From Friends to Brothers - Chapter 2: A day of uncertainty

I logged onto Minecraft, joining the server that some of us played on to find Jacob was online.

“Hey,” I messaged on Discord, a usual routine for when one of us saw the other was online. But I didn’t get the usual response. Minutes went by and still nothing, so I went looking for him in the world. Maybe he was afk?

“Hey,” I messaged in the chat upon finding him, actively working on one of his projects.

“o/” He responded in chat, to indicate a person waving back.

It was at this point that I realized Mommy had been right. We both weren’t just going to forget what had happened last night. So I decided to try calling him on Discord, which to my surprise he actually answered.

“Hey man!” I said, trying to sound as energetic and as normal as I could.

“H- Hey,” He said sheepishly.

“Listen, about last night…” I started.

“I’m sorry,” Jacob said quietly.

“No no no, it's cool dude!” I said hastily, not wanting him to feel bad.

“I guess I kind of outed you?” He responded.

“Outed me to who? I think it's more like you outed yourself?” I said light heartedly, trying to keep things low key.

“Samantha knows?” Jacob said back, almost as if he was shocked.

I chuckled a little, deciding to take Mommy’s advice and just see where this would go.

“Samantha is my stay at home wife, who drives me around in the back seat of a mini van and makes me lunch. I’m honestly surprised it wasn’t more obvious,” I said in a joking manner.

There was silence for a bit.

“Wait, so like…are you…” Jacob said.

“I’m not gonna say it, but I’ll answer any of your questions honestly,” I responded.

“Is Samantha like… your Mommy?” Jacob said quietly, probably trying to ensure that his parents didn’t hear the question.

“Yea, practically full time,”

I could hear a long exhale, which I hoped was Jacob calming down a little.

“And you…like…use diapers?”

“Not 24/7, but close to it.” I said, a little nervous myself. I hadn’t openly said that to anyone but Samantha before this.

I could hear Jacob let out a nervous laugh in the background. “Sorry, this is just like an eye opening experience…”

“Is that a good thing or a bad thing?” I responded, not really sure.

“I guess I just never…I feel ashamed to…well you know. So hearing someone else say it…hell to know a couple who partakes in it is just…wow. You know?”

“Yea, I guess it's pretty normal for me now. I definitely didn’t think I’d run into someone else who liked it though,” I said.

“What's uh- if you don’t mind me asking. What's your little age?” Jacob said quietly.

I hesitated a bit. I felt as though I was revealing a lot of information without much in return. “Fluctuates a bit I guess, but probably like 3? What about you? Am I allowed to ask that?”

Jacob let out another nervous laugh. “If you're being so honest, I guess it's only fair,” Jacob said before pausing. I could sense a lot of hesitation but honestly I was expecting that. He’d probably never told a single person before.

“It’s hard to say since I haven't really gotten to experience…but like…1?” He said, before quickly adding, “That's weird isn’t it….”

“No no, chill dude. You don’t have to feel weird about this stuff with me…” I said before being cut off by Mommy as she walked in the door.

She stood in the doorway for a second, looking over at me with a puzzled look. “Is that Jacob?” Samantha asked.

“Yes, Momm- hun,” I said, weirdly catching myself as I realized Jacob would hear it. I could hear him try to conceal a laugh, which definitely didn’t make me feel any better but I could see myself doing the same thing if positions were reversed.

Samantha smirked down at me before grabbing the headset off my head and putting it on hers.

“Jacob, you free today?” Samantha asked firmly.

I could hear a hesitation, probably from Jacob being as caught off guard as I was.

“Uh- ye- yes?” I could hear him awkwardly say, probably unsure of whether the two of us had talked.

“Right, I’m gonna come pick you up. You’re gonna spend the night at our place,” Samantha said before giving me back the headset. I looked up at her with a puzzled face, unsure of what had just happened.

“Relax. You just keep talking to him, and I’ll go pick him up. Tell him to pack up his things,” She said, putting air quotes up as she said things.

I quickly hit the mute button on my mic.

“Are you sure? Like are you okay with…”

Samantha cut me off. “I am more than happy to, as long as you are cool with it,”

I stared at her. For once, I had no idea what she was planning in her head. “Um…” I started.

“Great! I’ll go pick him up!” She said as she left the room.

I could hear her grabbing the keys and heading out the front door, locking it behind her as I went to unmute the mic.

“Well…” I said, unsure of what to say next.

“Did she mean like, now?” Jacob asked, suddenly sounding pretty nervous.

