I am 15 m, live in the midwest in a small city. I was saving money for a car after I get my license and I’d been working with Mr. D down the street for a couple of years off and on. Whenever he needed help I did it and got paid. During summers I mowed the lawn, and tended his pool. He asked once how it was going with my savings. I didn’t have enough and was worried. In his living room, he had gay porn, and old woman with young boy porn on he table. Well, I could help you out a lot if you’d help me out. “Sure what do you need” I asked quite frankly anxious to get out of there and start working on something. Mr D was 64, 5ft 9in tall, thin and had a smooth body. We’d gone in his pool many times. Even sometimes naked. “You know I don’t have sex anymore, since my wife died” he said. Yes, I knew but wasn’t sure. He didn’t want to get involved with another woman but he wanted sex. He pointed to one of the open books, an older woman being obviously buttfucked by a young guy. Then he moved some pages in the gay book with an older man fucking a younger guy.
“I’d pay you, I’d pay you well, every time we do something” he said. I asked what he wanted, and he said at first to suck him hard, to let him to to me what the guys were doing to the older woman, and the older man to the younger guy. “Then after that if we want more, if YOU want more we can do more and you’ll make more money. You’ll have enough for your car, license plates, taxes everything”. I wasn’t sure, I even asked if it won’t hurt if he does that to me. He said we’d used his finger first, then two, maybe three, then it probably wouldn’t hurt much. He said the first time would be more uncomfortable but I’d get over that and start to like it soon. IF I got hard while he was doing it, he offered to suck me and let me cum that way if I wanted it. Finally it came down to it. “$500 the first time, $300 the second, $200 the third, and everytime after that, I’ll give you $100”. When I just sucked him off, I’d get $50 as long as I swallowed it all. “You promise it won’t hurt?” I asked and he said he could never tell but that’s why I would get $500 the first time.
He had me strip, and stand in front of him, he’d seen me when we’d swim naked before but he was touching me. My cock got about 6 inches hard and he was jacking on me. “You like that?” he asked. I told him I did. Then he put his mouth on it and sucked me. I told him I was about to cum and he took it in his mouth, showed it to me then swallowed. He was smiling, as I sat down to catch my breath. He took off his boxers and turned around. I honestly never even saw a picture of a cock that big. It was pretty long, later I learned 8 inches, but it was thicker than my wrist. He had given me the $500, I was holding 5 $100 bills in my hand. “I don’t think I can do that” I said point at his cock. “You said you’d try it, and do it just once to see, and you are holding the money.” He said. I offered to give it back. He said no, and took my hand and yanked me to the bedroom. “Lay on your stomach” he told me. “Please, don’t, please I don’t want to, I’ll give you the money back” I was begging him. He reminded me that he sucked my cock and I shouldn’t leave till I’ve given him his pleasure. “I’ll suck yours if you want” I told him. “Yes I know, but then I’m going to fuck you” he said as he was smearing vaseline all over my asshole and pushed a lot of it deep inside. He laid next to me, finger fucking me with two fingers, nothing in terms of how thick his cock was. I turned on my side, but his fingers stayed doing what they were doing, and he sucked on my nipples. Then he forced me back over on my stomach, got on top of me. The first 2 inches made me cry, I was begging him telling him I’d do anything but it hurt too much. It was all the way inside me, and I was being fucked. Fucked like he used to fuck his wife, I was being fucked like the young man in the porn mag.
It took about 15 minutes till he shoved it so far up inside me. I felt the warmth of his cum, shooting out of his big cock. He leaned and whispered into my ear “There now, that’s my little pussy partner. I’m done now, see, you don’t have to do anymore right now, I’ll pull it out now”. Then with a plop, his big softening cock flopped out. He put it in my hand and I played with it, he was playing with my opened up butthole. “It looks cute, nice and used, just like it should be” he told me. He got a mirror and showed me I was opened up probably 2 inches wide back there. He put three fingers in me and I clamped down, then one and it was still opened but not gaping. “Is that blood?” I asked him looking in the mirror. “Yeah a little, it’s to be expected on your first time, you were a virgin and virgins can bleed sometimes, it won’t last long” he told me.
He had me get a cloth and wash his cock and balls for him, then I had to go to the toilet. He stood at the door and watched me cramping and pushing after his intrusion. I felt weird to be watched, his big cock hanging in front of him, started getting hard again. He wiped me up and greased me again and got $ 300 and put it on the bed. I just laid there on my stomach and got fucked again. I put on my clothes, took my money and left, waiting till I was home to go to the toilet. There was so much leaking into my underpants I had to throw them away so my mom wouldn’t see them.
I waited a couple of days, then went back. He asked how I was feeling, it was better I told him and the bleeding stopped. “We should wait another day or two before we fuck again, but I do have $50 for you if you want it” he told me. I took it, he insisted i suck him while both of us were naked, and I sucked his big cock. He shot off in my mouth, I choked a bit, but showed him his own spunk in my mouth then swallowed it all. “Stick around a bit if you want I’ll be ready to do it again” he said. I did, I sucked him again, and then he sucked me off. Two days later I was on my back with my legs wrapped around his butt and his big cock fucking me again, while he was sucking and pinching my nipples.
He’s right, I’m gonna get my car.
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