Wanna Bet - Chapter 3

It's been a while but, by popular demand, Wanna Bet is back!

When last we left them, Jackson had groped Kane and gotten caught, before being dragged outside, where he confessed to his obsessive compulsion to do his own dares. Kane took full advantage and made Jackson give him head, before taking his jockstrap and saying he couldn't cum until they next saw each other.

Read on for the next instalment, and give the post a like if you enjoy it!

As I woke up and the memories from the night before came back to me, my cheeks heated, and my cock immediately jumped to life in the snug confines of my sleep shorts.

Kane had left me in the alley behind the club with no underwear and the back of my jeans ripped wide open, my cock hard as granite and leaking like a faucet.

I had never been so horny in my entire life.

Walking back through the club with my ass on show through the epic rip he’d made in my jeans, I was surrounded by people laughing, and even a few that decided to cop a feel.

By the time I’d gotten outside, I was so ready to blow my load that I had to squat down on the sidewalk and breathe through the tingling sensations in my balls before I ended up cumming handsfree.

I had never experienced such a rush in my entire life.

And I wanted more!

Kane’s number was on my phone, but I had no idea how to approach a conversation with him in the cold light of day. Without being drunk and without the adrenalin rush, I just felt unsure of myself.

Shaking my head to try and rid myself of Kane and his incredible ass, I got out of bed and hit the shower, being extra careful to not touch my dick more than necessary.

Once I was dried, I rifled through my closet and pulled out a pair of navy suit pants, a white shirt and a pair of skimpy hot pink boxer briefs.

Oh, you can do that better than that when you’re this horny. I’m sure you wouldn’t have the nerve to wear something silky that would tease your cock.

I practically growled in my throat at the irritating voice in my head that was intent on getting me in trouble, as I muttered to myself, “Wanna bet?”.

Rifling through my underwear drawer, I found a skimpy pair of silk bikini briefs, which were white and had previously teased me like crazy when I’d worn them. I pulled them on and immediately felt my cock tingle at the sensation of the silk rubbing against my balls.

Fuck, I was never going to be able to wear these all day!

Trying to ignore my eager cock, I pulled on my suit pants and my shirt, added a black leather belt, a pair of dress shoes and some sheer socks.

If nothing else, I looked sexy as fuck today, and that made me smug as hell as I headed for the car.

The morning passed in a blur and before I knew it, it was nearly 2pm and I was finally having a sandwich before I hit the stack of work I had to plough through that afternoon. It was just as I took my last bite than my phone vibrated in my desk, and my heart thundered into an erratic pace when I saw who the message was from.

Kane!

Hey Jackson, I hope you’ve done as you were told and haven’t blown your load yet. I think I need to get to know you a little better before I fully take advantage of your little dare problem, so let’s have dinner tonight – Henry’s on Isla Street at 8. In the meantime, I want to see what you’re wearing.

I reread the message six times, my cock hard as a rock by the time I put my phone back down.

The thought of having dinner with Kane was a dream come true, but this wasn’t a date, he just wanted to manipulate me and completely abuse the fact that I had an issue with saying no to the stupid voice in my head.

I gave my dick a quick stroke through my suit pants and took a sharp intake of breath at how damn good it felt. The tent I was making was obscene.

I’m sure you wouldn’t send a pic of that to Kane!

“Wanna bet?”

I snapped the photo so that he could see my white shirt and the bulging tent in my navy suit pants, before replying to his message with a simple, “dinner at eight sounds perfect!”

Before I even managed to put my phone back down on my desk, it rang, and I was stunned to see that it was Kane.

“Uh, hello,” I said, my voice sounding breathy.

There was a deep chuckle down the line, and that voice made my whole body light up. “Hello Jackson, it looks like you’re still hard.”

I did a quick check to make sure my office door was closed. “That’s because someone left me with blue balls last night.”

Kane chuckled again. “Really? Not me. I had a phenomenal blowjob and blew my load all over the guy.”

The memory of Kane’s load splattering against his face made my dick pulse against the tight confines of my silk briefs. It was one of the most suckable cocks I had ever come across.

“Lucky you,” I said, my voice still quiet.

“If you behave at dinner and do as you’re told, you might get some release today.”

“Might?” I hissed down the phone.

Kane laughed. “If you do as you’re told. Maybe we should test how obedient you’re feeling today. I’m sure you wouldn’t stand up, drop your pants and send me a pic of your undies right now.”

I practically whimpered as I said, “Wanna bet?”

“Get to it, I have a meeting in fifteen minutes and I’m in need of some jerk off material.”

Kane hung up and, almost in a daze, I stood up from my chair, did a quick check that no one was walking near my office, and unbuckled my belt. The clink of the metal seemed insanely loud as I let the belt go and unbuttoned and unzipped my pants.

Pushing my pants to mid-thigh, I grabbed my phone, took a speedy photo of my hard cock straining against my silky white briefs, a damp spot at the head, and yanked my pants back up.

As soon as I’d sent the photo to Kane, I did up my pants, buckled my belt and sat back down, my heart hammering in my chest and a light sheen of sweat on my brow.

Now that’s what I’m talking about! Leave that dick alone . . . for now!

I stared at the message, shocked by how bold I’d been.

Yes, I’d gotten pretty bold in recent years with my self-dares, but I’d never done anything so openly in the office before.

It took some time for me to calm down enough to get my head back into work, but even when I did, my cock didn’t fully deflate all afternoon.

When I’d eventually finished getting through some of the urgent work on my desk, it was gone 6pm. I drained the dregs of the coffee mug on my desk and was just about to pick up a new manuscript when my phone rang.

Kane!

“Calling to cancel?” I asked with what I hoped wasn’t disappointment in my voice.

“Absolutely not,” Kane said with a growl to his voice. “I just fancied an early appetiser. Have you got some headphones?”

I picked up my AirPods. “Yeah, why?”

“Put them in so you can walk and talk, you’re gonna need your hands free.”

I could hear the smile in Kane’s voice as I put my AirPods in, pocketed my phone, and stood up.

“And where exactly am I going?”

“I want you to head to the boardroom or a large meeting room,” Kane said. “Assuming there’s something like that in your office.”

“There’s a boardroom on the top floor. Why?”

“Just head up there,” Kane commanded.

My feet led me to the elevator, and I climbed in and hit the button for the top floor. Kane stayed silent in my ears as the elevator took me up the six flights to get to the top.

Mercifully, the exec floor seemed to be empty as I pushed open one the double doors to the boardroom, where a large oak table and sixteen leather chairs sat.

“I’m here,” I said, my voice timid in the large space.

“Good. Now, I’m sure there’s no way in hell that you’d strip down to your underwear in the boardroom, whilst you facetime me.”

Kane’s rumble of laughter made my knees weak as I instantly said . . . “wanna bet?”.

“That’s what I like to hear. Switch to facetime, set your phone down and get your shirt off.”

Almost in a hypnotic state, I hit facetime on my phone, my cock twitching at the sight of Kane’s handsome face as I placed my phone on the desk, leaning it against an empty water jug.

“Now, the shirt,” Kane said with a grin.

I slowly undid the buttons on my shirt, revealing my furry pecs and my toned stomach.

“Toss it on the floor,” Kane said as I pulled the shirt free from my body.

Doing as I was told, I let my white shirt float into a heap on the floor.

“You can leave your shoes and socks on, but I want those pants off.”

My dick was leaking precum at an alarming rate inside my briefs, as I once more unbuckled my belt in an open part of the office.

Kane growled when he saw how damp my white briefs were as I removed my pants and tossed them on top of my shirt.

“Fuck, you look good. Those briefs are . . . mmmm . . . turn around.”

Obediently, I turned around so Kane could see my impressive bubble butt, barely contained within the white silk.

My cheeks were flushed, and I felt suddenly very hot as Kane lowered his camera to show the meaty bulge in his tan slacks.

I wanted to jerk off so badly, my dick twitching in my briefs as sweat glistened on my chest.

“By my reckoning, you probably have only a short time until the cleaning staff turn up. So, here’s what’s going to happen. You’re going to take off those slutty briefs and get on all fours on the conference table so that I can jerk off to that incredible view.”

“Wait! What? I can’t! What if someone walks in?”

Kane chuckled. “I am sure you won’t do what I’ve asked. You’re way too much of a wimp.”

Oh fuck, this couldn’t be happening.

“Wanna bet?”