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 at the bar

My body was practically trembling as I stepped off of my bike and approached the back door of the gay bar. I had a stir in my bottom that was growing stronger by the second, born of the desire I had to be topped right away. As my need grew more and more urgent, I used my boy sized knuckles to wrap against the sturdy metal door of the building I'd come to. The yearning in my body was so great that it was causing me a degree of angst, a craving for non stop anal sex that I knew I could only have by riding my bike to the alley behind the gay bar.

When the door opened, I smiled up at the owner, a 6 foot 3 inch stud with a brunette mane and a set of abs that seem to ripple through his tight shirt. Returning my smile, Michael stepped to the side and said, “You look very sexy today, buddy.”

“I think you look sexy too, Michael,” I said with a shy smile, then I looked up at my stud with pleading eyes while he caressed my right cheek.

“We're going to get you all fixed up, buddy,” he assured me, and I let loose with a sigh of relief that accentuated his smile. He reached out for my handlebars and I immediately acquiesced, stepping off of my bike and letting him roll it into his back office while I walked ahead of him, letting my scantily clad rear end swing from side to side the entire way.

To say that I'm familiar with Mike's office would be an understatement. For the last month, I've been visiting him there at least once a day; sometimes more than that. Aside from his tight body and beautiful face, he has a bonafide python swinging between his legs that I just can't do without. His office is furnished with a couch that's perfect for sex. We typically make out for a few minutes before the main event, and I love how comfy the cushions feel against my bare butt while our tongues dance.

Of course, they also feel nice when I'm on my knees, hanging onto the backrest with my rear end presented to my stud for fucking. And they feel good when I'm on all fours, resting the side of my head on the arm rest while Michael takes me doggy style. And of course, they provide a comfortable place for my back when I have my knees pulled to my chest, watching with a horny smile while my stud gives it to me missionary style.

So when I woke up this morning with a hard little boner and an ache in my boy pussy for his cock, I had to text him right away. A half hour later, over the protests of my mom, I was sliding my lucky shorts up over my horny bottom and tying my shirt off at the midriff before hurrying out the door to see him. As soon as he showed me to his office, I started to untie my shoes while he leaned my bike against the wall.

Joining me by the couch, my stud took full control of the situation by taking a seat and using his hands to rub my exposed tummy and the small of my back. I felt his warm palms running up my torso, under my shirt and up to my chest. At the same time, he slid his other hand down to my rump, which was barely contained in my lucky shorts. I had shivers of desire running through my small frame as soon as I felt his touch, then he puckered up and I moved in for a kiss that I wanted more than anything.

His tongue slid into my mouth and I let loose with a soft moan while he continued to palm my rear end through my shorts. I reciprocated by letting my tongue slide along his, then he took control of our kiss by sliding his other hand down to my rump so that he had two handfuls. My head was spinning with lust when I felt him pinching my bottom, getting me hot for the main event. He gave my buns plenty of attention, pinching and squeezing them over and over while we kissed deeply. I was yearning for him to take me when suddenly, his fingertips slid through the leg openings of my shorts and into my crevice.

I moaned like a bitch in heat when I felt three fingertips pressing against my moist boy button. I could actually feel the contrast between the heat of my pucker and the lukewarm temperature of his fingertips, giving me a naughty thrill as I contemplated the sex I was about to have. I felt the fly of my shorts being unfastened, and they fell loose and opened wide. He removed his digits from my crack and slid his hands out of the leg openings, letting them fall to the floor. As soon as they hit the tops of my feet, I stepped out of them and felt his hands prying my buttcheeks apart. He used two fingers to rub down my horny entrance, then he broke our kiss and smiled at me.

“You're hot and bothered this morning, aren't you buddy?” he asked, and I nodded through a hot moan. “I might need some help taming your boy pussy today.”

“Some help?” I asked, my desire transparent and my voice huskier than before.

“Would you like that?” he asked, and I bit my lower lip as I nodded. “I've got a couple of patrons at the bar that might like to come back here and service your bottom for you.”

With that, he took me by the hips and steered them so that I was facing away from him. I felt his hands parting my buns again, so I spread my feet to give him easy access. Seconds later, he buried his face between my cheeks and treated me to a deep rim job that had me moaning in ecstasy. My small, hairless dick was standing straight up like a statue and my toes were curling hard as he feasted deep at my back door. Finally, he pulled his mug out of my bottom and guided me to the couch cushion beside him, where I climbed on and held onto the backrest while he unbuttoned his jeans and unleashed his one eyed monster.

