Page 37 of Her Billionaire Boss
I began to protest, then stopped myself.I did want to please him, and I had been clear that I wanted to submit to him all the time.Here, he was presenting me with a sexy game that he’d gone to a lot of trouble to plan, and it was clearly intended as some kind of unlicensed exposure therapy.
He slid his fingers into me again, coating me inside with more lube.Judging from the shape and size of the toys waiting for me, I would need it, especially since everything in me was drying up from terror.
“You’re a brave princess.”He brushed his thumb over my clit, back and forth, and pumped his fingers.“And an adventurous one.Surely, you can travel this enchanted path to get to your dragon.”
“My dragon isn’t going to come with me?”I asked, biting my lower lip.
“Your dragon plans to watch—and listen—from afar.I have every faith in my princess’s ability to complete this challenge.”He held up the wand vibrator.“It’s dangerous to go alone.Take this.”
I narrowed my eyes.“I’m pretty sure that’s a nerdy reference.”
“You are pretty correct.And just plain pretty.”He pulled his hand away from me and said, “the game starts now.Don’t forget your cards.”
He handed me a small deck of cards, then stood and physically moved my fear-frozen body toward the entrance to the staircase, helpfully marked out with a big “START” arrow on the floor.I put one foot experimentally on the first step.The staircase was wide enough that at least three people could stand across side-by-side, but it felt too narrow and precarious up close.On either side of me, the glass rails revealed the long, long drop to the bottom, while the apartment’s huge windows loomed on two sides.I might as well have been on the wing of a plane.
Matt helped me out by taking the cards from my trembling hands and turning the first one over.“Ah.Blue.Right out there.”
I swallowed.The blue space was the third one out.I put my hand on the railing and slid it as far forward as I could before stepping down from the start space.Pink.The bottoms of my feet tingled.I reached out again, never taking my hand from the railing, and forced my shaking knees to cooperate.I moved across the wide square and down to purple.
When I looked over my shoulder and saw the amount of space I’d already crossed, I almost rushed back.But Matt was waiting there, totally pleased with my progress.He gave me an encouraging, “Good job, princess,” and it was all I needed to move on to the blue space.
Once I got there, though, my confidence faltered, because I had to lean down to pick up the instructions.
“‘You meet a centaur in the Gum Drop Woods.He demands a sacrifice of your tight little cunt.Do your best to satisfy him, and don’t move on until you’ve orgasmed.PS.The centaur loves it when his maidens are loud’,” I read, and rolled my eyes in fond amusement.My dragon wassucha nerd.
“What’s a centaur doing in the gum drop forest?”I called back.
“Don’t question the DM,” he responded.
I eyed the “centaur” waiting for me.The dildo was suction cupped to the floor, which meant I would have to get on my knees and ride it; it appeared most of the challenges were set up that way.All well and good but getting on my knees meant getting lower to the floor, and somehow, that felt like being closer to the edge.Closer to falling.
On top of that, the toy was ridiculously huge, at least two feet long, and the flared head was as big as my two fists clasped together.
There was another bottle of lube beside it.I briefly considered how unsafe the floor would be smeared with it, but that wasn’t my problem, so long as I didn’t step in it.We would have to leave word with whoever cleaned it up and—
Well, I hoped that person wouldn’t be Matt.I would feel wretched if he got hurt picking up all these toys himself.
But this thing required truly heroic amounts of lube, if I was going to get it inside me even a little bit.I squeezed the bottle over the top, straight down, drizzling it all over, until there wasn’t much to finish with my hands.Then, holding onto the railing and whimpering with fear, I got on my knees.
Once I was on all fours, it wasn’t so bad.Sure, I could still see straight down to my certain doom below, but in an emergency, I could flatten like a pancake and hopefully not tumble over.
I glanced back at Matt, still watching with amusement from the top of the stairs, took a deep breath, and got into position.If I was supposed to be imagining a centaur, then I assumed hands-and-knees would be the default.I reached between my legs and took the huge silicone cock in my hand.It was surprisingly bendy, which helped me angle it right.I had to push with considerable force to get even the tip in; my bone-deep terror had tensed my entire body up.My pussy was basically locked.
What would a centaur do?I thought.With a deep breath, I sat back, forcing the whole, huge, weirdly shaped head of the thing inside me with an “Ah!”of shock.
I rose up a little and sat again, scooting back on my knees to take more of the ridiculous thing inside.Between the size of the dildo and being separated from the yawning void of mortality by a single pane of glass, this task was more difficult than Matt probably intended.I smirked to myself at the thought of him scrolling through option after demented option on some specialty toy site, using his devious nerd brain to come up with ridiculous scenarios.I was sure he got plenty of enjoyment out of that.
And, frankly, out of watching me do this.He still sat on the bench at the top of the stairs, but he had a clear, if distant view of me.
I gave one more experimental scooch backward and hit my limit.There was easily a foot of the thing that I hadn’t inserted.There were clearly far, far braver people in the world than I.
I turned on the vibrator, highly doubting that even it would help me let go of my terror long enough to forget the looming potential drop, but once I closed my eyes and pressed it against my clit, I relaxed some.I rocked back and forth on my knees, getting a little motion out of the dildo, and it felt shockingly good.The ridge of the calla lily head felt amazing rubbing on my g-spot.I rode the toy in quickening, shallow jerks of my pelvis to maximize that delicious contact while the wand pulsed and buzzed me toward a speedy climax.
A strong one, too.I let out a shout as my muscles seized and trembled and the electric fire of release swept through me.If I weren’t so damn scared, I would have fallen flat on the floor to recover.Instead, I wiped my lubed hand off on my thigh as best as I could, reached for the handrail, and pulled myself up on weak legs.The dildo slid from me with a pop.
I pulled another card.Pink.It was the next square.
I looked down at the length of staircase still to go, a winding path of perversion.This could take hours.
