Debra's Descent Ch. 08-15

Before we leave the next morning, there's another feed at breakfast and a final diaper change. Debbie uses her breast pump to express what she has left and leaves it to a very grateful Laura.

We get very passionate goodbye kisses as La la dissolves back into Laura.

Ch 13: The Bet part 1/5

Have you ever made one of those stupid bets that you've instantly regretted?

I was chatting with another Dom named Gary and we were telling each other how great our current slaves were which escalated into a lighthearted my sub is better than your sub oneupmanship which ended in a challenge.

The rules of the bet were simple—we'd meet next Saturday at 4pm at a neutral venue (a hotel where we had each booked a room) and each provide 2 Tasks for both subs to comply (4 in total) plus a wildcard Task from a Domme friend of ours. Our subs had until Sunday at 10am to complete all 5 Tasks or forfeit. Each Task was worth up to 10 points and subs could choose to pass on any Task. Our Domme friend (Miss Penny) would determine how many points each slave received per Task and was the only person to have seen all the Tasks in advance. The slaves weren't to be told any of the Tasks before the game.

Any special items needed had to be supplied identically to both subs.

Whichever slave lost would spend 24 hours with the other pair doing whatever they asked within limits. I was confident Debbie would win. His sub, Gina, seemed good...but Debbie was next level amazing.

The four of us met in the nearly empty hotel bar at exactly 4pm, as agreed with both subs wearing light coloured jeans and comfortable shoes so they'd be ready for the first few Tasks.

After exchanging hellos and a bit of chit chat, we decided to get started.

I'd agreed to let Gary pick the first Task. He dramatically pulled out two envelopes with the word "one" written on each and both of them sealed with wax for extra drama.

He handed one each to Gina and Debbie. We noted the official start time of 4:13pm and the games began. Both subs tore open their envelopes and read them. Debbie handed it to me and said, "Can we go, Sir?"

We walked to my car as I read the card. Each sub had one hour to get as many piercings or tattoos as they wanted at Ajax's Tatt Room, about 5 minutes away. The most dramatic additions won. Gary had appointments for both of them for 4:30.

We all drove the short distance and arrived at almost exactly the same time. The girls went in and were taken to separate treatment rooms.

Gary and I walked across the street to a Starbucks to camp out and wait for them to be finished. I took a picture of the card and sent it to Miss Penny so she'd be ready to judge the results.

We sipped our coffees and chatted. Neither of us gave the other a clue as to what the remaining Tasks were. Ironically, while we both wanted to win to prove our slave was the best, I don't think either of us was overly invested in the result. This was more like a $2 bet on a coin toss rather than a $200 bet on your favourite sports team.

At exactly 5:30 we both received texts from our girls saying they were ready. We walked back to Ajax's and went into the back where both subs were waiting.

Since it was Gary's Task, we agreed Debbie would go first. I FaceTimed Miss Penny so she could watch.

"Sirs, I got a tongue piercing, bellybutton piercing, six hoops pierced onto my labia, 2 extra ear piercings and a small tattoo that says Properly of Will." As she spoke she showed us each piece of work.

The three of us applauded.

Then Gina: "Sirs, I also got a tongue piercing, both nipples pierced, a clit piercing and got these three tattoos...this easy access and arrow on my butt, this free use on the back of my neck and this slippery when wet above my pussy."

Again, a nice round of applause from the rest of us.

From the phone, Miss Penny spoke, "It's very close...but I'm giving the 10 points to Gina and 9 to Debbie. Her neck tattoo is going to be difficult to keep hidden all the time, so I think that humiliation is worth that extra point. Enjoy the next Task girls."

The four of us clapped and Gary patted Gina on the shoulder. Miss Penny dropped.

Ch 13: The Bet part 2/5 (G10, D9)

At 5:47, I handed the two subs my less fancy envelopes with the word "two" printed on them. They read them quickly, then the four of us walked to our cars.

This challenge was simple. The girls had to drink a Big Gulp from the nearby 7-11. Then Gary and I would take them to different nearby grocery stores where they'd wet themselves, shop for 20 minutes then take a bus back to the hotel. It wasn't a race, so the winner wasn't necessarily the one to get back first. The only time restraint was our dinner reservation at 7:30 back at the hotel.

We arrived in the shop and the girls each grabbed a large glass and filled it up at the soda fountain. Before we'd even completed the purchase, they'd each drank about 1/3 of their sodas. Gary and I sent a few pics to Miss Penny to keep her updated.

Gary took Gina to a Super Walmart while I took Debbie to a Super Target. Both stores were about 15 minutes from the 7-11 so the timing was balanced.

Debbie was practically inhaling the drink as we drove to the store and finished the last drop as we walked in the door, dropping the empty drink into the trash, pausing just long enough for me to take a picture of the empty cup for Miss Penny.

Debbie grabbed a cart and headed to the back corner of the store putting a few random items into the cart so she looked like a normal shopper.

After about 10 minutes in the store, Debbie told me she was ready to pee. I stood in the empty towel aisle and she stepped out into the left-right aisle that connected the far ends of the store.

Holding onto the cart handle, she pretended to look at an end display as she slightly separated her legs and began wetting herself as I filmed it.

The light blue jeans were perfect for this. First the crotch turned dark blue with the wet of her urine, then zigzag streams spread out and down both legs.

As she peed, the deep blue wet patch grew out towards her thighs and both pant legs were crisscrossed with wet streaky lines. Debbie made a point of looking at the camera, smiling broadly.

I filmed my watch to note the time and we began the 20 minute shop.

I sent the video to Miss Penny and kept her updated with pics as we went along our way.

To maximise her points, Debbie made sure she went to the busiest parts of the store so she'd be seen by as many people as possible.

Most shoppers seemed oblivious and didn't seem to notice Debbie's wet jeans. But, the few who did gave her disgusted looks. One older guy really looked her up and down and I'm pretty sure to a picture of her.

Debbie's face was bright red the entire time, but she kept a serene look on her face as if to say "Just another day shopping. Nothing unusual."

As the time wound down, Debbie told me she had to pee again. I followed her as she chose the spot. This time she was really going for a public spot. She'd set the cart aside and was standing in line at the Starbucks near the entrance and registers.

I stood with the cart and filmed her discreetly.

There were three people ahead of her in line, plus the staff. Another five people sitting. A couple of people near the doors plus a dozen or so people at the checkouts.

She was potentially in view of 30 people, but most wouldn't notice what was about to happen.

She ordered an iced coffee and stepped over to the waiting area. As she stood there, she spread her legs slightly and peed again.

Her wet jeans hadn't dried much from last time, so this time her pant legs ended up mostly soaked with only the bottom ankle area still having dry patches.

A minute later her coffee was done and we left the store. I handed her the bus fare and went to the car. The bus stop was at the edge of the parking lot, so she had about a 200 yard walk to get there. A nice walk in dripping wet jeans.

I moved the car near the bus stop and waited until she boarded to drive to the hotel. I sent a few more pics to Miss Jenny before I headed out.

I drove the few minutes back to the hotel and met Gary in the bar. We shared videos and compared notes.

Gary figured Gina had lost this round. She didn't want to walk in wet jeans so she'd actually peed on the floor on a hardware aisle. Per the agreed rules, we both had to let the slaves decide how to complete each Task without input. We would only do what they asked us in order to help them along the way.

The video WAS impressive. Gina walked down the empty tool aisle and then dropped her pants and squatted, her pee making quite a puddle. Then she nonchalantly pulled up the jeans and shopped like nothing had happened.

Like Debbie, she needed to go again before they left. At this point, the penny must have dropped about the wetting, so she wet herself at the bus stop so she'd be wet for the ride back. But, it wasn't nearly as much piss the second time, so only her crotch and thighs were wet.

On their way over, the girls sent pics and videos to Miss Penny and the two of us. We could see them both standing on the bus, getting a mix of looks and other people not noticing at all. One older woman made a disgusted face and seemed to sniff at Gina. We wondered if she could actually smell the piss or was just making a point.

The girls walked in a few moments later smiling and holding hands and joined us at our table at 7:18.

We FaceTimed Miss Penny who ruled that Gina would have normally won on style, but actually had an easier time since her pants were dry while she was shopping. So, Gina got a 5 and Debbie got a 10. The contest was still wide open.

We enjoyed a nice, but quick meal. Everyone was anxious to get to the next Task.

Ch 14: The Bet 3/5 (G14, D19)

After dinner, Gary produced the next envelopes marked "three" and again with wax seals.

Gary had a somewhat sleazy friend named Carl who owned a massage parlour just a few minutes away. The business was mostly legitimate and only customers who asked for extra services got them. But, it wasn't a brothel so extra generally meant a happy ending hand job after a decent massage and the women generally remained fully clothed.

The challenge was to give two massages and whoever had the most in tips won.

We gave the girls a few minutes to freshen up and change into dry clothes, then we headed out.

Gary and I dropped the girls off with the manager and retreated to the back office with Carl who'd come in special to watch. Carl's office had a bank of monitors with CCTV in each of the treatment rooms—as much for the staff's safety as for his personal enjoyment.

They rarely got appointments in the evening, so our slaves would have to wait for walk ins. A few of the regular masseuses were on duty, but Carl had agreed to give our subs priority so we wouldn't be there all night. Standard massages were 30 minutes, so any longer sessions would be handled by the staff.

Carl told us that tips tended to be small. The customers generally tipped $20-$50 for a handjob and $50-$100 for oral. Girls that flashed their tits or let the guy have a feel might get $20-$50 for that. It was up to what the customers wanted to give and what the girls could talk them into paying. Debbie and Gina didn't get this info, so they had no idea what to expect or ask for.

Most of the customers were married guys on a night out or business types away from home. I noticed Carls business was conveniently located within about 5 minutes of at least six good sized hotels—with more not too much further away.

We watched the girls getting instructions from the manager—a female masseuse in her 40s who'd been here about five years. After, they sat in the break room waiting to be called. It was just after 9pm and Carl said it was about to get busy.

A clean cut, middle aged guy was the next in the door. The manager welcomed him in and sent him to room 4 and called Gina in to take care of him.

Debbie didn't have to wait long. Two guys in their early 50s came in a couple of minutes later and were sent to rooms 1 and 7. Debbie was up in room 1 and one of the staff got the other guy.

Gina knocked in the door, then stepped in to the dimly lit room. The guy was facedown on the table with the towel at his waist.

Gina seemed to be a pro at this. She grabbed the hot oil and immediately began working the guy with a deep tissue, Swedish massage. She pressed him hard, digging in with her elbows and working his shoulders.

She kept up a steady conversation with him, but avoided anything overtly sexual. With about 10 minutes left, she had him roll onto his back. Even through the towel it was obvious the guy had a hard on.

She rubbed his head and upper body, then did his legs, teasing his thighs with her nails.

Then she went for the kill. "Do you want me to take care of this for you?" Lightly tapping his cock through the towel.

"Please...I'll make it worth your while."

She dropped the towel to the floor and scooped up a good bit of hot oil in her hands and began rubbing it into his balls and along the length of his cock.

She began sliding her fingers along his length, using the oils to give him a sensual hand job. Soon she added her second hand to the mix and began gently twisting them on each pull.

He didn't last long from the attention and fired his cum in an arc that landed across her wrist and along his thigh.

She left him to clean up and get dressed and was rewarded with a $40 tip.

Meanwhile in room 1, Debbie had taken a different approach. When she entered the room, finding her client face down on the table, she leaned over and as seductively as she could asked him if he wanted a regular massage or a body to body massage.

He stammered in surprise—as a regular, he'd never been offered that before. So he was instantly interested. They agreed a price and she removed her top, rubbing lots of warm oil into her breasts making her nipples rock hard, then leaning over and rubbing her breasts tightly along his back and across his arms and legs. He strained his neck, trying hard to watch her in the mirror across the room.

He was breathing heavy almost immediately, shifting on the table with excitement. She left her top off, but alternated between using her hands and elbows and her breasts to massage him, finishing his back by laying on top of him and using her full weight to press down on him.

She slid off and began kneading his butt, sliding the towel onto his back and teasing his crack and scrotum with her fingers. She finished by drizzling warm oil down along his ass crack and balls, slightly parting his ass so the oil would leak down deeper.

She had him roll onto his back and dropped the towel. She began sliding across his body with her oily breasts and hands, giving his chest and legs equal attention to what his back and butt had received.

