Sissy's First Date: Chapter 5

The small, two-seater boat bobbed and buckled as Becca and I boarded the vessel. Planting both feet on the creaky, wooden floor, I extended a hand back to Becca. “Why thank you, my dear, Cherry,” she said, adding a bit of snootiness to her tone for comedic effect. 

Playing along, I responded, “Of course, my lady,” as I helped to lower Becca into her seat. I was happy to have our happy-go-lucky energy back. My heart fluttered as I pressed my skirt to the rear of my diaper to sit, and I wasn’t certain if it was due to the overwhelming levels of girliness, the sheer amount of squishiness, or the fact that I was cozied up with Becca in a very compact space. Though, deep down, I was pretty sure it was a bit of all three. 

“Please keep your hands and feet inside the vehicle at all times. The use of flash photography is not permitted at any time. Thank you and enjoy the tunnel of love,” said the woman operating the ride, doing her best to sound enthusiastic after repeating the same phrase for the past several hours. 

BONK! 

The mechanism holding the boat in place unlatched, casting us off into open waters. It took no time at all for the boat to reach its gradual max speed as we were shoved along the slow-moving stream. Light receded from the mouth of the tunnel behind us whilst the growing darkness of the tunnel ahead and the slight breeze of air conditioning sprouted goosebumps up and down my forearms. The chilly air had me wanting to wrap an arm around Becca’s shoulder, both for warmth and romance. However, my plans were dashed as my date beat me to the punch, nestling me under her wing and squeezing me delicately into her torso. 

A sense of fuzziness transcended upon me, overwhelming me with pure femininity. How such a simple action managed to make me feel so small and effeminate I will never understand. 

Before long, the pitch-black tunnel began to illuminate as we entered the first room on our journey. Soft, ambient pop music from the 70s played overhead that paired well with the decor, which looked as though it hadn’t been updated since around the same era. Countless red and pink hearts were scattered about along the walls and strung up haphazardly, giving off the feeling that we’d been shrunken down and stuffed inside a box of conversation hearts. A minor disappointment, though I can’t say I was expecting much from a county fair attraction. 

It’s not like the ride itself was where my focus was anyway. Right now, all of my attention was being dedicated to the padded beauty seated beside me. Not wanting to appear too eager, I kept my head forward, electing to use my peripheral vision to steal glances at Becca any chance I could. From her luscious lips to the way her wavy hair curled around her ear, every inch of her being was a masterpiece. 

“Heh, ya know, you can do more than just look…if you want,” said Becca, drawing attention to the extended silence that had existed between us since our boat embarked. It took me a few seconds to process what she said, adding a smidge of extra blush to my face once her words finally clicked. This gave Becca even more of an opening to tease me at will. She leaned in closer, placing a hand on the top side of my thigh, “Aw, was my sweet baby hoping I’d make the first move? Hehe! You really are just a sissy baby gi-” 

Suddenly, a blackness far darker than the tunnel’s entrance overtook my vision. All I could feel was a surge of electricity enveloping my lips, accompanied by a foreign, yet inexplicably pleasant plushness. It was as if my mouth was pressed against two soft, wet clouds. I let out a brief, sultry moan as I squinted my eyes open, only to be greeted by Becca’s eyes a mere inch from my own. 

Mwah! 

Pulling away, I raised my hand to my mouth, unable to shake the burning tingle that lingered from our first real kiss as a couple. I was practically in shock over my own boldness. What had I just done?! “O-Oh, my Goddess! I’m sorry! I d-don’t know what came over-” was all I got out before Becca ripped my hand away from my face and smashed her kisser into mine for a second time. The tip of her tongue stabbed at the crease of my mouth, demanding to be allowed in. I obediently parted my lips and let her have her way with me orally. 

Unsurprisingly, this wasn’t the only way that Becca planned to have her way with me as the hand that she strategically positioned on my leg finally came into play. The tips of her fingers tickled my skin as she made her slow approach toward my soft, sensitive inner thigh. They pushed another moan out of me, this one much less restrained. I could feel my squelchy diaper molding around my ripening dick as it grew and made itself known. 

“Uh oh, is that for me?” cooed Becca, her lips separating from mine as she explored the rest of my face and neck with her mouth. Meanwhile, her hands were continuing to forge their own expedition as her knuckles brushed against the underside of my nappy, taunting me with anticipation. 

My entire body was radiating euphoria as we exited the floating hearts room and entered a more narrow corridor with blue-painted walls that had sparkly lights twinkling all around us. Paired alongside the slow-moving stream’s reflection, it was as if we were drifting through space together. Water rippled around the exterior of the boat with our passionate makeout session acting as an epicenter. “Mmmm! Do you hear all those yummy sloshing sounds? How’s about we make a few of those ourselves?” she said, her hand leaping off my lap and mashing itself into my pointed diaper. I would’ve screamed out in pleasure if her lips hadn’t sealed themselves to mine. 

