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Wanna Bet - Chapter 4
🕑 Added 2025-08-27 19:06:24 +0000 UTCJackson and Kane are back! When last we saw them, a steamy FaceTime call had resulted in Jackson stripped down to his briefs in the conference room at work, and Kane doesn't want to stop there.
I hope you guys enjoy this new instalment - let me know in the comments what you'd love to see happen next!
I couldn’t believe I was stood in the boardroom in just my socks, shoes and skimpy white silk briefs, my cock hard as hell and tenting the material so much that I was surprised it hadn’t ripped through. Kane’s handsome face looked like the cat who’d got the cream on my phone, and I’d just taken his bet that I wouldn’t take my briefs off and get on all fours on the table.
I had absolutely no idea how many people were left in the office, or how many people might be on the floor I was on, or how many people might come this way looking for something?
Either way, I’d taken the bet and my briefs needed to come off.
Facing my phone, I hooked my thumbs under the waistband and tugged my briefs to mid-thigh with one quick, sharp movement. My dick hit my stomach with a meaty thwack and Kane chuckled at the sight before him.
“You really are desperate for release,” Kane growled and just the sound of his voice made my dick twitch.
“Does that mean you’re going to let me get off too?”
Kane gave a bark of laughter. “I don’t recall saying that. Now get on the table.”
Trying to ignore my ever-growing frustration, I kicked off my briefs and climbed up on to the conference table, making sure to keep my ass facing the camera. The table was a little wobbly but once I felt reasonably secure on all fours, I arched my back and pushed my ass out, knowing that my cheeks would be spread just enough to give a teasing glimpse of my hole.
“Fuck,” Kane hissed between his teeth. “That’s exactly what I need.”
I heard the sound of unzipping and turned to look at my phone to see if I could make out what Kane was doing but he immediately told me to face forward. Feeling even more frustrated that I couldn’t even get a glimpse of the cock I was lusting after, I settled for grinding my ass back and forth a little, enough that Kane growled again.
“Fuck, that view is perfect.”
I was about to say thank you, but I heard the unmistakable moans and grunts that signalled that Kane had just blown his load.
“Good boy. I’ll pick you up from your office at 7:45. Be out the front.”
I turned around to look at my phone, but Kane had already disconnected.
And it was just at that moment that I heard voices coming from further down the hall. I jumped off of the table, grabbed my briefs and yanked them on, my sensitive cock making me wince as I shoved my hard length back into the tight confines of the pouch. I pulled on my shirt, doing the buttons up as quickly as I could before grabbing my suit pants and dashing into the corner of the room. With my shoes still on, it was a challenge to get them on quickly, but I just managed to button them as two colleagues that I didn’t recognise walked past the glass walls of the conference room.
“Is everything okay in here?” the younger of the two men said with a frown.
“Yes, I was just checking the equipment ahead of a call tomorrow.”
I had no idea how I came up with the lie so quickly, but they seemed pacified, and after giving me a nod, they both walked on.
Looking down to see how obvious my bulge was, I was shocked to see that my fly was undone, and the damp front of my briefs was fully exposed. I gasped and yanked up the zipper before straightening my shirt and heading back to my desk.
No sooner had I sat down, my phone vibrated.
Given how sensitive your dick appears to be, I don’t think silk is such a good idea. There’s not a chance that you’d take those briefs off and go commando when I pick you up, and you certainly wouldn’t give me those briefs when you get in the car.
My dick throbbed as I read and reread the message from Kane. If he thought silk would tease me, he had no idea how horny I’d be going commando, and the idea of handing my briefs to him was so hot that I thought I’d cum handsfree right there at my desk.
I text back those two words that were my undoing. Wanna bet?
I waited until 7:30 before heading to the restroom. The office seemed to be empty, but I had no wish to try and remove my briefs in my office and risk anyone catching me. I’d already come close to getting caught in the conference room and I had no wish to repeat that.
Once I was safely in the restroom, I locked the door and bent over to untie the laces on my black leather dress shoes. With that done, I toed them off and removed my suit pants. My dick had calmed down to a semi but as soon my pants were off and I saw my reflection in the mirror, it immediately hardened back to full length.
Part of me was tempted to disobey Kane. I wanted to jerk off and cum so badly. It would only take a matter of seconds, and I was certain that if I cleaned up, he wouldn’t even notice. I contemplated the idea for a few minutes, even wrapping my hand around my length, but as soon as I felt my dick throb in anticipation, I let go and yanked down my briefs.
For some reason, I couldn’t do it. I wasn’t sure whether it was Kane I couldn’t disobey or whether it was my own twisted masochism that wouldn’t allow me to do it.
When I picked up my white silk briefs, I was unsurprised by how much precum I’d leaked into them. The pouch was damp, and the stain was obvious. I knew that Kane wanted to see how much I’d ruined my own undies and the idea that he’d be inspecting them made another bead of precum leak down the side of my dick.
I pulled my pants back on and carefully zipped up, mortified by the obvious hard length of my cock. Anyone I walked past would clearly see my predicament and I prayed that the office would be clear when I headed downstairs.
Pocketing the briefs, I put my shoes back on, laced them and headed back to my office to retrieve my jacket and wallet, my cock not softening in the slightest.
Mercifully, the trip to the front of the office was devoid of any of my colleagues and I breathed a sigh of relief when I stepped outside and walked down to the curb.
Just as the clock on my phone ticked over to 7:45, a black town car rounded the corner and pulled up in front of me. One of the darkened rear windows rolled down and a hand emerged, a hand that went straight for the bulge in my suit pants.
Kane grabbed my cock and gave it a squeeze. “Still nice and needy I see.”
I contemplated pulling away from him, unsure how much more teasing I could take, but something about his control excited me more than my need for release.
“Get in, Jackson,” he ordered, and I happily complied, walking to the other side of the car and climbing into the back of the car.
As soon I closed my door, the driver, behind his blacked-out partition, hit the gas and drove away from my office.
“I believe you have something for me,” Kane said, holding out his hand.
I nodded and pulled my briefs free from my pocket and placed them in Kane’s hand. He looked at them almost reverently as he unfolded inspected them. His smile widened as he took in the damp pouch. Kane locked his eyes with mine, almost seeing into my soul, as he brought the briefs to his face. He slowly licked the inside of the pouch and then traced his lower lip with his tongue as he softly growled.
“I should have known you’d taste exquisite.”
The sight before me had my dick leaking like a tap into my suit pants. Every heartbeat made my dick throb and the hungry look on Kane’s eyes had me practically whimpering.
“I’ll keep a hold of these,” he said as he popped open his briefcase and tossed the briefs inside.
“So, I’ll be staying commando for the whole evening?” I asked with a gulp.
Kane gave me a grin that made me feel like he’d just fucked my brains out and knew how much I’d enjoyed every second – just without the actual fucking or any form of orgasm on my part . . . sadly.
I shifted uncomfortably in my seat. “So, an evening of commando whilst we have dinner?”
“Yes, Jackson. You’ll be commando whilst we have dinner and I get to know you better, and no, there won’t be any orgasm for you, unless I change my mind.”
Nodding, I tried to cross my legs to ease the pressure in my crotch, but there wasn’t enough space to do so.
“Feeling a little uncomfortable?” Kane leaned across the backseat and placed one of his strong hands on my thigh, giving it an almost imperceptible squeeze.
“You could say that.”
Kane ran his hand up my thigh until his hand was on my dick again. My entire body lit up like a Christmas tree at the contact and it took every ounce of self-control not to buck my hips. Kane squeezed my dick to the point where it almost hurt, before loosening the pressure and then tracing his fingertips up and down my length.
“I wonder how long it would take you to cum if I kept this up,” he thought aloud.
My voice failed as he pressed a little harder, and embarrassingly, I could myself racing to the delicious precipice where the best orgasm would rock my body.
But then he stopped.
“I don’t think we’re ready to let you go just yet, Jackson. I wouldn’t want to ruin your appetite.”
Kane sat back in his seat and chuckled.
This was going to be one hell of a night!
Comments
Drew GM
Love the control and the teasing ... being backed into going commando ... handing over his briefs ... more teasing. Delicious stuff indeed!
