Kayla and I were incredibly close friends in our senior year in high school. I was so hot for her, and she knew it. She dyed her hair in bright colors every month and was about 5’4”, 105 lbs with a huge ass and A-cup breasts, while I towered over her at 6’2” and thin as a rail, 160 lbs. We would hang out almost every day after class. She was the free spirit who would flash me her tits while driving or playing video games to distract me, and it usually worked. So many people had seen her flashing at parties, backstage at our school plays, and Chatroulette had just come about, so she was never timid either. Kayla had a whale tail visible 24/7, and I’d always comment on it, like saying how much I like the color or snapping it onto her pale skin.

I probably asked Kayla out a hundred times, and she always rejected me, saying, “We’re just good friends,” or whatever canned line to let me know I wasn’t good enough without trying to get me too down about it.

Of course, being friends never slowed her down with hooking up with anyone else, and she always tells me all about guys and girls she hooked up with, knowing how badly I wanted her. The best day of my ‘never-been-touched-virgin’ life came after me about an older guy she hooked up with. We were in her room after school on a Monday, and she kept going on about a guy she met over the weekend and how big his cock was, and she said, “You have no idea.”

I figured I’d try and talk big, so I said, “Oh yeah, how would you know?”

I knew I was lying, and I had measured my penis almost every day since I was 16, hoping it would grow bigger than a mere 4 inches. One time, I thought I’d made some progress up to 4.25”, but that quarter-inch was gone the next night. I must’ve been super horny.

Kayla laughed and said, “Dude, I’ve given you a million boners. I’ve seen what you’ve got.”

I had already been watching some small penis humiliation videos online and got the guts to keep pushing her on it and get as humiliated as I could at that moment. I tried to hide that I was already hard and said, “Get me hard right now. I’ll show you.”

She laughed harder and said, “Dude, you’re already hard!”

Kayla brushed her hand against my rock-hard boner.

“It gets way bigger than this!” I said.

She looked annoyed about what she had gotten herself into and said, “Ugh, just take your little dick out and prove it.”

I rocketed to my feet, undid my belt, and pulled my pants down to my knees, showing off my little precum leaking 4” boner.

Kayla laughed again, probably at how hard I tried to impress her and said condescendingly, “Aw, your dick is not big, like, at all.”

Hearing those words out of the mouth of the object of my infatuation drove me wild. I had spent so many nights masturbating to the thought of Kayla’s small tits and fantastic ass, dreaming of shoving my little boner into her cunt. Unfortunately, I couldn’t handle it now, and I felt an all too common feeling. My balls tensed up, and I knew my 4-inch monster would cum at that moment, so I quickly reached to pull my pants up and try to hide my impending orgasm, but she stopped me.

“No, I’m sorry, keep it out. I wanna see it!”

Kayla touched the bottom of my shaft. With that, I came all over her arm. The biggest orgasm I’d ever made shot from her wrist up to her shoulder, and we both stared silently at the mess I’d made for about 5 seconds.

“Oh, I’m so sorry. That wasn’t supposed to happen,” I said.

I felt like crying but was so turned on that I lived in a real-life humiliation porn video. I had never been so embarrassed, and I had never been so turned on. Kayla laughed so hard that the girl started coughing and wiped her arm on a towel hanging from the closet door.

“It’s okay. Lots of guys your age premature ejaculate.”

I loved how she said ‘your age,’ since I was two months older than her, and ‘premature ejaculate’ sounded so textbook-like she was this expert lecturing my little self on my shortcomings.

“Can we try again, please?”

I was still fighting back the tears as I saw zero desire in her eyes.

“No, I told you. We’re just good friends,” Kayla said firmly.

 

The End.

 

*This story has been edited to fix spelling, punctuation, & basic grammar, but the narrative and plot have remained the same. Remember, even with limited editing. It doesn’t mean any possible major flaws in this story were fixed.