Weakened by her touch, I let my spine go lax and leaned back in my seat. Becca was now in complete control, a thought that served to multiply my arousal. This gave Becca the green light to shift herself onto my legs, causing the boat to rock tremendously. Once she got settled into place, she leaned in and whispered next to my ear, “I’d say I’ve teased you enough for today. Don’t want my baby getting all pent up, after all.” 

“Mhmm,” I mumbled meekly, worried that I’d be too loud if I opened my mouth for even so much as a millisecond. Utilizing every ounce of strength I still possessed, I raised my arms around Becca and began caressing her hair. It was so incredibly soft. My fingers soon got lost in her locks, never wanting to leave such a silky oasis. 

Becca, however, had bigger plans for my hands. Without warning, she grabbed onto my left wrist with her free hand and pulled my hand down to her chest. The instant my open palm made contact with her spongy tit flesh, all thoughts toward resisting vanished. “Ah! S-So soft!” I stuttered, my voice echoing around the star-filled landscape. 

I was lucky to have Becca above me to press her hand to my mouth, suppressing my volume. “Shhhh! Don’t want the fun to end early, do we?” she asked, prompting me to shake my head back and forth in a flurry. This made her giggle but I didn’t care. I never wanted this to end and I didn’t care how much Becca knew that. 

The starry corridor eventually came to an end, giving way to the Tunnel of Love’s final room. It was a brightly lit cityscape that was lined wall to wall with dolls that were matched up in couples. Some dolls were doing the kind of things people often do on dates such as dancing, ice skating, and eating at a fancy restaurant. But the majority of them were simply holding hands with each other. It was definitely weird and a little creepy to have so many eyes staring at us amid our heated embrace. Thankfully, it did nothing to derail the sexy fun Becca and I were having, especially now that we were in position to take our fun to the next level. 

Bending her knees at my sides, Becca eased herself forward onto my lap and pressed her mooshy padding into mine. Unlike our first time humping diapers, I was only wearing two layers of padding. And while the added layers did make things a heck of a lot squishier, every diaper also dulled the external sensations considerably. This meant that I was defenseless as Becca’s soggy, mushy diaper butt mooshed into my nappy-swaddled cock. My reaction was instantaneous. 

“Ooh! Fuuuuuck!” I screamed with my tongue resting on my bottom lip. My feet shot upward and kicked the wooden plank in front of me, splashing water up between the boat and the wall of the river as we ebbed and weaved. I instinctively reached down and grabbed the side of the boat, only realizing that I’d let go of Becca a moment too late. 

With one hand planted on my diaper and the other struggling to cling to the fabric of my dress, Becca had nothing to support her weight as the boat continued to bounce. She attempted to shuffle off my lap so that she could steady herself better but couldn’t manage to squeeze her arm out from between my diaper and her hips before her balance was completely lost. I attempted to save her at the last second by grabbing onto her as she fell but all she ended up doing was dragging me down with her. 

“WoooOOOAH!” 

SPLASH! 

In a single, swift motion, our boat capsized, sending us both tumbling into the bed of water below. The knee-high fluid quickly swarmed around us, pouring into our diapers until they were filled to their maximum capacities and soaking each of our dresses thoroughly. I scrambled to climb to my feet, aiming to help Becca do the same. Tragically, I did not account for the increased weight of my waterlogged diaper, sending me toppling over Becca and drenching us for a second time. 

Laughing in bursts between surfacings, Becca was in complete hysterics over our damp predicament. She swung her arm at the water in front of me, splashing me with a faceful of murky liquid. “And here I thought today couldn’t get any better,” she joked as she staggered to her feet, revealing her supremely sodden pulp balloon to me. Seeing her lewd body in such a swollen nappy with her clothes hugging her form was the absolute definition of beauty. 

“You like what you see?” said Becca, peeking over her shoulder and catching me gawking. It was as if she could sense my gaze. Giggling at me as I nodded yes with my eyes wide as dinner plates, she extended her hand down and yanked me to my feet, “Fear not, I’ll give you plenty of time to see all that you want soon enough.” She punctuated her sentence by booping me on the nose, something that I couldn’t help but notice was turning into a habit. 

Leaning in close, I could already feel my body compelling me to kiss Becca again. Her lips were just too addictive. “I can’t wait,” I said tenderly, pressing my chest and sopping diapers into hers as I stared into her entrancing eyes, “But I already see everything I want to.” 

A line of red emerged across Becca’s nose and cheeks as well. I loved the way she blushed. I wouldn’t get the chance to see it for long, sadly, as she immediately moved to cover up her romantic embarrassment with a fiery kiss. 

“Hey! We’ve got a boat with no passengers over here!” shouted the woman working the Tunnel of Love, her booming voice perfectly audible from outside the dolly room. 

Becca and I snickered through the end of our kiss. “I think we should probably go,” I said, knowing that it wouldn’t be long before an awkward encounter with the boat behind us. 

“Eh, we’re getting banned for this anyway. So just kiss me, dummy,” stated Becca, ignoring the annoyance of the worker running the ride and continuing to pound her lips into mine. All the while, the only thought that kept repeating in my mind was that I couldn’t imagine anyone having a better first date than this. 

THE END.