Number Eighteen

By jack.straight

Published on Oct 28, 2023

Gay

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It was a good night.

I'd established primacy over Colin. This young "straight" guy had told me--first in my words, then in his--that he wanted me to suck my dick and get fucked by me afterward. His subservience had turned Christopher on, and vice versa. Colin had gotten off with a finger deep in his own asshole.

Now he was waiting for his chance for me to fuck him.

It was my decision to give him a couple of nights between our first session and our second. The anxiety of the decision would leave him on edge. I like to fuck them when I can see a little uncertainty on their faces. Though I also like to fuck them once they've surrendered to me.

I just like to fuck them, I guess.

Chris is eagerly anticipating it, the big "Number 20"--the day he gets to take his cage off. He's gotten me off like a wizard, like a gay Harry-fucking-Potter. Kudos, Chris.

But Colin... Colin must be losing sleep. His mind is running a thousand miles-an-hour. He had never planned on going gay; now he's begging for it.

Chris texted me Saturday. "Do you want us to do anything to get ready before we meet on Sunday?"

Hmmmm, I hadn't thought about it.

"No need to lube yourself up in advance. I want you to learn how to do that from each other."

(And I want to watch.)

"Oh, and tell Colin to wear briefs."

(And let's see how much he has submitted to me so far. If he's wearing boxer briefs, I'll throw him into the forest.)


The doorbell rang at exactly 1pm. Are your fuckbuddies as prompt as mine? Might I recommend you take a firmer hand with them?

The two sophomore studs stood next to each other sheepishly, Christopher full of eagerness but trying not to show it, Colin unable to look me in the eye for fear of what I was going to put him through today.

You should be scared, boy. I jerked off just a half-hour ago just so I can fuck you longer and harder. You're going to feel it, baby.

"Come on in, boys."

I sat them into the living room; I thought that a subtle reminder of our last fuck session would be helpful to Colin.

"Would you boys like a beer?"

"Sure," mumbled Colin.

As I grabbed a couple of session IPAs from the fridge, I realized that giving these kids alcohol was the first thing I'd done to them that was illegal. They really ought to change the laws, I thought, because half of what I've done to Chris should be a felony.

We settled into the living room with our beers. I put my hands on Colin's shoulder, gave him a bit of a massage. I made Chris sit on the floor.

"Well, fellas, no need for a lot of warm-up. Let me see you in your underwear."

Chris stood up and immediately stripped down to his white briefs--the ones that his mom no doubt bought for him, the ones he's worn for years, the ones he's cum in a thousand times while thinking dirty thoughts about other boys.

Chris was already hard.

Had Colin followed direction? Or would I have to throw him out in the woods wearing just his boxer briefs?

He stood up, pulled his sweatshirt off over his rippled chest, his washboard abs.

He unbuttoned his khaki shorts and slid them down to reveal... a pair of Christopher's white briefs. They were tighter on Colin than on Chris but still a fit. The slightly off-white color turned me on--I imagined all the times Chris had cum in them before Colin had worn them. Chris probably shot his load in those while he was sucking Colin.

"Very good, Colin. Why don't you join Christopher down on the floor?"

The two eager college boys were on hands and knees in front of me, ready to follow my next instruction.

Christopher had a boner that threatened to tear through his underwear. Big surprise from that little faggot, but I noticed that Colin's dick was already tenting as well. That was hot.

I revisited the rules.

"Whatever Colin does for me today, Christopher can do for him going forward. If Colin sucks my dick, Christopher can resume giving Colin blowjobs. If I fuck Colin, Colin can fuck Christopher. If I piss on Colin, then Colin can piss on Christopher. Et cetera."

The guys looked nervous... no one had said anything about pissing.

"So why don't we start with a tag-team blow job, and see where we go from there."

They looked at me like students who haven't done the reading.

"Take turns sucking my dick, you... brilliant boys."

I have a personal policy: no insulting your students.

I slid my jeans down, unzipped my hooded sweatshirt, slid my underwear down over my hairy thighs. My dick was already showing signs of life, a chubbed-up six-and-a-half inches on its way to eight fat ones.

As these two gorgeous sophomores knelt next to each other, their hard dicks pointing to the sky, my fat one flopping near their faces, ready for their best tag-team effort, Colin got a little saucy.

"So, if Chris and I suck your dick, does that mean that you and Chris will have to team up and suck mine?"

He had a look of cockiness... a funny time and place for arrogance, down on his knees with my hard dick primed to shove into his mouth at any second.

I looked at him with genuine compassion. I massaged his head just above his left ear.

"Sweet Colin... I am never going to suck your dick."

His eyes watered as the revelation hit him--that he was my fag, not the reverse. He sat there with his mouth slightly open from the shock of realizing that he was a beta,' not an alpha.'

I reached around the back of his head, guided my cock with my other hand, and stuck my dick into his mouth.

He stared up at me with the first three inches of dick in his mouth--just enough to leave no doubt that he was a cocksucker. His eyes still glistened with hurt... and something else as well. Surrender?

"You're a cocksucker now, Colin."

We exchanged eye contact for a moment--a clear expression of the transaction between us, a give-and-take. I would give; he would take.

I began to thrust into his mouth. His mouth was warm and fairly tight: not bad. But he was clearly a rookie.

I gave him the basics.

"Put a little tension on it. No one wants to fuck a loose pussy. Use your lips and your tongue. Make love to my dick."

I put my hand on the bottom his chin, directed his head upward.

"And Colin, no teeth. Ever."

He nodded. All students need time to learn new ways of thinking. He worked to give me a good fuck with his almost-virginal pussymouth. He couldn't take me deep, but he made an effort to be sensual, caring for the dick, doing to me what he wished someone else might do to him.

Chris, meanwhile, dutifully sucked on my balls. Christopher, the consummate cocksucker. The perfect pupil. The horny faggot.

After a minute, I saw Colin look up at me with passion. Something had been awoken in him. He had always wanted to make love to a dick, had always wanted to taste a man's cum.

I could probably have stayed in just this position for the rest of my life--a dedicated new cocksucker learning as he goes, plus a cockgobbling faggot twink plaintively sucking my balls into his mouth.

Alas, nothing is forever.

"Make out on my dick, faggots."

Colin let my cockhead pop out of his mouth. He protested. "I'm not a faggot."

"No, Colin, you're not a faggot... you're just sucking my dick so you can get another man to suck your dick."

Colin looked up, ashamed. Sorry, bud; you can't willingly take a lesson in cocksucking and then say that.

The two young men weren't sure exactly how to french kiss over my dick at first. I put a hand on the back of each one's head, guided them so their lips were just touching. I slid my dickhead to the slight gap between them.

"Use your tongues."

The boys started licking at my cockhead and the other's tongue. I slid back and forth just a bit to remind them that they were being orally fucked.

With this gorgeous sight in front of me--two handsome, masculine young men in identical briefs, swapping spit and making love to my dick with their tongues--I began to leak precum. The glimmering, slimy liquid coated their tongues, their lips. This seemed to turn Colin on immensely. He began to moan just from the taste.

"Taste good, Colin?"

"Yyyyeah," he replied, his enunciation hindered by the cock on his tongue.

I slid my dick all around, making sure to daub some of the precum onto Colin's smooth cheek.

"OK, time for Lesson #2. Move back. On your knees."

I rose from the couch, stood with my crotch in Colin's face. "Christopher, kneel next to Colin. I want him to learn from your technique--you're an expert."

Chris dutifully lined himself up parallel to Colin.

"Long strokes first. Colin, try to take as much cock inside you as you can."

I slid my dick, now at its full length and thickness, into his mouth. He choked down maybe five inches of it? He made a gagging sound as I hit the back of his mouth. Not bad. He was trying.

"Your turn, Christopher."

Chris slid my dick into his mouth and throat--the whole goddamned rod. Once he had his lips around the base, my dick concealed entirely within his face, he reached up and caressed my balls with his right hand.

"Not bad. Bonus points for the ball play. Now, tell Colin how you do it."

The cock took a second or two to travel out of Christopher's throat. "Just let it slide past your throat entrance. At first you'll think you're going to die, that you won't be able to breathe. Breathing is harder, but you can do it through your nose."

Colin took the direction. He slid about six inches into his throat, looked up with panicked eyes. He coughed and fell back. I think he might have thrown up in his mouth a bit.

"Good first effort, Colin," I said.

"It takes practice," said Chris, an expert due to his own practice.

"Christopher, why don't you reward Colin's effort by sucking his dick?"

(I'll reward him with a load of hot, sticky cum in his mouth.)

Chris jumped down and slurped at Colin's cock with zeal. Colin got back to "fully horny" quickly, and I slid my dick back into his mouth.

We stayed in that position for awhile: I was standing and pumping my dick into the mouth of Colin, who was kneeling and sliding his dick into the mouth of Chris, who was prostrate on the floor.

We all still were half-clothed, me in an undershirt and briefs on my thighs, the boys with their underwear on and just their dicks hanging out.

It was time to get animal.

"Take your clothes off, boys. And take mine off for me."

They slid their briefs down eagerly. They jumped to their feet, teamed up first to pull my undershirt off, then pull my briefs down.

I had a word of warning for them as they continued.

"Now Colin, Christopher can do anything to you that you've done to me. Since you're sucking my cock, he can do the same for you.

"But I've never cum in your mouth. Thus, if you cum in Christopher's mouth before I cum in yours, you've broken the rules. I'll have to send you both home--game over."

Colin looked at me with some alarm. He would have to make me cum before he came himself.

I'm ruthless.

If Chris were smart, would take it easy on Colin's dick. Chris has got a lot to lose too: if Colin cums in Chris's mouth, they'll both lose the game, and I'll throw them both out, never to fuck Chris again... which would break his poor little faggot heart.

Chris was hornier than he is smart, though.

It was beautiful to see him laid out on the floor, his legs spread slightly, his cage pressed to the floor, his plump, fuckable ass catching the afternoon sunlight, his delicate, dedicated mouth searching for Colin's thick cock.

He's a gem, this Chris.

Colin started slurping more sumptuously on my cock, working it faster, his eyes locked on mine, with the desire to make me cum and the fear of failure shining clearly through them. He got more and more worked up, both in his mouth and in his dick. He was so fervently horned up I started to get worried for him. He sucked and slobbered. As he got more worked up down below, he started to moan on my dick. God, that felt good.

Not a faggot, indeed.

Chris, taking his cue from Colin and not helping the situation, started to moan on Colin's cock.

I could tell that Colin was close, that he was going to bust one. His moaning got more intense, a little bit choppy. Fuck, Colin was going to cum, like, right now.

So, kindly, I let my load loose in his mouth. Boom. Just as I shot thick, heavy cum onto his virgin tongue, he blasted his load all over Christopher's face.

I pumped into his mouth for four or five shots. Distracted by my orgasm, I did my best to watch his face, see his reaction to sucking cum straight from my dick.

He looked so pleased. Once we both finished splattering our cum, Colin looked up at me directly with a mouth full of cum, now looking pleased and relieved.

I could see he was thinking about what to do with the load of jizz in his mouth.

I asked, "Do you want Christopher to swallow your loads?"

He looked up at me. He opened his mouth wide to show me the cum, and swallowed it, open-mouthed, in one gulp.

We all three took a few minutes to recover from that one. The boys sat on either side of me, my arm around each of their shoulders. We joked about what a close call that was, I praised Colin's cocksucking skills--told him he was better than Chris was on his first go, which was both cruel to Chris and a total lie. We sipped on our beers and bonded.

As we wrapped up, I gave Colin his final warning.

"Colin, I'll be happy to fuck you today, but I need to warn you: it's going to take me awhile to cum if I do.

"And believe me, you definitely want me to cum." I said, nodding toward Christopher's ass.

"I can take a fuck from you."

Huh. A little saucy still. I stared down at him.

"I want--I want to get fucked. Till you cum. No matter how long it takes."

There's my boy.

"Why don't you eat each other's asses while we get horny again?"

Colin and Christopher looked at each other tentatively. Obviously Christopher, who was into anything with any guy was eager. Colin, well, Colin may not have eaten much ass up until this point.

"You can eat Christopher out--then he can eat you out."

Chris got on all fours. He held his pussy ass slightly upward--the perfect angle for a rim job.

Colin tentatively swung in between Chris's knees. He put his hands on Chris's round buns, started reaching for the hot button. Once he found it and pressed, Chris let out a loud, sensual moan. I think Colin was surprised by how responsive it could be. He worked his finger in a bit, enjoying the new experience.

"Get your tongue in there. Give him a taste."

Colin bent over further and used his hands to brace himself near Christopher's opening. He pulled the cheeks apart and gave his clean butthole a lick.

I think he's got an oral fixation, I thought. He started working Christopher's ass like it was his favorite hobby.

After a few minutes of deep-diving with his tongue into Chris's rosebud, I told them to make out. They rose to their knees, their new boners pressing hard into each other's stomachs as they thrust their tongues into each other's mouths.

"Christopher, Colin has earned the right to get tongue-fucked by you." Colin fell into position, all fours. Chris dug right in. Pretty soon, Colin was moaning softly.

"Feels good, doesn't it?"

"Mmmmmmmmhmmmm." He purred.

"Make out."

They went back to kissing.

"Now you know what your own ass tastes like," I said to Colin.

"OK, it's time to lube up. This hot girl-on-girl action has me ready to fuck you."

I passed them a full bottle of Swiss Navy.

"Spread your legs."

They sat back down on the floor and spread their legs open to face each other. Chris squirted lube into his hand, passed the bottle to Colin. Colin squirted some lube on his hand.

"Lube each other up."

Chris delicately reached for Colin's asshole with his middle finger. Colin saw the movement and mirrored it. They slid their asses close to each other, their legs open and crossing over each other's.

They took their time warming each other up, playing with the surface. Chris sunk the top knuckle inside Colin. Colin started to groan a bit as Chris pressed against his inside walls.

"Stick two fingers in him."

Chris reached for the lube, spread some, reached into Colin with both index and middle fingers. He gazed into Colin's eyes as he slid them in.

"Work them around a bit."

Chris started to give Colin a deep massage, a massage that only extreme bodyworkers might attempt and extreme fags would receive.

Meanwhile, Colin fished around in Chris's pussy. Although he was not an expert at it, he had Chris turned on enough that he was moaning.

As they moaned together, I considered my options. I could fuck either ass first, or I could fuck them both. I decided to play around with the decision.

"OK, hold your asses up. I'm trying to decide which one of you to fuck first."

They pointed their asses toward me, side-by-side. I could see Chris's slutty, ready pussy. His ass was welcoming me home, telling me to settle in and get comfortable.

Colin's ass was taut, proud, reluctantly inviting.

What am I going to do--skip the straight guy's ass?

I grabbed onto Colin's ass and hips. I warned him, "I'll let you get used to me. But then I'm gonna fuck you."

He didn't move or say anything.

I took that as a yes.

I slid a thick inch-and-a-half into him and held it there.

"How does that feel, Colin?"

"Mmmmmmph..." he cried. I think he was lost for words.

I petted his ass, enjoyed the his muscular, slightly hairy rear end. I massaged his ass. I bobbed my cock in at different angles.

I felt his insides relax.

"I'm gonna give you the whole thing now, sweetie."

He gave a nervous yelp as I slid past his inner membrane.

"Mmmmm... that feels good, Colin. You've got a nice, tight pussy."

".........thanks..."

"Oh yeah, this is gonna be fun."

I started to give Colin a little in-and-out, just taking a couple of inches out then sinking it in, each time just a nudge deeper. When I got balls deep, I pressed my crotch into his formerly virgin, formerly straight ass.

"Do you feel that? That's a real man's dick up your ass, Colin. For the rest of your life, you can tell anyone that you've been fucked by a man."

