Number 19
I had a real predicament on my hands.
On the one hand, I had a sexy-ass college twink who was completely submissive to me. He wore a cage, dressed like a fag--actually, dressed like a cock-crazed slut... not even a fag would dress that way--for me, and slurped on my dick like it was his chief professional goal.
On the other hand, he had to get me off twice more, and each time had to better than Number 18. And Number 18, for me, had been a fucking mindscramble of an orgasm.
I did say it was a predicament, but I didn't say I didn't love it.
Seriously, though--how could he do better? You can only suck and fuck so well. It's like figure skating in the Olympics: if you don't fall, you're pretty much doing it right. What do I need from him, a quadruple axel on my dick? Now that I mention it...
I took a few days to mull it over.
Christopher, meanwhile, was miserable.
These are a few of his texts:
"I am ready to serve you, sir." "Sir, please let me provide you with pleasure." "I will do for you whatever you want me to do, sir."
On the one hand, take it easy, Chris. I'm working on it.
On the other hand, think of how horny Chris has to be. He'd been sucking and fucking me, in a cage, for two-and-a-half weeks. He had begun to get off--just from getting fucked--but now I had not fucked him in four days. I cut him off from sucking his roommate (or anyone else) off, so he couldn't even earn the release of getting another man off. Of course he was practically begging to take more dick inside him.
So this was my cross to bear. I wanted Chris to get me off, but I did not know how. If a campus tour group had seen me walking through campus that week, they might have, by the look on my face, thought I was solving some complex philosophical problem.
Instead, I was brainstorming new, more depraved ways to put my dick inside a student's mouth and ass.
Could be your turn next year, kid. If you get in.
The answer--the moment of revelation--came in a text from Christopher. I was surprised too.
"Sir, Colin, my roommate, wants to use my mouth again. Can I let him?"
Oh, COLIN. This was perfect.
Colin had been getting blowjobs-by-request from Chris. Every. Single. Day. Think about that. When you were 19 years old, what would you have said if someone A) gave you a blowjob every single day, then B) suddenly took that away from you? Your hand would not be an acceptable alternative!
So Christopher was the lure, a blowjob was the bait, and Colin was the prey.
I just had to set the trap.
"Bring Colin to my office today at 3pm." I replied.
Colin and Christopher sat nervously in my office. Colin was sweating--I could smell his BO. Nervous body odor is not the sexiest smell, but I could make it work.
I closed the door.
"Colin, tell us why we're here."
God, I'm a dick. Colin's sweat glands opened up like a flower.
"I, well, I--"
As he stammered, I took a good look at him. He was clearly an alpha by comparison to Christopher--but these things are all relative. I bet he's 5'11" but says he's 6'0". Brown, wavy hair, collegiate straight-guy style (a sweatshirt over cargo shorts). I bet he played baseball in high school.
He had all the false, masculine confidence of a college sophomore. It's cruel: they're led to believe that their knowledge is useful, their input valuable... but somewhere deep inside, they know they're faking it, are just waiting for an adult professional to tell them that everything they think and know is bullshit.
Overall, he's an 8 out of 10. As a conquest--a straight guy who might just suck dick if you play him right--he's a 12.
"Colin, I need you to tell me what we're doing here."
He's smart and assertive enough not to fall for that.
"You know what the deal is."
That's fine, Colin, that's fine. I expected this. You're playing checkers; you think I'm playing chess.
"Here's how it's going to work:"
I'm playing with your fucking mind.
"Anything you want Christopher to do to you... you have to do once for me."
Colin scoffed. I could see a hint of disbelief in his posture, a quick assessment of what it might be like to suck dick, to suck MY dick.
"That is my offer to you. If you accept it, we can meet up soon. I have Friday night available. If you reject it, then you'll be stuck looking somewhere else for your blowjobs."
"But what if--"
"If you and Christopher start something sexual again, I will know it, and I simply cut Christopher off."
"And never fuck me again?!" asked an alarmed Christopher. I think Colin was surprised to see how affected Chris was by that possibility.
"And never fuck you again, I'm afraid so, Christopher."
Chris was (obviously) in the palm of my hand, and Colin was having a moment of doubt. That was a victory for today.
"Here's what we'll do. You two talk it over tonight. It's Wednesday today. Christopher, you give Colin my cell number, and Colin, you let me know what you want to do. I will give you until 5pm tomorrow--Thursday. If I do NOT hear from you by exactly 5pm, I will assume that your answer is `no.'"
The guys looked like they were in passive agreement.
"OK, I have work to do."
I put my head down and began to review next month's journal submissions. The guys sat there for an awkward couple of moments, then got up and excused themselves silently.
Now I play the waiting game.
It was 4:46pm on Thursday when I got a text from a number I didn't recognize.
"I will meet up with you on Friday to do the thing."
I smiled, gave it a couple of minutes.
"I'm assuming this is Colin, and I'm assuming `the thing' is sex. I accept. Have Christopher come with you. Be there at 6pm. I'll serve dinner."
Dinner was a curveball--I thought I might try the slow play.
The doorbell rang at 6pm sharp. That was Christopher's doing, although who knows? Maybe he was rubbing off on Colin a little. I wouldn't mind that at all.
(So long as they weren't rubbing each other's dicks off, that is.)
I'd made chicken parmesan, a family classic, and easy as fuck. I served them wine, and we ate a mostly relaxed meal at my dinner table. Colin's defenses were low--a good start--as we ate. We chatted about majors, about the administration's new policies, about the weather--civilized, polite, boring stuff.
From the outside, this would look like three healthy men having a pleasant meal and conversation--not one step in a sexual-political march towards subservience.
You know which it is.
"Christopher, do the dishes while Colin and I get comfortable."
Colin and I retired to the living room. We sat on opposite corners of the sofa. I didn't say a word. I could see he was getting nervous again.
"So... do we... do it now?"
"Do what, Colin?"
"..."
He flushed bright red. I said nothing, kept my gaze on him.
"Well, oral. Oral sex."
"You want to blow me?"
"I want to get Chris to be able to blow me."
"And to make that happen, you need to suck my big cock."
"I guess, yeah."
"Till I cum.
"..."
"I need to hear you say it."
"..."
"Come over here."
I gestured to the spot in the carpet between my legs. He reluctantly got off the sofa, moved to that spot. He stood there. We made eye contact, the shame and reluctance on his face delicious. I looked at him with expectation and impatience.
He paused for a half-second, then fell to his knees, still looking at me in the face.
"What do you want to do, Colin?"
"..."
"Repeat after me: I want to take your thick cock--"
He lit up beet red.
"...I want to take your thick cock."
"--into my hot little mouth--"
".........into my......hot little mouth."
"I want to get you aroused with some gentle strokes and licks."
"...I want to get you aroused with some...gentle strokes and...licks."
"I want to taste your pre-cum."
"I want to taste your pre-cum." (Interesting: no hesitation on that one...)
"And then I want you to shoot your whole load--"
"And then I want you to shoot your whole load."
"Wherever you want."
"Wherever you want."
"Good boy, Colin."
We sat in silence for a few seconds. It was remarkable: I could see his old spirit fading and a new one emerging.
He reached up for my belt with an attitude of, "well, let's get this over with."
"Oh, no, not that yet, Colin."
He looked up at me in confusion.
I stroked the side of his head tenderly. He sat and stared at me with that confused look, then backed away like a nervous puppy.
"I 've got something I want to show you. Call it foreplay."
I stood up.
"Christopher, will you come in here please?"
Chris walked in, butt-naked save for a white kitchen apron--one that barely covered his caged-and-locked junk, and that left his ass totally exposed.
(I'd planned that.)
"Christopher, I want you to show Colin what he's missing. I know you blew him before--but I think you have some new skills to show, and I want him to know them all before he does anything rash."
Colin was just a stunned spectator.
I stood up. "Christopher, get me ready. Slow and deep."
Chris dead-dropped to his knees, pulled my dick out of my pants like a gay-fucking-Jedi, and slid my dick into his mouth, slow and deep, as requested.
He took it all the way to the root, his lips pressed against my bush. Once braced with my hips, his lips kissing my pubis, he looked up at me. He smiled with his eyes.
"Ohhhhhhhhhh......" (It really did feel amazing.)
"I want you to see this, Colin. Move closer, take a look at Christopher's technique."
Nervous Colin sat on the carpet next to Chris. I slid almost my full meat out till just the tip was on Chris's lips, then buried it again in his mouth, slowly, deeply.
"You can imagine how good this feels," I said, gazing down at Colin, perched on the floor. I could see he was getting a little horny. He absentmindedly pressed against his swelling dick through his shorts.
