Simon's Lucky Shorts, a short story series by Josh Terrence

bb/mb/oral/anal/mast/ws/rimming/

Author's note: This story depicts sexual acts between males of various ages. If you are offended by sex between teenage boys, preteen boys or between males of any age, why are you here? If you are not a legal adult or if this content is illegal in your locale, leave now.

This story is a work of pure fiction. The taboo acts depicted in this story are not condoned by the author, this is fantasy only. All Characters in this story are portrayed by actors 18 years of age or older. This disclaimer applies to all installments of this story, past and present.

To read other stories involving the fictional protagonist in this series, check out the following stories:

A Package for Simon

Simon Spreads His Legs

Pacific Rim Job

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Simon Cruises the Neighborhood

“Fuck, your ass looks so hot in those shorts, Simon,” Larry hissed as I rolled my rear end around for him and moaned around his big boy dick. “I can't wait to fuck you.”

“Mmm!” I moaned again, sliding my lips all the way to the base of his prick and flexing the muscles in my throat while I pushed up with my hips to let him know that I was hot to have his cock in my ass. I felt his hands running all over my the denim that was riding deep in my crevice, then he started to grope my exposed buns and I felt my boy pussy sizzle with need.

At the moment, I was alone with Larry in his living room. His mom and dad both had to work early on Saturday morning, so the coast was clear for us to get down and dirty without any distractions. It was 8am when I rode to his house on my bike, letting my easy access 12 year old boy butt linger invitingly in the air the whole way. As soon as I rode into his yard, he opened the front door and beckoned me to hurry inside. I laid my handlebars against the wall in the front entrance of his living room, then I hastily unbuttoned his fly, anxious to suck dick for him.

As soon as I wrapped my lips around his trophy, my tummy started to glow with contentment while my itchy boypussy called out for penetration. Still, I was grateful for the mouthful of cock that I had at the moment, and wanted to take the time to savor the generous treat. It didn't take very long for me to work all seven inches into my mouth and down my throat while his constant flow of precum gave me a salty bonus. As I settled into the blowjob that I woke up longing to give, he palmed my horny rear end and I moaned eagerly.

“Do you want to finish sucking my dick?” he asked, and I hastily nodded my answer as I continued to deep throat his pleasure stick. Seeing that I was as horny as I usually am, he playfully asked, “How many times do you want to be buttfucked today?”

Instead of holding up my fingers or pulling off of his delicious sword so I could answer, I began gyrating my hips in a continuous, sensual grinding motion that lasted for the duration of the blowjob that I was lustily performing. Seeing that he'd struck a nerve with me, he assured me, “With your ass stuffed in those shorts, you're going to get all the cock you want, Simon.”

Hearing his promise filled me with even more desire, and I cast my bedroom eyes up at his face while my bottom continued to roll around in the air behind me. Five minutes later, Larry groaned and his load spewed forth, filling my watering mouth with its warm, thick and wholesome goodness. I sat up on my knees and swallowed with a decadent smile, then I licked my lips and resumed my lust filled sucking until his crotch and scrotum were free of any cum strands.

My eyes were fluttering with gay romance when he helped me to my feet and we shared a deep, tongue filled kiss that swept me away. While our tongues were dancing, Larry unbuttoned my shorts and they fell to the floor, then I stepped out of them and he eased me onto my back. I wrapped my short, skinny arms around his neck while my legs were lifted onto his shoulders, then his hard as steel prick slid into my boy pussy and bottomed out. With our makeout session still in tact, my 16 year old stud treated me to a deep, heavenly lay on the living room floor.

His talented dick felt like it was dancing in my hungry rear end as he fed me stroke after decadent stroke. My mind was caught up in the duel rapture of our delicious kiss and the sinful pleasure of his deep thrusts, swimming with carnal ecstasy while my boy boner raged at its full three inches. With an inward plunge that I accepted, I found myself swallowing another intoxicating mouthful of his warm saliva while my body was dominated. Before I knew it, five minutes had passed and I was still in the full service lane of anal delights. Then five minutes turned to eight minutes, then it was 15 minutes and my body was in the grip of a full scale inferno. Finally, twenty minutes had passed and Larry doused my fire with a potent load of his rich, thick sperm that coated the walls of my sizzling boy pussy and left me in a state of complete and total satiation for the time being.

