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Story: Dirty Daddies Pride 2025 (Dirty Daddies Anthologies #7)
Chapter Eight
Ethan
The backpack was still empty as I debated whether or not to take it. Beside it were a pair of pajamas, my stuffed giraffe, and my pacifier. All the things I’d want with me if I stayed overnight… but that was a bit presumptuous.
He invited me over for dinner, not breakfast.
And it was only our second date.
Granted, things had escalated quickly and unexpectedly after our first date. Packing a bag was still a bit much. Then again, if things went well and he did invite me to stay, I didn’t want to have any reason not to.
If things didn't go well, I still wanted to be upfront about my Little side from the beginning. He might not be into a boy who age regressed. I didn’t go too Little, but I did like baby things, sometimes.
Mostly the pacifier. And I’d be happy to suck anything as I fell asleep. A thumb. A cock. I wasn’t picky.
It was finally time to find out. And if he really did want to put my needs first, he would be my Daddy no matter what my bedtime routine consisted of.
When I was finally ready to head to his place, I grabbed my phone and sent James a quick text.
Coming over now.
Then I added xx to hint that I was ready for more of the kissing and other stuff. Whatever that happened to be.
James was waiting outside my building when I stepped outside. He pulled me into his arms and kissed my cheek. “I’m so happy to see you, sweetheart.” He took the backpack off my shoulder. “Let me carry this for you.”
My jaw was tight as I braced myself for questions about the backpack, but they never came. “Thank you. I didn’t expect you to be waiting for me out here.” I took the opportunity to give him a quick peck on the cheek.
“Didn’t want to risk you changing your mind at the last minute. Besides, I’ve been waiting forever for you to come over.”
Forever? It was exactly three minutes later than when he expected me to head out. “Hmm. Let me see.” I tapped my chin and pretended to think about it. “It took me ten seconds to pack an overnight bag, ten seconds to put on shoes...”
“Overnight bag?” James raised his eyebrows. “I like the sound of that.”
We walked across the street toward his building.
“I don’t mind carrying my bag.” It wasn’t heavy, but it was heavier than not having a bag at all, which was what a normal person would bring on a second date.
“Daddies carry the luggage.” He side-eyed me. “Right?”
I laughed at his silliness. “I wouldn’t know from experience, but it’s a very sweet gesture, so probably yes.”
“Okay, then.” He punched the key code into his building and the door lock released. “It’s settled. When I’m with you, I’ll do the heavy lifting. Are you comfortable with that?”
“Am I comfortable with you carrying stuff and doing the manual labor? Uh, yeah. It’s all yours, Daddy.” I held my breath, willing myself not to apologize for calling him that. I wasn’t sorry, and I wanted him to be comfortable with it.
Up in his apartment, I pretended to look around, but mostly I was nervous for what was about to happen. Excited but nervous. “Wow. This place is amazing!” I headed for the window and stared out at my own apartment, one floor down.
“Yeah, but I should warn you that the guy across the street likes to walk around naked in his place.”
For a second, I thought he was talking about someone else. But when I glanced at him, he was grinning. “Hey, I don’t do that all the time. Last night was… an accident.”
“That's not how I remember it.” Daddy set the table and then pulled something out of the oven. “And for the record, I’m not complaining.”
That’s what I thought. “So, what are you making me, Daddy?”
He dipped a spoon into the red sauce and tasted it. “It's a surprise.”
Whatever it was sure smelled good. “A pasta surprise? My favorite.”
“Mine too,” he said. “Now what would you like to drink?”
I was a little thirsty. “What are my choices?”
He opened the fridge and peeked over the door. “Milk. Apple juice. Ginger ale. Beer. Hard cider. What sounds good?”
“May I try the cider?” I didn’t drink often, but I felt safe enough with James to loosen up. Besides, if things went well, maybe I’d need to be a little looser later on.
