“Looking spiffy.” Kaitlin smirked and eyed my 6’5”, 225-lb frame.

I did clean up nicely. I had to — it was my childhood friend Josh’s wedding, after all.

The year was 2019 and I was newly single. And I’d had a “thing” for Kaitlin since she, Josh & I were in science class together.

So I had the hair gelled, the suit perfectly fitted (maybe a little snug in the chest and arms)

…and a bit too much cologne.

I raised my eyebrows and nodded nonchalantly. I tend to default to a dry, stoic demeanor, especially around attractive girls. It can be charming — in spurts. And I was “on” tonight.

“Yea — looking SPIFFY, Nick!” Kaitlin’s older brother, Alex, chimed in, and smacked me on the back. Despite being a slender 5’9”, his smack left quite a sting.

Despite the fact that I had been Kaitlin’s friend since early childhood, I’d only had brief interactions with Alex over the years. He was 10 years older (36 now). And, frankly, he was a bit of an ass.

Something about his brash personality didn’t mesh well with my more subdued, dry humor. I don’t think he was a fan of me, either. I recall one time beating him in an arm wrestling match when I was just 17 and he was in his mid 20’s. He didn’t seem to like that… and I’m pretty sure he’s been subtly poking fun of me in every brief interaction we’ve had since.

As Kaitlin, Alex, and I packed into the backseat of the Lyft that was taking us from our hotel to the wedding venue, I realized, to my dismay, that it was about 90 degrees outside. I also realized that Alex was looking rather scruffy and disheveled for the occasion, his black beard and wavy hair already starting to show signs of perspiration. “How did the big boy end up in the middle seat?” Alex grinned and smacked my muscular thigh. I rolled my eyes. Kaitlin repositioned herself so that her leg was making contact with mine. I felt a twinge in my pants.

The wedding was great — albeit a sweatier affair than I’d have preferred. Alex stuck by my side for most of the night, making wisecracks disguised as compliments about my looks, athletic achievements, and Ivy League education. I didn’t mind it much — he’s truly a funny guy. We were having fun. And things were going amazingly with Kaitlin …And I had a few cocktails in me.

It took me about 5 drinks to loosen up enough to hit the dance floor. When Kaitlin and I danced together, I was a bit “stiff,” in more ways than one. She certainly didn’t seem to mind. She even copped a subtle feel once or twice.

By the end of the night (and several more drinks later), my stoic facade had nearly melted away. I was gyrating my hips to Cardi B and Miley Cyrus — much to Kaitlin’s delight.

Alex even joined in and danced with me. At one point he grabbed my arm a bit too hard, and I batted him away with a “fuck off.” Then we went right back to dancing.

When the final song ended, we were all sweaty… and buzzed… and a bit delirious. We gave Josh and his wife a grand send off, and I racked my brain for ways to get some alone time with Kaitlin, given that Alex was staying in our hotel room.

And then… my worst nightmare happened. Kaitlin, who had been giving me overwhelming, boner-inducing signals all night long, got sick all over the dance floor. Her mother, Leslie, witnessed the whole thing (it was hard to miss). And so, before I knew it, Leslie and Alex were helping Kaitlin into Leslie’s van and I was saying goodbye to the three of them. They were driving home to Leslie’s for the night. I’d be all alone in the hotel room.

Fuck.

I called a Lyft and stumbled back to the empty hotel room, still drunk. I (ill advisedly) had two more shots of scotch at the hotel bar. And then… I hopped into a much needed, steamy shower.

Now that I had some privacy, almost immediately, my cock began to perk up. I thought about the ceremony and the fun I’d had. I thought about Kaitlin’s dress. And her high heels.

I also thought about Alex… his douchey comments… and him roughly grabbing my arm.

I was juusst reaching down to touch myself when I heard a door open and close. My heart skipped a beat. Then, suddenly, the bathroom door swung open.

“Hello?”

The intruder muttered something back. And then… he started peeing.

I could tell it was Alex.

“The fuck, dude?”

He chuckled, finished peeing, and flushed the toilet. Instantaneously, the warm water that had previously felt so nice on my genitals turned ice cold.

“Alex, get the fuck out, man. I’m showering.”

He said nothing. Then I heard the sink running. Two seconds later, he chucked a cup full of ice cold water over the shower curtain… and all over my shivering, naked body.

I was furious. I slammed the faucet off and grabbed a small white towel, which I wrapped around myself haphazardly. (Full disclosure: my cock is proportionate to my 6’5”, 225-lb frame. Which is to say that it is not very well obscured by a loincloth sized towel.) I threw open the shower curtain and shoved Alex backwards.

Here’s where things took a turn. It seems crazy to even type this: Alex didn’t attempt to defend himself at all. He didn’t shove me back. And he certainly didn’t leave the bathroom.

Instead, he simply … grabbed my cock. And balls.

Firmly.

Through the towel.

This maneuver cut me off mid-sentence. I may have let out an involuntary noise of some kind.

Now, I don’t know whether to blame this on the alcohol, or the hours-long cocktease that preceded, but … let’s just say the blood that had left my cock when it was splashed with the cold water suddenly came rushing back in full force.

The next few minutes, frankly, are a blur. I am simultaneously aroused and ashamed when I revisit these memories. (My current girlfriend certainly does not know about them.)

I’ll try to recreate the images here as best as I can:

Alex and I never kissed. What I do remember is my towel coming off once again. And Alex’s suit. We ended up back in the shower shortly thereafter…

and this time, I made sure the water was nice and hot.

I remember Alex kneeling in front of me. When he finally saw my cock at full mast (grower here), he changed; there was an almost animalistic look in his eye.

He stared it down, He didn’t put it in his mouth. He just left it throbbing there, a few inches from his face.

I remember him nibbling my inner thighs while I leaned back against the shower wall.

He eventually made his way to my balls, which were clean shaven (for Kaitlin). At this point in the night, they felt fuller than they’d ever been in my life.

At some point, his hands migrated up my soapy, wet torso and he started pinching my nipples, which hurt a bit. I remember letting out a noise resembling a growl. Little fucker. I pushed his hands away, and down toward my now borderline-desperate cock.

He still didn’t touch it.

Instead, he cupped and gently nibbled on my low-hanging, now-aching balls… and then the fucker slapped them. I flinched, embarrassingly.

Even more embarrassingly, Alex’s slap resulted in an involuntarily spurt of precum. Holy shit.

“That’s what I thought,” he said.

I was flabbergasted.

After what seemed like an eternity of teasing, one of Alex’s fingers began to migrate toward my asshole. I don’t know if it was my upbringing, but my immediate reaction was to push it away. (To be honest, I’d never partaken in such activities before — my ex girlfriend was pretty vanilla).

This jolt of nervousness triggered another voice in my brain, which reminded me: “you’ve never done ANYTHING with a dude before — let alone Kaitlin’s brother?! This asshole?! Oh, and by the way, you’re fucking straight!”

I opened up the shower curtain and muttered something incoherent to Alex. And I re-wrapped the tiny white towel around my waist. I dried off.

He seemed both concerned and somewhat amused, and said he was going to get me some bottled water. He left the hotel room.

Alone once again, I walked over to the bed and plopped down, face-first, into the pillow. “What on earth??”

My heart was pounding. I felt a warm rush of either excitement or anxiety. “What the fuck is happening here? I should get up and leave before he gets back.”

But I didn’t leave. In fact, I remained on the bed — get this — still FACE DOWN, with NOTHING covering my BARE ass except for a tiny, haphazardly tied towel.

I don’t think I consciously realized it at the time, but I was presenting myself to him on a silver platter.

(What a fucking thing to say.)

He re-entered the room after about 10 minutes.

"You ok?"

“I, uh, think so... yes.”

He turned the corner and saw the display on the bed.

“Yes, sir” he corrected me.

I didn’t say it back, still trying to maintain some semblance of masculine dignity.

He hopped on the bed and delicately pulled the towel up — revealing my freshly-showered, utterly bare asshole. I suddenly noticed the cool air from the hotel’s air conditioner.

“Pretty and pink” he said. I was soo embarrassed by how much I enjoyed hearing that.

He smacked my left ass cheek. Hard. “What the fuck man,” I said.

“I didn’t tell you to speak.” He smacked the right cheek even harder. Ouch. "I could easily manhandle this little fucker…" I thought to myself.

“Fuck you, Alex.”

But he was winning the battle of wills. In fact, my throbbing cock had re-entered the chat at this point. I felt it inflating against the mattress.

And as that was happening… without warning, Alex firmly spread my ass cheeks apart, revealing his coveted meal for the night.

Before I could even properly react to that, this man, 10 years my senior and about half my size, was diving into my asshole — tongue first.

Here’s where things get a little fragmented again. I remember his tongue feeling like it was merely “rimming” my hole at first… until it finally slipped “in” me — at which point I remember him going “mmm” like he’d just tasted a delicious piece of fruit. I liked that.

I remember how sensitive and ticklish my cleanly shaven balls felt when he lovingly licked and nibbled them from behind — his nose firmly pressed against my asshole the entire time.

I remember him nibbling, biting, and smacking not only my ass, but my shoulders, back, arms, legs, and - I think - even my feet. It was kind of a haze.

What I do recall very clearly is that he still didn’t touch my throbbing cock at this point. That was killing me.

Eventually, the inevitable happened once again. A standoff. His index finger. My tight virgin asshole.

I stopped him once again. For some reason, I couldn’t get past this mental block about getting penetrated.

“What’s wrong, big Nick?”

“Not… yet…” I tried to think of an excuse.

“Ohh… you’re scared of THIS little finger?” He smacked my ass harder than ever before, leaving a bright pink hand mark.

“Dude—fuck.”

At this point, Alex noticed the pool of precum that had accumulated around my throbbing, neglected cock, which was still pressed against the bed.

“Ohh I know what you want…” he said. “C’mon, admit it. You want another man to make you cum. You want ME to make you cum.”

He wasn’t wrong, but for some reason I remained silent. I couldn’t bring myself to say those words. I couldn’t even believe I was having those desires.

Still … I was desperate for a release.

“Say it, young man” he pulled my cheeks apart and took a long, deep lick of my hole.

“Say it.”

Another long, slow lick.

“Just say it, boy, and you’ll get what you want.”

I’m not exactly sure what my body was doing at this point, but if there was video footage, I’m pretty sure it would show me squirming pathetically and making various totally involuntarily noises.

Finally, I couldn’t take it anymore: “I want you to make me cum.”

He wasn’t satisfied. “Call me sir. And say please.”

I hated the trade-off that I was about to make.

“Ugh…. Please make me cum, s— whoa!”

He reached under my body and grabbed my cock and balls for the first time in well over an hour. I shivered.

“Ok, boy. But if I make this big cock cum, I want something in return. Do you know what I want?”

I did. But I was kind of afraid to even acknowledge it.

“I, uh--"

“Tell me.”

“You want my…” I mumbled the rest.

“What’s that boy?”

“You want my … ass.”

“I want your pretty pink asshole. Tell me you’re going to give it to me.”

“..."

“Tell me exactly that. Or I’m not letting you cum. You little bitch.”

This fucking asshole. I weighed my options as my cock thump-thumped to the tune of my elevated heart rate.

“….I’m…. Ugh… I guess … my ass.. I’m going to...”

“You're going to give me what?”

“My pretty pin—-“

In what seemed like one fluid motion, Alex flipped me onto my back, firmly cupped my entire scrotum with one hand like it was his personal plaything, and began to give me — without a doubt — THE most magical, toe-curling oral sex I have ever received.

At first, he only had my swollen head in his mouth.

He looked me directly in the eye. "Mhm," he said. His ego must have been pleased with the look of shock and pleasure on my face.

He gradually worked my cock deeper and deeper into his mouth and ultimately his throat, clearly savoring every inch.

He didn't break eye contact.

I leaned my head back on the pillow, in awe of what was happening. Every muscle in my body was somehow tense and completely relaxed at the same time.

And then...

He slipped his middle finger into my asshole.

"What the fuh---" I exhaled.

Literally mere SECONDS after feeling a finger inside me for the first time …

...Alex's finger...

...no point denying it now…

My eyes rolled back. Abs tensed up. I grabbed the sheets for dear life.

And that's when I unleashed -- at minimum -- 7 spurts of warm semen directly into Alex’s mouth. He did not stop staring me in the eye, and continued to bob up and down at a truly expert-level pace even after I came.

I remember putting my forearm over my face and biting down, hard. It truly felt so good that it almost hurt. My ex girlfriend could never...

Alex slowly removed my shiny, pink cockhead from his mouth. "I know that's what you wanted all along. Was it so hard to admit?"

I laid there, stunned. And once again covered in sweat. When did that happen?

I was drained. And satisfied. Still... there was this little voice in the back of my head, trying to debrief what had just taken place h—

Alex didn’t allow me to finish that thought.

He pushed my legs back. Roughly.

"Let's see what we're really working with here," he said.

He took his thick, veiny cock out of his dress pants.

Fuck...

Before I could think about protesting, he PUSHED his now-rock hard cockhead right up against my exposed asshole.

At this point, it was pretty well lubed. Still — I was SHOCKED... shocked when his cock broke the 26-year-old seal and ACTUALLY went up INSIDE me.

And then it kept going in.

Deeper and deeper.

I felt so full that I wasn't sure if I could move.

“You like that, don't you, boy?”

I winced a little bit. He pushed my legs back some more.

He placed his hand under my chin.

“I asked you a question. Do you like daddy’s fat cock stretching this tiny pink hole?”

Daddy? Come on...

I couldn’t say it.

That's when he grabbed my throat.

I tried to speak: "I—-leerkk—-errrtttt."

He squeezed.

“What’s that, boy?”

“I—lrkkkkk”

I felt a rush of pleasure and lightheadedness. My softened cock began to inflate once again.

