Chapter 7
His Cocky Challenge
Race to the finish
The Headmaster addresses the other students. “After kissing and a little explorative touching, the couple would then move on to manually stimulating each other.”
I hold my breath as he begins lightly playing with my nipples before reaching between my legs. I swear, I feel like I’m a teenager again, fooling around with my first boyfriend!
My pussy gushes with excitement when Headmaster Wallace commands, “Touch me, skye.”
Biting my bottom lip, I slowly reach out to wrap my hand around the Headmaster’s hard shaft. I unconsciously let out a little squeak when I grasp it and begin moving my hand up and down.
“Very nice,” he murmurs encouragingly.
I can hardly believe I’m stroking the Headmaster’s cock, while his fingers tease my wet and willing pussy.
“And if the two are feeling especially adventurous, they might even engage in stimulating each other orally at the same time…”
Headmaster Wallace disengages from me to reposition his body so his head is dangerously close to my clit and his raging hard-on is in line with my lips. Turning his head to look at the audience, he asks, “How many of you have done this?”
Every one of my classmates raises their hand except for Michelle, who looks a little embarrassed.
Headmaster Wallace turns those blue eyes back on me. “Shall we indulge ourselves, skye?”
Never in a million years could I have imagined I would be sixty-nining the Headmaster of the Submissive Training Center. The only thought in my head as I open my lips to take his cock into my mouth is, I hope I’m actually good at this.
I have flashbacks to my vanilla partners begging for more while I eagerly sucked them. But their enthusiasm for my skillful fellatio contrasted sharply with the feeling of boredom I experienced while cheering on those same men’s pitiful attempts to eat my pussy.
I’m suddenly overwhelmed with a horrifying thought!
Is it possible my partners were just being “nice” to avoid hurting my feelings, the way I covered for them?
I might actually suck at this, and I know my skills cannot compare to a real submissive’s…
I moan loudly as I take his cock into my mouth, hoping to distract him with my enthusiasm to make up for any oral skills I may lack. And then I remember our lesson tonight! I’ve been given the keys; all I need to do is unlock everything I’ve learned.
When he presses his tongue against my pussy and gives my clit the lightest of fluttering licks, I momentarily lose my mind. I have no idea what magic this man possesses, but my body instantly responds, and I cry out in pleasure.
Before I can wow him with my newfound knowledge, he switches gears.
Pulling his mouth away, he turns back to the class while swiping my juices from his mouth. “This is as far as most vanilla couples will go.”
Then he chuckles and looks down at me—with his cock still in my mouth. “But we’re not vanilla, are we, skye?”
When I let go of the suction, his cock pops out of my mouth. “We are not, Faelan.” Now, the Headmaster has me more curious than ever!
He lies back down on the table and faces upward, commanding, “Lie on top of me.”
I feel a moment of hesitation, afraid that I might crush him under my weight. But he pulls me onto him, and I lie there looking down at the handsome Headmaster. Staring at his lips so close to mine, I’m sorely tempted to kiss him.
But as a good submissive, I valiantly resist the urge.
Looking up at me, Headmaster Wallace’s smile grows wider. “Perhaps you are wondering what this position has to do with oral pleasures.”
I giggle when I answer. “Honestly? Yes.”
“Then let me show you,” he states with a youthful enthusiasm I find charming in a man older than me. Reaching around my back, he reattaches the harness to the chain above.
“Are you ready?”
I stare at him in disbelief, and my heart starts to race when I realize that I’m about to be lifted into the air.
When he notices my hesitation, he assures me, “This harness is designed to support the female body comfortably.”
“But I’m too…”
Before I can say “heavy” he presses his finger to my lips. “You’re perfect, skye.”
I frown when he takes his finger away and insist, “This won’t work for someone like me.”
“It will,” he states emphatically.
Unconvinced, I whisper, “I’d be afraid of falling, and…hurting you.”
“The equipment will not fail.” He looks at me with compassion and explains, “You will be suspended only a few inches above me, and we will be touching the entire time. There is nothing to fear.”
Last night, Tono Nosaka taught me how powerful connection is during a scene. Knowing that Faelan will remain connected to me through touch does help to calm my fears—somewhat.
“Is there an issue?” Dono Marcelo asks from the seats.
When we both turn to look at him, my throat closes up.