“Sure thing.” He pulled out a bottle and twisted off the cap for me. “Have a seat and get comfortable. Dinner will be ready in a few minutes.”
With my drink in hand, I dropped down onto a dining chair and watched him work. He moved with confidence. Slicing up garlic bread, pouring sauce over noodles, sauteing chicken, and then tossing croutons onto the salad like an iron chef.
Was there such a thing as a chef kink? If so, I was into it.
Once we were both seated and had our food in front of us, I was instantly taken back in time. James used to cook for us all the time. Pancakes for breakfast. Pizzas for lunch. And spaghetti for dinner.
Such a good Daddy.
I eyed my plate like it was a five-star meal. Maybe six. No, seven! The pasta was covered in chunks of grilled chicken, not breaded like nuggets but sautéed like grown-up food. “Asparagus is my favorite veggie.”
“I remember.”
I jerked my head up and he was staring right at me. “You remember that little detail about me?”
“I don’t remember everything, but I do remember that.” He smiled and then lifted his beer toward me. “Let’s toast to new beginnings.”
“Cheers.” I tapped my bottle against his then took a drink before digging into his delicious meal. It was cheesy and well-seasoned without being spicy, and the chicken was exactly how I liked it. Seared around the outside but moist and tender on the inside.
“This is so good.” I scooped another load into my mouth and chewed it up. “I could eat this every night.”
“You can.” James grinned as he put a piece of garlic bread in his mouth. “I’d love to feed it to you every night.”
My shoulders dropped, and I felt a little frustrated.
Before I could reconsider, I put my fork down and sighed.
“I haven’t done this before, so it’s hard for me to tell when you’re just saying something to be funny or real.
Like, that sounded like a joke, but my heart wants it to be real.
” I swallowed hard and tried to convey what I was feeling with as few words as possible.
“Please don’t pretend. Don’t say it if you don’t mean it.
And if you’re teasing, please tell me when it’s just a joke. ”
James’s face fell, and he looked stricken. I’d hurt him. Fuck .
“Sweetheart.” He came around the table and crouched in front of me so we were at eye level.
“I’m joking in the sense that it’s an unreasonable thing to say after just reconnecting with you.
But it’s true in the sense that I can’t stop thinking about you, and I truly would love taking care of you. Every damn day.”
My face burned under his intense gaze. If he meant that, did that mean… I took a deep breath before making eye contact again. “I really like you, James. Daddy. Like, maybe it’s even love.”
“I know what you mean, sweetheart. I get it. And I’d really love for you to stay the night.”
I wanted to scream yes at the top of my lungs. Instead, I gave him a silly smile and whispered, “I’d like that.”
We topped the meal off with a couple scoops of Chunky Monkey ice cream on his sofa. We shared a bowl, and when I didn’t reach for a spoon, Daddy fed me from his. My cock didn’t soften for a second.
And when we were done, he put the bowl on the table and pulled me into his arms with a kiss. He moved slowly, teasing my mouth with his probing tongue until I was crawling over him to get closer. His mouth was sweet from the chocolate and banana, and I couldn’t get enough.
“I want more, Daddy.” I pressed my cock against his, making sure he knew exactly what I was talking about.
“Not yet, baby.” James ran his hands down my back and then under my ass, lifting me an inch so there was less pressure on both of us.
“It’s a big step. I want you to be ready.
” He pressed his nose into the crook of my neck and then dragged it down to my armpit.
“Because once I get my hands on you, I won’t ever want to let you go. ”
There he goes again. Making promises.
I slid off his lap and let him wrap an arm around me like a warm blanket. “I won’t ever want to go. I’m ready.” I sighed and picked at the hem of his shirt. “I don’t want to be a virgin anymore. And I want you to be the one to take it. I want you to be my first and only.”
His arm pulled me even tighter to his side. “I want that too. But we don’t have to rush.”
