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 Hits the Alley

After leaving Mr. Longwood, I rode my bike home and checked in for lunch. Of course, my mom had seen all of my posts online, and quickly confronted me when I got home.

“Simon, I'm not going to tell you again,” she admonished me when I rode my bike into the garage, where she was sorting laundry. “I want you to take every one of those posts down right now.”

“What if I just take down the ones that I put up this morning before I rode my bike?” I offered, and she adamantly shook her head no. With a sigh of resignation, I said, “Fine, I'll take them down after lunch.”

“Thank you, sweetie,” she said, and I moved to her for a hug. As soon as I wrapped my arms around her waist, she picked up the odor of oral sex and anal sex that was rolling off of my body, then she smelled the drying pee that had soaked into my shorts and hair. She gave me a sniff and made a face when I released our hug.

“Honey, you smell like you've been playing in the sewer,” she said, fanning the smell away from her face while I grinned up at her with a naughty expression. “How about if you soak in the tub and stay in for the rest of the day?”

Shaking my head no, I reminded her, “You said I could ride my bike all day.”

With a deep sigh, she countered, “Simon, I want you to take a shower and put something different on. You know how I feel about those shorts. Besides, they stink.”

“But I like these shorts,” I taunted her, letting my gaze travel over my shoulder to my barely contained bubble butt. “They're my lucky shorts, mom, and they've been working all morning.”

“That's enough, Simon,” she said shortly, then her expression softened and she let go of a deep sigh. “Lunch is on the table, baby. I made your favorite.”

“Thanks mama,” I said, accepting her peace offering with a sweet smile. “Mommy?”

“Yes, baby?”

“If I take a bath, will you wash my shorts while I eat lunch?”

“Take them off and give them to mama,” she instructed me, so I did as I was told, watching her drop them in the washing machine and start the cycle. I went upstairs and admired my stinky butt hole in the mirror while I waited for her to run my bath, then I got in and soaked while I finger banged myself in the tub. I came to the lunch table naked from the waist down over the protests of my mom, who realized that the only way I would be putting any pants on would be if I had my lucky shorts. So she promptly put them in the dryer while I was eating, and I slipped back into them as soon as they came out.

After lunch, I “forgot” to remove the naughty posts from my social media page, Instead, I hopped back on my bike and went on the prowl. I made up my mind fairly quickly that I was going to ride to the gay district and see how much action I could get. I knew that if I rode my bike down the alley behind the gay bar I'd have my best luck, but it was still a little early and I wasn't sure how much action I would see.

Much to my surprise, the alley was bustling with activity when I coasted into it from the sidewalk. Realizing that I was probably going to be able to lock my bike up and stay put for the rest of the afternoon, I made a point of standing on my pedals and showing my plump, horny rear end off as I rolled past a quartet of hunky looking men who were gathered around an old wooden picnic table. Wanting to send a clear signal that I was there for sex, I blatantly ogled their crotches as I rode by, then I gave my aroused rear end a sensual roll.

Just then, I heard a familiar voice call my name out.

“Well hey buddy,” I heard from the back door of the bar, and looked up just in time to see the owner, Mike, giving me the eye.

“Hi Mike,” I said with a husky tone in my voice, feeling overwhelmed with desire as I coasted his way and stopped.

Besides being the owner of the bar, Mike is a bonafide stud. He's tall, dark and handsome, with a nice, hard body that I love to let my hands roam while I'm in the missionary position beneath him, having my hole drilled by his jumbo sized mancock. Normally, Mike takes me through the back door of his bar to his office, where he has a comfy couch that we makeout on before he treats me to a thorough rear end service.

“You want to bring your bike inside where I can keep a close eye on it?” he offered me, and I quickly agreed to this arrangement. I hopped off of my bike and handed it to my stud, then I followed him to his office. As soon as my bike was resting against the wall, Mike took a seat on the couch and I made a pass at him.

In no time flat, my shorts were bunched around my ankles while I pulled my knees to my chest, presenting my horny hole for Mike's use. His hot prick slid deep into my waiting boy pussy, then he ran it back and forth while I moaned like a little girl. Five minutes later, I hiked my lucky shorts and shared a deep kiss with my stud, then I hurried back out to the alley and made a pass at the gathering of hunks that had me so hot and bothered.

“You guys are all cute,” I lisped right away as I sauntered up to the quartet sitting at the picnic table, letting my hips swing gayly from side to side as I walked, and that was all it took.

“You're quite a little cutie yourself,” one of them answered in a deep, manly voice that sent a strong shiver of desire through me as he rested his hand on my shoulder. “And from what I hear, you've earned yourself quite a reputation around here with everyone.”

Batting my eyes at him, I responded by admitting, “I was hoping to spread my reputation some more.”

“Oh yeah?” he said, almost daring me to try my best, so I took him up on his challenge by nodding at him. “Well, what did you have in mind?”

“I was thinking that maybe I could start by kissing all of you,” I offered, my voice husky with desire as my eyes roamed up and down all of their sculpted frames. “Then maybe I can show all of you how good I am at giving head.”

“Oh really?” he said, his expression still one of amusement, and I nodded again. “Did you have anything else in mind?”

“Yeah,” I said, running my hands all over his toned chest through his shirt. “I was thinking that while I was giving head, all of you could take turns doing me up the butt.”

“Well that sounds very hot, little man,” he said, then I felt the hot breath of one of the other men against my neck and looked around to find that the rest of them were kneeling around me. “Did you have anything else in mind?”

Nodding almost hypnotically, I added, “I want all of you to take more than one turn doing me up the butt.”

“You sound very horny, buddy,” he observed, and I moaned in response. “How long has it been since your last fuck?”

“A couple of minutes ago,” I revealed, and his eyes lit up with excitement. “But I want to get laid again right away.”

With that, I leaned in and planted a deep French kiss on his mouth, then we broke our kiss and I found myself with another mouthful of tongue, then another and then yet another. For several moments, I found myself enjoying a daisy chain of kisses, luxuriating in the strong, delicious tongues of all four men while they took turns groping and pinching my bubble butt. In the background, I could hear the knowing comments from the other men in the alley as they watched me operate. I loved that I had an audience, and I knew that all of them were well aware that once my quartet of studs were finished getting off in my mouth and ass, I wanted each and every one of them to take as many turns as they wanted.

With my mouth still filled with wet tongue, I dropped my shorts, eager for things to move along. Being kissed up by these four strangers was getting me hot and bothered for an exhaustive rear end service, and I wanted to send the signal that it was time for them to lose their pants, too.

Much to my delight, my message was received loud and clear, as one by one, they started to disrobe for me. It became obvious to me while they were still dressed that they were all well endowed, but as soon as their hard pricks came into view, I found myself longing to suck continuous cock for them while my back door service commenced.

Not long after my shorts hit the ground, a juicy cock was waved in front of my face and I promptly wrapped my lips around it. Holding onto the tops of my thighs for leverage, I found myself taking all 8 ½ inches with a needy set of moans while a strong set of hands parted my exposed butt cheeks. Seconds later, the flutter of warm breath filled my crack, then I felt my body start to melt down as a strong, wet tongue feasted on my freshly bred boy box.

Moments later, my anonymous feaster abandoned the rim job he was giving me and I felt him grab me by the hips. Anxious for a big dick to fill my hole, I cast my needy eyes up at the stranger I was blowing and moaned like a little harlot as the moist helmet of a dick pressed up to my entrance. I spread my feet as far apart as I knew I needed to, and with no resistance at all, I felt my rear end fill up with a long, meaty shaft that was radiating with heat and throbbing against the walls of my boy cunt.

Before I knew what had come over me, I was laying on my back on top of the picnic table in the missionary position. I had a cock in my mouth, one in my ass and one in each hand, and my sluttiest desires were being met. My continuous, satisfied moans were only muffled by the meaty pricks that I simply had to suck while my pooper climaxed repeatedly for the duration of our sex. One by one, all four of the strangers took turns hammering my rear end and getting off in my mouth, then doing it all over again. I loved that everyone in the alley could see me slutting it up with these four strangers, and I quickly decided that I wanted everyone online to know what I was up to.

By the time they were finished using me for their pleasure, I was in a state of sheer delirium and quickly updated my social media page. I blatantly posted that I'd just put out for four big dicked studs, then I posted another update advertising my rear end as not only available for sex, but yearning for it. As soon as my naughty updates were posted, I opened my legs and started putting out for the rest of the men in the alley.

Much to my delight, I spent the rest of the afternoon welcoming generous sized cocks in my mouth and ass while I begged for more. At one point, I found myself luxuriating in a deep, pleasure filled ass fucking that had my legs shaking uncontrollably while everyone watched. When my top was ready to breed me, he pulled out and shot his load all over my face and torso. While I was sucking his cock clean, I kept my thighs spread and another hot dick was eased into my rear end.

While I was enjoying the action in my boy pussy, I took my phone out and took a naughty selfie of my cum streaked face and puffy lips. In the picture, my legs were clearly dangling in the air and I had a look of sheer lasciviousness on my face that made it obvious that I was taking it in the ass. But I was in such a slutty mood that I didn't care who saw it, and quickly placed it on my page along with a shameless caption letting everyone know that I was receiving uninterrupted anal sex and wanted it to continue all day.

Later in the afternoon, I was in the doggy style position, taking the biggest dick I'd enjoyed all day and loving it. The cock was so massive that before it went up my ass, I begged to suck it for a few minutes. Giving into my wishes, my top watched with bemusement while I worked to deep throat the 11 inch trophy. My lips were stretched and my mouth was filled to the brim, but I took it like a true cock hound. In no time flat, I had the massive pipe in my throat and experienced a fast, punishing boygasm while I moaned like a bitch in heat.

When the arousal in my boy pussy started to overwhelm me, I pulled the big dick out of my mouth and climbed back onto the table top with my ass sticking straight up in the air. I watched with bated breath as the cock I was so hot for was placed against my yearning, gaping hole. A glob of precum rolled out of the end and made me moan as it painted my winking pucker, then I impatiently pushed back with my hips. And just like that, my hungry rear end swallowed all 11 inches with ease while an amazed crowd watched.

Realizing how fascinated everyone was with how easily I took the big dick, I reached back and parted my butt cheeks with a naughty smile. I was anxious for everyone to see the massive fuck stick fill my hot boy pussy, then I let my butt cheeks go and my top started to thrust in and out of my distended hole. While I was taking all 11 inches with whorish moans, a hot prick was presented to me for sucking. Acting on pure instinct, I wrapped my lips around the hard dick that I was longing to suck. I loved that there was a large group watching me take a massive fuck stick in my rear end while I moaned around a hot dick in my mouth.

A few minutes into the pleasure filled double dicking that I was enjoying, the prick in my mouth blasted off and I swallowed a luscious load. When the dick was eased out of my mouth, someone walked up and pulled my ass cheeks back apart so everyone could watch the big dick that was running deep in my boy cunt. I heard someone mention how loose my ass looked with that massive prick filling it, and I felt another thrill run through me.

While I was letting go of slutty moans, I got on my phone and updated my page again. I boasted about the big cock I had just sucked, and the hot, gooey load that I'd swallowed. Unable to resist the temptation to be as naughty as possible, I immediately posted another update about the cock ride I was enjoying so much. In my post, I let everyone know that the entire time I was sucking that luscious dick, I had been taking it up the butt. Then I shared the fact that I was still getting laid by a stud with a huge dick, and that I wanted more of the same for the rest of the day.

Fifteen minutes after he first slid his trophy sized pleasure stick up my butt, my stud pulled out and shot his load all over my ass cheeks and my dilated entrance. I took particular pleasure in sucking his rod clean while another cock slid into my stink hole and got off. When I had to relinquish the 11 inch trophy for the final time, my lips were incredibly puffy and red, so I took another selfie and put it online.

As soon as I posted each update, they were shared over and over again, just like most of my other updates. Traffic in the alley picked up, and I was able to just lay back and keep my legs spread while cocks entered me at both ends. At one point, I was laying on my back with a hard prick up my butt and a cock in each hand, lustily taking turns sucking on each one while a pair of hunks jacked off over my glowing face. My head was spinning with so much pleasure that I barely noticed that a cute blonde who had topped me twice had walked back up to me until he unleashed his pee stream on my chest and in my face and hair.

Realizing that I was at my absolute sluttiest moment, I moaned like a girl and smiled around the dick that I had in my mouth. His warm stream seemed to awaken something even naughtier in me than I knew, and I took nothing but pleasure in watching as his yellow elixir ran down my chest to my heaving tummy, where it collected around my navel. As the afternoon wore on, another cutie walked up to me while I was in the doggy style position and peed all over my butt cheeks. When his flow ended, he offered me his dick by waving it under my nose. I promptly wrapped my lips around his luscious man meat and was rewarded when he shot three squirts of pee into my mouth, then he dribbled the rest over my smiling face.

When it was time for me to go home, I had cum shots all over my body. My hair smelled like dry pee, and so did my body. My pucker was gaping wide and dripping with cum, and I was in a state of sheer Nirvana. My shorts were on the ground under the picnic table, where I had dropped them at the start of my romp. Without bothering to get dressed, I picked them up from the ground and carried them with me into Michael's office to retrieve my bike and get myself laid one last time. Michael noted my disheveled state while I sighed contentedly, then I bent over for him. I was treated to a quick, dirty fuck that I took while I held onto his desk for balance, then I hiked my lucky shorts and rode home, planning to return the next day.

Up Next: Simon goes on a Sunday Ho Stroll

Other Work by Josh Terrence: