Sissy's First Date: Chapter 3

Pushing out my lower lip, I closed my eyes and waited for the dampness of Becca’s lipstick to grace the delicate edges of my mouth. An electric shiver ran down my spine as the soft, chalky texture made contact. I was forced to hold back a gasp, not wanting to disrupt Becca’s work with a momentary oral spasm. Why did this all feel so good?! 

The answer, of course, was sitting right in front of me doing my makeup. I gingerly opened my eyelids, my heart throbbing as I took notice of Becca’s expert focus. Her gaze was so intense that it made me feel almost inanimate as if she were applying makeup to a doll. And yet, the expression behind her eyes was simultaneously warm and inviting, breathing life into my young, sissy soul. It was a startling dichotomy of being that left me as little more than putty in her soft, well-manicured hands. 

“Oh, yes. This is definitely your color,” remarked Becca, her toothy smile growing as she rounded the left corner of my lips, ensuring no speck of my natural lip color was showing. Her words filled me with exhilaration, feeding my desire to see my reflection now that Becca’s handiwork was involved. 

When Becca pulled the lipstick away from my mouth, though, she didn’t reach for her phone to show me my painted lips. Instead, her hands returned to her purse, digging around the faux leather bag as she pulled out several more makeup items. Some of them I knew from my sister’s party, such as the eyeliner and blush palette, but it became abundantly clear that I knew relatively little about what went into being a girl as the list of things I didn’t recognize continued to grow. My makeover was far from over. 

“Sorry but now that your lips are done, I can’t leave the rest of your face unattended,” said Becca, using the word “sorry” rather liberally considering the cheeky grin she was sporting was anything but. Placing three fingers on my left breast, she shoved me backward until my spine was pressed up against the seat cushion, causing our Ferris Wheel carriage to sway ever so slightly as she crawled over my lap to get a better angle at my face. 

In doing so, Becca positioned her water-logged diaper over mine, smushing our squishy padding together as she settled into place. I found myself failing to suppress the gasp that echoed out of my throat, earning a devious chuckle from my frisky partner. “Aww, does that feel good, baby?” she said, wiggling her butt into my padded crotch and triggering an immediate growth spurt. My facial muscles twitched and contorted, pleasure baked into each lewd expression that my face produced. 

For Becca, this was unacceptable. She placed a firm hand on my chin, a playfully stern air suddenly surrounding her. “Hey now, I expect my canvas to remain perfectly still while I finish my work…” she said, flexing her rear atwop my diaper-clad stiffy, “...or else, there will be grave consequences.” 

I gulped hard, using every ounce of resistance housed within my body to keep my lips from quivering. How was I supposed to remain calm enough for her to put makeup on me while in such a compromising position? It was clear that Becca was setting me up for failure. My dick hardened further as my mind raced with punishment possibilities. What would she do to me if I couldn’t keep it together? Did I even want to keep it together? 

Those questions lingered in my head as Becca uncapped the goopy, black eyeliner and returned to painting my face. “Look up and relax your eyelids, baby,” she said, her instructions precise and direct. To my surprise, this request was more challenging than expected. As someone who’d only worn makeup once by force, I’d never really contemplated what an unstressed expression was for me. Up to this point, it was something that happened naturally. So to be told to hold my eyes in a relaxed way was an oddly foreign request that had me struggling to find a neutral position, something Becca had no qualms commenting on, “Cherry, darling, as much as I love seeing what your face looks like when you make pushies, I did ask you to relax.” 

No amount of makeup in the world could cover the amount of red that was coating my cheeks. My eyes darted away from Becca, an unintentional pout forming while the dominant woman across from me was, once again, more than happy to take advantage of my embarrassed and frustrated mental state. “Hehe, well, at least you’re saving me the time of applying blush,” she snickered before placing a comforting hand along the side of my face with her middle finger hovering just below my ear lobe, “Hey, just look at me. Nothing else matters.” 

Staring into Becca’s eyes, my fears melted on contact as if I’d been placed into a trance. Her bright blue corneas were like an endless ocean that I wanted nothing more than to get lost in. It was only the first date but I swore in that moment, I fell head over heels for her. If I had been standing, one of my legs would’ve kicked into the air as a strong sense of euphoria radiated all around me. “Much better,” she said, her gentle smile returning as she raised her pointer finger to my nose and booped me tenderly. 

For the next five minutes, Becca cycled through the half-dozen products she’d picked out for me. Unlike with Sarah, there was an efficiency and lack of perfectionism that created a more easy-going experience. 

Unfortunately, there was one aspect that remained unchanged and that was how itchy it was to have makeup applied. Even the abundance of horniness stemming from my diaper couldn’t keep my mind off the way her fingers and various brushes danced around my skin. Every fiber of my being wanted to scratch the entirety of my face but I knew doing so would only wreck Becca’s diligent work. Moreover, I couldn’t help but be curious as to what the final result of the makeover would be. Would I be as unrecognizable as I was when Sarah did my face? Or would it…still be me? The anticipation was somehow worse than the itching. 

