Chapter 25: Randy Visits Me On His Knees
Woke up and checked to make sure I hadn’t dragged anchor. Nope. Satisfied, I went below & put on coffee. As it was brewing, I released my little friend and gave him a full body massage. Stroked him till he squirted. Poured some coffee and climbed into the cockpit to enjoy the sights.
As I was reviewing the events of last night, I heard a dinghy approaching. As it pulls up and slows, I see it’s Randy from the office who was at Carla’s last night. “Permission to come aboard, Captain?” “Certainly.” We got his dink tied off and he climbed into the cockpit.
“What’s up, Randy? Can I get you a coffee?” “Sure. Thanks.” Oddly, he followed me down below as I poured his coffee. “So, what brings you out here Randy? Did I break the rules or something?” “Oh, no. Nothing like that. It’s just that I was thinking about what you said at the end last night. How you felt short changed and everything. I got to feeling bad about it so I thought I’d come and make amends.”
“What do you mean by that Randy?” “Well, I thought I’d let you fuck my ass. Or you could fuck my mouth maybe. I don’t know. Anything to make you feel better.” “That’s awfully nice and thoughtful of you. I must tell you though, that not 15 minutes ago, I jacked off. Might not have much left.”
“Oh, that’s okay Sailor. I’m okay with you pounding my ass for as long as it takes. I’ve got nothing to do and I love having my ass reamed to the max. There’s a place I go where I get 6 or 8 guys to line up and fuck my ass, one after another. Fills me with cum, it drains out and runs down my balls. And other times I let them fuck my mouth, same way, hard and deep, one after another. Or I can come back later if you’d like. Your choice.”
I pondered the situation as I sipped my coffee. He had offered either an ass fuck or a blowjob. And either now or later. After having just shot my morning wad, I couldn’t see an extended ass fuck. But maybe I could do his mouth now and his ass later. “Well, Randy, that’s a mighty kind and generous offer. Even though I’ve just cum, I think I’d like to fuck your mouth for a bit.”
I told him to get comfy on his knees as I dropped my boxers. My little fella was all shriveled up, having already done his duty. Randy pulled on it with his fingers and extended it enough to get his lips on it. Using his fingers, tongue, and lips he started licking and kissing it, getting it wet.
He kept this up for several minutes before my cock started to respond. Soon it was hard enough for Randy to work with. He had a talented tongue which he would swirl around the head, always touching my sensitive spot on the bottom. He’d rub his tongue up and down across my clit. All the while he was bobbing his head in and out, getting more dick inside each time. By now my dick was fully hard, ready to play.
Randy reached around and grabbed my ass cheeks, using his grasp on them to pull my pelvis toward him. He was now fully engaged, fucking my whole shaft with his mouth. I decided it was my turn so I grabbed both sides of his head and started fucking his mouth. I started him off gently but soon turned up the heat. I wanted to test his gag reflex. I pushed my cock in hard and deep, expecting the usual deepthroat door at the back of his mouth. Much to my surprise my cock slid right passed it as if it wasn’t there.
Overjoyed, I started ramming my cock from the tip to my nuts into his mouth. His mouth was slobbery and wet and I was going all the way in, but it just didn’t feel as tight as a girls blowjob. Maybe he had a bigger mouth or something.
But tight or loose, I was watching as my dick continued to pound his throat relentlessly, the whole shaft disappearing and reappearing from his mouth. I kept this up for what seemed like an eternity to where he was drooling and slobbering a river, spit streaming from his mouth. I just continued this leisurely mouth fuck, in and out, over and over for a good 15 or 20 minutes. No stopping.
After a few more minutes of watching my cock disappear, then reappear from his mouth, I felt a little tingle indicating that I was going to cum. I quickened the pace, shortened the stroke, and started pounding it deeper and harder. I was slamming my dick hard into his face now and, in a few more strokes, my whole cockset, dick and balls, were tingling.
So, I smashed my cock into his face, deep down his throat, held his head to me and let go a very small load. Only two spasms. I just held my cock down his throat for what seemed like ages. When I finally pulled it out, he gasped for air as a river of spit, drool and creamy cum juice drained from his mouth.
“Wow, Sailor. You were hard to get going but once underway you did as good a job as any of the other guys who do that. Except they usually have much bigger loads.” “Yeah, sorry about the slow uptake but I told you I had just cum.” “No worries, Sailor. No worries. Maybe later you’ll have more cum juice and you can try again.” “Great! Watch out ‘cause I might take you up on that.” “I’m hoping you do, Sailor.”
Having spent myself twice before noon proved exhausting. I settled in for a short nap.
