There is only male on male sex in this story but there is some talk of hetero sex. If this bothers you, please read something by one of the other great authors here. If not please enjoy.
This is my first attempt so constructive criticism is appreciated.
This is a story that started many years ago. When I was younger, I had a friend named Tom who I hung out with. We would have sleepovers now and then or swim in each other’s pools. My parents liked Tom and never had a problem with me spending as much time as I wanted with him even though he was three years older. Naturally there was some experimentation at these sleepovers. While I was at college Tom moved away and we lost touch.
Fast forward almost years. I was doing my grocery shopping and ran into Tom. He had moved back to the area about 10 years ago and lived about 20 miles from me. He didn’t look much different than last time I saw him. He was about 6’2 and solidly built with just a touch of gray and a few wrinkles around his eyes. He just turned 60 but you wouldn’t know it to look at him. I however have put on a few pounds but don’t look my 57 years. We exchanged numbers and agreed to get together sometime. He called about a week later and asked me to come over Saturday to see his place and enjoy his backyard complete with a pool and hot tub. My wife was busy, but I said sure.
I headed out to his place Saturday afternoon with some cold German beer. He lived in a nice 2000 square foot ranch on about an acre of land. It was an older home with large trees and bushes and when we got to the pool area it felt like you were at your own resort. Nice and quiet and private. We sat and started drinking and talking about life since high school. He had married and divorced twice and had a daughter who had nothing to do with him unless she needed money. I told him about my wife and daughter. We were two guys in our late fifties who lived rather successful lives. I had retired comfortably, and he still ran a successful business.
It was hot and we’d been talking for over an hour, and he asked, “Do you want to go for a swim?”
I said, “Sure.”
He said, “Hey remember how we used to swim at night when it was just the two of us?”
I said, “Yes” and started to undress.
We always swam naked later at night when we were kids. As we were getting undressed, I noticed Tom’s large cock spill free as he pulled down his underwear. My mouth started to water as I remembered how good that big cock felt in my mouth and ass. He noticed me looking and said, “It’s gotten about an inch longer since I last saw you.”
Holy crap that thing was a monster back then, I can’t wait to see it hard. We swam and talked for a while and finally decided to get out and dry off. We didn’t have any towels outside, so we sat for a few minutes and let the heat dry us. While we were air drying, I asked him if he is still bi since he had been married twice? He told me he was and still saw his second ex-wife from time to time and had sex with her and her husband. He told me they always got along in bed, but they just couldn’t live together.
We were mostly dry by now but went inside for some towels to finish drying our bodies and hair. After we were dry, he showed me his office which a computer with a 32 inch monitor. He opened a file, and it started a slideshow which were three naked people in a bedroom. He told me this was the last time he was with the ex and her husband. There were about 50 pics altogether. There were pics of the two of them on their knees sucking Tom’s big cock, Tom fucking his ex dogstyle while her husband was under her in a 69, and my favorite, Tom fucking the husband dogstyle while the hubby ate his wife. Hot. I had wood looking at the pics. Tom noticed and remarked that I must still be bi too.
Tom grabbed my dick and led me to his bedroom. Notice how mine is a dick, but Tom’s is a cock? That’s because mine is a little under 6 inches, or about average. Tom’s cock is a large, majestic organ. It’s long and thick and veiny. When you hold it in your hand you can feel the weight of it. Tom’s cock was the first I ever touched, the first I sucked, and the first I ever had in my ass. He also the first person to touch mine.
When we got to the bedroom, Tom asked, “Do you want to suck it? You’ve been staring at it since we got naked.”
I just dropped to my knees and started sucking. At the beginning I could only get the bulbous head in my mouth but after a few minutes I was able to take about half of it. Tom seemed pleased moaning appreciatively every now and then. I tried to take more but would gag. He told me not to worry I’d be able to take it like I used to. I just sucked what I could without gagging and soon I was rewarded with a huge load of cum. It was a lot to swallow but I got it down.
I got up off my knees and sat down on the bed. Tom said, “It’s been almost 40 years, but you still handle my cock like a pro.”
I asked, “How big is your cock now?”
He answered, “Just under 10 inches.”
That is by far the biggest I’ve ever had. He was a little over 8 inches when we were younger and that seemed impossible, but with a lot of patience I was able to take it all in both my holes. I remembered back to the first time he fucked my ass. It was one of our sleep overs and we were both excited to try. I sucked him to full hardness while slobbering all over it for extra lube. He dabbed a little lube on my hole and told me to sit on it and go slow. I was reverse cowgirl and took it very slow. It took about 10 excruciating minutes but finally he was all the way in. After a few minutes to get used to that big pole in my ass it started to feel almost good. I started to bounce up and down a couple of inches at a time. Doing that for five minutes was starting to feel pretty good and I was raising up a little farther each time. Tom told me to spin around and face him. I began to rise off of him, but he told me no, to just sit down and spin around till I was facing him. While I was turning both of my legs were off the ground for an instant and it felt like his cock went even deeper. I didn’t think it was possible. He started to move me up and down and back and forth. I got this super warm and tingly feeling in my balls. A river of precum leaked from my dick.
