by Quinn Ward
“I might need bedtime, Jay,” he explained. “I’m not so good at going to sleep on time. And maybe sometimes you could help me with that.”
“How would I help you?”
Ash shrugged. “I don’t know. Maybe you could help me get into my jammies and then read me a story. You’re a good snuggler, so maybe that would help me sleep. And not now, but later, maybe—” He squirmed, trying to get away from me.
Interesting. I wasn’t sure what he was thinking, but it obviously affected him. He reached for his crotch, remembering at the last second that he wasn’t supposed to. I waited until he buried his hands under his legs before moving. It was a risk, but I laid my hand over his dick, feeling the way he throbbed against me. “What has you excited, Ash? Is there something you want Jay to do to you when you’re ready?”
Even though the room was only illuminated by my desk lamp, I could see the way Ash’s face flushed red. He didn’t speak, so I used the time to scroll through the things I’d seen that might embarrass him to admit he wanted.
“Do you want a bottle at nighttime, Ash?” I plucked the binkie out of his mouth, dragging my thumb over his bottom lip. “I bet warm milk in a bottle would help you sleep better than this binkie would.”
He squirmed and whined. I pushed my thumb into Ash’s mouth, and he started to suck on it. Which, of course, had my dick waking up and pressing against his hip.
Ignore it. You don’t need this as much as he does. Focus.
“Yeah, I think my buddy likes the idea of sucking on a bottle,” I cooed. “But you have to tell me if that’s something you want.”
Ash nodded. I had no clue if he was saying he was up for bottles or that he’d tell me if he did. Shit, this was going to be tricky as fuck. There wasn’t any way we’d be able to wander down to the kitchen and fill a fucking bottle. What in the hell was I thinking?
Logistics later. Helping Ash now.
“And little boys who keep playing with their winkies might need a bit of padding down there,” I said, measuring my words, hoping I sounded stern. “I might need to order you some training pants for when you’re sleeping.”
“Not diapers?”
“Would you want diapers, buddy?” I’d figured they would be off-limits as long as we were at school. Training pants would be easy enough to hide in the bottom of the hamper until laundry time. “Maybe we should save those for when we’re on break. That might make you more comfortable.”
“But training pants until then?” He was very interested in that idea. I rubbed my hand up and down his length a few times, teasing him. He arched into the touch. “Jay, please.”
“Please what, buddy?” I gave him a quick squeeze. “You already made one mess. Do you need more rubs before I get you cleaned up and ready for bed?”
“You haven’t had any special kisses yet,” he pointed out, as if I’d forgotten that I’d been achingly hard all fucking night. Ash wiggled around, cupping my balls in his hand. It’d been so long since anyone else had touched me that I nearly exploded. “Can I give you special kisses, Jay?”
“Do you want to give me kisses, buddy?”
In answer, he slid off my lap and between my legs. He fumbled with the button on my jeans. I helped him out, adjusting myself as I lifted my hips. He wasn’t graceful by any stretch, but he stared at my body with such adoration I couldn’t help but feel special. “I need you to help me, Jay. I never did this before.”
I knew he hadn’t done much, but not even a blowjob? Damn. I wasn’t sure if I should feel special or scared out of my damn mind. I’d never been anyone’s first anything, and now I was his first everything, except maybe a kiss.
His hand shook as he wrapped his fingers around the base of my dick. He stared at it, turning his head this way and that, like he was trying to determine the best approach. I groaned when he gave me a tentative stroke.
“You’ll make sure I do a good job, Jay?” He sounded terrified, but I knew he needed this as much as I did.
“I’ll tell you what to do, buddy, don’t worry.” I scooted lower, lifting my hips as Ash stroked me. He cupped my balls with his other hand, rolling them back and forth. His movements were unsteady, but the way his tongue peeked out between his lips told me he wanted this. “Go ahead, buddy. Give it a kiss if you want.”
“I bet kisses feel real good, Jay.” Oh, my buddy had no clue, but he would soon enough. Not tonight, because he’d already gotten to come once, and he needed to understand he couldn’t get off whenever he felt like it. “You won’t hurt me with it, will you?”
