Best Babysitter Ever, 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 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.

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On Friday afternoon at 4 o'clock it was chilly outside, but Jacob had his arm around me. His body heat was keeping me warm as we sat on his back porch and talked about what we wanted to do. We'd just come from my house, where my mom, dad and little brother were already home and making it hard for us to have privacy.

It's not that I didn't want them to know about Jacob and me -- they already know I like him -- it's just that they don't seem to understand that I want to be left alone with him. Even though I'm only 12, we're free to makeout on my bed. But if my mom needs something from me, she'll knock on my door and interrupt without thinking twice. If my dad wants to show me something on his phone, he'll open my bedroom door without knocking, then realize he walked in on us kissing and apologize before closing the door. My little brother Kenny doesn't seem to understand that we don't want him in my room when we're trying to cuddle, or if we need to, well, you know...

We originally walked to my house after school so we could have a little bit of fun in my room. But the house was loud and boisterous as soon as we walked through the front door. Dad was using his drill in the kitchen and Kenny was running around the house making fart noises with his armpit. My mom was calling after him to settle down, which only added to the chaos.

So instead of going to my room to get frisky, I ditched my backpack and asked Jacob to lube me up. I slid my school pants down and he fingered vaseline into my hole while I moaned with bliss, then we shared a kiss and I pulled my pants up.

"Mom, we're going to Jacob's house," I called out on my way down the stairs.

"Are his mom and dad home from work?" she asked knowingly from the couch in the family room, and I rolled my eyes.

"No, but his brother's home," I assured her as we reached the bottom of the staircase.

"Is he in charge?" she asked guardedly, then she smiled warmly when she saw that Jacob and I were holding hands.

"Yes Mrs. Stevenson," Jacob answered for me. "He watches me after school."

"How old is he?" mom asked, and I sighed impatiently, earning me a look of dismay from her while Jacob politely answered.

"He's 16, ma'am," he told her. "He'll be 17 in two weeks."

This seemed to sate her, because her dismayed expression softened and she sat back in her seat.

"You'll be home in time for supper?" she asked me.

"I promise, mom," I swore, then she nodded her approval.

"That's fine, Tommy," she said. "Make sure you behave."

"I promise," I said with a sweet smile of my own, then we beat a hasty path out the front door before Kenny could ask to tag along.

Jacob held my hand while we strolled to his house. It's only a five minute walk, but it feels like the most special five minutes of my life when he holds my hand. His mom and dad weren't going to be home for a few more hours and it was relatively easy for us to stay out of his big brother's way. Jacob likes to joke that his big brother is the "Worst. Babysitter. Ever" because he barely pays any attention to him when their parents are gone.

When we got to his house we went through the side gate and took a seat on the back porch so we could share a kiss. His tongue slipped into my mouth and I moaned submissively, then the back door opened and his brother Rodney sarcastically quipped, "Get a room, you two!"

"Ha. Ha," Jacob replied with a sarcastic smile while I rested my head on his shoulder and cast my dreamy gaze up at Rodney. He's really cute, and I've been wanting to put out for him for a while. Me and Jacob have been hooking up for the past couple of months and I've had my eye on his brother the whole time. Every time I see him, my ass gets hungry. I know he's into guys, but I've never picked up a signal from him that he might be interested in hooking up.

Rodney reached down and ruffled Jacob's hair with a smile, then he said, "I've got the guys over to hang out. Don't say anything if mom or dad call."

With that, he closed the door and we locked lips again. As our tongues danced, I could feel the desire in my rear end starting to swell and needed to get laid. We broke our kiss and Jacob said, "Let's go to my room."

"Okay!" I agreed, then we stood up and he put his arm around my waist. When we walked through the family room, I couldn't help but scan the scene. Rodney had three friends over, and they were all really hot! I wondered if they were planning to mess around in the living room, or if they'd go to Rodney's room. I was hoping they'd stay where they were and maybe Jacob and I could join them. I found myself ogling all of their crotches while Jacob held me close, then his brother snapped me out of my spell.

"Hey turd, what are you gonna do, fuck your boyfriend?" Rodney asked Jacob with a snide grin while the other guys chuckled knowingly.

"You're just jealous because you're not getting any of this," Jacob shot back, then he gave my rear end a squeeze and kissed me on the lips.

I bit my lower lip and inhaled deep, taking in the bevy of hunks that were watching us, then I smiled suggestively and engaged my 8^th grade stud with another kiss. I added a little tongue for show, then I rolled my horny rear end around while Jacob squeezed it with both hands. When our tongues disengaged, we smiled at each other, then at Rodney and his friends. I moaned softly, then Jacob grabbed my hand and we hurried down the hall so we could get naked and fuck.

As soon as my beau closed the door, our pants came off and we locked lips again. My head was swimming with gay romance as he eased me onto my back and shuffled to get between my opened legs without breaking our kiss. When I felt his stiff boyhood poking me in the taint, I picked my legs up and wrapped them around his waist.

As soon as I had my ankles locked around my stud, his dick slipped into my ass and I moaned into his mouth. It felt so good to have him inside me, and I wanted him to know it. So I used my legs to pull him tighter to me, then we broke our kiss and smiled into each other's eyes.

"You feel so tight," he complimented me while I gazed up at him from the pillow.

"You feel so big in me," I panted. "I'm so happy you wanted to make love."

"Me too," he agreed, then he started thrusting and my body started to sizzle with pleasure. I moaned shamelessly, knowing that I was being treated to a 5 star lay in Jacob's bed. He leaned down and spoiled me with another kiss while my legs rocked back and forth around his hips. My whole body was on fire and I was racing towards my ultimate ecstasy with every thrust of cock Jacob fed me. I could feel my tummy rolling and my chest heaving up and down while his tongue stirred in my mouth, and I knew what was about to happen.

When we broke our kiss, I turned my head to his window just in time to lock eyes with Rodney and his three stud friends. They all looked mesmerized by the scene, and more than a little turned on. Instead of ratting them out to Jacob, I batted my eyes at them, then engaged my 13 year old stud in another French kiss while they watched with wanton expressions.

When Jacob buried his fuck stick up my conquered hole and seeded it, I was overcome with pleasure and desire. Our tongues were still dancing, but I managed to cast my eyes over to the window, where Rodney and his cute buddies were still watching. Knowing that I was being bred in front of an audience of hot studs added to my bliss, and my body responded in kind. My rear end, which was being pumped full of hot seed, clamped down around Jacob's big boy cock and milked it for more.

When my seeding was finished, Jacob broke our kiss and we smiled dreamily at each other.

"You were amazing," I sang with a satisfied sigh.

"You were too, honey," he told me, and I felt my heart race. "Sorry about my brother and his loser friends spying on us."

"You saw that?" I asked, a little surprised, and he rolled his eyes.

"Yeah, but I didn't want to quit fucking you," he admitted, then we both looked over to the window and saw that our audience was gone.

"I'm glad you didn't stop," I told him with a smile.

"Me too," he panted, then I felt his hard dick flex in my hole.

"They're really cute," I said, and he nodded in agreement. "But not as cute as you."

"Thanks, Tommy," he cooed with a dreamy smile. "I think you're cuter than all of them, too."

"Do you think any of them are cute?" I asked, and he nodded.

"I think all the guys my brother brings over are cute," he admitted with a shy inflection. "I think a few of them want to fuck me."

"You're lucky," I lamented, and he smiled warmly. Then with a hopeful smile, I asked, "Do you think they'd want to fuck me too?"

"Do you want me to ask?" he offered, and I felt a rush of excitement that made my face perk up into a grin. Without waiting for me to answer, he said, "Okay, I'll go check."

"I want you to fuck me again, too," I said with a shy smile, earning me a kiss on the lips. When our lips parted, I added, "I want you to go first, and I want you to go again after everyone else goes."

"I promise," he said, then he pulled out of me and I quickly sat up so I could suck him clean.

He put his undies on and walked out of his room while I laid in the bed and listened. I couldn't believe how easy it was for him to ask.

"Tommy thinks you guys are all really cute," Jacob blurted out. "He wants to know if any of you want to go all the way with him."

"For real, munchkin?" I heard Rodney ask.

"Yeah," I heard Jacob say, then I heard them talking amongst themselves for a few moments.

"There's more room out here," I heard one of the guys say, then everyone agreed with him.

Finally, Jacob announced, "I'll go get him."

All eyes were on my exposed, rock hard boy rod when my little stud ushered me into the living room. I was panting with need as I scanned the four hunks in my midst, knowing that I was about to have my ass fucked by all of them. While I was staring at my prospective tops, Jacob kissed me on the cheek and I smiled. He slipped me some tongue while the older guys watched, then I felt his fingers parting my ass cheeks so he could show my hungry, cum filled hole off to the room. I gave my hips a slow stir while he splayed my crevice for the room, then he pressed his middle finger up to my back door and I moaned.

Jacob broke our kiss and slipped his finger up my ass, making me moan a little louder while everyone watched. I saw that all four of my studs had taken their dicks out of their pants and were stroking them while they took in the show.

"Fuck he wants it bad," I heard Rodney exclaim, and I nodded to let him know he was right.

I rested my head on Jacob's shoulder and enjoyed the finger fuck he was treating me to while I surveyed the cocks I was about to enjoy. They all looked really big to me! The skinniest cock was also the longest. It looked like it was right around 6 ½ inches, and it belonged to a cutie named Jack, a 17 year old stud I'd seen before. He had dark curls and a sweet smile. There was a smattering of acne across his forehead, but I only noticed it because the light from overhead was shining down just right.

Sitting beside him was a hot 15 year old named Lucas. His dick looked like it was just a little bit under six inches, but it was nice and thick. I loved how his pubes shot out in all directions from the base, and how his smooth balls seemed to protrude through his sack. He had short brown hair and a little boy's smile. He almost looked like he belonged in middle school with me and Jacob. When he smiled at me, I felt my rear end contract hard around Jacob's digit.

Sitting on the floor was a hot twink named Richard. He's the same age as Rodney, 16, and his smile is framed by braces that make me blush. His dick was just a little bit smaller than Jack's, and standing straight up. He had kicked his shoes and pants all the way off, and his boxer briefs were hanging off his right ankle. His blond hair was parted on the side and his sideburns were trimmed perfectly. He was grinning from ear to ear while he watched Jacob fingerbang me, and I was feeling an urgent desire to ride his stallion.

Rodney was sitting on the couch right beside Lucas. His dick was the thickest of all, and looked like it was right around 6 inches. It also looked really juicy! I desperately wanted to start sucking it for him -- not just right there, but everyday from that point forward. Hopefully while his brother Jacob was stroking out my horny back door.

"Kiss me again," Jacob told me, snapping me out of my hypnotized state.

I smiled and puckered up, and before I knew it, our tongues were dancing while the older studs hissed and cussed. While I was being kissed up, Jacob pulled his finger from my ass and began easing me down to the floor. I couldn't believe how easily he was controlling my body, taking me to my back like it was nothing while he maintained our kiss. From the couch I heard Lucas say, "You're baby brother's such a stud."

"No shit," I heard Richard agree just as my head gently came to rest on the carpet, then Jacob picked my legs up and put them where he wanted them. His tongue was swirling in my mouth with unchecked power when I felt his glans press into my pucker, then he entered me again and I moaned like a girl.

And just like that, I was back in the throes of gay ecstasy.

Jacob fucked me for three glorious minutes while the others watched and played with themselves. When he broke our kiss, I looked over to the couch and saw that Rodney was locked in a deep kiss with Lucas. Their tongues were sliding in and out of each others' mouths and they looked like they were in love. Rodney had his hands on Lucas' cheeks and they had their eyes trained on us. To their left, Jack was stroking his cock and on the floor, Richard was doing the same. When Jacob buried his big boy cock up my butt and bred me again, Rodney and Lucas broke their kiss and my lover gently pulled out of me.

I quickly moved to get on my hands and knees so I could suck my 13 year old beau clean while I rolled my ass around in a clockwise circle to invite the next cock. Much to my delight, Rodney mounted me and my hungry bubble butt swallowed his girthy cock right away. I heard him hiss through clenched teeth, then he started thrusting and I was back in heaven. My ass was squeezing his prick so hard that he came in under a minute. While he was unloading up my ass, I could feel his cock throbbing and jerking inside me. I pulled off of Jacob's prick with a loud slurp, then I smiled over my shoulder at my 16 year old stud while he steadied himself.

When his orgasm was complete, he pulled out and I eagerly wrapped my lips around his dick to suck him clean. While I was moaning like a whore around Rodney's pleasure stick, I let my hips sway from side to side to send the message that I wanted another cock in me. Out of the corner of my eye I watched Jack get up from the couch and kneel behind me, then he positioned my hips while my little body burned with anticipation. I felt his long prick slide through my entrance and run all the way up my butt, then his pubes smashed into my crevice and I knew I had all of him. He tightened his grip on my hips and started thrusting, and I felt my body erupt with anal ecstasy. While my head was spinning with sheer delight, Rodney eased me off of his prick and caressed my cheek.

Stroke after deep, delicious stroke carried me into a haze of carnal delectation while my horny hole experienced contractions at an accelerated pace. Finally, the squeezing and gripping of my ass around his cock sent Jack over the edge. He bred me with a loud groan while I moaned and rolled my ass around, grinding it on his pole. When he pulled out of me, I watched over my shoulder with tortured eyes as he sat back on his legs and tried to catch his breath. His dick was still rock hard and I wanted it back in my ass, but before I could communicate my desires, Richard approached me.

With a new cock presented for my rear end's pleasure, I quickly re-assumed the position by planting my hands on the carpet and raising my ass up in the air. He used his fingertips to stroke the outside of my cum sopped hole, then he grabbed my hips and slid his dick up my ass. I shut my eyes and luxuriated in his thickness and length, loving how even after all the action I'd had, his dick was spreading me open as it sank in my welcoming boy hole.

As soon as he was buried up my ass, he began to thrust and I felt my body starting to catch fire. He fed me about 15 strokes that felt incredible, then he threw his head back and buried his rod up my ass. I let out a feminine moan as he seeded my cum tube, then his mouth dropped open and his braces glistened from the light overhead while I glowed with satisfaction. When he pulled out, Jack engaged him in a French kiss while I stayed where I was and waited to be mounted again.

Finally, Lucas approached me with a nervous expression on his face. I watched with a needy gaze as Jacob knelt beside him and rubbed his back, then he said, "Just push it in. It feels really good."

Lucas smiled cutely at my 13 year old beau, then he put the head of his dick up to my hole and pressed forward with his hips. The head slipped away from my anus and his boner sprang up, so Jacob wrapped his hand around it and guided it to my entrance. While he held it in place, he gently told Lucas, "Now push."
And just like that, I had the 15 year old's cock in my hungry, needy ass. He buried it all the way up my ass in no time, and while he was resting, Jacob kissed him on the lips. When they broke their kiss, Lucas pulled back, then pushed forward and moaned, then he froze and a frantic look flashed across his face. A split second later, I felt his dick throb and I knew he was unloading in my ass. I moaned and rolled my hips around to let him know how happy I was that he nutted in me, then Jacob told him, "You can stay inside and go again if you want."

I nodded in agreement while Lucas looked around with unsure eyes.

"Give him a kiss," I heard Rodney tell Jacob from the couch, then I watched as my 13 year old stud engaged Lucas in a deep, tongue filled kiss while his dick throbbed in my ass.

When they broke their lip lock, Lucas rested his hands on my hips and slowly started to thrust. Before I knew it, I was moaning like a little girl while my body shivered. He nutted fast again, then he pulled out and Jacob kept his promise by mounting me. With my ass pointing straight up behind me, he took charge and fucked me silly while my knees burned from the friction on the carpet. When he threw his head back and came for the final time, I smiled over my shoulder at him with starry eyes.

He pulled out and I got to work, sucking him clean while the rest of my tops relaxed in a heap on the couch. When I finally released his dick, I snuggled in his arms in the middle of the living room floor. He held my shivering body close and engaged me in a final kiss while my satisfied rump oozed with cum.

🏳️‍🌈 The End. 🏳️‍🌈

What happens when Seth discovers his family's darkest secret? What about his own secrets? Find out right now in It's A Family Affair 🏳️‍🌈

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