Debra's Descent Ch. 16-24

Ch 16: The Bet 4/5 (G21, D29)

We got back to the hotel around 10:30 and gave the girls a few minutes to unwind and freshen up. We agreed to meet in the extra hotel room--342--that I got just for this Task.

Gary and I spent most of the hour having a few drinks in the bar and chatting to Miss Penny. I knew what my last Task was and had it set up in the room. But, Miss Penny was being very cagey about what her Task would be.

Miss Penny had a reputation for humiliating female subs. She liked to push new subs quickly and often had newbies going well past what they thought their limits were. Her online profile had hundreds of pics and videos of subs degrading themselves at her command and for her amusement.

Miss Penny's relationship status was vague. From chatting with her over the past few years, my guess was she was happily married to a vanilla guy who probably knew a bit about her interests. She only played with female subs, but had a wide circle of dominant friends. Subs saw it as a challenge and badge of honour to have at least one in person or virtual session with her--hence her huge photo collection.

Just before 11:30, the three of us made our way up to 342. The room had two king sized beds in it. On each nightstand was a massive bottle of lube with a press dispenser on the top. The bottles each had 2 litres of lube in them.

Laid out next to each bed, from small to huge were 30 objects all vaguely dildo shaped. Some were plugs, dildos or vibes while others were random objects, vegetables or fruit.

Next to each bed hung a matching pink silk robe embroidered with each girl's name.

At exactly 11:30, there was a knock at the door and Miss Penny let in the two subs who were again holding hands. Both girls had dressed in T-shirts and shorts.

Miss Penny introduced herself and handed each slave card four which they'd pretty much guessed at as they entered the room.

Task four was a stuffing competition. The girls had up to an hour to insert the largest object they could in their pussy and ass separately--then at the same time. Miss Penny would rule based on volume each girl stuffed inside herself and had a ruler and a cloth measuring tape for the job.

The rules allowed the girls to use smaller objects first before an official measurement. They also had to cum with the measurement object inside them. A few vibes were on the nightstand for that part.

Final measurements would be taken at 1am--but an earlier ending was acceptable. Miss Penny would measure any insertion the subs wanted, but only the largest would be counted.

The girls both stripped off and began looking at the huge selection before them.

Debbie immediately lubed up a medium sized butt plug and slipped it in. Gina copied her but used the largest butt plug available--a bulky 6". I wondered if Gina was more of an anal pro than my sub.

Both subs started with their pussy. Debbie fucked herself with a 10" dildo that was about 2" in diameter. Gina picked one a bit bigger around and slipped the butt plug out.

Debbie moved up a few sizes and managed to push a massive 3" diameter dildo into her. Gina moved on to a large squash that took her some effort and a lot of lube to get in even part way. Gina kept working at it, adding more lube, changing position from laying on the bed to squatting on the floor. Eventually, she got it in about 2/3 of the way.

Gina slipped out the squash and set it aside. She studied it compared to the other items available.

"You guys are evil not giving us an inflatable choice...I'd take something bigger if I could stretch out with that first." She kind of half laughed.

"Blame me for that one. Will was going to include some...but I knew that would make things easier," Miss Penny said, smiling evilly.

Gina picked up the third largest dildo--a real monster that was shaped more like a giant butt plug than a cock, but less bulbous in the middle. It had a suction cup base, so she stepped into the bathroom and stuck it to the tiled floor.

She kneeled next to it and slathered a huge amount of lube on it from top to bottom. She squatted over it and slowly lowered herself onto the beast. She kind of bounced slowly, taking a bit more inside her, then slipping some out...two steps forward and one step back. Eventually, she had most of the monster inside her.

She picked up a vibe and put it on her clit, continuing to gently fuck the monster dong as she took herself to orgasm.

When she came, it was loud and she shuddered, pressing down more onto the dildo. She seemed to collapse onto it.

Miss Penny told her not to move and quickly put a mark on the dildo to show how much she'd rammed into herself.

Gary and I offered our hands and she took them to support herself as she slowly eased herself off the Goliath.

Miss Penny took measurements and recorded them on a notepad.

Debbie knew her limits and opted for a dildo a couple of sizes smaller. It wasn't was big around, but it was a bit longer. She laid back in the bed, applied ample lube to it and slowly and steadily fucked it into her pussy, taking it much deeper than I would have guessed. When she had it in almost to the base, she used a small bullet vibe to quickly cum. She held it as deep as she could while Miss Penny verified the depth. Then she slid it out and have it to her to measure.

While Debbie was finishing, Gina had begun teasing her ass with a modest sized dildo. It was about as big around as the plug she had in earlier, but much longer.

Debbie took a different approach and began inserting some anal balls. I watched as she pushed the base, forcing her ass to slowly open then close around a ball, holding tight to the stem then opening for the next ball.

Gina removed the dildo and lubed up the next bigger one--a little bigger around and longer. Like magic, she slid it inside her with one steady push. Her body seemed to easily take its diameter and the length disappearing up her ass was like something from a porn video.

Debbie slid that set of balls out, her anus opening over and over to expel them. She let out s gentle sigh as the last one slipped out.

She picked the largest set of balls available and began pressing them into her butt. There were 5 balls in the set and she managed to get 4 of them inside her. The 5th was pretty large and just wouldn't slide in despite her straining with it.

She called Miss Penny over and she was able to get her measurements off the duplicate in Gina's pile.

Leaving them in her ass, she selected a good sized dildo and began sliding it into her pussy. I could see her straining a bit as the dildo pressed against the balls inside her, probably rubbing each other as she pressed, making her feel completely full.

She stayed like that for about a minute--fully stuffed with the balls and cock. Then let her pussy expel the dildo. She selected the next bigger fake cock and began pressing it into her. It was maybe 1/4" bigger in diameter than the last one, but she was really at her limits. She got it most of the way in and used the vibe.

Debbie loved being stuffed. That feeling of being absolutely full. Even without the lube, she'd be dripping wet from this Task. She came after only about 20 seconds with the vibe. She was loud and came more than once, her body rocking and shaking with orgasms. I counted at least three, but it was hard to tell.

She kept rubbing and pressing the vibe on her clit until the last one passed and she tossed the vibe a few inches away from her.

Miss Penny stepped over and drew a line on the dildo. When Debbie had caught her breath, she let her body push out the dildo and Miss Penny recorded the measurements.

Gina had moved up to a bigger dildo in her ass in the meantime. She was eyeballing the anal beads Debbie had used. It was hard to tell but it seemed like the dildo in her ass was bigger. If she could fit a good sized cock in her pussy, she should be able to win this round.

She called over Miss Penny to measure it. She had it completely in her ass, so Miss Penny could use the duplicate in Debbie's pile.

Gina slipped it out completely then replaced it with the large butt plug she'd used first. She went back into the bathroom and set up the monster dong again--lubing it once more heavily from top to bottom.

She eased back onto it, this time with the added challenge of the plug in her ass. She barely seemed to manage it last time, and this time it seemed she had to work that much harder because of the plug.

Like before, she slowly fucked it into her pussy, grimacing as she tried to force it deeper. She took the vibe and rubbed it hard on her clit, teasing her pierced nipples with her free hand.

The discomfort of it was making it hard to cum. But, she pressed on. Eyes closed and an intense, determined look on her face.

It took her almost 10 minutes to finally cum. When she did, she practically fell over from exhaustion. She had to pull to get the monster cock out of her. Her body was holding onto it tight despite its size.

We helped her onto the bed and Gary pulled the plug from her ass.

We got both girls a hot towel and a cold glass of well earned champagne.

Miss Penny awarded 10 points to Gina and 5 to Debbie based on the relative sizes of the three parts of the challenge.

Ch 17: The Bet - final round (G31, D34)

It was coming up to 1am and the girls were getting tired after the intense evening. But, Miss Penny insisted on her Task happening tonight instead of in the morning.

She told the girls to freshen up and return to her in 30 minutes wearing matching skirts and tops--handing each sub a gift bag containing the outfit in their size.

Back in our room, Debbie took a quick shower and fixed her makeup. The outfit Miss Penny provided was simple--a white button down shirt and a very short plaid dress and white socks. Debbie put it on and added only a pair of comfortable black shoes to it. She looked like a school girl from a porn video.

We headed back to 342 to find Gina dressed as Debbie's twin. Miss Penny had tidied the room a bit, putting the toys out of site.

She handed all four of us envelopes and sent Gary and I to the hotel bar which was open late. She'd text us when she was done.

The note inside the envelopes for Gary and me read "Thanks for letting me play with your slaves. I promise to thoroughly humiliate them but do no lasting damage. Shouldn't take more than 2 hours. I'll text you when we're done. MP"

We chatted in the bar speculating about what Miss Penny would get up to with the girls. I got the details from Debbie the next day for the part below.

From Debbie's journal--

MP handed us the envelopes and asked our Masters to go to the bar so she'd have us to herself.

This Task was all about humiliation. We would humiliate ourselves, each other and she would humiliate us. It was a winner take all round where whichever of us didn't do something would lose. If we both did everything, then she'd give us different points.

It had already been a crazy, super intense night. I was still a bit sore from the piercings and the stuffing Task earlier. But, I knew MP was going to make us work for this round!

Master isn't that into humiliation so I wasn't really sure what to expect.

She started by making us drink large glasses of water. So it looked like pee was going to be involved somehow.

Then she had us each put our hair into matching pigtails with bows that matched the plaid skirts. MP also had us put on matching lace chokers with small gold bells with "Dee" and "Ginny" engraved on them. Probably too small for anyone to read.

Now we looked like women trying to cosplay at middle schoolers.

Then she gave us each a small permanent marker and we took turns writing on each other.

I went first, so I wrote "fucktoy" on Gina's butt cheek. Then she wrote "cocksucker" across my chest. Next I wrote "whore" on her left leg below her skirt. So she wrote "ask me for a bj" down the back of my leg. I wrote "free hand jobs" on her arm and she got really nasty and wrote "slut" on my forehead.

She took a few pics of us modelling our look including a side view pic of us kissing each other.

She then gave us each a medium jewelled butt plug and we had to put them in each other. Gina bent over, her skirt flipped onto her back and I lubed up the plug and gently worked it into her ass. When she'd done the same, MP took a pic of us both bent over, spreading our ass cheeks and showing off the pink jewels peeking out of our asses.

She had one more adjustment for us to make before we went out. We were each allowed to change one thing about the other slaves clothes. MP had a few things like scissors that we could use.

Gina had to go first to give me a bit of revenge for the body writing!

She decided to remove the top three buttons of my shirt so it was unbuttoned down to below my breasts. I'd be ok as long as I didn't bend or stretch too much, but anyone I met got to see most of my boobs.

I was kinda pissed about her writing on my face. So, I made two vertical cuts on the back of her skirt. Now when she walked, the skirt would kind of open up and give everyone a peek at her ass.

MP grabbed her large handbag and led us out of the hotel and had us walk the couple of blocks to the 7-11 we were in back at the start of this crazy night.

She gave us each a few dollars and told us to hold hands and go buy a vanilla yogurt and a bottled water. We stepped inside looking ridiculous in our school girl outfits with body writing and my tits and her ass practically hanging out for everyone to look at.

Thank god there were only like three people in the store. A couple who looked like they were on a date we're buying snacks and an older guy was working the register.

We walked in holding hands and walked back to the yogurts. We passed by the couple who stared at us and laughed as we got our waters.

The guy at the register didn't seem to even notice us until we left. I saw him really looking at Gina's ass as we walked out.

When we got outside, MP was talking to three college guys who were sitting in their car smoking weed and listening to music.

She asked the guys if they'd give her a joint if we showed them our tits. The laughed and said they'd give her a toke.

She told us to unbutton our shirts and let the boys ogle us for like a minute while she smoked their joint. The guys laughed and joked--reading the stuff on our skin. MP had us turn around and Gina had to lift her skirt so they could read all of it.

When she was done, she handed it back to them and waved at us to put our shirts back on.

She led us back towards the hotel, but took us to a small grass area at the edge of the hotel grounds. It was just grass, hedges and trees next to the main road. There was a bench and trash can there for people waiting for the bus. There was only one streetlight near the bench, so it was pretty dark.

There wasn't much traffic since it was so late. A car might go by every few minutes, but there weren't very many while we were there.

She took the yogurts from us and spooned it out onto paper plates she had in her handbag.

MP made us both kneel in the grass and set down a paper plate in front of each of us. She told us to put our hands behind our backs, lifting up our skirts and to eat the yogurt with just our mouths.

She walked around us taking pictures and telling us we looked like piggies eating slop. I think two cars went by while we were licking up the yogurt but they didn't slow down.

When she showed us the pictures later, it looked like we were licking up cum. It was all over our chin, nose and cheeks but she told us not to wipe it off. I think she wanted it to look like we'd gotten facials.

When we were done, she had us walk through the hotel parking lot towards the back doors by the pool. Since it was so late, there was no one around to see us. But, I was looking the whole time. I didn't want anyone to see me and I figured it was about to get worse.

There was a small U shaped alcove at the side of the pool with 5 foot walls on three sides and a metal pole in the middle with showers so swimmers could rinse off before leaving the pool area.

MP led us over to the shower and emptied our water bottles into the drain. Then she pulled two small funnels out of her handbag and handed them to us.

"I'm guessing you two sluts need to pee...so use these and pee into your bottle. If you spill any, there will be consequences. Whenever you're ready, girls."

She had that evil smile on her face again as she sat down on one of the nearby pool chairs.

My bladder was full so I was ready to pee. I put the funnel into the bottle and held it up against me as I peed. I could feel it splashing up from the funnel onto my skin. It seemed to take forever, but eventually I was done and the bottle was about 2/3 full of warm piss.

MP filmed the whole thing, telling me to lift my skirt so she'd have a better view. When I finished, she called me a good little slut and pointed at a chair next to her, so I sat down.

Gina stood at the drain, lifted her skirt and peed. She got a bit sloppy and some of her pee sloshed outside the funnel. She quickly corrected it, pulling the funnel closer to her body so she got the rest into the bottle. It was about 1/2 full when she was done.

MP said "Tsk tsk Gina...set your bottle down and clean up your mess."

Gina looked around and said, "Miss Penny...I don't see any towels or anything to clean it up with."

MP had that evil smile on her face again.

"Use your tongue, slave."

Gina scrunched up her nose, frowning. But, she got down on her hands and knees and licked up the small puddles and droplets on the concrete.

MP filmed her the whole time, zooming in on her tongue as she licked the floor clean.

"Now, girls. You're getting near the end. Grab your bottles and let's go back to the room."

Ch 18: The Bet finishes (G31, D34)

More from Debbie's journal--

We walked back to room 342 from the pool. MP took us the long way, making us walk through the lobby in our ridiculous outfits, with body writing and dried cum-looking yogurt on our faces carrying bottles that most people would guess was pee.

We only passed a few people in the corridors and got a few looks and one guy really looking us up and down with a leery gaze. The woman at reception thankfully was busy with the computer and never looked up.

I was never so happy to make it to an elevator before in my life. Once the three of us got in and the doors closed, we were ok. No one else got on the elevator and there wasn't anyone on the 3rd floor when we got there. The way MP is, I thought she'd find someone to join us in the elevator.

Back in room 342, MP told us we had just three more things to do, then she'd release us back to our Owners.

She told us we were going to take turns worshiping the other slave. She flipped a coin and Gina won the toss to go first.

MP has me lay back on the bed and had Gina strip naked.

I was glad Gina had to go first because I had no idea what MP wanted. Luckily, Gina did.

Gina got on her knees at my feet and put her head flat in front of her, extending her arms out towards me, but not touching me. She looked like she was praying.

Then she took my left foot in both hands and gently massaged it as she kissed the top of my foot. After she'd done this for a minute or two, she tilted my foot towards me and kissed the base of my foot several times working her way from heel to toes.

She shifted her attention to my leg, again massaging and kissing them as she worked her way up from ankle to thigh.

Gina repeated the process on my right foot and leg before doing something similar to each arm.

Next, she removed the skirt and top, gently teasing my tummy and kissing a path from my belly button up to my neck.