“Uh, yea. She just left,” I awkwardly responded, now knowing that it wouldn’t be to long before we’d be facing these questions a little more personally, and under Mommy’s supervision.

“Oh. Guess I am coming to your place then,” He said awkwardly, probably completely unsure of what to expect.

Samantha had always been cool with helping Jacob as needed with rides, or meals, but we had never really taken it farther than that. Nor had we discussed it. Though, I had spent most of last night thinking about this very scenario, so I would be lying if I said I wasn’t at least a little excited to try something like this out?

“Yea, uh look. If you’re not comfortable with any of this just let me know and I can call her and tell her to turn around,”

“No, it's cool. I could use a night out of my parents house anyways,”

“Um, well…” I started, hesitating to say anything.

“What” Jacob asked.

“She wanted you to pack your, um…things?”

There was a moment of silence.

“What do you mean?” Jacob said nervously.

I’m sure he knew exactly what I meant, but wanted me to clarify and say it explicitly. “Whatever things you might have… that pertain to little space,”

“Oh…” Jacob said. “Are we uh-”

“Playdate…I think that would be the term…” I said awkwardly. Trying to keep him from saying anything else.

“Right…don’t have much in the way of that but guess I better get to it.”

“Yea, guess I’ll see you in a bit?” I said hesitantly.

“Yea…” Jacob said, before logging out of the server and off of Discord.

~~

I sat on the couch, anxiously waiting for Samantha to return with Jacob. My diaper was pretty damp already as Samantha hadn’t gotten around to changing me yet. Usually I was completely fine with being around people in a soaked diaper. Though, usually no body knew that thats what I was wearing underneath, and I’m sure it wouldn’t take Jacob long to put two and two together. I wasn’t quite sure what we were gonna do, but I was sure that Samantha was going to push things pretty quick as she always had. I heard the front door open and Samantha and Jacob walk in.

“Hey,” I called out as Jacob awkwardly shuffled his way inside.

“Hey-” Jacob said quickly, looking around as if he had never been inside their house before.

Nervously, Jacob made his way into the living room, placing his backpack on the ground and grabbing a seat on the couch as Samantha disappeared into the kitchen.

“Sooooo…” I started, feeling unsure of what to say.

“So,” Jacob responded, being just as awkward as I was being. To be fair, I was the host and we had just randomly invited him over so the weight was definitely on me to keep things entertaining.

“Did you get a chance to restock the shop this morning?” I asked, going with the first topic that came to mind which just so happened to be Minecraft since they had both just been on the server.

“Haha, no. Honestly I had just gotten on before you jumped online,” Jacob said.

I leaned over to whisper to Jacob. “Are you good at controlling your own boundaries?”

“What do you mean?” He responded.

“I mean I know Samantha, and she is beyond excited so I’m not really sure what is going to happen this weekend but I want to know if you need me to watch out for any boundaries she might cross or if you can manage yourself”

“I guess I’m not really sure what you mean?”

“What I mean is, she’s the one with a big Mommy Dommy fetish, and she loves to over indulge me so I am sure she will be pushing you way out of your comfort zone,”

“Oh yea…ok. She’s not going to like…” Jacob started before being cut off by Samantha.

“Lunch boys,” Samantha called out from the kitchen.

“Jacob, honey? Forgive me for being so abrupt but what's your little age?”

I gave Jacob a side eye and a smirk before getting up and making my way to the table catching a glance from Samantha as well.

“You, take your pants off so Mommy can keep a better eye on you,” She said as she set two plates down on the table. Both with little triangular PB&J’s without the crust, and a small serving of fruit.

With a wide eyed look from Jacob, I dropped my pants down to reveal my moderately used diaper that I had been in since last night. I gave a little spin for Mommy, which I realize also inadvertently gave Jacob the same view. I could tell he was a little out of place, but not to the point where all of the color had escaped his face. If anything he was blushing from my second hand embarrassment?

“Jacob, I’m sorry but I must have missed your answer,” Samantha said, sticking her head back out of the kitchen.

“Oh uh, I haven't ever really messed around with the…”

“1,” I said, cutting Jacob off. I gave him a quick smirk and gestured for him to come over to the table.

“Thanks,” Jacob mouthed, awkwardly making his way over to the table.

“Oh, we’ve got a little baby, huh?” Samantha teased from the kitchen as I watched her grab a bottle and fill it with milk as the biggest smile came over her.