After having my bottom seeded by my stud, I curled up at his side and sucked softly on his spent member. I loved being in his embrace while I worked to clean his equipment, then we shared a deep kiss and he fell asleep. Still horny after the five star performance that my stud treated me to, I planted a final kiss on his lips and promised to return, then I rode my bike to the other side of the neighborhood in search of more gay sex.

"Hey buddy, what are you up to?" Coach Johnson asked, and I shrugged my answer as I coasted on my pedals up to his garage. He looked around the street to see if anyone happened to notice my slutty attire, then he ushered me in and closed the garage door. I set my bike down and we went inside to the dining room, where Mr. Johnson took a seat at the table and motioned me to him.

"Did anyone see you riding down the street, Simon?" he asked as I approached him, looking directly down at his crotch with hungry eyes.

"No Coach," I promised him, my voice husky with desire. "I wanted to dress sexy for you today."

"You look very sexy today, honey" he assured me, then he wrapped his arms around my small frame and slid his hands into the seat of my lucky shorts. "What did you have in mind, sugar britches?"

Hearing him use so many tender pet names on me sent a strong shiver through my rear end, and I wanted to do something special to show how much I enjoyed it. So I let loose with a soft, feminine moan, then used a thick lisp to tell him,"I want to get laid this morning,"

"Of course you do, honey," he said with an affectionate smile. "I can tell by the way you're dressed that you're in the mood for some cock in that horny rear end of yours."

Looking into his eyes, I nodded my confession while he took two firm handfuls of my bubble butt and began kneading them. I moaned again and bit my lower lip, then I watched with needy eyes as he leaned in and planted his lips to mine. His strong tongue invaded my mouth and I let him take full control over our kiss by following his lead. His man sized tongue was in charge the entire time, stirring in my mouth like a massive spoon, taking my boy sized tongue along for the ride.

I felt his hands slide out of the seat of my shorts, then he unbuttoned them and they fell to the floor. Breaking our kiss, he grabbed me by the hips and steered my little body so that I was facing away from him. I felt his hands come to rest on my hips, then his thumbs hooked the insides of my crevice and my buns parted right at my anus. I felt his fingers rubbing it, then he slid his middle finger up my butt and I moaned.

“What's this, honey?” he asked softly, feigning surprise at the discovery of Larry's spermy deposit.

“I was with a special friend before I came over,” I lisped, looking over my shoulder for his reaction. He raised an eyebrow and eased his middle finger out of my boy pussy, then he held his sperm coated finger up to my nose. I took a naughty whiff, then I sucked his finger into my mouth with a slutty moan. While I was sucking lustily on his finger, he used his other hand to give my buns a firm squeeze while he talked to me.

“My my, sweetie, you're in a very naughty mood today, aren't you?” he noted, and I nodded in agreement with him. “Maybe Coach Johnson needs to bend you over a few times this morning. What do you think about that, sugar britches?”

“I'd like that,” I lisped again, then I licked my lips and gave him another suggestion. “I think you should make me spend a lot of time on my knees, too.”

“Oh yeah?” he asked, and I nodded eagerly. “Would a mouthful or two of Coach Johnson's dick get your horny bubble butt back under control?”

This time, I shook my head no with a mischievous smile, then I lisped, “I'll need a lot more mouthfuls than that. Plus I'll need you to bend me over more than just a few times.”

“It sounds like you're flirting with me, honey,” he said, and I nodded again. “Well then, why don't we start you off with a nice mouthful of cock and see what happens?”

“Okay!” I lisped gayly, then I scrambled to my knees and worked to unfasten Coach Johnson's fly. Seconds later, his massive erection sprang free and I leaned in to wrap my lips around it, letting loose with a deep sigh of contentment and a series of soft moans. In no time flat, I was taking deep plunges down his shaft, letting my thinly stretched lips traverse all 10 inches while my boy pussy roared with desire.

“Atta boy,” he praised me while I took my time and savored his all mighty cock.

I've spent so much time sucking Coach Johnson's dick since the start of the school year that I've grown attached to it. At its base, the monster is nearly six inches around, complimenting the 10 inches of length that never fails to make my mouth water. I've always been an eager cock sucker, but once I started sucking cock for Mr. Johnson, my work rate picked up significantly.

There's just something so pleasing about sucking his dick that I can barely describe. It's always spring loaded and ready to explode with cum, which just drives me crazy. I love how ten minutes between Coach Johnson's legs can turn even the worst days into the best day ever. His potent loads pack an extra punch that adds something special when I swallow them. It's as if they have the ability to take control of my libido and stay on my mind all day. They keep me in my rightful place as a pussy boy by reminding me that a real man blows loads that sissies like me long to swallow.

As a pussyboy, I spend all day and night craving Coach Johnson's spunk. I swear that with every load that I take from his cock, my boy wiener gets smaller. But I love the way his spunk makes me feel as its sliding into my tummy after a session between his legs, slobbering and moaning around his man cock. I get excited about the idea of deep throating his trophy all day long, then hurrying home and measuring my puny little boy rod to see how much length I've lost.

Of course, his loads have the same effect on me when they're pumped into my busy rear end. I bend over for him more than once a day at school, and after a rooting in his office, I find myself frantic for the next one. Each time he breeds me, I feel more feminine than I did before I took my pants down and presented my rear end to him for fucking. And just like when I swallow his loads, taking them up the ass seems to make my dick a little smaller each time.

While my mind was awash in the feminine emotions that Coach Johnson's dick induces, I felt his fingers running through my hair and he spoke tenderly to me again.

“You're doing such a great job, sweetie,” he complimented me, and my eyes fluttered with romance as I gazed up at him. “I bet you'd love to stay between my legs all day, wouldn't you?”

I nodded my confession, then I moaned like a little girl while he stroked my hair and continued to dote on me.

“Such a precious little cock hound,” he gushed, eliciting a hot moan from me. “I know you can't wait to swallow Coach Johnson's baby makers, can you honey?”

Still moaning, I shook my head no while I bobbed my head up and down with fluid motions and slurped loudly around his prick.

“I can tell that you're hot to have my cock in your tight rear end, too, sugar,” he noted, and I nodded eagerly. “I'm so glad you came by to get yourself laid.”

With that, I moaned femininely and rolled my ass around, just like I did when I was with Larry. At the same time, I began flexing my throat muscles around the big dick in my mouth, anxious for the load that was promised to me. Coach's hands came to rest on the back of my head and I felt a powerful tremble roll through my horny body that served as a catalyst for me to double down. I heard him starting to hiss loudly, then his hissing turned to cursing. Then his trophy started to throb with authority in my slutty mouth and I knew my reward was on its way.

Just like he always does, Coach Johnson thrusted his hips and his ass raised up from the dining room chair. I felt the swell in his shaft as it rolled all the way to the tip, then his cock shivered between my lips and his load heaved forth. I quickly formed a nice, tight seal right beneath his glans and his spunk flooded my mouth. Unable to deny myself the joy, I quickly started to swallow, taking gulp after delicious gulp of his seed, then his ass settled back into the chair and the hot spunk stopped pumping into my mouth. A thick strand was stuck to the side of his shaft when I pulled my mouth off, so I anxiously licked it up, then I settled into a gentle licking and sucking on his shaft and balls until he pulled me off.

I was still on my knees when Coach stood up from his seat. He offered me his hand, then he helped me stand and guided me to the chair. I quickly crawled onto the chair on my knees and held onto the backrest while I pointed my horny rear end in his direction. He grabbed my hips tight and lined his still rock hard scepter up to my entrance and slid it in with one luscious thrust. I was trembling with pleasure as the long, thick shaft invaded my horny hole with a loud, moist crackle that I could hear, then his pole got hot and I moaned again.

“It's okay, sugar britches,” he said in a sweet, caring tone while he rubbed the small of my back with one hand. “We're going to do something about that pesky itch you have in your bottom. Are you ready for Coach to get to work?”

“Yes,” I lisped thickly, this time unintentionally. It came out as more of a plea for him to start thrusting than an answer to his question, but when he tightened his grip on my hips and began to thrust, I found myself sighing with relief.