"Christopher, now that you've gotten me hard I want to fuck you. Did you lube yourself up before you came here?"
Chris nodded his head with my dick in his throat.
I slid out slowly, took my time to glide eight inches of thick meat over Chris's tongue. I laid the length of it on his face--it reached from his chin to his forehead.
I laid my hand on top of it. I rolled it side to side on his face, leaving precum and saliva all over his face and Chris in a state of delirium.
Dick on his face, I gave his next instruction. "Put your hands on the couch and your ass in the air." Without hesitation, Chris hopped to his toes, and bent over the couch in about a second and a half.
"Watch this now, Colin."
I slid my dick, still partly covered in Chris's deep saliva, up his ass crack. I dripped some silicone-based lube-- the kind that lasts--on my dick,. As soon as I hit his butthole (I had him take the buttplug out before he came in tonight... we don't want to expose Colin to all of our kinks... yet), I forced myself inside.
Christopher's ass was warm, soft, tender, and tight... and ready for my full, thick eight inches.
So I gave it to him.
"Unnhhhhh..." grunted a satisfied Christopher.
"Wow," noted an aroused Colin.
"Oh, fuck yeah," said yours truly.
Colin lurked around to the sofa, sat right next to Chris. He was now stroking himself through his shorts openly.
I invited Colin to take it further.
"Take your shorts off."
Colin stripped, pulling his khaki cargo shorts off with two hands. He was wearing black boxer-briefs--aka the underwear of the curious bisexual. Abercrombie, I thought. Hot.
He started grasping his dick from under the waistband.
I resumed fucking Christopher while conversing with Colin.
"God this ass feels good."
Chris moaned deeply in pride and satisfaction.
"Quiet, Christopher."
He went silent. I couldn't blame him for moaning: Chris took deep pleasure in taking a fuck--partly because he could take no pleasure from his own dick.
The fuck was having an effect on Colin. I sincerely think that the sound, the smell, the sight of fucking Chris was so hot as a result that any man would be turned on--I don't care if he's 99% straight, he would be turned on--horned up and ready to fuck this kid.
Colin pulled his sweatshirt over his head. His stomach was revealed momentarily, and I could see his abs were taut. "Do you work out, Colin?"
He nodded with pride, always happy to receive that question.
"Let me see."
He pulled the t-shirt off to reveal a smooth, muscled chest, and round, muscular shoulders. It's so beautiful to see these young men who work out--they've got defined muscles and virtually no body fat.
And hopefully big dicks.
"Nice body. I can see you take care of it."
Colin smiled. He was starting to eat out of my hand.
"Look at this." I dropped my dick into Chris again, plunged a few times freely, joyfully. "You can't get a fuck this good."
"Yeah! It's fucking hot." Colin was stroking his dick vigorously. He'd dropped the strategy--he was just horny now.
This is good.
The plan at this point... well, there was no plan, really, other than to take a really hot fuck out of Christopher. I figured I could ad lib.
"Watch this... Christopher, fuck yourself on my cock."
I stood stock-still. Chris put his hands on his lower thighs and began to work his ass onto my dick, bobbing his hips back and forth a few inches. He pulsed his young ass onto my throbbing dick, working hard to find his angle.
He found it: the firm ridge around my head rubbing past his inner sphincter then mashing his g-spot. He started fucking himself quick and hard.
"Christopher, you can make noise again."
"Unh, unh, unh, unh, unh..." said Chris.
(I have never had a partner who loves dick in his pussy so much.)
Colin jerked off rapidly as he watched this fuck. He looked at me with longing and admiration. I could see he was rock hard under his boxer shorts.
"Colin: take your hands off your dick."
He stared into my eyes, concerned he'd offended me.
"You can touch yourself anywhere except your cock."
He unwittingly bit his bottom lip and started touching his chest, stroking his fingertips over his nipples. He was miserably horny, his dick throbbing hard in his underwear, a two-inch wet spot on the head.
I grabbed Chris's hips and took some of the action back. Chris kept moaning as I hit his spots. His pussy was so soft, so responsive. It had become his primary sex organ, and it was a fucking firecracker.
I had another idea.
"I'm going to make you cum, Christopher."
"UNH! Unh!! Unh!! Unh!!" replied Chris.
"Flip on your back."
I balanced him on top of the arm and back of the couch--I needed a good angle to dig into his ass if I was going to make him cum through his cage.
He held his shaven legs in the air. I rolled my dick around in his ass, playing with different spots inside him as he moaned uncontrollably.
"What do you think, Colin?"
Colin was practically as miserable as Chris was--he had pulled his underwear halfway down his ass, desperate to put pressure on his dick.
"I wanna fuck him."
"We can make that happen, Colin."
I stared in the center of Colin's eyes as I began to thrust right onto Chris's g-spot.
Colin and I both knew what was going to happen.
"Why don't you play with your ass a little bit?" I asked.
Colin nodded feverishly. He pulled his underwear off, revealing a hard, hairy, thick seven-inch cock. No wonder Chris loved sucking it so much.
His dick pressed against his stomach as he reached down to finger his own ass. We stared at each other with clear knowledge and intention.
It isn't necessarily a physical thing; it's more an emotional, a psychological thing. But when you know, you see it clearly: Colin had submitted to me.
So here I was, fucking this pussyboi to the point that I could make him cum with his dick and balls locked in a cage. Just behind the pussyboi was his straight roommate, playing with his own ass and practically begging me with his eyes to fuck him too.
We fucked like that for awhile, Christopher moaning like an animal, Colin daring to sink a finger deeper inside his own ass.
I thought I heard a very light moan as Colin exhaled.
The boys were getting into it.
"Christopher, I'm going to make you cum now." He nodded. His body was covered with a glisten of sweat, his eyes were wet... he was fully aroused. I began to thrust right onto his prostate--I knew that was where the magic was. Chris's moaning turned into something more like whimpering, whining because the pressure was too intense, the pleasure was too much. I hit him hard, hard, hard. He was getting closer.
How could I get him over the edge?
"Colin, stroke your dick."
Colin, his two hands working his own asshole, slipped his left hand up to his dick and began to stroke it long and full. Chris turned his head to watch. He'd been getting fucked out of his mind, so overstimulated he'd forgotten where he was. Now he saw his roommate, horny Colin, about to get off, with his own fingers up his butthole.
The two of them made eye contact, a depersonalized connection, one that just reeked of pure lust.
As they gazed at each other, I mashed Christopher's button a little bit harder. His legs started to shake, then spasm. His ass grabbed onto my dick like an iron glove. I kept fucking him, determined to fuck the cum out of him.
He shook wildly. He cried out.
A load of thick, sticky white cum shot through the front of his cage. He kept cumming as I kept fucking him, the sounds he was making the sounds of pure animal passion.
This was my moment.
"Tell me what you want." I looked at Colin.
"I want to fuck him like you do."
"Tell me what you want."
Colin paused, then looked me in the eye. "I want to suck your dick and then let you fuck me."
"Good boy. Now, let me see you cum."
Colin started shooting right then, an arcing shot of hot, white milk that splattered down on his chest. Arc after arc exploded from his dick as he simultaneously pressed the inside of his ass. The pleasure was so deep that he had to close his eyes. The look of concern on his face as he shot explosively was adorable.
I took to thrusting deeply into Christopher; time to get my rocks off. He looked up in alarm as my full eight inches worked inside him. He knew better than to object--he just had not been this deeply stuffed so far tonight.
No more mister nice guy, Chris.
I pumped him hard and deep, felt him grasping onto me inside. He put one hand on my chest, reached the other one underneath him to grasp my balls. That was good enough; I started to pump my load deep inside of Christopher, a good, heavy load that I shot deep inside him. I slid out entirely, shot a load onto his asshole, then took a deep thrust and shoved that cum back inside him.
As I tapered off, I took us in: we were a cum-soaked mess. Colin, his chest covered in cum, still had his eyes closed, still had his finger up his ass, still had that concerned look on his face. Christopher had a light smile on his face, a load of cum up his ass and another inside his chastity cage. I had my hard dick still planted up inside of Christopher, and a promise from Colin that next time I got off, it would be when I popped his cherry.
"Boys, thank you for an entertaining evening. Come back on Sunday afternoon at 1pm. And get your work done in advance because we're going to need the rest of the day."
Did you shoot your load? That's hot. If you have any thoughts or responses, are an aspiring Christopher, or wish someone would put you in your place like I did with Colin, write to me at jack.straight@hotmail.com.