We held hands as we kissed, and my well-developed breasts pressed against him the first time I made him cum in his diaper. In our senior year, everyone at school new about Bobby's damaged bladder that required him to wear diapers. He had some friends, but he steered clear of girls like me who intimidated him. He had caught my attention though during PE where he demonstrated how many pull-ups he could do. There was more to him than met the eye, so I lied about where I was going after school and walked home with him.
He fidgeted with his hands and looked down to avoid staring at my breasts, which I caught him taking glances at anyway. In fairness, I spied at his pants to see any indication he was wearing a diaper.
I avoided that topic altogether, asking if he ever had a girlfriend. He of course said, "no." I followed with if he had ever kissed a girl before to which he repeated his first answer. I offered to be his first if he wanted.
He froze. Unable to speak despite it being clear to me he wanted it. He just did not know whether to take my offer in earnest. I took his hand and looked up at his cute face to show I was serious. I leaned closer to him to which he at last took the hint and pressed his lips to mine. He did not know what to do beyond lock lips, so I moved my mouth around his as slow as possible stepping close enough for our bodies to touch.
My curiosity got the better of me since I wanted to confirm the presence of his diaper. I pressed myself against his crotch forcing my breasts to touch his chest as well. He broke off our kiss. I was scared I pushed it too far, but I heard a faint, "ah!" escape his mouth as he gripped my hand. I thought for sure I felt some shaking in his nether region where I discovered the unmistakable softness of his diaper. At that point I knew I made he cum in his diaper.
He tried to hide his embarrassment and shame behind his stammering and looks away from me, but I just blurted out, "Did I make you cum in your diaper?"
Bobby's face flushed red. I caressed his cheek knowing he could not respond.
"It's okay," I reassured him. "I kind of like it. Do you want to go out?"
I surprised even myself with the question, but I seized the moment by kissing him again to show my sincerity. He nodded in response. As we parted ways, I caught him readjusting his crotch to accommodate the mess I forced him to have in his diaper.
Making Bobby cum in his diaper became my obsession. At our second meeting, I invited him to a secluded spot at the outskirts of our school. We made out. I pressed myself against his diapered crotch, which in no time caused him to cum in his diaper again. I knew when it happened right away because he paused for an instant while we kissed, trying to hide what happened.
I needed to escalate our encounters in order to keep pushing him over the edge. The third time around I asked him to touch my breast to which he hesitated to fulfill his obvious desire. The shirt I wore also revealed parts of my bra that he could not help staring at while he inched closer to my chest. It made him lose control of his boy part snuggled in his diaper once more when his hand met my breast. This time he did not bother hiding the ecstasy on his face.
The next time we met I had to grind against the hardness in his diaper in order to make him cum. It was clear he improved his control, so I invited him to my house for our next meeting. He hesitated at first, but he agreed once I promised we would be alone.
When he arrived, I wasted no time dragging him up to my room and shutting the door behind me.
He looked so nervous, but so was I. This was the first time I brought a boy over, but I felt safe and comfortable with him in a way I never got from any of the other guys I knew. I could ask him anything, and he would not think ill of me, so I asked the question I had on my mind most since we met.
"Bobby," I asked, "is it okay if I see your diaper?"
"Well...I..." he stammered.
"It's fine if you don't."
