As ever please donate to nifty.org. it is a rare and precious service for all of us cock hounds. Now here's a story.
That time my boss fucked me.
This is a true story. While I will change the names and keep locations vague, I will try to make the nitty gritty as close to the truth as I can. It was a very formative sexual experience for me, or perhaps it's better to say that it was a revealing experience, as it was the first time I truly experienced a side of myself that I came to love.
I was a student at the time, second year, heading for an underwhelming undergraduate degree unless I really pulled my socks up, (I did pull them up a bit and avoided humiliating myself that way). To get more money, and force myself to be more confident and sociable, I got a part time job at a lively restaurant and bar near the gay quarter of town. It was a pretty mixed place, about fifty fifty in terms of straight or gay or whatever, both in the customers and staff. Looking back it was a rare kind of experience, to be immersed in a place that had such a relaxed attitude to variety.
At the time the place was run by a general manager I will call T. Looking back I realise that my gaydar was woefully underdeveloped at the time because I took him for a standard, competent and, most of all, straight older manager guy. Not that we interacted much anyway, he would work mostly in the back office, while I was usually on the bar, and most nights I'd only see him when he came to collect and count the takings. Since I was, though I say it myself, a diligent employee; polite, well presented, punctual, he never had much reason to interact with me. Not that I minded, I'd always been a bit tongue tied around authority figures anyway.
The first time I got a hint of anything more, that not only was he not as straight as I'd assumed him to be, but that he also had his eye on me, was one evening as I was preparing for my shift. I was stood in my work trousers, bare above the waist, and was about to pull my shirt on when T walked through the staff room on his way to a storage cupboard on the other side. He stopped and turned to me before making a comment about the belt I was wearing.
"That looks a bit kinky for you." He said. It was something to that effect. To be fair my belt was one I'd picked up in an alternative clothes place, and was lined with small, steel studs. I can't remember what I replied, something dumb I expect, and turned and caught his eye. I'll admit I was naive back then, maybe still am, but even I could see the wolf behind his eyes in that moment, and in his smile, sharp with what I guess was anticipation. The moment didn't last long, but I looked at him a little differently after that.
It was a fairly open secret that T was unhappy in his job. I couldn't blame him really, in the few encounters I'd had with the owners of the business I'd already decided that they were both unbearable. The less said about them the better. So it was no surprise when word got around that T had found another job and would be leaving at the end of that month.
By accident or, looking back, more likely design, I was on shift for T's last night working, along with a couple of other lads (one a cute, charismatic Irish lad, the other a "straight until after a few pints of Stella", gay boy's wet dream scally type lad, but enough about them. I'm sure they don't perk your interest at all...hehe. Maybe another time. This is about me. And T).
We finished up cleaning down the bar before clocking out, then hung around for a few after hours drinks. It was a chill, affable atmosphere, and the conversation was occasionally racey enough to make little clueless me blush and squirm from time to time. As the youngest and the newest employee, I took the expected role of butt to their gentle hazing, and felt good to be included.
As the night progressed we moved on to a nearby club. It was your typical loud, badly lit, sticky floored gay club you can find in thousands of towns around the world, known for being open late and having cheap drinks and cheaper men.
The club really wasn't my scene, then or now, but the pints in my belly and the good company had me actually enjoying myself. It was around then that I began to notice how close T's attention had been on me, pretty much all evening, and was only getting closer and more intimate as the night went on, and as he bought round after round at the bar.
I was leaning against one of the shelves they have for drinks near the edge of the dance floor, watching the people dance. T was stood close. He was so close I could smell his after shave and the hint of the night's sweat beneath. He was asking me something, his lips so close to my ear that the words tickled. I have no idea what he was saying, or asking, I just know that when I turned to him his face was still a breath away, and that wolf was back behind his eyes.
Without another word he leant in and pressed his mouth against mine. It was a shock, let me tell you, but I was utterly disarmed, paralysed. I'm not sure by what, maybe shock, maybe fear, maybe arousal, maybe all three, but for moments I stood there as his lips, lightly stubbled, raked my skin and his tongue pushed into my mouth.
Before I knew it he had his hands either side of me, holding on my hips and using his weight to press me back against the wall until I felt his crotch pressing into the top of my thigh. He made no attempt to hide that he was getting hard, and I could hardly blame him for not being ashamed of what he had. I'd find out more later, but I knew then he was bigger than any of the guys I'd dated up to then. I didn't fight it. I let his tongue invade my mouth, his hands grope my body, pushing my shirt up and running his thumbs on the bare skin of my belly as he pushed that beer can he had in his pocket against me.
I don't know how long we were like that, him eating my face, practically humping me through our clothes, but by the time we broke apart the decision had been made, I'm not sure by who, that I was coming back to his place.
A car journey later followed by a ride in the lift and we were in his flat and in his bedroom.
"Strip." He'd told me, and I did, and stood naked before him, my dick standing out like a sapling. Perhaps it was because I already knew T in a different context, but being naked for him felt transgressive in the best way, like I was doing something outside of the normal rules. He looked me over hungrily as he removed his own clothes. His body was decent, not a gym rat by any means and had that dad bod vibe going that would later become so popular. And his dick....I didn't stop to measure it, but I'd have eyed it at at least eight inches, uncut, and at that moment semi hard and growing. He pulled me onto the bed.
"Let's see what you can do." He said, before pushing my head towards his cock. I did my best with that thing, opening wide, keeping my teeth away, but boy it was a struggle. I found out later that I'd actually done a good job, but at the time I felt I was struggling just to get it wet. Perhaps he was used to bad blow jobs, and my obvious eagerness made up for it. That's when he went for my ass.
He'd pulled me around so that my butt was close to his face before grabbing it and pushing a finger at my hole. I was tight as hell back then, still am though I'm better at relaxing now, so at first he was knocking but no one was answering. He spat on my hole a few times before trying again, slipping in one finger, then two, working them deeper, all the way to the last knuckle. I moaned and winced and squirmed, not sure yet whether I liked it or not. T didn't relent, and that just turned me on more. My previous lovers, the few guys who'd fucked me, had always been so thoughtful, so communicative, and it made me sick. At last a man was just taking what he wanted and either didn't care if I struggled, or liked it when I did.
T shifted me onto my back and lifted my legs so that my knees were by my ears. I knew what was coming and shivered. He loomed over me, a slight smile on his lips, as he rubbed the head of his cock, slick with spit and precum, at my tight little hole. He pushed forwards and I grit my teeth and grabbed the bedclothes. I remember talking but I can't remember what I said. "Shit. Fuck. Shit." Something like that I guess. I took it, though. I was a good boy and suffered through it. I couldn't have articulated it at the time, but even then I wanted to please him, to make that big dick of his feel good, to make him cum, so I rode the pain it caused me.
When I say that I had been fucked before, that wasn't quite true. Sure, a few guys had put their dicks in my ass and moved it around, but in retrospect T was the first man to really fuck me. At the moment his balls kissed my ass, his mouth kissed mine, a deep, hungry kiss as he slow fucked me, pushing me through the discomfort towards something I hadn't felt before. Perhaps it was his size, perhaps it was the fact that, until that night, he had been my boss, or perhaps he just knew what he was doing (I suspect all three), but I soon found myself melting under him as we dicked me deeper and harder than I had ever been dicked. It was hard, sleazy, animalistic and I loved it.
Events begin to blur in my memory after that, thanks in part I'm sure to the bottle of poppers that T had produced from somewhere and would hold under my nose, holding one nostril closed and telling me to sniff. That was a first, too. I had maybe tried poppers once at a club, but had no idea about their association with gay sex, and no real idea about their effect until it hit me. It was as if all my inhibitions vanished for those moments, and everything in me wanted to be the bottom slut he clearly desired me to be. My head span with sensations, his weight on top of me, his hot breath on my skin, his thick cock relentlessly pounding now, hiting that spot that made me tremble and whimper in his arms. I was so lost, so his, and he knew it.
"You love it, don't you?" He hissed in my ear. He had flipped me onto my stomach and railing me from behind, his arm held around my neck.
"Yes...."
"Say it."
"Ah..." A hard thrust to centre my attention.
"Say it."
"I love it..."
T fucked me like that for a long while, talking dirty in my ear, getting me to admit ever dirty thought I was having. It felt so good, so hot, to tell him the thoughts, the cravings I'd had and never spoken about, how I loved the way he man handled me, forced himself on me, dominated me, fucked me.
"Slut." He said that a lot, and every time he did so I was more his. T bent me into shapes I didn't know I could make, fucking me all over the room until we ended with him on his back with me riding his cock. Our eyes were locked, skin adhering with shared sweat. He halted his pounding and let me ride him.
"You want it, don't you?" He asked as he teased me with a few hard thrusts.
"Yes....I want it." I moaned. He held my eyes.
"Yes what?" I knew what he wanted me to say, or at least guessed it, but for some reason I hesitated. Impatient, he repeated his question, punctuating it with another jab to my guts. "Yes what, slut?"
"Yes sir....I want it." That was it. T smiled.
"Good boy." He said, and gave me my reward.
I don't know what time we finally fell asleep, but i woke his bed, sunlight sneaking in around the blinds, my ass sore, the cheeks kinda glued together with T's dried cum, and T still dozing next to me, spooning me, his soft cock resting against my ass. If I didn't have morning wood already I definitely would have gotten hard anyway as I lay there, remembering the night and feeling the dick that did it to me so close. Soon I felt T stir. He reached lazily around me, his hand finding my hard cock and giving it a squeeze. I felt his fat dick swelling against my ass and he mumbled something I couldn't make out. Soon he was full hard and resting along the crease of my ass. T started humping, working the head towards my hole.
There wouldn't be any preparation this time. After lining up he pressed in, forcing the head of his cock into my sore ass. The pain was sharp and sudden and, without the anaesthetic effects of the alcohol and poppers I yelped and pulled away, trying to escape him. T increased his hold on me and used his weight to force me onto my stomach, his cock still at my ass. I wasn't getting a choice, he was gonna fuck me dry and raw. Consent was implied but not stated, and it's the closest thing to rape I had experienced.
The fuck that morning was rough, uncomfortable and purely about his pleasure. It didn't last long, thankfully, perhaps ten minutes before he added another load to the two or three he'd put there the night before. He even jokes about it later on, "sorry for raping you this morning" like it was nothing.
I met up with him a handful of times after that. We even tried to date, but it was clear that, outside of the bedroom we had nothing much in common and no spark beyond the sexual. He was the first guy to lock me in chastity, and to shave my body hair, but I think that will be a story for another time.