Restless I logged into Craig's List on Saturday and responded to an ad and actually got a response. The guy responded with alacrity in fact! He was flying into SFO from the East Coast (must have had a layover somewhere to go back and forth in email) and was staying at a local Marriott and interested in some hot oral action. While I wanted more than oral this was convenient to a number of errands and he was anxious to connect.
Earlier in the day I'd been on Grindr, which in my short experience with it sucks (and apparently alot of other disgrunted subscribers from the comments posted.) A bunch of sanctimonious guys giving other guys major attitude for not initially posting face pics on their profiles (so what if they are discreet? If they eventually send you a pic what harm is done?) , and a bunch of flakes. It really reminds me of the current version of gay.com (which used to be fun and then became lousy; it seems to have been bent on it's own extinction by eliminating chat rooms and not allowing guys to post explicit profile pics/I mean let's face it/guys are not logging in there looking for bible study. Pretty prim and restrictive like it's not a hook up site/well I guess that they have functionally prevented it from being one now.) I found out that my subscription is temporary and due to expire/I'll be glad to delete it from my phone. But, enough ranting...
So the CL guy wrote and gave me his room number when he checked in and said the door would be open and that the room would be dark and he'd be naked and jacking and that I should come in, strip, and feed him my cock. I arrived at his room and pushed open the door and couldn't see a thing/it was ridiculous. I spoke into the dark and said "pal I can't see anything, can I at least put on the bathroom light?" He responded with a laugh and said sure, and I groped around awkwardly trying to find a light switch.
When I succeeded he was lying with his head hanging off the edge of the bed/definite cub. About 5' 8", broad shoulders and fleshy on top of some muscle/now in his 30s he probably played some sports a long time ago in high school. He was grinning and stroking and I fed him my cock, which he sucked with gusto. I leaned over and started to suck his/about 5" long/3 1/2" thick: pleasant if not "wow" material.
I got on the bed and we got into some mutual sucking and then I rolled him onto his stomach and started to eat his ass, getting him really cranked. After awhile he rolled onto his back and had his legs up in the air and we got into some hot frottage and he wanted to kiss. It was interesting how this was progressing because he'd made it clear in his ad and our initial email that this was to be just him sucking me off. I had to keep swatting his hand away so he wouldn't cum first. I was teasing his ass with my cock, and then got him back on his stomach and was rimming him and started to rub my cock up and down his crack which he was loving. However, whenever it got close to his hole he'd warn me it was too close and that it made him nervous. He told me he didn't want to get fucked.
What we were doing was more than satisfying and I was enjoying it for what it was. His ass was incredibly wet from my rimming it and he had the a/c off and it was warm and we were really sweating. I put my cock between his legs and was thrusting between them. I remarked "you must be an incredible bottom" and he advised me he'd never been fucked.
Well he was sure liking my rubbing my cock up and down his crack and was panting with lust. He told me he wanted me to stroke off on his back. Then suddenly he manuvered and had my cock lined up against his hole. At first I wasn't sure that this was happening but I felt him thrusting his ass back. I didn't initially imagine it was in at first, but he kept thrusting back and squeezing it and I realized he had about 3 inches in him. It felt really good and I realized that he wanted to pretend what was happening wasn't happening, so I didn't say anything and let him control the action. However, after all the frottage I was really stimulated and knew I'd blow. Since I was enjoying it I was striving to hold off but realized I was getting to the point of no return so pulled back (surely out, actually) and then spurted on his back. He reached back to feel it, almost as if to check that it was there and not in his hole.
Immediately he rolled onto his back and vigorously stroked off, shooting stream across his broad hairy belly and then started to giggle. Then he said "well friend, thanks." Wow, talk about abrupt. He said "I'll get a towel for you" and dashed to the bathroom and dampened a washcloth and handed it to me. Okay...suddenly he was very self confident
Fortunately it was a tee shirt/sandals/shorts day so I was soon dressed and thanked him and headed out the door. It was fine, but could have concluded with a little more grace. I think the term is socially awkward. Whatever, it did the trick (pardon the pun.)