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I informed him that I would go slow and that I knew his body well enough to know if the pain was too much and that he was too trust me. He murmured o.k., closed his eyes, and slumped against the table. After generously applying more lube, I moved in behind him to get ready. It was at that moment that I thought he might be right, that thing was huge. I gently squeezed and massaged his cheeks around the head of the dildo and slowly began pushing it into him. He was loosened enough from the previous dildo so that his ass accepted the new one, but I could see how much more it had to stretch and I could feel his apprehension under me. I went very slowly and it actually took several minutes for the head to pass his sphincter. He moaned loudly as it slowly began to enter him. I could tell he wasn't relaxing like he normally does but boy was this starting to look good. The site of that huge dildo slowly sliding into his ass got me going again. I held back though so as not to be to rough too. ”“Hey, no...” Matt began to protest until he felt the gun to his head.“Don’t tense, relax.” Matt heard the voice say while he was being bent and held over a table, “It’ll make this easier.”Matt felt the lubrication of the condom rub around his puckered sphincter and he immediately became tense.“Fine,” the voice chuckled, “have it your way, I prefer them tight anyway.”Matt grunted his discomfort as his anus stretched to accept the bulbous head of the invading penis and found little, if any, comfort when the head passed through and his anal muscles tightened around the narrower shaft, which felt endlessly long going in. “Now the fun part.” the voice warned as he felt the back and forth grazing along his prostate and rectal muscles. As his ‘lover’ (?) quickened his motions, Matt found it easier to relax. He wouldn’t say he was enjoying it, but it wasn’t as uncomfortable as he thought it would be.“Look at this,” a new voice laughed out as Matt’s erect dick was grabbed by a gloved hand,.
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