Chapter Text
I wasn’t really looking forward to this date. I’d only agreed because this chick I had fucked around with said she knew a great gal that she insisted on hooking me up with. As a divorced single guy of 35, I felt I shouldn’t look a gift horse in the mouth, even if I hate blind dates. But she showed me the gal’s picture, and she was cute with a nice rack, so I figured, why not?
I drove up to the house and got out of my Porsche, straightening my tie and making sure not to forget the bouquet of flowers I had bought to present her with. I know it’s a bit old-fashioned, but it goes a long way in convincing a broad to let you get in her panties. I made my way up the driveway to the kind of run-down house. I wasn’t sure if this neighborhood was the best place to leave my car unattended. After ringing the doorbell, I waited a moment before I heard a “Be right there!” from inside that didn’t exactly sound like the voice of a woman. After another beat or two, the door swung open to reveal not my date but a boy in a baseball tee, a matching cap, and basketball shorts.
“Hello?” I started. “I’m here to see Tawny. Do I have the right house?”
“Yep, that’s my mom. You must be her date. Do you want to come in?” he asked as he stepped aside and motioned me in. The kid was certainly very polite. I stepped through the door, and he motioned me into the living room.
“I’m sorry. I didn’t know that Tawny had children.”
“Yeah. There’s me and my little brother, Mason. But we don’t live here. We live with our dad. I was just visiting today, but my dad is running late picking me up. I wasn’t supposed to be here when you arrived. Sorry about that.”
“That’s okay. No problem here. I was just confused for a minute.”
“Gotcha. You can sit if you want,” he said, motioning to the sofa. “Do you want a beer?”
“A beer?”
“Yeah, a beer. Mom always has some in the fridge. I can get you one if you want.”
“Sure, why not?” I answered. I watched as the little guy left the living room, and he reappeared a minute later with a glass bottle already opened. Had to admit he was a cute kid. Still short but solidly built. Not chubby, though he still had a little baby fat in his cheeks, but just solid.
“Here you go,” he said as he handed me the beer.
“Thanks,” I said, taking a swig of the beer while I assessed him. “How old are you? You seem very polite and mature for a boy your age.”
“I’m 10. Gonna be 11 in two months. My dad says politeness is important in a boy. He’s proud of the way he’s trained me.”
Odd choice of words, I thought, but it didn’t pursue it. I sat back down on the sofa, and the kid sat at the other end.”
“What’s your name?”
“Jeremy. Sorry, I should have said it when I opened the door.”
“Nice to meet you, Jeremy. I’m Abe.” He gave me a bit of a cheeky grin. I took another sip of beer and then snuck a glance at my wristwatch. He caught me looking and was about to say something when I heard a woman call from upstairs.
“Jeremy! Was that my date at the door?”
“Yes, mom!” he yelled back.
“Great. Tell him I’ll be down in 10 minutes!”
“He can hear you!” he called, giving me the benefit of a little eye roll. Jeremy was growing on me. I wasn’t looking to date a woman with kids, but if I were, a kid like Jeremy would be pretty nice. He was chill in a way I didn’t think most 10-year-olds were.
“Don’t be smart! Did you offer him a drink?”
“Yes, Mom. He has a beer.”
I heard a door close and assumed she had gone back into her room to finish getting ready.
“Sorry about that,” he said.
“It’s fine. I don’t mind waiting another 10 minutes.”
“Yeah. About that. When mom says she’ll be ready in 10, that usually means at least 30 minutes. My mom is always late. Like really late. Dad says she’s going to be late to her own funeral.”
“I see.”
“My dad should be here soon. I think. He was picking my little brother up from our grandparents. Mom’s parents. They are always late, too. That’s probably why he’s running behind. I know you didn’t sign up to hang out with a kid tonight, so I can leave you alone if you want.”
“No, that’s fine. I like kids, and you seem pretty cool.”
“Really, thanks.” His face lit up a bit with the compliment.
“No problem.”
We settled back into the sofa and relaxed. I could see Jeremy stealing glances at me.
“Do I have something on my face?” I asked.
“No. Sorry. It’s just mom didn’t tell me you were so handsome.”
“Oh, well, thank you. I appreciate the compliment. You’re a good-looking kid, too.”
“She also didn’t say you were so tall. How tall are you?”
“6’4”. All the men in my family are tall. What did your mom tell you about me?”
“Nothing really. I just overheard her talking about you on the phone with Aunt Sarah.”
“Yes. Sarah is a friend of mine. I hope they were saying nice things.”
“They said you had a huge cock,” he said matter-of-factly. I nearly choked on my beer; I was so surprised.
“What?” I spat before catching my breath and then wiping my shirt off.
“Mom asked Aunt Sarah if you really had as big a cock as she had been told, and Aunt Sarah said yes.”
“That’s embarrassing. I’m sorry you had to hear that.”
“It was fine. I liked it. How big is it?”
“What? I’m not answering that.” I was firm in my voice, but I had to admit that a cute boy asking me about the size of my cock was turning me on a bit. I could feel my blood flowing to my crotch.
“Please? I know Dad says I’m too curious, but Mom made a big deal out of it, and I’ve been wondering all day.”
“Listen, kid. People kind of don’t like it when a man talks about the size of his cock with little boys they don’t know.”
“I’m not a little boy.”
His persistence was kind of hard to fight, and truthfully, his curiosity about my dick was a bit of a turn on. Besides, it’s not like I was flashing the kid.
“Ok. Ok. It’s 10 inches.”
“Fuck. That is big. That’s bigger than Dad’s.”
So many questions ran through my head.
“You know how big your dad’s cock is?”
“Yeah. Like I said, I’m not a little boy.”
“How big is your dad’s?” I shouldn’t be asking these questions. I know I shouldn’t, but the possibilities that this discussion was opening up were really starting to turn my crank.
“8.5 inches, or a little bigger when he’s really hard.”
“You’ve seen your dad’s cock hard?”
“I’m not a…”
“A little boy. I know, I know. Sorry. So, you’ve seen your dad’s hard cock? When?”
“All the time. Can I see yours?”
I couldn’t answer immediately. On the one hand, since I moved from the West Coast, I promised myself I wouldn’t do this again. I have too much to lose. But on the other hand, this conversation had me hard as fuck, and the idea of showing my cock off to this dirty boy was the hottest idea I’ve had in a long time.
“What about your mom? She’s right upstairs, and she’s going to be down in a couple of minutes.”
“I told you, she’s going to be at least another 30 minutes. She’s in her room with the door closed and her music blaring. She won’t come down.”
His reassurance made up my mind.
“Have you touched your dad’s hard cock?”
He looked at me like I had just asked him the stupidest question of all time. I shifted my position on the sofa so that my crotch was pointing in his direction.
“If you want to see it so badly, why don’t you pull it out?”
Jeremy’s smile lit up the entire room. Fuck he was a cute boy. He scooted closer to me and then reached out and undid my belt. He struggled with my top button for a moment, so I leaned back a little further to make it easier for him to get a better purchase and pop it open. He then slid my zipper down before pausing.
“Go ahead, take it out.”
He reached into my boxers and wrapped his small hand around my girthy shaft. I moaned at the touch. It had been too long since I had a boy handling my cock. He pulled it from its hiding place and gasped at the sight.
“Wow. That is so big!”
“You like it?”
He just nodded, his eyes devouring the entirety of the hog in front of him.
“Stroke it,” I told him, and he began to slowly, lovingly stroke the length of my shaft. This certainly wasn’t his first time doing this. His small tongue darted out and slicked his lips. He was a hungry boy.
“When did your dad teach you how to suck dick, boy?” I asked. I was going to ask if his dad had taught him to suck cock, but at this point, it seemed obvious to me what he meant when he said his dad had trained him.
“I don’t remember. It was a long time ago. Before mom and dad split up, and that was five years ago.”
Fuck, man. I was really starting to like Jeremy’s dad.
“Do you want to suck mine?”
He didn’t answer, he just leaned forward and licked my cockhead. I closed my eyes in ecstasy before quickly remembering we weren’t alone in the house and we were playing a very dangerous game. I needed to keep my wits about me. He gave the head a few more slow licks, dipping into my slit to get a taste of my dripping pre-cum. He then opened his mouth wide and started to work his way down my shaft. The wet, hot velvet of his mouth was spectacular. His pillowy lips were stretched to their limits as he slid his way halfway down my length. He paused to take a deep breath through his nose before he continued down the shaft. I felt my cockhead hit the back of his throat and then slip past it as he moved lower and lower on my cock. His dad must have trained the gag reflex out of the boy. I reached out and placed my hand on the back of his head as he made his way to my crotch, burying his nose in my pubes.
“Fuck, Jeremy. I need to send your dad a fruit basket. Fuck, boy, he taught you well.” I released my hold on his head as he worked his way back up my cock before coming off it, only to slap it against his face. My cock was bigger than his entire head.
“He’s really proud of how good I’ve gotten at it.”
“I bet he is. Put it back in your mouth.”
He proceeded to worship my cock for the next five minutes, giving me one of the best blow jobs I’ve ever experienced in my life. I think I was falling in love with this boy. Smart, funny, cute, and Olympic-level head. I could feel my load building in my balls, but I didn’t want to blast just yet. I tapped his head to get his attention and have him back off.
“Does your dad let other men fuck you?”
“Yes. He says I can pick who I want since I’ve got a good head on my shoulders.”
“Would you let me fuck you?”
“Yes, please!”
“Have you taken one this size before?”
“I’m not a little…”
“Turn around and bend over.”
He did what he was told, and I was presented with the hottest, tight pink hole, just ready to be violated. I dove in, pushing my tongue into his hole. Jeremy moaned as I devoured his ass like I was starving. I got his hole sloppy with my spit before I pulled back, replacing my tongue with my finger. It slid in like a knife through warm butter. I pulled back and added another digit, fucking his hole as he mewled with pleasure. Two fingers became three, and then four. His hole was tight, but it had clearly been trained to take man-sized cock. I hawked up a good wad of spit to lube my tube steak and then pressed my head against his pucker.
“I’m going to fuck you now, Jeremy. You’re so fucking hot, boy.”
“Fuck me, Abe. I like it hard.”
“Let’s just get it in and make sure you are ok before I start pounding you.” I pushed, and his hole gave way easily, stretching to accommodate my massive size, but also clinging tightly to give me as much pleasure as possible. Fuck, it had been years since I had my cock in a hole so tight.
“I’m good, Abe. You can go now.”
“Give me a moment. If I move right now, I’m going to paint your guts immediately. I want to savor this.” I took a few deep breaths to settle my balls before I started slowly deep dicking the boy’s hole. I began to pick up speed, making sure to give a thrust as I bottomed out to slam into Jeremy like he wanted. He started panting as he encouraged me to go faster and harder. I could tell that I was building to climax, and I wanted to look into his eyes when I bred him with my load. I reached under him and then lifted him as I leaned back into a sitting position, twisting him around on my cock so that he was facing me. I raised him up and then slammed him back down on my cock. Jeremy’s eyes were rolled back in his head as I fucked into him. I hugged him to me as my load built. I looked up and caught sight of a person standing in the doorway and froze for a moment before I realized that it wasn’t Jeremy’s mom.
Instead, a tall, good-looking man stood there. Where I thought I would see anger in his eyes, there was lust. It must have been Jeremy’s dad. The very man who had taught his own son to take cock like a champ and had given him permission to fuck any man he wanted. My eyes scanned down his body, only to discover that his cock was out of his pants and was being sucked on by a small boy, clearly a handful of years younger than his big brother. My eyes traveled back until they locked with Jeremy’s dad’s eyes. I stared into them as I slammed his young boy onto my crotch a few more times before I began to blast his son’s insides with my cum. Though I had been as quiet as I could be up until then, I heard a roar escape my throat as jet after jet of my load left my body and went into Jeremy’s hole.
Once my orgasm subsided, I went limp as I attempted to catch my breath.
“He’s a hot fuck, isn’t he?” Jeremy’s dad asked.
“He certainly is. I assume you’re the one who trained him to be such a good boy.”
“That’s me. Jay. You are?”
“Abe. I’m here to take out Tawny, but your boy here caught my attention instead.”
“Yeah, she’s still upstairs.”
“Is that Mason?” I asked, nodding to the young boy who was still nursing on his dad’s cock.
“Yep, this is my little cocksucker. Holy Hell! I see why Jeremy went wild for you.” Jay was staring at my cock as Jeremy slid off and turned to his dad.
“Dad!”
“Hey, bud. Sorry, I’m late. You know how slow your grandparents are. I see you found something to keep you busy while you waited.”
“Dad, Abe was so good. He fucked me just the way I like it.”
“I’m glad to hear it.” He looked back at me. “Is this your first time with a boy?”
“No,” I said as I began to rearrange my clothes to their previous state, tucking my cock back into my pants. I reached down to pick up Jeremy’s shorts from the floor and tossed them to him. “My ex-wife’s brother had a boy, and we worked him over on the regular. Unfortunately, once I got a divorce, I lost access to the boy, too.”
“Shit luck, man. Listen, Tawny is still going to be a while, and I can tell you for a fact, she won’t put out any time soon. She’s also a boring lay. I was just going to take the boys home and have a little family fun. How about you ditch Tawny and come with us? I’d love to watch Mason here take a ride on that hog, if you’re up for it.”
“Fuck, man, really? That would be great. But she knows I’m here already, it would be rude to just leave.”
Jay looked at me with the same “how dumb are you?” look Jeremy had given me earlier.
“Like it’s not rude that she’s kept you waiting this long? Besides, your choices are to go on a boring date with no sex or come with us and spend the night buried balls deep in boy-hole. What do you think, Jeremy?” he asked, turning to his son. “Do you think Mason would like to get a chance on Abe’s cock?”
“Absolutely. He might not be able to take it all like me, but it will be good practice for him.”
“So?” he asked as he took his dick out of Mason’s mouth and placed it back in his pants.
Fuck this date. Sarah was going to kill me when she finds out I ditched her friend, but then fucking a boy’s hole had suddenly become a lot more important to me than a friendship with a past hook-up.
“I’m right behind you,” I said as I stood and followed Jay and the boys out.
“Dad,” Jeremy asked. “Can I ride with Abe?”
“I think you already did, bud.”