After a few minutes of this Tom reached up and grabbed my dick and started stroking it. I started shooting cum almost immediately. Some shot up and hit Tom in the face. The rest landed on his chest and stomach. I later found out his big cock was giving me a prostate massage while we were fucking. It happened many times after that. I was spent but Tom hadn’t cum yet, so he was moving my ass on his dick and soon he raised up, driving even deeper into me and exploded. I could feel him shooting into me. We both sat there for a minute to catch our breath and then I kind of slid off and laid down on my side. I knew I wouldn’t be sitting for a while. Tom got up and cleaned himself off and brought me a towel to cleanup. He looked at my asshole leaking cum and said, “Wow. You should see the size of your asshole, it’s fucking huge.”
Great I thought. I hope it goes back to normal. I heard a click and a bright flash of light and the sound of a polaroid picture being released. A few minutes later he showed me the picture that he’d taken of my gaping hole with his cum leaking out. While it looked sexy, it was also scary seeing my battered and gaping ass. I kept that picture for a few years as a pleasant reminder of that night.
Later that night Tom wanted me to fuck his ass and started sucking me. It didn’t take long and I was ready. I fucked his ass for quite a while until I blew my load up his ass. I still had his cum leaking down my leg as a was fucking him. Me fucking him got him hard again, so I blew him and got another creamy load to swallow. We rested again and ended up blowing each other one more time. Oh to be 18 again. This scene or something similar repeated almost every time we had a sleepover. I went off to college and Tom moved away and I hadn’t seen him again till now.
Here I sat on Tom’s bed. We moved up on the bed and Tom began blowing me. Once I was hard, he got some lube and got on all fours. I got the clue and started fucking him. It didn’t take long, and I was blowing my load. How he kept his ass so tight I’ll never know. We took a break for a couple of minutes, but I knew what he wanted. My ass was going to be sore on the ride home. We were laying there, and Tom asked me to get him hard. I started sucking him and soon he was hard as a rock and standing tall. He told me to lay on my stomach and he’d take care of the rest. He lubed me up and lubed that huge cock. I felt the head pushing at my hole and he told me to push out. I did and he started pushing in slowly. My god he was huge. Nothing like this had been in my ass since I was 18. He kept pushing slowly until I felt his balls resting against mine. Then he started in and out. He was massaging my prostate again and I was rock hard and leaking precum. I could feel it on my stomach which was pressed to the bed. He did that for about five minutes and then he shifted his legs till they were outside of mine and his chest was right on my back pressing me into the mattress. It felt like he was deeper inside of me if that was possible. This also brought his mouth right next to my ear. He started talking.
He asked, “Have you ever had a bigger cock in your ass?”
“No, yours is by far the biggest”
“Are you my anal slut?”
“Yes”
“Can I have this ass whenever I want?”
I’m wondering what that’s all about but answer, “Yes.”
“Does your wife know you like big cock like mine?”
My wife. What the fuck. I haven’t thought about her since I saw his cock, but answer, “No.”
“What would she think about her husband taking a nearly 10-inch cock all the way up his ass?”
I was horrified at the thought but didn’t tell him. Instead, I said, “She’d probably wish it was in her pussy.”
“She likes big cock, does she? She isn’t getting it from you. Where does she get big cock?”
I really didn’t want to get into our whole lifestyle, but his cock felt so good in my ass that I answered, “She meets other guys from time to time with big cocks to fuck her.”
“Are they as big as me?”
“Some are bigger. Some aren’t.”
“Where does she find these big cocks?”
“Dating apps and swinger websites.”
“Does she like it up the ass like you?”
“She does it but prefers them in her pussy.”
“Maybe you two could come out and see me sometime. I don’t get to fuck couples often enough. Wouldn’t you love to watch me fuck my big cock in and out of her pussy? Wouldn’t you love for me to fuck you in he ass while you ate my creampie out of her?”
I groaned and came when he said that. I moaned out, “yes” and then he really started fucking me hard and pretty soon came deep inside me. He laid on top of me for a few minutes and got his breath back and then climbed off me. We both cleaned up and he suggested we go sit in the hot tub and sooth our tired bodies.
We moved out there and grabbed a couple beers. The hot tub felt great. I told him about being a cuckold but told him I wouldn’t change a thing. I was happy that my wife got all the pleasure that she wanted. Sometimes I got to watch, but some guys she met weren’t comfortable with that, so I heard all the details when she got home. Sometimes I ate a creampie and sometimes I didn’t. If she was happy, I was happy. He thought maybe we should get together and see where it leads.