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 on a Sunday Ho Stroll

My mom sprang the news on me that she was taking me to see the doctor on Saturday night, when I came home from my decadent afternoon behind Mike's bar. She was in the kitchen when I came through the door, but she quickly picked up the stink of anal sex, drying pee and multiple cum loads that was rolling off of my body and out of my hair. She came over to inspect me closer and spotted the dried cum strands in my hair, on my clothes and on my face that I didn't bother trying to clean before I got home.

“Simon, you need to soak in the tub, honey,” was all she said, then she led me up the stairs and ran my bath while I got undressed.

I was checking my gaping boy pussy out in the mirror while she filled the tub, loving how loose and stinky it was. I took the opportunity to hang my bare butt out her way and pull my cheeks apart, eager to show her how slutty I'd been because I knew it would upset her. She gave me a neutral look and went back to drawing my bath, so I took it a step further and slid four fingers up my butt, all the way to the last row of knuckles. When I knew I had her attention, I did the same with my other hand, then I hooked the lips of my gaping butthole and stretched it as far as I could, loving how loose and pliable it was. My puny boy boner, which had been sticking straight out from my body, suddenly stood up straight and my little nut sack pulled tight.

“I got laid up the butt all afternoon,” I taunted her, then I turned back to the mirror and checked out my busy rear end. With my fingers stretching it out, the gap was bigger than 3 inches from end to end, and I loved how I could feel the difference in temperature as the cooler air in the room filled the opening. Looking at the reflection, I could effortlessly see deep into my rectum, where hot strands of cum were dangling along the hollowed out lining. I wondered to myself if I could fit my whole hand inside, and if I could, how good it would feel.

While I was admiring my tingling, gaping hole, she mentioned that she made an appointment for me to see a new pediatrician.

“You have a doctor's appointment on Monday afternoon, Simon,” she told me. “I'm taking you to a new pediatrician so I can get you a referral to see a counselor.”

“I don't need to see a counselor,” I countered, and she let her eyes roam back to the mirror, where my distended hole was still on display.

“Honey, I don't know what else to do with you,” she said, her tone still neutral. “You're 12 years old, and you're sleeping with grown men.”

“Because I like it,” I said, following her gaze to my hole, which I was still holding open with my fingers. Still using a defiant tone, I added, “I wish I could have gotten laid even longer.”

“Simon, you told me you were going to take down the posts you made this morning,” she reminded me. “Instead of doing that, you've been posting crude things all afternoon on your page.”

“So, I like posting that stuff because I want everyone to know when I'm being slutty,” I argued, pulling one set of fingers out of my hole and licking them clean with a naughty smile. Then, with a defiant gaze, I hung my bottom back out her way and made direct eye contact with her, then I started working my four fingers back and forth in my sloppy hole. Right away, a powerful shiver washed over me and the squelch of the many cum loads in my ass became audible as I anally masturbated right in front of her.

“Simon, what are you doing?” she asked, her tone troubled this time.

“I'm being slutty,” I moaned softly, maintaining eye contact while the hot stink of my bubble butt intensified in our nostrils. “I'm going to make sure that I get laid more times tomorrow than I did today.”

With that, she shut the water off and walked out of the bathroom while I enjoyed a few more moments of anal stimulation.

Anxious to keep my promise, I got on my social media page as soon as I was out of the tub. I announced that I was planning to spend all day Sunday putting out in the alley, and that I wanted to lose count of the dicks that used my hole, and I was hoping to lose count quickly. When my mom demanded that I take the post down, I defiantly ignored her.

When she persisted, I responded by climbing onto the coffee table and putting my underwear clad bubble butt in the air, then I snapped a series of naughty selfies. I made sure that I was looking over my shoulder with a lascivious stare so that it would be clear that I was in the mood for anal sex. Over the protests of my mom, I posted all of the photos with captions that served as blatant invitations for anyone who wanted to get off to come see me in the alley. Before I went to bed, I put up final post announcing that I was planning to lose my shorts early in the morning, and that I wanted my rear end to stay busy from sun up to sundown.

Just as I promised, I got there bright and early with my rear end lubed up and ready for penetration. Happily, there was a group of studs waiting on my arrival, and I spent the day with my shorts down and my ass in the air, inviting cock after cock to slide deep in my boy pussy. Almost as an afterthought, I sucked every dick that was presented to me and gave several delicious rim jobs. I swallowed as much cum as I could, and drank quite a few bladderfuls of hot pee for good measure. As I scaled the heights of gay decadence, I updated my social media page throughout the day with naughty selfies and vivid details so that my mom would know how slutty I was being.

When I didn't go home for lunch, she called my cell phone to find out where I was. I had my face buried in a set of hot ass cheeks, tonguing out a deliciously swampy butthole while my own bubble butt was accommodating a hard prick. I heard her ringtone and answered the call on purpose, then I held the phone up to my face so she could hear me moaning up into the ass I was eating. For good measure, I called out, “Your butthole tastes so good,” then I proceeded to lick and slurp as loud as I could so she could hear it. When she didn't hang up right away, I decided to add, “When I finish eating your butt out, I want to suck your dick again, okay?”

Seconds later, the call ended and I knew she'd heard everything. When she called back 5 minutes later, I was sucking lustily on my man's dick while a new cock was working deep in my boy cunt. I answered on purpose, then proceeded to continue sucking and slurping on the dick I was enjoying while the hot buttfuck I was taking made me moan like a little girl. I took care to place the phone right at my butt cheeks, where the loud slapping sound of my top's hips matched the timing of my pleasure filled moans.

Thirty minutes later, a cute 13 year old named Mitchell showed up looking for a dick or two to suck. I was laying flat on the table top with my knees pulled to my chest, taking a missionary style fuck when his luscious bubble butt came into view. His blonde hair was a bit messy, and he looked like he'd just rolled out of bed and got dressed without worrying about a shower. He was wearing a plain white tee shirt and a pair of blue jeans that looked like they hadn't been washed in weeks and had a hot fart or two trapped in their seat.

He was on his knees right away, blowing a cute 26 year old named Stuart while I watched from the table. His shirt tail pulled up and I spotted the blue striped waistband of his white cotton briefs, and I immediately started fantasizing about sniffing their skid marked seat. I felt a slutty thrill run through me as I dreamed about tonguing his hot stink button. Just pondering the likely dirty condition of his butthole was making my mouth water, so I waited for him to finish blowing his stud, then I lured him over to the table.

By that time, I'd been bred by my top and a new stud was inside of me, making my legs rock back and forth with the motion of our ride. As soon as I locked eyes with Mitchell, he smiled and planted a deep kiss on my mouth while I moaned submissively. I could taste the cum on his breath, and as his tongue stirred in my mouth, I dreamed about eating his filthy hole. When we broke our kiss, I translated my desires to him, and he responded by dropping his pants and climbing onto the table top. He lowered his creamy white globes onto my grinning face and as they came to rest, his crevice widened and I spotted a delightful treat that was resting in his crack, smashed between his cheeks and presented for my enjoyment. My head was spinning with pure pleasure as his bubble butt made contact with my face. Acting on sheer instinct, I took a deep whiff and had a punishing boygasm that caused my top to blow his load in my rear end.

The stink was incredibly powerful, and quite pleasant as I drew it into my nose. It had the distinct aroma of fresh poop, dark but also sweet and pungent, and I was loving having it swirl around my face. I could feel the swampy heat of Mitchell's unkempt, chocolaty pucker against my lips, so I eagerly opened wide and a thrust of hot, stink filled air swirled into my mouth. Filled with desire, I used my lips to form a tight seal around his stink button and used my tongue to take deep licks, pulling the decadent butt fudge that rested between his buns into my mouth. With a mouthful of thick, naughty goodness, I savored my treat while another powerful boygasm washed over me, then I swallowed. With my stinky treat down, I sucked diligently on his pucker, eager to draw out more of the flavor I was enjoying. Next, I licked along his crevice, starting as far as the tip of my tongue would stretch and running it all the way to his sweaty taint.

Unable to control myself, I grabbed onto his hips and encouraged him to grind his tasty butt into my face. I loved how my lips and tongue smashed directly into his pucker while his soft buns massaged my cheeks. My nose was buried deep in his crack, treating me to its naughty aroma and perfect temperature, letting me get the most out of every deep whiff I indulged in. The delightful flavor of poop was powerful in my mouth while the stink permeated my hair and skin on my face. Each and every time I lanced out with my tongue, I was treated to a powerful flavor explosion that had my head spinning with pleasure. So, filled with nothing but desire, I found myself eating greedily at his 13 year old poop chute.

While I was tonguing the delicious and unmistakable flavor out of Mitchell's filthy stink hole, I felt my legs being lifted again and a new cock was inserted into my ass. I was moaning up into the hot rear end I was eating when I heard a man and a boy talking about me.

“Damn, son, his ass is nice and tight,” I heard my top telling someone, but I knew it wasn't Mitchell as soon as the boy spoke.

“Does he like it?” I heard a much younger boy ask, and I moaned with depravity and nodded into Mitchell's ass cheeks.

“He loves it, buddy,” the man said. “Do you want to take a turn?”

“Sure!” I heard an excited voice say. “His boner is tiny, dad.”

“I don't think he cares how big or small his dick gets, buddy,” the man said, and I wanted to announce that he was right, but the treasure trove that I'd come across in Mitchell's rear end had my tongue working in a frenzy to lick as deeply and as often as I could.

With that, the man fed me a flurry of strokes, then he pulled out and I heard Mitchell moaning and slurping, and I knew he was finishing my top off for me. Once he presented his load to my 13 year old companion, the man guided his son's dick into my ass, and I was sure it would be the smallest prick I'd take all day. The boy thrusted clumsily for about 30 seconds, then he sighed and I knew he'd achieved his dry orgasm.

When he pulled out, a much larger top took his place and I moaned with delight, then reluctantly, I had to part with Mitchell's delicious rear end. The cutie treated me to one more makeout session, then he walked up to a cute stud and made a pass at him while a hard prick was eased into my mouth. I watched as Mitchell dropped to his knees and sucked dick for his stud, and eventually, pulled his knees to his chest and had his rear end serviced with the shaft he'd just been moaning around.

For the rest of the day, I received an assortment of different pricks. Just after 3pm, a man brought his twin 10 year old sons to see me, and just like the boy before them, they compared their boners to mine and we discovered that I had the smallest one. I loved that these two cute 10 year olds were more well endowed than I was, and I eagerly let them have their way in my boy pussy. I even had the pleasure of eating one of their dirty, unkempt asses, and was treated to a generous mouthful of boy poop that was waiting in the hot crevice of my top. As soon as I came across the naughty treat, I moaned with depravity and pulled it into my mouth with a hard grin. Grateful for my stinky surprise, I tongued his dirty hole with devotion, licking it clean while their dad pumped a hot load up my keister, then they both fucked me again.

When I was supposed to leave, I still had a massive prick working in my hole and another one was being waved under my nose. I was laying on my side on the picnic table, holding my right leg up to my chest while I moaned lasciviously at the group of tops that were watching me. I knew I was being gluttonous, but I disregarded the alarm on my phone and stayed longer, eager for as much back door action as I could enjoy. By the time the final dick was eased into my hole, I hardly cared about the pleasure I was receiving and instead focused on the slutty sensations that were coursing through my little body. I knew that I'd taken cocks of all sizes just for the sake of taking them, and that I had been even sluttier than I planned on being, but I loved it.

I was more than an hour late for my curfew when I got home, and I was sure I was going to be in trouble with my mom. Instead, she calmly went upstairs and started a bath for me while I went to my room and tossed my lucky shorts behind my dresser for safe keeping. I went into the bathroom where she was sitting on the tub, and immediately started taunting her again.

Making sure that I had her attention, I parted my butt cheeks and showed her my loose, cum sopped pucker. It looked even more dilated than it had been the night before, easily 4 inches from end to end, and I loved how I was able to hook it with two fingers on both hands and hold it open. It's stink was dark and prominent, and I could feel the remaining cum loads trickling along its walls while I stretched it out.

“I don't remember how many times I took it up the butt today,” I boasted, noting that her eyes were trained on my high traffic boy pussy. “I don't remember how many times I gave head, either.”

“Honey, that's nothing to brag about,” she said in a soft tone, but I nodded my head in disagreement with her and went on.

“It was early in the morning when I couldn't remember anymore how many guys did me in the butt,” I admitted, locking eyes with her before I continued. “And guess what else I forgot?”

Instead of answering, she gave me a neutral look, so with a taunting grin, I said, “I forgot how many dirty buttholes I licked out today and how many times I drank pee.”

“Honey, that's not a nice thing to talk about,” she reminded me, but I only responded with a moan as I easily slipped all five digits of my right hand into my gaping hole. Her eyes got big when she saw me shove four fingers and my thumb into my hole, so I capitalized on the opportunity.

“I liked eating those butts,” I said with a catch in my voice. “They were nice and stinky, and guess what they tasted like, mommy.”

“Simon, let's not do this tonight,” she said, turning for a moment to check the water level in the tub.

When I had her attention again, I boasted, “They smelled and tasted like poop, and I loved it. Every time I eat a whole bunch of different buttholes, I get lucky and get a big mouthful of poop. It tastes so good, and I like to smash it with my tongue and wash it down with pee. That's what happened today, too.”

“Honey, I hope you're fibbing,” she said in a patient tone, and I shook my head no.

“I had poop twice today,” I bragged, licking my lips as I remembered the various asses that I'd eaten, especially the two hot boy butts that provided me with the taboo experience that I was bragging about. With a defiant tone, I added, “I like it when guys poop in my mouth. I wish I could have poop all day.”

With that, I started strumming my boy pussy with all five fingers while she watched with troubled eyes. I could feel my body shiver while my eyes glazed over with pleasure, then the already powerful stink in the bathroom seemed to quadruple in strength. My tiny boy boner was standing straight up, pressed tight to my bald pubic bone and the moist squelch of the many cum loads in my bottom was loud. I started panting as the pleasure overtook me, then I started to moan.

When my bath was ready, she said in a soft voice, “Simon, baby, I want you to stop what you're doing and get in the tub. Mommy's got your dinner plate in the oven, and I'll put some clean undies out for you, okay?”

Instead of responding to what she just said, I looked at her and increased the pressure of my fingering, then I promised her, “Tomorrow I'm gonna get laid again before we go to see the doctor.”

“Well, sweetie, I wish you wouldn't, but I'm sure you will,” she said, and I let go of a hot moan as I nodded in the affirmative.

“I'm gonna lick dirty butts at school, too” I added as a hard shiver consumed me. “I hope I get to eat a few extra-dirty buttholes while I'm doing it. After school, I'm gonna eat filthy, poopy butts and drink some more pee.”

With that, I bent over so that my butt was practically in her face and strummed my hole with a purpose for several more moments, then I pulled my brown, poop coated fingers out and made a show out of licking them clean while she watched with an emotionless stare. In a final act of defiance, I pulled my butt cheeks apart one more time, eager to show off my massively distended hole, then I got in the tub and soaked while she went down the hall and put some clean undies out for me.

When I got out of the tub, I got into my undies and went to the supper table. While I was eating, she told me that she made my appointment for 5pm on Monday, but that I'd have to meet her at the doctor's office because she wasn't able to leave work early enough to come pick me up.

Armed with that knowledge, I made plans to hurry home on Monday and get into my lucky shorts, then ride my bike to the alley for some back door action.

Up Next: Simon's New Doctor

Other Work by Josh Terrence: