Confessions of a faggot hole

CHAPTER 1: “Junior” – It all starts with the Captain --- It’s the summer of 1990 and Rickie (18) wants to take his jerk off sessions with his best friend Junior (18) to the next level. So, taking his cues from "the Captain", the next time the boys are alone and watching porn, Rickie surprises Junior with his fledgling faggot hole.

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The following is a work of erotic fiction depicting graphic sexual scenes and is meant to be enjoyed by a mature, faggot hole loving, audience.


“Junior” – It all starts with the Captain

It’s 1990.

Tim Berners-Lee publishes his formal proposal for the “World Wide Web” that November. It outlined a plan for a system that would use hypertext, web pages, browsers, and web servers to share documents across the internet.

President George Bush and Soviet leader Mikhail Gorbachev sign a historic agreement to end production of chemical weapons.

Microsoft Releases Windows 3.0 and depletion of the Ozone Layer is newly discovered above the North Pole.

America’s favorite animated family The Simpsons is aired on Fox for the first time and Twin Peaks premieres on ABC.

I went to the movie theatre most weekends with my best friend Junior (his real name was Louie named after his dad) to see the latest films like Ghost, Dances with Wolves and Edward Scissor Hands.

I’ve just turned 18 years old and going to start grade 11 in September. Although I’m technically older than most in my year, I’m still physically a bit shorter and not as far along in my development. I’m still 5’6” and although I’m athletic, I still haven’t hit my growth spurt. Yet.

Ever since I was a kid, I knew I was different than most other boys.

I remember boys at school would call me a “fag” or say that I was “gay,” long before I ever knew what that really meant. I just figured it was because I didn’t like the same things that boys were supposed to like.

Unlike most of the Italian soccer and hockey playing boys in my community, I’m a trained competitive dancer who drives across the Canadian border from southern Ontario 4 times a week to study Jazz, Tap and Ballet at a prominent competition dance studio in western New York. I was the only boy in a dance class filled with 15 to 22 tiny ballerinas that I would take turns spinning, lifting and on occasion, throwing up in the air and catching.

This year, most of our competition numbers are choreographed to the Dick Tracey soundtrack, including my lyrical competition solo to Madonna’s “Sooner or Later.”

 “… and in the Senior Advanced solo category, we have Rickie… dancing a lyrical number to “Sooner or Later.” Cue Music.

I start the number in a trench coat and a fedora hat and after a slinky opening I remove the accoutres so I could (as butch as I can muster) point my toes as I jumped and spin freely. See, there are few boys who “dance,” and it’s pretty much me against 17 other senior-level female jazz, acro and ballerina soloists.

I love this routine. I’m Madonna’s private ‘Dick’. I’m her man. The one she always gets. I am always so proud when the competition judges’ comment about how strong and grounded I move, how “masculine” and “commanding” my performance is… in my tights and ballet shoes. Fuck those dumb hockey players.

Training 4 days a week means I have shapely legs, firm round ass cheeks and a slim, but athletic build. And I know it. Although, at the same time, I also know that I do not look like the black and white shirtless (and manly) Mikhail Baryshnikov poster I have hanging in my bedroom. Mikhail is so beautiful executing a huge renversé jump. In the picture his head is flung back and his sweaty hair is flying next to his knee elevated straight beside his ear, with his pointed legs extended as he is suspended in the air. Every black and white abdominal muscle is defined with shadow.

I love this poster. I stare at this poster doing sit-ups on my bedroom floor every night before crawling into bed.

Junior is your more typical grade 11 ‘smoke hole’ punk rocker that lived in his jeans and assortment of various black heavy metal band T-shirts. He doesn’t get the best grades or play any sports really, but he’s a drummer trying to start a band, and because we grew up together didn’t care that I danced. He loves Quiet Riot, Poison and mostly Guns N Roses. He also is naturally fit and has matured rather quickly this summer, shooting many inches taller than me seemingly over night, with big lips and short buzzed hair.

When we were younger, he would sneak one or two of his dad’s cigarettes and then we would ride our BMX bikes to the new subdivision they were building and smoke them in the partly constructed houses as we chased each other through the partially built rooms. 

Our parents are best friends and are in a bowling league together. On Tuesday nights, when our parents are bowling, Junior’s older teenage sister, Lisa, would normally go out with her friends and as soon as she left us alone in the house, we would watch his dad’s porno movies (on Beta, not even VHS!).

One of the porn movies is the classic Debbie Does Dallas, about high school girls that try to “creatively” raise money (fucking guys for cash) so they can travel with the football team. (Don’t worry… Mr. Greenfield, the sports equipment store owner, comes through and pays for their entire trip after Debbie fucks him in her cheerleader uniform in his store.)

My favourite porn though is one that we called The Captain, although I don’t think that is the actual title. The title character, The Captain, is a busty blonde that captains a Love Boat type passenger ship run by a busty female crew that gets fucked and filled by a group of big-dicked horny pirates that take over the ship.

In one scene 3 guys fuck the hot female kitchen staff. In another scene two guys make a husband watch them take turns covering the guy’s wife with their loads. And in the final climactic scene on the tape, all the men join their leader on the bridge where they dstake turns using, abusing and filling every hole of our busty blonde Captain… three or more at a time.

I love seeing the Captain suck the lead Pirate. He is a tall furry muscle man with a Tom Selleck mustache and the biggest, fattest dick. But when all of his men join in, I can feel my heart race when she ends up eventually on her knees SO enthusiastically jerking and sucking each of their dicks… moving quickly from one cock to another, not able to satiate herself. So, many cocks!

And then they take turns fucking her. A lot.

My asshole twitched the first time I saw the tall Skinny Pirate hold his long thinner dick by the Captain’s asshole when she was jumping up and down on leader-Tom-Selleck’s fat cock. The camera jumps closer to her holes, and after a few thrusts of Tom Selleck’s juicy dick filling her pussy, the head of Skinny’s longer cock disappears into her ass.

I love that final scene. Junior knows I love it, too.

Our porn watching sessions always progress to Junior whipping his dick out so I could fuck it with my throat. Every Tuesday night when we’re alone, Junior slips one of his dad’s tapes into the Beta machine to get us going.

When the tape is The Captain, he would almost always have it already queued to the final gang fuck scene where they take turns fucking her in all her holes because he knows the Captain’s eagerness rubs off on me and I will suck him a little more enthusiastically.

But what I really want, is for Junior to fuck me in my ass just like how the pirate gang fucks the Captain in her ass.

If she can take it up the ass, so could I.

So, at home I started playing with my hole in the shower. Slipping in a soaped finger. Then two. Then, I started experimenting with different lubricants, like Vaseline and Margarine. I don’t really like the Margarine. I smell like Thanksgiving.

In my self exploring and playing, I’ve learned that it’s best to make sure I have a bowel movement first, because I would really get up in there, in the shower and/or on the bidet and loosen my hole up so it was best to make sure I was empty. And I got really good at it, especially freshening up after a deep clean the next day in the bidet (we were Italians, all Italians had a bidet in their upstairs bathroom).

I tried to practice using Vaseline and various items… the end of a brush, a beauty product tube or bottle, and a few fat Christmas candles. I even tried a beer bottle once, but when I thought of it breaking in my ass and me having to go to the emergency room and explain why I had broken glass up my ass – I never stuck anything glass in my hole again.

But one summer bowling Tuesday, I was ready.

I prepped myself before I went to Junior’s place.

Before I left to go to his house, I shoved my favourite brush handle up my hole and made sure I was good to take Junior’s cock. It was about the right size, so I knew I was good. Then I took a shower and soaped my insides, sticking as many fingers as deep as I could.

For tonight’s porn, Junior selected an older 70’s video, that was grainier and had more bellbottoms. In this one, a Mafia Boss accuses his little petite wife of having an affair with her tennis coach and demands that she fuck the Tennis Pro right there in front of him and his two bodyguards. The dude must comply or get beat up by his guards so the three of them watch as Tennis Pro fucks her.

On screen Mafia Boss is sitting behind a desk while Bodyguard 1 stands behind him with his arms crossed.

Bodyguard 2 has Tennis Pro by the arm, while Cheating Wife, in her little tennis outfit is on her knees with Tennis Pro’s cock in her mouth.

“That’s it, you whore… suck his cock like the slut you are,” Mafia Boss says, watching from behind his desk.

The camera cuts to Cheating Wife, sucking on Tennis Pro’s cock, her eyebrows furrowed in mock indignation. A side glance to her watching Mafia Boss husband.

Standing next to Tennis Pro, Bodyguard 2 grabs the back of Cheating Wife’s head by the ponytail and aggressively slams her face into Tennis Pro’s big dick.

Cheating Wife gags in mock protest.

Sitting at both ends of the couch, Junior unzips his pants and pulls out his dick and starts to slowly jerk himself. I do the same… He’s rock hard. And so am I.

Junior’s the same thickness as me, but longer and with a bigger fatter head. It’s such a pretty cock. Like a porn star’s – with a perfect head, and throbbing veins leading down to a perfect tuft of hair.

Junior looks over at me and smiles. That’s my cue…

I slide over and flip onto my knees, grabbing the base of his dick. I start flicking his pretty head with my tongue and he lets out a small moan as he releases his hold around his dick and leans back, relinquishing control of his cock to me.

It’s not long before he’s leaning back with his hands behind his head watching the video and I’ve got his whole cock in my mouth and I’m slurping loudly.

The camera follows Mafia Boss as he walks around his desk toward the pair.

Mafia Boss motions Cheating Wife by her shoulders from her knees to the couch.

Cut to Mafia Boss lifting Cheating Wife’s tennis skirt and pushing her knees back to expose her little pussy.

“Eat her out!” he barks at Tennis Pro.

Bodyguard 2, takes Tennis Pro by the back of the head, pushes him to his knees and shoves his face in between her legs.

Tennis Pro starts to lick and tongue Cheating Wife’s tiny pink pussy lips.

Because Junior’s dick curves slightly downwards, I know that I can get his cock the farthest down my throat if I face his dick, so I manoeuvre my body beside his so I’m facing down on his cock.

I’m fucking his dick with my throat so hard and deep that I’m slobbering all over him. And he loves it.

“Now fuck her!” Mafia Husband demands, “Just like you do when you’re supposed to be playing tennis… Show me how you fuck my slutty wife’s cunt.”

Cut to a close up of Cheating Wife’s pussy, wet from Tennis Pro eating her out.

Tennis Pro takes his fat cock and slides it in.

The camera cuts to a close up of Cheating Wife as she moans.

From behind the couch, Mafia Husband holds her still with his hands behind her head and her neck, while Tennis Pro start to fuck her.

Junior is hard. And his dick is wet with my slobber. I cannot handle it anymore. I want Junior’s dick inside me.

I stop abruptly and shoot straight up on my knees. Junior stiffens his back and looks at me, slightly startled by my fast change of position.

Looking him straight in the eyes, and with one hand on the arm of the couch and one on the other side of Junior, I throw my glued-at-the-ankles-pointed dancer feet into the air and swing them around to land in between Junior’s legs.

Our eyes are still locked together as I kick of my shorts that are hanging on my left ankle. I stand-up and turn my back to him to face the TV, swinging my head to look at him over my right shoulder. I’m dancer posing with a slightly arched back and my right ass-cheek higher than my left.

I bet that would have made a killer bedroom dancer poster.

I pick-up and set my left foot on the couch, my ass facing him, and reach between my legs to grab his hard, sloppy wet cock. With my mouth still full of saliva I spit into my other hand and rub it against my hole, quickly letting a finger slip in to test that it’s wet.

I spank my rock-hard glute, leaving my red handprint behind embedded in my circular ass cheek, as if to wave to him.

Although he’s initially surprised, Junior instinctively puts a hand on my lower waist, to help steady my balance. But I don’t need it. I’m a competitive dancer. I’ve spent lots of time in deep grand plié, not only in the dance studio, but on top of my upstairs bathroom counter so I could watch in the mirror all of the objects I’ve shoved in my tight little teenage boy hole.

I manoeuvre the head of his dick and feel it against my asshole lips.

Junior’s cock shaft is rock hard and sloppy wet with my spit and like I’ve done with the brush handle earlier, I hold his dick steady as I lower myself onto it. I can feel his dick spread my hole and nudge its way in.

I’m a bit surprised as Junior’s cock feels thicker than my brush and I stop for a second after the first few inches to process the sensation. I’m determined to get his dick in my ass, so I try again and this time I’m able take it all in. I have my back arched and his dick is almost totally inside my ass.

“Fuuuuuuck,” he moans, slapping my red handprint harder than I did.

With my right leg still on the floor and my left leg on the couch, I start to move up and down on his dick. Junior has his two hands around my waist and is guiding me. I lean back with my right hand on the arm of the couch and put my right foot up beside his other side, so I’m totally squatting on him, leaning back almost perpendicular, hovering over him.

I can feel his fat cock just fill every inch of my insides. As I begin to bounce faster, it feels like he’s actually getting bigger and deeper, as if he’s filling my stomach.

“Fuck… Fuck… Fuck,” he keeps saying as I jump up and down on him.

Mafia Husband and his goons have their cocks out and are stroking them, while Tennis Pro is pounding Cheating Wife, from behind on the couch. 

She’s on her hands and knees and her little skirt is up around her waist now.

The camera cuts to Cheating Wife’s face.

With his free hand, Mafia Husband is forcing Cheating Wife to look up at him while she’s getting fucked by Tennis Pro.

Cut to Mafia Husband, “You like that?” he asks her.

Cut to Bodyguard 1 who reaches down and smacks her already red ass.

Cheating Wife winces, not looking away from her husband.