Colin didn't say anything. He just adjusted his body to take my dick better, more purely up his chute. I didn't care; I didn't need conversation from him at this point. I just needed him to feel me deep inside, to hear me tell him what was happening.

He was in the palm of my hand.

"Let's fuck, Colin."

I began to bounce my dick in and out of him. I slapped his ass on the side. He took the cue, began to move his ass back and forth a bit. He was smart and sexy enough to take it from me.

Chris meanwhile was posed like a well-trained dog next to Colin. I couldn't just leave him there.

"Give me a taste, Christopher."

I pulled out of Colin, who gasped, and slid directly in Chris.

His pussy felt like that of a top-notch prostitute--the kind that knows they can get you off when they want to, who can work your dick with perfect articulation. I pumped in and out of him deep.

"Mmmm... that is one sweet pussy, Christopher."

Chris purred.

"Colin, hop on your back on the sofa. I wanna look in your eyes while I fuck you."

Colin obediently hopped up onto the couch and slid his ass near the edge. He had nothing left to lose, no fake macho pride to preserve. He had a load of cum in his stomach, the taste of Christopher's ass and his own in his mouth. He had taken my dick to the hilt.

He'd gone full faggot--nothing left to hide, nothing to protest.

I put his ankles on my shoulders and set my dickhead at his warm, wet opening.

"I hope you're enjoying this as much as I am, Colin."

I slid into him, watched the expression on his face, a mixture of deep pain and pleasure. I thrust into him steadily, taking the full length of me in and out, watching his face move with the in-strokes and the out-strokes.

His dick looked like it could cum without even being touched.

I gave him his last lecture of the day.

"There's no coming back from this, Colin. I don't care if you marry a woman and carry on the hetero-patriarchy. You put your ass out to be fucked by a man. That makes you a faggot.

"So when you kiss your wife goodnight, or when you make pathetic love to her--remember that you shot your heaviest load while you were being fucked like a bitch. That while you settled for a culturally-approved lifestyle, you wish you were bent over, taking a thick one up your ass."

He looked up at me in hurt, confusion, and... recognition.

"Blow your load in me," he said.

"Christopher, help us out. Hands and knees. We're going to make Colin a `lucky Pierre.'"

Chris assumed the position on all fours. I pulled out of Colin and guided him between Chris's legs. He couldn't wait--he sank his dick into Chris before I even gave any instruction.

"Ohhhhhhh yeah..."

Kids. I pulled in behind Colin, spread his cheeks wide, and began to work my dick up inside him. Then I started to find a rhythm, passed it to the two boys underneath me.

There we were: Chris, caged, on bottom, naturally, taking a rockhard fuck from Colin, his roommate, who was getting eight full inches from me during his virgin assfucking.

It couldn't last long--it was just too fucking hot.

Colin started to nut pretty quickly. His ass muscles clenched my dick in a meaty sandwich. I fought through, worked my eight inches deep inside him. He was holding on, keeping his load back as long as he could so I would cum inside him first.

I may be a dominant man, but I'm a kind man too. I let my load squirt deep inside his colon. Colin, pressed to his maximum, cried out in anguish and pleasure as he released into Chris. Chris moaned like a bitch as he shot a load through his cage. I pounded them into the floor until we all collapsed, spent, loads shot.

We lay there as a sandwich for a few minutes, cum leaking out of asses and dribbling down onto Christopher. Finally, I pushed off of Colin and walked to the shower, leaving the two faggots to think through what they'd done.


When I came back, the boys were leaned against the couch, still naked, silent.

I tossed the keys to Christopher's cage to Colin.

"Maybe he'll want to take another 20 loads from you."

This was my ultimate act of cruelty--giving Colin the role of the top immediately after showing him that he was a bottom.

They'll be back, I thought.

They'll be begging for it.

And I'll be ready.


Did you shoot your load? Tell me. If you're a Colin or a Christopher, write to me at jack.straight@hotmail.com. We can have a chat. Who knows? If I'm nearby, maybe I'll put a load inside you.

Next: Chapter 4: Will Masters


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