16. Saber

Chapter 16

Saber

It was a difficult decision, but I decided to hold off on having sex with Freddy a little bit longer. Everything was happening so quickly, and although I felt like I was keeping his best interest top of mind, I worried I was being a little bit self-serving.

So I slowed things down.

We spent the rest of the weekend cuddling and playing and experimenting orally and with our fingers, but no condoms were required.

The work week went quickly. I finished the UI improvements Freddy had asked for and deployed it into a test environment that we invited a few customers to play with.

They were extremely excited to see the upgrades, and I finally understood how satisfying programming could be. Having a real and tangible impact in a person’s business or their day-to-day job was awesome.

I was actually making an impact, even in my first few weeks on the job. That made each day fly by.

That, and the gorgeous view from my desk.

I still caught Freddy peeking up at me dozens of times throughout the day, but he caught me just as often. Who knew love could be so all encompassing.

Yes, love . That was the only word I could use to describe how I felt for him. What had started out as intrigue and attraction grew so quickly that neither of us could’ve prepared ourselves for the impact of our connection.

We had lunch together every day and dinner together every night. I stayed at his place long enough to tuck him in and give him milk to fall asleep, and then I headed home alone.

I’d only lived by myself for a few months since graduating and it was already getting old. I loved it at first, but now I wanted a particularly sweet and nerdy roommate to be at my side as often as possible.

At least we had the weekend.

When Friday finally rolled around again, I was ready. I picked up all the supplies we could need for the weekend together, regardless of where things went.

But Freddy had his own surprise in store for me.

He and I had lots of discussions during the week about the Daddy/Little dynamic and what that looked like for different people. I tried to make it clear that we would find our right dynamic in time and there was no pressure for him to try to be something that didn’t feel natural to him.

But as the studious boy he was, he dove into research. I could sense that some things were more interesting than others, but when I walked into his apartment on Friday evening with ramen and dumplings from one of my favorite Japanese restaurants, Freddy was wearing a cropped T-shirt and a diaper.

A fucking diaper.

I almost creamed my pants right there in his doorway. “Fuck, baby, you look gorgeous.”

He smiled. “Do you like this, Daddy?”

That had also become our new norm. In private, Freddy mostly called me Daddy, and I couldn’t get enough of it. His research helped him understand more about age regression, and he not only embraced it but wanted to explore every aspect of it.

Hence the train-covered diaper he was showing off to me.

“I love it.” I dropped my bags and placed my hands on his hips, loving the soft cotton against his silky skin. I let my finger tease just along the waistband. “So much.”

He grinned and ran his hand along the front bulge. “Me too. It feels a little funny, but I’ve been hard the whole time, so I think I like it.”

“Now Daddy’s gonna be hard the whole time we have dinner.”

He moved his hand over to my crotch, palming my growing length. “We could have dinner later while we take care of this right here.” He dropped to his knees and began to unzip my pants.

Freddy had become well-skilled in the art of a blowjob and knew exactly how I liked to be touched. I could have stood there for the few minutes it would take for him to get me off and then proceed with dinner as planned, but his courage in initiating so many new things was a sign that he was ready.

A sign I wasn’t going to ignore.

“That feels so good, baby boy. If you keep going, Daddy’s gonna come down your throat.” I brushed the hair back from his forehead and gripped it so his eyes moved up to meet mine. “Or if you’re ready, I can come in your bottom.”

His eyes went wide, and he pulled away. “Really? You finally want to make love to me?”

“Baby.” I knew the intent of his words, but it still felt like a stab to my heart that he thought I didn’t want to. I lifted him by his shoulders until he was on his feet and then lifted him again so he was wrapped around my torso as I let my jeans drop around my ankles and stepped out of them. “Of course I want to make love to you. Every day for the rest of my life. Sometimes twice.” I winked and kissed the tip of his nose. “I was just waiting for you to be ready, and now I think you are.”

“I am ready, Daddy. I’ve even been practicing.”

I choked on the air in my mouth and almost dropped him as I walked to his bedroom. “Practicing? What does that mean?”

“I watched a video on stretching. At night, I’ve been using my fingers to stretch myself out, but it doesn’t last very long. Every time I try it, I’m tight again.”

I held back a chuckle and smiled into the crook of his neck. “Yeah, it doesn’t last very long. Daddy will take care of it for you. But I’m happy to hear that you understand there will be some pain involved.”

“Oh, I do. But…” He looked up at me. “I think it’s a good kind of pain. I’m hard during that too. And when I put in three fingers, I usually ejaculate quickly, so I think my body likes it.”

Fuck, this boy was going to kill me.

“Daddy will make sure you do.” I was wholly focused on making his first time as pleasurable and pain-free as possible. That meant lots of lube and lots of careful stretching…

I took my time, kissing him in all his ticklish places to distract him as I slipped in one and then two fingers, spreading copious amounts of gel to make sure there wasn’t any tearing or pain that he didn’t like. But as he mentioned, Freddy was hard and leaking precome the entire time I worked him open.

By the time he was squirming enough that I thought he’d come in my arms, I was also hard and ready to slide inside him.

“You ready for Daddy to be inside you?” I leaned over him and pushed his thighs apart with my knees as I reached for the condom. I’d put them on a hundred times before, but this time was different. My hands shook, and I dropped the packet twice trying to open it like it was my first time ever.

Moments later, I was lined up to his opening and kissing him again as I pressed inside. He was so tight and sensitive as I slowly entered his virgin hole. “Tell me if you need a break, baby boy.”

He dug his fingers into my shoulders as he gasped. “It’s good, Daddy. More.”

I trusted he knew his limits, so I pushed all the way in, giving him my full length and holding there until I was sure he was okay to keep going.

“I’m almost gonna ejaculate, Daddy. My body likes the burning too much.” He curled his back and rocked to get some movement.

“I’ve got you, baby.” I leaned up and started rocking, pushing against him as he writhed beneath me. “Hold on for as long as you can and then you can come, baby. Daddy is right there with you.”

I would have been able to hold on much longer, but Freddy spread his knees wide open so he could curl up and then his fingers closed on my nipples, spraying milk onto his face and chest.

“Fuck, baby.” Seeing drops of my milk covering him was too much. I threw my head back and came into the condom, releasing the tension that had been building between us for weeks. And when Freddy came too, squeezing my cock tight like it was wrapped in his fist, I felt another tremor deep in my gut. “I think I’m in love.”

He leaned forward and bit down on my nipple, drawing another squirt of milk into his mouth as my whole body shivered from the spike of pain from his teeth. “I know I’m in love, Daddy. And I want you to do that again.”

“I will, baby. I promise.” I pulled out and removed the condom then rolled us both over so Freddy was lying on top of me. “Every day for as long as you want me.”

“Forever.” He grabbed my ears and pulled me toward him. “I want you forever.”

“That sounds like an excellent plan.” I grinned. “But first…”

“What, Daddy? We already did the most important first. What else could there be?”

“Ramen and dumplings.” I reached for his plump ass and squeezed his cheeks. “Then let’s get that diaper back on you. You look so delicious in it.”

He nodded his head. “Okay, but you’re literally delicious. Can I have some milk before dinner?”

I scooted up and guided his head over my chest to my nipple. “You can have Daddy’s milk anytime you want. Drink up, baby boy. We have a busy weekend ahead of us.”

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