Looking over my shoulder, I felt my little wiener twitch when Michael's jumbo sized erection sprang loose. It was already moist and ready, and I was eager to have it inside of me anyway I could get it. Happily for me, my stud knew what I needed and acted to sate my urgent desires. With a warm smile, he stepped onto the couch cushion and placed the head of his prick at my lips. Giving my lips a playful tap with the meaty treat, I moaned as I slipped my mouth over it and started to suck it with a lusty smile.

In no time flat, I had all nine inches devoured, running my distended lips all the way to the base over and over again while my body sizzled with pleasure. I was using the flat surface of my tongue to bathe the underside of his trophy while I indulged in his full length and thickness as it slid through my lips and into my throat. Between my legs, my hairless little boner was on fire and between my buttcheeks, my moist boypussy was trembling with need.

Finally, after blowing my stud for three luscious minutes, Michael pulled his cock from my mouth while I whined in protest. When the head was about to be taken from my lips, I took care to use my tongue to bathe his well defined glans and suck as much precum as I could from the tip. As he took the crown out of my mouth, I treated myself to a final slurp, then I kissed the underside with gratitude.

Seeing that my mouth was still watering, Michael planted a deep, tongue filled kiss on me that he held in tact as he moved to my backside. I tilted my head back as his tongue stirred against mine, running it around like a large mixing spoon. I was longing to taste his delicious kiss for as long as I could, especially when I felt the dripping tip of his rod sliding between my warm buns, where it found my eager hole. As soon as it made contact with my pucker, my hole bloomed wide and he entered me with one delicious push.

I moaned femininely into his mouth as his length slid all the way up my butt, then his pubic mane smashed into my crack and I knew I had all of him. He broke our kiss and we shared a smile, then he playfully mussed my hair and started to thrust. Right away, I started panting with pleasure as his massive fuck stick ran along the walls of my boy pussy with authority. I used my fingertips to squeeze the couch cushion as the sensation of anal pleasure overwhelmed my body. I could feel the energy of our union running up and down the backs of my legs, all the way to my curling toes. My tummy was pulling up into my rib cage and my chest was heaving over and over again as I found ecstasy with my lover.

Out of nowhere, it dawned on me that I was in the grip of a prolonged anal orgasm that had taken hold right at the onset of our lovemaking and hadn't relented. My rectal muscles were clamping down with spastic waves, tightening around his cock as it bullied its way along my love tunnel. At the same time, my boy boner was throbbing and pulsating continuously while my head swam with decadent pleasure.

I was still in an orgasmic fog when I felt a soft kiss on my right cheek, then Michael asked me, “Where do you want my load, sugar?”

Acting on sheer desire, I moaned like a little girl and called out, “I want to swallow it.”

“Of course you do, honey,” he said with a gentle tone, then he fed me deep strokes for five more minutes. When he finally pulled out of me, he stood at the front of the couch while I turned and sat on my satisfied bottom, then I leaned forward and wrapped my lips back around his trophy and ran them all the way down to the base. In a matter of seconds, I found myself lost in the pleasures of deep throating his rod while my angry little boner stayed pressed to my hairless pubic bone. In the midst of my ecstasy, I felt his mighty sword start to swell even larger, then it began to twitch and flex in my mouth while I moaned with horny delight. His nut sack pulled tight to his body, and with an authoritative throb, his load spewed forth and filled my slutty mouth.

“Mmm!” I moaned as his cum load erupted like hot lava for me to swallow with a naughty smile. My eyes were lit up like a Christmas tree as I accepted volley after thick, delicious volley of his spunk. I was gulping furiously as each shot filled my mouth, filling me with the goodness of his seed while I grinned up at him with gratitude.

“Is that good, buddy?” he asked, and I nodded eagerly. When his entire load was received, I spent a luscious afterglow licking thick strands of cum from his shaft and balls. Finally, he pulled his dick from my mouth and took a seat on the couch. I snuggled up to his chest and sighed with contentment while he rubbed my back and groped my satisfied bottom, then he treated me to one more deep kiss.

“Thanks Michael,” I said with a shy smile, eager to show my stud how grateful I was for the rear end service he treated me to, and the bonus mouthful of cock and cum that I was lucky enough to receive.

