Would You Get Your Ass Cherry Popped For $1,500 Bro?

Rocco, Bobby Owens

Finally, we get two of the hottest boys on Broke Straight Boys in bed together; Bobby and Rocco. Today, Bobby is going to suck dick for the first time, Rocco, on the other hand, has had the pleasure of being sucked off by a few guys already and as such, is an old hand at oral. The boys slipped out of their clothes and started playing with their dicks. However, like always, Rocco was rock hard as soon as his clothes hit the floor while Bobby looked to be only a minute or two behind him. I gave Bobby a chance to back out but as Bobby said, he needed the money. Now, it was time to get to work so Rocco stood up beside the bed while Bobby rolled over onto his side, legs spread so his hard cock was on display. Eyes closed, Bobby leaned in and slid the cock head into his mouth. Concentrating on the job in front of him, Bobby's mouth slid back and forth over the thick dick even as he wrapped a tight hand around his own cock. Bobby broke off for a moment to spit on Rocco's dick before diving back down. He spit again, pumping the shaft a few times then immediately swallowed the cock head. Rocco wondered if Bobby had a gag reflex and tested it out, forcing Bobby to go down deep on his dick only for Bobby to pull off as he choked. Rocco said Bobby was doing a good job but would be better if Bobby could go deeper, all the while, Bobby was shaking his head in protest to Rocco's suggestion. A moment later, Bobby, at my suggestion, started pumping Rocco's shaft as he sucked on the cock head. Rocco wrapped his fingers around Bobby's long hair and started gently face fucking him, causing Bobby to moan a little at the unexpected show of domination. Jerking himself off again, Bobby let Rocco take control of the situation, holding his head still as Rocco thrust in and out of his mouth. I asked Bobby to lick the head of Rocco's dick and after Bobby did a half hearted effort, I told him to do it properly. Bobby licked a couple of stripes along the shaft of the thick dick, Rocco admitting that it felt pretty good. For something a bit fun, I handed Bobby $500 and told him to count it out as he had a dick in his straight boy mouth. Bobby and Rocco laughed but Bobby dutifully counted it all out before asking if he had done enough dick sucking for one day. I told the boys to just sit back and jerk each other off until they came. However, as they helped each other along, both Rocco and Bobby said that they wouldn't be able to cum from just being jerked off and asked if they could do the cum shot another way.. I asked Rocco if he had any ideas and he said fucking Bobby would help him cum. I thought about it for a minute, then offered Bobby $1500 to get his cherry popped. Bobby was down on his hands and knees, ass raised in the air, almost instantly. As Rocco had a big dick for a first timer, I got Bobby to roll on his side so that Rocco would spoon him from behind. While Rocco got himself prepared, Bobby tugged on his own rock hard dick, asking Rocco that he go gently for his first time. Raising one leg in the air, Bobby lubed up his ass hole, rubbing a finger up and down his crack. Finally, Rocco was about to break Bobby in. Inch by inch, Rocco slowly worked his thick cock into Bobby's virgin ass, all the while, Bobby groaned in discomfort. Jerking on his dick to take his mind off the pain, Bobby had to be reminded to breathe as Rocco started to fuck him. Right away, it was clear that Bobby was in some pain even though Rocco, true to his word, was taking matters very slowly. Breathing deeply, Bobby clenched his teeth each time Rocco thrust into him, Rocco confirming that Bobby had a very tight ass. It wasn't an easy position for Bobby so he flipped over onto his back, legs spread wide as Rocco applied some more lube and slid all the way back into Bobby's ass. Reaching up, Bobby gripped his feet, holding his legs apart even as Rocco started going a little harder and faster. Bobby groaned loudly as Rocco pulled all the way out then thrust back in hard, all the while, jerking himself off. Surprisingly, the entire time Bobby was being fucked, his cock had been rock hard. Only minutes later, with Rocco riding his ass, Bobby climaxed, cum spilling over onto his stomach and into his pubes. Rocco pulled out and tore off the condom, wanking himself off and sprinkling cum over Bobby's dick, balls and thighs.