“Yeah, you little slut,” he said, almost growling. “Swallow that cock like a good little cocksucker you are… Yeah, like that… Mmmm… Oh yeah… You like it when I play with your ass? Yeah? You want me to push deeper? Faster? Or how about…” Another digit joined the first one, and he began to finger-fuck my hole for real. Whenever he grazed my prostate, I thought I’d faint from pleasure. I whined, which only made him hornier.
Unable to control myself any longer, I came without even touching my dick, and seeing it, he came too. Like always, I swallowed every last drop of his cum, and continued to slobber on his cock afterward, until it went soft in my mouth.
When I finally let it go, I pulled my shorts up, sat on my knees beside him, and appraised his naked body, satiated and sprawled over the sheets of his king-sized bed. He had a strange expression on his face, like he was studying me.
“So,” he said. “You liked that? Me fingering your hole?”
“Yes!” I blurted out emphatically. “It’s the best—except for having a real cock inside.” This pushed him to contemplative silence, so I went on, playing on his curiosity. “I haven’t been fucked in the ass for a very long time. I miss it so much. The feeling of a big, hard cock pushing into me and spreading my hole… God, it drives me wild just thinking about it.”
He scratched his beard. “Huh. So gay guys really do enjoy that stuff?”
“Well, bottoms like me do. Or vers guys. But some are strictly tops and never take a cock up the ass. In the end, everyone gets exactly what they want.”
“I can’t even remember the last time I had anal. I think it was with one of my girlfriends before I met my ex-wife. She was the only one who let me fuck her in the ass—just once or twice. She didn’t particularly like it, but she did it for me. Then we broke up, and…” He waved his hand. “Anyway. Guess women are wired a bit differently. Or maybe my cock’s too big.”
“It is big,” I said, looking at his manhood resting on his stomach, “but even so, I’d love to ride it. I’d love to have it inside me, to have you pound me with it. When I jerk off in my room at night, I fantasize about it.”
My words made his cock grow again like I knew they would. Even though I was aware that he wasn’t attracted to me, he was at least intrigued by the idea of fucking my ass. After a month of constant blowjobs, his cock craved something new, something more. And here was the opportunity he might never find again. “Maybe…” he started. “Maybe, I don’t know, we could try it?”
“Please, Daddy,” I said looking at him, using my best impression of a lost puppy to stir his domineering side and goad him on. “Use me as you want. Put your big dick in my tight hole and fuck me hard.”
My words worked like magic, and his cock rose to its full size, veins bulging, head glistening from precum. He took it in his hand and started playing with it, pulling the foreskin down and up, then stretching the string of precum from the tip with his finger. “Are you sure you can take it?”
“Yes,” I said, breathless from desire. “I’ve been practicing with toys.” I didn’t mention that none of my butt plugs or dildos matched his size, but as long as we had plenty of lube and started slow, I was confident I could manage. Not wanting to seem presumptuous, I also didn’t mention that I’ve been douching myself every day for the past week or so, hoping that his newfound interest in my ass will someday bear fruit.
He got up from the bed, his cock bouncing with every move, and nodded for me to take a doggy-style position. “Okay. Let’s do it.”
Bingo!
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!