First time handled

Had today off so I contacted a buddy I hook up with on a regular basis. I cleaned up and out then headed to his place. He lives about a half hour away in a secluded house on five acres. Arriving about 10 am he met me at the door in sweatpants and no shirt. He’s mid 60s 5’6” with a slight beer belly. Dad bod. He offered me a drink and I accepted a beer. He then led me to the back of his house to the pool area, were a couple of lounge chairs with towels were set up with various toys and but plugs arranged in a row with a big bottle of lube sitting on the ground. Told me to undress and start sucking his cock. Going to my knees I took his soft dick between my lips and started sucking with one hand playing and caressing his shaved balls. He became erected quickly then pulled away and told me to get on all fours on one of the lounge chairs. He grabbed the lube squirting some on my ass and some on his fingers. He began with one finger, then two until he had three stretching my hole. It hurt a little at first but I quickly became accustomed as he worked his finger in and out. Driving them deep and holding them there for at least a minute. He pulled his fingers out and I could feel air rush into my body as I stayed gapped. Another squirt of lube on my hole, he picked up one of the toys. A dildo about 9 inches long and 2.5 inches in girth. A squirt of lube on the dildo and a rub to spread it. He positioned it on my gapping ass and slowly pushed forward. It went in fairly easy until it was fully inserted the girth was fine but the length became an issue and I grunted as he pushed all the way in then pulled it almost all the way out, leaving just the tip in. Then push in again. I grunted again then he asked if I was ok. I said “ yes, just go slow and let me get used to it” he left it in and moved in front of me with his dick in front of my face. With one hand he maneuvered his once again soft cock to my mouth which I began to suck on again and at the same time I began to stroke myself until I became sting as a board. His cock was once again rock hard and he pulled away giving it few strokes as he moved in behind me once again. He pulled the dildo out so fast there was a sucking sound and I felt air again entering my ass. He the grabbed the butt plug and squirted a big shot of lube on it. It was huge and I said “ I don’t think that will fit” he said “I’ll go slow” he put the blunt tip to my still gapping hole and slightly pushed it in it hurt right away I gasped and grunted and he pulled it out and gave me a second to recover. He then pushed in again just a little deeper and held it there. Still being on all fours he reached under and grabbed my cock and slowly stroked up and down the full length rubbing the head that had precum dripping from the tip. Another push in some more pain and he waited again for me to grow accustomed to the size. He again rubbed my conclusions while he waited. Finally after several pushes and what seemed like forever he said “ there you go, all in” he had me stand up which was uncomfortable and walk over to the pool. He jumped in and told me to join him but make sure the plug didn’t come out. Holding it in place I gingerly walked into the pool. I began to swim feeling the plug inside me. My erection growing stiff again as the cool water moved it around. He sat on the edge and gestured for me to come over a again suck his cock. Taking it again between my lips I sucked and used one hand to stroke it until it was hard again. About a half hour later he told me to get out of the pool and go back to the lounge chair which my head down and ass up. He slowly worked the massive butt plug out leaving me again gapping, another squirt of lube on my hole and I noticed him putting some all over his hand, first two fingers, then three, then four. His thumb was was tucked into his palm he shoved his hand all the way inside my asshole wrapping tightly around his wrist.