Man to Man

Dustin had been on edge all day. I mean, it was his wedding day after all. We (me, his best man, and the other three groomsmen) were doing all we could to put him at ease. I even outright asked if he was getting cold feet, to which he replied with only a scoff and a dirty look.

The day had gone according to plan so far, as far as I could tell. With the ceremony due to start in an hour and Dustin still acting like someone had just shit in his cereal, I asked the other three if they could give us a bit of privacy so I could quell the storm Dustin was in. We were all good friends, but it was known to everyone that Dustin and I were closest. The mood was dark and it was clear this was our last option, so they eagerly obliged. As Brendan closed the door, he looked at me with a sad smile and said, “good luck.”

 “Ok, dude,” I said turning to Dustin. “What the hell is going on.”

“It’s- It’s nothing,” he replied still bouncing his knee impatiently. “I’ll be fine once the ceremony is over.”

“Are you nervous?” I asked. “It’s ok if you are.”

“No, I’m not nervous,” he said burying his face in his hands.

I was expecting him to say more but he remained silent behind his hands.

After a minute I said, “If you don’t want to do this, its ok, I can help you figure this out.”

Dustin stood up abruptly and shouted, “I love Katie! This isn’t about that! Nothing’s wrong!”

“If you love Katie then act like it!” I yelled even louder. I didn’t intend the outburst, but at this point I was frustrated with the day’s bullshit. And once I started, I couldn’t stop.

“If you’re going to go out there acting like this, you’re going to ruin her god damn wedding! You need to get off this bitch shit and tell me what’s wrong so we can figure it out before you fuck it all up.”

As surprised as I was with myself, Dustin seemed more stunned. At least I had his attention now. I took advantage of his speechless state and followed with, “The next thing you say, is going to be what is bothering you.”

“Look I know you want to-”

“Nooooo,” I droned loudly cutting him off.

He glared at me for a moment and said, “Fine, OK, the problem is I just… I just… wanted to do one last wild thing before I get married. I respect ‘the sanctity of marriage’ and all that shit, so I don’t want to do anything after I actually get married. In an hour.”

“We had a bachelor party in Vegas,” I recalled. We went to that strip club and you had multiple lap dances and everything! What, did you want to fuck a stripper?”

“Well, kinda yeah,” he said flatly.

 “Then why didn’t you?” I asked sarcastically. I wasn’t expecting that answer and was annoyed bordering on furious that this is what his sour mood was about.

“There was no way to do that without everyone there figuring it out,” he explained. “I love Katie, but I just need to get this out of my system. I don’t want it to become some crazy drama. I don’t want my friends to have to keep secrets. Just one and done.”

“Then you should have just fucked a hooker,” I said still bemused.

“Dude, I don’t want to fuck some random whore, that I can catch something from, or could surprise me with blackmail somehow. And I don’t just want to fuck, I want to do something wild, something nasty, something extreme. I meant to do something about this weeks ago, but with all the wedding planning I never got the chance.”

Dustin plopped back into his chair, just as glum as before.

I sighed, “Well we only have an hour, so I’m not sure who you’re gonna fuck now.”

After a moment Dustin asked, “Do you remember what we used to do in high school?”

To put it bluntly, Dustin and I experimented in high school. A lot. Throughout those four years we had to have had at least a hundred sleep overs. And though we didn’t always… experiment, it happened at least sixty percent of the time. It started by watching porn together, then jacking off together. At some point we got bored of that and decided as long as no one found out, it wouldn’t be too gay to touch each other. Which started with, jacking each other off, blowing each other, fingering each other, and eating ass. Making out also somehow started along the way, but I can’t recall when. Needless to say, it was a slippery slope that we tumbled down like an avalanche.

Despite the raging hormones we managed to not fuck each other, as that was somehow ‘too gay’. There were times it was close, very close, but it was the dam that held back coming to terms with the fact that what we were doing was gay as all hell.

We both had girlfriends and we both had sex with girls. Well, I did, I assume Dustin did too. We managed to not let the fooling around make us anything besides friends. I hadn’t done anything with any other guys since Dustin and I left for separate colleges, and we hadn’t done anything since reconnecting after graduation. It was something we left back in each of our parents’ basements, but it did cross my mind just before Dustin asked.

“Yes,” I sighed, trying not to grin, but failing. The insinuation was clear.

Dustin matched my smile but remained in the chair.

“So, you want to fuck me?” I asked dubiously.

He looked away, thought for a moment, and said, “Not exactly…”

“Then what?”

“I want to get fucked. I want you to fuck me. I want… I want you to bareback fuck me, and cum in my ass. And I want to feel it drip out of my asshole when you’re done.”

“Ya wanna run that one by me one more time?” I asked in disbelief.

“Dude, I’m dead serious. I know it sounds fucked up, but I want to do something fucked up,” he admitted.

“You’re getting married, literally married, in like fifty minutes,” I reasoned.

“Yes, and after I kiss the bride, I’m going to be a loving and faithful husband,” he rebuked.

“I mean… It’s just… I don’t know…” I stammered.

“Oh, come on,” he chuckled. “I saw that little fucking grin you just did. I know you want to.”

Now, as I said, I don’t have romantic feelings for Dustin, but he’s always known how to rile me up. He did have about three years of practice at it, so it shouldn’t be a surprise. He was right, even though I honestly hadn’t thought of it until he dangled the offer in front of me, I did want to.

He was a good-looking guy after all, strong features, big build, (not fat just… solid) Kind of ‘thicc’ almost. I didn’t normally go after guys, but with our history and all, there always was something appealing there.

“Well, yeah…” I admitted. “But what if someone hears or comes to the door?”

“Just lock the door,” he suggested. “These rooms are practically soundproof. The wedding planner said so because wedding parties apparently usually just talk shit about each other in here. And just keep most of your clothes on. You can answer it and say I’m still getting ready in the other room.”

“Ok, but like, are you even ready for… that?” I asked.

“Well, Katie and I have done some ass play…” he sheepishly admitted.

“Shocking,” I murmured.

“Oh, fuck off.”

“Yeah, but what about… poop?”

“Dude, I haven’t eaten in like two days. That shouldn’t be a problem.”

“Ok so I’m just gonna go in dry?”

“No,” he exclaimed in an offended tone. “I don’t do that much ass play. There’s lube in my suitcase.”

“Why do I feel like you’ve had this all planned out?” I asked with obvious suspicion.

“Dude, I’ll level with you because you’re my best friend,” he said while putting his hands on my shoulders in some attempt to I assume comfort me. “Something like this had crossed my mind. My first choice was to fist a girl in the vag and ass at the same time, while fucking her twin sister or something. But that may have been overly ambitious. Anyway, I’m sorry I didn’t say something sooner, but I really didn’t know how to bring it up.”

“Do you think most guy friends have these discussions on their wedding days?”

“Oh god, fuck no.”

I let a long breath out of my nose and closed my eyes. Dustin’s hands still on my shoulders. I could feel him staring at me from arm’s length.

“So…?” he whispered.

Without opening my eyes, I said, “I think it goes beyond normal best man duties, but yeah. Let’s do it.”

When I did open them, I saw a big, stupid-ass grin on Dustin’s face.

I locked the door and followed Dustin into the adjoining room that didn’t have a sightline to the suite’s main door.

“So how do you want to do this?” I asked gesturing at the whole room.

“Let’s do it on that couch,” he eagerly suggested. “You know, just like back in high school.”

“Are we going on a trip down memory lane?” I asked in annoyance. “Or are we going to…”

I took a deep breath a sighed defeatedly, “Or are we going to have some nasty-ass sex…”

“Get over yourself,” he scoffed while lowering his pants. “I can already see you’re getting hard.”

I looked down and did see an apparent outline in my pants. It was true the prospect did excite me, but I didn’t want Dustin to know how much. I hadn’t realized how obvious I was.

When I looked back up, I saw that Dustin had somehow removed his pants and underwear while somehow keeping his socks and shoes on. He also still had his suit jacket, shirt, and tie on with the top couple buttons of his shirt still fastened, and didn’t indicate he was taking any of those off either. Fucking with a suit on did seem pretty hot.

When Dustin saw my unimpressed look, he pulled his shirt up a little to reveal his fat dick hanging between his legs in all its ‘glory’. I say fat because he was clearly sporting a chub, but he also did have a pretty thick dick in general. It hadn’t changed too much since high school, but I don’t think I had either. Amongst our experimentation we compared size, and while I was definitely about a half inch longer, Dustin had to be a little thicker.

“You shaved! For me!?” I asked with mock enthusiasm.

“Fuck you, it’s for Katie,” he said.

“Not until, I’m done with it,” I murmured through a smirk.

“Dude!” he yelled.

“Sorry! Sorry!” I laughed moving closer to him.

When I was chest to chest with him, I softly said, “What I meant to say was: Nice dick bro. No homo.”

With that I grabbed him and began gently kneading his cock in my hand.

His reaction was half jump in surprise half moan of pleasure.

After I got him fully erect and changed to a more traditional stroking motion he whispered, “I missed the feeling of your hands on my dick.”

My response was a sudden harsh exhale through my nose and a shove landing Dustin on the aforementioned couch. I would never admit it, but as stupid as his comment was, it really, really excited me.

This fucker really knows how to get me going.

I began to take off my belt when Dustin shouted, “Wait!” and held up his hand defensively like I was going to shoot him in the face.

“What!?” I asked suddenly confused.

Maybe he changed his mind and didn’t want to do this?

“Can you… blow me? Like the way you used to when we were in high school?” he asked sheepishly.

I just smirked. Nope definitely still on this.

“As a wedding present?” he continued through an expectant grin.

I audibly laughed and knelt down in front of him. He scooted to the edge of the seat and spread his legs apart.

I lolled my tongue out of my mouth and lowered my head until it gently touched the tip of Dustin’s head, then I guided down the underside of his shaft letting more of my tongue rub against it as I descended. Soon he was past my lips and I oh-so-gently closed my lips around him. I continued pushing my head down and taking in as much of Dustin as I could, which honestly wasn’t that much since it had been nearly a decade since I last did this.

“Oh, fuck man, that feels so good,” Dustin moaned.

I glanced up to see that he was facing the ceiling with his mouth wide open. I forgot how big Dustin’s dick felt in my mouth, I nearly gagged each time his head got near the back of my throat. For better or worse this caused me to slobber all over the place. I could feel spit drip onto my hand that I was using stroke the base of Dustin’s shaft. Not after long that started dripping onto my other had I been cupping his balls with.

“Fuck this is better than I remembered,” Dustin said suddenly. I laughed slightly, well as much as one could with a dick in his mouth, and moved my hand from his balls to his asshole so that my thumb was pressed against it.

Dustin let out another half-surprised moan.

“I want you in that hole so bad,” he groaned.

I pressed my thumb against his sphincter a little harder feeling it give just slightly to the pressure. He was tighter than I remembered, but I hadn’t done anal in over a year so, that probably lent to my surprise.

“You wanna fuck that ass?” he half asked half growled.

Now I remembered why we had started making out as part of our experimentation. Dustin liked to talk during sex, or at least during ‘fooling around’. Where it was appreciated and sometimes exciting, it was often just a narration of what was occurring in the moment and sometimes really cringeworthy. Making out obviously kept his mouth busy when I was rubbing our dicks together in my parent’s basement, or knuckles deep into fingering him.

Another fun fact about Dustin that had just recently been brought to my attention was that he pre-came. A lot. The tell-tale taste had grown stronger in my mouth and was definitely contributing to the slobbering.

“Dude, this is-”

Before Dustin had the opportunity to again tell me how either good this was or how much he wanted it I jerked my head back with a little more flourish then necessary, letting the mix of spittle and pre cum spray onto his lap.

“Ah, sorry,” I fake choked. “Haven’t done that in a while and I didn’t want to gag too much.”

Now that I was face to cock with Dustin I saw that he was actually larger than I remembered, and was surprised I had been able to do as much with my mouth as I had. When I started, he only had a semi but now he was sporting a throbbing python of a dick. He had to be at least 7 inches, maybe 8.

Had he… grown since we last fooled around? Had I? I’m pretty sure I did, but I haven’t measured since college and it isn’t really an exact science. Is he bigger than me now? Maybe it was because he shaved his pubes. I may have to check that later…

Looking back, I liked Dustin’s dick enough to do all that I did to it, but it was never really the driving force for me to fool around with him. Now for some reason, seeing his pulsing member just over a foot from my face was causing my body to replicate the sight in my own pants.

“That was amazing,” he moaned. “I didn’t realize how much I missed those high school days. I mean Katie is great, don’t get me wrong, but I think a guy just knows exactly what to do.”

I rolled my eyes as I stood up. Dustin didn’t make any moves as to what would come next so after wiping my mouth with the back of my hand, I plopped myself down on the couch next to him and slyly asked, “Maybe you can uh… pay back the favor?”

That somehow seemed to go over his head, so I abruptly spread my knees apart replicating the position he was just in. Dustin replied with an almost too conspiratory smile and kneeled in front of me. I still had my pants on completely, and it appeared Dustin was waiting for me to take them off. Instead of obliging, I said, “I’m waiting.”

“You’re such a dick,” he shot back while beginning to undo my belt.

 “Yeah, and you’re about to get a mouthful of it.”

 “Why did I even want to do this you?” he laughed while pulling my pants down to my ankles.

I was wearing black calvin klein briefs because for some reason I felt that I needed nice underwear if I am going to dress formally. They looked great on me but did nothing to hide my recently acquired boner. Not too important, but I remembered I looked really good and had to mention it.

“Wow man, I didn’t realize you liked sucking dick so much,” Dustin said nodding at the enormous lump in my underwear.

I just laughed while undoing the buttons on my shirt; I had no clever response. Blowing Dustin had excited me in a way I hadn’t felt in a long time.  

“Oh, please,” I scoffed after a moment. “We both had boners the whole time when we fucked around in high school no matter what we were doing.”

“Yeah, the good old days,” Dustin sighed. “When I would bang Hayley Bowman in the back of my car in the school parking lot on a Friday, and then deepthroat my best bud in my basement on a Saturday.”

We laughed again as Dustin slowly pulled my underwear to my knees, causing my cock to get pulled down too before flipping back up towards me and hitting my stomach.

“Fuck man, I don’t remember you being this big,” Dustin beamed as he wrapped his fingers around my shaft.

Ok good, I’m bigger than he remembers too.

Partially ignoring the amazing feeling of Dustin’s hand gripping my throbbing dick, I put a hand over my eyes and admitted, “Dude, I thought the same thing when I was blowing you, what the fuck?”

“Guess we’re big boys now,” Dustin said before burying his face in my lap. I was shocked by how quickly he took the whole thing in his mouth. I shouted in a mix of surprise and pleasure. Dustin responded with a gagging choking sound.

Unsurprised, I expected him to abandon the task, but after only a slight pause he began rhythmically forcing his mouth down to the base of my shaft. What he lacked in grace, he made up for in enthusiasm. He vigorously bobbed up and down in my lap his lips touching down to the base of my shaft on each descent. He was gagging every few seconds, but seemed to be rolling with it.

I almost felt bad for my lack luster performance, but then I noticed through the gap between my thigh and his head, that Dustin was still dawning a massive erection which he was slowly stroking. I hadn’t had someone quite literally choke on my cock in a long time. The reckless abandon he was exacting to force my dick down his throat was something I had only seen in the dirtiest of pornos. In contrast to the scrape of his slight facial hair on my thighs, his mouth and throat were warm and soft in a way I wouldn’t have guessed they were.

It didn’t take long before I could feel the starting pangs of climax. I imagined grabbing the back of Dustin’s head and forcing it down as I blew a huge load all over the back of his throat, listening to him choke but holding his head in place until he was forced to swallow my cum. That thought got me even closer and realizing that this encounter was supposed to end in me cumming in his ass, I put my hand on his shoulder and pushed him back slightly.

Understanding the signal Dustin withdrew his head letting strands of spit link my dick to his mouth before eventually snapping.

“That good, eh?” he asked before starting to gently run the tip of his tongue up my shaft while maintaining eye contact with me.

I didn’t realize how hard I was panting and how sweaty I had gotten. In the moment I couldn’t formulate a response and just stared into Dustin’s eyes as he traced the tip of his tongue over my dick. He chuckled as he got back up. After checking his watch, he threw himself onto the couch, he turned his body so his head was positioned on the armrest and his exposed groin was pointing towards me. I only stared at his dick as I regained my breathe and came down from my near climax.

In absence of my action Dustin pulled his knees up to his chest, further revealing his asshole, and casually said, “We haven’t got all day bro.”  

“I almost busted in your mouth dude,” I explained as I turned toward him.

“That would have been pretty fucking hot,” he admitted. “But you have to save that for my man pussy.”

He laughed as I rolled my eyes for the hundredth time. To follow up his words he grabbed at his hole pulling at his right ass cheek showing even more of his slightly stretched pink hole.

I didn’t know exactly what he wanted me to do next, but I knew what I wanted to do. I grabbed both his ankles and pushed them back forcing his ass higher up, pulling at his tight little asshole. After shooting him a dirty look I lowered my head letting my breath blow onto his stretched sphincter and balls. I slowly traced around his hole with the tip of my tongue gently, drawing nearer and nearer until it was directly over it. Once there I applied just a tiny bit more pressure and began curling my tongue up and down in a sort of ‘come hither’ motion.

“Oh dude, I forgot how amazing you are at eating ass,” Dustin moaned.

Not sure if I should really take that as a compliment, and with my tongue a little preoccupied, I simply responded by forcing my tongue as far as I could into Dustin’s asshole. Dustin let out a moan so loud that he quickly slapped his hand over his mouth to suppress the noise.

I had to agree with Dustin, I always prided myself on my cunnilingus skills. This wasn’t exactly the same thing, but my expertise had started from numerous times eating his ass out in high school. Call it, going back to my roots.

If I had to say, my skill came from the passion I had for my craft. I have always loved eating ass and pussy. This desire had only been further compounded both in youth and in the present by the fact that Dustin had an amazing ass. In high school I figured I liked it so much because it was the closest thing in common to girls. But, as I mentioned, Dustin had a pretty solid build which culminated in him having a rather large round butt. I can’t emphasize enough that he definitely wasn’t fat. I supposed the best way to describe him would be ‘dummy thicc’.

I pressed my tongue as deep as I could into Dustin, letting as much spit as I could drip over his hole. I periodically withdrew to again gently run my tongue up and down the crack of his ass only to again bury it as deep as I could in his tight hole.

“Oh yeah, I love you tongue fucking me,” Dustin groaned.

Ok I’ll let that one go, because I am doing a damn good job.

“Yeah, get it really wet so you can slide your huge dick in me.”

That one was actually kind of hot somehow.

“You’re making my man pussy feel really good.”

Alright, I’m drawing the line there. I can’t let ‘man pussy’ become a thing.

I pulled my head back and stood up (well kneeled up because I was still on the couch). I stared down at Dustin who met my eyes with a blissful smile.

I thought hard if what I wanted to do next was a good idea. When we started, I told myself we wouldn’t. It was too intimate; it blurred that line between fucking to feel good and catching feelings.

Aww fuck it. He’s my best friend. And look at that stupid little sexy smile on his face.

In what probably wasn’t a very graceful motion I crawled on top Dustin and pressed my lips onto his. He responded by wrapping both his arms and legs around me pulling me in closer to him. I slid my tongue past his lips feeling his twist around mine. We made out before, mostly in my effort to keep him from talking, but this felt a little different. I felt his broad chest heaving against mine. I wrapped my left arm around his back an grabbed his hair. He tightened his grip around me, his muscles apparent through his sleeves. Our exposed crotches pressed against each other, my dick grinding into his stomach and his into mine. His legs were still in the air and I positioned my body so the fronts of my thighs were pressed against the backs of his. We continued twirling our tongues around in each other’s mostly open mouths.

Using my knees for leverage, I raised my lower half slightly off of him to create enough room to fit my right hand between us to grasp both of our dicks so that their undersides fully rubbed against one another.

Dustin let out a slight groan muffled by my own mouth. I slowly stroked, thrusting myself slightly into him rhythmically. The feeling of a dick against mine, and my balls draped over another pair was something I hadn’t experienced in a long time.

I pulled lips away from Dustin’s and held myself over him enough so I could look down at our comingled genitals. It was impossible to tell if either of us was bigger, but the site pulled me back to those days when we were teenagers fumbling around with each other’s bodies, harder than anything else had up to this point. It was obvious Dustin had lifted his head to look too. There was something so satisfying about seeing us pressed together like that mutually experiencing the same pleasure.

Knowing I still had a greater duty than this, I released my grip and backed off of Dustin. The room was filled with the sound of us panting.

We stared at each other for a moment me kneeling over him, both of us naked from the waist down. We both knew what was coming next. And as much as I wanted it, I had to ask:

“You sure you want to do this?”

“Jason, there’s nothing more I want right now, than for you to fuck me,” he replied. He had somehow grabbed the lube he mentioned earlier and casually held it out to me like he was offering me a beer.

I probably had a stupider, goofier grin than he did when I took it. I squeezed some of the liquid onto my fingers and placed the tips of my middle and ring finger against Dustin’s hole. I rubbed around its small circumference for a moment, eliciting a low hum from Dustin. Gently I pushed my fingers into him. I managed the depth my tongue had delved to with mild resistance. Dustin hummed in a continuous soft moan. I massaged the shallow part of him slowly pressing my finger tips against his prostate.

“Aw, fuck man. That feels amazing,” he purred.

That was the easy part, there was that ‘transition zone’ that I needed to press through to really prepare him for what was to come. While pressing the meat of my hand against the space below his balls, I pushed my fingers deeper into him. It took a bit more effort than I hoped and I thought it would give Dustin reason to consider, but his dick was as hard as ever and even though his eyes were closed, he still had that blissful grin plastered across his face.

I pressed in deeper feeling his hole take in my fingers past the knuckle until I had a firm grip on his underside.

“You’re really tight,” I said, trying to express some trepidation.

This was obviously missed by Dustin when he responded, “You want that tight little hole?”

I began massaging Dustin from the inside pressing my fingers against his prostate, slowly pulling out and gently reinserting.

“I really do,” I admitted in a whisper, like there was someone in the room I didn’t want to hear.

However, the only other person there who could hear it, had. Dustin responded by opening his eyes and looking directly at me.

“Please,” Dustin begged in a whisper that matched mine. “Fuck me, Jason.”

I withdrew my fingers from Dustin and applied an ample amount of lube to my throbbing dick. I couldn’t remember the last time I was this hard. Fuck, what does that mean?

After tossing the bottle of lube to the floor, I repositioned myself closer to Dustin. Close enough that I had to lean back slightly to just gently touch the surface of Dustin’s hole. I glanced up one more time, there was no going back after this. Dustin responded with an almost imperceptible nod.

With that confirmation I began leaning into him, guiding my cock with my hand. I saw my head sink into him only slightly and realized it was going to take a bit more pressure to really penetrate him. I slowly leaned my hips forward feeling a growing resistance. Dustin released a breath I didn’t realize he had been holding and I suddenly sank deeper into him. He followed with a slight groan that I couldn’t confirm to be good or bad. I lifted my head up with a sheepish expression but was only met with Dustin’s now signature closed-eye grin. Ok, hard parts over.

He was incredibly tight, not shocking since he hadn’t taken a dick before, but the sensation was unlike anything I had felt in a long time. I savored the feeling of his insides while I slowly pushed inch after inch of my dick into him. His internal grip was so tight I expected him to cry out at any moment, but he continued in a low moan the entire time. With only a couple inches left to bury I hand walked overtop of Dustin so that we were face to face. When he felt the front of my legs touch his, and my balls touch his ass, he opened his eyes.

“That good, eh?” he chuckled slightly.

I realized now the entire time my mouth was open and my face frozen in an expression of ecstasy. After closing my mouth, I chuckled back, “Yeah, you feel really good, really tight.”

“You feel huge,” he said with a slight wince. “Didn’t know taking a dick would be… so much.”

“Do you want to keep going?” I asked.

He nodded and grabbed my sides just below my armpits. Dustin raised and lowered himself a bit just ever so slightly coming off and back onto my dick.

“You’re going to have to go slow to start,” he concluded. “I’m not used to anything as big as you in there, but it feels really good having you inside of me.”

“Good. It feels amazing being inside of you,” I replied awkwardly. I was definitely no better than Dustin at dirty talk.

Now that we were in new territory, I felt just like I did over ten years ago, an awkward teenager fumbling around with mine and my best friend’s bodies. Unsure what to say or what to do. There was that thrill of doing something new, something I shouldn’t be doing. What made it better now though was that I did actually have experience fucking, though not with another guy.

I slowly leaned back and then gently pressed my hips into Dustin. We hadn’t broken eye contact since I leaned over Dustin and as I started fucking him, he stared deeply into me with his mouth frozen in a silent moan.

He was so tight that even the slight thrusts were extremely stimulating. It took more restraint than I could have imagined to maintain a gentle pace. As incrementally as I could manage, I began pulling out farther and thrusting more of my self into Dustin.

With each thrust I could feel Dustin relax a bit, his muscles unclenched and he began grinding into me in rhythm with my thrusts. His grunts twisted into moans of pleasure. And most noticeably his throbbing boner was pulsing against my stomach. I could feel the slight stickiness of his pre-cum on my skin.

My breathing grew heavier and heavier, my jaw clenched, as I grew more a more familiar with the soft warm inside of my best friend’s hole. The sound of my thighs clapping against Dustin’s ass cheeks.

By now, ramming my dick as hard and deep as I could into Dustin, his moans had coalesced into a continuous groan of pleasure, head tilted back. I kept grunting through gritted teeth until Dustin looked down at me and with a knowing tone said, “You don’t have to be so quiet, just let it out.”

He knew me too well, with my next thrust I practically screamed with ecstasy, the release of pressure from my chest and gut paired with the embrace of Dustin’s hole around my cock was almost too much. It couldn’t have been more than five minutes but I was about to go over the edge.

“Yeah, that’s right,” he chuckled smugly.

“No dude,” I panted, slowing slightly. “I think I’m gonna cum.”

Dustin’s grin grew.

“Yeah, fill me with your cum. I want to feel you blow your load in my asshole.”

“Dude, come on,” I pleaded. I was torn between a deep desire to climax and a yearning to continue fucking.

Dustin began grinding against me hard pressing his engorged cock between our abs.

“Jason, I really want your cum inside of me. I want you to impregnate my hole.”

It was probably the stupidest thing Dustin had ever said in one of our sexual encounters, but it was also what put me over the edge. I cried out, and couldn’t stop screaming. Like a damn bursting I could feel load after load gush out of me and into my best friend’s asshole. It just kept coming, burst after burst. I could feel my balls contracting with each release. My legs began shaking uncontrollably and I actually saw stars in my vision. I’m pretty sure Dustin said something else dumb, but the ringing in my ears and sound of my own wail drowned it out.

When I finally came back down to earth I realized my body was heaving with my breaths, it was as if I had just run a marathon. I looked down at Dustin, not knowing what to say or do.

“I guess we should have done this sooner?” he suggested through equally ragged breaths.

“Jesus fucking Christ dude,” I panted. “I thought I was going to have a stroke when I came.”

“You looked like you were having a stroke.”

“Fuck you.”

“Nah, you looked great. You’re a natural.”

“Learned half of it from you,” I admitted.

“Was it too much?” I asked after a pause.

“At first it was a little tough,” he confessed. “I’m not used to… getting pounded. But feeling your cock in me, even if it was a lot. It just was amazing.”

“I don’t think I’ve ever cum that hard before.”

“I’ll take that as a compliment.”

“You were pretty amazing too,” I sighed. “You should consider switching to this all the time.”

“Ok, let’s not get too carried away,” he said indignantly.

“Do you feel better now? Was that what you needed?”

“Uh… yeah,” he half stuttered.

I looked down and saw his still engorged dick pulsing between us.

“You want to cum too?” I half asked half stated, not taking my eyes off his throbbing member.

“Well, it was more about you cumming inside me,” Dustin explained. “But honestly, I started getting pretty close during, that prostate stimulation is serious stuff. I’m still hard as a rock.”

After Dustin said that, I got this weird proud feeling. His fat throbbing dick that was still leaking precum onto Dustin’s chest was so excited because of me. Without exactly realizing what was happening at first, I could feel Dustin’s asshole tightening around me. I looked up expecting a devilish look, giving away some secret plan of his, but Dustin’s face was as innocent as I’d ever seen it.

I realized I was getting hard again. My swelling cock was pressing against Dustin’s insides. His brow furrowed as he took in my confused expression. But at some point, he must’ve felt what was occurring inside of him, and the devilish look I expected spread across his face.

As if we were already standing in the middle of his wedding reception, Dustin whispered, “Are you getting hard again.”

There wasn’t a trace of smugness in his voice, he sounded legitimately hopefully that I was reinvigorated.

I began to slowly pull out and press myself back in.

Before Dustin could say anything, I promised, “I’ll make you cum this time.”

He responded with a mixture between a laugh and a moan.

I pressed my body into Dustin’s sandwiching his cock in between us. Watching the skin on his shaft pull back as I pulled out and get pushed back up as I pressed in. By changing the angle and pressure of my body against his in accordance with the intensity of his moans I could tell I was really stimulating his cock.

The first nut was easy, but now I felt like I needed to really fuck Dustin if I was going to get another load off. Leaning back off his dick, I positioned myself so that I could pull myself out of Dustin to the point where the head of my cock was almost exposed and then really sink it in savoring every inch of penetration.

My plan was to alternate between pressing my body against his dick and lean back for these long thrusts, but as I reburied my cock in him, Dustin cried out, “Oh fuck, dude. Yeah, yeah, like that, I want to feel every inch of you.

I grabbed Dustin’s ankles and held his legs up to make it easier to pull mostly out and reinsert myself. I started slowly, trying not to accidentally pop out. After a few thrust I gauged how far I could go, and began increasing the speed and vigor of my pounding. As I pushed myself into him, so hard my balls slapped against his back, Dustin yelled again, “Yeah that’s it, that’s it. Right there, fuck me like that. Fuck me like I’m your little whore.”

In my mind I hadn’t been that on the nose about it, but Dustin had pretty accurately verbalized my intentions. I fucked harder than I had before, really trying to punish his hole. I started grunting with each plunge. I was hell bent on making Dustin realize the full extent of my cock.

He suddenly looked down at me, with an expression of agony stitched across his face with a thread of pleasure. I met his gaze. I didn’t feel awkward anymore, I felt powerful. Exerting myself over and into my best friend, my manhood thrusting deep inside of him, fucking him like a dirty slut.

This level of enthusiasm must have really sparked a flame of passion between us, because Dustin suddenly blurted out, “Fuck dude, I think I love you.”

I understood and reciprocated the sentiment, but now was not the time for it, and that was not a road I wanted to go down today, if ever.

So, I just responded with a gruff, “Shut up Dustin, don’t make this any gayer than it already is.”

He reared his head back and cackled.

His words may have had more of an effect on me than I first thought because I began to feel the load building inside of me. I could tell by the way he was groaning that Dustin had to be closer now than he was last time, which must have meant he was nearing the peak.

I leaned back down over him our bodies now pressed together, my cock deep inside of him.

“Oh, yeah, right there, I think, I think I’m gonna cum,” he cried.

My eyes darted down, I wanted to see this load I was about to fuck out of him. Dustin’s moans grew louder and louder until they broke in a way that revealed he was past the point of no return.

At first, it looked like he was just leaking precum at a slightly greater volume but then the fluid escaping him turned white and cloudy. With a pulse of his cock a spurt of his thick cum was cast nearly to his nipple. Followed by another that was so large and violent it struck my chin. Between each violent burst cum was gushing out the tip of his dick onto his stomach, so much so it cascaded over and down both his sides.

I could tell he was still going but after watching his physical display of his pleasure I had also hit my bursting point. Like before, I felt surge after surge pass through my dick into Dustin’s asshole. Load after load shooting out of me and deep inside of him. I reveled in the thought of breeding him and imaging how much cum I had deposited inside of him.

For a while we both sat there grunting and cumming, me punctuating each release from my cock with a thrust into Dustin.

When I finally looked down, I saw that Dustin was completely covered in a glaze of cum.

 “Fuck dude… when was… the last time… you got off?” I asked between breaths.

“About… a week ago?” Dustin estimated.

“Yeah, it shows,” I laughed.

“Fuck man, I didn’t think I could cum from getting fucked like that.”

“I didn’t think I would bust a nut twice in my best friend an hour before his wedding.”

“I guess we learned a little something about ourselves today.”

“You… still want to get married… to Katie, right?” I asked with some hesitation.

“Oh yeah definitely,” he affirmed. “I mean, I do love you, like that, but it would never work out.”

“Yeah…” I sighed. “Me too.”

After a pause I asked, “Are you ready?” While motioning at my dick.

“Yeah,” he said. “Here, let’s turn a bit so I don’t get any on this couch.”

We rotated so that Dustin’s lower half was hanging off the seat with me still inside of him.

“Ready?” I asked again

“Yeah.”

I slowly pulled myself out of Dustin finally uncoupling from him, dick soaked and still half-hard.

“Ready to ‘feel the cum drip out of you’”? I asked, parroting his earlier request.

Dustin laughed and I picked my phone up off the floor and pointed the camera at him.

“What the fuck are you doing?” he half barked half laughed.

“You’re gonna want to see this after the fact,” I responded.

Dustin definitely knew me too well, but I also knew him better than anyone else.

“Yeah…” he admitted sheepishly.

With his legs still in the air and ass hanging over the hardwood floor I could see Dustin’s hole unclench, trying to push its contents out.

At first it was a small dribble of cloudy fluid, but quickly became a continuous thin pour that puddled on the floor.

Dustin let out another groan of satisfaction. His battered hole clenching and unclenching as he expelled my fluids from his body. The stream reduced to a dribble and then stopped, leaving Dustin’s expanding and contracting hole.

After it was clear that both of my loads had left him and were now in a large puddle on the floor, Dustin stood up and said, “Well I guess we better get dressed again.”

He checked his watch and added, “We only have like ten minutes until I need to get out there.”

“Cutting it a little close,” I noted, while pulling my pants back on.

“Yeah, we good though.” He replied wiping the cum off himself with a hand towel. “Hey, thanks again for helping me out.”

“Yeah anytime,” I said with mock cheeriness.

“Except, maybe not anytime, since I’m about to get married.”

“Oh right… That…” I said rolling my eyes jokingly.

In ten minutes time, we were both standing at the front of the church. That time was filled with figuring out how to get the cum out of Dustin’s shirt but, giving up when we realized it would be covered by his suit jacket. Then watching the video of his cream pie scene about a dozen times. And finally dashing to the wedding chapel with less than a minute to spare.

Luckily, now, Dustin was hand in hand with Katie while I looked on with the rest of the groomsmen. I’d never seen him happier. Well, except for maybe one exception.

“Hey man,” Brendan whispered. “I don’t know what you said to him back there, but you really saved the day.”

“Ah, you know,” I replied with a wry smile. “Just needed a little man to man.”