5. Jeff
In truth, I’m not sure what came over me. I guess it was true that a man can’t use both heads at the same time, and I was clearly following the lead of the lower one, because I was about to have sex with a guy. The thought had never appealed to me before, never even crossed my mind, and if someone had told me I’d someday consider it, I would have laughed in their face.
And I’m not some closed-minded bigot or squeamish prude—I simply didn’t find men attractive. I’d seen some gay porn and I hadn’t been repulsed; I’d been bored, feeling nothing if there hadn’t been a chick in the scene. There had been one drunken night in college, after a wrestling victory, when one of my buddies and I had shared a girl. I hadn’t minded him being there or even brushing against him as our hands and legs had become entwined, but we had never intentionally touched or focused on each other. It had all been about teaming up to rail the girl sandwiched between us.
So, bearing all that in mind, I thought I’d have more reservations when the opportunity to have gay sex actually presented itself. I mean, sure, I was getting head from a guy this whole month; but then I could close my eyes and pretend, imagining whatever hot woman I wanted. Anal felt like I was about to cross the line—could I truly claim that I am one hundred percent straight after I do this? And yet, my dick was literally crying for me to stick it in this boy’s ass, labels be damned. A mouth is a mouth; a hole is a hole; sex is sex.
Admittedly, Danny was a pretty boy—not quite effeminate but lean and smooth—and from behind, I could almost pretend he was a girl. Still, it was better not to dwell on that at all. Simply use his body, viewing him as an orifice for my cock—a necessary means to a pleasurable end.
He stripped his shorts and his T-shirt off and positioned himself on his hands and knees, while I rummaged through the drawer of my nightstand in search of lube and condoms. After finding everything I needed, I moved to kneel on the mattress behind him, putting on a rubber and looking at the offered hole that I was about to fuck. Head low on the pillow, ass sticking up, Danny was shameless in his desire for me, chanting all the while: “Yes, Daddy, come on and fuck me, please hurry up and put it inside, I want to feel it, I need it so bad…”
Who could possibly deny such a plea?
Needing no further prompt, I slathered the lube over his clenching hole and my throbbing cock, fingering him for a few moments before the penetration, to prepare him for what’s to come. That’s also something I didn’t think I would enjoy but recently found out I was wrong. The feel of my fingers slipping inside his slick hole, the sight of them going in and out, drove me crazy with need to stick my dick inside.
And when three of my fingers sank into him without a hitch, I did just that: I aimed my cock at his entrance and started to push. I was met with immediate resistance, his asshole clenching in reflex. But as I kept pushing, applying more and more pressure, he relaxed, breathing deeply, and I felt the first breach while my cockhead slipped inside.
God damn . It was like a flaming vice was squeezing my cock, and it felt so fucking good . I thrust my hips instinctively, sinking deeper into him, and he yelped in pain. Yet he put his hand on my thigh, saying, “Don’t stop. Keep going.”
“Are you sure?” I asked, a little worried. “I don’t want to hurt you.”
“You won’t. This is normal. My body needs time to adjust, that’s all.”
After that, I kept pushing, sliding slowly inch by inch, my cock becoming enveloped by a tight silky warmth I’d never felt before, until it was buried inside him balls-deep. And… wow. It was a sensation I almost forgot, yet even better, so much better than what I’d experienced in my youth, because here was a person who enjoyed it, enjoyed accepting my cock, who got off on it as much as I did.
“Oh, God, yes,” Danny murmured in pure ecstasy. “So good… so big inside me… Oh yes… yes… I’m so full… God, I—I can feel it touching my second hole!”
I wanted to ask him what he meant by that, but speaking was difficult at the moment. But as I started to pull out and push back in, I felt the tip of my cock brushing on something deep inside his rectum, a muscle at the end of his colon that needed to open up the same way his asshole did. A second hole!
“Fuck me, Daddy,” Danny moaned, delirious. “Fuck me hard!”
That’s when I started pumping. Picking up the tempo with every thrust, I pounded his ass in a steady, fast, relentless rhythm, the sounds of his moans and my balls slapping his ass growing ever louder. His hole was making obscene wet noises as my cock slid in and out of it. Squeezing and clenching around my meat, that heavenly tunnel milked it as deftly as a hand would. God, that feeling… it was divine. I couldn’t believe what I had been missing my whole life—I didn’t even know sex could feel so raw, so intense. Because, for the first time, I could fuck without holding back, letting myself loose, and allowing my cock to sink as deep as it could, hitting the places in Danny’s body that even he didn’t know were possible to hit.
Slick with sweat, I collapsed on top of him, crushing him beneath my weight. My hips kept thrusting, driving my cock into his tight hot ass hard and fast as a jackhammer.
The orgasm came quicker than I wanted, heart-racing, toe-curling, and I could see the stars exploding behind my closed eyes. Roaring like a wild animal, I fucked him so roughly that the entire bed shook, on the verge of breaking apart, headbord banging against the wall as loudly as the boy that screamed under me.
It took me a few moments to recover and regain what little of my senses had remained. I kept lying on top of him, panting like a dog in the sun. Then the realization of what had happened hit me, and I sprang up, pulling out of him.
The boy lay motionless, save for the small sobs that shook his mauled body. His hole was wrecked, red, swollen, and gaping like a plundered cave.
“Danny?” I called out, throwing the used condom on the floor and pulling him up into my lap. He was boneless in my arms, unable to sit straight without my help, his face wet with tears. “Danny, I’m so, so sorry. I didn’t mean to be so rough. Fucking you felt so good, I… I lost control. Are you in pain? Did I hurt you?”
He shook his head, wiping off his tears. “No,” he said at last. “You didn’t hurt me, Jeff. You made me cum so hard that I cried. I felt the orgasm not only in my dick but through my whole body… The pleasure was overwhelming. This was the best sex that I ever had in my entire life. These are the tears of joy.”
And sure, there was a big wet spot at the center of the bed, where he had spilled his seed without even touching himself. I was glad that he was fine, but I was still a bit concerned. I swept the damp lock of hair from his forehead, took his face in my hands, and peered into his eyes. “Are you certain you’re okay?”
“Yes,” he said, sniveling but smiling at me. “I’m certain. Although I’m not sure I’ll be able to walk—let alone sit—for a few days.”
“Come on,” I said, rising from the bed and pulling him up on his feet. He stumbled and leaned against me, clutching my shoulders for support. I held him safely in my arms, while he giggled like he was a little drunk. He looked almost high, staring at me like I was some goddamned hero, and I couldn’t send him home like that. So I carried him to the bathroom shower and, turning on the warm water, I washed him head to toe, gently yet thoroughly, like he sometimes washed me.