Andrew had known my secret for months.
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When I nervously confessed that I was a cuckold, turned on by imagining him with other women, he didn’t judge me. Instead, he embraced it, teasing me gently about my modest five-inch frame and flexing his imposing arms whenever I was near. He’d joke that the girls he hooked up with could never be satisfied by my pathetic offering.
Yet, despite all the teasing, he had never actually let me watch — not until tonight.
I had pleaded for weeks, exposing my insecurities each time, wearing my nerdy vulnerability on my sleeve as I begged him.
Finally, after a late-night message where I admitted how desperate and inadequate I felt, he replied:
“Alright. Sam’s coming over. You can watch. Just this once, man. Feels like you really need it.”
Sam — our stunning former classmate from high school — arrived looking irresistible. She wore a tight, short skirt and carried herself with a knowing confidence that left no doubt why I sat silently in the corner, heart pounding. Andrew was already shirtless, his muscular body relaxed yet commanding, casually sipping a drink as if this was no big deal.
“You sure you’re okay with this, bro?” he asked softly one last time, genuine concern in his voice. “I’m only doing it because I can see how much you want this.”
I nodded eagerly, unable to speak.
The moment Sam sank to her knees and pulled Andrew’s shorts down, the atmosphere shifted.
His cock sprang free — thick, heavy, swelling into a true powerhouse. Nine and a half inches of veiny, thick perfection that made my five inches seem laughable. Sam’s eyes went wide.
“Jesus, Andrew… no wonder those Magnum XLs were tight. That thing’s massive.”
Andrew glanced at me with a smirk mixing amusement and sympathy. “Yeah, poor guy’s dealt with that little thing his whole life.”
And then it happened.
The calm, considerate Andrew I knew vanished the instant Sam took the head of his fat cock into her mouth. His hand gripped her hair firmly, driving his long, dominant thrusts deep down her throat, testing her limits with each stroke.
“Fuck yes,” he growled, voice low and raw. His biceps bulged, chest flared, abs tensed into sharp definition while he used her mouth like a privilege. His dominant side emerged quickly; he slapped her face with his throbbing cock before forcing it back into her, making her gag and drool.
“Look at him,” Andrew commanded, pointing at me. “That’s why you’re here. My best friend won’t ever be able to stretch a pussy like this.”
He hauled her onto the bed, ripped off her panties, and slammed every inch of his colossal cock inside her in one ferocious thrust. Sam gasped, a mix of pleasure and shock flooding her senses. Andrew didn’t hold back — he fucked her hard, deep, and relentless, each powerful hip thrust flexing his chiseled body, slick with sweat.
He kept glancing at me, eyes a mix of pity and arrogance. “This is what you wanted, right? Watching a real man handle business?”
Sam was a moaning, trembling mess beneath him, squirting uncontrollably as each deep stroke pushed her higher. Andrew folded her over, legs draped over his shoulders, pounding her even harder while his massive arms and chest flexed like a pornstar on stage. He lightly choked her, bit her neck, and growled filthy praises about how tight she was compared to those who had to settle for less.
I was slick beneath my jeans, rubbing my pathetic five inches, overwhelmed by humiliation and an intense, forbidden arousal I’d never known.
At last, Andrew pulled out, stroked his dripping cock, and blasted thick, powerful ropes all over Sam’s breasts and face. She orgasmed again just watching.
Afterwards, Sam lay there panting, blissfully spent. “That was the best sex of my life… holy shit.”
Andrew wiped sweat from his forehead, still casually flexing as he caught his breath. He gave me a soft, almost sympathetic smile.
“Best I’ve had in a long time, too,” he admitted, then clapped me on the shoulder, his huge cock still hanging heavy between his legs.
“Feeling better now, bro? I told you I’d take care of you.”
I nodded, utterly spent and inexplicably satisfied in the most perfect, pathetic way possible.
But that night marked only the beginning of how our friendship would evolve.