(Truth be told, this was the first time I had gotten hard again so quickly after having an orgasm. A few years later I would realize that Alex, of course, had been massaging my prostate with his rock hard, upward-curving cock. )

"Slutty little boy. No pussy for you from here on out. Just my cock."

At this point, something unlocked inside of me. An utterly submissive side that I had never tapped into before.

I arched my back and said something completely incoherent.

Alex’s fucking ego was loving it.

“See my cock disappearing inside this little hole? And look at yours -- leaking for daddy. Why don’t you thank me for giving you so much pleasure, boy?”

He squeezed my throat.

“Thrannk—-youuu”

“Thank you, SIR.”

“Thrannk—you—srrr”. Another sudden rush of pleasure and warmth.

My legs started to shake and muscles twitched. It was like my entire body was in on the fun. That had never, EVER happened with any woman.

Fuck. He had me now.

Alex's stamina was, admittedly, pretty remarkable.

He spent the next 30 minutes stretching my hole from every angle. And making me say progressively more degrading things while he was doing it.

I would never have admitted it for the longest time, but by the end of the night, I gave in, and was calling this man “daddy.”

Finally, he manhandled me back onto my stomach. He proceeded pin me down by my waist... and began to fuck me in the prone position.

A favorite of mine, though I wasn't usually the one being mounted...

He thrusted hard. And even deeper than before. With less focus on my p-spot.

This part was for him. "I’m going to cum inside you. You know what that means? You’re my bitch now.” He growled.

I don't respond. So he spanked my ass, hard.

I know I deserve it.

“You hear me, boy? I’m going to cum deep inside your sweet hole. I stretched you out so nice, didn't I, bitch boy?"

He grabs my hair and pulls my head back so I have no choice but to look at him.

“Yes... sir."

Thrust. thrust. thrust.

Smack.

Thrust. Thrust.

Quite literally fucking pummeling me into the mattress.

And there was no sign that he was planning on finishing anytime soon.

I started to dissociate, picturing myself in the place of the slutty, submissive girls I’d seen on Pornhub over the years. At some point, I realized my cock was at full mast again.

Was I going to spurt again before he even came once?

And then...

Alex started breathing more heavily. This was unlike any sound I’d heard him make up to this point.

At the same time, he squeezed my palm-printed asscheeks -- so tightly I thought he might rip the skin off.

I knew something was coming. But I don't think anything could have fully prepared me for it.

In an instant, I felt a sensation I’d never experienced before in my life:

10 -- no, ELEVEN? -- thick, piping HOT jets of cum. All in unbelievably quick succession.

Deep inside my asshole.

Holy fuck. It was way more cum than I’d managed even after a full night of getting cockteased by Kaitlin.

Upon feeling this brand new sensation, I must have involuntarily kicked my right leg up, because I felt the heel of my right foot kick Alex.

"Sorry..."

(Wow. I'm APOLOGIZING to this fucker after HE just fucked ME in the ass?)

He scratched my shoulders gently with his nails. "Welp. That settles it."

I was trying to think of something clever to say, but the time for that had passed. All I could do at this point was agree with him. I breathed heavily and my cock fluttered.

"Your hole is fucking TIGHT, boy. Or at least it was. I stretched you good. Isn't that right?"

“...yea..."

He looked at me sternly.

"Yes, sir" I corrected myself.

“You’re a gay boy now, aren’t you?”

Shit... Was I? No. I couldn't be.

He spread my ass cheeks and admired his work.

I felt some of his (still piping hot) cum spurt out of me and onto the mattress, and my asshole made a sound that I frankly never thought it would make.

“Whose hole is this?"

“Yours..." I mumbled into the pillow.

He grabs my cock and squeezes hard.

I pick my head up again. "Ah fuck... dude."

He squeezes harder.

"I’m not letting go until I believe it."

"It's... yours"

...

"It's your... asshole... ah, fuck"

He starts lightly caressing my perineum with his thumb while keeping a tight grip on my shaft.

"It's your hole... sir? Sir. It's your pretty... pink--"

I trail off as he continues rubbing the underside of my cock.

"I’m... gay. I'm a bitch? You fucked me... I’m your... gay... bitch... I..."

My cock throbbed. He squeezed harder. What does this fucking guy want from me?

"You fucking railed me, Alex. You did. Look at my asshole dripping all over the bed. That's your cum. I'm your bitch now... you're my Daddy."

He finally releases my cock. A look of smug satisfaction on his face.

"Next time, I’m gonna make you cum all over yourself without even touching this fucking thing. Understand?"

When he said those words, I couldn't help it. Once again, I felt a rush, and my cock began to dribble precum ... or cum... or something...

Alex noticed.

“That's what I thought."