“Aaaaaaand, there. I think that should do it,” said Becca, blotting the final touches of my eye shadow before sitting back on my lap and capping the lid of the cosmetic container, “Ya know, for not having your exact foundation color, I think I did a pretty bang-up job. Though, since you’re already a total cutie, most of the work was already done for me.” 

Becca’s compliment inspired the butterflies in my tummy to flutter about. Terms like cute and pretty certainly weren’t the kind of descriptors I was used to. A pleasant heat spread throughout my chest. I never wanted her to stop making me feel this special…this feminine…this loved. 

That being said, there was still that nagging thought lingering in my mind. “Um…c-can you, uh, show me?” I asked, my fingers subconsciously weaving together while the nails of my thumbs clicked together. 

“Hehehe! Of course! You must be super excited to see how pretty you look,” giggled Becca, inching herself off my lap and scooting in close so that our diapered butts were side by side. Tapping on her phone, she promptly flipped the camera around to its front-facing view and snuggled in close to ensure we’d both be in the frame. 

In the time it took for Becca’s camera display to appear, I toiled over whether it was genuine eagerness or terrifying anxiety that was spiking my heart rate. That’s why, when I was finally allowed to see my reflection, I couldn’t have been happier with how my mouth instinctually curled upward. There was no denying that I was experiencing the unadulterated joy of a femboy sissy seeing themself dolled up like a princess. Whatever anxious tension that still remained within me disappeared long before Becca snapped our first couple’s photo together. 

There were undeniably elements of my face where my inherent masculinity shined through like my square jawline and bushy eyebrows. Becca was good but she wasn’t a certified pro like Sarah was. However, those elements were largely overshadowed by naturally girly aspects that Becca strategically brought out. “I’m so jealous of your cheekbones, by the way. I know girls who would kill for those,” she said, allowing me to watch in real-time as her complement imbued my oh-so-feminine cheekbones with a rose-colored tint, “Well, baby girl, is there anything you’d like to say to me? Perhaps something that starts with a T and ends with a -hank you.” She chuckled lightly at her own joke, her infectious laughter compelling me to giggle along with her. 

“Th-thank you, Becca,” I said, unable to stop myself from stuttering at the start of my sentence. How could I not with the way Becca was looking at me? In all my life, I can’t recall a time when someone looked at me with such intense desire. It was all I could do to requite her passionate glances, rendering both of us silent. No words were needed to express how each of us was feeling. 

CREAK! 

Sadly, our Ferris Wheel ride wasn’t designed to last forever. Our eyes remained locked as the passenger car came to a complete stop, neither of us bothered by the metal cart’s fierce rattling. Nor did we notice the death glare that the Ferris Wheel operator was shooting us. “Ahem!” said the fair employee, their annoyance multiplying for every second it took us to disembark from the ride. 

“We’re moving! Hold your damn horses,” said Becca, unafraid to return the employee’s brash bitterness. With her arm around mine, she pulled us away from the ride, saying in a not-so-quiet manner, “What a total douchebag.” 

Normally, I would’ve had no issue making a similar remark, especially considering what an ass the fair employee had been. However, for some reason, my nerves shot through the roof as if the verbal confrontation would somehow result in the entire fairground population discovering my true identity. It was a vulnerability that I wasn’t used to and one that left me wishing for the power to turn invisible. My only solace came from the fact that Becca was pulling us away from the source of conflict, allowing the tension in my chest to subside with each step. I let out a haggard breath once the Ferris Wheel and its prickly operator were out of sight. 

“Jeez…sorry about that,” said Becca, letting out an equally stressed exhale. I could tell how agitated she was, even if she was desperately trying to hide it. Craving comfort as well as the intense desire to console my date, I instinctively moved toward Becca and wrapped my arms around her. I barely knew what was happening until I found my head nuzzled into the crux of her shoulder. 

My affection was reciprocated almost immediately, with Becca applying a great amount of pressure to my back as she squeezed me with all her might. A small squeak escaped my freshly painted lips, piling more blush onto my exposed face. I could feel the sense of invincibility that Becca’s presence filled me with returning in full. 

GRUMBLE! 

Embarrassingly, in the midst of our hug, my somersaulting tummy decided it was the perfect opportunity to sound off. I didn’t even realize I was hungry until the stomach-churning noise impacted my ears. “Hehe, sounds like it’s feeding time, baby girl,” she whispered into my ear while still pressing her body to mine, “Does baby want big girl food or are you just too tiny for solids?” 

The way her breath tickled my ear was more delicious than any meal I could think of. That being said, the image of being legitimately bottle-fed while in public was too much to bear, at least if that’s what Becca’s intentions were behind the “too tiny for solids” line. Not wanting to wind up letting Becca decide for me, I quickly responded, “Big girl food is fine,” only realizing a split-second later that I referred to myself as a big girl without even so much as a passing thought. 

“Hehehe! Alright, my BIG GIRL!” said Becca, refusing to let such a juicy quote go by unacknowledged. At this point, I feared my face would be permanently red by the end of this date, “Let’s head back to the vendor hall. There’s bound to be tons of big girl food options there.” Her hand planted itself on my head, patting my hair lightly so as not to mess up my delicate appearance. I smiled back at her, never wanting this date to end. 

TO BE CONTINUED…