the 18 year-old seem boyish in comparison. The nerd awkwardly shrugged off the bigger man's arm. Jerry knew Sidney didn't like to be touched. The nerd was unmoved by the honor given to him by Tom's gesture.

"I was asking Jerry why he had an erection. He said it just happened," the nerd answered.

After quickly checking out the evidence for himself, Tom asked, "Well little buddy, what's your story?" The handsome sandy haired athlete flashed his trademark grin.

The slender redhead felt his face grow hot from embarrassment. Nothing was going according to plan.

"Okay if you must know, I'm not wearing underwear and the friction -"

Holding up one hand in a "Stop" signal Tom said, "Enough! Going commando! Nice. Well that clears up the mystery!"

"Why aren't you wearing underwear?" asked the nerd, the old question replaced with a new one.

"All right, while you two hash that one out, I have to piss!" said Tom.

He brushed aside the slender redhead and once inside the house immediately went upstairs. He already knew where the bathroom was located. Unfortunately by moving Jerry out of the entrance, Tom allowed the nerd in.

Jerry watched as Sidney strode through the living room and into the kitchen. The redhead followed and watched his nerd friend walk to the sliding glass door. Evidently the nerd didn't believe that Jerry's sister wasn't out there taking in the sun.

From the upstairs bathroom came the sound of a powerful stream of urine hitting the pool of toilet water as if shot out of a fire-hose. As usual Tom left the bathroom door open while he took care of business. As usual the noise went on and on.

"Do you want a soda?" Jerry asked pretending he wasn't annoyed by Sidney's doubt.

He took a coke out of the frig and brought over to Sidney. "Here."

His friend continued to stare out the door as if staring would make the lovely young woman magically appear. Finally the nerd turned and took the can from Jerry's hand.

"Did you wash it?" he asked.

"I forgot," Jerry said truthfully.

His friend always freaked out if he drank from an unwashed can. It was necessary for the wash to be thoroughly done. Not just the top where his lips would go, but the sides and bottom of the can as well. It was one of Sidney's things. Jerry was about to take the can back to wash it when he noticed the splashing noise had ended.

"Could you take care of it this time, please?" he asked,handing the can back to Sidney.

Once Sidney was at the sink focused on the can, Jerry was able to slip away unnoticed. He figured he would have at least five minutes before the nerd got rid of all the germs. It was enough time to see if at least part of the plan was working. He would still have to think of a way to get rid of the nerd, but he was sure he could think of something.

The bathroom was empty when he reached the top of the stairs and Diane's bedroom door was opened a bit wider. Wide enough he could see his sister laying atop her bed wearing a short translucent baby doll. Jerry's penis which had subsided somewhat dealing with the nerd, rose again.

His arousal wasn't caused by the sight of a sexy woman, with long naked legs and pert breasts visible through the nightie. It was caused by his memory of slipping into the same garment the previous evening. He remembered how it felt light as air on his flesh and how exquisite its soft caress felt on his throbbing penis.

If he hadn't known better he would have sworn his sister was asleep. She appeared as an innocent. At least as innocent as a sex goddess in black negligee and lacy panties could look. Jerry thought the panties looked sexier than his sister's naked sex. He would have to try them on at his first opportunity.

With her long honey-blond hair like a fan around her head, she lay on her back with her legs slightly parted. Would Tom believe this was the usual way Diane dressed for an afternoon nap? Had she gone too far? Would Tom suspect a set up? These were questions which flashed through his mind as he gazed on the bronze tanned figure. And where was Tom anyway?

Only one step into the room was needed to discover Tom's gym clothes. The shorts and T-shirt his friend had been wearing were there on the floor at the foot of the bed. Jerry's heart raced a little faster knowing he would find the athlete naked.

After taking another step, he was able to see around the out-jutting wall of the closest. Standing in the corner formed by the far wall and the closet door he found the god to match the goddess on the bed. Jerry caught his breath at the beautiful sight.

Tom was naked, except for his running shoes. His body was large and powerful. He was broad shouldered with a wide chest. It was truly a man's body at odds with the handsome youthful face set atop it. It seemed more glorious than Jerry remembered it. What drew the redhead's attention was the big man's rampant cock. Tom had a full fledged cock, which was easily twice the size of Jerry's penis.

He noticed Tom waving his arms about and realized his friend wanted something. Jerry made eye contact. Tom flashed his trademark grin, then mimed the removal of his clothes and pointed at Jerry.

Jerry blushed, but hesitated only a moment before taking off his T-shirt. This revealed his boyish skinny chest, so unlike Tom's athletic manliness. He used his toes to kick off his tennis shoes. He nervously drew in a deep breath and slid the shorts off his hips. They shimmed down his skinny legs to pool at his feet and he stepped awkwardly out of them. He looked down to see his penis standing small, but proud at an acute angle to his tummy. He felt his face must be as red as its tip.

Jerry tried to make eye contact again, but found his friend's were looking down. Tom was so much taller he was always looking down at Jerry even when looking into his eyes. Tom was looking lower, much lower. To Jerry's relief Tom wasn't looking at his puny penis. He was starring and smiling at the pink socks. Jerry had forgotten all about those. Now he was truly embarrassed. Tom looked into his eyes, gave a friendly wink and a thumbs up sign.

Tom went back to what he'd been doing when Jerry first caught sight of him, masturbating. The athlete turned to stare at the nymph on the bed, seeming to forget about the redhead. Jerry felt he was successfully passed the point of maximum embarrassment and crept closer to his friend. With the big man fixated on Diane, Jerry would be able to stare all he liked at Tom's huge cock.

