“I just busted your second hole” my buddy Chaz breathed in my ear, his thick stache tickling my cheek as he ravaged my hole with his massive cock upon the hotel bed. He had breached my inner-sphincter, my eyes rolling back into my head. “I bet your wife can’t do that with that latex strap-on she pegs you with,” he laughed mockingly, his meaty hand gripping my neck.
Chaz and I weren’t supposed to be sharing a hotel room. There had been a mistake when our company booked us for a three-day financial conference in Chicago, and we were forced to share a room. Most straight guys like me would never agree to sleep in the same room as an openly gay dude, but I didn’t mind because Chaz was my friend and I trusted him to not exploit the situation.
Chaz was the only gay guy on our all-male team of financial planners at work. It wasn’t easy for him, trying to fit in amongst the guys with his ear piercings and often over-the-top demeanor. But Chaz was stellar at his job, proving his merit in a boys’ club that possessed all the toxic masculinity of a frat house on a Saturday night.
Sadly, the other guys in the office often ostracized Chaz, never inviting him for lunch, golf, or beers after work. I felt bad for him, and so I made an effort to befriend Chaz despite the snickers from the other guys behind my back.
“You’re not weirded out that we are the only two guys on the team being sent to the conference in Chicago?” Chaz asked with concern when we were given our orders. “A lot of the guys in the office already think we’re fucking just because you have the decency to talk to me.”
“Fuck those homophobic assholes,” I replied. “I’m a happily married man. I have no reason to fear their gossip and insinuations. Being work buds doesn’t make us fuck buds.”
“That could be arranged,” Chaz winked.
“Yeah, right,” I laughed. “I know I’m not your type. You’ve shown me the photos of all those Grindr twinks you fuck.”
The fact that we could joke about our differing sexual orientations allowed me to have no concern when I was forced to share a hotel room with Chaz in Chicago. I trusted him completely to not make a move on me. But did I trust myself?
The first day of the conference had been exhausting. We had taken an early-morning flight and then suffered through a painful round of sessions. There was a cocktail party and then a dinner, followed by a keynote speaker who droned on endlessly. By the time Chaz and I got back upstairs to our hotel room, all I wanted was a hot shower.
Chaz was sitting on the edge of his bed, hunched over his phone, when I emerged from the bathroom freshly showered, a flimsy hotel towel wrapped around my waist. A series of pings emitted from his phone as he tapped at the screen.
“You playing a game?” I asked.
“No, but it often feels like a game of cat and mouse,” Chaz laughed. “I’m actually on Grindr looking for some ass to fuck.”
“Wait—you’re gonna invite some random guy here to our hotel room—to fuck?”
“Calm down,” Chaz raised his hand to subdue me. “I’m not going to fuck some dude in front of you. I’m looking for a guy who can host, which is proving to be almost impossible.”
“I’m sorry,” I offered feebly.
“If you were truly sorry, you’d drop that towel and let me mount your ass on this bed,” Chaz laughed in jest. “But I know you’d never take a dick up your ass.”
“Don’t be so sure,” I admitted, the three martinis from the cocktail party still working their magic on my inhibitions. “I’m not as innocent as you think.”
“Wait—what?” Chaz gasped.
“Jesus, I’ve never told anyone this,” I exhaled, taking a seat next to Chaz on the bed. “My wife likes to peg my ass with a strap-on,” I confessed. “She enjoys the power dynamic. We saw an intimacy coach when our sex life was in the toilet after our kids were born, and he suggested we try pegging to sort of flip the script. My wife loves it.”
“But do you love it?” Chaz asked. “Taking a fake dick up your ass?”
“Yeah—I do,” I admitted freely. “I had to warm up to it at first, but I quickly learned that it feels really good. I’ve had some of the best orgasms of my life with that fake dick up my ass.”
“Have you ever thought of taking a real dick up your ass—you know, one that wasn’t made of latex?” Chaz inquired.
“Yeah—I have,” I acknowledged, reaching for his crotch, rubbing his hard cock through his pants. “I’ve thought a lot about taking your cock.”
“Oh yeah?” Chaz smiled deviously, undoing his pants. “I should warn you that I’m a lot bigger than some six-inch strap-on that your wife uses on you. I’m hung like fuck.”
“Holy fucking Christ,” I gasped as Chaz pulled out his cock. It was easily north of nine-inches, thick and veiny, crowned with a huge mushroom head that was already leaking precum.
“You still want this big dick up your ass,” Chaz taunted, slapping that big piece of meat against his open palm. “You don’t have to take it, if it’s too big for you.”
“No—I—I want it,” I stammered, still in awe of its magnitude. “I want you to fuck me with that big cock.”
“You ever sucked a man’s cock?” he asked, swiping up the precum running down his shaft and forcing his finger into my mouth. A luscious taste of salty and sweet coated my tongue, whetting my appetite for more. “You ever had a dick down your throat?”
“No,” I admitted, reaching for his cock with my hand, bringing it to my lips. Chaz allowed me to lick up and down his thick shaft and then suck on that massive head before he grabbed the back of my head and forced his big cock down my throat. I gagged on it, unable to take it all the way.
“Don’t worry about that,” he laughed, extracting his cock from my throat. “I’m not looking for some head tonight. I want to fuck your ass.”
I then watched as Chaz stood up from the bed and removed his clothes, his big dick maintaining a rock-hard erection the entire time. He then rifled through his toiletry kit in the bathroom, producing a small bottle of lube.
“How does your wife peg you?” he asked, greasing up his cock with lube, pumping it with his fist. “I bet she prefers missionary.”
“Yeah,” I confirmed. “She likes to look in my eyes when she’s pegging my ass.”
“Then roll over onto your stomach,” Chaz commanded. “We’re gonna play it a bit differently for you tonight. I want you to feel the weight of my body upon you as I wreck your hole from behind.”
Obediently, I opened my towel, discarding it on the floor before rolling onto my stomach. I was ass up on the bed, my hole presented to Chaz for his domination.
“Fuck, you’ve got a pretty cunt,” Chaz marveled, climbing on the bed behind me and spreading my ass cheeks. His face was suddenly in my butt crack, his stache tickling my hole, his tongue probing at my orifice.
“Christ, that feels good,” I exhaled as Chaz licked and sucked at my puckered sphincter, getting it ready for his big dick.
“I take it your wife doesn’t eat your hole before she pegs you,” Chaz assumed correctly. “I could eat your ass all night, but I’m more in the mood to fuck.”
And then I felt it, Chaz’s muscular body upon mine, his hairy chest pressed into my back. His rounded cock head was soon pressed against my hole, my sphincter bracing against the intrusion. And then with a swift thrust, Chaz was inside me.
“FUCK,” I screamed, my voice echoing against the walls of the room as Chaz went balls deep in my void. “You’re so fucking big.”
“You’re just realizing this now?” he laughed, playfully biting my ear as he routed my fuck canal. He was employing a series of deep strokes, already exploring far deeper than my wife’s strap-on had ever been.
“Is this your first time?” I inquired, my novice hole still on fire. “You know—your first time fucking a straight guy like me?”
“Hardly,” Chaz laughed openly. “If it wasn’t for straight guys, I wouldn’t have gotten laid as often as I did in college. Those frat boys sure love bending over when you get a few shots of tequila in them.”
He was pounding me hard, his hairy body slamming into me over and over. It was nothing like being pegged by my wife. The brutality of having a man inside of me, dominating me with his big cock, forcing me to submit to his animalistic desire, was a huge turn on.
“Raise your ass,” Chaz commanded me. “Open that cunt for me.”
And then it happened. As I tilted my pelvis, raising my ass slightly above the mattress beneath me, I felt it. Chaz’s big cock pushed impossibly deep within me. There was a sudden change in pressure that felt like the pop of a champagne cork, another portal opening within me.
“I just busted your second hole,” Chaz breathed in my ear, his thick stache tickling my cheek as he ravaged my quivering hole. He had breached my inner-sphincter, my eyes rolling back into my head. “I bet your wife can’t do that with that latex strap-on she pegs you with,” he laughed mockingly, his meaty hand gripping my neck.
He was right. I had never been routed so deep. The sensation was incredible, my toes curling, waves of pleasure consuming my body as Chaz proceeded to fuck the living shit out of me.
“You like being fucked by a real man?” he asked, his muscular arms sliding under my body, pulling me into him. “And not some fake dick attached to your wife?”
“Yes,” I croaked, nearly unable to breathe under his weight upon me, his balls slapping my hole with each deliberate thrust. “Your big cock feels so good inside me.”
And then I felt it—his cock expanding inside my fuck canal, his balls beginning to throb against my hole. Chaz was about to bust his nut in me and, in that moment, I had never wanted something more in my life than to take his seed.
“You ready for my load?” he demanded urgently, battering my bowels. “You ready for me to breed this quivering cunt?”
“Yes,” I gasped. “Fucking breed me.”
“FUCK,” he growled deeply, a cum bomb detonating inside me. I could feel every shot of his load as his big dick pulsed inside of my bowels, spewing his seed into my deepest recesses. “FUCK—FUCK,” he continued to grunt, his body writhing atop me, consumed by the throes of an epic orgasm.
Chaz stayed within me long after his orgasm had ceased, the last of his seed expelled from his balls. “Are you still hard?” I asked in disbelief.
“Yeah,” he laughed. “I can go multiple rounds before going soft. I hope you like this big cock inside you, because it’s going to be a long night.”
Chaz dumped three more loads in me that night. We skipped the morning session of the conference and fucked our brains out, finally emerging from our hotel room for lunch. I returned home to my family three days later a changed man, my ass sore but completely fulfilled.
My wife and kids threw their arms around me at the front door, welcoming me home. “I’ve missed you,” my wife kissed me. “I’m really wanting to peg your ass tonight,” she whispered in my ear seductively once the kids were out of range.
“Yeah—about that,” I replied. “I’ve decided we’re gonna need to get you a bigger strap-on. I want the largest size available.”
Stories are fiction and intended for readers 18 and up. All characters are assumed to be legal, consenting adults.
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