“You needed that, didn't you honey?” he said with a tender inflection in his voice, and I nodded with a smile. Caressing my right cheek with his fingertips, he added, “I've got something else for you, if you want it.”

Without even having to ask what it was, I scrambled to get between his legs and wrap my lips around the head of his still engorged member, anxious for my bonus. I smiled hopefully up at him as he watched me get into position, then he relaxed and his warm pee started to flow into my mouth.

“Mmm!,” I moaned again, drinking his yellow love potion with a greedy smile on my face. Happily for me, Michael really had to go and I was treated to a large helping that coursed into my mouth at a high rate of flow.

As his stream started to wane, he let loose with a loud and prolonged fart, signaling the end of his bladderful. I was sad that it was all gone, but grateful that he thought to share it with me. As the aroma of his fart drifted into my nostrils, I grinned up at him and took a deep whiff, loving the naughtiness of my disposition.

“Such a happy little bottom boy,” he gushed as he watching me grinning up at him with his dick still trapped between my lips, making a little pig out of myself. I nodded eagerly in agreement with his assessment, then I used my tongue to bathe the glans around the head of his prick.

Instead of letting me continue, he urged me to rejoin him on the couch by patting his left thigh. I obediently let his cock slip from between my lips and placed a final, grateful kiss right on the end, then I climbed into his lap and let him hold me.

“Are you all set now, or should I send in the reinforcements?” he asked, running his fingertips through my head of brown hair.

Feeling a tremble of desire run through me, I looked up at him and said, “You can send in the reinforcements if you want to.”

“Oh yeah?” he said, raising an eye brow as he slid his middle finger into my crack and gave my still winking hole a rubdown. I nodded up at him while I bit my lower lip, earning me an incredulous smile and a kiss on the lips, then he got up and got dressed while I pulled my knees to my chest and played in my tingling boypussy.

Almost as soon as Michael walked out, a total stranger walked in. I was still toying with my horny hole when we locked eyes, then he diverted his gaze down to my hole, which I had stuffed with three fingers. With a slutty smile, I licked my lips and studied his crotch, which was bulging with an erection. Wanting him to know that I was hot for a fuck, I moaned softly and eased my fingers out of my bottom so he could see what I was offering him.

Without a word, he unbuttoned his pants and unleashed his boner,which looked to be about seven inches in length. He climbed between my thighs and I moaned again, then he placed the head of his prick up to my dilated entrance and pushed in. As soon as his full length was resting inside of me, my boy pussy closed tight around his shaft and I smiled up at him. Wrapping my arms around his neck, I puckered up and he leaned down to kiss me as he started to thrust. With a mouthful of stiff tongue and an ass filled with hard cock, I felt my body roaring with passion while my feet rocked back and forth in the air.

When he seeded my boy cunt we broke our kiss and he pulled out. He gently offered me his cock to suck, and while I was moaning around the delicious treat, I felt another set of hands lifting my legs into the air. Not concerned with even checking to see who was about to enter me, I simply cooperated by pulling my knees back to my chest while I batted my eyes up at the stranger whose cock I was moaning around. I felt the delicious sizzle of anal penetration, then my boy pussy throbbed hard and I realized that I was accepting a long, thick dick.

When the cock I was sucking was taken out of my mouth, I turned my attention to my new top and climaxed immediately. He was a genuine stud, with bulging muscles and a thick mustache. Between my legs, his massive prick was dominating my boy pussy, whipping it into shape and showing me who was in control. Just like my previous top, it was a man I'd never seen before, but he seemed to know exactly what to do to keep me moaning. Two minutes later, he bred my hole with his potent spunk and I climaxed again.

As his mancock was unloading inside of me, he leaned in and planted a wet, tongue filled kiss on my mouth. This only added to my orgasmic pleasure, prolonging my climax while I moaned like the little sissy that I am. When his entire load was planted in my boy butt, he rested inside of me, his massive pleasure stick throbbing against the walls of my dominated boy cunt. Before I could think about what was next, he began feeding me strokes all over again and my body reacted in kind.

Breaking our kiss, he told me, “You're a little cutie, kid. Mike said you were down to fuck, and he wasn't lying, was he?”

Through a long, depraved moan I shook my head no, biting my lower lip as he worked my hole out with his stud prick. In the midst of our second fuck, he tenderly asked me, “Would you like to have another dick to suck, honey?”

