Losing The Bet Pt 02

"Wonderful looks like you understand rule number one." Rachel smirked. "Now, we only have an hour, get in there and get undressed. I've got to grab a few things from my place." She pointed a finger to the master bedroom of this suite. I was filled with meek curiosity for what she had in store for me, to have to retrieve some belongings before we got started.

"By the time I've returned and you're not undressed and on all fours on top of the bed, ready with your ass up in the air, then you'll be in for a punishment." She wore that wicked smile, the same one she showed me just before I lost our bet. Knowing her, she was going to use her speed magic to hurry back.

I didn't wait for her to leave before scrambling almost on all fours, in a frenzy to reach the master bedroom all while attempting to undress along the way. The king-sized bed was in sight with white sheets set with too many plush pillows to count. The sound of a small cloth-like duffle bag hit the floor with the contents rattling from the abrupt fall. My knee made contact with the bed as I moved to get the rest of my body into position.

"What did I tell you?" I already knew I lost the moment the pink tote bag hit the wood floor. Her voice only added to the sense of dread on her coming punishment.

"Looks like I'll be using everything I've brought along." I finally caught a glimpse of her after peeling my eyes off of the bag. Rachel changed outfits from her sleek blouse and business attire to a provocative corset. It matched the black fishnet stockings that ran all the way up to her thighs and the rubbery gloves that ended just before the elbows. She even took the time to apply some make-up and place her hair into an extravagant bundle. It was like she had a whole thirty minutes to get ready.

I opened my mouth, about to ask how out of pure shock then snapped my jaw shut at nearly making my situation worse. Instead, choosing to turn around and sitting on the edge of the bed to face her properly.

"Can't you see how much effort I put into our time together?" She flourished from my internal struggle. "You can't even manage to prepare yourself on the bed for me properly." Having clicked her tongue at the end, she bent over to retrieve the pink tote bag from the floor. Doing so in an unnaturally slow and tantalizing manner, presenting the perfect view of her gorgeous bubble-butt.

"You may talk until told to be quiet, but under no circumstances will you ever interrupt me. Okay?" She finished with such a cheery okay as if to mask her threat. The bag was being held up by the drawstrings with one hand until she pried it open, retrieving a single item.

It went the entire length of the tote bag, a hard and rubbery slab of meat that slapped against her thigh from its sheer weight. Roughly several inches larger than mine when fully erect and hot pink like the tote bag. I considered myself well-endowed at seven inches yet the girth was a major difference. The entire length had the thickness of a tennis ball, only easing up into a phallic shape at the tip.

"You're crazy. That's way too big!" I already knew from her twisted personality where things were headed, even Alexa never used one that big on me yet. She wasn't finished and pulled out an attachment harness for the pink dildo. A black and pink strap-on set.

"Just as I thought, this isn't new to you. Let me guess..." Rachel giggled, putting a finger to her chin. "A slave of yours has already beat me to it, showing you the joys of being a sissy-slut?" Her assumption was shockingly accurate, almost like she wouldn't be acting this way unless she had a really strong hunch in the first place.

"Great, then I wasn't wrong to pack the larger one." She accepted my silence as a confirmation. "Don't think I'll be as easy on you as your slave though. You'll be begging to be mine before I'm done with you." She reminded me of the punishment for not getting ready on the bed quick enough.

"I want you to put together the strap-on harness, make sure it's nice and tight around my hips." She didn't offer me any eye contact and it sounded more like a command as she was busy pulling out the next item.

"There's more?" I couldn't hide the tinge of arousal that continued to build up. My hands were deftly putting together her strap-on and securing it tightly to her waist. I can't remember how many times Alexa had forced me to do the exact same, so it came to me pretty naturally.

"Much more, would you like to make another deal?" On the bed laid a chastity cage, followed by a ring-shaped mouth gag sitting on her open palm. "Of course that won't get you out of your punishment or the next fifty-five minutes." There seemed to be even more things she kept hidden inside of the tote bag as she tilted her head to me for a reply.

"Is there a reason to indulge another one of your deals?" I asked, already half beaten from how well the first one turned out.

"I'll become one of your slaves, seal and all." Rachel licked her lips, adding on an additional bonus. "I won't use magic as I did earlier."

The thought of her becoming my slave meant I could have my way with her any way I wanted, at any time of the day. Her behavior in bed matched Alexa's to a tee. My mind was stuck on the prospect of having a threesome with her and Alexa, night after night. Knowing both of them, they'd hit it off and explore the many ways to tickle my growing fetish for wanting to be under their thumb. My boner became rock hard from the prospect and caused a downward glance from Rachel.

"Well, isn't he quick to agree?" She laughed.

"I won't become your slave in return, so that's off the table." I immediately placed my foot down, there were too many obligations and goals that I needed to fulfill. I wasn't going to let a slave seal be placed on me.

"Nothing of the sort." Rachel carried on with the contents of the wager. "You'll just need to wear these things throughout the entire stay here, even during your event fights in the arena." She poured the rest of the items onto the sheets, using her magic to place the ones she meant together, isolated from the rest as a means to not waste any more time.

I only recognized the chastity device and the oddly shaped anal plug. The other two were a mystery, one being a tiny plastic see-through container the size of a teacup. Inside of it was some kind of viscous jelly that also looked somewhat transparent. The last object was a thin silver bracelet.

"What are those two for?" I pointed at the bracelet and the little container, somewhat afraid of her answer.

"Think of this as sticky cream that stimulates anything it is applied to, because of its jelly-like consistency it won't disappear until my mana signature deactivates it. " I felt like she was skimming the details for the jelly, though remained quiet to hear her continue. "And this will make sure you don't cheat with the butt-plug or any of the other items for that matter." She used two fingers to place the bracelet on display, wiggling it in the air for me to inspect.

I mulled over the four items and the image of me wearing them at the same time unintentionally shot into my brain. I figured the bracelet was a set piece for the anal plug, on the occasions I had to relieve myself in the bathroom. Most likely with some built-in way to coerce me to place it back in, once cleaned up.

"And the conditions?" I said with a voice full of concern.

"As long as you don't cum three times within the next thirty minutes." Rachel added on. "I won't be using my magic nor will I be touching your penis at all." She reminded me about the no magic clause on her end. Thinking about lasting thirty minutes had my eyes drifting to the enormous pink strap-on. There was no way I'd be able to win against that beast, and she added in another condition as if reading my thoughts.

"In addition, you also win if I cannot get you to beg for me to touch your penis within the timeframe." The deal sounded much more plausible and in my favor after she added in the begging part. As long as I maintained my willpower she would be my new slave after this session.

"What more is there to lose, I won't let you win this time." I felt more confident in this bet due to the fact that one of the winning conditions lied solely in my ability to keep myself together. All I needed to do was shut up and not say anything at all if push came to shove.

"It's a deal then, I'll be looking forward to being your handler from now on." Rachel said it in a way that she was sure to win, like her victory and my loss was inevitable.

"We won't be needing this for the time being." She picked up and placed the chastity cage along with several other items back into her risque tote bag. Like before I managed setting up a timer on my watch to track the allotted thirty-minute duration for our bet. It was the only article of clothing being worn on my body as I sat utterly in the nude on full display for her.

The moment I told her my watch was set, she wasted no time on her next step. I was staring at her full figure in the thigh-high stockings with the corset that accentuated her hips and cleavage. The long rubbery gloves were even a weird turn-on for me as they stuck to her like a second skin. The thing that felt out of place more than the ten-inch girthy strap-on was her innocent sky blue eyes. She had a face that made you think this was something she'd never be a part of much less instigate for it.

"You're not allowed to speak until allowed to from this point forward." Rachel adjusted the heft of her massive girl cock with a firm grip at the base. "Now back to your punishment. Get on all fours, ass high in the air!" She commanded the last bit, to startle me into hurrying up.

I repositioned to the spot she pointed to and stretched my ass into the air like she wished, filling with embarrassment about the position she had me take. I held back the desire to tell her to stop delaying with her observations, but realized a bit too late that she was already prepping for entry.

"Let's hope for your sake, there's still some saliva that hasn't dried up." Rachel slapped the dildo down onto an asscheek as she positioned herself above me. "You can only blame yourself for taking too long to decide earlier." Following the slap, the pressure of the phallic tip was being prodded into my hole.

I bit down on my lips in terror for the fact that I knew none of the saliva lapped onto the massive dildo was no longer remaining. That didn't stop her from missing her next beat, and with a firm handle on the sides of my waist, she went to town.

The burning sensation of my asshole tearing up and the rehealing thanks to my regenerative powers avoided a bloodbath. My eyes were tearing from the sudden pain of being plowed open. I could no longer handle the pain as she went back and forth at pushing in and out.

"Stop!" I yelled. "At least use some lube!" I managed to say through broken speech and even pushed away, forcing the dildo to fall out of me. The exit left my rear stinging and contracting tightly like it never wanted to be opened again.

"You may be right..." Rachel held a bemused grin. "I told you not to speak though didn't I?" Instead of moving closer to me, she scooped up the strapless O-shaped ring gag.

"Since you can't manage to keep your mouth shut, might as well help you keep it open." Her tone went serious like she was genuinely scolding me for failing rule one.

"Open!" Her firm tone had me doing exactly that. An opened mouth as far as my jaw was comfortable with maintaining. It was more than enough for the small ring gag, until she placed it inside of my mouth. The ring gag turned alive like it knew it was ready for use, conforming to every minute contour of my inner mouth. Eventually expanding to the size that would easily allow for a tennis ball to pass through and also making sure I couldn't flip it horizontally to defeat its purpose.

I wanted to shout no magic allowed but only muffled sounds and drool came forth. "I know what you're probably trying to say and no, I haven't used any of my magic. It's all stored within the item itself." I swore internally at her method to bypass the no magic clause, thinking about each item and their possibilities in a whole different light, now that she nudged to their magical properties.

"This is the outcome for disobeying a simple rule." She didn't even try to hold back her giggling. "Now as you mentioned, lube..." Having said that she stuck the fat dildo into my mouth without any forewarning. The ring gag turned my mouth into the perfect sleeve for her strap-on, gagging up saliva and drool along the entire length.

I'd rather endure this pain to ensure her pink strap-on was thoroughly lubricated for my rear. My head reeled back whenever she plunged it to the base, the feeling of the leather harness pressing against my lips as I felt it halfway down my throat. I was forced into holding my breath without any leeway to relax until she decided it was good enough to carry on with assaulting my butthole.

The ring gag provided no room for purchase even long after the strap-on left my mouth. I was stuck mouth wide open waiting for dental work to never happen and left drooling against my will.

"You can talk all you want, now that your mouths wide open." She teased me on the fact that I couldn't properly speak even if I wanted to, other than strained moaning. She even timed her sentence to the reacquaintance of her pink strap-on, making sure to evoke a loud and guttural response from me.

I was playing to her tune with moans that grew louder with each consecutive thrust, each harder and faster than the last. It was already that time, I was surprised it hadn't happened sooner with the rate of her thrusts. My prostate relented to the overstimulation and my dangling, pathetic definition of a limp penis squirted a copious stream of cum. All of it jetted onto the white sheets below like it was trying to hide its embarrassment through means of camouflaging with the sheets.

"Poor little thing, cumming like the sissy you are. How does it feel to orgasm from your pussy?" Rachel whispered in a seductive tone, not even bothering to keep count of my first ejaculation.

"Let's make it a back-to-back orgasm like a real pussy." She began slapping my butt cheeks, picking up her pace. I ended up feeding her high with the gurgling response of drool that tried to say otherwise. It only caused her to sway and thrust deeper, along with a slew of mental barrages.

"You're enjoying being my little bottom bitch, aren't you?" She posed questions in a yes or no format, in a way I could respond with grunts and moans. I vehemently opposed her jabs, but gradually fell deeper into her mind fuck.

"We both know if you really wanted to, you could overpower me." She switched to mocking me for the situation I found myself in. "I hope you aren't using our deal as an excuse to say you don't actually enjoy this..." That was enough to send my flaccid member roping with jizz, adding on to the pile pooling on the sheets.

In a moment of clarity, I thought back about her last statement. There was absolutely nothing preventing me from reneging on our deal except for some damaged pride. She was right that I could hold my own against her if need be, and in my struggle to escape this situation I decided to act on it. The feeling in my legs was weaker than I imagined when I tried to extract myself from her continued thrust.

"Who said I'd make it easy for you to go back on our deal?" I was losing out to her powerful thrusts and the tight grip she held onto my lower thighs and waist. If only it was those two things that prevented me from backing away then I'd have managed without much issue. The lingering premonition going back to magical items had surfaced with the sudden shape altering of the thing exploring deep inside my anal cavity.

"You won't be able to pull away from a knot." I turned my head back to see the maniacal sneer plastered on her face. The bulging expansion of the dildo's base secured itself beyond my sphincter, unable to come out no matter the amount of pulling, less I end up completely broken. It was something I couldn't come to terms with even if my regenerative powers could handle it.

It didn't end there though and another feature came forth, just when I thought her thrusting couldn't continue anymore due to the sheer size in my ass. Her thrusting remained unhindered by an auto lubricating substance lathering the inside of my rectal walls. "Neat, isn't it?" Rachel panted. "Self-lubricating and it even amplifies your nerve endings, to increase pleasure." I didn't miss the fact that she made me experience a no lube entry at the start when it had lube built-in all this time.

My eyes were becoming crossed as more and more drool escaped down the sides of my cheek and chin. I was losing the strength to keep it together and in that moment of weakness, the sensation of another orgasm arrived. My third one in a span of time I wished to keep secret and never be found out. An apparent puddle of cum was laying below my stomach, no longer able to hide on the white sheets from the squirming consistency.

The magic within the strap-on deactivated and with a final slap and push did she let me fall to my side, leaving me to fester beside my own jizz. She could tell I'd lost most of my fight and wouldn't be able to run off from the way she made sure to gape my poor bottom. I could feel the lubrication inside turning into a sticky substance that acted as the only means to close the circular void that was left in the strap-on's absent wake.

Before I had the strength to act on, she seized the opportunity to cuff my hands behind my back. I hardly would have noticed if it weren't for the fluffy fur that tightened against my wrists. I was still lost in a stupor to react, only aware of the sound of her moving behind me.

"There's only one condition remaining, the one where I make you beg for me to touch your pathetic and limp penis." The pain throughout all of that prevented me from actually getting hard like I normally would from domination play. Other than a means of shooting out my sticky load, she was right, that it was pathetically limp.

"On your back." She rolled me over with my hands being laid on, though not really in any discomfort due to the plushness of the bed. "This will have you begging in no time." Coming into view was her perky cleavage or at least that was the path my eyes followed, down to the thing she had in her hands.

It was the clear, tiny container of jelly she went over earlier, something to do with being sticky and feeling good. It sounded like the lube that was currently pervading the insides of my rear. The deal was under the premise of not touching my penis at all, so I couldn't think of how it would help her.

"Just a smidge should do." She held it directly over my penis, tipping the container to let some of it slowly pour out. The consistency wasn't as thick as it seemed and a dollop-sized portion landed expertly onto the tip of my urethra.

I soon found out it had nothing at all in comparison to the lube as it moved with a mind of its own like some form of slime. Changing its consistency into a stretchy and sticky jelly, engulfing my entire head as if to suffocate it.

"It takes about twenty seconds to come into effect. The only way to stop it is with the neutralizing agent." Rachel had already closed and set aside the container to pick up another one she described as the neutralizing agent. The only difference I could tell was the dark shade of slime that was inside of it.

There was no longer a drooling problem with the gag ring now that I was on my back, but it allowed me to whimper to a greater degree. I was beginning to feel the effects of the slime with my boner growing to full mast. If my rock-hard erection wasn't enough, it was combined with a tingling itch that wanted to be tended to. It only became stronger, and my desire to break the handcuffs became a top priority.