She scooped up some hot oil and began dripping large drops onto his cock and balls, making him twitch with lust and expectation.

When she knew he was desperate to cum, she used her hands to quickly stroke up the length of his cock a few times before leaning over and pressing his cock between her oily breasts.

He exploded almost immediately, his cum hitting her under her chin. She kept gently rubbing her boobs on his cock until his orgasm finished.

She left him to clean up and get dressed and headed to the back to freshen up for her second and last client, her $100 tip secured.

Gina's second client was in his early 20s. It looked like he spent a lot of time at the gym judging by his chiselled body and six pack. She wondered why such a hot guy would come here until he opened his mouth and started rudely ordering her around.

She entered the treatment room and he was still dressed, waiting to talk to her.

"I'm guessing you're new, so you don't know my regular treatment. I want a hard deep tissue massage. If you're up for a handy at the end, I tip well. If you'll do a bj, I'll give you $50 extra. What do you say?"

"Make it $100 and you can play with my tits while I massage you."

He looked her up and down. "Ok, but keep your top off."

"Deal. Go ahead and undress and hop on the table."

"Top off first."

Gina shrugged and slipped her top off, revealing her nice C sized boobs with their new (and still sore) piercings.

"I like those." He tugged a bit hard on the left hoop making her flinch. "Nice."

He slipped his clothes off and hopped onto the table, not bothering with the towel at all.

He touched her continuously during the massage, pulling at her nipple hoops, squeezing her nipples, rubbing her ass. At one point, he even tried to undo her pants but she shifted away quickly. It was tricky giving a massage to someone being so handsy.

Gina put all her muscle into the massage, pushing on him as hard and deep as she could, rubbing his knotted muscles and digging into his back and butt muscles. She wanted him to leave sore.

Finally, it was time to work his front and finish him off. She had him flip onto his back and saw why he maybe preferred the masseuses to dating—he had a very tiny cock. Even fully hard as he was now, it was so small she wondered if she could even suck him off properly. At least she'd be able to easily take all of him with no risk of gagging.

He kept her breasts in his hands continuously as she worked to finish his massage, pulling her sore nipples and squeezing them hard.

She took a generous portion of oil in her hands and rubbed his tiny dick and balls. She had to use two fingers to pull his shaft a few times before she put her mouth on him.

She had to blow him using mostly her lips and tongue—she couldn't get her hands involved as well. She even took his balls as well into her mouth by mistake.

He never let go of her boobs which made her want to finish him off as fast as she could.

Eventually she found a rhythm that worked and started moving him quickly to orgasm. Eventually the tiny dick came and she was able to stop. She'd gotten his tip up front, so she told him to have a good day and left quickly, putting her top on back in the staff hallway before joining us in the office.

Debbie was surprised when she stepped back into the treatment room and found a woman laying face down on the table.

"Hi, I'm Debbie and I'll be your masseuse today. What kind of massage were you wanting, miss?"

The woman lifted up, setting her head on her arm so she could look at Debbie.

"I'm Alison and I'm here for the Swedish...or can you recommend something else? Or something...extra?"

"Well...I could do a Thai body on body massage...or I could do the Swedish with a happy ending?"

"I do like a good deep tissue rub...how happy of an ending can you give me?" Her voice was slightly seductive on the last part.

"I have some very nimble fingers...small hands...or you could see how skilled I am with my mouth."

"Yum. How much for your mouth, Debbie?"

"For a guy, I'd ask for $150...but I'm guessing you'll taste amazing, so $100 to make us both happy?"

"Here, pet" she said handing her $100. "And rub me hard. My muscles need it."

Debbie put her full strength into the massage, rubbing Alison's muscles hard and deeply. When she finished her back and shoulders, she spent extra time on her legs, using her nails to tease her thighs. Before she had her roll over, she rubbed a generous dollop of oil into her butt cheeks, sliding her oily fingers into the crack and quickly teasing her anus with an oily fingertip.

Once Alison was on her back, Debbie finished the massage and turned her attention first to teasing Alison's nipples and boobs with her oily fingers.

Then she shifted her attention to Alison's pussy, rubbing her labia and clit with her slippery fingers. Alison moaned softly as Debbie rubbed her clit in firm circular motions, working her to her first orgasm.