My Diapered Boyfriend Ch. 05

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.

"Go slower," I told him, so he did.

I wanted to feel every stroke of his hand while the sky gushed water from the darkness onto the glass above our heads.

I felt my body starting to convulse from the overwhelming joy Bobby was sending into my diaper. I turned my head to see his, and it was obvious that his bulge had returned. Just as I had done in my fantasy back at the hotel, I played with one of his tapes till it came loose.

"What are you doing?" He asked, continuing to send me to the edge.

"I want to make love to you," I said. "I need to get into your diaper."

"What?" He stopped dead and stared at me.

My admission surprised even me, but I realized I had been building up to this wish for a while.

"I want to make love to you, Bobby," I repeated.

He inched away from me. "I can't," he said.

"Because you'll cum too soon?"

"Because I'll cum in my diaper before I even see your breasts. You know what happens."

I did not back down and fully embraced my feelings.

"I don't care how many times you cum in your diaper," I said, "I just want to be with you. That's all that matters."

He still looked down, so I took his hand and guided it to my chest.

"Touch my breast," I told him. "Go ahead."

He explored my softness, my warmth, and the delicate fabric of the cups. My breathing became erratic as I absorbed every fumbling, quivering movement of his hand sending exquisite ecstasy to my face. Suddenly, he squeezed my breast, going rigid.

"My diaper," he whimpered and squirted his overwhelming desire for me into his diaper once again.

He continued to caress me as his other hand soothed the intense spurts through his diaper. The plastic crackled loudly.

"My diaper," he repeated and then broke down in tears.

I guessed what he was thinking. He believed for sure now he not only needed his diaper because he was incontinent, but because he had to cum in it -- because of me. And just like he couldn't use the toilet, he had concluded that he could never have sex.

And yet, he kept making me feel good, pleasuring my breasts, even after he had cum in his diaper. Despite being sad, he still cared about me and wanted to look after my needs.

I lifted his head and kissed him. We embraced in a long hug while I supported him. In each other's arms, he let it all out. Eventually, he settled down and lay against me.

I returned his hand to my breast.

"Keep going," I told him.

This time, he started not just with one hand, but also the one that was clinging to his used-up diaper.

"Oh, Bobby," I said. "Take off my bra, please."

He fumbled with the clasps in the back with his eyes still teary and mesmerized by my boobs. How nervous he must have been to see them for the first time! I gave him a hand and my pretty pink princess bra came loose.

He froze in anticipation.

"Ready?" I asked.

He nodded and pushed the straps off my shoulders. I pulled my arms through, and Bobby removed it by the cups, at last beholding the exposed objects of his desire.

And there it was again: a new bulge emerged in his wet, cummie diaper.

I leaned back and pulled him over me. Lying on top, he pressed his wasted diaper into my clean one. He kissed each of my nipples in turn, sending shivers of pleasure through me.

"You're perfect," I heard him say.

He began to grind our diapers together while licking at my stiff nipples.

I gazed at the rain dropping above us onto the glass, making that constant pitter-patter, which reminded me that it was just us for miles and miles.

"Miles and miles," I said aloud as Bobby rocked us back and forth, the pleasure building in both of our diapers.

I pulled him away from my exposed breast and whispered in his ear: "Faster...Now slower...Harder...Lighter..."

I squeezed his back tighter at each word, my voice getting higher after every instruction. I closed my eyes as the intensity of the first climax Bobby was about to give me became apparent.

"I'm...almost...there...Ah!" And my voice cracked as I came hard in my diaper.

Bobby exploded into his, not able to get a single word out. He collapsed on top of me.

We both panted hard, but we started to laugh as the convulsions ceased and our pleasure became bearable.

Bobby rolled off me, and we closed our eyes to listen to the rain drops.

After a bit, I heard the crinkling of Bobby's diaper as he inspected it.

"Oh, no!" He exclaimed.

He rose to his knees, and I watched as he drenched his diaper again beyond his control. If he wet it further, he would leak!

"Bobby, you have to change," I told him.

He went quiet, unable to look at me.

"You didn't bring a spare," I added, drawing the answer from his silence.

"I'm such an idiot," he said, his hand supporting the saturated padding. "I thought we wouldn't be out so long, so I just needed the one I had on, but then all this happened. I forgot how much I depend on my diapers, and...damn it."

In his voice, I caught how much he lamented that his diaper had ruined the special moment between us. In much the same way, I felt guilty for dragging him out here and not considering his bodily needs. Either way, we had to find a solution before Bobby's disability caused him to wet his diaper again.

I touched my own padding as a reflex to his action, giving me a plan.

"You'll have to take off your diaper, Bobby."

"But I don't have a spare."

"Yes, you do. Mine." I grabbed his hand and rested it on my diaper. "It's still clean for the most part. I mean I did wet it, but not in that way...you know..."

"You don't have to do this, Katy," he said.

"I'm your girlfriend. Let me take care of you, Bobby. Please."

He looked at his diaper and then at mine.

"Okay," he said at last.

"Is it alright if I change you?" I asked, not sure how he would respond.

He scooched closer, giving me the answer. "Alright," he said, smiling. "Let's do it."

I started by getting the wipes out of my handbag, then removed my diaper. Once it was off, I realized I was now butt-naked in my boyfriend's car in the pouring rain, at night in the middle of nowhere, but I didn't stop. He needed me.

Bobby lay back and spread his legs. I removed the tapes, but as I got to the last one, I paused since it occurred to me, I was about to see him fully exposed for the first time.

"Katy, are you okay?"

"Yeah." I smiled, regaining my nerve. "This is a big moment for me, Bobby."

Seeing his manhood, it reminded me of all the times I made Bobby cum in his diaper. How good I made him feel, and he how did the same for me. I wanted to be closer to him, and this was the instrument to allow me to go further with him.

I cleaned him up, removed his soggy diaper and rolled it into a ball. I then placed my own diaper underneath him, pulled it over his front, and taped it in place.

"Thank you," he whispered when I finished. "I need my diapers so much."

In response, I leaned down, kissed him and we made out. I caressed the diaper -- my diaper! -- I had changed him into while he fondled my breasts, the pieces of me he ogled so much, until we started to yawn. It was time to go home. Reluctantly, we began dressing.

"Bobby, can you help me put this on," I asked, holding up my cute princess bra.

"Sure," he grinned, taking it from me.

He snuggled the cups back onto my breasts, and then he got behind me to clasp it into place. I hoped this would help him to do better the next time he took it off even though I enjoyed how he had struggled to remove it when his urges had made him lose control.

We drove down the mountain.

I felt self-conscious not wearing anything underneath my skirt despite how liberating the sensation felt. Bobby smirked without saying a word, letting me know how much he enjoyed the state in which I found myself. We talked very little the rest of the way home.

"Thanks for letting me wear your diaper," he said when we had arrived at my house, and he had parked the car in our driveway.

"That's why I'm here," I told him, "And you are too: we can help each other."

My remark snapped the last pieces into place for Bobby, and from his mouth came the words I had wanted to hear from him for so long.

"Katy, I love you. Give me a little more time. And I'll be ready to do it."

I knew exactly what he meant. I leaned over, kissed his cheek, and whispered in his ear. "I love you too. And later, I want you to tell me all about how you are going to

masturbate in my diaper."

Bobby flushed bright red and stammered before seeing the huge smile on my face. We both laughed.

"Okay. I promise that I will," he told me.

As I stepped out, I said to him, "When you're fully ready, I found the perfect place today for us to do it." And I left him with that next bit of anticipation.