He messaged me around eight that night that he was up for some Daredevil if I was still watching. I sent him back a picture of my feet propped up and the TV visible through them. "Door's open!" I added. Ten minutes later he walked in my living room and plopped down on the couch and leaned back into it with a sigh.
I noticed right away that his leg was comfortably pressed against mine, and I slid into him so that we were side to side. We watched the last twenty minutes of the episode and pretended we weren't taking every opportunity to touch one another. When the last credits rolled, Austin grabbed the remote and made a bee-line for the adult channels.
That was enough for me to feel comfortable massaging his dick through his jeans. The grin he returned me as I squeezed his cock was so sexy I felt my balls hitch. I casually pressed and rubbed while he breezed through the interface with an expert's touch and queued up a bunch of anal porn. I guess he wasn't lying when he said it was his thing.
"What is it you like about anal porn?" I said, curious. I don't mind seeing someone getting their ass blown out either, but I wanted to learn a little bit about him.
He squirmed a bit, looking kinda uncomfortable. "Hey, you don't have to be embarrassed that you like anal sex," I said, giving him a serious squeeze and taking the liberty to undo his belt buckle. "I can feel how much you like watching it, right here in your dick. I just want to know what it is you focus on, so I can make sure I have a lot of it for you watch." I felt his dick literally throb under my hands.
I leaned in a little closer to his ear. "There's no shame if you get hard watching someone get their ass properly fucked open," I told him. His hips thrust up and pressed into my hand. I could feel his hard penis and it's heat on my palm and I decided to just go for it. I pulled open his pants, and reached under his briefs and grabbed his fat, hard dick. It was already dripping in my hand as it sprang free. He moaned softly as my fingers closed around his hot skin. I ran my thumb up the underside and pressed a fresh bubble of spuzz out of the tip.
I don't know about you, but I like to use those first little pearls of precum with my thumb. Here's what I do; I slide the first few drops under the glans, just under the opening. Then, gently but firmly, I swirl my fingers around the ridge of the head and spread the cummy slickness all over it. My goal is to cover the whole head with precum, so my fingers and thumb can freely slide over the ridges of cockhead and the spot just where they meet underneath. I've been told it feels like fucking a warm washing machine. You gotta be careful though, because if your dude has a hair trigger, this can make him pop real early.
"I guess I like seeing it," he said. "Y'know, that cock going in. Her ass." He thrust his dick up and down in my hands, noticeably harder than it was when I'd first taken it out. "I like seeing their expression change when they bottom out." He hissed as my fingers swirled wetly through the sheen of precum I'd smeared on his fat cockhead.
I gave his throbber a break and cupped his balls for a bit. There were smears of his precum all down his cock and he was still leaking more. It was like he'd been saving it up or something. His balls felt real heavy, like little doorknobs in his sack.
"Have you ever fucked someone's ass?" I asked, specifically keeping it gender neutral. I rolled his balls gently in my hands, breathing hard and close on his cock.
"No," he smiled. "I haven't had too many girlfriends, and it just never came up."
"Hmmm," I said, getting close and sucking his precum off his dick. "So I guess you've never been fucked either?"
He hissed at the sudden feeling of my mouth on his spermy-tasting cock. "No," he replied, "have you?"
"Sometimes," I said. Which was true. Nine times out of ten, I like to top. There's something about the way an ass clenches up around my cock that I've always loved. I like feeling myself inside someone, be it mouth, ass or even pussy. I like pushing open a reluctant hole and feeling that resistance ease away until I've left it loose and floppy and probably dripping.
One of my first lovers made an excellent point the night he took my anal virginity. "If you want to fuck ass, it's important to take it in your ass too." He said this just as his long cock first popped into my cherry hole, making me wince. "That way, you know what they're feeling, and you know how to fuck them. You don't want to blow their asshole out." He was true to his word that night, and didn't blow my asshole out. Although not for want of trying. Even by the third round, when his cock was red and slightly chafed and that final load was barely two squirts, he never hurt me and I never bled.
