From Undercover to Under him

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The club music was loud and the lights were flashing. The crowd around me seemed to be moving in time with it, swaying back-and forth as they danced at their tables or stood on the dance floor where a DJ spun records for them. I felt like an outsider there though; too serious by far to fit into this scene of fellow twenty-somethings who had come out tonight dressed up in tight jeans that showed off their asses while low cut tops displayed cleavage. You could tell that it was a gay club, because there were so few women, and guys consistently wandered to the back. However, unlike many, this one seemed to prefer maintaining an illusion of civility; at least in the main space, they kept tighter rules against overt sexual acts.

My name is Alvaro Crawford, and I'm a 26-year old police detective. It was all I'd ever wanted to be when I grew up, and I recently got promoted to one. I'd worked my ass off to get where I am, and I was damn proud of it.

Tonight, I was undercover in this club, as a bartender. I'd been doing it on-and-off for about two weeks. One of the patrons here was dealing, and the plan was for me to get information on his supplier. Rumor has it, the supplier was a lesser-known criminal organization, and they were becoming more and more active and dominant in the drug market. Someone has to stop them before they become a serious problem in the city, and I was assigned to go undercover and find the dealer, a guy named Blake "Big Daddy" Davis. If he's really involved, then maybe we can take his suppliers down once and for all, and maybe even get rid of some other dealers along the way. If not, well...I'll still have gotten valuable intel from Big Daddy's own operation. Either outcome would work just fine with me!

I was tending the bar, making drinks for customers - mostly some gay guys, who seemed to flirt a lot with me, some girls looking for fun, and rarely, their boyfriends. The ladies were hot, but they assumed I was gay, so they didn't flirt as much (but when they did, it was certainly a treat). In this sexually-charged environment, to think about anything else besides getting laid right now wasn't something I found easy to do, given how horny these nights usually turned out to be. My dick always rose quickly whenever I saw any cute girl wearing next to nothing and since it already happened several times today, I figured why fight it? I'd just stay behind the bar until it went down, and rub one out when I got home.

Thankfully, my experience tending bar in college gave me the necessary skills to maintain my cover (one reason I was chosen for this assignment). So far, I hadn't seen Davis, but we had good intel that he would almost certainly be here tonight. It wasn't too long into the evening that I finally spotted him, over on the dance floor. He was walking over here to order a drink.

He was younger than you'd expect for a guy who's nickname was "Big Daddy", at only 23 years old, but he was still a highly successful dealer. "Hey man, can I get you something?" I called to him from the end of the counter near the cash register. 

His eyes met mine briefly, then looked away again. But after a moment, he came closer and started talking to me anyway: "Yeah, sure thing, can I get a beer?" he said nervously, turning his head toward the door leading outside onto the patio. This place had outdoor seating during nice weather months, which made sense considering how warm the city gets most Summer days. But right now, it was a crisp Fall evening, very close to Winter.

I handed him his beer, and he drank it as he waited near the patio. Within a few minutes, someone came up to him; they made a quick exchange, almost certainly a drug deal. I glanced over, making note of the transaction, before Blake and the man went their separate ways, and Blake returned to the dance floor.

Some time passed before Blake returned for another drink; you could tell he'd been sweating from dancing all night. "Can I get another beer?" he asked. I obliged, before making my move.

"Hey, so I saw you earlier and I hear...you deal some good shit."

Blake looked around to make sure nobody was watching. "Yeah man, I do. I like to make the rounds at the local clubs," he said. He was already giving me some valuable intel on his own operation; let's see if I could get anything on his suppliers too.

"Cool, I might be lookin' for a new dealer, my old one got snatched up," I said. A complete lie of course, as I'd never had a "dealer", but hopefully it would sell me as a realistic buyer.

"Cool man, I can get you some. I don't have anymore on me though," he said. "If you're lookin' to buy tonight, you could come back to my place later," he said, in a voice that one might mistake for...almost seductive? I ignored that and answered his question.

"Sure man, that sounds great!" I saw a smirk appear across his face, but thought nothing of it. He gave me his address, and went back to dancing.

***

Later that night, I showed up at Blake's apartment. "Hey man, thanks for meeting me here. Follow me inside, I gotta show ya somethin'," he told me, opening the front door to lead me in. He smiled at me, and grabbed my butt as we walked.

"Gotta say man, you've got a real nice ass," he complimented. "And you're hot as fuck, too. I can tell you work out!"

"Thanks man, I like to keep in shape," I replied anxiously.

"It shows, dude!"

We walked through the living room, past pictures of Blake standing with various celebrities, and into a large kitchen. At first glance, I couldn't help but notice how sexy the house smelled. There was a hint of cologne that caught my nose, and fresh bread baking in an oven somewhere nearby added its own aroma to what I was smelling. We entered the dining area, and stopped there.

"Here's my stash," he said, opening a cabinet that would probably be tough to notice otherwise. Inside, I saw packages of marijuana, certainly enough to get him and his supplier on intent to distribute.

"Nice, man. How good is it? Where do you get it from?" I asked him.

"I know a guy. Has real good stuff," he replied. "Before we do business though..." Blake looked me up and down. "I could tell you were checking me out in the club. Well I was checking you out, too..." It was true, I had been observing him, but not in the way he'd probably like.

"You know, if you're more comfortable buying right from the source, I get a finders' fee too. They wouldn't sell to just anybody, but I'd be happy to put in a good word," he winked, his pants clearly expanding in his crotch.

"Really? That'd be great, man!" I said, excited, but maybe not for the reason he thinks.

"It's no trouble," he said, smiling as he walked near me and grabbed my butt again. Immediately, I panicked.

"Ohh! I...uhh...could I use your bathroom, first?" I said, thinking quickly.

"Sure man, down the hall on the left." He pulled away reluctantly, but clearly anticipating my return.

I walked into the bathroom, leaning over the counter, looking in the mirror. "Shit," I thought. "I'm not gay. But how the hell do I get out of this and still meet the source?" I wracked my brain for answers. If I pretended I wasn't into him or blew him off, he probably wouldn't get me in with his source, but I wasn't sure if I could handle sex with a guy. I was fine going undercover at a gay club, even flirting with some of the patrons to maintain a cover. But fucking a guy? That seemed too far. Still, I couldn't just bail on the assignment, and at this hour, no way I'd be able to get a hold of my C.O. I flushed the toilet and splashed some water on my face. I didn't have much choice. At the very least, maybe I could try to keep it to foreplay and make as little contact as possible? I'd gotten blowjobs before from girls, and I had to figure getting one from a guy wouldn't be too different. 

I took deep breaths, and went back out, where Blake was sitting on the couch, still wearing his tank top and pants, but now he was rubbing himself through his pants. "Hey there, stud," he greeted me. I sat down on the couch next to him, and he moved towards me, pulling my face towards his. He kissed me deeply, pushing his tongue between our lips, exploring my mouth. His hands ran up my chest, grabbing each of my nipples through my shirt. Before I knew it, he was undoing my belt buckle, unzipping my fly. As soon as my boxers popped open, he pushed them down and grabbed my soft cock.

Blake started jerking me off, slowly at first, but gradually picking up speed as he started playing with my nipples. I moaned as he rubbed my sensitive, muscular pecs. "Ohhhhhh fuck..." I groaned. Then without warning, he dropped to his knees, sucking my cock while keeping eye contact with me the entire time. When I stood up again, he rubbed the tip against his cheek, tasting precum, before moving forward and wrapping his hand around my now-hardening 8-inch long shaft.

Then Blake began sucking me off again, licking and slurping loudly. And although I tried to resist at first, having my hard-on sucked, even by a guy, really turned me on fast. "Fuuuuuck...ohhhh yessss!!" I grunted quietly. Oh god, he felt amazing! Better than the girls who've sucked it. He kept bobbing his head on me, taking every inch in his throat, moaning softly all the while. After a minute or so, I placed my hands on his shoulders, holding him steady, enjoying the feeling of his tight neck muscles flexing beneath my fingers. Soon, I gripped him harder.

"Fuck yeah! Take it man!! SUCK MY DICK!! Fuckkkk..." I was groaning louder now, letting loose with a torrent of obscenities. "Ahhh FUCK!!! UUUUHHHHHHHNNN!!!!!" Blake had taken control, stroking faster and deeper, his tongue lashing my balls aggressively. Suddenly, he threw his head back and screamed into my groin. With one final push, I exploded into his mouth, shooting my load directly into his gullet. Blake continued pumping my dick furiously after it shot, milking me dry. Finally he slowed down, catching his breath; then leaned up and opened wide, showing me cum dribbling down his chin and running from his drool covered lips.

"Your turn," he smiled, standing up.

"Shit," I thought, as he started getting undressed. "I can't suck a dick!" I knew I'd have to if I wanted to meet his supplier, but I wasn't sure I could get past the mental block of having a dick in my mouth.

Blake now stood before me, fully naked. He had a muscular body; big arms and shoulders covered in smooth skin that tapered to a muscular waist, followed by thick thighs and a huge cock. A massive, goddamn cock. I mean damn...that thing must be ten inches long! Holy crap! My eyes bulged when I realized that it was bigger than mine! What the fuck?! Was this REALLY happening to me?? Just being near that monster was intimidating. Even before seeing it erect, it seemed big, but this thing was absolutely enormous!

"THIS is why they call me "Big Daddy," he grinned.

But despite my initial shock, I found myself trying to take Blake's penis into my mouth. Maybe I could fake it until I made it? I leaned forward and grabbed his massive member in my hand, jerking it as if trying to delay the seemingly inevitable. I stroked it gently, noting the feel of such a thick, long specimen pulsating under my touch. I brought the tip toward my reluctant lips. I hesitated briefly, unsure whether or not I should go ahead. Now that I had seen it up close and personal, I had a better idea of how big it actually was, and suddenly I feared choking on it if I attempted to take it in my mouth. but knowing I had to risk it, I swallowed my pride, closed my eyes, and engulfed the head Blake's giant rod in my warm, wet mouth.

"Mmmmmmmmmm Godddd! MMMAAAAAAANNN!!!!!!" He buckled backwards onto his heels, hitting the wall behind him with a thud. "Holy fuck!! Dude!" I remained still, half expecting another round of verbal abuse, but instead he started panting heavily.

Somehow, I guess I hadn't done too badly my first time sucking dick, because he put his dick back in my mouth, and I went back to sucking the hard, leaking tool. He pressed both hands against the wall above my head, continuing to moan softly. "Suck it buddy boy...just like that....fuck...yeah...you like that huhnnn?!" I nodded reflexively, pretending to enjoy this (even though I still couldn't bring myself to like it), unable to speak; I was too busy tonguing his fat, swollen knob. "Yeah baby...suck my fuckin' dick bitch!' he growled, slapping me lightly across my cheek with his meaty hand, eliciting a slight gasp from me. "Damn I love that shit...right there...like that....yeahhhhhh!!" Blake pumped slowly in my mouth, sliding further in each stroke, bumping the back of my throat repeatedly. He grabbed the back of my throat, trying to make me deepthroat the massive boner. I did the best I could, swallowing roughly whenever he hit bottom.

Within seconds, his breathing became ragged, and he lost control completely. "Unnnghhh...fuck! Unnngggg...unhhhhh!!! Ooofffffff!!!" I heard him grunt as he came in my mouth. Rather than spit it out immediately, I held it in my mouth and swirled my tongue around the base of his swollen pole as he finished coming down from his orgasmic high, swallowing everything, since his cock blocked the only other direction.

"Goddamn, man," he said. "That was a good suck. Glad we're not done yet though," he smirked. "Get on your back, legs up."

"Oh shit," I thought. "He's gonna fuck me. How the hell do I get out of this? I can barely take a dick in my mouth, much less my ass." My thoughts raced through my head.

"Hey man, my ass...it's never been fucked before," I told him.

"That's okay baby, I promise I'll take it real easy on you," he said in a calming voice. "You're gonna have to take it, though, 'cause I don't bottom." The irony.

I resigned myself to my fate, knowing I can't get out of this without screwing up my first major detective case. "If it's only one time..." I thought, "I guess I can handle it."

I leaned back, lifting my legs up, exposing my tight, straight, virgin hole to the fucker. Slowly, he started licking and rimming around my tight exit. His tongue brushed up against my hole, sending shivers throughout my body. "God, this feels weird," I mumbled, closing my eyes. I worried about what would happen if he stuck his tongue inside my rectum and got an infection or something. I wondered if I was going to regret doing this later. Would I think differently tomorrow? But once again, Blake appeared to read my mind. "Relax dude, it won't hurt," he reassured me. "Just relax and let things flow naturally." Despite his words, I tensed up anyway as he pushed a finger in.

"Ahhhhhrrrrggghhh! Goddamn...this hurts!!" I gasped, clenching involuntarily. His finger explored inside me, probing the length of my tunnel in search of any resistance. Once he got in there past my anal ring, there wasn't much pain involved per se, but more like discomfort. It was odd to be penetrated by a complete stranger, especially a guy. "It doesn't matter anyways," I rationalized to myself. "This is a one-time thing."

When he thought I could handle it, Blake added a second finger, spreading my cheeks apart for easier access. They both entered easily enough, but I winced nonetheless as they touched inner parts of my body that nobody had explored before. Overwhelmed by the sensation, my brain shut off momentarily, allowing my senses to focus entirely on the sensations coursing through my body. The dual penetration filled me up instantly, making my cock throb painfully.

Blake applied pressure, forcing my hole wider with each thrust of his digits, stretching me to accommodate their intrusion. However, this also helped lubricate the passage from the lube on his fingers, which caused my arousal to return quickly.

"Feel good?" He asked. I didn't answer. And with that, Blake reached over and shoved a third finger up my asshole. "Aaaaaaaahhn!! Ahh gawwwd! Fuuuuckkk!! This is so much!" I cried as he added more lubricant to help ease my passage. I bucked and writhed as the fingers penetrated my hole, making me growl and grunt. Soon, he had four digits buried firmly within me, stretching me beyond belief; it felt so intense! Blake withdrew them one at a time, rubbing the spot where they exited along my taint before replacing his fingers again, pushing steadily deeper into me. As he did, he pulled me closer towards himself until our crotches were touching, causing us to grind together vigorously, stimulating each others cocks simultaneously.

Blake pulled the fingers out, and moved up to make out with me. Focusing on my job, I returned the kiss, before he pulled back. I looked down at Blake kneeling between my spread legs, watching him rub his large cockhead along my tender opening. This was new territory for me, but I figured if I laid there and took it, it would be over soon enough.

Slowly, the dickhead pressed against my tight opening, pushing into my virgin hole. Inch by inch, I felt its thickness penetrate my pucker, and bit by tiny bit, it stretched open some. I let out a loud, vulgar scream. "SHIIIITTTTTT...Holy fucking shit! You are huge! Ahhhggghhh Godfuckingdamn! FUCKING SHIT!!" My hole spasmed as it got split open.

Blake chuckled, grabbing hold of my hips. "We've just gotta get used to one another," he grunted, pushing his shaft through my oily insides. My hole resisted slightly every time he tried penetrating me; however, he persisted, applying steady pressure that eventually worked its way in. Eventually however, I felt it reach full depth inside me. After several minutes of slow, deliberate entry, the rest of his impressive prick slid inside me with effort, filling me to capacity. My anus twitched violently as I accepted all ten inches of Blake's gigantic manhood. After staring intently at me for several moments, Blake began moving upward, fucking his prick in small increments until finally, after many minutes of slow grinding and gentle rocking motions, he slammed home hard. It was painful, but oddly pleasurable as well. He paused for a moment to give me a chance to adjust, and then plunged back inside, breaking me wide open with a single powerful thrust.

Once again, I screamed like a little girl. It was definitely a lot rougher this time. My face contorted in agony, tears forming in my eyes as Blake pounded away at my poor virgin hole. I squirmed wildly beneath him, trying desperately to escape. "Jesus Christ it's so fucking deep! Fuck, I don't know how much more I can take! Gaaaaaaahhh!!!"

However, Blake continued relentlessly, slamming my quivering ass mercilessly, impaling me to his will. My hole gradually adjusted to his size, the pain subsiding somewhat while pleasure built up around it. "Shiiitttt! Shit goddamn fucking hell! FUUUCKING SHITT!!" I screamed, as he continued to slam into me. "OH FUCK!!! FUUUUUUCCCCCKKKKK!!!!" I moaned, as he fucked me harder than ever, forcing a series of louder, deeper screams from my lungs. I groaned loudly as he continued plunging into me, driving me crazy with lustful pleasure. Suddenly, he stopped abruptly, pulling his cock out. I opened my eyes, wondering what was next. Then I saw Blake holding his rock-hard cock, pointing it directly at my gaping asshole. "Here goes," he muttered quietly to himself, taking the plunge. He thrusted more forcefully than before, slamming my prostate with every thrust. My hole began to relax, allowing him to continue ramming into me without resistance. "You're such a dirty little whore," he growled, slamming into me harder. "So tight and wet. I love fucking tight dirty sluts like you."

My hands flew to my stomach, grasping tightly at my muscular torso as he drove his mighty phallus deeply inside me, my screaming echoing throughout the room. With the constant pounding, I grew increasingly sensitive, feeling a familiar burning sensation growing rapidly in my balls, signaling impending climax. I squeezed my thighs tighter together, trapping his monstrous member deep inside me as I prepared myself for release. "FUUUUCK!" I roared in a fit of passion, shooting rope after coil of cum into the air, landing all over my body and my face. "GODDAMN MOTHERFUCKING BITCH! FUCK ME! YEAH!! GODDDAMN!!" I shot load after heavy stream of jizz onto myself, unable to contain myself as waves of ecstasy washed over me.

At last, exhausted from the onslaught, I lay helpless under Blake's relentless assault, drifting in and out of consciousness. When I came to again, Blake was standing upright behind me, pumping furiously at my ass, plowing it ruthlessly. "Take that fucking cock, slut! It's gonna fill you so goddamn good!" he growled. The torrential onslaught of Blake’s cock lasted long after I had emptied myself dry.

His cock pistoned in and out of my hole, throbbing inside me as it generated friction with my prostate, making me feel deliriously aroused as wave upon wave of pure carnal bliss flooded through my body. Cum erupted endlessly from my leaking nut sack, coating Blake's gleaming body as it continued drilling me senseless. "Oh god yes…oh Godddd…yes…fucking YESSSS!" Blake moaned, continuing his incessant barrage.

Eventually, Blake ran out of steam and slowed his pace. Even though he hadn't come inside me, his precum coated my hole generously. He started letting my hole have it again, roughly ramming his cock upwards repeatedly and hammering at me with renewed vigor. "Fuck yeah! Take that big fucking dick bitch," he grated in a throaty voice, humping me ferociously now that he'd regained strength. "Ooowwwwww! Yeah, that's right ya nasty cumslut! squeeze that fuckin' dick! OHHHHHHH MYYYY GAWWWWD! That hole! So tight! Ohhhhhh fuck yeeeeeeees! Yes! Fuckin' GGGGRRRRREEEAAATTTTT!!" 

My hole felt like it might tear open with his rough treatment. Time seemed to stop and the world went dark as he brutally rammed his massive cock into my defenseless rectum. He battered his way into me with abandon, slamming his cock into my hole with enough force to make the couch shake. I was losing control of my senses, and I had no idea how much longer I could hold on. 

"YEAH motherfucker, I'm about to cum deep inside your tight little asshole," he announced proudly. "Give me everything ya got...give me ALLLLL OF IT!!! OH SHIIITTT!!!!! Here it comes!! Unnnnngggghhh!!!!!" As I squeezed his cock, Each forceful thrust brought forth fresh spurts of hot semen from his enormous rod. Finally, he released his pent-up tension, unleashing a torrent of thick seed into my ravaged hole, flooding my guts completely. I felt the warm liquid pouring into my hole. As he unloaded his payload, there were fresh streams of hot semen erupting from his swollen cock, splattering against my skin. At last, my spasmodic contractions weakened, releasing Blake from the clutches of my fresh-fucked hole. A few final strikes sent his entire load of seed spewing deep inside my bowels, saturating my guts and sending my ass into convulsions as my body trembled uncontrollably.

"Fuck yeah!" He shouted triumphantly, pumping a few final spurts of hot white cream into my ass before collapsing atop my writhing form. Blake held still, resting his weight on top of me and running his hand up and down my chest. We remained locked together for several minutes afterwards, basking in post-orgasmic euphoria. We lay there motionless, catching our breaths. Finally, he rolled off me and sat upright on the floor beside the couch. With a satisfied smirk, Blake slapped his thighs and stood up, walking over to the cabinet to grab the bag of weed he was selling me.

I thought about what just happened. My hole was just fucked. This was a big thing to wrap my head around, even as my ass still spasmed and leaked cum, oozing fluid from my splayed sphincter as it slowly relaxed from the abuse. I turned over to look at the mess on the living room carpet. There was an obscene amount of ejaculate covering most surfaces. Several drops fell onto my bare feet, adding to the splatter already present on the ground, leaving a wet trail leading to me.