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Caring for Little Ollie Page 3
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He’d look over his shoulder and hold out his sippy cup. Daddy, can I have some more juice?
Oh man, that’s what he’d call me—Daddy.
I'd had a boyfriend call me Daddy before but it had been in a more joking manner but imagining Oliver saying it to me in that innocent tone unleashed something needy in my body. I wanted to fuck him while he looked at me with those innocent eyes and moaned for his Daddy.
I realized I’d been standing there a while not saying anything when he got this wild look in his eye. That’s when I noticed the fear. He wasn’t just embarrassed. Oliver was actually terrified and I’d just stood there like an idiot letting him stew in his thoughts.
“Hey, it’s okay.” I reached for his face to cup his cheek and felt a twisting in my chest when he flinched back as if I was making a move to strike him. “Everything is okay,” I cooed, stepping close and cupping his cheek gently.
I wrapped my other arm around his shoulders and pulled him into my tight embrace hoping the warmth and reassuring presence of my body would break through his panic. I knew my smile turned silly when he pulled his free arm up between us as if to make himself as small as he possibly could while nuzzling his face into my chest. He was the sweetest thing.
“Excuse me.”
I looked over at the woman now standing beside us, my hands still holding Oliver to me.
“Is everything alright over here?” Her gaze pointedly fixed on the man in my arms.
I gave her a polite smile. “Yes, my boyfriend sometimes has panic attacks but he should be fine in a moment. He just needs some time to calm down.”
She eyed me suspiciously but when Oliver didn’t deny my words or pull away from me, she had no choice but to nod and walk away.
Still in my arms, Oliver tilted his head back and stared up at me in disbelief. “Boyfriend?” His voice cracked but I could see the glimmer of hope in his eyes.
I smiled and shrugged. “Someday?”
“But…”
“I know.”
“But that’s the thing, you know.” He bit his lip and glanced down. His fingers plucked at the fabric of my shirt as if picking off invisible balls of lint.
“And I’m still here. We’ll need to talk about it soon because it’s not scaring me away.” Going on instinct, I shifted my hand down to his chin and lifted his head. I waited for his eyes to meet mine before taking my chance. “Now, about that date.”
His smile was radiant and I knew in that moment that I would do anything to keep that look on his face.
“Yeah?”
“Yeah.”
He seemed to have forgotten he was about to give me his number so I reached for the phone he held loosely between us. I pressed the power button and tsked when there was no lock screen. We were going to have to have a talk about safety. He blushed and wiggled in my arms when I gave him a stern glare. Responsive. Perfect.
I pulled up his contacts and added my information. I shot myself a quick text and waited for my phone to vibrate in my back pocket before handing it back to him.
“I’ll text you tomorrow to set up the details of our date. If you need anything from me in the mean time, you can text me.”
He clutched his phone to his chest and nodded.
“I mean it. You need anything at all, you text me.”
“Yes, sir,” he whispered the words softly into the air. They were a quick punch to my system. I knew he felt my reaction to his words when he smiled and looked down at where our lower bodies touched.
I lifted my hand and brushed my fingers against his cheek once again, unable to help myself. My thumb swept against his bottom lip. “Good boy.”
I was all about that positive reinforcement.
Ignoring the slight moan that escaped his parted lips and the hard cock I felt pressing against me, I winked and forced myself to pull away from him. I gave him one last lingering look before turning and walking away.
Exiting the store, I stopped next to my car and smiled when I pulled out my phone and read the message I’d sent myself. I imagined the stunned yet hopeful look on his face when he finally read it. I quickly set up Oliver’s contact in my phone, his name the same message I’d sent.
Maybe My Baby.
Slipping my phone back into my pocket, I unlocked my car and got in. There was a lot I had to do before our first date. First things first, I needed more information.
I drove home in silence, my mind still focused on Oliver. What was it about him that drew me in? I’d avoided submissive types in the past but there was something about him that cut through all my defenses. The second his eyes had met mine, he’d cut straight to the heart of me. Why? Why him? Why now?
I spent the short drive home rolling the questions around in my mind. Did I need to know the whys? When all was said and done, would they matter? I was willing to give in to the desires I’d always held back for Oliver. Did I require any more than that? I had something he needed and wanted. Could I keep that from him because I was scared he wouldn’t want me when the truth came out?
I thought about it and as I entered my house and looked around, picturing Oliver in every space. A resounding no echoed in my head. He had come into my life in a split second, had changed everything, and I was surprisingly okay with it.
Daddy.
God, just thinking of that word felt so right. I’d wanted to call myself Daddy for so long, to claim that title, that just thinking of it caused ripples of desire to course through my body. I groaned low in my throat just thinking of it passing Oliver’s lips.
Spinning away from my living room, I made a beeline for my office. I blocked out everything else needing my attention and focused on scanning the bookshelves that lined the walls.
“Come on, I know you’re here somewhere,” I whispered as I crouched down and read the titles. “There you are.”
Reaching down, I plucked the books off the shelf and dumped them on my desk along with my book bag. Six books on BDSM weren’t much but it was a start. I flipped open the first and was immediately disappointed. I hadn’t read any of them in several years and I couldn’t help hearing the slightly condescending tone the author couldn’t help imparting in their words.
Snapping it closed, I tossed it aside and reached for the next and found more of the same. Worse, all the information was too impersonal and cold. Reading about the embodiment of submission wouldn’t help me become a good Daddy to a little but it did give me some ideas about getting him into a submissive frame of mind. Biases in health care or the politics of representation wasn’t what I was looking for either but it was some good information for future reference.
Okay, so all the books I owned were a bust. Turning on my laptop, I opened a web browser and did a quick search. Now we were talking. I stayed in my office for hours reading every article, book, and blog on age play I could find.
Sufficiently satisfied for the moment, I slouched back and contemplated the ceiling and all that I’d read.
I liked the idea of the man Oliver needed me to be. If I was that man was the question. All the characteristics of a Daddy aligned naturally with who I already was but pushed them to the nth degree.
I’d always been supportive and protective of my partners, preferring to take the lead in my relationships. A few boyfriends had accused me of being too controlling but I had the feeling Oliver wouldn’t see my behavior in quite the same light. If anything, he probably wanted me to be a little more controlling than I was comfortable with at the moment. Overall, age play seemed like a good fit for me.
I’d learned so much but I still had so many questions.
How much time did Oliver need in little space? Or was it that being little was just another part of who he was and age play was when he physically expressed his littleness? Did aspects of age play bleed out into everyday life? Did he take a bath every night with his toys and did he eat all his food from children’s plates?
How old was he when he was little? Was he potty trained?
I groaned and rubbed my eyes. That had to have been the strangest question I’d ever asked myself about a potential partner. Well, no point in stopping now. Did he wear diapers? Sometimes or all the time? Did he use them? If so, to what degree did he use them? What about training underwear or little boy tighty-whities?
Moreover, how would I feel being around Oliver when he was little? Would I like it? All I’d imagined said I would but would actually engaging with him be different?
Moreover, at the moment, it felt sexual to me but what if that changed? What if Oliver didn’t find it sexual at all? Some littles didn’t like sexual contact in that headspace but some did. Where would Oliver fit? Where would I fit?
The sound of my phone’s notification alert going off interrupted my internal ramblings. Grateful for the moment’s reprieve, I picked up my phone and laughed. Speak of the devil.
Maybe My Baby: Hello? Are you there?
I leaned back in my chair and kicked my feet up onto the desk, settling in for some good old-fashion text flirting.
Me: Hi, cute pie.
Maybe My Baby: *blushes* Really?
Me: Did I do something?
Maybe My Baby: Yes! You’re driving me crazy!
Me: And how did I accomplish that?
Maybe My Baby: I can’t stop thinking about you.
My sweet boy. I’d noticed he hadn’t said much at the store but it seemed the anonymity of the screen was giving him back his courage.
Maybe My Baby: And just when I’ve decided to give you a little piece of my mind for invading my thoughts, I see the Maybe My Baby message and now you’re being all cute with me!
Maybe My Baby: It’s not fair.
Me: When were you thinking of me?
Maybe My Baby: That’s what you got out of all that?
Me: Oliver
I could almost see him shiver at the implied warning of my message.
Maybe My Baby: When I was making dinner.
Okay, not expecting that but I could roll with it. Moreover, this was a great opportunity to find out how he saw our relationship progressing and what he needed from me.
Me: And?
I replied, knowing he needed the encouragement.
Maybe My Baby: I pictured us making cookies.
Was he testing me? Seeing if I was in even with the mundane stuff?
Me: Mmm sounds like fun, did you get to lick the bowl?
Maybe My Baby: Of course. I was good.
I shifted in my chair as desire coursed through me. I reached down and absently rubbed my cock through my slacks. I knew what he was trying to say without saying it. He had been a good boy and Daddy had given him a treat. Not even a day and he already knew how to push my buttons—buttons I was only just realizing I had.
Maybe My Baby: So good, I got to have two cookies after dinner.
Me: Two?
Maybe My Baby: Yep. Two.
Maybe My Baby: Growing boys need their nutrition and chocolate chip cookies are an excellent source of… something.
I laughed. So, that was how it was going to be. He was going to wile me with his adorable zest for life. I loved it already.
Me: Of course, growing boys need their vitamins and good boys need cookies although I’m not completely sold on their nutritional value.
Me: What else did you do today while thinking about me?
There was a long silence and I just knew he was working out how much to tell me.
Me: The truth, Oliver.
Maybe My Baby: I played.
I could hear the defiance in his words. It was as if he was daring me to go there, test number two. That was fine, I’d meet his bluff.
Me: Oh? What were you doing?
Maybe My Baby: I was coloring and couldn’t help wondering what it would be like if you were here.
Maybe My Baby: I’ve never had anyone here before.
Maybe My Baby: You know. When I’m…
Maybe My Baby: little.
