I'm all about older men too as I see some others are posting as well. I'm only 22 and I haven't been with anyone remotely close to my age. 50 and up is what I like. Their experience and appreciation is my aphrodisiac.

My first time was not at all planned. I was with my silver haired partner and He was always good for just one pop and it was usually after I would give him a nice slow but firm hand job. He would usually suck me to completion and I would finish him off after that.

This one particular night we were watching a gay gang bang where this one guy who had a similar physical likeness to me was taking cock anally from 5 others. We were both impressed but what really got me was that one guy pulled out and sprayed hard all over this guys face and after he came within 30 seconds he came again. He just kept jacking off until he squirted again. It never occurred to me that that could be done.

We talked about it in wonderment and decided you had to be really REALLY horny to do that. He asked me what he could do to me to try and cum twice like that. I told him that maybe if he fucked me while I was on my back hips lifted up that maybe I would be able to but I wasn't even sure I could take his cock anally.

After a good 10 minutes of positioning and some pain he got himself in and he was thrusting pretty well and my cock was super hard and bouncing around with his thrusts. I forgot all about our plan and was really enjoying his body on top of mine and soon he was releasing cum in my ass. Right after he started jacking me off and before I knew it cum was erupting out of my cock and before I relaxed he was jacking me again to try to get me off right away for the second time. Initially I didn't think it would happen but then I reached for my asshole, inserted a finger in and as I felt his um from my ass thst was all I needed and I came again. To firsts in one night.....not too shabby.
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I was young (not that young - 18 & working a summer job), and I know now that this older guy was working me, but I didn't know it then.
I worked for him on a fishing boat. We started going back to this tiny place he kept right by the pier. He worked me slowly, first weed & beer, then straight porn, then he started blowing me. After a couple times with that, he got me to blow him of course. He than started working to my ass. He was on the couch, I would lean over and take his dick in my mouth. I remember him licking his fingers and finding my hole. "Sweet ass" I remember him saying. one day he just pulled my head up and turned me around on the couch. He pulled my jean shorts and briefs right off. He used lubed me up with crisco (remember crisco anyone?) I remember he leaned over and told me to bite the pillow if it hurt.
God damn did I bite that pillow. He pushed in slow, but steady, and started to pump. "Yeh bitch, take my cock" he said, stuff like that. It hurt, but damn it felt good. I remeber feeling his sweaty, hairy body on my back. Dropped a load right in my ass. Then, as he was getting soft, he reached down and gave my balls a squeeze. "Tell me you're my bitch" he said.
"Yes" I said. He didn't let go. "Say it."
"I'm your bitch"
"Good boy"
So my first ass fuck was from a real rough daddy, who worked me good and got what he wanted........and yeah, it was good for me too.

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Crisco? Sure would have been slippery but did it last?

On thing I find interesting - back then the guys just went for it. Not really planned or preped - just fucking.

I guess that is a good thing - if my buddy had told me the first time I needed to have an enema first I would have been "No Fucking Way!" and probably never would have tried it.

I am not into scat or anything like that - that is not where this is leading - but I find it interesting that in newer stories of guys first fuck there is lots of talk of prep - but in those of us that did it in the past it was just the fuck that mattered.

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The best lube ever invented. Crisco.

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