“No, never,” I promised him. “We’ll go nice and slow so you can get used to feeling my cock in your mouth, okay?”
“Daddies and Jays don’t have winkies,” he said as he leaned closer. “Big boys have cocks.”
“That’s right.” I was following Ash’s lead here. “Do you want to taste my cock, buddy? I know how much you love sucking things.”
“You probably taste better than my binkie,” he said.
I clobbered my head on the edge of my desk when it fell back. I’d lost my erection after dealing with Zach’s bullshit, but all it had taken was feeling Chase in my arms and I was right back to the edge of the fucking cliff.
I curled my fingers loosely in Chase’s hair, guiding him closer to my dick. “You don’t have to think about how I’ll taste, buddy. It’s all yours. Kiss it.”
He bent down, nearly going cross-eyed as he tried keep his eyes open as he got closer to my dick. His tongue peeked out, licking the precum from my slit. My hips bucked off the bean bag, startling him enough he fell onto his ass. He licked his lips a few times, face twisting. “It’s not like I thought it would be.”
“Is that good or bad?”
“Good, I think.” He kneeled between my legs again. “But maybe I should have another taste to make sure.”
“By all means.” I leaned back, draping my arms over the sides of the bean bag. When he sucked my tip into his mouth, I grabbed onto the faux leather material, determined to not fuck his face the way I wanted to. “That’s so good, buddy. Keep doing it just like that.”
He whimpered as he suckled the head of my cock. His hand gripped the base, jerking me off. “Such a good boy. I think someone’s been watching videos he shouldn’t. No way are you this good without porn.”
“I wanted to make sure I’d be good at it,” he explained when he leaned back to catch his breath.
“You’re so good, buddy,” I praised him, twisting my fingers in his hair. “Now, I think it’s time for you to stop teasing me. It’s not going to take long for me to come, and when I do, I want it to be down your throat. Do you want that, too, Ash? Are you going to be my dirty little boy, drinking my cum like a before bed treat?”
The dirty talk was unexpected, but Ash seemed to get off on it, so I kept rambling as he took me deeper into his mouth. His mouth was hot and greedy. It was probably the sloppiest blowjob I’d ever had, but it was also the only one that left me feeling completely wanted. He was desperate to please me, to make me come, and that shined through in every slurp and messy twirl of his tongue around my length.
“Keep doing that, buddy, and I’m going to give you your treat,” I warned him. He moaned, and I noticed him reach between his legs. “Uh-uh. You don’t get to rub your winky. You didn’t ask permission.”
His eyes grew wide as he looked up at me. His mouth went slack, allowing my dick to slip free. “Please Jay, it hurts so much. I promise I’ll be good if you let me get sticky.”
“Not yet,” I said in the sternest voice I could manage. “It’s my turn for kisses. And don’t think I forgot that you got sticky earlier, and you didn’t ask then, either.”
“But you made me,” he complained. His voice pitched higher as it dawned on him that I might not let him get off again tonight. “I swear I didn’t mean to do it, Jay. Please…”
I curled a hand around the base of my dick, offering it to him again. “You know what you need to do. If you’re good, maybe
I’ll help you get sticky.”
“Would you…” He huffed a few times, pursing his lips. “Do you want… Can…”
Fuck, he was cute. “Use your words, buddy. If you want something you need to tell me.”
“I wants kisses too, Jay,” he pleaded. “Can you give me kisses?”
“Get to work, buddy,” I urged him. “Show me how bad you want it.”
Apparently, my little guy was motivated by being challenged. He put every trick he’d learned by watching porn into finishing me off. He palmed my nuts, allowing his fingers to massage my taint as he sucked my entire length into his mouth. I wasn’t sure if it was Chase or Ash sucking me, but I couldn’t be bothered to fucking care as long as he kept working me the way he was.
I fisted his hair, giving a sharp yank when my sac drew up tight to my body. It was the only warning he was going to get if he wasn’t ready for a mouthful of cum. My boy shocked the shit out of me by sucking harder, hollowing his cheeks as his tongue worked the underside. I bit down on my knuckles hard enough I broke skin, failing to stifle my grunts as wave after wave of orgasm hit me. My guy never pulled off, sucking down every spurt I gave him.