Anxious to spur things along, I twisted so my back was against his chest and I pulled my cock out. “Fine, then I’ll do it myself.” My fist closed around my dick and started stroking. I’d been hard for so long that I was already close. “Since you don’t want to help me.”
“Fuck, boy.”
As if finally giving in, he stood up with me in his arms. He carried me to the bedroom and pulled the drapes shut so no one from my building could see in. No one could witness this first we were about to share.
This moment was just for us.
Daddy took his time undressing me and then himself before kissing up the inside of my thigh.
My body was on fire, and the simple act of breathing felt like it took too much concentration away from the places where his fingers and tongue and cheek rubbed against me.
He pulled a clear box out of his nightstand, and I saw a few condom packets as well as a tube of lube. There was also a pack of tissues and a small towel tucked inside. Had he planned that for tonight or was he always prepared to bring someone to his bed?
It didn’t matter either way. He was with me tonight, and that’s what I focused on as his slick fingers finally pressed over my hole and teased inside me.
Daddy moved slowly as he entered me, distracting me with kisses and encouraging words until I was loose enough to take more than just a few fingers. “Please, Daddy.” I squirmed beneath him, trying to quench the desire I couldn’t quite reach on my own. “I need you.”
His teeth closed over my earlobe and he slowly pulled off. “You sure you're ready, baby? It’s gonna hurt.”
I tentatively reached for his cock, stopping just before I made contact and looking at him for approval. “Can I?”
He nodded and swallowed hard as my thumb and forefinger wrapped around his girth and felt the weight of his heavy shaft.
“It’s so big.” I slowly stroked down to the base and gave his balls a tickle. “Will it fit?”
Daddy smiled through a full-body shudder. “It will, but you’re so tight right now, it’s gonna hurt at first. But after a while, you’ll fully stretch around me.”
“I’m ready for it, Daddy. I promise to be brave.” I pulled my fist back up and ran my fingertip over his slit the way I liked to do on myself.
“I don’t want you to be brave, sweetheart.
” He kissed my chin and then started moving down my torso, dropping wet kisses along my skin until he was kissing the head of my cock.
“I want you to be honest. Tell me how it feels, when you need a break, and when you’re ready to come. That’s what I need from you.”
I nodded, willing to agree to anything as long as it meant more of him inside me.
Daddy took his time with everything. Putting on a condom and then coating himself and me with more lube. It felt so perfect as he finally pressed his dick against my opening and breached me. The sensation of being too full was instant. Had anyone ever burst from their first time?
Then I thought about all the videos and articles I’d read about anal sex and knew to breathe through the pain, bearing down on his length until I could feel his heavy balls against my skin.
It might have been seconds or minutes, I wasn’t focused on time, but eventually, I exhaled and all the tension in my body went with my breath. I fully relaxed and pulled my knees up tighter to my chest. “I’m good, Daddy. You can start moving.”
He didn’t need to be told twice. Daddy pulled out a few inches and then pushed back in, repeating that action until he was pulling almost fully out and slamming back in with toe-curling force.
The friction was different now, no longer all-encompassing but a mix of pain and pleasure that quickly took me to the edge of a climax. “More!” I gasped. “Please, don't stop. I’m gonna…”
I rocked against him, so lost and so close that I wanted to scream. And then I was screaming. Begging. Praising.
“You’re doing so good.” James took a ragged breath and ran his hand through my hair. “Come for me, baby.”
“Yes, Daddy!” An explosion of sensations went up and down my spine as I came hard, coating my belly in cream as I rode out the vibrations.
He grunted and pushed in deeper until he was a tight wire of muscles. Daddy came with his eyes shut tight and his cock pulsing inside me.
We were quiet for a moment, and it wasn’t until Daddy was wiping tears from my eyes that I realized they were there.
“Are you okay, baby? Did I hurt you?”
I shook my head and smiled, not entirely sure why I was crying, but I knew they were good tears. “No, Daddy. I think you… fixed me.”
Table of Contents
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- Page 19 (Reading here)
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