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.