Tennis Pro smacks her ass again.

Cut to Mafia Husband, stroking his cock, “Answer me!” Mafia Husband orders.

Cut to Cheating Wife getting pounded from behind, “Yes!” she screams, “Yes! I love it!”

Junior pushes me forward and he slips out of me. As he jumps off the couch, he looks at his dick and strokes it a few times.

“Did you clean out your ass?” he asks, spitting into his hand to add more spit to his cock.

“Yeah, man,” I answer, “I want you to fuck me.”

I put my hands on the floor, drop to my knees and stick my hole in the air, over-arching my back like only a dancer can. He squats lower and shoves his dick back in my ass. Hard.

“Whoa!” I instinctively blurt, quickly looking back at him and holding him back with one hand to try to stop him for a second.

Just as soon as my hand meets his lower torso, Junior swats it away, pushing me to fully face away from him. Grabbing my waist, he starts to pound me, harder than Tennis Pro is fucking slutty Cheating Wife.

In fact, Junior is pounding me as hard as Head Pirate fucks the Captain.

He’s thrusting so aggressively and smashing so hard against my dancer muscle-ass, that it’s like being punched in my stomach… from my asshole. Every muscle in my body is flexed hard to brace me to take the blows.

Getting tired, I instinctively try to crawl away from him to escape the pain. But he doesn’t let up. He doesn’t let me go.

Junior is thrashing so hard sometimes my knee lifts off the ground; and I’m squirming, hands bracing the floor, on one foot, my other foot in the air.

It’s my turn now to say... “Fuck! Ugh… FUCK!” I scream, as his thrusts get faster and faster.

I am so overwhelmed with sensations; my whole body is firing in constant spasms of painful pleasure, that are so strong and seemingly endless that I feel like there is no time to recover between thrusts.

Giving in to his grip, yet still trying to mange the waves, I drop my chest to the floor in between my screams, hard grunts and groans in an effort to better brace myself to take his thrusts.

For a second, I’m concerned that there may be a neighbour outside that can hear the slapping of his body against my hard, round tight ass, together with my screams and grunts. And the thought heightens my pleasure.

Junior’s grunting now with each forceful thrust. “Argh… Aargh… Aaargh… AAAARGH!” he roars as his thrusts suddenly stop. His fingers digging into the top of my thighs so tight I will have bruises there for over a week.

He thrusts again… and after a second, again.

My whole body is convulsing now and with a few seconds in between his last few thrusts I know that he’s orgasmed. I can feel wet drip down one leg. I feel a little pulse in my ass and realize he’s still shooting inside me, but he’s not moving. Just holding me still with his cock inside me, spasming... and filling me with his loads.

After a second, I press my ass into him and spread my hole as much as I can. Then, squeezing my ass as tight as I can around the bottom of his shaft, I try to milk every last drop, moving slowly back and forth, pressing my ass against him, and pulling away – squeezing him each time with my hole.

“Ohhh…” he whispers. Holding on to my waist now, as if to steady himself instead of me. His head is flung back and we are both sweating. He regains his composure and falls back on his heels.

His wet cock slides out of my ass. 

On her back and covered in jizz from the two Bodyguards and her Mafia husband, the camera pans to Cheating Wife’s pussy.

Tennis Pro pulls out and the camera stay close as he blows his load on her furry little pussy.

“Clean it up,” Mafia Boss commands.

Cheating Wife wipes the cum from her face and scoops it into her mouth, as she swings herself onto her knees and starts sucking Tennis Pro’s dirty fat cock clean.

As the scene starts to slowly dissolve into the next scene, you can softly hear Mafia Boss say: “You fucking cum slut.”

Junior is on his knees. His dick is still hard and covered in cum.

Prior to tonight, I had just taken his loads down my throat. Often feeling him shoot while deepthroating him, swallowing it all, careful not to let any drip so we didn’t have anything to clean up. But now, still on my hands and knees, my ass is dripping with his hot jizz.

I turn around to face him, not thinking that I should be careful not to brush my dirty hole on the carpet but thankfully not sitting all the way down, so I don’t think I do.

Instead, like Cheating Wife, I bend right over and start to lick and suck his swollen cock clean.

Junior’s entire body jerks hard with my first lick and knowing how sensitive his head is right now, I quickly grabbed the base of his cock, gripping tight to ground him. This not only helps steady him, but it also keeps the blood there too.

I continue to lick his cum-wet cock. Gently at first, then taking his softening dick into my mouth and I didn’t stop until I tongue washed his cock and balls and removed every bit of teen drummer nut.

It was the moment I knew I was a cum slut.

… and, yes, this started me well on my way to becoming a faggot hole.


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