Tyler Tries Anal Sex

🏳️‍🌈 A short story by Josh Terrence 🏳️‍🌈

bb/oral/anal/mast/rimming

Author's note: This short story depicts sexual acts between males of various ages. If you are offended by sex between men, teenage boys, 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 fictíon. 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.

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Other content featuring this character in chronological order-

Tyler Goes Gay

Tyler Gets Lucky

Feedback: jtstories@tutanota.com

🏳️‍🌈

"Hey mom, can I ride my board?" I asked shyly, holding my skateboard in one hand and my helmet in the other.

"Will you be home by 2?" she asked, looking up from her phone and giving me a warm smile.

"Yeah," I promised, returning her smile with one of my own.

"Give me a kiss, munchkin," she said, so I planted a kiss on her cheek before hurrying out the front door. Dad was working under the hood of his project car when the storm door closed behind me and I laid my board down to secure my head gear. He looked up and motioned me over to him with his head, so I obediently complied.

"Where you off to, munchkin?" dad asked as I kicked my board up from the ground and grabbed it with my right hand.

"I'm riding down to the skate park," I told him, stopping in front of him so he could adjust the straps of my head gear. "Mom said I could stay out until 2 this afternoon."

"Oh yeah?" dad said with a warm smile, giving the two straps a final pull to snug them up against my chin. He reached out with his hand and tickled my ribs, making me squirm as he said, "Have fun, champ. Don't forget we have plans tonight."

"I won't," I said with a smile, then I gave him a hug around his waist before laying my board down and riding off.

As soon as I was out of view, I reached into my front pocket and pulled out my pride bracelet so I could wear it at the park. I've been trying to figure out how to come out to my parents, but I haven't found the words just yet. I was thinking about coming out to them after I turn 12 in a few months, but I was also thinking about doing it sooner. It's not that I think they'll have a bad reaction when I tell them. I'm just scared to go through with it right now.

When I got to the park there were a bevy of cute guys on the halfpipe, but one in particular caught my attention. It was Parker, a cute 9^th grader I've been talking to for a couple weeks. His brother Ronnie goes to my school and I've been walking home with him everyday so I can give him head.

The first time I sucked him off, it was in my backyard. Mom was home so we had to sneak through the gate and hide on the side of the house, but it was so magical and so sinful that I wanted to do it again. So the next day I stopped at his house and gave him a long, sloppy blowjob that ended when he treated me to a mouthful of spunk that I swallowed with a satisfied sigh.

After that, I started blowing him every day after school and even on the weekends. If I don't get a mouthful of his yummy cock and cum, I get a little irritable. Mom and dad can always tell when I'm not my normal chipper self and I don't want to make them suspicious, so I make sure I get my fill.

Not long after I started hooking up with Ronnie, I bumped into Parker and ended up on my knees for him, too. His dick is so juicy, and it has a lot of hair! I love sucking it while I run my fingers through his pubes and smell his musk. Plus, he shoots really big loads that feel so good when they slide down my throat and into my tummy!

One day he showed up while I was on my tummy, blowing Ronnie in his bed. He crawled up behind me and massaged my butt cheeks. When I moaned with desire, he pulled my school pants down and bared my 11 year old bubble butt. I moaned urgently when my bare butt was exposed to the room, then he parted my buns and planted his nose in my crevice. He took a deep whiff and shuddered while I swung my feet back and forth in the air, then he spread my buns and latched onto my pucker.

I've been eaten out before, so I knew right away what he was doing. It felt so good, especially when he sucked on my hole while his tongue flicked against its lips. Having a dick in my mouth while my bubble butt was being serviced felt so good. It made me feel like I knew what I wanted all the time. When Ronnie ran his fingertips through my hair and squirted his load in my mouth, my body was burning with pleasure and desire.

I sat up and let my head fall backwards into Parker's shoulder so we could share a kiss with a lot of tongue, then I went down on him and sucked his big boy cock. He squirted a fast but yummy load into my mouth while Ronnie locked his fingers behind his head and watched with a grin. I smiled up at him and swallowed, then he rubbed my hole while I licked and sucked strands of boy sperm from his equipment.

The next day, him and Ronnie took turns eating me out while I blew them with hot moans that gave away my desires. The day after that, they started fingering me and talking with each other about taking me up the butt. Hearing them talk about doing full anal with me had me moist and hungry for it right away, but they always stopped just short of sliding their dicks up my butt. After that, we settled into a routine of me blowing them while they finger fucked me and ate me out, and it was pure bliss for me.

One day I was blowing Ronnie in his room when Parker pulled me up at the hips and placed his dick against my butthole. The head of his prick felt so hot and powerful as it pressed into my pucker, then hot shots of cum erupted and I was in heaven. I could feel gobs of cum painting my butthole and running into my crevice, and loved it. After that, he started shooting most of his loads against my butthole instead of in my mouth, then he'd finger his cum into my butt while I moaned blissfully around Ronnie's 13 year old equipment. I've been waiting for him or Ronnie to finally stick their dicks inside, but for some reason they never go through with it.

But when I saw him standing on the ledge of the halfpipe, I felt my rear end shiver and decided that today had to be the day. He smiled when he saw me ride up and I blushed, then I stepped off my board and approached him.

"Hey dude," he said while my cheeks turned three shades of red.

"Hey Parker," I cooed, then he spotted my pride bracelet and grinned. "What are you up to?"

"Just screwing around," he said. "What about you?"

"I wanted to see if you feel like going with me to the dugout," I said, motioning with my head to the empty ball field. "Is Ronnie around?"

"He's around here somewhere," he said, then we started walking toward the ball field. "What did you have in mind?"

I shrugged as we walked side by side, then I blurted out, "I was kinda hoping that today would be the day."

He stopped in his tracks and gave me a skeptical look while I looked up at him with nervous eyes, then a smile broke out on his face and he said, "Let's see what happens."

"Okay!" I said a little too enthusiastically, then I blushed again.

He reached out and brushed my bangs out of my eyes, then he said, "You look so cute today."

"You look really cute, too," I smiled, then we walked to the nearest dugout while he texted his brother to come join us.

As soon as we were in the dugout, he sat on the bench and I stood in front of him so we could kiss. Our lips met and our tongues touched, making my head spin right away. Before I knew it, we'd fallen into a long makeout session that swept me off my feet while he slid his palm into the seat of my shorts and found my hungry hole. I moaned into his mouth while he rubbed the outside, then he slipped his finger up my butt and my moaning took on a more passive tone.

Without warning, he broke our kiss and said, "I need to eat your ass," then he pulled his digit out of my hole and practically yanked my pants and undies down. I found myself on my knees on the bench, holding onto the backrest while he spread my cheeks and feasted on my pucker. In no time flat, I found myself in a carnal haze while he ate me out. The sexual fog was so thick that I didn't realize we'd been joined by Ronnie until he pressed his lips up to mine. My eyes fluttered and his cute face was smiling as our lips touched, then our mouths opened and we French kissed.

In the midst of our kiss, Parker abandoned the rim job and hissed, "He wants us to fuck him, buddy. Will you go first?"

My head was spinning out of control when Ronnie nodded without breaking our kiss. Parker placed the head of his prick against my butthole and jacked off, then his load splattered against my pucker with force while I moaned like a whore. Seconds later, he fingered his sperm into my hole with one finger, then two. With two fingers in my ass, he reached out with his free hand and caressed Ronnie's face, prompting him to break our kiss.

"He's ready right now," Parker hissed, sounding almost frantic while my hot rectum flexed around his digits. In a flash, Ronnie yanked his shorts down at the front while I reached back and pried my buns apart so he could see my hole.

"Fuck, he looks so slutty," I heard a familiar voice say from the entrance of the dugout. I turned my head and saw a trio of boys from my school, Matt, Cameron and Max, watching as I prepared to get my ass fucked. The three 8^th graders were at the halfpipe when I arrived and made their way to the dugout. Now they were watching us while they groped themselves, but I made no move to stop what I was doing. Instead, I blatantly ogled their packages, then I looked back as Ronnie put the head of his 3 ½ incher up to my hole. We were both breathing heavily when he pushed it in while we made eye contact. His head melted through my entrance and we shared a smile, then it slipped in and I sighed. He puckered his lips and we kissed, then he held onto my hips and began thrusting while I moaned.

My first lay was absolutely magical.

His dick was taking full strokes that felt amazing. It was the pleasure of 10 rim jobs combined, spreading through my body while I dug my fingertips into my buttcheeks and shivered. My thighs and groin were burning sweetly as he worked his boy boner back and forth and pressed his lips against mine.

Less than 60 seconds into our ride, he froze and his face scrunched up, then it melted into a blissful smile and his tongue slipped into my mouth. We let our tongues dance for a few blissful moments, then he pulled out of me and Parker gave me a questioning look. Knowing what he was asking, I nodded and sighed, "Yes, please."

With a confident smile, he placed the head of his big boy prick up to my yearning hole and carefully entered me. His glans felt like sheer masculinity as they pushed past my anal ring, intensifying the sweet burn in my thighs and groin. When they were inside, he pushed again and all 5 inches were received.

I sighed with relief, then smiled over at the entrance of the dugout where the trio of boys were still watching. Parker's cock felt like a beating heart against the walls of my hungry chute, throbbing with authority while his mane of pubes scrubbed my crevice. When he tightened his grip on my hips and started to thrust, I moaned with carnal pleasure and felt my 4'5" body take flight for the duration of my ride.

Like his brother, Parker's endurance was no match for the heat and tightness of my hungry boy butt. He fed me a little more than 45 seconds worth of thrusts, then he buried his pleasure stick up my ass and bred me. While he was getting off inside me, my head lolled back and he filled my mouth with stiff tongue while I cooed with delight.

When he pulled out, I spread my buttcheeks a little further so he and Ronnie could see what they did to my hole, then I let them close and sat on my butt so I could suck my studs clean. My little dick was on fire, standing straight up while I moaned blissfully around the two dicks that had pleasured me.

While I was still grinning and blowing my lovers, Matt walked up to me with his dick out and stroked it in my face. I turned my attention to him by slipping my mouth over the head of his dick, and my instant reward was a hot rope of boy batter that glanced off the roof of my mouth. I smiled up at him and swallowed, then I worshiped all three dicks for a few more minutes.

Finally, my three studs hiked their pants, so I got up and did the same. Much to my delight, Parker and Ronnie each took one of my hands and sat with me while Matt and the others walked back to the halfpipe. I shared a sweet kiss on the lips with Ronnie while Parker rubbed my back and talked tenderly to me.

"Are you okay?" he asked, and I nodded with a blissful smile.

"I feel so perfect right now," I declared, then I rested my head on his shoulder and smiled at Ronnie. "Thank you, guys. I've been wanting it so bad."

"Do you want to do it after school with us?" Ronnie asked curiously. When I nodded my eager reply, he smiled and said, "I promise."

"Did it feel good for you?" I asked them both.

"It was incredible, dude," Parker marveled. "Your ass felt like an oven. A tight, moist oven."

"Yeah, it was the best," Ronnie agreed. "I can't wait to fuck you again."

"Well we don't have to wait," I offered them, rubbing Ronnie's thigh. "We can go again if you want."

"Let's see how you feel later," Parker cautioned me. "My first time was amazing, but I needed to rest my ass because it was sore."

"Okay," I relented. "If my hole feels okay, can we start doing it everyday?"

"If that's what you want, dude," Parker said.

"It is," I hissed. "I think I want to come out of the closet, too."

"To your folks?" Parker asked, and I gave him a sweet smile. "You'll feel better once you do."

"Do you want us to walk you home?" Ronnie offered, and I nodded with stars in my eyes.

With that, they both shared a kiss with me, then they kissed on the lips and smiled lovingly at each other before we got up. Ronnie held my hand while Parker carried my board, then they walked me home while my satisfied rear end hummed with pleasure and hot cum dripped into my undies.

🏳️‍🌈 The End 🏳️‍🌈

Feedback: jtstories@tutanota.com

Up Next -- Tyler returns to the Adult-Youth section of the archive in Tyler Mans the Glory Hole

Coming Soon: Troy's got a plump bubble butt and a craving for gay sex. But what happens when he finds himself living solo while his dad's in jail? Find out in Easy Access at Troy's Back Door 🏳️‍🌈

Available Right Now -- Read new Chapters of an old story. Casey's made his return to this section of the archive in The Party Never Stops 🏳️‍🌈

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