Jack & Jill - Chapter 01

Jack & Jill Went Downhill
Copyrighted 2014 © Rob Loveboy
Edited by Jack FitzHugh

Chapter 1

My name is Jack. Jack Sprat! Go ahead, recite the nursery rhyme and knock your socks off! I’m used to it. Well, know the truth I never did get used to it. My mother, in one of her drug induced states and a warped sense of humor, perhaps thought it was cute at the time, but I now reflect that it was probably in retaliation for my capturing the attention of one little spermie in a school of thousands that happened to be leisurely swimming by one night! A mistake that I would live to regret. A lifelong curse!

My full name is Jack Gaylord Sprat, so as you can appreciate, my secondary given name was no option in assuming another, less provocative title to rid myself of ridicule and harassment!

My Grandma raised me since the age of six. My mom had other, more important priorities to nurture and feed other than me, a serious chemical addiction that inevitably took her life! My father? Who knows where or who he is, but I’d guess that either he was just a quick fuck for cash or just another crack dealer taking it out in trade, but I must have inherited his good looks, dirty blond hair and sky blue eyes, trait’s that hadn’t revealed themselves in the family gene pool. Unfortunately, life being cruel and unfair as it is, I couldn’t have my cake and eat it too, I had my mother’s short stature to contend with and was about a head shorter than other boy’s my age!

Grandma was quite elderly and frail. Her indiscretion at a late stage of her life resulted in the birth of my mother. Perhaps that had some sort of negative medical effect on mom’s mental well being! However, I loved Grandma dearly and she tried her best to raise a young boy that had suddenly been dropped on her maternal doorstep.

I wasn’t really a problem child, just an incredibly independent boy who possessed an insatiable sense of adventure and bored easily! I would wake up some mornings and rather than go to school I would give in to the urge to go fishing instead. Or, while waiting for the morning school bus I would impulsively get on a city transit bus and explore the city’s alluring down town district.

I had Grandma wrapped around a finger and she would cover for my frequent truant behavior with excuse notes and the ever so increasing parent/ teacher summoned meetings. I could do no wrong in her eyes, it was her opinion that the education system failed to keep me interested and she laid the blame squarely on them!

I loathed structure in my life and school had way too much of that! It was not simply that I did not like school, I fucking hated it! Once, I tried joining the Boy Scouts, at Grandma’s urging, but quickly became bored with that as well. Their proclamation of “Boyhood Adventure” left a lot to be desired in my way of thinking!

I was intelligent though, passing my grades year after year. I was a quick learner and only had to be shown something once, so the curriculum became redundant and boring spending days on a single component. Maybe the other kid’s needed it repeatedly drilled into their heads, but I had better things to do with my time!

I met Jillian just shy of his fifteenth birthday. He had moved in across the street to live with his alcoholic father and step mother after he was shipped off by his mother. I was 13 1/2, had a few friends but none as close as Jillian and I soon became, inseparable to a fault.

I don’t recall what drew us together, he, sitting on his front porch, me on mine, but like a magnetic pull we literally met in the middle of the street. Once again, another nursery rhyme theme plagued my already tarnished self-image, “Jack and Jill!” He however exploited its friendship connotation and it became our epigram to anyone who knew us.

To say that Jillian shared my adventurous enthusiasm would be an understatement. He was down right dare devilish, conniving and manipulative by nature. Trouble hung over his head like a dark cloud. Even my Grandma who was oblivious to most of life’s realities warned me of the foreboding danger of our friendship the very first day she met him.

“That boy is the work of the devil … I feel it in my bones!” she warned me. “Do us both a favor and stay away from him!” I didn’t heed Grandma’s words.

Other boy’s in the neighborhood and school instantly feared Jillian. He was not overly big of frame, quite average actually, but he had a threatening tone of voice and a quick, violent temper flogging any boy who dared challenge him.

Or authoritative figure’s for that matter! The final irrevocable reason for expulsion from his last school. A male gym teacher made sexual advances toward him. Well, that’s what he claimed was the reason for plummeting the man but apparently nobody else bought into his version of events, after all, he was the one thrown out of the school! He never elaborated as to exactly what the sexual advances were, and yuck! — I didn’t want to know.

It wasn’t long before we were regularly sleeping over at each other’s house. Well, mostly my house as I had a nice room, styled in boyish decor and a double bed. What constituted his own bedroom was a storage room cluttered with old boxes and other paraphernalia to which his father and step mother so lovingly re-arranged enough space to adorn with a mattress tossed on the floor. A clear indication to his welcomed presence.

Even on school nights, with no parental consent ever being obtained, we slept together. School night was a very loose term anyway; dependent on if school was on our agenda for the following day!

It was our fourth or fifth consecutive sleep over that he announced he was horny and wanted to jerk off, suggesting that I join him! “All guys do it, its normal! So why try and hide the fact and deny ourselves the pleasure just because we happen to be spending the night in the same bed!” he reasoned. “After all, we’re buddies dude!”

I could not argue his logic and I was tired of doing it in the bathroom, so under the privacy of a blanket, underwear pulled over balls, we did the deed together along with a strange request that I tell him when I was ready to cum, “We can blow our load’s at the same time, together!” he suggested with a grin.

It always took me a long time to reach climax. I would play out the fantasy of ravaging Kimberly Allen, a girl at school who wouldn’t give me the time of day and seemed oblivious to my existence! Regardless, she remained my “Leading Lady” in the X-rated script of my lengthy jack-off sessions!

Jill didn’t seem to have as long a fuse as I did. After about 5 minutes, he was asking what the hold up was. The covers over his midsection would frequently cease to billow and the harsh squeaking tempo of bed springs lessened as he patiently held off orgasm.

About 30 minutes later, my testicles surrendered to self-abuse and released my coveted boyhood “piece de resistance.” Afterwards, mopping up with a crusty hand towel stiff with my own historical relevance, which oddly, he didn’t mention, his only comment was, “Dude … ya gotta find a hotter fantasy than that Kimberly Allen bitch!” he said with abhorrence.

What we did not seem to share was an interest in girls. At every mention of that gender, he would abruptly change the subject or go into a fit of rhetoric’s of how manipulative, egotistical and selfish they were.

I never entertained the thought that maybe he was gay. Just a late bloomer, not yet in the phase when a boy notices the female virtue! Nor did it occur to me then that his loathing hostility toward women had anything to do with the horrible stories he confided of when he was13 and spent 6 months in a Reform School run by abusive nuns! He claimed that they would apply punishment by caning the bare upper thighs and buttocks, often striking a testicle or two in the process! Or the ice cold showers endured for minor violations! He never expounded on the details of why he had been incarcerated.

I learned at the onset of our relationship not to delve to deep into querying Jill`s life. Most always, he was evasive and only later, when he felt the need or perhaps, comfort and trust in me, would he divulge personal information.

On another occasion when he had the urge to reflect, he was 8 year’s old his own drunkard mother, for no apparent reason, other than morbid entertainment, and the amusement of mixed adult company, had pulled down his pajama bottoms and singed the end of his penis with a cigarette. Some derogatory reference to his birth father’s manhood and legacy symbolic to “burning in hell,” he remembered hearing. I later saw the little scar to prove it.

I had no reason to disbelieve him when he occasionally became melancholy, sometimes teary eyed. It made me feel all the more loving of him in a close friend sort of way. Life hadn’t been easy for him, quite the opposite.

The following night he wanted to watch a Stanley Cup Hockey final playoff game on my bedroom TV After a futile effort of trying to capture the signal with bunny ears, aluminum foil, standing on one foot with an arm in the air holding a wire! Any possible tactic to appease him, snow still obscured the picture. Grandma didn’t

believe that cable TV was a necessity. Her afternoon soaps came in just fine on the living room RCA Victor that Noah, stoned at the time, must have stumbled upon, and thinking that her VCR system was its mate, took then aboard the Arc!

Anyways, Jill, thoroughly pissed off, contemplated the dilemma of the day. His tongue would protrude ever so slightly, like pouting when he was deep in thought, staring at nothing in particular. An idiosyncrasy trait that I picked up on after a while when he was up to no good!

He returned after about 15 minutes from his own home armed with a roll of electrical tape, a pair of pliers, wire cutters, flashlight and a small reel of cable wire, it’s origin I didn’t know. He next procured my neighbor, Mr. Figsby

‘s aluminum, extension ladder that was mounted on hooks to his backyard fence.

We lived in a very old, blue collar neighborhood. Brown weather treated telephone poles were haphazardly planted appearing like a burnt out forest. >From an aerial perspective I was sure that the electrical, phone and cable wires along with backyard clothes lines, all strung in every which direction, would appear like a giant spider web.

Under the cover of night fall, tools in his pockets and one end of the cable wire secured to a belt loop, he ascended the ladder.

