His First Anal

He's writhing under me, gasping that he doesn't know what sounds he's making because he's never been this loud before. Incredibly coherent, he asserts that he's not a screamer. Hah. In the push of a button and five short strokes, I have him bothering the neighbors quite effectively. I push the button again, turning off the bullet embedded in the balls of my red feeldoe, and let him regroup. I assume I'm nestled up quite snuggly against his prostate, giving it solid contact for the first time.

I couldn't reach it earlier with my fingers— not one, not four, not five. Did he tell me he was an anal virgin when I was coating that fourth finger with lube, or as I rolled the studded condom over my bright red detachable penis? It must have been the latter, otherwise I would have let the texture be a surprise. Judging from his yelp-gasp-alarmed-moan sequence after my head popped in for the first time, I'd say it still caught him thoroughly off-guard. I cuddled him while he processed that initial feeling, my impossibly hard cock sliding awkwardly across his scrotum and confused penis, ever-ready to return to its proper place. When I had started teasing his ass with just one or two fingers, he'd been almost as hard as me. Even as he put on a worn out pair of my black seamed stay-ups, he was mountable. But as I entered him with my (literal) tool, and throughout our little pegging session, he was like a worm on a hook—and I the hungry Muskie.

Although I had no feeling in my shaft, I could tell his ass didn't quite "swallow" me the way mine had swallowed his fingers last night. On the one hand, that would create an intense feeling as it pulled the bulb inside me against my g-spot. On the other hand, less clenching means less risk of pain. As I millimetered purposefully inside, I found my excitement tempered, wondering when he was going to yelp and clamp down on my numb, uncaring hunk of silicone. Amazingly, after asking only twice and staring intently at his facial contortions, I slid balls deep in my friend's virgin ass. He asked me to pull out slightly, and I internally celebrated at the incredible strength of communication we had developed over the years. After all, we could never have started playing with each other's butts without it.

Once he worked his way on top of me and I reclined against the couch, we encountered a problem : the easel mirror just wasn't in the right spot, but neither of us wanted him to get off my dick. Ten minutes later the mutual desire to watch my cock penetrating his ass hole finally motivated him to gently slip off, stagger over to the mirror, and position it according to my direction. Satisfied, my friend returned to lower himself on to my cock as our lustful eyes bored in to the mirrored point of entry.

Finally, though, I got sick of the metal rings of my harness digging in to my hips. I could tell he was ready for me to plow, so I suggested we move to the bed—and bring the mirror with us, naturally. Having 30 pounds of muscle on him, it was easy to drag him to the end of the bed and throw his stockinged legs up on my shoulders. My hands each cupped a tiny cheek, and I smiled, enjoying being able to step so deeply into male shoes. If only the sensitivity of my breasts could transfer to my penis for this session! I tossed my head nostalgically for a feeling I'd never had, and then watched in the headboard mirror as my arms bulged with the effort of lifting that little ass up while I stroked. I glanced in the easel mirror, enjoying the juxtaposition of the hard leather and soft stocking, the black stocking and red feeldoe...

Feeling proud of myself for learning to judge the length of my strokes better and not accidentally pop out, I set his ass on the bed, caressing his legs and body, practically purring. I eased in as we rested, finally employing the vibrator. I can't remember the last time I saw a man that bug-eyed. He looked like I'd just short-circuited his entire lymbic system. Finally, he understands why I don't -- can't -- talk during sex. After all these years, I get to watch someone undergo a sexual exorcism, instead of being the subject. In that moment, he surely forgave me for all those half-hour g-spot massages where his fingers had cramped up or gone numb.

As his arms flailed desperately across his chest and back out in crucifixion pose, hands twisting the comforter, I synchronized my kegels and my finger on that little magic button. Bzzt! Bzzt! ... Bzzt! Sometimes I had rhythm; sometimes I syncopated just to prolong the novelty. After a few solid minutes of anguished bliss, his hands clamped down on my forgotten breasts. Looking me in the eye with a mixture of anger, desperation, and ecstasy, he told me to stop fucking teasing him and fuck him.

Unable to keep my smug smile from blossoming, in a surprisingly saccharine voice I replied, "No."

His frustrated roar and the thump of his back against the mattress set me off, though. We both identify and respect each other as dominants, but at this moment, I couldn't fight the rush of power exchange flowing through me, real or projected. I dug my thumbs into his hips, my fingers into his cheeks, and unleashed the other half of me -- the half that rarely finds satisfaction because of my mild vaginismus. At this moment, it was though my cervix didn't exist, and I could fuck with the animal abandon I always collared within myself to avoid yet another incredibly painful experience.

Neither of us orgasmed, but the summed intensity of our feelings surely equaled those few moments of climax. Drawing out the pleasure over almost four hours was surely the better, harder end of the stick. Nonetheless, we both sensed our bodies' reserves emptying. Although my impossibly hard cock could keep going forever, I let him guide me out, using our little hand signals. Before I withdrew, I gave his prostate a few good nuzzles, using my kegels to wiggle the head again. His unabashed gasps and writhing assured me he now truly understood the power and meaning of "tiny little gentle movements."

We entered the bathroom to shower, and began to feel how sore we were. As I bent over to turn on the water, I quipped that both my holes were sore from earlier, and that he should kiss them and make them better. So naturally he obliged. And to think that the night before I had still almost been too grossed out to ask him to lick my ass... my how far we've come.