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 Park

The sun was beaming into my bedroom when I opened my eyes, reminding me that it was a Saturday morning and there was no school. I'd been in the middle of a sweet dream about blowing Coach Johnson, and as I blinked to try to get the room to come into focus, I found myself remembering it with vivid detail; I'd gone to his office and dropped to my knees, settling between his legs as I sucked on his long, juicy prick. Between my legs, my own hard on was tingling as it continued to get smaller and smaller, and I was loving it.

But that was when my aching bladder lulled me out of my sweet slumber.

I got up and made a beeline for the bathroom so I could pee and wash my face. I found myself wishing that it were a school day just so I could have as many chances as possible to blow my sexy PE teacher. As thoughts of sucking his big dick filled my horny imagination, I felt a sudden, overwhelming desire to suck as many large cocks as I could, and right away. I hurried back to my room and slipped into my lucky shorts, then I put on a purple tee shirt and tied it off at the midriff. Snatching my tablet, I went downstairs, where my mom was making breakfast in the kitchen.

“Honey, I know you aren't going out like that,” she admonished me, but I only nodded at her to let her know that I was dressed in my outfit for the day. “I at least want you to change out of those shorts, Simon.”

“I don't want to,” I countered in a small voice, watching as she took a cup down from the cabinet so she could pour me some milk.

While she was busying herself with that, I logged into my social media page and started typing out a post to let people know that I was in the mood to suck big dicks, and that I wanted to suck them all morning. I was about to hit the “post” button when she said from over my shoulder, “Honey, don't you dare put that online!”

“But it's true,” I countered, then I posted it anyway while she set my cup of milk down and gave me a measured look.

“I don't know what I'm supposed to do with you, Simon,” was all she said, then she went back to making breakfast while I checked my phone for texts.

By the time I'd eaten my breakfast, I'd arranged to meet up with four well hung studs at the park, and I was hoping that I'd be able to entice even more. My mouth was watering at the prospect of sucking each and every one of them off, then swallowing their thick, tasty loads with a satisfied sigh. I was so horny to give head that I left the house a little early, hoping to come across a random lover or two on the way.

Of course, before I left the house, my mom tried to make me delete the post but I ignored her demands. Instead, I hopped on my bike and pedaled towards the park, letting my scantily clad bottom linger in the air as I rode down the block. As I approached Mr. Longwood's house, I saw him working in his garage and stopped to talk to him.

“Hi Mr. Longwood,” I said, coasting into his driveway and coming to a stop at the edge of his garage.

“Well, what do we have here?” he said, smiling like a Cheshire cat at my attire. I smiled back up at him and licked my lips, prompting him to say, “Why don't you come inside, kiddo?”

“Okay,” I quickly agreed, then I pushed my bike into his garage and set the kickstand while he hit the button to close the garage door behind me.

“Where are you off to today, buddy?” he asked with a knowing look on his face.

“I'm riding my bike to the park,” I revealed, and he nodded with a smile.

“Well, that makes plenty of sense, especially with that post you made this morning,” he remarked, and I felt a shiver run through me as he reached out and stroked my cheek with his thumb. “I'm sure you'll find plenty of company down there, kiddo.”

“I really hope so,” I admitted, then I looked up at him. “Did you like what I posted?”

“I thought it was a very sexy post, buddy,” he complimented me, then his thumb moved from my cheek to my lips, where he gently traced their perimeter. “You're still in the mood to suck dicks, I take it?”

I nodded slowly, then his thumb slid along the crease between my lips and I let them part so I could suck it into my mouth. Letting loose with a moan, I gave his digit a long, sensual suck while he used his other hand to run his fingers through my brown hair.

“Why don't you go ahead and treat yourself to what you're really after, Simon?” he said softly, and I let go of another moan, this one needy and filled with desire. Unable to resist, I reached out with my hands and unbuttoned his trousers, then I reached into his boxers and pulled out his beefy prick. I gave it a few strokes, then he pulled his thumb out of my mouth and I bent over far enough to wrap my lips around the head of his dick.

My head was spinning with lust as I quickly worked my lips all the way down to the base, then I treated myself to a pleasure filled sucking of his full length. The length and thickness of his shaft was accentuated by its succulence as it throbbed with authority in my mouth and throat. The glans that encased the head of his prick were thick and well defined, and I was in heaven as I ran my tongue and lips along their ridge, again and again.

I used my hands to fondle his big, low hanging balls, taking the time to appreciate the fact that I was handling 98.6 degrees of sheer manhood. I could practically feel the cum load that he had for me boiling in those man sized nuts. I was ready for that load, too, and hopefully, many more before the morning was over. As I sucked lustily on Mr. Longwood's juicy man cock, I found myself grateful that I decided to leave the house early in search of some bonus action.

I was bobbing my head up and down in a fairly rhythmic motion when I started to notice the signs that my reward was forthcoming. The first signal I got was when Mr. Longwood's warm ball sack tightened in my hands. Then his cock started to throb in my mouth, filling me with an urgent brand of need for his spunk. Then I felt his throbbing dick expand and its juicy qualities seemed to intensify, making my head spin even harder as I prepped myself for the grand finale.

Being an experienced cock sucker, I was able to detect the rising cum load as it made its way along Mr. Longwood's meaty shaft, and I found myself pulling my lips all the way up to the tip of his cock. I wrapped my lips around the base of his crown, forming a nice, tight seal just in time to receive the first of several hot shots of cum. I gulped furiously, anxious to keep up and not lose any, but when it became impossible, I took a different, more indulgent course instead. Because as Mr. Longwood was shooting his mighty load into my hungry, slutty mouth, I went back down on his prick. With my lips wrapped around the base, his strong cum shots hit the roof of my mouth and ricocheted back down so that they coated every single inch of his long, thick scepter.

Which was why I was able to spend a luscious, five minute afterglow licking and sucking his cock and balls clean. There was cum everywhere, from his cock and balls to the creases between his scrotum and thighs. I was even able to lick cum out of his taint, where a thick pool had formed. It was even matted in his pubic mane, and I took particular pleasure in licking it all out, one strand at a time.

When there was no more cum to lick up, I gratuitously moved to his backside and buried my face between his butt cheeks. With a naughty grin, I inhaled deep, loving the aroma of hot man butt, then I dug in and feasted. In the midst of my yummy feast, Mr. Longwood chuckled and said, “You know what you're after, don't you kiddo?”

“Uh huh,” was all I could muster as I worked to shove my face deeper in his crack. While I was still eating at his back door, I reached around and felt his cock for stiffness. Happily for me, he was fully erect, so I stayed where I was and feasted for a few more minutes, then I crawled out from between his legs and put my denim clad bottom in the air.

“Are you looking for some cock for your other end, baby boy?” he asked, and I moaned hotly while I nodded my answer. With a chuckle, he helped me to my feet and we moved from the garage to the living room. He waited for me to drop my shorts, then he let me slobber all over the end of his prick for a few more moments. While I was treating myself to another mouthful of hard dick, he was fingering my bottom, getting me hot and moist for the main event.

When I pulled off of his prick, I crawled onto the couch with my feet hanging off of the edge of the seat cushions. I felt him place the head of his prick up to my hole, and it quickly bloomed in anticipation of what I was after. As soon as it opened up for him, he slid his dick all the way up my ass and I moaned like a girl while I smiled over my shoulder at him.

“How's that, buddy?” he asked, and I sighed with contentment.

“It feels good,” I hissed, then he started to thrust and I felt my body erupt with the flames of anal ecstasy. For more than a full minute, my mind and body seemed to be isolated from each other, and the only thing I could focus on was the deep, sinful pleasure that was roaring through me. When I started to recover from my anal orgasm, I let go of a series of deep sighs and smiled over my shoulder at my talented lover. Feeling a sense of gratitude for the rear end service that he was treating me to, I blurted out, “Thank you Mr. Longwood.”

“I see that you're enjoying this, buddy,” he noted, and I nodded eagerly. “Do you like my cock?”

“Yes,” I hissed, then I batted my eyes at my top. “It's really nice, Mr. Longwood. I loved sucking it, and it feels really good up my butt.”

“I could tell that you were having a good time with it in your mouth, Simon,” he said, and I could only moan and nod my head in agreement. “It's good to know that you're enjoying it right now, too.”

“I am,” I practically hollered out as a wave of orgasmic pleasure washed over me again. “Mr. Longwood?”

“Yes buddy?”

“Can I come over and suck your dick everyday?” I pleaded, then I felt him rub the small of my back.

“Of course you can, kiddo,” he assured me. “Would you like to suck it again today?”

“Yes,” I moaned, then a second anal orgasm touched down like a tornado and ripped through my little body, leaving nothing but chaos in its wake.

“Mr. Longwood is getting ready to shoot another load for you, kiddo,” he said with a smile, filling me with joy. “Do you want it in your tight little keister, or do you want to suck it out of my dick?”

“Can I suck it out of your dick?” I asked submissively, feeling my body shudder all over at the promise of another mouthful of spunk to swallow.

Instead of answering, he tightened his grip on my hips and fed me a set of 15 furious thrusts, then he pulled out and I quickly spun around, anxious to wrap my lips around his prick and suck it. As soon as I had it in my mouth, two strong cum shots squirted directly in my mouth and I moaned with appreciation as they bullied their way in. I smiled up at my top and swallowed, then I licked and sucked him clean all over again.

Before it was time to go, he helped me into my lucky shorts and held me close while I continued to shiver from the pleasure filled butt fuck that I'd just been treated to. Finally, it was getting close to the time I had arranged to start meeting studs at the park, so we shared a deep kiss on the mouth, then he opened his garage door and I rode off.

At the park, things were slow at first, but eventually I found myself flush with plenty of cocks and cum. It was 9:45 when I set up shop in the handicap stall furthest from the door, sitting on the toilet with my shorts bunched around my ankles while I blew the first two studs. After taking their loads, I hinted that I'd be happy to take anything else they had, and they graciously treated me to back to back pee loads. I loved that they both stepped up to my wide opened mouth and used it for what it was there for, then shook off almost casually, as if nothing were out of the ordinary.

Before they left, I let them know that I planned to be there until 12:30, and to come back to see me if they wanted. The third stud to visit me shot a fast load down my gullet, but he stayed rock hard and treated me to a second round of dick sucking. Just when he was about to blow his load for me, he pulled out and jerked off over my smiling face, then he let me suck him clean before beating a hasty exit.

There was a 5 minute lull when he left, so I took a selfie of my cum streaked face and lips, then I updated my social media page to let guys know that I was anxious to suck continuous cock. With that, traffic increased significantly and I found myself on the receiving end of a generous wiener buffet. Shortly after I posted my update, I found myself accommodating up to four studs at any given time, so I quickly gave up my seat on the toilet and got on my knees so I could put my bottom in the air, anxious to have it serviced by a few cocks while the getting was good. While I was being filled at both ends, I took the opportunity to use both of my hands to jack off anyone whose cock was accessible.

While I was in the midst of my first four way cock fest, I pulled off of the dick I was sucking long enough to blatantly announce to my four lovers that they should use me if they needed to pee. With the message clearly sent, I went back to sucking lustily on the dick that was there for my pleasure while my studs talked amongst themselves.

“Holy crap, this little kid does everything,” one of guys I was jerking off said.

“He's like a walking, talking glory hole,” the guy I was blowing observed, and I moaned hotly as I nodded in agreement.

“I wonder if he really drinks piss,” the one fucking my ass pondered out loud, and once again I nodded while I jerked and sucked my lovers off.

“Like a community toilet,” the guy I was blowing said, and the others agreed while I moaned like a slut and gave him a naughty smile.

Much to my delight, all four of them presented me with their pee loads before leaving. Even better, they took turns using my slutty mouth to pee in while three more strangers watched, effectively sending the message for me that I was in the mood for hot cum loads and hot pee loads to be squirted into my mouth.

About an hour later, I was moaning around a big dick while a long, thick shaft was throbbing against the walls of my boy pussy. I was feeling especially slutty, so I used my phone to get back online update my status again. This time, I shared the fact that moments earlier, I'd been sucking a dick, taking one up my butt and stroking one in each hand. I went on to lament the fact that at the moment, I only had a dick in my mouth and one in my rear end, and that I was horny for more cocks to service.

For my shamelessness, I was rewarded with a final uptick in lovers that kept me busy until it was time to leave. At the end of my romp, I had cum strands all over my face, on my butt cheeks and my shirt. My hair was damp with pee, and the seat of my lucky shorts were stained with cum, and damp with drying pee. But I didn't care at all; in fact, I was in a state of sheer bliss as I hiked my shorts and updated my page again.

This time I posted a selfie that showed my disheveled state, then I took a couple of pics of my wet, denim clad bottom. I shared that I'd lost count of how many dicks I sucked, and that I hadn't even bothered to count the number of times I took it up the butt. In a final act of depravity, I posted that my rear end still needed attention, and that I was going to be putting out after lunch. I added that I wanted to keep it busy all afternoon, then I hit post and hurried to see Mr. Longwood again, eager to suck one more cock before lunch.

Up Next: Simon Hits the Alley

Other Work by Josh Terrence: