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I Was a Serial Cheater: My Biggest
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I've always been the reserved type, the kinda shy but cute Latina girl with dark features, and a body that's more curves than angles. But something about that business trip to Chicago flicked a switch inside me. It was the last night of our managers' conference when I found myself alone with Byron, the company's new, talk-of-the-office hunk. He was this towering presence, a redhead with muscles rippling under his shirt and a big beard that just screamed raw, male energy. The rumors were he was packing serious heat, and though I wasn't usually one to chase after size, my curiosity was piqued.

It was our last night in town, and we decided to break away from the company crowd and do our own thing. We explored the city and bar hopped until we were making out between waiting for the next round and our turn to sing karaoke.

Later, in his hotel room, I lied that my longtime boyfriend and I recently broke up. He didn't seem to care regardless, I don't know what made me say it.

When Byron started stripping, his ripped, ginger body coming into full view, my heart raced. And then he dropped his boxers. Holy shit, the rumors didn't do him justice. His cock was a glorious sight, thick and long, a challenge I was suddenly scared to take on.

I dropped to my knees, taking his heavy dick in my hand. I could barely wrap my fingers around it. Looking up at him, I took the head in my mouth, swirling my tongue around it, tasting him. He talked dirty to me, called me a "cocksucker", with his fingers weaved into my hair, fucking my throat. I tried to take him deep but I have a weak gag reflex, my eyes watered, but I did the best I could.

Then, Byron had a wild idea, at least it was at the time to me – he wanted me to sit on his face. I'd never done that before, but the booze and the spell of cheating sex had me feeling free. Climbing onto the bed, I straddled his face, my pussy hovering just above his mouth, taking a second to tease him. The moment his tongue touched my clit, I squealed. He ate me out like a man starved, his tongue dipping into my pussy and doing circles on my clit, driving me crazy.

When it was time for the main event, I climbed on top of him, guiding his thickness into me slowly. It stretched me in ways I'd never felt. It was a mix of fullness like my tummy was full of water, and a deep ache that he kept agitating in my depths. There was some pain, but I didn't want him to stop. I'd hooked up with one hung guy before, but was too drunk at the time to really feel it. This was different. He was hitting spots in me that haven't been touched by a man since.

Eventually, Byron flipped me over, taking me from behind. He was gentle at first, but soon his cock drilling into me, making me scream no doubt waking the guests on the other side of the thin room walls. I could feel his balls slapping against my clit with each thrust, I remember that vividly.

We ended up hooking up again the next morning before leaving for the airport. It was hard, fast, and left me walking funny. When I got home I had to lie to my boyfriend and tell him I had cut myself shaving down there, so he wouldn't try and fuck me and maybe feel that I had been penetrated by a bigger man. I gave him my ass instead out of guilt.

I did kegels for a week but I must've been throwing up red flags because he ended up going through my phone and finding a text to my bestie where I was stupidly bragging about the hook up. My boyfriend and I broke up rightfully to figure our shit out (he was no saint) and we circled back to each other eventually, and are still married.

A couple of my friends hooked up with Byron as well, but they don't know I've fucked him. Every time his name comes up, my husband subtly nudges me. He ends up dragging me to a bathroom and fucking my brains out. It's never said, but I know it's because he's thinking about me being railed by a hung man.

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10 months ago