Feeling my heart burst with joy, I eagerly nodded my answer with an affectionate smile, prompting my top to lean in and plant a sweet kiss on my dripping lips. Then, with the courtesy of a stud who knows what his pussyboy needs, he called out for someone named Jason to come back and get his dick sucked. I didn't recognize the name, but seconds later, we were rejoined by the first stranger I'd put out for. In a flash, I found myself moaning around his thick seven inches while the men French kissed above me.

Ten minutes later, with my boy pussy conquered, the men traded places and I found myself eagerly blowing my well endowed top. My head was spinning with pleasure when his long, thick shaft jerked with authority in my mouth just as his load spewed forth. As I was swallowing his man spunk, Jason pulled out of me and jerked off over my splayed buttcheeks. I watched with a naughty smile as two hot ropes of cum painted my boy butt, then I sucked his prick clean while I basked in the afterglow of a thorough rear end service.

With Jason's hard, horny mancock still trapped between my lips and a naughty look in my eyes, I reached up and pressed against his pubic bone with the flat of my hand. As soon as he felt me adding pressure to his bladder, he knew what I wanted and shut his eyes. A split second later, I was gulping furiously as he unloaded his bladder for me. His flow was strong, and as the seconds passed, I realized that I might not be able to keep up. Happily, he redirected his stream into my hair while I caught up, then treated me to one last large mouthful that foamed up as it coursed in. When he was finished, he shook off over my opened mouth and smiled down at me, then he stepped to the side and my still anonymous stud presented his prick to me.

It was nothing but a privilege for me to receive another load of warm, comforting pee, and he was generous with his offering. I loved how I could hear his pee audibly filling my mouth while I tried in vain to keep up and not lose any. Just like Jason, my anonymous stud simply redirected his stream when my mouth was too full, aiming it at my clothes on the floor while I watched with a slutty smile. When I gulped my mouthful down, he graciously gave me the rest, then he ended his flow with three strong shots that hit me in the face and hair before he shook off over my opened mouth.

By now too far gone to stop myself, I scrambled to the floor and treated myself to a delicious taste of each of their rear ends. As soon as I crammed my face into Jason's warm crack it became obvious that he hadn't showered that morning. As soon as the sharp smell of his butthole filled my nostrils, I found myself moaning wildly while I sniffed and licked deeply, so grateful for the pleasing flavor and aroma.

When I finished dining at Jason's back door, I made a fast play for my anonymous lover's backside, and the payoff was huge. His crevice was sweaty and swampy, and as I tongued it out, my head was spinning with the possibilities. The flavor was so dark and powerful, a perfect match to the smell, and I was loving it. Very reminiscent of the way my own poop chute smells after a day of cock riding, it had a rich aroma that I couldn't pull myself away from. With each pass of my tongue in and around his stink hole, my tongue was encapsulated with the dark, naughty flavor of dirty butthole, and I felt like I couldn't pull myself away.

Finally, it was Jason's hands roaming my bare butt that caught my attention, then his words sent a shudder through me.

“Hey buddy, do you think you'd like one more ride?” he offered, and without pulling my face out of the rear end I was feasting on, I nodded my head. “Okay, then let's get you back on the couch.”

With that, I treated myself to one last series of deep licks of my lover's pooper, then I crawled back onto the couch and presented my rear end to Jason for fucking. He slipped into me with no effort at all, and while he was running his pleasure stick back and forth in my slutty hole, I was rubbing the loose, distended lips of my boypussy. In a moment of sheer ecstasy for me, my anonymous lover planted a deep, tongue filled kiss on my mouth just as my boygasm was taking shape, then my little body erupted with the flames of gay ecstasy.

While I was still in the grip of my anal rapture, Jason bred my hole and pulled out so my makeout partner could take his place. Soon, I was moaning like a whore as deep cock strokes prolonged my pleasure. Jason stepped onto the couch and offered me his cock to lick and suck clean, then he kissed me deep until my final rear end service concluded with another batch of cum being planted in my bubble butt.

With my tummy swimming with sperm loads and my cum filled bottom dripping with hot spunk, I stepped back into my damp lucky shorts and kissed all three of my studs goodbye. Making plans to see all of them again the next day, I rolled my bike out the back door and rode home, glowing with satisfaction the entire way.

Up Next: Simon at the Park

Other Work by Josh Terrence: