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I'm Letting My Best Friend Take My Butt Virginity On Camera

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Mike Robbins, Josh Stuart

Mike and Josh are back, once again, in the Broke Street Boys studio and this time, things are going to get serious. Josh had to visit the doctor again in regards to his injured foot which cost him about $300 and he still needed to get some more money to put towards the new ATV so I told him that, in order to make more money, one of them was going to have to bottom. Mike said he was going to top while Josh bottomed. I told them they would both get $1000, with Mike saying he would give Josh $500 so, in the end, Josh would make $1500. Josh was not happy, saying he had fucked his girlfriend in the ass and she had complained about how much it hurt.

However, Josh did admit that his girlfriend would stick a finger up his ass on occasion and that he quite liked it but with a final price of $1675, Josh said he would give it a try. The boys stripped off naked, sitting back down on the futon. After a bit of discussion, Josh and Mike decided that they would go with some gay porn so that Josh could see how it all goes down. Mike sucked cock first, leaning over and swallowing down Josh's dick as Josh just sat and enjoyed his buddy's mouth. For Josh though, the thought that he was going to be fucked in the ass was really playing on his mind and he was finding it difficult to stay hard during the blow job. Josh wanted to get down to the fucking but Mike decided he wanted Josh to suck his dick so Josh sucked on Mike's hard cock. Josh was a bit more confidant this time around but he was still quite nervous about a dick in his straight boy mouth. However, he was doing well, Mike panting for more as Josh put his newly learnt tricks to the test. Josh licked up and down the hard shaft, sucking on just the head of Mike's cock and even tried a bit of deep throating. Finally, it was time for Josh to get fucked even though he was still quite hesitant about the whole idea, especially about the size of Mike's dick. I handed Mike a cock ring as Josh's ass was going to be super tight and Mike needed to keep hard.

The boys opened up the futon and with lube, condom and cock ring all applied, Josh got down on his knees and elbows with Mike kneeling behind him. Mike was made to go slow as it was difficult for him to penetrate Josh's virgin ass, Josh breathing deeply so he didn't clench up. Josh was taking his first cock pretty well, just riding out the initial discomfort as Mike slowly rocked back and forth. Mike was loving the cock ring, saying he was going to buy one for himself, speeding up his thrusts as Josh started to loosen up. Josh flipped over to on his back, Mike holding his legs spread wide and sliding right back into Josh's ass. Although it was a better position for Josh, it was obvious he was still feeling some discomfort but there were hints that he was experiencing some pleasure as well. Mike was able to speed up and start riding Josh's ass even as Josh jerked himself off, both boys moaning and panting.

Mike told Josh to hold his legs up, Mike pounding into the tight ass in hard strokes. A slight change of position and suddenly, Mike pulled out, jerking off on Josh and spurting cum all over Josh's chest and neck. Josh grabbed a towel and cleaned himself up before leaning back on the futon and wanking himself at a furious pace, cum shooting over his chest before dribbling down his shaft and fingers. Both boys were exhausted by their workout with Josh saying that bottoming wasn't that bad. Josh and Mike will be back in the future and who knows, maybe Mike will bottom for Josh one day?

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