First Time with a Guy: A True Story

The following is a true story from my personal life. Some identifying details are omitted. I am writing this so I can relive the awesome memory and not forget. Hope you enjoy.

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I first began to appreciate the male form when I was a teenager. Before that I was only turned on by women, and I still am. But I have always been a bit of a nonconformist, so I think my sexual attraction to men probably came out of my desire just to try something new. To this day, I have preferred to get off by fantasizing about having sex with someone that I know. The porn has always been more of a background stimulant—the real turn on is the familiar face in my mind's eye.

Somewhere along the line, I grew bored of jacking it to the same girls I had been attracted to for years. You can only stroke it to good old Mary a finite number of times. I don't remember how the thought first occurred to me, but there was this guy who worked at the same place I did. Real attractive dude—tan, thin, very chiseled face. I found myself staring at him all the time, but for a while I never thought about him sexually. Until one day I did.

I quickly found that thinking about fucking Steve made me really hard. Then I went a step further, looking up gay porn on my laptop. It was a whole new world, one that felt almost taboo, and it turned me on big time. That night I jerked my cock fantasizing about Steve. I still remember the orgasm—it was so intense, just a huge rush of pleasure.

From then on I was hooked. Over time, gay porn came to replace straight as my primary jerk off material. But for eight years I did not act on this secret fantasy. Nobody in my life—and I mean nobody—has a clue that I often fantasize about sex with men. After all, I still date women and had a relationship that lasted several years. I guess you could classify me as some sort of bisexual. Truth is that my sex life is no one's business, and I would like it to stay that way. After I broke up with my last girlfriend, though, I knew the time had come. I needed to act on this fantasy.

I started by going on Craigslist, which is a surprisingly good source for legit hookups. My first gay experience came in a dorm room with a guy who unfortunately looked nothing like his pictures. We made out and sucked each other off, but the whole fiasco was so bad that I almost gave up men as a lost cause. But I kept going, hoping for something hot. I got three more hookups that consisted of more kissing and oral, but they were nothing special. What I really wanted to do was fuck, but none of these guys were up for that, plus they weren't that attractive in real life. One thing I quickly learned though—sucking a cock is pretty easy. Even swallowing cum isn't so bad. Girls make a big deal out of it blowjobs, but now I know that licking a pussy is actually much more difficult.

Anyway, back to my gay sex adventures. After a few months I realized that the whole Craigslist thing wasn't working the way I had hoped, so I finally grew some balls and downloaded Grindr. Forgive me for my choice of words, but it really is a smorgasbord of hot men. I'm a sucker for a tight body and a handsome face, and Grindr is filled with my type. That's where I met Matt.

At first, all I could see was his profile picture—a shot of his rippling abs. I could also see from his description that he was 25, Asian, tall, and a bottom. We went through the customary ritual, starting with the initial greeting and exchange of pictures. After seeing his chiseled face, short hair, and tight, muscular body, I knew I wanted him very badly. I tried not to get too excited, though, because I had previously messaged hot guys who seemed into it and ready to meet...and then of course I never heard from them again.

But Matt gave me the key information that usually seals the deal: an address and a time. I'm actually going to fuck a guy in the ass tonight, I thought. But even with this win, I could not declare victory yet. I once drove to an apartment building only to have the guy never answer his phone, so I tried to keep my enthusiasm in check.

But a few hours later, I was shaking Matt's hand in front of his house. He was just as hot in real life as in his pictures. Without further ado, he led me inside and upstairs to his deserted apartment. There was a little small talk, but we didn't waste much time once the two of us were sitting on the bed.

"So, you've done this Grindr thing before?" I offered clumsily.

"Yeah," he answered, smiling as he leaned in to kiss me.

We made out furiously in his bed, getting our arms and legs completely tangled together. I felt up and down his hard abs, feeling his toned biceps, grasping for his stiff cock. Our lips were a symphony as we explored each other's mouths with our tongues. I sucked on his lower lip, then moved to his ears and neck. Matt moaned in pleasure at that, and before long our shirts were off, then our pants and boxers. I worked my way down to his pecs, sucking on his nipples, then kissing his taut abs. When I got to his stiff tool, I teased him a bit by kissing every area except for the cock itself. I licked his balls and took each nut gently into my mouth, tonguing every inch of his sack. Matt went wild at that, then moaned loudly when I finally put his dick into my mouth. I sucked hard on his meat, watching him throw back his head in pleasure.

I told myself a thousand times that I would never want to rim a guy, but in the moment all I wanted was to taste his ass. Without any hesitation I shoved his legs up and stuck my face into his crack, licking and flicking my tongue across his puckered butthole. Matt obviously enjoyed this, sighing in ecstasy even though it was my first time tonguing a dude's ass. After being thoroughly rimmed, he pulled me up and brought me back in for more kissing.

"You wanna fuck?" I asked.

"What position?" he shot back, grinning mischievously.

I stammered a bit. I didn't think this far ahead! "It's up to you, man," I said.

"How about I ride you," he said.

I didn't need to hear anything else. I got off the bed and fished around in my discarded pants for a condom while Matt located his lube. I laid on my back while he lubed up my sheathed cock, then his own asshole. With practiced agility, he lowered himself slowly onto my cock. It was a truly a surreal experience, having this smoking hot dude riding my dick. I can't believe this is happening. It took every fiber of discipline in my body not to cum then and there. Luckily he started off slow, getting used to my seven inches inside his ass. I felt up his fit body, running my hands over his hard chest and abs, then grabbed his hips as he moved up and down my dick. We almost seemed to be in synch, because he started riding me really well as soon as I got used to the feeling of my cock being up his tight asshole. Still, it didn't take me long to edge toward climax.

"Let's switch positions," I suggested, hoping that the respite might calm my swelling balls a bit.

Matt hopped off my dick and positioned himself on all fours in front of me, sticking his ass into the air. I mounted his tight little muscle butt from behind, slowly working my cock into him, being sure to check to see if he was handling it. I began to increase the pace, and soon I was fucking Matt's ass full force. I pounded the hell out of his behind, my hips slamming into his ass cheeks and fucking him right into the bed as he moaned in uncontrolled pleasure. A few times I pulled him up so we could kiss, our now sweaty bodies pressed closely together. Honest to God I fucked that guy as hard as I could, and he took my cock like an absolute champ and begged for more.

"Oh fuck, fuck, fuck me, fuck my ass!" Matt moaned again and again.

Before long I was close to cumming again, so I flipped him onto his back to fuck him missionary. Here I was able to get close to his handsome face, and he wrapped his legs around me as I thrust into his ass and made out with him. Matt's hole tightened when he started jerking his cock and getting closer to orgasm.

"I want you to cum in my ass," he implored. "Please cum, that would be so hot."

When he finally shot his load all over his muscled body, his asshole clenched around my cock much harder than any pussy. It felt so damn good that I just started slamming him, and our moans blended together as I exploded inside his butt. I only saw stars as wave after wave of cum rushed through my balls, filling the condom with my load. Totally spent, I collapsed beside him and we gently made out a bit more.

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We have tentatively agreed to hook up again. Whether or not that happens, I will only say one thing: every dude should try gay sex. Fuck what society thinks. Get out there and start living your fantasy...I know most you have probably thought about it.