Jessicas Awakening Ch 10

Disclaimer:

Here is chapter ten in the Stacy and Jessica saga. As always, I encourage you to read the previous chapters, for context and to familiarize yourself with the characters. Please let me know what you think in the comments below. Story ideas are also welcome! Standard legal stuff: all characters are above the age of 18, any resemblance to real life people and/or situations is entirely coincidental, I don't mind if you post this on another site just please acknowledge me somewhere in the post. Hope you enjoy the story!

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Stacy turned to her fellow mistress Trinity and began to whisper in her ear. She had invited Trinity and her pet Katie over to help her train her new pet Jessica and had come up with a great idea for how to do so. Jessica, still bound to the ottoman next to Katie, had asked for a glass of wine, and Stacy quickly realized she could use this as a way to teach Jessica how to hold back an orgasm. After whispering her idea to Trinity, who enthusiastically agreed, they walked over and untied Jessica and Katie from the ottoman, removing all of their bindings, before Stacy ordered them to kneel silently in the middle of the room. The two mistresses then walked out, leaving the pets alone.

Jessica and Katie stared at each other, both perplexed as to what their mistress' had planned for them. They were incredibly horny; both having enjoyed the way that their mistress' had pleasured themselves on their faces. They remained silent for about 15 minutes, before curiosity finally got the better of Jessica. "What do you think their doing?" She whispered to Katie.

"I'm not sure, but I'm betting we'll enjoy it!" Katie replied.

"Me too!" Jessica squealed back. At that moment Stacy and Trinity walked back into the room, their arms full of items.

"I thought I told you to be silent!" Stacy said to the still kneeling woman, venom in her voice.

"I'm sorry mistress!" Jessica whined, knowing she had been caught.

"And you, my pet!" Trinity snarled at Katie. "You are supposed to be helping to train Jessica, and this is the second time you two have disobeyed us since you met! I'm starting to regret bringing you over here!"

"Please mistress!" Katie responded, lowering her head and adopting a puppy dog face. "Forgive me, I will do a better job from now on! I just can't resist her, she's SOOO beautiful!"

Jessica felt a bit of pride at Katie's words. She was starting to discover her immense sexual appeal, and had these three women to thank for it. "Please mistress!" She said, hoping to deflect some of the blame from her fellow pet. "It was my fault!"

"I don't care whose fault it was, you both disobeyed, so you will both be punished." Stacy responded. "Now you will remain SILENT while we finish setting up our little game."

"Yes mistress!" Both Katie and Jessica replied at the same time. Stacy and Trinity laid the various items in their arms on top of the ottoman, quickly organizing them.

"Here's how this is going to work; we have three rounds for you that will test your ability to withstand your orgasm. You can cum whenever you like, but it will behoove you to hold them as much as possible." Stacy began. "The winner of each round will earn a glass of wine, the loser a little punishment. The overall winner will get a free orgasm in any manner they chose, as well as another little prize, while the loser will get another, bigger, punishment. Now get on all fours, facing away from each other." Jessica and Katie complied immediately, their curiosity peaked. Jessica was nervous, never having really tried to withstand her orgasm before. "Our first game is a little Tug-of-War." Stacy continued. She was holding two sets of anal beads tied together at the end. Both sets of beads were comprised of 6 beads, each bead nearly 2-inches in diameter. Her and Trinity removed the plugs from their pet's asses, pushing them into their respective owners' mouths for cleaning, before pushing a set of beads each into Jessica and Katies asses, eliciting muffled moans from the woman as each bead pushed past their sphincter. The two bound women's asses were now touching. "Don't move!" Stacy instructed, before she and Trinity strapped the same clit stimulators that had used the week before to their pets. Stacy and Trinity walked over to the end table, finishing the glasses of wine they had poured for themselves earlier and pouring another one for themselves and a third as a prize. They picked up their phones, walking back to the kneeling woman.

"The rules for this game are fairly simple." Stacy explained. "The first to get all of the beads out of their ass wins. If either of you orgasm at any time we will stop the game, and that person will have all their beads reinserted. But there is a catch! Every time you remove a bead you will turn the vibrations up on the other pets' beads, but also turn up the vibrations on your own egg and clit vibrator." She finished, a wicked grin on her and Trinity's faces.

Jessica was extremely nervous as she heard the rules of the game. She hadn't minded the beads being inserted too much, despite their size, as she had always enjoyed anal sex immensely. She had only attempted to hold her orgasm on one other occasion and had been unsuccessful then, leading to her first punishment. "I expect you to win this easily, my pet!" Trinity said to Katie, snapping Jessica from her revere.

"I don't know, Trin!" Stacy replied. "You haven't seen what an anal slut Jessica can be!" She leaned down to whisper in Jessica's ear, "Just do your best, Jess!" She said. "Nobody will think less of you if you lose." Stacy stood up and nodded at Trinity. "Ready, set, GO!" She screamed, pushing the button to start the vibrations on her pet's toys. Beside her Trinity pushed the button on her phone simultaneously, starting Katies vibrators as well.

Jessica and Katie both let out simultaneous moans, the toys embedded deep inside them driving them towards their orgasms. Jessica felt a slight pull on the beads in her ass as she tried to get her bearings, a moment later her beads began to vibrate harder, further disorienting her. "That's one for Katie!" Trinity said, keeping count for her pet. Jessica steeled herself and began to crawl forward, groaning as the first bead stretched her sphincter before popping out of her ass. She nearly collapsed as the toys in her pussy and at her clit kicked up a notch, pushing her very close to an orgasm.

"All tied up!" Stacy said, keeping her own count.

"Not for long!" Trinity retorted as a second bead popped out Katies stretched out asshole.

The increased vibrations in Jessica's ass pushed her over the edge, triggering an orgasm. The toys inside her shut off almost as soon as she came, reducing the strength of her climax. She shuddered for a moment before opening her eyes, hornier than she had been before the orgasm.

"I'm disappointed, my pet." Stacy said to Jessica, staring down at her. "You will have to do better if you want some wine!"

"I will, mistress!" Jessica whined back. She got back to her knees, determined to put up more of a fight. Stacy reinserted the bead she managed to remove, turning her pussy and clit stimulators to their lowest level while reactivating the beads embedded in Katie.

"Ready, set GO!" Stacy shouted again. Jessica immediately began crawling forward, popping a bead from her ass a moment after Stacy finished yelling. "That's my girl!" Stacy said, smiling at the look of determination on Jessica's face. Jessica managed to pull a second bead from her asshole before Katie could react, the increased stimulations pushing her towards a second orgasm.

Katie finally reacted, crawling forward and pulling the third bead from her ass a moment before Jessica pulled her third. The increased stimulations pushed her right to the edge of an orgasm, a load moan issuing from her lips. She nearly had the fourth bead out when Jessica got her fourth out, triggering her orgasm. Like Jessica's before her, the toys shut off immediately, reducing the strength immensely.

"STOP!" Stacy screamed, halting Jessica in her tracks. "Much better my pet!" She said to Jessica, beaming.

"You got your work cut out for you slut!" Trinity spat at Katie. She was surprised by Jessica's newfound resolve but was also secretly delighted by her anal prowess. She was going to love playing with the sexual demon Stacy had released. She reinserted the beads into Katies ass, prepping to turn them back on in a moment.

"Ready, set, GO!" Stacy shouted for the third time. At the word go Katie lunged forward, instantly pulling three beads from her ass and eliciting an "Ohh fuck!" from both pets. The sudden, intense increase in vibrations pushed Jessica close to another orgasm, a huge shudder running through her. She steeled herself and began crawling forward again, popping the fifth bead from her gaping asshole a moment before Katie pulled her fourth. The vibrations coming from her toys kicked up another notch, pushing her to the very edge of her orgasm. She took a deep breath, feeling the beads kick up to their maximum as Katie pushed the fifth bead out, as she crawled forward the final bit and popped her final bead from her stretched out asshole. She instantly came, collapsing forward as the intense vibrations still coming from her pussy and clit drove the large orgasm she had been craving.

"Told you!" Stacy directed at Trinity, smirking. "My girl is a top-notch anal slut!"

"She may have won the battle, but my pet will win the war!" Trinity retorted. She reached down and pulled the last bead from Katies ass, causing Katie to have another small orgasm. "I expect you to perform much better in the next two rounds. Now clean!" She said to Katie as she recovered, holding up both sets of beads. Katie licked and sucked the beads, thoroughly enjoying her "punishment".

