We're Good Friends
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 different bright colors every month or so, was about 5'4", 105 lbs with a huge ass and A cups. 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 type of free spirit who would flash me her tits while I was 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 very shy on there either. Kayla had a whaletail visible almost 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 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 see always tell 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, 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.
She burst out laughing and said "dude, I've given you like, 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 in that moment. I tried to hide that I was already hard, and said "get me hard right now, I'll show you."
She laughed even harder and said "Dude, you're already hard!" And brushed her hand against my rock hard boner.
"It gets way bigger than this!"
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 tiny precum leaking 4" boner.
She laughed again, probably at how hard I was trying 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 her small tits and amazing ass, dreaming of shoving my little boner into her. I couldn't handle it in the moment, and I felt an all too common feeling. My balls tensed up and I knew my 4 inch monster was going to cum right then and there, so I quickly reached to pull my pants up and try and hide my impending orgasm, but she stopped me.
"No I'm sorry, keep it out, I wanna see it!" And she 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 all the way up to her shoulder, and we both stared silently at the mess I'd made for about 5 seconds.
"Oh, I'm so sorry. This wasn't supposed to happen." I felt like crying, but was so turned on that I was living in a real life humiliation porn video. I had never been so embarrassed, and I had never been so turned on.
She laughed so hard she started coughing and wiped her arm on a towel hanging from her 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 tears, as I saw zero desire in her eyes.
"No, I told you. We're good friends."