"Sometimes it feels really good to be stretched out and filled." I said, sucking Austin's beautiful dick with it's fat head into my mouth. "You see how she likes her ass all topped up?" I asked, directing his attention to the anal porn he'd selected. "It's the feeling of getting her insides pushed around that makes her cum."
Austin groaned, and thrust his cock deeper into my mouth. I took the opportunity to massage under his balls, getting closer to his asshole. I wasn't sure if he was quite ready for that, so I didn't push too far and stroked his balls at the same time. We spent a few minutes in silence, me softly sucking his dick and pressing on his taint. He surfed the porn a little as his cock got harder in my mouth. He'd been steadily gobbing his precum into my mouth this whole time, and his whole dick was tasting like sperm.
I took a breather and peeked at what he was watching. A brunette was kneeling in front of a giant cock, begging for his cum. I slurped noisily on his balls as the brunette's face was just obliterated by cum. As she gasped on screen and swallowed what she could, I said "Oh, that's my thing," rubbing my mouth on the soft skin of his sack. "I'm a cum head."
"I like cum too," gasped Austin. I sucked on his cock again, taking it deep. As I pressed my nose into his belly, I let my finger slide from his taint to his ass, gently swirling. I wanted him to start feeling the nerves down there while I pleasured his cock. I made sure my tongue was working the bottom of his hard shaft while I throated him.
He didn't resist, and his cock pulsed in my mouth as my finger put slight pressure on his entry. I made some eye contact from below his dick. "Is it okay okay if I play with your hole a little?" Maybe it wasn't fair to ask that of someone who's dick was still slimy from my mouth, but he answered - a little quickly - that it sure was. His words, not mine.
As if to reiterate, he pressed himself down on my finger, sliding it in up to the second knuckle. I let him get used to the feeling of being penetrated, making sure to keep his dick wet and warm. He gently worked his ass on my finger, working it in and out at his own pace. His cock was leaking pre-cum all over the place as I stroked him with one hand and fingered him with the other.
I paid close attention to his cock. This was a critical time. I wanted him excited and hard and enjoying the new sensations in his ass, but I didn't want him to cum too fast. I could tell his ass was more virgin than it wasn't, and I needed to be careful about stretching him open like this. Even though he was taking the one finger well (it wasn't the first finger in his ass, I suspected), it's easy to go too hard too fast. This was where it came in handy to know how it felt to have something in your asshole and how to work one open.
I'm not the best at licking ass, I admit. There are some people who just make a butthole tingle with their mouth, but I do my best. Austin's little ring was fluttering around my finger when I ran my tongue along the tight, bunching rim of his asshole. My spit added some needed lube, and he took my whole finger deep into himself. After feeling the way his hole squeezed the tip of my tongue, I decided he was ready for another finger.
I moved my mouth from his ass to his balls. I kissed them and kept eye contact as I slipped two fingers into his wet hole. He gasped a bit and held still, breathing shallowly. I felt his ass tighten, then relax, tighten again, then relax. I slathered his dick with wet kisses and deep throats as he slowly worked both my fingers in as deep as they'd go.
I let him watch some porn while he was getting his dick sucked. He'd worked his ass open on my fingers enough for his hole to start making wet and sloppy noises. I had to take a bit of a break to rest my mouth, so I jerked him off and let his ass work on my fingers. Every now and then, I would goose his prostate, making him jump and gasp. Again, that's something to be careful with. It's real easy to accidentally send a guy straight to cumtown massaging that little bean. I didn't want Austin to lose his load just yet, not when he was doing so well with his stretching.
"I like how hot it is inside your ass, Austin," I said, sincerely. "I like how you opened your ass up for me, just like those women on the tv."
He sighed and his dick pulsed and still more pre-cum slowly oozed down his shaft for me to lick up. I peeked over to see what porn he was currently playing, and I was surprised to see it was a collection of gay facials. I smiled in approval as a handsome stud on the screen with two days worth of beard swallowed what looked like a quarter-pint of sperm.
"You feel like feeding me, Austin?" I was pretty sure he wanted to, but I wanted to hear him tell me. "You want me to swallow your load?"
"Yes, I do." He said, thrusting himself on my fingers urgently.