My turn was next in this dreaded Monopoly game, and just having shot my load for the second time, I was exhausted and ready for it to be over. I told the group I was going to bed, but Nick stepped in and said, "Come on man -- let's just do one more round!" So begrudgingly, I rolled the dice.
I was so close to passing "Go" but instead ran straight into Boardwalk. Looking around, I felt a sinking feeling in my stomach when I noticed that it was owned by Drew. "Oh shit!" I thought. My best friend had promised revenge when I'd tried to make him suck my cock, and now I'd just fucked his girlfriend in front of everyone on the trip.
Drew smiled as he walked over me, his big, thick dick leading the way. "You're gonna get it now," he said. "You think you can force me to suck your pathetic cock and then fuck my girlfriend? You are figuratively and literally FUCKED!"
I whimpered as I cowered beneath my best friend, but also couldn't help admiring his toned and sexy body. Six inches shorter than me with short, curly brown hair and piercing green eyes, he had muscles from baseball and lacrosse all over his sweaty body. With a massive, thick cock swaying between his legs, he was clearly the alpha to my beta.
Without Drew saying a word, I dropped to my knees and lunged at his dick. By this point in the game, I wasn't thinking very clearly, but I hoped that if I could get him to cum (as he had made me prematurely cum), then he'd no longer feel like fucking me. By sacrificing my mouth now to his semi-erect manhood, I had a shot at not getting fucked up the ass.
Drew stayed silent as I went to town on his cock, licking and slurping on it all the way down. Unlike with Brayden, I could fairly easily deep-throat every inch of Drew's massive dick. Both his brothers and the girls watched on as I went to town on his dick like a greedy little bitch.
For several minutes, I felt like I was making progress and getting Drew on the brink of cumming. But as I looked up into his eyes, he just smiled calmly down at me.
"Thanks for lubing me up and getting me hard," he laughed. "Are you ready for your dare?"
"What?" I said, exasperatedly, as his throbbing 7-incher slipped out of my mouth.
"You were so eager for my cock you couldn't wait -- but I'm still gonna pop your cherry right in front of your girlfriend and everyone else."
"Noooooooo!" I begged. "Please don't fuck me. I'll keep sucking you -- I'll do anything!"
"This was the game you agreed to. You fucked my girlfriend, and now you're gonna get fucked in return!" Drew said confidently. "And I know you want it -- your little boy penis is throbbing once again!"
More than anything, I did NOT want to get fucked my best friend in front of his brothers, my girlfriend, and Monica. But sucking on Drew's dick for the second time that day had unlocked something deep inside me and my own penis was fully erect and throbbing for all to see.
I don't know if it was Drew's thick man-meat that was two inches longer than my own, his athletic good looks, or the arrogance he exuded, but something made me feel like I needed to submit to him completely. So when my best friend told me to get on all fours and put my ass in the air, I surprisingly obeyed.
Right in front of my girlfriend, his girlfriend, and his two younger brothers, Drew smacked my ass a few times with his big, thick dick. "You know you want this," he said, arrogantly. "I know you've been fantasizing about it for a long time."
Unable to say anything, I simply moaned in response.
"Beg for it, bitch," he said.
Holding onto my last shred of dignity, I really didn't want to beg. But Drew's dick felt so big and thick rubbing against my ass that I couldn't stop moaning. As the throbbing head of his cock slid against my aching hole, Drew slapped my ass -- HARD.
"Beg for it, bitch," he said again.
I couldn't bring myself to beg for it, but I did moan even more loudly as Drew kept smacking my ass. His dick felt hard as a rock and so big and manly. My moans grew even louder when Drew reached around and pinched my nipples. As I moaned and squirmed on his cock, Drew reached lower and grabbed my throbbing erection that was now leaking a significant amount of precum.
"Beg for it, bitch," he said again.
Despite being more humiliated than I'd ever been in my life, I was somehow turned on like never before. With my best friend fondling my penis like it was a clit and squeezing my nipples—and his massive hard-on rubbing against my hole—it felt only natural for me to become his bitch.
"Just give it to me," I whispered softly, between moans.
"What was that?" he asked cockily.
"I said 'just give it to me,'" more loudly so that everyone could here.
"You'll have to do better than that," he said. "You need to beg for it, bitch."
"PLEEEEEEEEEEASSEEEE!" I yelled. "PLEEEEEEAAASSEE FUUUUCKKKK MEEEEEE!"
None of us could believe the words coming out of my mouth, but Drew's hands and cock were driving me insane. As I was moaning and writhing on the floor, Drew pushed the thick, manly head of his massive shaft into my waiting hole. As my girlfriend, Monica, and the Cox bros looked on, my anal virginity was slowly but confidently taken by my closest friend.
I struggled to breathe as Drew pushed all seven thick inches inside me. I felt completely full and still as turned on as I'd ever been. I'd always been the more dominant guy in our friendship. Six inches taller than Drew, I was typically cockier than him and more confident. But throughout this week, the tables had turned and Drew was now fucking me in front of everyone and making me his little bitch.
Drew's confidence took over as he started pounding my ass doggy-style right in front of Nick, Brayden, Monica, and Leslie. The girls were so turned on by my humiliation that they nearly dove onto the younger Cox bros' cocks, until all six of us were fucking right there in the living room.
It turned me on even more to see my girlfriend getting impaled on Nick's insanely huge 10-inch cock. But as I reached beneath me to stroke my own aching erection, Drew laughed and slapped my hand away.
"You won't be needing that, bitch," he said.
Drew then flipped me over so that he could fuck me face-to-face. Somehow this felt far more intimate and humiliating, since I could look directly at his handsome face and piercing green eyes as his thick man-meat fucked me into oblivion.
Drew grinned as he looked down at my face and throbbing boyhood. My penis was pulsing and leaking pre-cum everywhere, despite no one currently touching it. And despite the greatest humiliation of my life, I couldn't help but scream for this stud to pound me even harder.