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Best Two Times?

I'm older now and have lot's of time to reflect on my best times with another guy. I have to say that it's my two first-times, the absolute first when I was a boy all wide eyed and curious being mentored by an older boy who cared for me as much as I did him. The next first time was with a man when I was barely an adult but wanting to experience the love of another man so badly that the beautiful experience between us has never been better.

I'm wondering if Tops, Bottoms and guys who prefer oral would be willing to share their two bests with us?

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# 81556 - by OldNsissy / August 18, 2025
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Anonymous

by Anonymous on Aug 18, 2025 at 9:37 AM

My best m2m was probably around 30 years ago when I was at an adult theater known for it.
I usually topped but this night I was exploring giving head for the first time and found out I liked being between this young guy's legs kissing, licking, sucking and even rimming him.
That might have been the first time he felt a tongue up his ass because he went crazy and began cumming all over the wall and the floor and begged me to keep my tongue up his ass.
For my part, I wished my tongue were longer so I could get it in deeper. I was being a nasty pig and eating this stranger's asshole out. So fucking filthy and nasty and taboo and it made me throb and spurt my own load a few minutes later.
The reason I think it might have been a best time is that even after all these years I still think about that night and how hot and sexy it was.

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Anonymous

by Anonymous on Aug 19, 2025 at 6:01 AM

My first will always be remembered. We were 12 it was in the summer and my cousin and I were down by the creek just hanging out in the woods like everyday.
We started talking about how we got hard and both of us liked to play with ourselves and it felt so good to get off that not long into the conversation my cousin said we should get naked and do it together. I was as ready to do most anything and once we were both naked our dicks were hard as a rock and we started jacking off watching each other. My cousin had a bigger dick than me and I wanted to touch it so I reached for it and as I jacked him off he slowly pushed down on my shoulders until I was on my knees in front of him and his dick was inches from my mouth.
He asked if I wanted to lick it and he slowly eased forward until the head was touching my lips and once I licked on it I put it in my mouth and he began to moan and move his hips like he was fucking my mouth. Then he began to tell me how good it felt and that just made me want to suck it even more. I had one hand on his naked ass one hand around my dick jacking myself off and gagging on his dick as I sucked it seemed to get bigger.
Then without any warning at all he grabbed my head pulled me towards him then he pushed his hips forward and let out a really loud moan and as I gagged on his dick he shot his cum right into my throat and kept grinding his hips into me moaning and I shit my load on the ground between his feet.
He kept fucking my mouth and I didn’t want to stop sucking his dick and I even licked his nuts and had them in my mouth several times. He started getting hard again and told me he wanted to try something else then I stood up. Next thing he did was turn me around with my back to him and I felt his dick on my ass and he said he wanted to see if he could stick his dick in my ass.
At first I told him no and asked him to stop but he kept jumping on me and had me leaning forward bent over and I had both hands around a tree limb as he began to rub his dick on my asshole. It felt good so I didn’t resist him and next thing I feel is my asshole stinging and begging to open up then the head of his dick wanting me and it hurt. He told me to stay still and just relax. Before long he was all the way up in my ass and was now fucking me ip the ass moaning as I joined him both of us marking very loud and making all sorts of noises. He fucked me for a good long while then rammed his dick up my ass really hard and shot his cum up my ass and with his dick way up inside if me I pulled on my dick shooting my load out in the ground.
He left his dick in my ass for a long time as we talked and finally it slipped out and I asked if he could put it back in. He couldn’t right then but in less than an hour I was face down in the grass asking him to do it again. That first day he fucked me 4 times and it was me asking him to do it. For years I took his dick up my ass and he came inside of me 100’s of times and still to this day when I see him I think about how he used to fuck me up the ass and several years ago I asked him if he would like to do it again but he said no. I asked him several times that day but he never did it to me.

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Anonymous

by Anonymous on Aug 19, 2025 at 6:28 AM

Above post: Like wow your story reminds me of me and my best friend Tommy back in 6th through 8th grades in middle school. I was a totally smooth and he'd hit puberty already and was proud of it. We'd skinny dip at his uncle's farm just out of town and pretty much were handling then suckn each other's dicks. We both were in football and showered together at each other's house depending on which of our mom's picked es up, we were pretty much inseparable. We were starting 8th grade early football practice in July 8 to 10:am to beat the heat. Mom picked us up and dropped us off so we hit the shower together and goofing around and Tommy had his hand around my waist pulling me towards mom and dad's bed saying "today's the day" meaning he was gonna fuck me. We were giggling and he literally got a rock hard on and we used mom and dad's warming gel lube for my first fuckn. We did it twice that morning before mom got back from grandma's and grandpa's. I was so calm mom noticed that I wasn't all ADHD as usual. That wonderful feeling of Tommy cumming in me was over the top for both of us and we get together for what we call a rewind even though we're both married and in our mid twenties.

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Anonymous

by Anonymous on Aug 20, 2025 at 1:43 PM

Between marriages I decided to try sex with men. I was only interested in oral and had mutual BJ's with a few guys.
Online guy asked if I would be interested in a 3 way, him and his buddy, both cut, and hung. One had the thickest dick I've ever seen.
They had a playroom with toys and a swing. It was my best time because I went past just sucking dick. They had me strapped into the sling, one guy fucking my mouth and the other my ass. It hurt a first but felt amazing after I relaxed. They pounded my until I had cum in both ends.

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