I could tell this isn’t what Jacob was expecting when Samantha asked him to come over, but that he was somehow enjoying himself nonetheless. My theory was confirmed when Samantha placed a sippy cup full of juice in front of me, followed by a bottle of milk in front of him. He stared at it for a few seconds before looking up at me and then Samantha. I was pretty sure I saw a tear forming, but I wasn’t going to say anything.

“Th- Thank you…” Jacob said softly, looking back to his plate and picking up one of the sandwich halves.

“So after lunch we’ll get you a diaper to change into and maybe some of Devin’s clothes if you’d like,” Samantha said, sitting down next to me.

Jacob slowly nibbled on his sandwich, eying the bottle.

“So, do you boys want to get high? I know it really helped Devin get into the headspace when we were first starting,” Samantha said, looking at me for a brief minute before shifting her gaze to Jacob.

It was really interesting. I half expected myself to feel more uncomfortable then I did. Especially with my wife becoming so eager to get Jacob involved in our role play. But it honestly did sound fun. To have someone else involved, especially if it had Samantha this riled up.

“Uh…” Jacob started, looking at me for advice while I downed a good portion of my sippy cup. I smiled, trying to let him make his own choices. After all, he did say he was comfortable setting his own boundaries. “I’ve uh- never smoked before…”

“Oh nonsense. We don’t smoke either, we use edibles. Plus, I’ll be watching over you both so you don’t have anything to worry about,” Samantha said, getting up from her seat to go and grab the edibles as if Jacob had already answered.

“I uh- sure, why not?” Jacob said, quickly looking at me with a very nervous look.

“That's the spirit!” Samantha called out from the other room.

“Alright, here's one for Jacob. Should be enough since it's your first time. Devin, baby. You take three.”

“But I usually just do two?” I objected.

“Exactly, we’re gonna get you really out there to help your friend transition,”

I gave her a big smile. I loved her, and couldn’t believe how excited she was, but I was definitely a little nervous with where all of this was going.

“Right, you just chew that and drink at least half of your bottle, Jakey. Then we’ll get you in a nice thick diaper.”

He did as instructed, almost without hesitation which told me everything I needed to know about his mental state.

“Now, since it's your first time, do you want Mommy to do it or do you want to do it yourself?”

Jacob stared wide eyed back at her, switching his gaze to me after a short moment obviously looking for help. I giggled at the idea in my head before realizing he was probably asking for my permission more than anything. Like why would he turn that offer down?

“Mommy knows best,” I said with a smirk, which I think even caught Samantha off guard as she turned to look at me. I simply shrugged and began sucking down some of the remaining juice to wash the taste of the gummies out of my mouth.

Jacob nodded, more than likely being rattled with nerves and unable to speak.

“Perfect, I’ll go grab a matching diaper. Can you lay down on the floor right here, sweetie?”

Jacob looked at me, completely red faced. “Is she actually going to…”

I nodded. “Yup, we're both gonna get to see your privates,” I said, holding back a laugh as Jacob turned an even brighter shade of red. I wasn’t quite sure where this sense of teasing was coming from, but it was kind of fun to embarrass Jacob and watch his face turn bright shades of red. I could definitely see why Mommy finds this to be so much fun.

“You’re not going to actually look…are you?” Jacob said nervously.

“If my wife is changing your diaper, I think that's the least you can do,”

“Are you still answering questions honestly?” He said, still sitting in his seat.

“Mommy doesn’t let me lie at home, so yes,”

“Are you- bisexual?” He said quietly just before Samantha came back into the room with a diaper and bottle of baby powder.

I nodded at Jacob as Samantha talked over me, leaving Jacob in yet another wide eyed trance as he remained in a locked trance with me.

“Jacky, come lay down on the floor,”

Slowly, he did as he was told and kneeled down to get on the floor in front of Samantha. It didn’t take long before he was laid out in front of her, with an obvious bulge beneath his pants. Samantha gave me a quick glance that told me all I needed to know before she started to unbutton his pants and pulled them down.

I made my way into the kitchen, quietly opening the freezer to grab an ice cube from the tray. I made it back into the living room, just as Samantha finished pulling off his underwear, leaving him exposed to the both of us at full mast.

“Hmmm,” I said, kneeling down beside him as I handed Mommy the ice cube.

Jacob was beyond embarrassed just from the whole experience, let alone me being there to the point that he had his arms thrown over his face. He let out a loud whimper as Mommy pressed the ice cube against his hard member.

“Shhhh baby, shhhh” Samantha cooed. “Mommy knows just how to take care of little babies like you.”