I Made My Boyfriend Wear My Asshole Boss’s Dirty Underwear [FM]

The hustle doesn’t stop.

I was twenty three years old, fresh from the Midwest to a big city, working in a thankless field where you’re expected to forever pay your dues. Grinding away in the office, running errands, your feet sore as you ride public transportation for an hour so you can pass out in your six story walkup.

I moved to the City with a boyfriend from college. We shared a small apartment with two other roommates. It wasn’t always the most romantic situation, especially since our place was always a crowded pigsty.

Not to mention I was always exhausted from work. I had a boss named Clark who I worked as a personal assistant. He was, to point it kindly, a pampered asshole who claimed to be self-made but came from wealthy stock in toney Connecticut. He was an all-around suburban jerk in his late 30s who liked to pretend he was tougher than he actually was; that he had the kind of grit and preserverance that the City instills in people, even though he spent most of his time here ensconsed in unbelievable privilege.

Clark also held my dream position. And he was good at his job. So I worked tirelessly for him, mostly performing mindless but exhaustive tasks to smooth out his schedule. Clark couldn’t be bothered to answer emails, pick up dry cleaning, make reservations, arrange dogsitters. That was up to me.

Clark kept a pretty dedicated fitness schedule. He would sometimes show up at the office in his gym clothes (A sweaty muscle shirt and shorts) and change. He’d sometimes have me run to the laundromat to have his outfit cleaned that day. He was muscular, good-looking, and seemed to have everything he ever wanted.

Meanwhile, I was paid like dogshit. It was infuriating. Sometimes it was demeaning. I often felt like an overqualified, glorified intern drowning in student debt.

There was a week coming up where Clark would be out of town. He requested that I sit his spacious, high rise apartment (With ample amenities) in his absence. This was honestly pretty exciting because it would give me a chance to have some personal space away from my roommate. Clark also told me that I was free to invite my boyfriend, Johannes, who he had actually met before.

When Johannes and I stayed the night at Clark’s place, we got drunk off my boss’s uber expensive whiskey collection. The place felt massive, nothing like anywhere I had ever lived. The views of the city skyline were breathtaking. Johannes and I, half-wasted off pricey spirits, stumbled into Clark’s bedroom.

One thing I had taken notice of was the half full laundry basket in Clark’s spacious walk-in closet and the conspicous designer boxer briefs that laid on top of the pile. I don’t know why but those soiled briefs stuck in my mind and my lizard brain flashed on them while I was making out with Johannes on my boss’s bedspread. A filthy thought was implanted in my head and the many (badly concocted) old fashioneds that I consumed that night was enough to get me to act on a perverted, half-formed fantasy.

I asked Johannes to put them on. I don’t know why he did it. We’d never done anything like this before. It was probably because we were so drunk, its probably because I remember asking Johannes “Please, lets just try it,” even though he heistated.

So he did. Johannes dropped his tattered Hanes to the floor and reached for Clark’s used Tom Ford silk underwear. He pulled them over his hairy legs, and onto his unshaven musky cock. I felt myself tremble as I scooted close, my nostrils flaring. Johannes hand cupped the back of my head, and pulled me in so that my nose and lips pressed against his now silk-covered balls.

I remember inhaling. Clark’s dirty Tom Fords smelt like stale sweat. I felt disgusting. But I couldn’t help myself. I didn’t know what it was, if it were the whiskey or the weed, but I felt achingly alive in that moment, gushing. My thong was soaked, and I could feel the fabric sticking between my legs.

I started to pull away but Johannes gripped my head harder. I kissed the undersack, my tongue grazing the silk fabric. I inhaled again, trying to separate Johannes masculine musk from Clark’s post-gym reek. But I couldn’t. They blended into a solitary cocktail of cock stink that had me addicted, horny and frankly embarassed.

“Suck that dick, baby.” Johannes was moaning. “Suck it, baby. Suck it.”

I sucked as well as I could: Johannes stiff cock through the silk. I felt like an animal, a pig wallowing in filth. It turned me on. I whimpered into Clark’s dirty underpants, soiled from working out and God knows what. I whimpered into Johannes penis, imagining how he must feel, wearing my boss’s unwashed briefs that smelt of an intense, sweaty gym sesh.

“You like sucking your boss’s dick?” Johannes mumbled in an intoxicated haze. “How does your boss dick taste?”

I was working my pussy as I sucked and kissed the Tom Fords, barely aware of the muffled moans I breathed into the silk. Before I knew it, I was cumming, my body twitching and Johannes was grunting too, saying something like “Oh fuck, oh God, oh fuck!“

I worked myself into an orgasm. And the sheathed suck I gave Johannes through Clark’s used briefs was enough to make him cum too; he sprayed his load into Clark’s Tom Fords, and I felt the sudden warm wetness of the soaking designer fabric in my mouth, and it only made me finish harder.

A few minutes after we finished, I felt ashamed. And frantic. I was worried that Clark would find Johannes’ cum stains in his underwear, even after they were washed. In my panic, I went out the next day and purchased a new pair to replace Clark’s soiled supply, spending nearly three-hundred dollars of my hard-earned money to replenish the underwear drawer of a grown brat who had it all. As someone working for peanuts on the dollar, it hurt. But I couldn’t afford the shame and punishment that would come from losing my job, of dissappointing Clark. I ate the cost, and as far as I knew, Clark never knew the difference.

Source: reddit.com/r/gonewildstories/comments/xxbqbp/i_made_my_boyfriend_wear_my_asshole_bosss_dirty