From Friends to Brothers - Chapter 5: Settling In

“Right, lay back. I think you’re on the edge of breaking your third rule for the day,” Samantha said, now standing at the end of the bed looking over Jacob.

I watched as he blushed as he quickly did as he was told. Samantha quickly grabbed his ankles, pulling him closer to the end of the bed as she let out a smirk. A movement that I was sure elicited a very particular reaction from Jacob, as I know it definitely would have gotten a particular reaction from me. She quickly unbuttoned his pants as I  turned to leave, heading into Samantha and I’s room to retrieve the changing supplies, knowing quite well what was happening.

I walked back in the room, diaper and powder in hand to see Jacob laying flat on his bed with a full erection as Samantha crumbled his clothes in a ball and threw them next to the closet. I couldn’t help but have a huge smile on my face as I handed Samantha the diaper. Something about seeing Jacob like this was actually kind of hot.

“Thank you, and can you grab your little black…” Samantha said, making a hand gesture that gave me all of the information I needed. “We have to wait for this little guy to deflate anyways,” Samantha said mockingly, looking back at Jacob who was trying his best to avoid eye contact.

“Sorry!” He said, pulling his arms up over his face in an attempt to hide his embarrassment.

“Mhmmm,” Samantha said softly. “I’m sure you are…”

I quickly returned with the chastity cage that I typically was forced to wear as a punishment, or if I was ever left on my own for extended periods of time, as well as a small bottle of lube that I knew would almost certainly be a requirement, especially for first time users like Jacob.

“Thank you, sweetie,” Samantha said, grabbing the items from me as Jacob continued to look away. It was weird how trusting he was of us. I would have almost certainly looked at what had been fetched in addition to the diaper, but it was pretty clear he was blissfully unaware of what would soon become his new reality.

“Alright, Jacob baby. This is gonna feel a little cold,” Samantha said, before squirting a big glob of lube onto the base of his flaccid penis.

I watched as she quickly worked it around the circumference before quickly lubing up the ring and sliding his privates through, just in time all of the motion had quickly made Jacob aroused again, which finally made him look.

“What is- oh…oh!” He said, which I took as him fully understanding what was happening.

“Samantha, I don’t uh-” Jacob started.

“Shhh baby, let Mommy take care of her baby boy,” Samantha cooed back.

Jacob laid back on the bed facing the ceiling. “Do I- do I have to wear that?” He said sheepishly.

His cock throbbed, only further pointing out the fact that he loved the idea. Samantha looked at me with a smirk.

“Yes, baby. All little boys need to wear one to keep them acting like good little babies. You want to be a good little baby for Mommy, don’t you?”

He nodded profusely as his cock throbbed. I could feel my own cock begin to harden just from watching. I could only imagine he was hoping for something a little special before having to wear the cage for the first time, as I know that I would be hoping she finished me off at least once beforehand.

“Alright baby, your gonna have to show Mommy what a good boy you are by making your little boy parts soft again,”

“But- but- maybe you could just-” Jacob started, feeling desperate for her touch.

“I’ll give you 30 seconds and then I’ll have to give you a naughty sticker. I don’t think you want to get any naughty stickers, do you baby?”

Jacob shook his head. “No, Mommy…”

I could see him hesitate, but he flexed his arms which as any guy knows is one of the fastest ways to get rid of boner, even if your body is telling you that you really want to have a boner, which was obviously the case for him currently.

“Good boy,” Samantha said, lubing up the cage and sliding his now limp cock inside before securing it and pocketing the key. She quickly slid the diaper underneath and powdered him up, closing the diaper up and helping him up off the bed.

“Good job, sweetie,” She said scuffing up his hair. “Now, your safe word is Jock Strap. Use it if your ever uncomfortable, or if the cage is causing a lot of pain. You should know that it's pretty normal to have a lot of discomfort for the first few days, but if it really hurts let me know. Though, if I can tell that you were just lying to get it off…”

Jacob nodded, as his face turned red.

“Perfect. Why don’t you boys get all of Jacob’s things unpacked, maybe just lay them out on the bed so I can quickly see what I am working with here and I’ll go wipe up some lunch for you boys,”

“Thanks Mommy,” I said, giving her a smile. Samantha smiled, stopping on her way out of the room to give me a very passionate kiss, something I figured was to tease Jacob more than anything. Which I could only imagine would be a running theme for a bit. “Oh, can I have some juice please?”

“Of course, dear,” She said, making her way out of the room.

“Um- me too?” Jacob said.

“Me too…” Samantha said, turning around in the hall.

“Please, Mommy?” Jacob said, now blushing.

“So…” I said, grabbing one of the bags off the ground and setting it on the bed.

“So, what?” Jacob said, following suit.

“How’s it going?”

Jacob let out a little laugh. “Better than I could have ever hoped for,” He said with a huge smile.

“Wow, really? Not what I would have expected from someone who just got put in a cage,”

Jacob shrugged. “Small price to pay?” He said with a smirk, obviously enjoying himself.