Right away, my horny poop chute started to clamp down around his cock with spastic contractions. Between my legs, my boner was on fire while my groin and abdomen were starting to sizzle. My moaning was frantic, and quite feminine, prompting Coach to speak softly to me again.

“Is that what you needed, honey?” he asked, and all I could do was look over my shoulder and nod through another set of moans. “Are you looking forward to a nice, long lay with Coach Johnson?”

My mouth was hanging wide open and my dark hair was starting to stand up on its own. I had goosebumps spreading out all over my body and a continuous wave of heat and pleasure were working in concert to bring the pussyboy out of me. But still, I found a way to gather my senses just enough to nod my frantic reply, then he used his hips to put added force behind every thrust and my vision started to blur.

“There you go, sweetie, have a nice strong one,” he encouraged me with a loving tone, and with that, my anal orgasm erupted. “That's right, buddy, let Coach take care of that itch the right way.”

Coach's voice sounded like it was miles away as I floated in the waters of anal ecstasy. Every deep thrust seemed to prolong my climax, and there was no end to the thrusts he was feeding me. Just like my last encounter, my top seemed to have the endurance to take me over the edge several times in a row. Mercifully, Coach pulled his unspent rod from my rear end and planted a kiss on my cheek, bringing me out of my spell.

“Come on, sweetie, let's get comfy in my bed,” he encouraged me, then he scooped me up in his arms, cradling me like a bride and carrying me to his room. When he set me down, he crawled between my legs and picked them up, then he slid his pleasure stick back up my poop chute and began his dance of delight all over again.

When I rode my bike off of Coach Johnson's street, my rear end was humming with delight and my craving to suck cock had been sated. The many loads that Coach had fucked into my bottom were practically bubbling around my pucker in an effort to escape. My face was glowing with so much contentment that I noticed the shine myself as I tied my shirt off at the midriff and slipped back into my lucky shorts.

There was no doubt that the hour I spent with Coach had turned me into a total pansy. By the time I kissed him goodbye, my lisp seemed like it would be there permanently and I had a feminine feeling that I didn't want to be without. When he opened his garage door, I got on my bike and deliberately let my sated rear end swish from side to side while I rode down the block. I turned the corner and sighed again, grateful for the skillful service at my back door.

When I turned onto my street, there was an older man dumping his lawn clippings into the trash bin. He gave me a long look as I pedaled towards him, so I smiled and waved at him. When he waved back, I noticed him checking out my shorts so I stopped in front of his yard.

“Well aren't you a sight?” he noted while I looked up at him with curious eyes. “You look like you're dressed to turn a few heads, kiddo. What's your name?”

“It's Simon,” I said, still lisping as the afterglow of my time with Coach Johnson lingered. “What's your name?”

“Don't you live a few doors down from me Simon?” he asked, and I nodded. “I thought I recognized you. You have quite the reputation around here, buddy. A lot of boys go in and out of your house when your mother's not there.”

“I have a lot of special friends,” I explained, then I looked down at his crotch and moaned at the sight of his growing bulge.

“It's too bad we haven't had the chance to get to know each other better, buddy,” he offered with a knowing smile. “You can call me Mr. Longwood.”

“Maybe we can get to know each other better right now,” I said with a thick lisp and a suggestive smile.

“I think I'd like that, Simon,” he told me, then he led me up his driveway and into his house.

Some men like to talk to a boy like me before they try to get into my pants. Other men like to get down to business. Luckily for me, Mr. Longwood is the kind of man who likes to get right to it, so less than two minutes after he closed the front door, I was out of my shorts and bent over with my rear end sticking straight up in the air. I had my palms pressed flat against the wall for leverage while he fed my boy pussy deep strokes of hard cock that felt so good.

Ninety seconds later, he pulled out of my cum sopped hole and shot his load all over my ass cheeks, then I dropped to my knees and gave his throbbing boner a quick suck. When it was all clean, he put it away and I hiked my lucky shorts, then we exchanged cell phone numbers and I was gone.

Up Next: Simon at the bar

Other Work by Josh Terrence: