Losing the Bet Pt. 02

I needed to get rid of the slime or stroke my dick, one of the two as I gathered strength in my arms. A jolting shock coursed through my body, originating from the fluffy handcuffs. It rendered my ability to flex by forcing my muscles to spasm out. Rachel chose to respond to my frantic murmuring as a means to enlighten me on the next item on the list.

"The moment the handcuffs detect any pressure, an appropriate level of conditioning is administered." Rachel mounted herself on top of my legs just below my genitals to get a full view of her work.

"I wonder if it will train you not to resist." Her hands began to gently caress my thighs and every piece of sensitive skin around my private parts. It was a shift from her normal rough treatment.

I tried pulling again, ignoring her out of frustration only to be shocked into submission upon the tenth occurrence. I stared down worryingly at my penis and the slime, it wasn't my imagination that the head of my cock was swelling up like a balloon. All it took was a simple puff of air to hit it the wrong way for my nerve endings to scream in a bundle of pain and joy. The jelly had somehow allowed air to pass through even though it clearly covered my penis.

Rachel aimed her head downward at my swollen boner ready to do just that, exhaling a puff of air straight to the tip. An agonizing pulse to cum overwhelmed me as nothing decided to blast out. I wasn't sure if I shot a blank or if it was a false alarm, all I knew was the feeling kept returning every second with a more intense backed-up ache each time.

"Oh, I forgot to mention the inability to cum. It'll make tormenting you so much fun." She continued to blow on my swollen tip, taking in the amusement of every squirm and reconditioning I went through from struggling. I quickly lost count of how many times I tried to defy the slutty handcuffs. Under normal circumstances, they appeared cheap, brittle enough to snap like a twig from the slightest tug.

She really meant it when she said conditioning though as it wasn't randomly priming a shock each instance I tried to break free. It adjusted based on the frequency and strength behind my attempts. The moment it began to peak felt extremely uncomfortable, to the point of having a controlled seizure. Spasming that only ended the instant I proceeded to give up.

"Time for round two." Rachel slid her leg over to get under me, lifting my legs up and over, suspended above my head. My legs were lifted and balanced through the pressure she was putting on my rear and my upper back digging into the bed. I realized what she was trying to do as the pink strap-on aligned with my sticky bottom.

She was ready to take the most dominant position with me. The piledriver, the effect it had was the appearance and feeling of being fucked, without any control whatsoever to the tempo of the sex.

"I think your asshole should be nice and tight by now." Her thumb inserted after wiggling its way in against the leftover sticky lubrication. It acted like a glue that wanted to mend my asshole shut. "Perfect, it worked like a charm." It sounded like the lubrication's secondary purpose was a success. Not only did it make things feel amazing and loose at the beginning but it also closed up and tightened my anal walls to get rid of any unwanted gaping.

"I'll have you begging for more by the end of this little session." She made eye contact making sure her words were clearly heard. "I won't have to use a silly wager to open up that boy pussy of yours in the future." My eyes went wide and my tongue lulled against my lips at the edge of the gag ring from her sudden impalement.

She rammed it in, in one swift thrust, and a battle of letting her pull out ensued. My ass ended up being too tight, not allowing her to pull away. This only caused her to use more strength in her legs as it felt like she pried it out of my ass. Only to send it home again, in long steady jabs.

Her pace picked up, coming to a crescendo, timed with my shivering thighs. She knew that meant I'd cum and choose to activate the strap-on's knot as a finisher. It helped us stay locked together as she leaned over to kiss me on the cheek, tugging at my rectum from the angle.

The kiss was gentle and brief as she took advantage of the knots hold, rolling me over to my back. I grunted out all of the leftover drool as my face dug into the bed covers. "It's almost twenty minutes into our bet." She was checking the timer on my watch and it felt unreal with how little time had passed so far. I was only two-thirds of the way there and I already wanted to admit defeat.

I would have cummed twice over if it wasn't for the slime. I couldn't even plead for her to let me cum with the gag stuck in my mouth, much less lose the bet by begging her to touch my cock.

She handled me roughly and spun me back around onto my backside, my ass floating in air unintentionally by the knot's support. I was moaning, trying to get her attention, only to be ignored as her hand scooped up the container holding the neutralizing agent.

"Let's play a little game, since you're so willing." She treated my desperate moans for attention as excitement. "If you can catch your load in your mouth, I'll consider removing the gag." She didn't bother waiting and already placed me into the previous embarrassing position. It gave me a perfect view of my erection and her entire figure from her domineering thighs to her loose strands of hair that escaped her bundled hairdo.

I watched in anticipation as she poured a similar dollop of the darker shade of slime onto my swollen tip. It acted even faster, instantaneously returning my soft head to its proper size, no longer blocked from release or sensitive as hell. The simple thought of having the ability to cum had caused precum to ooze out.

"Well, aren't you in a rush to eat your own cum." Rachel returned mockingly after setting aside the closed container. "Do you want me to fuck your pussy some more?" I nodded, having lost my dignity altogether.

"Are you my good little slut?" She slapped my asscheek, only continuing after a vigorous nod on my end. "You actually wanted to lose on purpose didn't you?"

A loud and painful slap was the last thing I remembered as my mind muddied its way through her orgasmic fucking. My one goal and desire between shaky eyelids was aligning my mouth to catch cum. It only took a handful of thrusts to send my jizz spraying all over my face, with more than half of it landing dead center onto my tongue.

I had no control over swallowing because of the gag, which caused it to pool together with my saliva. It was at that moment the ring gag began to shrink and detach itself from my inner mouth. A prompt grab from Rachel stopped me from spitting all the contents within my mouth out, removing just the accursed gag from my sore jawline. "Swallow it for me sissy." There was no second-guessing to her command as I shut my mouth and swallowed to relax my jaw.

I'd finally gotten a breather as her dildo plopped out of my ass, with the same sticky substance sealing my rectum back up. I opened my eyes to see my erection still stiff as a diamond, even causing a jolt from the handcuffs from my instinct to touch it.

"You'll remain hard like that, until you let me touch your pathetic dick." I didn't even care at this point and forgot all about the deal, what deal?

"Please, touch it!" To that, Rachel responded with her cute yet frightening giggling.

"What exactly did you want me to do?" She prolonged my anguish by forcing me to repeat myself.

"Please, stroke my pathetic dick. You win, mistress!" I even added in a title for her and that seemed to please her from the smile she returned.

"Good boy." Her gloved hands felt rubbery upon contact, and now that the bet was over her eyes radiated into a sky-blue glow. It was like those gloves were specially made with her magic in mind.

Instead of hurting from the immense friction, the speed at which she stroked my rod was incomprehensible. I wondered if it was a personal quirk of hers that made her want to turn me into a quick shooter. This time, I didn't even last the twenty seconds I had from her blowjob. It only took a matter of seconds before a stream of jizz leaked out and she let go. I came so many times in such a short time that my penis had lost its ability to shoot projectiles.

It only managed to leak onto her gloved hands, intertwining around her fingers. She raised a cum coated finger to my lips and waited for me to open up willingly. There wasn't a single command or order, only the basic desire to please her.

"That's my good cumslut." She took her time making sure I slurped down each of her covered digits.

My throbbing erection found satisfaction, going limp from pure exhaustion. I ended up resting my eyes and thinking about how I never once got to touch Rachel in a sexual way, or even see her naked. The closest thing I received, that felt earned was a kiss on the cheek from her intense fucking.

I was beginning to doze off until a constant tugging on my spent member occurred. I didn't have the energy to open my eyes and look down, letting her continue whatever it was she wanted to do.

"There!" With an audible snap and click, Rachel grabbed my attention by slapping my thigh. "Maybe this ought of help with your premature ejaculation." It was a groggy process, returning to reality as I rolled over to my side, even getting her assistance to help me sit up.

I saw it staring back at me from my cross-legged position, a pink transparent chastity cage. The size of the cage fitted against my limp dick like it was custom-made. I already knew out of all the items she had used on me, none of them were what they seemed and her next sentence as if she read my mind proved me right.

"This special little toy automatically adjusts to the wearer's size." She held back from teasing surprisingly, and kept a passive tone, affixing a key into a necklace to place my chastity on for display. "It will only ever grow smaller, turning you into my perfect buttslut. You won't be needing that during your stay here." She giggled during her explanation, from the sudden live demonstration of the chastity device shrinking to match my still fading erection.

"You won't notice it's even there after a while. Your pecker will get so small it might as well be a clit." I was now afraid of not having an erection at all times. I didn't want to lose against a chastity cage, as long as I kept my penis from going too limp, things would be alright. It was silly of me to even think that was a possible remedy, as it would be impossible to be conscious of it at all times.

"Now that item number one is out of the way, I can introduce you to the other three." Rachel picked up the original jelly container. "You've already experienced this number, so there's no need to explain it."

The thought of her approaching me with that stuff caused me to pull away, in turn sending another jolt of shock from the handcuffs. It was like a chain reaction that aided further in the chastity's tightening ensnare.

"Isn't that a little too extreme?" I could no longer fight her and everything she did felt outlandish in a manner of speaking.

"It won't be going on your penis, that would be counterproductive." I remembered her stating it would be used on my nipples and that calmed my heart if only slightly.

She held me down with an arm to keep me steady as she poured a droplet onto each nipple. The slime-like jelly immediately spread to cover the entire surface of my nipple. Just like before, it took a moment to activate, causing my nipples to perk like they were bare on a cold winter's night. They didn't stop there as each one became swollen, growing to the size of grapes. The swelling and pleasure that it was exerting forced my erection to go stiff inside the cage, not able to expand beyond the forced and set limit.

Thankfully, the swelling seemed to settle at a slightly smaller size or else others would be able to easily see my nipples poking through my clothes. "They're sooo cute!" Rachel blew a puff of air towards both of them, only making the pain along my groin tighter.

