Gay Erotic Stories

What can I tell you about Jake? The first thing that comes to mind is that he’s a guy’s guy. You know the sport-playing, crotch-scratching kind of guy who likes fast cars and fast women. He’s always horny. If he’s not having sex, he’s thinking about having sex or talking about having sex. He’s brash and vulgar. The concept of etiquette is lost on this man. He tries to tone it down when in the company of women, but even a toned down Jake can be hard to handle. With the exception of his writing, he tries very hard not to take anything too seriously, not even himself. He’s wild, reckless, and chaotic.

This much you may have gathered from his brief appearances in the previous chapters, but what you may not realize is that you’d be hard pressed to find a man who is more loyal, caring and compassionate than Julian Jacoby (that’s his real name). He’s also very intelligent and creative. After all, the whole concept of the Alphabet Lovers was his idea. His finest quality by far, however, is his charm. It’s the key to his success with the ladies. Sure, at first they may flock to him because of his impish good looks, but it was his seductive way of proposing his indecent desires that got them out of their panties and into his bed.

I don’t know why I was drawn to him. Maybe it was the fact that he was so different from me. The old adage about opposites attracting definitely applied to us. We balanced each other. I was the yin to his yang; he was the anarchy to my order. We trusted each other, depended on each other and took care of each other in our own crazy kind of way. But our relationship, which was so deeply rooted in trust, was based on a lie. You see, in the first year of our friendship, I never told Jake I was gay. Because of a few off-color comments he’d made about gays, I was sure he was not gay friendly. I really liked him, though; I didn’t want to lose his friendship even if it meant pretending to be something I wasn’t.

The closer we got, the harder it became to tell him. He had developed a certain level of comfort with me – like being comfortable enough to traipse around our hotel room naked – that I’m sure never would have developed had he known I was gay. More and more I grew weary of and felt guilty about lying to him and wanted to confess my proclivity for man-to-man sex. I’d just have to deal with the consequences, whatever they would be.

We were in Jake’s favorite diner when I finally decided to break the news to him. I was nervously nursing a cup of coffee and Jake was busy wolfing down a banana split (his favorite delicacy).

“Jake, there’s something I need to tell you. I’ve been meaning to tell you some time now, but I was worried how you’d react to it.”

Jake stopped his feeding frenzy and stared at me with eyes that widened with concern. “What is it?” he mumbled through a mouth of ice cream. I gathered my nerves and blurted out, “Jake, I’m gay.”

He dropped his spoon and gave me the same horrifying look that had haunted my dreams since I decided to tell him – that slack-jawed expression of anger and disbelief that people got on their face right before they kirked out.

“You got me all worked up to tell me that shit? Here I thought you were going to tell me you’re dying or something and all you wanted to tell me is you’re gay! Jesus Christ! That would explain why you’re pounding the big boss’ son.”

“You knew?”

“Uh, yeah. The whole building knows.”

“And it doesn’t bother you?”

“Pfft! Why would it bother me? You can fuck whomever you want, I don’t give a shit.”

“I don’t know; I just figured…”

“This is unbelievable! You got me so worked up with your ‘there’s something I need to tell you,’ bullshit that I can’t even finish my fucking dessert.” He pushed the half-eaten sundae aside and called for the check. “You fags are so fucking dramatic!”

You can imagine that that wasn’t quite the reaction I’d expected. I had no idea he’d be so nonchalant about my sexuality. Not only was he not bothered by it; he was quite familiar with it. As it turned out, half of his college hockey team “took it up the ass whenever they could,” as he so eloquently phrased it. I asked him why he’d never brought it up before to which he responded, “You were so far in the back of the closet, I thought you’d have a coronary if I tried to drag you out.” And to think I was trying to protect his feelings all that time.

Fast-forward five years. We were on assignment in Belize, exploring the Mayan ruins. It was the third day of our visit and we’d returned to the hotel after another exhausting expedition. As we’d done the two days before, I took a shower and got ready for bed. Jake had other plans, however; he wanted to go out and get laid.

I had just crawled into bed when I heard the shower turn off. After a couple of minutes, Jake walked out of the bathroom. He walked around the room, butt naked, toweling off and looking for something to wear; nothing I hadn’t seen him do a dozen times before, but something was different this time. He seemed to be parading about and lingering around in front of me more than normal. He flung the towel over his shoulder and walked toward me.

“Can I ask you a question, John Paul?”

He called me John Paul; it must be serious, I thought. “Sure. What’s on your mind?”

“Have you ever gotten an erection watching me walk around naked?”

I thought about it for a minute. “No, not that I can recall,” I answered. “I usually don’t pay much attention to you.”

“Oh.” He tied the towel around his waist and stood there, quietly pondering something. “So you don’t think I’m attractive?”

“No, I don’t think of you that way.”

“Stop trying to cop out and answer my question. Do you think I’m attractive or not? Like… would you do me?”

“What is this all about?” I asked.

“I dunno. I guess I just need a little fucking assurance from my best friend, but I forgot how uptight you can be… forget it.”

“Alright, alright! I didn’t know it was that important to you.”

I was stunned by Jake’s reaction. I’d never know him to be self-conscious before. As he put it, why should he care how he looks as long as he gets laid. Besides, he knew he was handsome in a young Dennis Quaid kind of way.

“Yeah, sure,” I said, giving in to his silly line of questioning. “I guess I’d throw you a bone.”

“Oh my God, I can’t believe you were just checking me out, you pervert!” Jake yelled. “You were undressing me with your eyes!”

He ran around the room like a fool, holding his hand over his butt as if to protect it from any sudden attacks. I couldn’t believe he had been pulling my leg the whole time.

“You’re such an asshole!” I yelled as I lunged out of bed and wrestled him to the ground.

We rolled around on the floor for a good fifteen minutes trying to subdue one another with a series of pins, headlocks and leg holds. Finally, I got the upper hand, flipped him on his back, straddled his lap, and pinned his wrists to the floor. He struggled, unsuccessfully, to break free. By then, we were both laughing and panting heavily.

My laughter subsided when I felt something hard pressing against the inside of my thigh. Jake stopped laughing too. We sat there, staring at each other, panting, our bodies pressed tightly together, trying to avoid talking about Jake’s hard-on. What was there to talk about anyway? Jake is a horny bastard – we’ve already established that. He gets hard putting on his underwear. The fact that his dick was poking my leg after five minutes of direct stimulation meant absolutely nothing. But, if that’s the case, why did he have that wicked gleam in his eyes. I’d seen it before when he was on the prowl now it was directed towards me. And what was that feeling in the pit of my stomach?

“You’d better hurry up and get dressed before all the pretty chicks are taken,” I said, snapping out of my catatonic gaze and quickly standing up.

I helped him get to his feet. I tried not looking at his erection, but he’d lost his towel early in the match so there was nothing but him, his noticeable boner and me. My eyes wandered down to it – only for a moment. I blushed and quickly averted my eyes, hoping he hadn’t noticed. He was still staring at me – he noticed.

“Yeah, right, the ladies are calling,” he said, grabbing his towel and pointlessly holding it around his waist. It only made his erection more obvious. “You sure I can’t talk you into joining me?”

“No thanks. That wrestling drained the last bit of energy I had. You go on and have a good time.”

“Okay… Don’t wait up.” He flashed me a weak smile and headed into the bathroom to change.

I slithered into bed and waited for Jake to leave. Twenty or thirty agonizing minutes later, Jake turned off the lights and quietly made his exit. I spent the rest of the evening laying in bed, tossing and turning, wishing for the numbing arrival of sleep but it never came. I couldn’t get my mind off of what had just happened.

The fact that Jake got an erection during our horseplay seemed harmless enough. His hungry, lascivious stare was more than a bit unsettling though. What bothered me the most, however, was how it made me feel. For the first time since we met, I felt deep, burning lust in my heart for my best friend… and it sickened me. I had always thought he was a good-looking guy, a harmless assessment that was the extent of anything remotely sexual between us. That’s how I wanted to stay. But, in one fleeting moment, my relationship with Jake, which had grown into something so pure and strong, would be forever corrupted. Even as I lay in bed, convincing myself that it was wrong to have these thoughts about him, I couldn’t stop thinking about his naked body.

The sound of Jake’s keys in the door startled me – I didn’t expect to see him until the next morning. I quickly glanced at the clock. It was a few minutes past 10 o’clock; Jake had only been gone a couple of hours. I wasn’t ready to talk to him while pretending nothing had happened, so I closed my eyes and pretended to be asleep.

I watched Jake through half-closed lids as he stumbled around in the dark, bumping into furniture and knocking things over until he found his way to the space between our beds. There, he stripped down to his underwear and took a seat on the side of the bed facing mine. He sat there quietly for a few minutes with his head in his hands.

“I know you’re awake,” he said. “I think I broke my toe on the desk chair just to make sure you’re awake… you’d better be awake.”

I opened my eyes. “Yeah, I’m awake.”

“I think we need to talk.”

“I’m tired Jake; can’t this wait until morning?”

“No,” he answered, switching on the lamp between our beds. “We need to talk right now.”

“Fine,” I said, propping myself up in bed. “What do you want to talk about?”

“Don’t play dumb; you know what I want to talk about.”

Already, I found myself unconsciously examining his body and noticing things about him I’d never paid attention to before. Like, how fit he was despite the fact that I’d never seen him so much as break into a jog. He certainly was no hard-body, but he was definitely trim. I never thought much about the light layer of brown fur that coated his chest and stomach, or how well he filled out the pouch of his tight, gray boxer briefs. And for the first time, I was keenly aware of the meat that was packing them and how it felt hot and steely against my thigh. I felt a stir in my heart and my crotch. “This is Jake,” I argued to myself, trying to rebuff my feelings, but they would not be denied.

Even if I couldn’t shake the feelings, I didn’t want Jake to know about them. “If you’re referring to that little incident earlier, there’s nothing to talk about,” I said as coolly as possible. “We were horsing around and you got a boner. You get them all the time; I don’t see why this time should be any different.”

“It’s different because we’ve messed around before and that’s never happened.”

“Okay, so it’s never happened before. It happened tonight… get over it.”

“There’s more to it than that, Paulie, and you know it. I felt…something between us when we were lying there. I don’t know what it was, but it was strong…and I know you felt it too.”

The stirring in my shorts returned, more powerful than before. “I don’t know what you’re talking about. I didn’t feel anything,” I said and rolled on my side, turning my back to him.

He didn’t say anything for a while, but I could feel his eyes on me. “I met this chick tonight… she was a prime piece. She was all over me, backing that plump ass up against my crotch, pushing her breasts in my face. She let me put my hand up her skirt and feel her cunny. Oh man, she was wet. We were just about to go back to her place, when I froze. Do you know why I froze?”

“I really don’t want to hear about this right now.” I pulled the covers over my head and tried to ignore the pounding in my head and the throbbing in my crotch. “I’ll tell you why: because all I could think about is how I felt with you on top of…” “Shut up!” I screamed, sitting up in my bed. “I don’t want to hear this! I don’t want to hear you say something stupid like how thrilling it was to feel the strength of another man holding you or how you felt electricity in the air. You’re just confused and horny. All you need is some good pussy and you’ll forget all about this nonsense.”

“Why are you freaking out? I thought you, of all people, would understand how I felt.” He moved from his bed to mind, took a seat next to me much closer than he should have, and leaned over my lap.

“Because you’re not gay,” I mumbled, finding it hard to concentrate or breathe with the heat of his naked flesh pressing against mine.

“You know what your problem is…what your problem has always been? You need to define everything: your sexuality, your feelings, and our friendship. Life isn’t that simple. Now I don’t know what these emotions mean; you know, whether it means I’m gay or bi or whatever. All I know is that I like what I felt with you and I want to explore those feelings.”

I was powerless to argue. I’d never felt this way about Jake before. I had loved Jake for years, as a friend, and now I found myself lusting for him. It seemed so dirty to me but Jake made it seem so logical. That’s what he does best: make sense out of nonsense.

I leaned forward and pressed my lips against his. It wasn’t so much a kiss as it was a test to see if he was teasing me again. I doubt he’d ever felt another man’s lips on his – not even his father’s. He retreated from the new sensation.

“I told you this wasn’t right,” I said.

“No, it’s alright. It was just a little weird at first, but I’m cool now.”

To prove it he leaned in for another go at it. This time it was the real deal. Jake had recounted, in great detail, many of his sexual escapades. He rarely kissed his partner; he said it made things too personal. So I was surprised at how gifted he was at the art. He teased me with short, playful pecks then attacked my mouth with his lips and tongue that was to follow. He had me craving his mouth; greedily sucking his tongue; wishing I could choke on it.

I lied back, pulling Jake down on top of me. He rested his meaty paw on my side while his lips started to explore my ears and neck. I was aware of his fingers grazing my sides then timidly sliding across my tight stomach. Jake used to say he envied of my washboard abs – the same abs he was now worshipping with his gentle touch. His adoring exploration came to an abrupt end when his pinky slipped under the waistband of my shorts.

Meanwhile, his mouth had meandered down the length of my neck, across my shoulder blade to my chest, and was slowly approaching my sensitive nipple. As his tongue took its first playful swat at my tiny little nub, I grabbed his hand and slid it into my boxers. He stopped licking my tit when his palm made contact with my stiff cock. He wrapped his fingers around it, gave it a firm squeeze then looked at me.

“I haven’t touched another dude’s piece since Tommy Mancini and I jerked each other off at summer camp,” he admitted.

His stroke my cock a few times then cupped my balls in his hands and fumbled with them for a bit. I closed my eyes and concentrated on the incredible feeling of Jake vigorously, handling my equipment. “Tommy was one lucky kid,” I murmured.

Jake’s big hand continued to grope around inside my shorts, alternating between cock stroking and ball juggling. He’d abandoned his nipple licking to focus on this new activity, but I didn’t mind the trade off. He stopped fondling my package just long enough to slide my boxers off my hips so that he’d have more room to play. I kicked them off the rest of the way and was completely exposed and available to him. Jake took a moment to study me thoroughly with his eyes and hands.

He turned around on the bed so that we were in a 69 position. He rested his head on my thigh and continued his stroking where he left off. His hips rested near my head. I eyed the sizeable tent his cock made in his briefs. I reached out and grabbed the bundle then sucked it into my mouth, getting the gray cloth wet with my drool. Jake jumped in surprise, but I had a firm grip on his package so he wasn’t going far.

“It’s too late to be nervous now,” I said, pulling down on his waistband.

“Does that look like I’m nervous?” he asked when his dick sprung free and slapped me on the lips.

“Not at all”, I said as I was reintroduced to his fat seven-inch cock which stood stiff and proud. I’d only seen it hard once and even then I didn’t really notice how fucking thick it was. I pictured some little blonde number squealing as he stuffed that chubby dick into her tight little pussy then I imagined how it would feel crammed down my throat or up my eager ass. It would be a struggled to do either; a struggle I was looking forward to facing. I grabbed it and licked a tiny pearl of pre-cum from the tip then swabbed the swollen head with my tongue. His fuck stick twitched excitedly. I opened my mouth wide, slowly inched that fatty in until my mouth was chock full of his tasty man meat.

“Holy Shit!” he howled. “No chick has ever done that before. God, it feels good!”

I was glad he was already so pleased because my jaw was already aching and I didn’t think I could keep that thing in my mouth too much longer. Anyway, I started to clumsily suck Jake’s dick. I slobbered and drooled more than I sucked, but Jake didn’t seem to mind. A couple of minutes into it, he lifted his leg and began thrusting his hips back and forth. I relaxed and let him do the work. As he continued to slowly fuck my mouth with his porker, I slurped and gurgled, trying to keep the drool to a minimum.

I was too busy concentrating on trying to give Jake a good blowjob that I hardly noticed he’d turned his attention back to stroking my neglected cock. He had my undivided attention, however, when I felt his tongue pensively circling my knob. His hips stopped thrusting and I let his dick pop out of my mouth so that I could fully appreciate his inaugural effort.

He was damn good for a novice, which confirmed my theory that men, straight or gay, are instinctively good at sucking cock. Some, of course, are better than others; Jake was well on his way to being one of the better ones. I was impressed that he managed to swallow more than half of my 10-incher and shocked at how eagerly he gobbled it down. It’s one thing to let a guy suck or jerk you off; or even to give his dick a good yank. I’ve heard many straight men say that they had either participated in or would participate in said activities just out of curiosity. Sucking a guy’s cock, though, is something that even the most curious and open-minded straight men shy away from.

“Fuck yeah, man, suck that cock,” I purred.

Jake obediently sucked on my cock while his hands made nice with balls. Not to be outdone by a rookie, I went back to servicing him; this time, I was going for his cherry ass.

I grabbed his round, firm ass cheeks and felt them tense up immediately, denying me access to the goods. I flicked my tongue over his perineum (you know, that really sensitive strip of skin between your nuts and your ass). His cheeks relaxed to reveal his tight, pink, unused pucker. I immediately probed it with my tongue. Jake hummed his approval with my cock still implanted in his mouth.

As my tongue wormed its way further up his chute, Jake grabbed onto me and repositioned us so that he was on top of me, essentially sitting on my face. With his ass hovering above my awaiting mouth, I was able to eat him up properly. I licked and sucked and blew on his brownie until it was quivering with excitement. By the way he was moaning and writhing, I could only speculate that he wanted more. I tickled his sphincter with the tip of my finger and watched it wink back at me. Oh yeah, he wanted more. I applied a little pressure. Jake pushed back and my digit slid in up to the third knuckle. Jake pulled his mouth off my dick and used his spit to continue jerking it. “I can usually take two or three,” he said.

I should have known, with all the women he’s messed around with, that I wasn’t the first one to play with his ass. So, on his recommendation, I eased two more fingers into his anus, which he accepted with a throaty groan. Jake stroked and licked my cock as I worked my fingers around inside his squishy ass. It felt so warm and tight – my dick was literally twitching to get inside. Jake must have noticed.

“You want to fuck me, don’t you?” he asked. I could hear the concern in his voice.

“You don’t how much I want to…but I can understand if you don’t want to.”

He gave my cock a few more strokes while he considered my proposal. I was harder than I’d ever been, just anticipating the chance of fucking my best friend. I fingered him as deep as I could hoping it sway his decision. I hit his spot and he let out another husky wail.

“Shit yeah,” he finally consented. “Just take it easy, okay?”

“I will,” I promised.

I told him to lie flat on his stomach. As much as I wanted to look into his eyes as I took his virginity, I thought he’d be able to relax more in that position. He hopped off of me and lay down beside me. I crawled on top of him, spread his cheeks apart, dropped a good load of spit on his crack and worked it in with my thumb. He was as wet and open as he was going to get, so I aimed my prick at his hole and pushed. Jake tensed up. I told him to relax and as he did, my cock broke through the first ring then the second one.

“Aw fuck that hurts!” he yelped. I felt him tense up again.

“I know, I know,” I said, massaging his shoulders. “But the worst part is over… now, just relax.”

His body melted under my gentle caress and his ass opened up a bit. I applied more pressure and my cock invaded his rectum inch by inch. He took it like a champ and, finally, I had all ten up his rear. I laid my body on top of his and kissed him on the shoulder. “I’m in,” I whispered.

“Yeah, I know,” he grunted.

“You okay?”

“It feels weird, but I’m okay though.”

I eased my cock in and out of him slightly. “Does that feel better?” I asked.

His only response was, “Mmmm.”

It was the only response I needed. Pushing up on my hands, I continued to leisurely open up his uncharted depths. There’s nothing quite like breaking in a virgin ass; plunging through its exquisite tightness; feeling it slowly submit; experiencing the onset of a steady milking rhythm as you repeatedly awaken feelings your partner’s never felt before. It’s just what I needed to wash away the last traces of regret. I watched Jake’s rugged features flush and contort and listened to his soft, throaty grunts of gratification egging me on. The orientation period was over; it was time to get to the real business of fucking.

I put my back into it. The clap, clap, clap of our colliding flesh grew louder. His tight, bouncy rump served as the springboard for my thrusting. I drove a louder moan out of him each time my dick bottomed out in his colon.

“Fuck my ass,” he growled softly. Jake liked dirty talk; he’d mentioned it once before and I’d heard him through a hotel wall a time or two. “Ah yeah, ride my ass!”

I gave his ass a firm slap. “You like my dick up your ass, don’t you, you horny fucker?” I felt him backing up to meet my thrusts. He was really getting into it. “That’s right, back that thing up. Come get my dick.” He was grunting and rutting so hard it was difficult to keep up with him. “Aw fuck, Jake, you’re gonna make me cum! You want me to cum in your ass?”

“Yeah,” he groaned, “dump it in my ass. That’ll be some freaky shit.”

“Okay, one load coming up.”

I held his hips firmly and pounded his ass thoroughly. The tingling started in my toes, worked its way up my legs and landed in the pit of my stomach. I was fucking him with long, deep thrusts now – my orgasm was only seconds away. “Oh fuck, here it comes!!”

I thrust my cock as deep in Jake’s bowels as it would go and filled him with my cream. I swear I could feel my balls pumping my seed out. I pulled out in time to drop the last couple of spurts on his newly stretched hole. It pooled up in the gaping orifice before I shoved it in with the tip of my cock.

“Happy now?” I asked, drilling my softening cock back into his cum-filled ass.

“Not yet,” he said, wiggling around on my pole. “I haven’t fucked you yet.”

I grinned. “Well, let’s just see what I can do about that.”

I pulled my dick out of Jake’s slimy ass and turned him over on his back. His prick hadn’t softened at all; in fact, it looked bigger and harder than it was when I was chowing down on it. “I got some lube if you want it,” Jake offered.

“Real men don’t use lube,” I said dropping a big gob of spit on his fat cock head.

Me and my damn bravado--that donkey dick was going to split me apart! I coated his organ with saliva, getting it as wet as I could, and then poised myself above him. I lowered my hip until I felt his cock poking at my opening. I took a deep breath and pressed on. The thick, mushroom-shaped head slid in, stretching me to my limits. It felt like being fucked for the first time, but I refused to let Jake know how much it hurt. He would have wanted to stop and I wanted badly to feel him inside of me. I closed my eyes and focused on taking the shaft, which was just as thick as the tip. I worked my hips, bounced up and down on his unforgiving cock, and until I felt his balls pressed against my ass.

“Damn, that’s tight,” Jake pointed out.

“You’re telling me,” I said, flashing him a wicked grin to mask the grimace of pain.

During the ordeal, my cock had gotten hard again. I guess despite the pain, a cock in my ass still gets me hard. I wiggled my hips to keep him happy long enough for my ass to adjust to his fat dick. He had the biggest shit-eating grin on his face from the moment he felt his cock surrounded by my hot, squishy insides. The added pleasure of me bouncing on his schlong sent him into convulsions.

“Aw man, Paulie, we shoulda done this a long time ago. Your ass is so hot and tight. It’s almost better than pussy.”

“Almost?” I asked, clamping down on his throbbing prick.

That little trick left him speechless. I started bouncing on him again, sliding further up his cock with each stroke and ending each thrust with a tight wiggle of the hips. Soon, there was no pain, only the satisfying feeling of his pole stimulating every nerve in my bunghole. I rode him so long and hard my legs started to cramp, but I wasn’t going to stop until I had his load. Jake grabbed my cock, which had been wildly smacking against his stomach.

“I want you to cum on me,” he said with a devilish grin. His words alone were enough to make me pop my cork, but I somehow kept my cool. “C’mon ride that cock, Paulie… give me that tight ass!”

I fucked myself with his cock while he pulled on my crank and spat out naughty comments. I may have been able to fend off my orgasm before but there was no holding it back this time. It only took a few more tight-fisted strokes of Jake’s hand to bring me to my second explosion. The first syrupy stream landed right on his lips and the other six or seven splattered all over his chest and stomach.

No sooner had I emptied my balls than Jake announced his orgasm. He loaded up my colon with gallons of his hot, sticky, straight-boy spooge then churned it up with his hefty ass popper. I rested on his heaving chest and gazed upon his beaming face. He licked my cum off of his lips and smiled. I smiled back then rolled off and settled on the bed next to him.

We lay silently in bed for a few minutes, staring at the ceiling, catching our breath and gathering our thoughts. Jake was the first to speak, rolling on his side to face me.

“What now?” he asked.

I shrugged. “I don’t know.”

We stayed up all night talking about what we had just done. I won’t bore you with the details but suffice it to say that we were able to reconcile our friendship and our carnal acts. There was no weirdness between us. If anything, we were even more comfortable around each other. Every now and then we’d fool around, usually when we were drunk, but Jake still loved the pussy and got it whenever he could. And I still had 16 more letters of the alphabet to explore.