Sissy's First Date: Chapter 2

SQUISH! SQUISH! SQUISH! 

An audible squelch accompanied every step I took as Becca and I exited the women’s room. It didn’t matter how much Becca tried to calm my nerves by saying that it was all in my head and no one could hear it. No amount of reassurance could stop my paranoia from obsessing over the soft, spongy sound. The sheer panic of it all had my heart rate through the roof. 

THROB! THROB! THROB! 

Speaking of heart rates, between the fear of being caught and the endless sexual tension between Becca and me, my blood was pumping at high speeds. This, unsurprisingly, affected the size, sensitivity, and stiffness of my genitals. Every time my swollen diaper shifted or my engorged cock twitched, I feared my buckling knees would give out. The only solace I got was from the cooling sensation that came from the chilly water that kept my boner at least somewhat in check but that was far from a consolation prize if you ask me. 

Meanwhile, walking only a few feet ahead of me was the living embodiment of confidence and grace. If I hadn’t been the one to pour a full bottle of water into her diaper, nothing about the way she composed herself would’ve ever made me guess she was padded. It begged the question in my mind: exactly how many times had she worn a diaper in public? 

“I can tell you want to ask me something,” said Becca, spinning around on her heel and walking backward in front of me.  

I must’ve been quiet for too long. Either that or she was a literal mind reader. Placing a hand on the back of my neck, my eyes instinctually shot toward Becca’s feet as I responded, “Sort of. I-I didn’t want to offend you, though.” 

“Oh, well, now you HAVE to ask,” teased Becca, planting both feet on the ground and forcing us to stop in place. It was clear this date would not be moving forward until I said what was on my mind, “And I’d better get to see your pretty eyes when you do.” 

Butterflies filled my chest before exploding out of my body. I didn’t have a mirror but I instantly envisioned myself with visible smoke rising from my circuit-fried brain. “It’s just…you seem so…comfortable. It has me wondering how often you’ve done this stuff,” I said, forcing myself to look deep into Becca’s eyes despite how warm and heavy it made my cheeks. 

“Eeeeee!” squealed Becca, catching me completely off-guard as she rushed toward me and pulled me into a hug. To say I was confused would be an understatement, something Becca must’ve sensed through my body language from how quickly she broke from her embrace, “Sorry. Sorry. It’s just…the way you blush. I just can’t get enough of it.” 

Steam had to be shooting out of my ears at a constant stream by this point. How did Becca do it? How did she know exactly what to say to ruin my composure every time? How did she make me want to die of embarrassment while simultaneously making me feel more alive than I’d ever been? Everything about her was a conundrum. 

Luckily for me, Becca must’ve taken pity on me as she quickly pivoted to a response. “To answer your question, yes. This is far from the first time I’ve worn publicly before, both on my own and with…partners,” she said, watching as my head sank a little, “Buuuuut, if it makes you feel better, you’re doing a lot better than anyone else has. Most people I’ve spent time with while padded either lie about how much they’re willing to submit or, even worse, try to take charge of the situation.” 

“And you don’t want that?” I said, struggling to wrap my head around the relationship dynamic that Becca was after. 

Thankfully, Becca was more than happy to fill me in on exactly what she expected from a partner, which in this case, just so happened to be me. “Not at all. If I wanted a dom, I could find some pig-nosed idiot to diaper me any day of the week,” she said, closing the gap between myself and her as she grabbed me by the cloth of my dress and pulled me into her chest, “No, I want a subby, sissy who will jump when I say how high. And on that front, I don’t think you have anything to worry about, my precious, little Cherry.” 

My eyes were wide and my breath was heavy as Becca whispered her expectations for me into my ear. I should’ve been running with my wet diaper tucked between my legs. Everything about Becca was firing off red warning signs in the manly ego of my brain. So…why did submitting to her sound and feel so fantastic? It was a thought that lingered in my head as Becca looped her arm through mine once again and set off toward a set of midway rides. “Now, that’s enough questions for now. Let’s get that padded butt of yours moving. Daylight’s burning and I’ve had my eyes on that Ferris Wheel since we got here,” she said, forcing me to waddle awkwardly alongside her as she led us into the heart of the fairgrounds. 

As we walked, the hyperawareness I felt toward my attire drifted away a little. My walk became more casual as I learned to sway my hips with the diaper. My back straightened up as I no longer felt the need to duck my head down and hide. My expression relaxed, allowing a genuine smile to grace my lips. If I had been alone, none of this would’ve been possible. But with Becca at my side to keep me safe, I felt… invincible. 

“Someone looks like they're starting to have some fun,” said Becca, who had been watching every microscopic change to my expression and mannerisms from the corner of her eye. I opened my mouth to say something back but found myself at a loss for words, too blushy to counter what Becca had said. In truth, she was right, something I clearly didn’t need to tell her with the way she was looking at me. 