"Stop it." I avoided activating the handcuffs and calmly moved away from her lips. Rachel responded with a head shake and laughter, moving on to the next item.

"This one's my favorite." She held some kind of anal toy up for display. "There's no point explaining, you'll just have to try it out, to fully understand. Now spread that boy-pussy for me."

I was laid back down on my arms and lifted my legs into the air to grant her access to my anus. I didn't know what to think of the item, its size was not much bigger than a marble. With the amount of gapping she made me experience, something this small wouldn't even be noticeable.

My ass easily devoured it as she stuck it in. "Think of it as an all-in-one anal plug." I squinted my eyes with curiosity, unsure of what to expect.

"Ahh!" Catching me off guard, the marble-sized toy expanded to the size of a fist, even changing its shape to fill out my hole. A strange numbing sensation targeted my prostate gland.

"That's the look I wanted to see. I bet you're feeling it by now." Rachel continued, "All it will take is for someone to say the set command and you'll be leaking from your clit." A wide grin returned to her lips.

"It won't work if you say it though." She alluded to the keyword, lengthening the suspense for all its worth. "You'll no longer be in control of when you cum." The instant she uttered the syllable cum, an activation sequence fired off on my prostate. The feeling was like a subtle static shock that desired to juice my dick of all its seed.

"See..., you don't have to worry about the cum making a mess inside your cage." She jested to the slit for urine and sperm to pass through as her mention of the keyword made me shudder another ooze of sperm to drip out.

"Come here and I'll tell you a way to deactivate it, so that the phrase cum won't work." I instantly shivered in surprise from her telling me to come over, since that also acted as the keyword. My prostate ejaculation was beginning to shoot out less and less sperm, becoming more of a translucent liquid.

"Would you look at that, even cumming like a girl too." It even worked for every form of the word as I hurried over to the spot she wanted me in, to get her to stop.

"The secret to deactivating it, is to eat your own cum that leaks out." Rachel made sure to specifically say the keyword every time, which made me realize eating my own cum wasn't too bad of a deal considering she had already made me eat my own filth several times throughout our session.

"Going to lap up that cum or do you enjoy it when I make you cum like the useless cumslut you are." I managed to lap down my seed just before her last keyphrase was uttered.

"Good boy, as you can see you aren't cumming anymore." I drew a long breath of relief as she carried on. "It won't be much help out in public, but it serves its purpose of turning you into my cum loving slut." I focused on her word cum and again nothing happened. I was trying to understand what she meant, and why it wouldn't be helpful out in public.

"Anyways, moving onto the last item." She picked up and reached behind me to attach a thin metal bracelet to my left wrist. It felt pretty flimsy like it would break if I hit it against something wrong. I looked back up to her and saw her eyes glowing sky-blue in focus, channeling her magic into the bracelet.

"This will make sure you're being honest with that buttplug of yours and enable you to take it out to use the restroom. All you have to do is think about wanting it out and it will release from your asshole." Her eyes finished their glow and the bracelet shrunk tight like a part of my skin. There was no way it was coming off unless I wanted to sever my hand.

"It will provide you an allotted five minutes to reinsert the buttplug, before enacting a consequence." She sounded all business as she explained the procedures. "You really don't want to experience the consequences." Her hands worked to undo the handcuffs, setting my wrists free.

"It is synced up to each item and will initiate its punishment on the chastity cage." Rachel finally slowed down and took a breather. "Think of the handcuffs but many times worse and with the added bonus of squeezing. And remember it never grows any looser." I didn't want to even imagine the punishment and made sure I wouldn't dally on the toilet.

"That's everything... What do you think, cumslut?" I was interrupted from any response by the activation of the anal plug. It jolted my prostate into shooting out clear fluids.

"Why is it happening again?! I thought you said it deactivates from eating my own cum." My thighs were shuddering from the effect, confused about why the buttplug reactivated on its own.

"Oh, did I forget to mention, eating your cum only disables it from making you cum again for the next thirty seconds?" I was already scooping up the leaky liquid into my mouth, anticipating her abuse of the keyword. I now understood what she meant by this not being able to help while out in public. There's no way I'd be blatantly eating my jizz every thirty seconds at worst.

A familiar beeping ended the silence as my watch's timer of thirty minutes had just been reached. She bellowed into laughter so hard from the awkward timing. I on the other hand contemplated the kind of situation things had turned into. I was already dolled up from head to toe with sex toys, under complete submission by someone I only met today.

I couldn't even last thirty seconds from a blowjob in our first deal and the second try around I was already decked out in her gear well before the timer met its end. I never thought it would turn out to be so very one-sided, who the heck was this woman. I saw that she was beginning to speak again after recovering from catching her breath.

"We've got a little less than thirty minutes left. I believe it's time for round three." Rachel showed me one final thirsty grin. "Don't worry..., I'll disable the buttplug until I'm finished with you." That was the start of my growing relationship with my new mistress Rachel.