First time for me was a few years ago. The guy that owned the pizza place lived up the hill but directly behind our house. I wqas trimming the weeds with my dad's weedwhacker on a hot day and I was a complete weed covered sweaty shirtless fool. I could see Gary (Pizza Owner) was out by the pool sunning himslf in a little speedo. He was in his 50's, hairy and very tanned. As I was taking a quick break refilling fuel in the weeder he came up to the fence and said something about how refreshing it was to see a young man working hard. I told him I didn't have much choice because my dad had asked me to. He offered me a lemonade but I told him I had to finish this job but instantly I knew what he wanted. I did too but I had to finish this. after 30 minutes or so I was done and Gary came out with a cooler with ice and a couple of beers and a can of lemonade. He was still in only his speedo. He was not too tall and stocky with a pretty round stomach. It seemed he had a big package but who really knows until the moment of truth?

Anyway I wasn't shy and I asked him if I could jump in his pool. He said if course I could and there are some trunks in the pool house. I went in and dropped my shorts and kicked off my shoes in two seconds. I found the trunks but had a better idea. I came out naked wrapped in a towel. Already I had a promising hard on which was pretty obvious through the towel. I then told Gary the trunks were too big and if he didn't mind I'll just dive in with the suit God gave me. I quickly lost the towel and jumped in. As I came up for air I told him to join me and he was just about to jump in and I asked him since I was naked he should be too. I really just wanted to see his cock to see what I was getting myself into. His cock wsa semi hard but I could tell it was going to get big 7.5 or so.

Gary jumped in and then it was on. We stood in the shallow end making out and fondling each other. We took turns sitting on the side so we could suck each other. After 5 minutes or so I wanted to be in a room and I wanted cock in me. I never had before but the time was right. Gary had lube and I made him use half the tube cuz I was scared to death of the pain. SIlly me, once his head was pushed inside it was like this is what I am supposed to do. I couldn't get enough, the only problem was Gary wanted to cum every 2 minutes so I had to pull him out and start again. After me climbing on top of him and he plowing my ass with me on all fours we built a pillow tower and I laid on top of it so my butt was 2 foot in the air. That is when Gary approached me in a lazy dog position and fucked me til he came inside.

Then he kicked me out!

He was worried his wife would be home soon.

What an extreme but it was a great time and as much as I like being a top I will always love bottoming.

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Very hot Carlo - you did not say how old you were but clearly you were braver than I ever was!

And amazing how it felt right to you from the first time. I was very happy my buddy came fast the first time as my ass could not have handled a long pounding!

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I am now 58 yrs old and took my first load in my ass when I was 13. I grew up in the Bronx. Attended a catholic elementary school which was taught by a group of nuns from central america. They would take turns working in the office and would leave the class alone for an hour or two with a reading or writing assignment. One day the boy in front of me turned in his seat and said he had something to show me. He pulled out his cock and started stroking. It didn't take long for a bunch of us to get into comparing dicks and circle jerks. We were 11 at this time. A group of us would get together after school and jack each other off. One day Daniel brought over a magazine showing blowjobs. We all tried sucking but I was the only one who loved having a mouthful of cock. I became very popular. When I was 13 I was spending the night at my friend Louis' house. His parents were out and his older brother was home. I was sucking Louis' dick when his brother walked in on us. He told me to suck his cock. He had about 8" and it was rock hard. He shot in my mouth and told me to get back to sucking Louis. He positioned me on all fours on the bed and pulled down my pants. He spit on my ass and his cock and then just pushed right in. I now had both cocks in me. One in my mouth and the big one in my ass. It hurt like hell but my cries were muffled. He fucked me until he shot inside me. He then had louis try my ass. He came twice before pulling out. We continued to get together regularly.

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