We emptied the contents of all of the bags onto the bed, spreading things out into piles. It really was just clothes and a few essentials.

“Boys…” Samantha said, entering the room again with two bottles of juice, setting them both on the dresser. “Good job!”

I circled around the bed, grabbing both the bottles and handing one to Jacob as Samantha peered over the contents on the bed.

“Mhmmm… What's in the boxes?” Samantha asked.

“Oh, just my computer stuff,” Jacob responded with some slight hesitation.

“Can you show me?”

Jacob did as instructed and opened up each of the boxes, revealing a rather simple setup with just his desktop and a monitor, as well as a few peripherals.

“And what's that down there?” She said, reaching down into the box and pulling out a brown stuffed rabbit.

“Oh…yea,” Jacob said as he blushed a little, obviously not having wanted her to see that.

“Does it have a name?” Samantha said, turning him around to get a good look at him.

“Not really…he’s just nice to have around…” Jacob said sheepishly.

“Are these cum stains?” Samantha said, rubbing her finger along the underside of the rabbit where there was some crusty fur.

Jacob’s face became a bright red as he couldn’t help but hide a smile.

“It's okay, baby. Nothing to be ashamed of,” Samantha cooed, ruffling Jacob’s hair as she handed him the stuffed rabbit. “Can you explain to Mommy why there are icky boy stains on your little stuffed rabbit?”

“I…hump…” Jacob whispered quietly.

“Yea? Does it feel good to rub against it?”

Jacob nodded.

“Wouldn’t your diapy catch all of your icky cum?”

“I…I’ve only ever bought diapers in this last year…” Jacob said. “I usually just stick him in my pants…”

I had to hide my giggle. It definitely wasn’t something I had thought of before, but I could imagine that the soft fur would actually probably feel really good.

Samantha smiled at Jacob. “Well, Mommy knows just how to reward you when you’ve been a good boy now,” She said, with a smirk.

She got up, making her way towards the door while Jacob remained where he was, awkwardly standing still. “You boys going to be okay here by yourself? Thinking I’m gonna make a Target run for some essentials, as well as a few things for Jacob’s room,”

Jacob, who was still red in the face nodded.

“Yup! We’ll try to get everything unpacked. What about lunch?” I said, taking a sip of my juice.

“I’ll pick something up on the way back. Should only be a few,” She said, grabbing her purse before heading out the front door.

I turned around to look at Jacob who was still holding his rabbit with a smile.

“I used to hump things all the time in my diapers, never thought about putting it in my pants though” I said, trying to sound sincere and break up the awkwardness.

“Yea, it's actually really nice. Better than when I tried it with a diaper on actually,”

“Dam, I’ll have to try that,” I said, which Jacob just responded to with a laugh. “So, everything is good than?” I asked.

“Yea, things are great. Honestly just want to get settled in”

“Of course. So I would assume humpy here goes in the bed?” I said teasingly, gently taking the rabbit as I tossed it into the bed.

Jacob couldn’t help but smile.

We made quick work of putting the rest of his things away, setting up his computer on the floor temporarily until we were able to get him a proper desk. I thought about offering some space on mine, but it wouldn’t have really made sense seeing as it way already just barely big enough for my own stuff.

“Right, so what should we do for the next couple of hours?” I asked.

“Couple of hours?” Jacob asked.

“Oh, yea. She makes it sound like its a quick run to Target, but there won’t be anything quick about it. Especially if she has a reason to buy new things,” I said with a laugh. “We can go play on my Switch?”

“Sure,” He said, following me out into the living room.

The next two hours flew by as we raced it out in Mario Kart, happily sucking down our juice as if nothing was different from when we usually gamed together. Even though clearly a lot had changed. Jacob sat on the couch in nothing but the diaper Samantha had put him in, practically leaning on me for support as he altered between his pacifier and bottle as we bantered back and forth about the game. Definitely a moment that gave me a warm and fuzzy feeling.

~~

“Jacob, sweetie,” Samantha called out, having walked back in the front door with a few different bags of groceries. “Look what I got,” She said, setting down the bags in the kitchen before handing him a sheet of paper.

“What's this?” He said, jumping up from the couch and shuffling over to her, revealing his slightly yellowed diaper as he grabbed it from her before.

“Target’s hiring. Why don’t you fill that out and we can drop it off tomorrow,” Samantha said, starting to unpack some of the bags in the kitchen.

“Oh, right,” He said, looking back down at it.

“Man, do I not miss retail,” I said jokingly as I gave Jacob a nudge from behind before heading into the kitchen to help unpack.

“Oh stop. It will be fun. Plus it's an excuse for me to go more often,” Samantha said with a laugh. “Oh, and there's two kids meals in the car, along with some other bags if you wouldn’t mind,” She said, already pulling out fresh packs of baby wipes and powder from one of the bags she was unloading.

“You might want to at least put a shirt on,” I said teasingly, looking back at Jacob who was still holding the job application. “Wouldn’t want anyone to know that you forgot how to use the toilet,”