Only twice have I cum while being straddled and ridden: today was the second time. Perhaps gravity has held me back in the past: my load wants to shoot downward out of my shaft. Being straddled isn't my favorite position; while it's convenient for pornographers' angles, I also recognize dedicated bottoms love to skewer themselves when they want to get a big cock really deep in them. Now I do enjoy being stradded by the bottom as part of the experience (provided the guy recognizes that my cock isn't a pogo stick and impales himself with some sensitivity to how I am feeling.) But today was pretty damned sensational and I gave it up while he milked it out...actually, I came because we were fucking each other, fucking together, each trying to maximize the other guy's pleasure. It was great sex, the way it's supposed to be, in other words.
Interestingly, the guy in question is a total bottom. Frankly he doesn't seem to be passionate about whether he cums, but during our encounters I have insisted that he get off as well. Besides the fact that getting the other guy off is part of the fun, this guy has an amazing dick and huge hairy balls, and shoots copious amounts of spooge so it's a sensory sensation for me too. But he makes it clear he sees his role as that of a total bottom, and that his "hole" is for my enjoyment. Now, I know he enjoys getting fucked: he's not a screamer, but he's really responsive. And, what has made me smile has been that each time we've been at it for a long time, he'll tell me how much he loves my cock and that I make him soooo glad he's gay. However, from the get go his priority is whether I am enjoying myself, whether I feel good, and you can tell that his greatest pleasure is from seeing me cum -- so today looking down me me as he felt me stiffen and spasm he had the smile of a kid with an ice cream cone. I first experienced that smile during our initial encounter when going for seconds I had him on his back and he broke into a grin when he watched my face contort as I spurted a second load into him (interestingly, when I have cum twice in one session it is typically with the guy on his back as the friction is different, massaging my cock differently. I'd suggest that it involves different parts of my cock, but I imagine that's impossible when you've already been thrusting your bare cock into a bare ass for 40 minutes...All if it has had some stimulation.)
The fellow in question is endearingly geeky. Good looking, slender, tiny ass, flat stomach, tiny ass, and nice furry legs and a nice patch of hair in the center of his chest (and as I mentioned, a lovely cock, not as long as mine but a great size: thick and with heft -- it's just a pleasure to hold and stroke and suck, and he has lovely balls that feel great in your hand and you can tell that he likes having me lightly stroke them with my fingertips.) Anyway, the geeky part is he's in his early 40s but quite in touch with his inner child with adventure movie posters, Disney figurines, and science fiction stuff festooning his apartment. He defines himself as a geek, but clearly is a very piggy geek who is definite man who loves mansex. It's all endearing: when I arrive it's all about the sex part, but then in between orgasms he wants to cuddle and is sweet and very considerate. It's quite the ying/yang sort of thing. But, we are very much opposites: me a day person, him nearly entirely nocturnal; me a guy of conservative tastes, him into popular culture; me black coffee, him coca cola; me a total top, him a total bottom.
So far we've gotten together three times (does that mean we're done? I have a feeling we'll actually continue to connect unless he falls in love and decides to be monogamous) and the first two occasions after entering him I held back from cumming early as it was clear how much ecstasy he was experiencing getting plowed. He's also into feeling the pain/pleasure of it (not in a weird way, but likes to have his nipples squeezed hard and lightly bitten as well as to take a sustained drilling and it to be regularly punctuated with sudden long, deep thrusts. Actually those thing don't bring me pleasure as my preference is to have the guy flat and to suck the back of his neck and steadily grind him into the mattress till I cum -- if I am just thinking about me.) Anyway, as I have mentioned in earlier entries if I am fucking a guy and my initial urge to cum passes then it means I'll need be at it for at least 20 more minutes, dismounting for cool down sessions before the lava will rise again.
During our first encounter before I came I could tell he was close to cumming and asked if he could still take it after shooting his load. He said yes, he came, and then I licked it from his torso, snowballed with him, and then spit it on his hole and used it as lube. But after I'd given up two loads he later admitted he was sore from taking it after he came (cripes, this was nearly two hours later; I felt like a heel and since then I haven't let him cum till I am definitely done.) However, he's so agreeable and wants so much to be submissive and please ("my hole is for your pleasure...") that he insisted it was fine and that he enjoyed the rawness of the feeling.
Today I was definitely enjoying it but Mr. Happy wasn't about to let go of his juice. It all began with him giving me an amazing blow job and then he straddled me and attempted to take it mostly dry (it didn't work, and frankly I'd didn't want to have the epidermis rubbed off my bone, so after initially entering him after rimming him, and a combination of his and my spit I insisted on some lube. Anyway, it was a marathon session with me pinning him to the mattress, getting him on his side with his thigh pulled up, and then our coupled cuddling: sweet as you can kiss, but not good for maximum penetration. But neither of us was in an apparent hurry (though I was thinking it might be one of those days where I can only finally cum by later stroking off, which is really frustrating.)
We've gotten to a point where he appreciates I want him to maximize his pleasure as well, and I soon found him straddling me. Often with sex you want it to be spontaneous and for the other guy to intuit how to position himself, but today I directed him to lift up a bit and then we both were really enjoying it simultaneously: rather than his weight pinning me and him impaling himself the position allowed him to thrust down and for me to thrust back. It was great. But each time as I thought I was about to shoot Mr. Happy clammed up (pardon the metaphor.) So he dismounted and we cuddled and made out, stroking our cocks together and simply enjoying each others' naked bodies. Then he got on top again (I could tell he was surprising himself.) And then we got into some serious fucking with us staring with intent into each others's eyes. And then I finally let go and with determination he thrust down and squeezed with all his concentration. Eventually my cock eased out of him and he leaned over to suck it. As we laid side by side more cum gradually dripped out of my cock, and studying it he swooped down each time to lap it up. He observed: "my hole is really going to hurt tomorrow."
I told him that it was only the second time I'd ever cum while being straddled and a look of pride and accomplishment swept across his face. He said he didn't want to get a big head about being a good bottom as it was all about the top, but you could tell he was enjoying recognizing his power (geez: did I turn this guy into a power bottom?) He mentioned that he could tell that he was fully enjoying it while we were fucking as his cock was partially flaccid, meaning that his concentration was entirely on using his ass. But eventually in my afterglow I said "I don't know if I can fuck you any more, but let me know how we can get you off." Clearly he felt a challenge and swooped down on my cock and applied every possible trick with his mouth, tongue, and lips till I was painfully (painfully as from the earlier marathon fucking I'd given him with it) hard. Then he straddled it and began to stroke his cock, insisting "keep fucking me after I cum; I want to keep taking it as long as you want it." Well, at that point I just wanted to get him off; I was fucked out and fortunately soon a stream of his warm cum was pooling on my chest and he was shyly grinning. Then I delicately pushed him up and slipped out from under him. My cock was almost audible in it's relief.
It was great, but I knew I needed a hiatus. If it had been a sleep over I'd be probably fucking him again right now. But sometimes your eyes are bigger than your stomach (another regrettable mixed metaphor: mea culpa.) After a decent interval (I never jump up to leave a guy) I protested we should do something vertical with the rest of our days and he reluctantly let me dress.
My cock tender sensitive right now, I can only imagine how he's feeling. My parting advice was him to avoid Mexican food tonight (sorry, I just couldn't resist; it got a good laugh out of him.)