Stacy strode over to the end table, grabbing her glass of wine and the glass poured for the winner. She walked back to Jessica, still lying on her side on the floor, trying to regain her breath. Once Jessica recovered, she handed Jessica her glass of wine, saying "You earned that, my pet!".

"Thank you, mistress!" Jessica replied, holding her glass up for a toast, which Stacy reciprocated. The two women drank their wine, staring into each other's eyes. When they had finished Stacy took the empty glass from Jessica, placing it back on the end table and refilling it for the next winner.

"Time for round two!" She said. "On your knees, face to face." After Jessica and Katie complied, their knees actually touching, Stacy and Trinity reattached their ankle cuffs, reinserting Jessica and Katie's butt plugs, before cuffing the pet's wrists behind their backs. Trinity then grabbed two short lengths of rope and tied Jessica and Katie's wrist cuffs to their ankle cuffs, forcing them to arch their back slightly and thrust out their chests. Stacy, meanwhile, had grabbed a glass of ice and two sets of nipple clamps. She grabbed a piece of ice and began to rub it against Jessica's nipples, causing them to harden and eliciting a moan from her re-bound pet. She put one set of clamps on Jessica's sensitive nipples, attaching a chain with a small box between the two breasts. She repeated the process on Katie, rubbing her nipples with ice to harden them before attaching the clamps and chain. She then put what looked like a large popsicle stick in each of the bound woman's mouths.

"Here's how round two is going to work," Stacy began. "Me and Trinity are going to try and stack dice on the sticks in your mouths, starting with 2, then 3, then 4, and finally 5. Every time we complete a stack, we will place a small weight into the other pet's box, like so." Stacy and Trinity placed a small weight each into the bound woman's box. The increased pull on Jessica's nipples caused her to groan loudly. "It will also cause your own toys to kick up another notch." Stacy continued. "If you orgasm, you will have to restart at 2 but we will not remove or add and weights until you reach a new level. The first one to stack all 5 wins!"

Jessica was more nervous to start this game than she had been the first. She had always loved anal, and while she liked to have her boobs played with, she had never had someone pull at her nipples as hard as the clamps were, and this was just the start. Her only refuge was that the pleasure outweighed the pain at the moment. She smiled at this, loving how Stacy could bring out so many new aspects of her sexuality, which caused the stick to drop from her mouth. Stacy picked it up, placing it back in Jessica's mouth and leaning down to whisper in her ear, "I have faith in you, just relax and you'll be fine.".

Stacy stood back up, nodding to Trinity. "On the count of three. One, two, THREE!" she shouted, beginning to stack the green dice in her hand onto the stick in Jessica's mouth, while Trinity did the same with her black dice next to her. They both quickly stacked two dice, each depositing another weight into the other pet's box. Jessica groaned at the extra weight, as well as the increased vibrations from her toys, spilling the two dice that were on the stick. Katie, meanwhile, took the extra stimulations easily. Trinity had used nipple clamps before, even playing a similar game, which gave her an advantage. Trinity quickly stacked the third die, smiling as she popped the third weight into the box attached to Jessica's nipples.

Jessica felt the third weight land in her box, but this time she was able to withstand the increased stimulation on her nipples. She was determined to put up a fight for her mistress. Stacy had restacked the first two dice, and finished stacking the third as Trinity placed the weight. Jessica was surprised that the pleasure coming from her nipples still outweighed the pain. She steeled herself for the increased vibrations from her toys, her lips quivering slightly as they kicked in. Somehow the dice didn't fall. Katie had accepted the additional weight and vibrations with ease, practically a rock. Trinity quickly placed a fourth die onto her stack, grinning broadly as the stack remained standing perfectly. She hesitated briefly, waiting for Stacy to finish stacking her own fourth die. The two women popped the next weight into the opposite pet's box, turning up the vibrations at the same time.

Jessica came instantly, the increased stimulations coming from her breasts and crotch pushing her over the edge. The dice tumbled to the ground as she briefly spasmed, her toys having shut off an instant after her orgasm hit, ruining it. She quickly came back to reality, panting heavily. She looked up at Stacy, adopting a puppy dog face. "I'm sorry mistress!" She said. "I ruined all your hard work!"

"Yes, you did my pet, and it cost us the game!" Stacy replied, pointing at Katie. Trinity finished stacking her fifth die on to the stick in Katies mouth, leaning down to kiss her pet on the head as the dice still stood. She then reached over and popped her last weight into Jessica's chain. This one was as heavy as the previous ones combined, pulling her nipples nearly to the breaking point. To Jessica's great surprise, the pleasure still far outweighed the pain.

"You may cum, my pet!" Trinity said to Katie. Katie complied immediately, the stick and dice finally falling from her mouth as she experienced a massive orgasm. "Don't be too hard on her Stace, me and Katie have played a game like this before." She directed at Stacey, smirking.

"You little skank!" Stacy replied, with mock irritation meant for Jessica. "No wonder you suggested it! I shouldn't count this, but I will because you're a guest here." She winked at Trinity. Stacy had known that Jessica was overmatched in this contest but wanted to further push Jessica's boundaries. The two mistresses removed the bindings from their pets. As Jessica fell forward, she felt Stacy's hand at the small of her back. "Stay still! You still have a punishment for losing!" Stacy grabbed a small paddle, rubbing it against Jessica's ass. She began spanking Jessica on the cheeks, alternating between the two.

Jessica squealed at each smack against her ass. "Thank you, mistress!" She moaned, enjoying the pain from the firm spanking mixing with the pain coming from her nipples. Somehow the increase in pain increased her pleasure more, something she was eager to explore further. "I deserve to be punished for my performance! I will do better in the next round!"

"You better, this is for all the marbles!" Stacy shouted, increasing the pace of slaps. She finished with several hard slaps right across Jessica's butt plug, causing a shudder to pass through the still bound woman. She pulled Jessica back to her knees, removing the nipple clamps. She leaned in and kissed Jessica passionately, breaking the kiss after a minute. "You did great Jess! I hope it didn't hurt too much!" Stacy said to Jessica, concern in her voice.

"I loved it, mistress!" Jessica replied. "I felt SOOO good on my sensitive little nipples!"

"God, you really are a little sexpot aren't you!" Stacy replied, grinning wickedly. Beside them Katie had finished her glass of wine, handing it back to her mistress. Trinity returned it to the end table, refilling it again for the final contest. She then grabbed a set of ropes, two wands, two sets of nipple clamps different from the ones they had already used, and a massive double headed dildo from the ottoman. "Lay on your backs!" Stacy directed the kneeling women. Jessica and Katie complied immediately, crossing their legs over the others. Stacy inserted the double headed dildo into the pet's pussies, pushing on their hips until Jessica and Katie's pussies had swallowed the toy up to an equal mark. The toy, coupled with the eggs still embedded within, stretched the pet's pussies to their limit. Stacy and Trinity then bound the two womans hips together, making it so they had to move together as one, before attaching the wands to the pets' thighs in direct contact with their clits. The mistresses then moved the ottoman out of the way, helping to guide the two bound women in an ungainly crab walk to the middle of the room. They attached the new nipple clamps to the pets and walked an equal distance away from them.

"Round number three is a race!" Stacy began. "You must crawl to your mistress. As you get closer to your mistress, the clamps and wand attached to your opponent will begin to increase in vibrations, while your own egg and plug will begin to vibrate more heavily." She continued. "If one of you orgasms, you will both stop, and the opponent will get to move a foot closer to their mistress. First one to kiss their mistress WINS!" She finished with a flourish.

"Remember ladies, this is for the whole thing." Trinity added. "Trust me, you really want that extra reward."

"Very true!" Stacy replied. "On your marks, get set, GO!" She screamed, her and Trinity turned all the toys on to their medium level.

Jessica and Katie both lifted their hips, the toys instantly coming to life in and on their bodies. The two woman pulled at each other, neither gaining any real ground, while the dildo inside them pushed their eggs against their g-spots. Both women moaned and grunted as they tried to pull the other woman in the direction they needed to go. Jessica suddenly had a brain wave, and instead of trying to pull Katie away she stood her ground, gyrating her hips up and down and grinding them into Katie. A loud moan coming from the other pet's mouth letting her know that her strategy was working. She began to pull backward as she gyrated, moving herself nearly halfway to Stacy before Katie was able to stop her. The change in vibrations had brought both women to the verge of orgasm. Katie tried to pull back on Jessica, but Jessica's broader hips gave her a leverage advantage, preventing Katie from moving back towards Trinity. Jessica held her ground and continued to grind her hips against Katie, quickly driving Katie over the edge and into an orgasm.