Breaking in a Virgin

Tonight I connected with a businessman visiting out of town from Texas.  Miracle of all miracles, we connected through Craig's List (a posting that didn't get flagged by a declined suitor...)  This fellow posted me several times throughout the day and just before I was supposed to meet him he indicated co-workers were staying on the same property and he wasn't going to be available.  I figured that it went with the territory through CL connections and decided to do something "productive".  But then I got a message right afterwards saying that he'd ditched the co-workers and to come to his hotel, fortunately a hop, skip, and jump from my house.

I arrived and asked him if it was going to work for him.  Nice enough fellow:  a firm but noteworthy belly (good), nice sized dick (better), and hairy (hot.)  I asked him if he kissed and he indicated "not really" and then gave me a cursory peck on the lips; this was immediately after he said he was normally a quick cummer so that he'd had a few beers to slow himself down.  At this point I was imagining a max of 30 minutes.

While I started to suck him to get him to relax (but, had to keep pulling off so that he wouldn't cum), he was seriously into sucking my cock and was excellent.  He had it all the way down his throat much of the time.  Since I couldn't work his cock (remembering that when the bottom cums the show is over) I suggested he get on his hands and knees and plant his ass over my face.  The minute my tongue went there the guy was hooked.  He was very considerate and kept sucking my cock but he clearly just wanted to savor having his ass eaten.

He told me he wanted to get fucked but hadn't had a cock up his ass before; swell, I thought.  Mine is not the cock for a virgin; having had guys whine it was too big I figured this was going to end the minute I tried to get it in.  I continued eating his ass and then started some teasing of his crack and hole with the head of my cock.  The man was reduced to jelly:  he was pushing back against my cock and it was going partially in; I pulled off several times to rim him some more, and he was loving it.  The next thing I know is that the man who doesn't kiss was rolling on top of me to passionately French kiss.  He sucked my tongue and plunged his into my mouth.  I just layed there and enjoyed the passion.

He suggested a condom, but I wanted to keep the action going.  I got some lube and started to finger fuck him.  He rolled on his side and throated my cock while I loosened him with my fingers.  On his side he was pulling me down to kiss him and I could smell the manmusk he was working up; I pushed his arm back and beared my face in his pit between making out with him.

Next he was on his stomach with me teasing him again:  this man loved feeling the heat of my cock against his hole and was pushing back against it.  I made it clear I wasn't pushing into him, but soon after I felt my cock three quarters of the way inside him and him gasping how great it felt.  Soon he was pulling off and wanting a condom, which was totally cool

I rolled the condom on and fucked him lying on his stomach; he was panting "fuck me, FUCK me!" It was nice but he wanted to be on his back.  I was trying to take it easy and to be as gentle as possible, but this guy wanted pistoning.  On his back he kept pulling me forward to passionately French when not demanding I fuck him.  Up till this point I'd managed to keep him from stroking, but as I massaged his prostrate he was fighting to stroke his cock.  I released his hands and he furiously stroked while I moved in and out of him.  While I kept waiting for him to say it hurt, instead he kept groaning how great it felt.  The next thing I felt something warm hit my face; the next shot went over his head (no b.s.) and he spurted healthy ribbons that caked the hair on his chest.  I eased out and told  him to enjoy the afterglow (he was worried about me getting off.)

As it was I never did cum, but I had a damned good time.  While spent he threw his leg over my thigh and stroked me while making casual conversation.  He was enjoying the man2man touch and while done wasn't in a hurry to pull on shorts and usher me out.  He kept telling me how great it was, which pleased and surprised me as I was worried about hurting him and killing his interest in anal.  Apparently not:  I think I converted him to a bottom for sure.  And I found, again, that I don't need to cum to have an "orgasmic experience."