Once she was properly bound, he picked up the larger of the two silicone dildos, a rabbit with a handy clit stimulator attached. He removed the sterile shrink wrap and slathered the tips with lubricant. “I’m going to push this inside you. Try to keep it in place until I get the harness on.”
He moved behind her and reached around, positioning the lubed vibrator at her entrance. He tried to ignore the proximity of their bodies, arching his back slightly so his hard-on wouldn’t touch her back. Slowly and carefully, he eased the dildo inside her tight passage. He adjusted the rabbit ear, nestling it against her clit. She sighed softly. That was a good sign—she was accepting the phallus easily and was clearly aroused.
Now came the hard part, at least for her. He stripped the second, slimmer dildo, of its wrapping and squirted a dollop of lube on its tip. Remaining behind her, he crouched down and spread her ass cheeks with one hand. She stiffened, clenching as he tried to ease the slender phallus into her ass.
“Relax,” he commanded. “Stop resisting. That’s grounds for punishment.”
“I’m sorry, Sir,” she gasped, twisting away. “I-I don’t like butt plugs.”
“I’m aware of that, but this isn’t about what you like. It’s about what pleases your trainer.” At her anxious expression, he took pity, adding gently, “It’s not a butt plug. It’s just a small dildo, easy as pie to accommodate.” He smiled to soften his words. “Now, stop jerking around and stand still.” He gave her ass a sharp smack to punctuate his point.
“Ouch,” Skylar yelped, not very convincingly, but at least she stopped resisting him.
He continued to push gently until her body accepted the length of it. “There you go,” he said, pleased. “Now the harness to keep everything in place.”
The nylon harnesses had been custom-made for Desire Island. Machine washable, they looked something like a sumo wrestler’s costume, with a strap that was positioned between the legs and attached to a waistband that Velcroed easily into place. He slipped the harness into position and adjusted the strap around her waist.
Taking a step back, he picked up the dual remote and started the vibrators whirring inside her. It didn’t take long for her to begin squirming, her chest rising and falling as the toys inside her did their jobs. Christ, she was a sexy woman.
When she started to pant, he said sharply, “Don’t come, Skylar. I don’t want you to come—not yet.”
“Yes, Sir,” she gasped, doing a cute little dance on her toes.
“I’ll give you a distraction,” he added, moving toward the back wall to select a whip. If she were a novice to the scene, he’d have chosen a flogger, but Skylar had indicated during the vetting process that she was comfortable with fairly intense erotic pain, including whips, paddles and other impact gear.
Returning to the now trembling girl, he lowered the intensity of the vibrations with the remote and held up the whip, a deliciously wicked single tail with a nice little cracker on its end. Her eyes widened as she took it in.
“I’m going to whip your ass to help distract you from what’s happening inside you,” he said. “Ten strokes. You will count for me. Do you understand?”
“Yes, Sir,” she said breathlessly. Her cheeks were flushed, her lovely green eyes bright, her body still trembling.
Taking up a stance behind her, he snapped his wrist, letting the throw arc and crack against her small, rounded ass.
“One,” she squeaked, an octave higher than her normal speaking voice.
A lovely pink line appeared on her right cheek. Sadistic pleasure coursed through Caelan’s veins at the sight. He struck again, adding a symmetrical line on the other side.
“Two,” she cried.
He watched her carefully, gauging her responses as the whipping continued. She managed to call out each stroke. The sharp sting of the lash, which would have nullified the pleasure of the dildos for a vanilla person, was having precisely the effect he’d hoped for in this sub girl.
Her nipples were engorged, her skin flushed, her pupils dilated, her breath a sexy pant. Her face twisted with genuine pain with each cracking stroke, but he could see that her masochistic, submissive brain was processing it as erotic pain, which was its own kind of dark, perfect pleasure.
She was doing so well. He was genuinely impressed when she shouted out, “Nine.”
For the final stroke, he turned up the vibration speed on the dildos until she was quivering, her skin sheened in sweat as she valiantly tried to stave off her orgasm. Taking pity on her, he delivered the last stroke.
“Fuck,” she shouted, in place of the final number. Her eyelids fluttered shut, her hands clenching into fists as her body was wracked with what was very clearly a powerful, extended climax. She mewled and moaned as the orgasm hurtled through her, finally sagging heavily against the cuffs.