I was instructed to unravel the reel of cable fifty or so feet to my bedroom window and attach the wire to the TV receptacle. After about 45 minutes and numerous near misses of clear picture, then snow, and hollers of communication in the darkness between my window and somewhere atop the top the pole, my colored Panasonic TV as old as I was, came to a brilliant, crystal clear rebirth to the likes never seen before!

He had pirated the cable company

‘s signal by splicing into a live feed. I just hoped that the rest of the neighborhood still had their cable! I watched a cable guy up a pole once,”he explained with pride of his handiwork, “only took him five minutes, so I knew it couldn’t be that difficult to figure out!”

I was elated to finally have cable TV — in my own bedroom to boot, nonetheless! We watched the Toronto Maple Leafs do battle with the Chicago Black Hawks in living color. That

‘s my Jillian for ya, clever and industrious when he had to be.

The cable wire hung low , strung from the telephone pole to Grandma’s clothe line post mounted on the rear porch, then looped into my bedroom window. Something he said he would figure out later before the old lady unsuspectingly got caught up in and strangled herself as she stepped out of the back door.

That night, we jerked off again. Suddenly, he kicked down the blankets exposing both our nude bodies illuminated by the glow of the TV. Intimidated with the fact that no one had ever seen me naked, let alone with a hard on, I was perplexed, mortified as I tried to retrieve some modesty by hauling up my underwear!

So strong were my inhibitions that I got Grandma to write a note excusing me from taking the mandatory, communal shower after gym class. Actually, I wrote it myself explaining that I had some sort of contagious rash that would flare up when exposed to hot water. She signed it under the guise that it was a permission slip for a field trip, presented to her when she didn’t have her reading glasses handy. It worked and I didn’t have to get naked in front of anyone!

My reaction didn’t escape Jill’s attention, telling me that I shouldn’t be ashamed or embarrassed about my body. He went on to profess that best friends should never hide anything from each other and in his personal opinion, clothing was a way of hiding something. Erections, jerking off and ejaculation in front of each other were paramount in demonstrating complete trust and friendship, “No secrets; no lies: no shame,” he proclaimed to be the catalyst element to a continued relationship among guys.

That being said, he turned on the bedside lamp, stripped off his underwear and tossed them across the room for effect, then stretched out displaying himself to me with a huge smile to match his huge cock.

With a great deal of hesitance but the rationalization that he had already seen me in my glory, I followed his lead., not wanting to portray myself as a chicken shit prude. His persuasive philosophies or ideals would always prevail over my naivety, values and self perception hence forward.

His cock was about an inch or so longer than my own, cut 5 1/2 inches and much thicker. His excess skin would fold up over his palm like an accordion and gather at his fat, circumcised mushroom head as he slowly manipulated himself.

Where my own scrotum seemed to shrivel up tight into my groin during erection, his hung low and heavy. I was fascinated with his genitals for some unexplainable reason! I wasn’t gay to my knowledge, oh what a thought! However, I had to admit to myself that seeing his junk and watching him do himself added to my own masturbatory excitement!

Once again, he asked that I tell him when I was ready to cum, which astonishingly enough I declared in less than ten minutes! He ejaculated as if on queue, with six long, copious gobs of cum. The first one landed on his neck, the balance easing in intensity, trailed down his chest and belly, and finally dribbled into his pubic hair.

I followed with a mere four shots. The first splattered my right nipple, trickling down the side of it, my belly button captured the rest other than the usual aftermath that looses its projectile, gathers on my thumb and eventually gives into gravity.

“Fucking awesome dude!” he said with an overly excited tone. I wasn’t sure if he was referring to my ejaculate or our weird, joint erotic endeavour, maybe both but I concurred in a gratified, quiet voice, as I mopped myself with the crusty towel and passed it to him! The pungent, musky odour of our semen hung in the air.

“Ya must have changed your fantasy!” he said slyly, bringing me to the shocking realization that I hadn’t even fantasize about Kimberly Allen! The live visual erotica and sexual stimulation of what we had engaged in substituted any previous fantasy of her! I had just jerked off, complete with orgasm, in record time at the sight of another guy’s naked body while watching him do the nasty! That thought kind of scared me.

Our itinerary the next day took precedent over school! I had previously introduced him to my passion for fishing and he quickly became quite the enthusiast. He wanted his own rod, and gear rather than taking turns with mine, so off to a major hardware chain store we went on a mission to outfit him.

As we made our way into the sporting goods department, he asked what the best rod and reel would be and I showed him the famous Mitchell brand. I jokingly caressed the assembled unit in a loving, exaggerated manner then planted a loving kiss to the reel, telling him that one day I would afford my own.

Jill always had money at hand and I never questioned its source when he would unselfishly treat me, buying fast food, movie theatre admission, arcade coin and such, but when he told me to grab two of the Mitchell units, one for each of us, I was flabbergasted and wondered how he could afford it! I didn’t even question his financial resources when he picked out a plastic tackle box and told me to fill it with whatever accessories, hooks, sinkers, lures and such that I thought would need.

He held the tackle box and I carried the rods as I followed him curiously to the rear of the store and into the cookware department. His sudden interest in pots and pans baffled me but I held any inquiry, engrossed in my soon to be new equipment and the anticipation of using it that day.

His gaze seemed to linger on two large swinging doors about 10 feet away on the rear wall. He motioned for me to follow and suddenly he pushed through the doors and we entered what was obviously the warehouse. I was dumbfounded as to why he would want to explore that area, the door sign clearly, in bold lettering read, “STAFF ONLY DO NOT ENTER!”

Our pace increased forward and unchallenged as we came upon a rear exit. Before I knew it we were outside and running in a back alley! The realization of what had just transpired struck me and I began to tremble uncontrollably in fear as I kept foot pace with Jill for what felt like forever. He finally slowed, looking over his shoulder constantly as he laughed! “Warehouse staff’s lunch hour! The best time to escape out the rear of a store!” I was enlightened. I had just unwittingly been introduced to my first of many to follow shoplifting excursions!

Once I knew we were out of danger I found the experience exhilarating, totally daring and revelled in excitement as we spent the rest of the day leisurely fishing and testing out my newly procured equipment!

That night we replayed our exhibitionist style of getting off when suddenly he reached over, took my cock from my hand, and began to slowly stroke. His hand felt great wrapped around my shaft and after a brief quandary of emotional turmoil, I reciprocated in kind. His cock felt wonderfully warm, soft and squishy, like Play-Dough!

We fondled each for a time. He unnervingly explored my tightly held balls giving me the courage to curiously toy with his satiny, Jell-O like sack of acorn-sized testicles. Both of us noticeably increasing our excited state with heavy breathing and the odd gasp of pleasure. In animalistic frenzy, we pumped each other, both our asses lifted off the bed and crashed back down, the bed springs clamorous objection was only vaguely noticed.

I came with unprecedented orgasmic ecstasy only seconds after him. No verbal confirmation was necessary, each intuitive to the other’s state of sexual bliss!

An overwhelming sense of shame and guilt suddenly came over me in the aftermath of our abnormal sexual behaviour. I just gave another guy a hand job! I could have and should have politely warded off his advances! It was an act of homosexuality, however minor in the general significance, I deduced in my mind trying to make some sort of sense and to mentally down play the implications.

As if reading my mind he blurted out with nonchalance, “just two buddies helping each other out, dude! No big deal, right? Like, why shouldn’t buddies make each other feel nice? It’s like scratching an unreachable itch for one another!”

Jill’s words lifted my spirits somewhat. and put things into a more acceptable perspective. A much needed, but perhaps lame excuse to appease my confused state of right and wrong! As far as the “itch” metaphor went, well … I could easily have scratched my own itch, but in all honesty, not quite as good as he did!

The next morning he tried to initiate an encore performance. I awoke with a start to find him in a toe to head position pumping my pee hard cock. His own erection uncomfortably close to my face as he masturbated himself.

Noticing that I was awake, he smiled deviously with obvious expectation that I would reciprocate. My shameful memories of the previous night’s encounter flooded my senses. The provocative position we were in only added to my self-reproach, a brief thought that perhaps oral sex was on his mind and imminent. Startled, I pulled away and sat at the edge of the bed telling him that I didn’t want to do that shit anymore. “Let’s just forget about what we did, okay? We just got carried away for whatever reason!”

“His face was contorted in venomous contempt. His fingers knotted into fists. I had seen that unpleasant demeanour plenty of times before and it certainly appeared that I was in for a taste of it. “Are you trying to tell me that you didn’t like what we did last night? Sure as fuck seemed like ya enjoyed it to me, fuck head!” he yelled angrily, “Fucking pussy loving moron!”

In fear, I was just about to submit to his desire that I hoped was only another hand job when as quick as his rage surfaced, it dissipated as he gathered self-control and searched out his clothes. I felt bad, guilty that I let him down when he made one final scathing retort under his breath and barely audible. “Fucking cock teasing bitch!” It’s meaning clearly significant, equating that I was no better than his loathing, low opinion of women!

To be continued …

Copyrighted 2014 © Rob Loveboy