Mercifully, it wasn’t long before we arrived at the line for the Ferris Wheel, which gave Becca something else to hook her attention on. “Good thing we got here before the rush. Last year, this line was like an hour long once evening rolled around,” she said, attempting to engage in the kind of mild chit-chat one might expect on a first date. 

The easy conversation allowed me to respond without much pressure, something that was likely Becca’s intention but she made it feel so effortless somehow. “No kidding. Though, I can’t say I’m one to balk at lines easily,” I said, recalling my recent trip to Disneyworld and the sometimes multi-hour waits that came with each ride, “Abby’s the weakling when it comes to theme parks so you’ve got nothing to worry about with m-” 

SNAP! 

“Huh?” I said, my attention snapping away mid-sentence at the flashing sound of a photo being taken on someone’s phone. This undoubtedly spiked my anxiety as noise yanked me from the private, comforting world that Becca was trying to keep me in. My head whipped back and forth, searching for the source of the snap but finding nothing. 

Of course, it didn’t take long for Becca to notice my shift in attitude. With her arm still entangled with mine, she tugged me in close to her before shifting her arm up and around my shoulder. “Doing okay, rocketman?” she said, the oddness of her sentence breaking me from my paranoia. I gave her a confused look, causing her to chuckle, “Sorry, you were spacing out so…rocketman. It’s a C-tier joke, I know.” 

A few seconds passed before the logic of her joke connected in my brain, making me feel slightly dumb for not connecting the dots sooner. I snickered both at her joke and the tiny hint of rosiness spreading across her nose, enjoying the brief role reversal. “Yeah…yeah, I’m doing great,” I said, looking deep into Becca’s eyes and sharing a moment that felt more intimate than any instance of kinky fun, “You could even say I’m…feeling out of this world.” 

“Pfffft! Oh, my Goddess! You are such a goober,” said Becca, bursting into full-on laughter. It may have been a touching scene but the joke was too good to pass up on. 

“Next!” shouted the impatient fair employee who was in charge of the Ferris Wheel, looking particularly annoyed by the fact that Becca and I were holding up the line with our lovey-dovey dorkiness. Becca’s arm broke from its hold on my shoulder as we hurried into the bottom-most passenger car. We barely had our squishy butts planted in our seats before the Ferris Wheel lurched forward, sending us up in our own private gondola. 

The fair may have been one of the most public places you could be but as soon as Becca and I were in the air, it somehow felt like we were the only ones there. Especially with how small the fair began to look the higher we ascended. “It’s such a pretty view,” I said, breaking the silence that had been building since loading onto the ride. 

“Right? If there’s one ride I make sure to do every year, it’s this one. I’ve always been a Ferris Wheel girly,” said Becca, looking incredibly cute as she cheerfully swayed from side to side a little. I thought about pointing it out to her in hopes of recreating her rosy reaction from earlier. However, I bit my tongue as I contemplated the possibility that such a taunt might escalate Becca’s desire to see me equally as embarrassed, if not more so. 

Meanwhile, as I considered the ramifications of teasing my domineering date, Becca took the restful moment as an opportunity to do a bit of touch-up work. Placing her purse in her lap, she pulled out her cell phone and a tube of lipstick and began expertly re-coating the edges of her mouth with a yummy-looking red. I stared longingly at her perfectly plush lips, I wondered how amazing it would feel to kiss them again, which we had yet to do since our night of passion at Abby’s slumber party. 

Unfortunately, when Becca caught me gawking at her as she applied the finishing touches to her lip, her mind went in a completely different direction than mine. “Aww, does someone want to play with Mommy’s lipstick?” she asked, pulling the slick, silky tube away from her mouth and inching toward me, “If you’d like, I’d be happy to doll you up a bit. I may not have Sarah’s skills but I’ve definitely been itching to take a crack at your pretty face.” 

In the end, it didn’t matter if I made Becca blush or not. She was going to press every one of my buttons until I combusted. “I-I…uh…” I stuttered, unable to put my thoughts into words. I had felt a tad thankful that Becca hadn’t forced me to try my hand at make-up before the date. I probably would’ve looked more like a clown than a girl. That being said, now that the prospect of having Becca do my make-up was on the table, I felt incredibly torn. Why did being treated like her doll make me feel so…alive? 

Fortunately, for the sake of my sanity, Becca decided such a decision was far too big for me to make. “It’s okay, Cherry-baby, Mommy knows exactly what you want. Just lean forward and let me take care of everything,” she said, her words sending my mind into a deep, Little Space.  

How could I say no to her now? Not that I even wanted to say no at all. There was no denying it now. I was a sissy, through and through. “Just don’t do anything too over the top, okay?” I said, not wanting to stand out from the crowd more than I already was. 

“Hehe, trust me, you have nothing to fear. When I’m done, no one will see you as anything other than what you are, my baby girl,” said Becca, shivers coursing throughout my entire body as she did, “Now, let's get you puckered up, buttercup.” 

TO BE CONTINUED…