Yeah, I'm the son in this story.
When on a work trip, I placed an ad that got a number of responses. Anymore, with craigslist you have to be vague as can be, or you're flagged and removed.
One response I got back was: married 50 y.o. masc, s&p/brn, 6' 0", 190, in-shape, CLEAN, ddf, non-smoker, professional, into most things sane/sane, body contact, nip play, JO oral.
He could only do early morning and since work didn't start for me until 10a, I could "work" in my hotel until about 9a. He called at 6:30 to say he was in the hotel parking lot. I gave him the room number and opened my door and went back to bed.
This did not start off or was set-up as a dad/son thing. Really the thought was me giving him a blow job and then sending him on his way.
But there I lay - with barely a sheet covering my parts when he walked in, fairly handsome and in good shape. Stripping out in the outer room, he entered exposed....then up to the side of the bed, where his cock went to my mouth and my mouth to his cock.
It grew in me. A good 7", average girth.
My head went over the bed and he fed me that way, but then he did something. He touched my chest.....a big turn on. Then he touched my dick, which is ok, but his hand slipped beneath my nuts and his finger just grazing my asshole.
I squirmed. It was involuntary. He noticed.
He told me to get on all fours at the edge of the bed. I did. Like a good boy.
No words on what he was going to do, but we both knew. Of course he did. I more than suspected. And soon after, he made contact - pushing the head of his dick into me. He met the appropriate amount of resistance, but make no mistake - it went in.
Hey somewhat hissed "whatta good boy".
After that he slid right into 'dad' mode. He seemed into it and I followed suit. If that's what was going to turn him on and get him off, I can role play with the best of them.
He went on about how hot it was to sneak into his son's room when no one knew. How he liked taking advantage of his boy while mom was right down the hall. He pumped harder.
I asked him not to tell anyone - least of all my friends. He assured me it would be our little secret - as long as he could continue to come back whenever he wanted. I told him he could.
All of this got him off much sooner than I would have liked - not that I need or want the role play, but I did like the fuck and he was good at it. I think the scene he established for himself got him super excited.
He shot a nice load into me and started to clean up and get ready to go. But then he kept playing with me and got erect again. He had me bent over, but all he did was a few strokes in me before he couldn't keep up. We both knew it and it was ok.
He had to go. I would have to get ready for work. We both got what we wanted. He seemingly got something a little extra: a son, for 30 minutes.