My Diapered Boyfriend Ch. 03

I almost dropped my phone when I got the text from Bobby that my diapers arrived while I was chatting with my girlfriends. One of them, Annie, remarked that only my new boyfriend could get me that jumpy, and she was not wrong. The timing worked out since we were about to go our separate ways.

After saying my "Goodbyes" and sending a 'Thanks' to Bobby, I split for his house. I knocked the door, standing on and off my toes to calm down till the door opened and his older sister, Lily, stepped out. She goes to a nearby college, but I did not know she would be home for the weekend.

"Hey, you must be Katy," she said, smiling big to see me. "Bobby told me so much about you. Was he expecting you? He's still out with his friends."

That confused me. Why would he send a text when he was not home to know anything arrived?

"Is this about the pack of diapers that just came?" She asked.

I stared at her, mouth open, shocked she just said that which I realized was a mistake to let on I knew.

"I texted Bobby about them a little while ago," she went on, "did he tell you?"

Stone silent, I saw on her face she fit the pieces together of what happened: she told Bobby about the diapers, so he told me, and now I'm here flushing red, backing away from his porch.

"I-I-I think a got a text from Annie and mistook it for-" I said about to turn away when Lily grabbed my arm.

"It's okay," she told me, her grip slight so I could break out of it, but the ease with which she spoke stopped me. "You did nothing wrong. There's nothing to be ashamed of." She reminded me of my mom after she caught me. "I made some tea. Do you want to come inside?"

I relinquished, believing going away now might make me look suspicious in my first meeting with Bobby's family.

She brought a tray with a pot of tea and cups to the living room, sitting beside me on the couch after she set it down on the table. Lily showed no hesitation to close the distance between us as she handed me the cup. She sipped light, sensing how hot it still was, so she held it in her hand as it cooled.

I focused as much on her as I could to distract from the embarrassing way I acted outside, but as I raised the hot cup to my lips she asked, "You've worn diapers before, haven't you?"

I thought I might choke or burn my tongue attempting not to spit the tea all over the coffee table.

"Are you alright?" She said handing me a napkin, "I'm sorry. It's not anything to be ashamed of, but I know it's very personal."

She rested her hand on my back while I caught my breath and cleared my throat. Her touch felt reassuring, no judgement, and I realized, apart from Bobby, she might be the only one I could really talk to about diapers even if I did not feel ready yet. I wanted to know one thing from her though.

"Do you..." I asked, "think I'm weird, or...a creep?"

"Of course not," she said without hesitation. "You should be happy." She crumpled up the dirty napkin and placed it on the corner of the tray. "Do you like diapers?"

I stared right at her, seeing that warm smile, my guard lowered just a little for me to nod and grin before looking down.

"You're so adorable," she said, pulling my face back up to pinch my cheek.

I then put together how careful she was to choose her words because they made me admit the truth. 'Have you worn diapers?' Everyone has when they were little. She kept referring to me not doing anything wrong or being ashamed despite not saying what, and last, she asked a simple 'yes or no' question to get me to confirm I like diapers. I realized Lily came off as not just charming but clever.

I drank the rest of my tea to hide my revelation yet still feeling admiration for her since she showed no malice about it. She only wanted me to open up to her.

"Your diapers are upstairs in Bobby's room if you want to go get them," she told me taking the tray back to the kitchen.

"Thank you," I said. I stopped halfway up the stairs when I realized she played me yet again to learn the diapers were in fact mine. I shook my head and giggled it off as I headed to Bobby's room.

I first noticed his unmade bed, which did not surprise me at all. The large collection of butterfly displays across from it though caught me off guard. Some showed wings as wide as my thumb while others looked bigger than my hand. So many colors, they painted the wall in reds, oranges and blues. It took me aback, as gorgeous as I thought they were, only upon entering his room did I learn my boyfriend had such an interest.

My gander moved from his wall to the closet where I saw he kept his weights on the floor and a pull-up bar in the closet's frame, giving me an insight of how he kept in shape.

Between the bed and the closet, I found my pack of diapers. I picked it up, letting my hands run over the plastic to get the shape of them underneath. I almost gasped holding them, my ecstatic smile invading my face.

"Do you want to try them on?" Lily asked from the doorway.

I dropped my diapers in surprise acting like I saw a burglar. I worried I might scare her off, but Lily walked into the room and took my hands saying, "I'm sorry, Katy. You just looked so sweet and happy I thought...I might help you." She let go of me. "My bad."

She turned away from me to leave, but by instinct I grabbed her wrist, making a delayed response, "Please, wait. Thanks, Lily, for being so welcoming. It's just...this makes me so happy, yet it's so embarrassing, and...I don't know what I should do."

I let go as she walked around me to the side of Bobby's bed where she sat down and patted the open spot next to her for me to join. She put her arm around me after I came beside her.

"I want you to be able to tell my anything, no matter what it is, knowing I won't judge you, and keep it between us, if that's really what you want," Lily told me.

"I...I do want that," I said, letting out a long sigh. "There's a lot of stuff I'm unsure how to handle, so if I could...if you and I..." I had a hard time putting my wishes into words.

"That's fine," she responded. "No need to spell everything out at once. What's one simple thing you want? Name anything."

She pressed her forehead against mine, alleviating some of the stress I built up. I closed my eyes, facing down and focusing on where she touched me. And despite the anxiety that still raged through me, I dashed over it like hot coals to speak the first desire that popped into my head.

"I want to wear diapers with Bobby," I said.

"Hmm," she responded still holding onto me. "Then you should give him a call and tell him you're in his room, wearing your diaper, waiting for him."

She pulled away to see my face and how I responded.

I looked every which way except her eyes while the images formed in my mind of calling Bobby in my diaper and picturing him walking into his room and seeing me. I nodded in agreement with what Lily proposed.

I never said anything, but she got up and told me, "You better get to it if you want it to happen."

When she stepped toward the door, new questions popped into my head of how to make it work, so I stood without thinking and yelled, "Wait!"

Lily stopped and looked at me, and I lost the words for what I wanted to say.

"I-I..." I repeated till I gained the courage to say what worried me. "...I only put a diaper on once before, and I'm not sure if I did it right, so I wondered...if you might-"

She put her hand up in a 'stop' motion, and said, "Say no more." She took my pack of diapers and opened it, saying, "Can you lie on the floor?"

I nodded and did as she said. In fact, more than she said. I pulled off my pants without thinking, getting caught up in the moment that this was really happening. I froze when I reached down to remove my panties, realizing I was about to show my cooch to my boyfriend's sister!

Lily noticed me, and said, "Relax, Katy. We don't have to keep going."

Hearing her reassured me. No matter what, nothing would happen unless I wanted it. I took off my panties, which was all the encouragement she needed.

Lily slipped my new diaper beneath my bottom and pulled the front up to my belly. It impressed me how well she did it, making me think she changed Bobby's diaper when they were younger.

With the last adjustable tape in place, she took my hand and helped pull me to my feet, asking, "How does it feel?"

I shook my bottom around, feeling embarrassed yet excited, so I said, "Really good!"

"Do you want to see how you look?"

I almost responded 'yes' right away, but I closed my mouth instead to just nod as uncertainty creeped back into me.

Lily covered my eyes and lead me to her room, which she had left untouched for the most part since going to college. She brought me in front of her full-length mirror and pulled her hands away while stepping back, so only I stood visible when I saw myself in my diaper for the first time.

My blouse covered most of it except for the very bottom sticking out in all white between my legs where I felt its gentle warmth and softness. I lifted my blouse, slow, to reveal the whole thing, building up my courage as I went till, I fully exposed my diaper.

I gazed from my diaper up my body to my eyes reflected in the mirror, and I said to myself, "That's me. That's me in my diaper."

Lily stepped into view behind me, holding something behind her back she looked anxious to reveal. She said, "You look so cute," in a way that made me think of a mother complimenting her daughter in her wedding dress.

As if to distract me from what she held behind her back, she added, "What are you waiting for?"

It took me a sec to remember she meant calling up Bobby, so I returned to his room to fetch my phone from my handbag. I graced my fingers over the front of my new diaper while I waited for him to answer.

When the ringing stopped, and I heard his voice, I said, "Hi, Bobby. How are you?" It gave my nerves time to settle down.

"I'm good," he answered. "The guys and I are just heading over to Johnny's place from the park."

"Oh," I sounded unsure whether I should continue. However, Lily walking into his room gave me the push I needed to tell him, "well, guess what? I'm in your room right now, wearing my new diaper."

A long silence followed. I heard the voices of his friends in the background. I decided to break it.

"I'll be waiting for you," I said in my flirtiest voice.

"Um. Uh, just..." he spoke, "...give me a bit."

Lily came up and shout-whispered to me he should come in only wearing his diaper to make me feel more comfortable. I did not know if she fully meant it as a joke, but I repeated the request to Bobby who took it in earnest.

"S-sure. I'll see you soon," he said.

We hung up.

I let out a long sigh, dumbfounded that I actually did that. Lily gave me a kiss on the forehead, telling me, "Good luck," before closing Bobby's door behind her.

While I waited, I paced back and forth across his room, listening to the crinkles of my diaper. My hands kept sliding up and down it over and over again, building up the pleasure inside me as I pictured Bobby heading home. I lay on his bed, telling myself to 'calm down,' yet I just ended up smelling him on the sheets increasing my anticipation.

At last, I heard the front door open and then close, letting me know he arrived. I listened to his footsteps climb up the stairs while I stood up and adjusted my blouse so only the very bottom of my white diaper would show when he opened the door. I realized he stopped right in front of it. I wondered if he was hesitating until it sounded like he was taking off his pants and shirt like I requested.

My heart racing, I held my breath when he opened the door and before anything else, my eyes went straight to his face where I caught the sight of his astonished gaze as he beheld me in my new diaper for the first time. I knew I enraptured him at just that glance with only the slightest glimpse of my diaper and the curves of my body outlined by my blouse.

During his shock, I feasted on my initial taste of his arms and his pecks, which I learned just a short time ago he worked so hard for as well as his abs that waved down to meet his diaper. With one hand he closed the door behind him. With the other, his dominant one, the one I remembered he masturbated to my breasts with last time, he covered the intense joy he felt in his diaper.

His mouth opened, but he couldn't speak, so I smiled at him, acting shy and lowering my eyes down, where his followed. I lifted up my blouse, ever so little to give him a tease. His sole focus there encouraged me to indulge in my fun.

Bobby stayed near the door, afraid to step closer. His breathing already erratic, he squeezed the front of his diaper in a desperate attempt to hold in his release. I wondered how far I could go before he gave in to his urges for me. I continued to lift up my blouse till I revealed my whole diaper and did a slow spin to even show him my bottom.

"Well, Bobby?" I asked. "How does my diaper look?"

"Y-you...you look so great!" He said with both hands clutching his crotch and his knees buckling.

"Thank you," I replied, stepping closer to him and raising my blouse enough to expose the bottom of my white lace bra.

"Oooooh!" Bobby moaned, like he sounded in agony, yet he couldn't tear his eyes away from me.

I only now realized my bra matched my diaper just right. Almost like my breasts nestled in their own diaper. This revelation got me so giddy, I raised up my blouse until I showed off all of my boobies to him.

Bobby fully took in the sight of my breasts resting in my white cups decorated in rose patterned lace with a little light pink bow between them. He fell to his knees, clutching his diaper for dear life, pleading to me.

"No more. No more," he repeated. "Katy, please. It's...you're too much for me. Your diaper. Your breasts!" He stared at the floor unable to take in any more of me.

I kneeled down in front of him, realizing what I should have known since we first met: cumming in his diaper was the price Bobby had to pay to be close to me.

"Face it, Bobby," I told him. "My diaper and my boobies are gonna make you cum." I put my hand on his shoulder. "Make the most of it."

He raised his eyes up from the floor to my too cute diaper, making his way higher till he reached my breasts, seeing them nestled in my bra like their own diaper.

"Aaaaaah!" Bobby yelled, going solid stone between his legs because of me. He fell on his side, eyes clenched shut, and...Squirt. "My diaper!" Squirt. "My diaper!" Squirt. "My diaper!" He said it now as a means of release from the intensity.

After a bit, his breathing calmed, and I ventured to rest my hand on his shoulder while he recovered. Bobby still clutched his now cummie diaper.

"I..." he began to say when he could talk again, "...I wanted to make it up to your face and kiss you when I...but I couldn't make it..."

"It's okay, Bobby," I told him.

I rested on the floor next to him, wanting to cuddle up, but I knew he was still too sensitive from cumming in his diaper just because of my breasts.

"Oh no," he said feeling his front.

"What's wrong?" I asked, getting worried this was all too much for him.

"N-nothing."

I stared down at where he covered the front of his diaper. I then looked up at his face, right into his eyes, and he knew I figured it out just by looking at me. There was no hiding the truth.

"I wet my diaper, Katy," he confessed, turning towards the floor from shame at wetting and cumming in his diaper in front of his girlfriend.

I just said to him, "I'm happy you can tell me that, Bobby. It makes me feel close to you."

My feelings gave him courage to show me his wet cummie diaper. The obvious line where it absorbed his wetting and sagged his diaper drew such a difference between his and mine, I got a little embarrassed. He slapped his dominant hand on it though, and when I saw his eyes gazing at my breasts again, I understood why.

Bobby needed to fully embrace his attraction to me, or else he would continue feeling bad about cumming in his diaper from my breasts, my diaper and everything else.

Without warning, I stood up and took off my blouse. Now in only my diaper and white lace bra, I rested on Bobby's bed, laying on my side, facing him. I told him to kneel over by me, which he did.

"Bobby, do you like my diaper?"

"I-I do. Very much."

"Do you like my breasts?"

"They're very beautiful and captivating."

"And do you enjoy cumming in your diaper?"

"To be honest, it feels really good."

I leaned in close to him, saying, almost in a whisper, "Then, will you masturbate to my diaper and my boobies?"

"B-but you already made me cum in my diaper. I wet it too."

He could see that I could see that he could not take his eyes off my breasts. His dominant hand also soothed the raging stiffness within his diaper.

"You have to cum in your diaper," I told him. "You can't go on like this. Please."

At last, Bobby gave in, stroking the front of his diaper as he gazed at my breasts nestled in my white lace bra.

"Does it feel good to masturbate to my breasts in your wet cummie diaper?"

"Yes!"

"Tell me how it feels."

"It...it feels like I have to go so bad, but I can't let it out. The only salvation I have is your breasts. They grabbed hold of me and won't let go until I wet my diaper. It feels so excruciating that your boobies will make me let it all out, but..."

"What?" I hung on every word he said.

"I-I-I want your boobies to make me cum in my diaper!"

Bobby squirted into his diaper. First with my breasts then his gaze wandered down till he saw my diaper, and he squirted again, yet last he ventured up to my face and kissed me deep as he squirted into his diaper a final time.

His lips broke away from mine in exhaustion. Falling to the floor, I caught him by the hand he just used to masturbate to my breasts and lowered him down. I still felt the thrill in my diaper while holding him.

After he recovered enough to stand, he joined me on his bed. I noticed how different our diapers looked now. Whereas mine still looked pristine, clean and adorable, his became bloated from wetting it and loosened from stroking to his desire for me. I understood, better than ever, how Bobby needed his diaper for wetting and cumming compared to me who just enjoyed wearing it.

"Are you okay?" He asked since I went quiet for so long.

"Yeah. How's your diaper?"

"This one's pretty used up. I'm gonna have to lose it."

"Does that make you feel bad?" I asked looking down at my own diaper compared to his.

He kissed my cheek, saying, "You make me feel so good, I don't care how many times I lose my diaper."

Bobby rolled on top me, pressing his cummie diaper into my clean one. I felt his stiffy returning. He began thrusting onto my diaper, slow at first, looking right into my eyes. He sped up though when his pleasure fully returned, and I felt my own rising right along with him, begging for release.

The intensity soon became too strong for Bobby. His eyes kept closing. He clenched his sheets. I held onto him tight. My climax rushed into my diaper alongside his. I knew he was not ready to make me cum though. Each time before, I lay on top, taking the lead. Making him cum came so much easier for me. I realized, however, Bobby really needed to feel this, to make himself cum in his diaper while trying to do the same for me.

"You feel so good, Bobby."

"Katy, I'm gonna cum. I'm gonna cum in my diaper!"

"Just cum, Bobby. Please. You can do it."

He squirted into his diaper the final time touching my diaper. He stared into my eyes: enthralled.

"Katy...my diaper..."

I caressed his cheek. "I know. You did so good."

We kissed so long with his cummie and my clean diaper together.

When Bobby slid off me, I still felt the insane need to cum, but I hesitated to masturbate in my diaper next to my boyfriend once I got a better look at his diaper.