Chub-Bear Jim's Turn In A Whore

[Tailgunner]

I was a janitor with the education department for a decade. I had started in the high school cleaning up after the snotnoses and then finally improved my lot in life by moving up to the junior college and adult school campus which was also closer to my apartment.

I had known about one student starting when he was in the high school but as with the other kids I wasn't interested in wasting my time other than a polite "How's it going?" in passing. I mostly ignored the kids since most were of low morals, surly, dopers and hoodlums. The adult school and college seemed to have brighter and nicer students. The main requirement was being over eighteen to attend the adult school or college, as well as passing basic tests to enter the college. The student I had known of in the high school befriended me when he was eighteen and a half while attending the adult school. He was pretty good looking, about 6' tall, somewhat slender, and had the long blond hair most young guys seemed to sport back then. I myself was just over 6', 275 lbs, just beginning to bald and gray and fifty-one when we first talked to each other.

"Jim." I said when we shook hands. "Rick." he replied. His hand seemed small in my nail-bitten bear-paw, almost like shaking hands with a woman. It was a week later after our after class chats when he came on to me. I rejected his advances politely but I did help mentor him so he could finish his remedial classes and get into the college. A year and a half later he began classes at the college. I continued to see him since the college and adult school were on the same campus with the college on one side, the school on the other and two middle buildings and the big gym being used by both. Rick was doing good with some of my help and finally graduated from the two year junior college with an associate degree. We hugged on his last day on campus and I didn't see him until two and a half years later.

The thing about that was that although he had earned another degree at the four-year, he was whoring and hustling. I was in town and happened to see him. He thought I didn't know what the area was so he smiled. "Hi Rick" I said as I hid a smirk and wondered why he was selling sex instead of getting a job. "Hi Jim" he replied and we shook hands. He seemed a little dirty, not as kept up as he had been on campus. He had worn a preppy outfit including white shirts, a sweater-vest, dark slacks and leather sandals. On the street he wore pastel shirts, the sweater vest and dark slacks and loafers instead of the sandals or sneakers. He had cut his hair shorter. We talked a while and I saw him again a few weeks later. He then asked me if I wanted to get my rocks off. "I don't pay for it" I told him. "It's on me, Jim. I'll admit I had the hots for you for ages. Now please fuck me" he gushed as I tried to hide my astonishment.

We went to an abandoned parking garage where whores and dopers did their thing. In a somewhat private corner of a vacant parking space between the wall and a seemingly abandoned pickup, he knelt and unzipped my jeans and fished out my uncut dick. I had some cheeze under my foreskin but I enjoyed that great feeling when a good cocksucker licked and ate it from under my hood and off my prick and swallowed it. He ducked his head under my gut, sucked my dick into his mouth and sucked on it while inhaling my sweaty crotch. My dick felt really great as he licked and sucked on it til it was hard. He opened his mouth and pulled his head back. "Want to fuck me up my ass?" he asked. "Sure. But you'll need to suck it clean after I cum" I replied. "No problem, stud" he grinned. I was glad we never kissed knowing what he did with his mouth.

He stood up, dropped his pants and bent over the open tailgate of the old pickup. I spat on his asshole, stepped up to him and inserted my dick up his ass which was quite loose so my dick slid right in. I gripped his hips and hilted myself, flexed my fifty-five year-old love-muscle in him and fucked him. I fucked him easily, enjoying adding the fella to my list of conquests. I pumped his ass for about five minutes, slowly increasing my pace as I got closer to my climax. I grinned and pushed my glasses back in place and continued fucking him. My dick got hotter, closer and my balls drew up, then I then felt my dick swell and again hilted myself, gave some short quick thrusts and blasted my middle-age chub-bear cum up his ass as I held his hips, spurting my jizz up his hole. I held my position for a couple of minutes before pulling halfway out and shoving it back in to pump more spunk into his ass, which was a good cunt, better than most vaginas I've fucked. I thrust again, hilted myself, held my position and then pulled out.

He stood up and thanked me for the fucking. "No problem Rick" I said as I stood facing him. He finally remembered to kneel and suck my dick clean. His mouth made my dick feel good all over again as he licked and sucked it clean. "I need to piss Rick" I told him. He didn't try to pull away so I held his head and soon rewarded him with my afternoon beer-laced piss. He gulped it good without letting any leak out between my shaft and his lips. I was satiated and felt great once he finished drinking my piss and sucking on my dick more until it was clean. He sucked off of it leaving it clean and dry and kissed it and my sweaty scrotum.

"You're a good piece of hole. I'm glad you're doing good for the men" I said, as he stood up. He said he had tried gay sex in the four-year college and got his mouth and ass broken in there. He had been anally raped a month before graduating. He had been whoring since graduating the four-year college he had transferred to after graduating the junior college. He'd looked for a job and after a series of short term jobs and a stint in a small rock band he found that hustling and whoring was easier. "I have a buddy who might want a piece of your ass if you don't mind, same terms" I told him. He asked who it was and I told him my friend Clarence. He knew Clarence but as with me he didn't know the man would just as soon fuck him as look at him. Clarence had said he wanted to fuck him some day while we shot the shit on our lunch break. Rick didn't really want to do Clarence, but since he owed me he capitulated.

Edited December 22, 2012 by Hotload84

[Inception]

I was glad we never kissed knowing what he did with his mouth.

That line almost made me shoot before I finished the story. It`s so hot that he expects the bottom to do something that he thinks is disgusting.

[mike43]

hot story man I would like to be a whore