Becoming A Cuckold

It was the third year of our relationship, and like a fire left untended, our sex life had dwindled. From a blazing inferno to a flickering ember to something dull and ashen. Not that I’d lost my taste for it—God no, I still craved sex like a junkie craves a fix. My fiancée, Lisa, was the same, but timing was our enemy. We both worked soul-sucking jobs at the same company, different corners of the corporate maze. I was in sales, chasing quotas like a dog after a bone; she was in accounting, drowning in numbers. Not sexy gigs, just exhausting ones—stressful in that slow, grinding way that leaves you too tired to tear each other’s clothes off.

We’d stumble home at odd hours, syncing up somewhere between 7 and 8 PM. Our routine was predictable: whip up something decent to eat, crash on the couch with a show or a movie, and every couple of days, we’d fuck. When we did, it was good—sweaty, tangled, switching positions like we still had something to prove. Nothing wild, though—no anal, no toys, none of that kinky shit. Just solid, classic sex, ending with me unloading inside her warm, tight pussy.

Lisa was a knockout in her own way—not a runway model, but the kind of pretty that grows on you. Petite, with dyed auburn hair that wasn’t too loud, a cute face framed by glasses, and a body that was all curves. Plump, not fat, with a juicy round ass and big, heavy tits that jiggled just right. She wasn’t stick-thin, and I didn’t want her to be. I’m a sucker for a woman with some meat on her—something to grab onto when we got down to it. And grab I did, especially that ass. I was obsessed with it. I’d beg her to let me taste it, just a lick of that tight little hole, but she’d shut me down every time. Fucking tease.

Here’s the thing: I’m an ass man through and through. I’d even had stuff up my own backdoor—don’t judge—and loved it when Lisa teased my hole while sucking me off. She’d do that, no problem, which made her anal embargo even more baffling. I’d try to sell her on it, swearing it wasn’t uncomfortable, but she wouldn’t budge. Maybe a dick pounding in and out was different. I wouldn’t know. So I never pushed too hard.

Even with our solid sex, my mind was a nonstop porn reel. I was hooked on the internet’s dirtiest corners, downloading filth weekly like it was my religion. Broadband was my savior—endless streams of depravity, all from the safety of our apartment. Lisa knew I was into porn; we’d watched plenty together. We’d sit on the bed, fire up some tame one-on-one flick, full-screen it, and let it heat us up until we pounced on each other. Fun, sure, but my tastes ran darker. I’d seen it all—every twisted fantasy you can imagine—but what really got me going was white girls taking it from black guys. Especially up the ass. Those massive cocks sliding into tiny holes? Unreal. Naturally, I’d picture Lisa as one of those girls, her thick ass bouncing as some hung stud railed her. I’d spend hours hunting for a redhead who looked like her, getting pounded in every way I couldn’t.

Then there were the hotwife and cuckold sites. If you don’t know, a cuckold’s the guy whose woman fucks other men—ideally with him watching, approving, and eating the humiliation like a bitter dessert. I devoured stories, fake and real, about wives turning into sluts for their lovers while their husbands got nothing but scraps. My imagination went feral. I’d see myself in the corner, jerking off while Lisa got the ride of her life. The kicker? When the husband licked the other guy’s cum out of her pussy. Another man’s load—nasty, degrading, and fucking intoxicating. I was hooked on the idea.

Thing is, I knew it’d never happen. Lisa loved our sex, swore she didn’t need anyone else. She was the most loyal person I’d ever met—cheating wouldn’t even cross her mind. Sex was a bonus for her, not a mission. If it was easy, she’d enjoy it; if it meant hunting down a stranger, she’d pass. Or so I thought.

I was careful with my porn habit. Hours scouring the web, but I covered my tracks like a pro. Movies locked in a hidden partition, browser history wiped clean every time. Lisa would never find a trace—or so I believed.

It was January, fresh off proposing to her over the holidays. She’d said yes, beaming, and we were on cloud nine. But work called me out of town that weekend. I spent Saturday and Sunday in a client’s office, bored out of my skull. The hotel’s pay-TV saved me—flipping through, I found an interracial flick. Tame, but good enough: a blonde getting it from a ripped black guy. Halfway through, stroking myself on the bed, the phone rang. I muted the TV and grabbed it.

“Hello?”

“Hey, sweetie,” Lisa’s voice purred through the line.

“Hi, babe. How’s it going without me?” I asked, grinning.

“Boring as hell watching TV alone. Think I’ll hop online, check out some houses.” We were house-hunting, always on the lookout for a deal.

“Cool. I’m just chilling, watching a movie,” I said.

“Let me guess—not PG, right?” She laughed, and I chuckled too. She knew me—well, most of me.

“Nope. Right now, some girl’s getting her ass drilled by a big dude.”

“You’re such a perv. You and your ass obsession. Be grateful you’ve got a pussy like mine!” she teased.

We bantered a bit longer, tossing love-you’s back and forth like newlyweds. After we hung up, I finished my session, the blonde on screen a poor substitute for the fantasies in my head.

Monday night, I got home to a surprise: candlelight, red wine, a steak dinner—Lisa had gone all out. She was in a tight, low-cut top and a short skirt, hotter than usual. A little slutty, even, which had me hard before I hit the shower. After we ate, polishing off two bottles of wine, she stood up, smirking.

“Jake, time for phase two of the night,” she said, sauntering not to the bedroom, but to the desk where our computer sat. The screen was on, just the desktop. I raised an eyebrow, but she just smiled, clicked the mouse, and up popped a porn flick—one we’d watched before. Basic, vaginal-only stuff, nothing crazy. Still, my dick twitched.

We stood there, awkward for a second, until she grinned wider. “So, Jake, you hard yet? ‘Cause I’m soaked. How about you bend me over this desk and fuck me senseless?”

She hiked up her skirt—no panties, just her bare, dripping pussy. My jaw dropped. Lisa, my sweet little fiancée, was a vixen tonight. I didn’t waste time—pants down, cock out, ready to go.

“Oh, sweetie, you’re definitely ready,” she said, grabbing my dick. “I’d suck it, but my pussy’s screaming for you to fuck it.”

No arguments here. I spun her around, bent her over the desk, and slid into her wet heat. She moaned loud, egging me on—“Fuck me hard, Jake, give it to me!”—and I did, pounding her while gripping that perfect, plump ass.