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Originally published in the August 2006 issue of Handjobs Magazine
Riding Bob By Bacteriaburger
My first real job (after delivering papers) was at a fast food restaurant out on the highway. Of the three managers who worked there I was fond of two -- the lady who'd hired me and the lady who'd trained me.
And then there was Bob, who was easily my least favorite manager. He was crude and liked to razz the crew around - me especially.
"How's school, Cort?" he once asked my friend and co-worker. "You gettin all the girls?" Then he turned to me. "What about you, Stevie? You gettin all the boys?" He thought this stuff was hilarious, but it just pissed me off.
Even worse was that he was a totally hot and masculine guy. He was in his thirties, with dark, buzzed hair and rough stubble on his face. He had a big, nicely-built body, and I had a hard time averting my eyes from the firm ass in his work trousers.
One time he caught me checking him out -- I'd been helping him load up the cooler, watching the muscles in his hairy arms as he lifted boxes; his pants stretching across his plump butt mounds as he set them on the shelf. I must have been staring too long because when I looked up, Bob was smirking at me.
"Like what you see, Stevie?" he said. I just glared at him. My sexuality was a source of endless torment for me at this time, and I hated being called out on it.
Then one night, Bob and I were scheduled to close together. Cort had just left his early shift when a bus full of football tailgaters pulled up. It was insane. Bob and I were sliding around on the greasy floor, rushing to get everybody served. By the time we locked up, I was exhausted.
I was emptying the grease out into the dumpster out back when I heard Bob yell. I came back in to find him on the floor, grabbing his thigh, his face screwed up in pain.
"Fuck...fucking leg cramp...I get them really bad in my thigh." I helped him up and we hobbled to the manager's office. He sat down and took off his pants. "I gotta work it out, there's no other way...Ah! Holy shit."
He wore a pair of white briefs. I tried not to stare at his meaty thighs, the way the hair swept all the way to the bulge in between them.
Bob was using both hands to massage the muscle underneath his thigh, but he was still having a rough go of it.
"Shit, Stevie, would you do me a favor? Clear some of this stuff from the desk, I need you to work this knot out for me."
"I guess I can try."
"Whatever, it'll be better than what I'm doing."
For some reason, he took off his shirt. Then, rearranging the stuff on top the desk, he laid face down upon it. I gazed for a moment at his broad back and the juicy mounds of his butt under the combed cotton of his briefs.
I felt the knot almost immediately -- it was incredibly tough. My fingers were very close to his ass as I worked them against his smooth flesh. I couldn't believe I was getting this intimate with my hot manager.
"Ahh...fuck...you're doing a good job. Get that lotion from the desk drawer, it'll help."
After a while, I could feel him start to relax. His breathing changed. I let my fingers start to flirt with the area where the seam of his underwear met his leg.
There was definitely a sexual charge to the air, but I couldn't tell if it was just me.
"Hold on a second," Bob said, and he slid his briefs down over his ass. His gorgeously hairy mounds bounced into view. "Can you take them down the rest of the way? Yeah, that'll make it easier."
How that made it easier I couldn't say, but it certainly facilitated my ability to ogle his beautiful ass.
I kept massaging, slowly working my courage and my fingers upward. Bob sighed and spread his legs a little. I took a deep breath and started working my greasy fingers against his ass muscles.
Gently I spread his big butt until his pink, sweaty hole came into view. Bob sighed again. I was rock hard in my pants. I massaged up toward it, working my fingers against the firm space underneath his balls. When my fingertip made contact with Bob's hot asshole, he let out a full-on moan.
He turned over. His cock, which I'd never imagined would be so big and thick, lay like a pipe against his stomach. He grinned at me, holding it up.
"You want to sit on it?" I nodded, but could still only stare. "Go ahead and touch it, man." I took it in my hands and stoked him. The feel of his tool almost made me lose it -- it was so hard and hot. I'd never felt another dick before, and this was like the hugest donkey dick of my dreams. Bob's eyes rolled back in his head as I worked it up and down.
He reached forward and unbuckled my pants. They fell to the floor, my hard dick jutting from the fly of my boxers. He took it in his hand.
"Yeah, man," he said, stroking its diamond-hard length. "Turn your ass toward me." He got a finger wet in his mouth, spread my cheeks open, and touched his wet finger to my hole. He pressed firmly until the tip sank inside. I'd had some stuff up my butt before, and Bob's finger slid in easily. "That's so tight. Are you sure you're going to be able to take it?"
I wasn't sure, but I was eager to try. I got up on the desk, straddled his body, and put some lotion on my asshole. Resting my anus against his cock, I sat down on him; slowly at first, then gaining more confidence until his whole dick was in my ass and I was sitting in his lap.
"Holy shit, holy shit," Bob kept saying. I braced myself by holding on to his beefy torso, and started to ride him. I couldn't believe how good it felt; I'd always figured that it would hurt a great deal the first time. But Bob's dick fit in my ass perfectly.
He started thrusting into me, and I pushed back, relishing the feel of his dick driving in and out of me like a piston. Reaching up, he pulled my head down to his and started kissing me. All the pent-up anger I'd had for him seemed like it was being released. My manager and I were fucking like lovers! It was just too crazy.
"Ah! Ah!" he hissed suddenly, and pushed me off of him. His cock came out with a pop. "My leg, it's cramping up again." He massaged it some more and that seemed to help. "We need to do this standing up. We can do it outside by the boxes. You ever done it outside before?"
"I've never done it at all before."
"You serious? I got your cherry?"
"Yeah."
"Wow. I can't believe it." There was a tinge of sarcasm to his voice, as if he couldn't believe a fag like me hadn't been fucked before. But then he slapped his arm around my back and pulled me close to him. "You're one hot fuck," he said. "We're gonna have a lot more fun at this job from now on. C'mon." He led me, naked, out of the office.
The night was quiet. We went to an area around the corner from the dumpster, where the disassembled boxes were stacked. It was protected by a fence so nobody could see us. Bob had me brace myself on the stack, and slid into me from behind. It felt even better this time. He fucked me gently, but with force. He kept his big arm wrapped around my chest, feeling up and down my smooth torso. With both arms he held me close to his body, rubbing that wonderfully hairy chest against my back as he drove his cock in and out of my hungry ass. He kissed and licked the back of my neck.
Through a hole in the fence I could see the highway. Cars would occasionally stream past, making lonely sounds in the warm night air. Bob took my hard dick in his big paw and started stroking me in earnest.
"You gonna cum for me, baby?" He put his tongue in my ear. "Fuck...can't hold off. I'm gonna cum in your ass, is that okay baby? Gonna cum in your sweet ass." He kept stroking me as he plowed into me, hard, sending jets of hot juice deep inside my butt. He bit the back of my neck, his moans going out into the dark night. Then slowly, he came down.
He turned me around and, dropping to his knees, took my cock into his mouth. I was on the edge in no time at all.
"I'm gonna cum," I told Bob, but he just kept sucking. "Oh...fuck...AH!" I screamed, and I filled his mouth with come. Bob slid his lips up and down my tool, getting off every drop of juice. When I was done he stood up and kissed me, sliding his come-covered tongue into my mouth. I kissed him back, sharing my load with him.
"Fuck, Stevie," he said once we'd gone back inside. "Why didn't you just tell me you liked dick?" Try as I might, I really could not think of an answer to that one, so I just smiled and continued to put away the condiments. I felt good, better than I could ever remember. Not only was Bob's hot body mine from now on, but I knew he'd never bother me again. I had ammo on him. I had a leg up.
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