I was not expecting him to flop back onto his ass, burying his face in his hands when it was done. I quickly scooped him into my arms, pulling him into my lap. I couldn’t escape the feeling that I’d made a huge mistake. “Hey buddy, what’s wrong? Did I hurt you?”
I wouldn’t forgive myself if I’d lost control and done something he hated. Ash buried his face against my chest, shaking his head. He clung to me as if he was afraid I was the one who regretted what we’d done.
“Chase, I need you to talk to me.” I’d read some shit about how I shouldn’t pull him out of little space when he was as deep as he’d been, but I fucking needed Chase right then, not Ash. I adored my buddy, but it was my roommate I needed to reassure me that I hadn’t fucked this all up. “Come on, tell me what’s going through your head.”
“I came,” he whispered. His tears dampened my skin. “I can’t believe I did that twice tonight and you never even touched me. It’s embarrassing.”
“It’s fucking hot, is what it is,” I corrected him. Seriously, I wasn’t sure there was much better for the ego than knowing I’d done that to him. Just talking to him and giving him what he needed turned him on so much he’d gotten off without touching his dick. “Don’t feel bad about that.”
“But you told me I couldn’t.”
Shit. Okay, so yeah, I had, but I was working without a manual here. As much as I hated thinking about him while my dick was still out, I took a few seconds to think what my uncle might say if he were in my shoes. I was definitely going to need his guidance if Chase and I had any hope of making this shit between us work.
“We both have to learn what we’re doing, Chase,” I explained so he’d understand neither of us were going to do everything right all the time. “The way I see it, for tonight we can say you got caught up in what was going on. Trust me, you aren’t the first guy to come before he was ready. It’s a fact of life.”
“But you said,” he repeated.
I knew what I needed to do. Tomorrow, we’d have to talk about boundaries and when he’d be big or little, but tonight he’d been Ash, and he’d disobeyed me. “You’re right, I did. I can’t do anything about the first time because we hadn’t made a rule yet, other than you were supposed to ask me before you touched yourself. But the second time, you knew you were supposed to wait for me, and you didn’t. I think we need to figure out a punishment, don’t you?”
“Yeah, I was a bad boy,” he responded somberly.
Spanking him was out of the question. That was something I’d have to be careful about because I didn’t want to wake up the rest of the suite. I eased him off my lap and stood, dragging my desk chair to the far corner of the room. “Come here, Ash.”
His shoulders drooped as Ash crossed the room to me. He folded his hands in front of his body, trying to hide the wet spot from me, which only reminded me that he was wet and sticky. I gave his body a down-up perusal as I considered what I wanted to do. “Take off your messy pants, buddy.”
He hesitated, staring up at me. He blinked hard a few times, looking like he was about to burst into tears. It would have been so easy for me to give in, but I needed to be the disciplinarian. “Now, Ash, unless you’ve decided you don’t want me to be your Jay. If you have, that’s fine. We can go back to being roommates—”
“No! That’s not it!” he cried out. “I just… I’ve never… I…” Ash tugged at the bottom of his t-shirt. He pursed his lips and kicked the leg of the chair. When he found the courage to speak, his words were so jumbled I could barely understand them. “Ineverbeennekkidinfrontofpeople.”
“Oh, buddy, that’s okay,” I soothed him once my brain parsed his concern. “It’s just me. And you can’t stay in those sticky clothes. They’re probably really uncomfortable.”
“Yeah, kinda,” he agreed. “But you promise you won’t laugh?”
“Why would I laugh at you, buddy?” Yes, he was leaner than I was, and smaller all around, but that was part of what made him fucking irresistible. I wanted to scoop him up and carry him around in my pocket to keep him safe. “No, you know what, I don’t need to know why you think I would laugh. It hurts me that you think I’d do anything to hurt you.”