I understood and it broke my heart. Making connections with others was hard, making them when you wanted something so outside the realm of normal was exponentially more so. He’d never shared this with anyone before. I was the first. I studied my phone in silence. I could very well be the last. I’d be the last if he became my boy because I knew once I got the taste of him in my system, I’d never get him out or I’d be the last if I screwed this up and he never trusted anyone else again. I needed to get this right.
Me: When I got home from the store, I stepped inside and I couldn’t help imagining you in my house. I looked in the living room and there you were building a fort with me. We dragged all the blankets and pillows I had inside and spent hours cuddling together while watching videos on my tablet.
Me: I looked in my kitchen and you were there too, watching as I made you pancakes for breakfast. It was cute how you stood by my side to ensure all the blueberries were equally spaced. I gave you a look when you pointed out an empty spot but you just giggled and gave me that sweet smile I already love.
Me: You were in my bedroom too. I heard you laughing from my office and knew you were up to something. I stood and followed the sounds. You were bouncing on the bed like a naughty monkey. I wanted to laugh but you’ve been told time and time again not to do that. No matter how cute you look, rules are rules for a reason. It’s too dangerous. What if you’d hurt yourself? Now it’s time for your punishment. Come give me a kiss before sitting in your naughty chair.
Me: What about my bathroom? When I go to take a shower tonight, will I find you there as well?
I waited for his response but nothing came. The seconds passed into minutes and I cursed myself. Dropping my feet to the floor, I cradled the phone in my hands and reread what I wrote. Was it too much? Did I push too far too fast? Had I already ruined things before they’d started?
My phone dinged startling me.
Maybe My Baby: No, silly. I’ve already had my bath.
Maybe My Baby: And I only eat waffles. No pancakes.
Okay, so it sounded like pancakes were a hard limit—noted.
Then, he sent me a picture and I instantly understood.
I’d shared myself with him and now he was sharing himself with me.
He was sitting cross-legged on his bed with his hair still damp and sticking up from his bath. His blankets were a sensible navy but I spied the pastel yellow throw he had clutched in his hand and the teddy bear propped on the pillow behind him.
He had on what looked to be a pair of drop-crotch, footed pajamas but they weren’t because I could see his little feet sticking out. The arms and legs were blue but the entire stomach area was white. I thought it had a hood but I couldn’t tell from the angle of the image he’d sent me.
Anyway, it didn’t matter what he was wearing because he was staring up at me with that same smile I’d seen before. His eyes were a little red around the edges even though they practically sparkled with delight.
I held my finger over the image and downloaded it to my phone. With a few swift taps, I could see him every time I looked at my screen. I’d always thought that people who had pictures of their boyfriends or girlfriends as their home screen were a little weird but now I got it. Who wouldn’t want to look at that cute face every chance they got?
Me: Thank you. You look absolutely adorable.
He sent me another picture and I laughed.
Maybe My Baby: I’m a shark. Grrr.
He’d pulled the hood of his pajamas up and I could clearly see that he was indeed a shark. The little white triangle teeth framed his face.
Me: You are the cutest shark I’ve ever seen. I could just gobble you right up.
Oliver was so open, so free. He was quickly becoming my new addiction. Caffeine had nothing on him. I was positive that I’d laughed more in the last hour talking to him than I ever had with any of my previous boyfriends. They’d always been so worried about their appearance and how others perceived them. It was almost as if letting me see their vulnerable side would have diminished them in some way. Not Oliver though.
Maybe My Baby: Are you sure?
Maybe My Baby: About me, I mean.
I took a deep breath and thought about my answer.
Me: I was familiar with littles and age play when I met you in the store, that’s how I knew what you were. You blushed and stammered when I asked you about children and I could see the embarrassment and fear in your eyes. I realized all the things in your basket were yours. I was still interested. When I got home, I locked myself away in my office and spent hours and hours pouring over information about age play. I’m still interested. I have no idea how this is all going to play out but I’m going into it with open eyes. That’s all I can promise you.
Maybe My Baby: That’s good enough for me.
I glanced at the clock and groaned. It was almost midnight and I had to be up at six to make my seven o’clock appointment.
Me: It’s getting late and I still need to take a shower. I’ll see you tomorrow.
Maybe My Baby: *pouty face*
Me: It’s time for bed.
Maybe My Baby: Yes, sir.
I grinned. That scamp.
Me: Good night.
“My boy,” I added aloud knowing it was too soon to claim that from him.
Maybe My Baby: Good night.
I smiled hearing the unspoken ‘Daddy’ on the other end.
Chapter Three
Oliver
It was too much. Definitely not first date material. I tugged at the hem of my shorts as I stared into the mirror. There was nothing inherently wrong with my outfit. Marshall had said to wear something comfortable and casual. I just wasn’t sure if red overalls, a black and white striped t-shirt that showed a hint of skin at my sides if I stretched a little too far, and black canvas sneakers were what he had in mind.
My outfit was perfectly acceptable even if it made me look a decade younger. Some people would think I was fashion forward and some would be scandalized but only Marshall would truly know why I wanted to wear it. I kicked out a foot and rolled my ankle. I thought I looked cute and hopefully, Marshall would think so too.