Rebranding [Tier 3 Exclusive] (Patreon)

In the summer between my sophomore and junior years of college, I felt it was time for a rebranding. Just because I had gotten through 20 years of life as “Oliver” didn’t mean that it was all that successful of a run. Sure, I had decent enough grades and proficiency with a flute, but I had little else to show for it. I had few friends. Barely any social life. My virginity.

It was more than time, then, to retire the persona of “Oliver.” The shy and sheepish boy who blended into the background. The introspective bookworm without any friends or lovers.

It was time to unveil the new version: “Olly.”

“Olly” would be more gregarious and social. Confident. Fun to be around. Willing to take a risk or two.

I begin a soft rollout of Olly early in the summer. I try to initiate some conversations with strangers while I’m out and about. I make small talk with the young man folding pants in the store I’m buying shorts from. I compliment the young woman’s pink hair while she makes a burrito for me. I complain about the weather with the mailman.

I feel like Olly is doing rather well. Either it’s easier to be more extroverted than I thought it was, or I just have 20 years of socializing to get out of my system. Either way, I’m pleased with the results.

The real test lies in romance.

I’ve assigned Olly a goal for the summer: to get laid. Any wallflower can step forward and start a conversation or two. But I had gotten it in my head that I hadn’t truly accomplished anything if I remained a zero in the love department. Admittedly, I was well aware of how silly this sounded. It sounded as if it had come out of one of those crass teen comedies I had avoided most of my life. Yet I remained steadfast in my resolve: Olly would need to score.

There had never been a shortage of young and attractive ladies in the world that “Oliver” had lusted after and crushed on. I was open to accomplishing my goals with any of them, truthfully. But Olly’s eyes were on Melinda.

I didn’t know her well, and I was positive that she had no idea who I was. We had only the briefest of interactions a month earlier, when I was shopping in the department store that she worked at and got her assistance in finding the hardware department.

‘Love at first sight,’ is a ridiculous concept–right up there with letting your new personality revolve around losing your virginity. But I was bitten quite hard upon meeting her. Her bouncing golden locks of hair. Her big blue eyes. The melodic tone in which she spoke. Those plump breasts… The entire package was adorable to me, and I wanted her in a way that I had never really wanted anything before.

I’d hesitate to say that I ever actually stalked her. But, perhaps, my behavior for that first month of the summer was a little less than…traditional. I made two or three stops in her store a week. I’d pick up a few trivial items and then patrol the store, hoping to see her again. I usually would, finding her in the infant’s department where she would be restocking diapers and answering questions from other customers about strollers.

It shouldn’t have been that hard to just approach her and have a conversation. I’d just introduce myself, compliment her, and see if she wanted to go out sometime. That was literally all that I had to do, and I knew it. Instead, I spent every moment while in the store agonizing over just approaching her.

“Hi there. Can I help you with something?”

Ultimately, it would be her who approached me. Again–though she didn’t seem to recall me from the first time we interacted.

“Hi,” I said. It was the opportunity I had wanted. All that I had to do–all that “Olly” had to do–was put it out there that I thought she was gorgeous and wanted to know if she’d go out with me sometime.

Instead, I panicked and grabbed a random item off the shelf.

“I was hoping you could tell me about, uh, these?”

“Diapers?” she asked curiously. “What about them would you like to know?”

I looked down at my hand where I held a package of baby diapers. I had no idea where I was going to go from here. Every instinct was urging me–screaming at me–to put the diapers down and start over.

I short circuited a little, attempting to put the diapers back on the shelf only to drop them onto the ground as I stumbled over my words. “I…uhm…well, you know…”

She knelt down, picking up the diapers so she could hand them back to me. “Did you need these?”

I sighed and shook my head. “N-no. Actually, I wanted to ask you about…”

“I think you can do better than those,” she said, pointing to the diapers. “I’ve heard that these aren’t as absorbent as some of the other brands.”

“Oh, uh,” I quickly shoved the diapers back onto the shelf–this time avoiding an awkward fumble. “I don’t need these.”

“Potty trained already, are you?” she asked, her lips curling into a playful grin.

Her little quip helped me to center myself. I needed to be reminded that she was just another human being, like me.

Humor. Maybe that was Olly’s in?

“It seems to have taken,” I joked back.

“Besides,” she said, looking back at the diapers I had just haphazardly shoved onto the shelf, “those are size 2. You’re, at least, a size 4.”

I felt my cheeks warming. It was the weirdest thing, being embarrassed by jokes about diapers, of all things. I didn’t need or want diapers. So why were comments embarrassing me?

“I…I think I’m good on diapers, actually,” I said. It was time to put that conversation to bed and move forward.

Yet she didn’t seem as willing to let the topic go. “Oh? Got all the ones you need, do you? It’s summer now, and so you ought to have some swim diapers too.”

Are we still talking about diapers, of all things?

“Actually,” I said, hoping to just trudge forward anyway. “I wanted to…”

“What’s your name?” she asked, cutting me off.

“Oliver.” Fuck. “Olly, actually. People, uh, call me Olly.”

“Olly,” she said, smiling. “That’s cute.”

Cute? That’s not what I wanted. Olly wasn’t a cute name. Olly was a cool name. On trend. Maybe even mysterious.

I tried not to let myself get too hung up on silly things, and instead tried to double-down on the potential cool-factor of the new Olly. I pretended to notice her name tag for the first time: “And you’re, uh, Melinda, eh? That’s a pretty good name.”

She chuckled and shrugged. “I suppose.”

It felt like another strike against me. Of all the things I could’ve complimented, I chose to compliment her name? It was a wasted opportunity–the kind that an Olly shouldn’t have.

“So, really, was there something I can help you with?” she asked, taking the reins of the conversation after I missed my beat. “Or did you just come over here to blush a lot.”

Dammit. This wasn’t just going poorly, it seemed to be going spectacularly bad. This wasn’t the conversation I had in mind, and this wasn’t the impression I had wanted to make.

I took a deep breath and decided to try again. I puffed up my chest a little. Stood straighter. Tried to adopt a confident smile.

“So, look, I think you’re pretty cute and I was wondering if, uh, you’d want to go out with me sometime? Maybe we could grab a drink or…”

“What is this?” she asked, barely holding back a laugh.

“Wh-what is what?”

“This little persona you just took on.”

She had seen right through me, whether I wanted to admit that aloud or not. “What do you mean? I…I’m not…”

“Oh please,” she said. “You sound like a little boy trying to be manly in front of his daddy’s friends. It’s not working.”

“Really?” Oops. I had carelessly spilled the beans about my pathetic attempt at rebranding.

“You’re cuter when you seem more genuine,” she cooed, shrugging softly. “But maybe it’s just me. I like boys that I can take care of.”

For a moment, I felt defeated. It wasn’t me–it was her. She just wanted something that “Olly” wasn’t. She wanted a boy. Olly was a man. She wanted to take care of someone. Olly wanted to be the one taking care of his woman. We just weren’t compatible.

No, wait. Hold on…

It felt like I was jumping to the wrong conclusion. The problem wasn’t Melinda, the problem was the concept of Olly. Melinda didn’t give a shit about Olly–she could see the inner Oliver, and that was what she wanted. And I could be Oliver. Easily. It was probably the thing I knew how to do best.

“I would like to get a drink with you sometime,” she continued. “But only if you promise to be yourself.”

I nodded. “Of course.”

She had seized control of the situation. RIP, Olly. You were a good–if not impossible–concept.

“Are you busy tonight?” she asked.

I shook my head. “Nope.”

“Good, me neither. I get out of work at 6. Do you know Pablo’s? The bar over on 12th? We could…”

“Oh, well, I’m not 21 yet, so…”

She giggled again, shaking her head. “Aw, poor baby. Well there’s plenty of other options. Coffee, maybe? There’s that place on Market Street. Gatsby’s?”

“Yeah,” I said. “That works for me.”

“I could meet you there at 6:30?”

“Perfect.”

“Excellent,” she said with a wry smile.

In a flash, she grabbed the package of diapers off the shelf again and thrust them into my hands. “Here,” she said, before starting to walk away. “Just in case you need them.”

It was a joke, I think.

***

Olly, as I imagined him, might have been dead. But that didn’t mean that I was stuck with the same old shy pushover that Oliver had been for the last 20 years.

Perhaps I had been thinking too big. A complete rebranding was simply too much to take on at once. What if the smarter strategy had been to make small incremental changes? I’d change small things, and see what worked and what didn’t. Overtime, the little successful changes would add up and, eventually, I’d find myself at the new and improved Olly.

I wished I had more time to devote to that process before that evening's coffee-date with Melinda, but there wasn’t much that could be done about it. Instead, I pinpointed the area I wanted to focus on for the evening: confidence. I kept it intentionally vague as to not overwhelm myself with a strict code that I had to follow with my words and body language. I simply wanted to use the word as a mantra.

Confidence.

What would a confident person say or do? How would a confident person react to the things she asked? I’d just keep rolling that word around in my head, without setting expectations for myself, and hope for the best.

She had confidence in spades. She was already waiting for me at the entrance to Gatsby’s when I strolled up the street. She was wearing the same tight black pants and white top she had been wearing when I saw her at the store earlier. A uniform, or at least conformity with a dress code, I assumed. It looked as if she had walked right out of work and straight to the coffee shop–which is probably exactly what had happened.

Did she not care about what she was wearing? Or did I just seem like someone who wasn’t worth getting dressed up for when it came to a date?

My confusion about her outfit did leave me a little flustered by the time we were face to face, but I did my best to shake it off and move forward.

Remember: Confidence.

“Hey,” I said. “It’s good to see you again.”

“Likewise,” she said. “And look at this dapper ensemble.”

I blushed a little, having not expected her to call out the work I had done to look presentable. My best pants. My favorite button-up. Product in my hair. Admittedly, I thought I looked pretty good. It might have been the most effort I had ever put into my appearance. For her to bring attention to it felt simultaneously vindicating and humiliating. Was it obvious that I was trying too hard?

“Shall we get a seat?” I asked, opening the door for her.

She strolled past me, a radiant smile on her face. She looked genuinely happy to be here. Which I had some conflicted feelings about. She was beautiful and charming and I had no doubt that she could have any man she wanted. So why was she single? Was she single? And why had she agreed to go out with me now, and why did she seem to be so pleased about it?

Confidence. It was foolish to question such things. She was allowed to have her own reasons. She chose to be here with me, and it was best to leave it at that.

We ordered some coffee and took a seat at a quiet booth in the corner. I thought that I had caught a whiff of her as we were walking to the table, but I had written it off as a scent coming from somewhere else. But I caught it again at the table, and it was stronger.

I laughed out loud when I suddenly realized what it was.

“What’s so funny?” she asked.

“I was smelling baby powder,” I said. “And it was the weirdest thing, because I couldn’t figure out where it was coming from. But then I remembered that you work in the baby section of your store.”

“Ah yes,” she said. “An occupational hazard.”

It could’ve been nothing–maybe I was just seeing what I wanted to see–but I swore her cheeks had gotten a little rosey as she said that. It was one thing to show up on a date in your work clothes. But perhaps smelling like work was a different animal–depending on the nature of the job.

“Speaking of, uh, occupations,” I said, sticking to the theme of confidence and keeping the conversation going, “do you like your job?”

Her face lit up, and she seemed to have quickly recovered from her momentary embarrassment. “You know, when people find out that you work retail, they usually just assume that you loathe it.”

I nodded. I didn’t want to say it aloud, but that was certainly my assumption.

“But I enjoy it. I like helping people. Parents, in particular.”

“Ah,” I said. “So you like working in the baby department?”

“Love it.”

“Do you have any children of your own?”

“No…”

“Do you want children?”

She grinned. “Are you offering?”

“Well…n-no…”

“I’m teasing,” she said, laughing to herself. “You’re quite easy to fluster.”

“S-sorry…”

“Don’t apologize for that,” she said. “It's an endearing quality. I appreciate earnestness.”

It was at that time that our names were called for our coffee. I offered to grab hers as well, and I used the short walk to the counter and back to take another deep breath. Confidence. I didn’t think I was doing too bad thus far. It could be better. But it could definitely be worse.

She wasted no time in jumping back into the conversation when I sat down again, our coffees now dispersed: “I like babies. Really, the whole concept of motherhood and maternity. I just like the idea of taking care of someone who can’t take care of themself.”

“That makes sense,” I said, nodding.

“Do you want children?” she asked.

“It feels a bit too far in my future for me to think about right now,” I replied. “I should finish college. Get a job. Get a partner. Get married. There’s just too much that has to happen first.”

She nodded politely.

“Besides,” I continued. “I feel like I’m kind of squandering my youth, you know? I should probably start trying to make the most of that before I think about growing up.”

“Now that’s interesting,” she said, leaning over the table slightly. Her curvy chest landed on the table top in front of her, as if being offered up like a meal. “Tell me more about that.”

“Oh, I don’t know..,” I said, blushing a little while throwing out a faux-laugh to cover up the anxiety I was feeling for having opened up that can of worms.

She shrugged. “You shouldn’t be embarrassed about it.”

“I just wish I had been more outgoing. More social. Chattier.”

She nodded attentively, seeming to hang on my every word. It put me at ease, and I found myself opening the worm-can.

“I’ve been trying to, uh, reinvent myself lately,” I found myself saying. “A rebranding, of sorts. I don’t think I need to be, like, a better person. Just a different one. One who fits in better with the world.”

“I see,” she said, sitting back into her chair again and taking a long sip of her steaming coffee. But what if you’re wrong?”

“Wrong? About what?”

“I respect what you’re trying to do, but maybe you’re looking at it the wrong way. You’re assuming that it’s you who needs to fit in with the rest of the world. But wouldn’t it be better if you got to be who you truly wanted to be, in a space where you already fit in?”

It was a good point, and certainly food for future thought. But her suggestion felt far too big, and too contrary to my efforts at rebranding.

“If you felt like you didn’t have to conform to the rest of society,” she continued, “who would you be?”

“This is an awfully deep conversation for a first date,” I said. She’d interpret ‘first date’ as my first date with her, when I actually meant that it was my first date ever.

Maybe these were the types of things people talked about on a first date?

She shrugged. “Just asking the more interesting questions. Would you rather I ask your favorite color?”

Her question seemed a little condescending, but I took the bait anyway: “Well that’s easier to answer. Blue.”

She laughed. “Would you like it if I tossed you a few more easy questions?”

I had no idea if she was being serious, just joking, or if she was simply making fun of me.

But I played along, hoping that I could at least score some points for being a good sport. “That’s a good idea.”

“Do you like when people cut up your food for you?”

Now she was being condescending. Right? There was no way that this was an honest question. I thought back to her gentle ribbing about the pack of diapers at the store. What was it about me that seemed to warrant these infantile comparisons?

“N-no,” I said. But, in an effort to keep up the appearance of being in on the joke, I added: “But maybe I’m missing out?”

“You’d be surprised how much better life could be when you let someone else take care of the little things.”

That seemed to be the point where I broke. “I have to be honest with you, Melinda. I’m not sure I know what we’re talking about anymore.”

“Admittedly, I could probably stand to be a little more blunt,” she said, smiling. “But you seem like a nice boy–albeit, a nice boy in the midst of an identity crisis. And while I’m having fun playing around with that, I worry that we’re not on the same page.”

“No?” While I wasn’t completely sure what she meant by that, I still found it to be heartbreaking.

“If I’m being honest,” she continued, “and one should always be honest about this sort of thing–I think I’m looking for a very specific kind of person. And I thought you’d be that person, you know? But…if you’re not even sure who you are, I’m wondering if I should let you figure that out first, you know? I’d hate to be an influence on that sort of thing…”

It was logic vs. desire. Logically, I knew that she was right.

But that’s not what I wanted. And, too, I didn’t think that was what she wanted either.

“Well…” I said, already feeling myself cede more control to her. “Could you tell me more about what you want?”

The smile on her face was either genuine happiness or just plain devilish. Both were also possible. I suspected that I had fallen right into her clutches.

“Shall I be blunt?” she asked. She continued without pause, suggesting that she had only asked herself. “I want to take care of someone else.”

“A child,” I said, nodding. It checked out with everything else she had said to me thus far. “It does sound like you really want a baby.”

She bit her bottom lip. I could only speculate what that meant. Was I completely right? Or had I misread her hints.

“I do want a baby,” she said.

“Right,” I said, feeling like I had successfully cracked the case. “Like I said, I just don’t think I’m at a place where I’m really thinking about having kids or anything.”

“Oh,” she said, “I’m not looking for someone to be a father.”

“Okay, good,” I replied, laughing. “So then…”

“I’m looking to make someone my baby.”

“I have no idea what you mean by that.”

“Clearly, I’m not being blunt enough,” she said. “Allow me to try again: I want to find a cute young man, strip him of his adult clothes, and stick him in a diaper. I want to feed him a bottle and give him a bath. I want him to suckle on my tits. I want him to make dirty messes in his pants that I, then, have to clean up.”

Her words hit me all at once, only to get stuck in the forefront of my mind. I began to slowly process what she had said, letting the strangeness of her desires wash over me.

“Oh,” I finally said. “That’s…interesting.”

She seemed undeterred by my hesitation and moved to fill the void left by my silence: “I thought you were a good candidate. That shy and boyish demeanor? That look in your eyes like you’d do anything for a pretty girl? I mean, sure sure, you’re putting in the work to be new and improved. But, uh, how’s that working out for you?”

“I, um, it’s…a work in progress.”

“Well, I certainly wouldn’t want to be the person standing in the way of you being who you want to be.”

I twitched a little, feeling as if she was leaving some bait out for me. It was as if she was not only trying to prove that my efforts at rebranding were worthless, but that I was actually so submissive that I could be convinced to act like a baby for her.

The thing was, that didn’t sound like the worst thing in the world. I didn’t quite get it–never had I even considered putting on a…diaper. But somewhere, in the midst of all that strange kinky fantasy of hers, was a more basic concept that I found desirable: dependency. She didn’t want someone to be the cool and self-assured alpha. She actually wanted the person I had always been–the sheepish push-over. The boy who left his direction up to those around him. The timid people-pleaser.

And so, as weird as it was, it felt like something I could actually comply with. Quite easily, really. I could almost imagine myself sitting there on her lap in just a diaper. Not because I loved it–but because that’s what she’d want, and I’d just want to make her happy.

“Ah,” she said, smirking. “You’re thinking about it.”

“I guess,” I said.

“What if we finished our coffee and then walked back to my place?” she asked.

“A-and then what?”

“And then…maybe you give me a chance to show you what I’m envisioning?” she asked. “Just a trial run. A little taste to see if you like it or not. Because, otherwise, how would you know? Right? If you absolutely hate it, then you can double down on your cool new ‘Olly’ persona–bolstered with the knowledge that you now definitively know that you aren’t some…”

“...baby,” I said, finishing her thought and thinking aloud. It was a good point. A weird point, yes, but it still made sense to me. There was only one other thing left to say: “Okay.”

***

I had somehow managed to convince myself that I was still in control. It was my choice to follow her to her home. It would be my choice to play along with whatever ‘trial run’ she had in mind. It would be my choice if I wanted to put my foot down and say when enough was enough.

But, then, moments after we stepped foot in her apartment and the door closed: “Take off your clothes.”

It wasn’t a request, it was a command. There was no space left for discussion, and I had only two options: comply or don’t. Did I already need to put my foot down?

I opened my mouth: “But…”

“It’s as simple as this,” she said, crossing her arms in front of her. “Strip off all of your clothes for me, or walk right back out that door.”

That hardly seemed simple to me. Had I known this was what was expected of me within seconds of getting to her apartment, I might not have come in the first place. Not to mention that stripping nude in front of someone I barely knew–when I had never stripped nude for anyone before–was far from simple.

So, it was either taking my clothes off or the door.

Huh, I guess it is kind of simple.

With a sigh, I stepped out of my shoes before grabbing my shirt and pulling it over my head.

“Good boy,” she cooed, summoning warmth to my cheeks as a wave of humiliation washed over me.

I wouldn’t say that I was convinced, but I at least told myself that this was just for the sake of experimentation. I’d play along for a little bit. But soon–any moment now–I’d eventually put my foot down.

I unfastened my pants and wriggled out of them, adding them to the pile with my discarded shirt, undershirt, shoes and socks. Now I stood in her living room before her in just my green boxer-briefs. I paused, waiting to see if this was sufficient.

“Everything must come off,” she said. “Including your little underpants.”

I opened my mouth to protest, but thought better of it. The rules had been clearly defined: Comply or leave. With a deep breath, I shoved my underwear down my thighs, letting them fall the rest of the way once they reached my knees.

“Very good,” she said. “Now, then, let’s see what we’re working with.”

She stepped closer to me, bending over slightly so that she could take a closer look at my flaccid penis, dangling between my legs.

“You’re not working with very much here,” she said with a shrug. “I mean, don’t get me wrong, it’s good for my purposes. It’s the perfect size for a big baby. But for the cool ladies-man that you want to be? Well…good luck, I guess.”

I had a lot of anxieties about potential shortcomings, and yet the size of my manhood had never really been one of them. Perhaps it was just the lack of context–I had little knowledge of what was considered ‘big’ or ‘small.’ I just had what I had, and I assumed–hoped, really–that it would’ve been enough.

Her observation came as a crushing blow to my ego. ‘Olly’ had been shot and he was bleeding out. This was probably right where she wanted him to be too, since ‘Oliver’ was now seeking any lick of praise that he could get.

“Come with me,” she said, walking across the living room to a hallway. I took only a single step before she turned around and held out a hand to stop me. “Hold up. No baby of mine is going to think that he can just walk around like a big boy.”

What was supposing I did, then? “So…what do you want me to…”

“On your hands and knees, honey. Babies crawl.”

I could have protested, but what would be the point? I either continued to comply, or I left.

Except, the thing was, the longer I complied–the more I followed along with her surreal directions–the harder it’d be to just stop. Well, I’ve already gone this far…

I slowly got down onto my knees before letting my upper body arch over onto the ground so that my palms were now down on her carpet as well. I couldn’t even remember the last time I had crawled on my hands and knees. Certainly not since I was a little boy. An actual little boy.

I began to crawl. There are some things your body never forgets how to do, with crawling seeming to be one of them. It was easy. Effortless, even.

She stayed in place. Instead of leading me, she let me crawl ahead of her. I blindly made my way down her hallway as she walked behind me. I was completely exposed and vulnerable. I could only imagine her view–my bottom shifting back and forth as I trudged forward, my cock still hanging down and bobbing about.

“That door on your left,” she said.

My brain a little fried from the humiliation, I started to turn towards the right without thinking about it.

“Your other left, sweetheart. Gosh, you poor little thing–you don’t even know left from right. I swore that they taught that in kindergarten.”

It was an embarrassing mistake to have made, leaving myself open for another cruel shot. ‘Olly’ was on his deathbed now.

I’d say that I didn’t know what I was expecting, except that I wasn’t even thinking about where I was crawling to. There was so much to think about while just crawling that I had no consideration for what was coming next.

But this? Even if I had put an iota of thought into where I was crawling, I doubted I would’ve thought of this.

“I…thought you didn’t have a baby,” I said.

“Well, I don’t,” she said from behind me. “Not yet.”

But this was a complete nursery. A completely finished, well-stocked nursery. Crib, changing table, high-chair, playpen. Shelves of diapers and packages of wipes. A toy box, overloaded with stuffed animals. A stack of coloring books and a box of crayons. Infantile clothing hanging from hooks and hangers.

A second, more thorough, look detected the detail that I missed on my first scan: Everything in this room–the furniture, the clothing, the diapers–was far too big for an actual baby.

“It’s all for you,” she said. “Whether that be for just today or…however long you choose to stay.”

Just when I thought I had an inkling of an idea as to what I was getting into, she turned everything up to 11.

“I think we start at the most obvious point,” she said. “A baby has to have their diaper, right?”

“You’re only making me wear a diaper?” I asked. “Right?”

“As opposed to…?”

“Uhm, using a diaper?”

She laughed. “Oh, darling, don’t you know anything about babies? They only use their diapers. And so, once I get you into one, there’ll be no potties for you.”

‘Diaper’ was an embarrassing word to hear. ‘Potties’ might have been worse–a word not only rich with juvenile energy, but one that implied a restriction. ‘Potties’ were forbidden places for babies.

“I can just hold it,” I said, more to myself than to her. I was kicking myself for not having used the restroom at the coffee shop before we left. Especially considering the way that coffee usually worked its way right through me.

“You can do whatever you’d like,” she said, shrugging. “But you won’t be using the potty while in my care.”

“And, uh, how long will I be in your care?”

“Until you’ve had enough,” she said, smiling.

The answer should have carried a feeling of relief with it–the fact that I could just walk away from this at any point was exactly what I would have wanted. Instead, I found her answer to be a little concerning. She had such confidence that this wasn’t going to be a waste of time. How could she be so sure that I wouldn’t just walk away right now?

Probably because she knew me better than I did. She knew ‘Oliver,’ and she could read him like a book.

‘Oliver’ was going to like this.

When I woke up this morning, I had absolutely no idea where this day would have taken me. Even if I were to travel back in time just a few hours to tell myself that I’d be lying down on a large table while my crush put me in a diaper, I’d have punched myself in the face and called me a liar.

But she was sliding a diaper under me and feeding the front of it through my open legs. This was actually happening.

“This might feel a little strange at first,” she said. “But I suspect you’ll acclimate to it very quickly.”

“You sound sure about that.”

“Mommy knows best.”

I felt my cheeks redden. Mommy. There was something about that word–something about the role–that triggered something deep inside me. Fuck. Yeah, I think I wanted that. I wanted…Mommy.

“H-have there been others?” I asked. “Other…babies?”

“Here and there,” she said, shrugging. “There’s an awful lot of little boys and girls who would want to be my baby, you know? So I can afford to be a little pickier. But I’ve fed a few babies some bottles. Given a few baths. Changed plenty of diapers. Now? I think I’m looking for my forever-baby.”

“I-I don’t know if I’m…”

She laughed, placing a finger over my lips to silence me. “You needn’t worry yourself about what you could be. You should just focus on right now.”

“Yeah.” It was sound advice.

“Do you like your diaper?” she asked, taping it up.

I looked down between my legs, realizing I hadn’t paid much attention when she pulled it form the shelf earlier. It’d be an obvious observation, but one that was worth stating anyway: It was large and thick–much bigger than I had imagined it’d be. It was also bright pink, with balloon and star shapes randomly printed across the plastic shell.

“P-pink?”

“You know, it’s only ever the little boys who care about such things. Put a little girl in a blue diaper? They don’t think twice. But you put a boy in a pink diaper, and he thinks his little pee-pee is going to fall off.”

I blushed, feeling especially called out.

“I like pink diapers because I think they’re cute,” she said. “They don’t mean anything beyond that. Unless you want them to. Do you want to be a little girl, Oliver? Olivia?”

“I…uhm…”

“Maybe that’s an angle you haven’t considered for your little rebranding,” she said, shrugging. “You could be little Olivia. Grow out your hair and put it in pigtails? Little dresses? Maybe some frilly pink panties that we slip over your diaper?”

My cheeks felt like they were on fire. She was right–I had never considered such a possibility in my rebranding efforts. I couldn’t devote much bandwidth to it now. But, rest assured, I’d be coming back to that later.

“We’re getting ahead of ourselves, of course,” she continued. “Baby steps–pun intended. What do you think of your first diaper?”

“It’s…big.”

“That’s a very good answer,” she giggled. “And the best I could expect from a baby. You know something? I think I have the answer to your little identity crisis.”

It was hard to explain, but I found myself feeling quite…docile. Not to say that I ever felt especially excitable or aggressive. But I was in her hands now, and it felt more comfortable than I expected it to. For her, I could be malleable. And so I just idly rested atop the changing table, the new thick diaper between my legs, and listened.

“‘Olly’ isn’t the cool cat you wanted him to be. But ‘Olly’ isn’t the same person as Oliver either. Oliver, from the sound of it, is timid, right? Uncomfortable in his own skin. But ‘Olly?’ Olly does know who he is, and he’s accepted it. Olly is a little boy–or whatever he wishes to be–who needs to be taken care of. He’s accepted that. He’s embraced it. He loves it. And that is who Olly could be.”

Ridiculous.

Olly isn’t a…

I’m not a…

Her hand cupped the bottom of the diaper, and she ran it up through my legs and over the front of the diaper. I shuddered, unprepared for what I was feeling. Humiliation. But also pleasure. Her hand was so close to my skin, yet there was so much crinkly padding between us.

I moaned as I felt my cock begin to wake from its humiliated slumber.

“Oh, what’s this?” she cooed, stroking the diaper. “Careful now, once you show Mommy how much you like your diapers, it gets harder to go without them.”

“Mommy?” It was posed as a question, but I was actually just getting a feel for saying the word aloud. My birth-mother had never been a ‘Mommy.’ She was Mom. Mother. Ma’am. But never just ‘Mommy.’

I liked saying it. It had a good ring to it.

I said it again, losing the questioning tone: “Mommy.”

“Yes,” she said, leaning in closer to me. “That’s right. I could be Mommy for you. Wouldn’t that be nice?”

My head was cluttered with thoughts and questions. My mouth opened as a spigot, unsure of what would come pouring out first.

“What next?”

“I was going to put a onesie on you,” she said. “Maybe feed you a bottle?”

“And after that?”

“You haven’t gone to the bathroom in a while,” she said, still rubbing the front of my diaper. “Your cheeks will get quite red, and you won’t know how to tell me that you need to make potty in your diaper. And you’ll be tempted to ask if you can use the bathroom, but you’ll already know the answer. So maybe you’ll tell me that you need to potty, just to see what I say–and I’ll assure you that it’s okay to go in your pants. Or, maybe you’ll surprise me–and yourself–by just using your diaper without saying anything. Maybe, then, you’ll tell me that you need to be changed. Perhaps I’ll discover it for myself, when I feel your saggy and bloated diaper for myself. And then, of course, I change you into a fresh diaper.”

I swallowed hard. That was quite specific. She’s probably been there before.

I opened my mouth again, the spigot still running.

“My apartment…”

“Move out,” she said. “A baby should stay in his nursery.”

“But, my job…”

“Quit. I’ll take care of you.”

Goddamn. It sounded so incredibly implausible. How would that even work? I’d just subject myself to being a full-time baby? For…a few months? Years? Forever? She’d support us, working in the infants department of the local retail store?

Stop. It wasn’t the new ‘Olly’s’ job to think about that sort of thing. That was for Mommy to think about.

“You’d…take care of me?”

She continued massaging me through the diaper, squeezing little moans out from me as she went.

“Of course,” she said. “Anything my baby needs, my baby would get. Did you piddle in your diaper? Mommy will clean you. Did you make a stinky poopy in your diaper? Mommy would wipe you all up. Is baby hungry? I’ve got bottles and baby food. I’m not even opposed to breastfeeding.”

“W-would you…unnh…fuck me?”

She giggled as the speed at which she stroked my diaper increased. “Oh, heavens no, Olly. Mommy’s pussy isn’t for babies. I’ll be sure to milk you frequently, of course. But if you were a virgin before…well, that’s not going to change. Ever.”

I came at that moment. That could have been seen as just coincidence. Or, it could have–and likely was–seen as a direct response to what she had just said to me.

I’d rather not say which of the two it was.

My eyes rolled back and I moaned loudly, back arched as I thrust my thick diaper into her palm. Everything went fuzzy as I felt myself collapsing back on the changing table from whatever dimension I had just briefly visited. I could feel my c*m in my diaper–the warm goo had seeped and dripped downward, rolling down into the diaper’s padding. I’d be wearing that now–for however long I stayed in this diaper.

“That’s a good boy,” she said. “A very, very, good boy.”

“Th-thank you, Mommy.”

I was still in a haze–one that I suspected I’d be in for a while. Just hours ago, I was approaching Melinda in the store. Now, she was making me squirt inside of a diaper in her oversized nursery. Nothing made sense anymore, and the future was completely unseeable. Would I just go back home later? Go to bed, like I always did? Wake up in the morning and go to work?

Where did our paths cross again? Perhaps this night was a weird one-off. For her, I was another notch on her crib. For me, she was the catalyst for an entirely new Olly–whatever shape or form that took.

Or…

“I…I’m a little hungry,” I said.

“I could get you a bottle.”

I nodded.

“Let’s get you off of this table first. And into some clothes.”

Moments later, the haze began to finally subside. I was kneeling in the large playpen, a smattering of infantile toys and stuffed animals around me. I was still in my thick, and sticky, diaper, but I was also wearing a onesie–green and blue with a cartoon dinosaur printed on the front of it. Melinda had left the room to fix me up a bottle. A bottle of what? I didn’t even ask.

This is that moment. That moment I realize I’m in over my head and that I need to go home and really consider my life choices. The moment where I sigh and begin to muster the courage to stand up, and step out of the playpen so I can tell Melinda that I should be on my way.

Rather, it should be that moment. But it’s not. She was right. Melinda–Mommy–was right about everything. Nothing ever felt more right than being in this playpen, dressed like a giant baby. Nothing had ever felt better than being made to cream my diaper.

And she had been right about Olly. I wasn’t completely wrong–Olly was more confident than Oliver ever was. He was just sure about different things.

The long term logistics of whatever would come next seemed nightmarish. I decided to put off that worry for later. Besides, wasn’t that Mommy’s job?

First things first. It’s been a while since I had gone to the bathroom, and I was aching for release. I wondered how long it would take for Mommy to notice I had used my diaper. I wouldn’t tell her–I wanted her to discover it for herself. I wanted her to have to check my diaper.

I grunted and pushed, letting my body empty whatever it needed to into my diaper.

My rebranding was complete. Olly had finally arrived.