As much as I wanted him to take off his clothes as part of his punishment, he also needed some encouragement. Maybe we’d start making him have mandatory undies time so he could get used to being on display for me. I gathered the hem of his shirt and started lifting it. “Hands up. Jay’s going to help you this time.”
The entire time, I explained to him what I was doing and why. He seemed surprised when I dropped to my knees to pull off his pants. His hands shifted in front of his dick again. I separated them, making it clear he was to keep them at his sides.
“You were naughty tonight, weren’t you, Ash?” I asked once he was completely naked and I stood in front of him. “Can you tell me why you need a punishment?”
“Because I got sticky when you didn’t tell me I could,” he responded. I waited for him to protest, again, that it wasn’t his fault, but my good boy said nothing.
“You’re going to sit in the corner for a few minutes so you can think about what you did,” I explained. He fidgeted when he looked down at the hard-plastic chair, then back up to me. “Yep, it’s going to be cold on your bum, but this isn’t supposed to be comfortable, is it?”
“No, Jay. I am sorry for getting sticky.”
“I know you are, buddy.” I kissed his cheek and laced my fingers through his, leading him to the time out chair. “But that doesn’t get you out of some thinking time. Now, you sit here like a good boy and I’m going to get a rag to clean up your mess. Then, we’ll get you into bed.”
“You’re leaving me alone in here?”
“I’m only going across the hall, and the door will be closed,” I reassured him. I knew I wasn’t supposed to leave him, but it couldn’t be comfortable having dried cum on his skin and I wanted to take care of him. Tomorrow, I would be going shopping so this wouldn’t be an issue in the future. If we didn’t have roommates, I would have left the door open so he could see me the entire time. “As soon as I get back, we’ll get you cleaned up.”
“Okay.” Ash sat on the time out chair, jumping when his bare bum hit the cold plastic. He crossed his arms and pouted but didn’t otherwise protest.
“Good boy.” I bent down to kiss the top of his head. “I promise, I’ll hurry back.”
In my haste to get to the bathroom and back before Ash got upset, I wasn’t paying attention and ran into Matt as I darted across the hall. “Shit, sorry about that. I wasn’t watching where I was going.”
“No worries. Late night?” Matt glanced past me to our bedroom.
“Yeah, Chase and I went out for a bit.” That wasn’t odd, roommates hung out. It was totally normal. “What are you still doing up?”
/> “Trying to finish a paper. This semester is going to fu—” he stopped himself, checking over his shoulder like he expected someone to be there. “It’s tough, man. I’m thinking I might have to change my major if it stays like this.”
“You’ll figure it out.” I patted his shoulder, easing past him. “If you want, after breakfast tomorrow I can help you with your paper.”
“That’d be fu— I mean, yeah, that’d be cool.” That was twice he’d cut himself off from swearing. Any other time, I’d have questioned him about it, but I didn’t have time to chat. There was a naked boy in my bedroom who needed me to help him get ready to sleep. “I’ll catch you later, Jayden.”
“Night, Matt.”
8
Chase
Maybe it shouldn’t have shocked me how much less stress I felt after Jayden started helping me. Being little wasn’t a dirty secret I had to keep to myself anymore, and it felt like I could breathe. Even cooler was he sensed when I needed some Ash time. It was commonplace for him to bring me Pika or my binkie when I was frustrated and stressed out by school.
The only downside was I hated leaving our room when we were home, because outside, I had to be Chase all the time. But I’d promised him I was going to try to do better, and I’d always keep my promises.
“Hey buddy, do you want to help me with breakfast?” Brandon asked when I entered the living room. I wasn’t sure how I felt about him picking up on Jayden’s nickname for me and using it, but I didn’t say anything. As far as he knew, it was simply a casual nickname like bro or dude.
“Sure. What do you need help with?” Brandon frowned when I dumped three spoonful’s of sugar into my coffee. I giggled when I caught myself before telling him he wasn’t my Daddy and he couldn’t tell me what to do. Jay didn’t mind me having my sugary goodness in the morning. When he quirked an eyebrow as if to ask if I really needed that much junk in my coffee, I stuck out my tongue before cradling the new mug Jayden had bought me between my hands.