Special thanks to Mr. ABDM for feedback.
At first, Bobby drove in the direction of our homes, but continuing to feel adventurous, especially with him beside me, I told him to take a different route.
So far, my plan had worked. My wet blouse clung to my chest, emphasizing the enticing curves. Soaking it had also turned the thin fabric transparent and made my cute new bra visible to Bobby.
I caught him sneaking peeks at it and giggled inside as I embraced the pleasure mounting within my diaper. Even when I didn't catch his eyes, I knew when he was looking at my breasts because he inhaled quickly and quietly each time he gazed upon my boobs nestled in the delightful diaper-style outline of my bra.
We drove into the mountains while the rain kept on past sunset. The car twisted up the winding roads as the darkness descended.
At last, we reached a deserted overlook on the side of the road, and I realized that this was where we had come when I was a kid, although the pouring rain and clouds were now obscuring our view of the city.
"Let's stop here, Bobby," I said.
I liked being alone with him in this familiar empty space. He parked the car, and, for a bit, we just listened to the pitter-patter of the droplets.
"I like your new clothes," he said, breaking our companionable silence.
"Do you like my bra?" I asked him, shyly.
"Yes."
A short, knowing, awkward silence followed.
"W-well, what I mean..." He tried to take it back.
"You're cute," I said, taking his hand to reassure him.
He looked at me and leaned in for a kiss.
"I want to see your diaper," I whispered into his ear. "Can I take off your pants?"
He nodded and leaned back the driver's seat and then kicked off his shoes.
As delicate as possible, I undid the top button and unzipped his fly. The whiteness of his diaper was very apparent in the dashboard lights. Then I pulled his pants down over his muscular thighs and away from him.
I saw his diaper, and I lost my breath. He had wet it already, and it made me happy that he no longer hesitated to show it to me in what used to be an embarrassing condition. Right then, I felt us growing closer, sharing secrets, which excited me further.
My hand approached the padding as his breaths got quicker and quicker. His body begged for my touch.
Knowing what would happen, I stopped before we made contact. I wanted to make his inevitable joy more meaningful.
"Now you can take off my skirt," I told him.
He did so with trembling hands, and then my diaper was also exposed.
"Oh my," he said, "You look so cute!"
"You're not done yet," I said.
He looked confused.
"I mean, what have your eyes been begging to see since I stepped into your car?" I added. "These."
Bobby's face flushed red as I guided his hand to my chest.
One by one, he undid the buttons on my blouse while I watched his stiffness shaking in his diaper. Even without it, I knew his fate the instant Bobby spotted my princess bra through my transparent shirt. His imagination must have been running wild since I got into his car.
He undid enough to pull away my blouse. I inhaled and exhaled for Bobby to see my breasts rise and fall in their adorable pink cups.
"Ah!" He squealed as he sputtered into his diaper, keeping his eyes on my breasts for as long as he could before collapsing back into his seat, nursing the remaining spurts into his diaper with both hands.
It moved me to joy thinking how hard it must have been for Bobby to hold it in for so long while I teased him. At least he had finally cum in his diaper when it mattered most.
"Thank you for holding that in for so long," I said, kissing his cheek.
"You make it feel incredible, Katy. Like nothing I ever felt before."
I giggled and turned to look at the back of the car, listening to the pouring rain. It soothed me. Like Bobby, I also felt my own needs swelling up inside my diaper, ready to consume me.
I asked him to collapse the backseats, so we could lie down together, and watch the droplets fall on the window of the Prius' backdoor. We held hands and basked in the clatter of the rain.
So far from anyone else, alone together.
With that in mind, it became impossible for me to hold back any longer. I began stroking the front of my diaper, wondering how he would react. At first, he didn't notice, but then I felt his body stiffen.
"Let me help you," he said.
He delighted me. I felt his strong hand displacing mine. I pictured him working out with the weights in his room.
