Sissy's First Date: Chapter 1
12:55 PM. Perfect. My plan to arrive five minutes early had gone off without a hitch. And as far as I could tell, my date was nowhere in sight yet. Hehe…my date. Just thinking about the fact I was going to be going on my first date with my new girlfriend had me giddier than I’d ever been in my life. I hadn’t had much luck with women up to this point, so to land a bombshell like Becca was a dream come true. Though, I have to admit, as far as dream dates went, the floofy purple party dress with white lace trim and the pair of double-thick diapers weren’t something I had initially envisioned for myself.
It all started a few weeks ago when my twin sister, Abby, decided to host a slumber party for herself and all of her besties. Since we shared an apartment at college, I shamefully decided to stage a small viewing party for myself and set up cameras all over the house so I could catch every second of action from the comfort of my bedroom. Sadly, the only thing caught that night was me. Needless to say, the girls were far from happy with me, and I honestly can’t blame them. However, the last thing I expected was for them to turn me into their own, personal baby doll as punishment, dressing me up in the most humiliating get-up of my entire life and forcing me to do many blushy things.
And the strangest part was…I liked it. At first, I didn’t want to. In fact, I resisted my sister and her wicked friends at every turn. It wasn’t until my sister’s best friend and my deepest crush, Becca, stepped in to make the night of torturous embarrassment all worth it. Turns out, she had a thing for shortie sissy babies, and she was more than happy to prove that as we enjoyed a night of padded pleasure together. It was like having my eyes opened to a completely new and exciting world that I didn’t even know existed. At the end of the night, she bestowed me with the sissy name, Cherry, and declared that I would be her sissy cherry-boy forever, something I wasn’t about to complain about.
That being said, just because I was starting to embrace the sissy baby lifestyle that had been thrust upon me didn’t mean I was exactly keen to be seen in public in such an outfit, or anyone else besides Becca for that matter. I’d even gone as far as to sneak out of the apartment with my girly clothes tucked away in a bag so that Abby didn’t know. I was far from ready to tell her what her devious punishment had awoken in me.
Thankfully, it was a bright, sunny day outside, so Becca had paired a matching purple parasol to go with my dress; a parasol that gave me the chance to hide my face from passersby whenever the anxiety of being in public got to me. Becca really did think of everything. Eeeeeee! Just thinking about her again had me prancing in place. I quickly restrained myself, hoping to avoid attracting any unwanted attention.
“That was a cute, little dance you were doing, Cherry. Was that for me?” said a voice that sounded all too familiar. Unsurprisingly, my face turned bright red as Becca leaned forward and lifted my parasol before sticking her face under and smiling at me in such a way that my big, dumb heart instantly melted. She looked so beautiful in her floral sundress, topped with a sun hat to match and bright red lipstick that made her kissably plush lips stand out. She also had a large diaper bag noticeably tucked under one of her arms with the strap over her shoulder. Almost immediately, I felt the blood in my body center around my crotch, filling my body with stimulating sensations. If it weren’t for the double diapers shielding my shame, my hard-on would’ve been on full display. “You…you look…wow,” I said, unable to blink or turn my eyes away from Becca’s beauty. I was so horny and flustered and head over heels to have someone willing to dress up for me like this. I had no idea what else to say.
Becca, on the other hand, was more than happy to steer the conversation. “Hehe! Thank you, Cherry, though I must say you’re giving me some stiff competition,” she said, making me feel like a doll as she looked me up and down seductively, “You must be so excited. This is your first date ever, yeah? Don’t worry, I promise to show you the absolute bestest time. Let’s head in, my lovely, little lolita.”
Becca punctuated her sentence by pinching my cheek lightly before looping her arms around mine and ushering me toward the entrance to the county fair, which was two towns over from where we went to college. That fact unfortunately did not prevent my heart from fluttering with every step. Normally, a local fair like this was the last place I’d want to be. They were hot, full of screaming kids, and almost always smelled like manure. But today, with a parasol and dress to keep me cool and Becca at my side, I didn’t care if she wanted to take me to the surface of the sun. I’d buy some SPF 1,000,000 and rocket my ass into space in a heartbeat for her.
Unfortunately, while the dress was certainly breezy, the diapers were another story. I’d only been standing outside for ten minutes or so and I could feel my undercarriage starting to broil. Mercifully, the line for tickets to the fair was super short and we were inside in a matter of minutes. Wiping the sweat off my brow with my free hand, I spotted a drink stand near the entrance that was calling my name. Some ice-cold water would keep my internal temperature in check, as well as help with the heat that double diapers brought with them. “Hey, do you mind if I grab a water real quick?” I asked, gesturing toward the stand.
“Oh, we don’t need to waste money on overpriced waters. I packed you some juice for just such an…occasion,” said Becca, her words petering off as she clocked the dejected look on my face, along with the beads of sweat that accompanied it. The amount of pity contained within her stare made me feel weak in the knees. I wanted to tell her that I’d be okay but before I got the chance, she tugged me toward the drink stand, her nervous expression shifting to an opportunistic one, “Hello, sir. Two large waters, please.”
“Certainly!” said the man working the drink stand as he opened the refrigerator behind him and snatched two giant water bottles from the rack. Oh, how I wanted to dive across the counter and shove myself in that fridge. Of course, I would never do such a thing but the thought was there all the way up until the man was passing the twin bottles off to Becca in exchange for her credit card. It was embarrassing to let her pay for me like this but I was instructed before the date began not to even dream of bringing my wallet. Luckily, the transaction was painlessly over seconds after it started, “You ladies have yourselves a nice day.”
Nodding to the man without hesitation, Becca responded, “Same to you,” allowing him to continue believing I was, indeed, one of the “ladies.” Heck, with the way I was dressed, I might as well be. Other than the hint of masculinity in my facial features and my deep voice, I doubt anyone would be able to tell I was a guy so long as I stuck to Becca and kept my mouth shut.
As Becca and I departed from the drink stand, I reached over for one of the water bottles, only for Becca to pull away at the last second before I could wrap my fingers around the cap and bottleneck. “Ah, ah, ah! You’ll get this soon enough. Follow me, Cherry,” she said seductively, causing me to swoon as she lured me toward the nearest set of restrooms. To my surprise and slight horror, she beelined directly to the women’s side.
“W-Wait, are you sure it’s okay for me to go…in there?” I asked anxiously, planting both feet on the cement ground as I stopped in the middle of the bathroom doorway. I may have just contemplated how well my girlish appearance passed but that didn’t mean I was ready to put my new look to the ultimate test yet, “What if, you know, someone sees me?”
Snickering as she playfully rolled her eyes, Becca clearly didn’t share my concerns. “Cherry, you look like a cupcake topper and you’re as sweet as one too. And if anyone says otherwise, I’ll bop ‘em in the nose,” she said, shadowboxing a couple of times and forcing several giggles out of me both from her silly behavior and her gushy compliments.
Part of me was still on edge as I let Becca lead me into the girl’s room. I kept my eyes trained on the black and white tile floor, too afraid of what might happen if I looked anyone in the eye. Fortunately, there were several empty stalls open, allowing Becca to pull us into one of the larger ones with a baby changing area near the back of the bathroom. “You’re not gonna make me lay down on that thing, right?” I whispered, keeping my voice low to avoid detection as I pointed to the plastic, fold-down changing table.
“Huh? Oh, pfffft! Nah, as fun as that would be, I think my little sissy is just a little too big for that. Don’t worry, though, I have something much more fun planned,” said Becca, approaching me and, without warning, lifting the skirt of my dress high. I instinctually moved to stuff it back down, only for her to swat my hands away effortlessly, “Now, now, don’t be fussy. Unless you want me to raw up your bottom right here and now.” Her stern voice and vague threat of punishment were enough to awaken my little buddy again, which was desperately wiggling around in my diapers for more space to grow.
Closing my eyes, I was too mortified to watch as she ogled my diaper. It didn’t matter that she knew I was wearing it or that she’d even been the one to pick them out for me. It was still me standing before an unbelievably attractive woman in a diaper, something I don’t think I’d ever be used to. Moreover, I braced myself for the impact I was certain was coming.
Crinkle!
“Eeeep!” I squeaked involuntarily as her palm pressed the exact spot where my stiffy was. I felt light-headed as she reached up and pulled the front of my diaper open. What on Earth was she doing? She wasn’t about to pleasure me in a public bathroom. After spending a night with her at my sister’s slumber party, I wasn’t sure exactly which cards were off the table with Becca. However, the next thing I felt wasn’t a warm hand wrapping itself around my cock. She had something much frostier in mind for my diaper.
SPLASH!
“GASP!”
All air evacuated my lungs as Becca quickly uncapped the recently purchased water and proceeded to pour its contents into my thirsty diaper. “Nothing feels better on a hot day than an ice-cold diaper. Trust me,” she said, continuing to load my diaper with the brisk beverage until the entire bottle was emptied. By the time she yanked the bottle from my diaper, the water had overtaken both the front and back of my innermost diaper, widening my stance ever so slightly.
“There you go, all nice and wet,” said Becca, lowering the skirt of my dress and leaning forward to present me with a kiss on the cheek. I raised my hand to meet the lipstick stain she left behind, practically feeling the love in her heart radiating off of it. I wasn’t sure this day could get any better. That was until she passed the second water bottle to me before lifting her dress and showing off her own pair of pristine padding, “My turn, Cherry-baby. And you better not spill a single drop.”
I gulped hard as my eyes absorbed every inch of her lude, partially nude body. I was very wrong. This day was just going to do nothing but get infinitely better and Becca was going to make sure of it.
TO BE CONTINUED…