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I tried, I really did

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I've never been too fond of sticking my dick up anybody's asshole. Even my wife, in our younger days whom I swear seemed like she had another clit somewhere up her rectum.
Fucking women up the ass didn't appeal to me so the idea of fucking another man up the ass was totally out of the question, - until ...

I was extremely horned up one day which lowered my inhibitions to certain things and I responded to a CraigsList ad by a (married) guy who just wanted to be fucked. (pickin's were slim that day)
In a few emails I'd told him I'd be happy to jack or suck him off but that I wasn't really into fucking. He said no, that he really wanted to be fucked and went on to describe in detail how it made him feel to have a stiff dick slide up his ass. His description got me so horny that I convinced myself that maybe it was worth a try so I told him that I'd try but wouldn't make any promises for the outcome. Apparently, "pickin's were pretty slim" for him as well because he readily agreed.

Arriving at his home about 30 minutes away:
After some introductory small talk we headed for the bedroom and got naked.
We fondled each other's dicks for a few minutes and he asked me how I wanted to do it. I told him whatever way he liked best.
He grabbed a condom and some lube from the night stand and rolled onto his back.
As I "rubbered up" and greased my dick (I was hard as a steel pipe) he took the lube, put some in his hand, raised his legs and lubed his asshole.
It didn't LOOK like he'd shaved it but his asshole was smooth which made it more inviting.
[Text: Removed]

So, he's on his back with his legs in the air and poised with my dick aimed at his asshole -
I used one hand to work it in (and yes, it was tight - and yes, it felt good) and grabbed his dick with my other hand.
He was moaning and squirming and carrying on and once my dick was all the way in I remained still for a few seconds while I stroked his dick.
As I started to move my dick in/out in unison with jacking his dick - I took about six strokes and my dick went flat. I mean like a blown-out tire.
I stopped with my limp dick still in his ass hoping it would come back to life but it was dead.
I stayed there, with my pitiful, limp dick still lodged in his ass hole and just continued to stroke him.
It was apparently enough for him because just a few more strokes and he let loose with a fountain of cum unlike many I've ever seen.
He moaned and growled and bucked (my limp, rubbered dick fell out of his ass) as his cum rained down and splattered on his chest and stomach and my hand, with his dick still in it ...

And just like that, it was over.
He got up, went to the bathroom and commenced cleaning himself off without offering to suck, jack or otherwise try to finish me off -
I sat there, on the bed for a few seconds with a condom-covered, limp dick wondering if I even could get a nut - NOW ....
I got dressed, we bid each other ado and I left.

Oh well, I tried. I really did.
No more trying to fuck a man in the ass for me.
 
No I hear ya man. I was married faithful to one woman for 20 years but was always Bi - first gay hookup I did my wang just wasn't having it - dude even gave me two Viagra and it didn't do shit - my cheeks for flushed, I could feel it working - I was relaxed and ready to go but my dick just didn't want it. I finally just started getting my boots back on and dude said "you're leaving?" And I said yup and walked out. Later I texted and sorta made him feel better - but I just went to a few other hookups and found what I liked and all worked perfectly hahaha -.jist gotta know what you like and want.
 
Right there with you, SteamStroker. I'm more than happy to trade BJs, but I've only ever completed topping someone once and it was a race to see if I could pop my cork before deflating. Anal isn't for everyone.
 
Well, at least you can honestly say that you tried. Fucking is actually not for everyone, and there's a faction out there who just prefers BJs.
"We are who we are"...
 
Such a shame, still it could happen yet.
 
Thank you, SteamStroker! Just made my day. This helps me move on from the epic fail I had. Two condoms with some really poor oral in between. Just was not going to happen.

I suspect some of it has to do with how desperately the other guy wants it. That's my theory, anyhow.
 
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