Headmaster Wallace returns his attention to me and waits patiently for my answer.
After last night with Tono Nosaka, I feel freer than I have in a long time. I trusted a stranger last night and feel compelled to trust this man who has been training me.
I hesitate for a moment before answering, “There is no issue, Dono Marcelo.”
“Very well,” Dono Marcelo replies in a curt tone. Even though I know the trainer doesn’t think highly of me after I failed to call my safeword and had a total meltdown on stage, I appreciate that he is still looking out for my well-being by checking in.
I meet the Headmaster’s gaze and tell him, “I trust you.”
“I will honor that trust,” he replies solemnly, then adds with a grin, “And now for some magic.”
First, I hear him snap his finger, then I let out a gasp as I feel the pressure from the harness as it slowly lifts me into the air. But the weight of my body is so evenly distributed by the leather harness that I experience no painful pressure points.
Headmaster Wallace caresses my cheek while retaining physical contact with me—just as he promised. After a few moments, I am lifted a couple of more inches above him. When the suspension stops, I smile down at him as I watch my hair tickling his face.
“Color?” he asks with a gleam in his eye.
“Green, Faelan.” I feel a fluttering in my stomach when I call him by that title.
“Excellent.”
Turning his head to face the others, he says with a smirk, “The BDSM couple has much higher aspirations when it comes to oral sex.”
Looking back up at me, he asks in a husky tone, “Are you ready to take sixty-nine to a whole new level?”
I finally understand the reason for my suspension and break into a smile when he slowly turns my body around so that I am hovering just inches over his hard shaft.
“Now for the challenge,” he states. “Who can make who come first?”
I realize I’m at a distinct disadvantage as a newbie sub when going up against an experienced Dom. Normally, I would concentrate all of my attention on sliding my lips up and down his shaft. But based on what I’ve learned tonight, the shaft is the least sensitive part.
Thinking back on my lesson, I grasp his shaft firmly in my hand and wrap my lips around the head of his cock. Instead of immediately bopping up and down on it, I swirl my tongue around the ridge, which I now know is the corona. I’m met with a low grunt that tells me I have made the right decision.
I’m excited about this challenge! I feel enchantingly light in the harness as I hang above him—free of the constraints of gravity.
But I become momentarily distracted when the Headmaster’s tongue starts that unusual fluttering on my clit.
My body responds immediately to the stimulation.
Not wanting to be outdone, I flick my tongue against the stringy frenulum on the underside of his cock and get an even deeper grunt from our Headmaster.
The two of us are serious about winning. He increases the suction of his mouth as he continues to tease my clit, sending waves after waves of pleasure through my body while I eagerly bob up and down on his cock before moving down to his balls.
I’ve never really played with a man’s balls before because I always assumed they were exceedingly sensitive. Taking one of them in my hand, I squeeze it gently while I lick the base of his cock and feel him shudder.
Returning my lips to the head of his cock, I continue to tease his balls. When I taste the Headmaster’s precome, I know that I am close to making him climax…but so is he.
I desperately try to stave off my climax as I ride the edge of a power orgasm, which continues to build in intensity. Goosebumps rise on my skin, and I know in that moment that I’m cooked. I’ve hit that point of no return.
Moaning loudly with his cock still in my mouth, I can’t stop the tidal wave once it crests.
In a glorious cry of defeat, I give into the delicious feelings he’s created.
My whole body begins to shake in the harness as I climax, and I feel his body tense before he comes in my mouth.
I’ve never experienced a simultaneous orgasm during oral sex and eagerly swallow his essence as my inner muscles contract in waves of pleasure.
I fucking swear his come tastes like the ocean…
As a final shudder courses through my body, I lie there limply in the harness with my eyes closed, completely satisfied.
I sigh with contentment when he slowly turns me in the air to face him again. Opening my eyes, I see the Headmaster looking incredibly sexy as he stares up at me with those ocean blue eyes. When he grins, I notice that his lips are wet with my juices when he says, “I’d call that a tie.”
I giggle softly above him and nod.
“You look beautiful up there, skye,” he murmurs.
I smile, feeling empowered and beautiful as I hang suspended above him.
As I’m lowered back onto the table, I notice Faelan’s playful demeanor transforms back into the more rigid role of our Headmaster, even as he helps me out of the harness.
Although I’m sad to see the change, I’m honored to have experienced this side of him.