Before he knew it he was within the long reach of the nearest of Tom's powerful arms. He became aware of the fact once a big hand grabbed one boney shoulder. Tom pulled him in against his massive nakedness. It was swiftly, but gently done, surprising from such a big man.

As he felt the arm wrap around his back and enfold him, Jerry couldn't help but sigh. He closed his eyes and leaned his head against Tom's right pectoral. He was struck by the heat of this wall of muscle, bone and flesh. He was also enchanted by the scents thrown off by Tom's body, soap, deodorant, shampoo and beneath those the faint aroma of sex. Even with his eyes shut Jerry could tell his friend was jerking off, there was no mistaking the movements.

"You smell like a girl," Tom whispered to him. "I like it."

Jerry was glad he chose to use his sister's stuff, and even happier that Tom noticed. He twisted his upper body until he could look up into his friend's eyes. They were the most amazing blue.

"Thanks," he replied in a softer whisper, his face tilted up to the handsome face above.

Time seemed to stand still for long moments, but logic and senses put the lie to that notion. Jerry was intensely aware of the beating of both their hearts. He felt a drop of nervous sweat from his armpit run down his side. He could hardly believe it, but he reached up across his body and took hold of his friend's far shoulder. His lower body followed his upper body as it turned to face Tom. He felt the heat of a rock hard, but smooth thigh against his stiffness.

He rose on tiptoe, pulling himself higher with his meager strength. Tom's face leaned down ever closer, their eyes locked. They were in synch, both leaning their heads slightly to the right. Tom hesitated before committing to closing the final distance, both in space and spirit. Their lips met sweetly, tenderly a brief first kiss. Jerry's heart instantly swelled with joy when Tom's lips pressed against his again with sudden vigor, confirming the rightness of the first.

"Jerry, why are you wearing pink socks?" asked Sidney in his usual flat tone.

The unexpected question startled Jerry out of his bliss and back into the real world. His first concern was Sidney's inquire came in too loud a voice for his sister to credibly pretend to be asleep.

"Shhh," Jerry said then turned and pointed at Diane.

Even as he pointed he saw she was obviously awake and had been for some time. A second pillow propping up her head made it clear she was watching. The placement of one hand between her parted thighs revealed what Diane thought of the scene. The motion of the fingers inside her lacy black panties were unmistakable.

"You were awake the whole time, Di?" he asked.

He felt a big paw ruffle his hair gently. "As if you didn't know, little buddy," said the amused Tom.

Ashamed now for trying to trick his friend and confused by the way Tom went along with it, Jerry's cheeks flushed once again. It was almost like lying.

"I'm sorry Tom," he said hanging his head. He sank down off of his toes and tried to slip out of the athlete's grasp.

Jerry felt himself squeezed against the man again. "Hey, you didn't hear me complaining did you?" said Tom giving him an affectionate shake.

"The coach says I can smell out any play and shut it down," the normally modest athlete bragged. "But why would I want to shut this one down?" he added flashing his trademark grin.

"I wouldn't have missed it for the world," said Diane from the bed. "It was so romantic," she sighed.

"Evidently it was also quite a turn on," Tom said, watching the young woman play with herself.

Uncomfortable watching his sister, Jerry looked away. His attention went back to his friend's huge throbbing cock. Tom was still sliding his hand up and down its length. Its engorged head was almost purple with arousal.

The redhead was fascinated that an inch of flesh beneath the flared ridge remained visible when the hand reached its highest on the upstroke. On the down-stroke a full five inches of the shaft was visible in addition to the swollen head. And Tom's hand was enormous.

"It's lovely Tom," he said, looking up at his friend's face.

"Thanks, little buddy," Tom replied giving the redhead a gentle squeeze.

Jerry felt the arm which had squeezed him momentarily release its hold. He next felt its big hand on his shoulder and didn't resist its subtle pressure to push him to his knees. It was Jerry's inclination to do so anyway, but it was thrilling to be urged.

"Jerry, why are wearing pink socks?" Sidney repeated.

Though reluctant to do so, Jerry tore his eyes from Tom's beautiful cock to look at the nerd. Sidney stood just inside the bedroom door taking a sip of soda. The nerd's attention seemed to be fixated on the socks. With the nerd's friend naked and about to suck the cock of a naked high-school jock, all he seemed able to see were the silly socks. Not to mention he was ignoring the near-naked goddess he'd been so determined to see. That was Sidney in a nutshell.

"Lick my balls little buddy," came Tom's deep voice from far above.

Jerry's eyes went back to the gorgeous cock and tightly packed hairless balls below. The shaved bundle was at a convenient height for him, unlike the higher jutting cock. First he leaned in to sniff the package. It smelled mostly of soap, a little of sweat, but also of cock Putting out his tongue, it encountered warm flesh.

"Oh yeah, nice!" Jerry heard the deep voice say as he gave it a flick of the wet tip.

He felt a big hand on the back of head encourage it forward. Giving into it and his own desire, he slathered one of the shaved balls with the whole width of his tongue. He was able to feel the soft crinkles of the surface and the hint of the hard nugget within.

He reached up and grasped a firm cheek of his friend's naked ass with each hand. The size of this man was amazing. Even the hips, which were the most narrow section of the man, seemed huge. The athlete was like a human mountain.