This idea came to me in a dream. Thanks to some help from a friend, I have made it into a fun new story direction for Ruby and her Cupcake. All characters are over 18. Male character is generic for reader fantasy purposes. All feedback encouraged. Please enjoy!
----------------
It was almost 2 am. Ruby and her ticklish boy toy Cupcake were in bed together, wearing nothing but the silk sheets when Ruby's phone alarm woke them. Cupcake had passed out from an intense belly tickling session hours before, so he was well rested; but before Ruby could get ready herself, she had to brief Cupcake as to what was going on. Why he hadn't seen Janine and Violetta around lately, and what was being planned for him in just a short while.
"Cupcake, wake up." Ruby coaxed. "We have plans today, and before we go, I owe you an explanation. Just listen, and please hear me out."
Without a word, Cupcake obediently sat up in bed and listened attentively.
"You have probably realized that Janine and Violetta are no longer around. I have kept us so busy with time together these days, that I have avoided the issue with you. That wasn't fair of me. The thing is..." Ruby heaved a deep sigh, and continued.
"Janine slipped up." she began. "She was supposed to use another identity in public, but she slipped, and someone called the authorities. She was arrested and charged on multiple counts for her past crimes at the strip club. I only knew of the wrongful imprisonment, but apparently there were many others. She is in prison under a couple life sentences, and we won't be seeing her anymore."
Cupcake's eyes went wide. As she paused, he asked: "Miss Ruby... What happened to Miss Violetta?"
"I was just getting to that. That's the toughest part. I may have ruined a decades-long friendship, simply because I refused to admit my part in it. That I took over and tore down the crime scene. If I had gotten any time, I would've left you abandoned, and I couldn't leave my Cupcake. We started out as a team!"
He giggled and thrashed happily as Ruby blew a loving raspberry on his navel and played his ribs like piano keys. Once he calmed down, Ruby continued.
"So, sad as it was, I wanted to do the right thing. Holding no grudges, I bought her a ticket home to Portugal with an open-ended return. She can come back whenever she'd like. We may even visit her over there one day. For now, I wouldn't blame her if she never speaks to me again."
Ruby looked sad momentarily, but composed herself to continue onto new business.
"Now then," continued Ruby. "You know I teach a Female Business Empowerment class, right? Well, through video clips from the cameras in here, you have been quite a class favorite." Ruby beamed and pinched his cheek.
"For the longest time, I haven't wanted to share you with random women. However... The ladies have been dying to meet you. So, with class finished for the summer, I felt it only fair to share you with the top student in the class. As a reward for a job well done."
Cupcake looked concerned.
Ruby stroked his face. "Oh, don't worry. I briefed her on the ground rules. She knows she can't use violence: hitting, striking or intense spanking. No tattoos or other permanent marks. Also, I'm coming with to enjoy whatever she has planned. I'd never leave you two alone on the first meet. If you're wondering about sexual activity, I told her not right away. I'll always protect you. One more thing... I told her today she can use you however she wants. Tomorrow, she comes home with us as I give her a personal tickling tutorial. So...if she has picked tickling you today, it's an automatic double session!" Ruby laughed maniacally.
"So, come on. It's about an hour's drive to her place and she wants us there ASAP. I have to prepare. All you need, little one, is this robe." She throws him her ratty red one. "She requested you come naked, so put that on after our shower."
Cupcake and Ruby soaked in the shower together. Her short, plump Latina body keeping him still as she washed him. She let him release inside her, as to not appear too horny in front of Ruby's pupil. Once finished, they dried off, Cupcake donned the robe, and Ruby did her makeup. She. dressed, then packed a carry-on bag full of a couple different outfits; including a brand new string bikini she found the other day. After a quick bite, they took off in her Lexus Ruby phoned ahead, as she drove them towards her student's house.
--------------
At about 3 am, their car arrived at a large, handsome two-story McMansion with high outer walls for privacy, and a front gate. Ruby buzzed the intercom, and an excited voice answered.
"Oh you're here!" a southern accent proclaimed. Maybe Georgia, perhaps Louisiana. Difficult to tell through the speaker. "I can see him on my camera! I'm sure he's even cuter in the flesh. Come in, come in!"
As they drive down the access road, Ruby explains that this woman can be boisterous and in-your-face, but she was ultimately harmless. In fact, she took Ruby's class because she wanted to act more bossy and cold-hearted. Otherwise, she was a smart, savvy businesswoman. Hence, her top student.
"However, you are to do WHATEVER she says. No matter WHAT she tells you, you are to cooperate enthusiastically with a smile! AM I UNDERSTOOD?"
"Yes, Miss Ruby." He added the 'Miss' for good measure, though unnecessary inside a vehicle.
"Good, because she earned you today." They parked in the driveway and got out. Cupcake rang the doorbell in nothing but his robe.
The door opened, and out came an enthusiastic, bubbly natural redhead, about six inches taller - and over a decade younger - than Ruby. She was pale, freckled, and was wearing a green silk robe. She invited them in.
"HI CUTIE!" She grabbed him up in a huge, friendly hug. "I hear your sexy self is all mine today. I'm Susan!" She offered her hand, and he shook it.
Ruby piped up: "You are to address her as 'Miss Susan' whenever you are in or on her property!"
"Yes, Miss Ruby!"
Ruby chuckled. "See how well I have him trained, Sue? Subtle, gradual humiliation eventually breaks anyone. Now then... I believe he is at your service!"
"Thank you very much." Susan turned to him. "Now, 'Cupcake' is it?" She cupped her hand on his shoulder. "You won't be needing that, today." She disrobed him, and put it in the adjacent laundry room for safekeeping.
Susan eyed him up and down, obviously pleased. She thought he was even better 'live', than on video. Cupcake blushed and restrained an erection with whatever unsexy thoughts he could conjure up.
"Aw, how cute. I made him blush. Now then," she said, turning serious. "You are to clean this ENTIRE house, TOP to BOTTOM. It should be simple and straightforward. Vacuum any carpets. Oil any wood floors... But leave NOTHING unclean, and I want extra elbow grease put into each and every bathroom! If you're unsure about an area, clean it anyway. This place had better SPARKLE by the time you're finished."
Cupcake looked perplexed. Surely he hadn't heard her correctly.
Ruby, impressed with Susan's moxie, chimed in: "You'd better get moving, Cupcake. I'm sure thats why she wanted us here so early."
"Yes, it was... But I'm not quite through with my instruction."
Ruby offered a nonverbal apology, as Susan pulled something out of her robe pocket.
"This is your - ahem - maid uniform." She showed him a pair of boy-short panties made of a Spandex material. It had a green paisley floral print with the words "Miss Susan's Maid" embroidered on the rear end. "Put it on, please. Time is running short." Susan was firm, but not nasty. Something Cupcake could get used to, but a skill Ruby would argue she needs improvement on. Cupcake slipped on his uniform.
"Okay! Now, this is a very special uniform. If you take any breaks today, or idle in between rooms, this uniform will keep you on task. Ruby and I will be outside watching, my house has cameras too. If we see you are going too slow, I just get my handy app over here..."
Susan fiddled with a tablet and built in vibrators inside the panties came to life.
"HAHAHAHAHAHAHA!" Cupcake roared and fell to the ground without a warning.
"Like it? Thanks to Ruby, I market a remote app for vibrating panties. If you dawdle too long, my friend here will torment your pretty privates!" She laughed as she buzzed him again. Cupcake still on the floor, in hysterics.
Susan helped him up. "I hope you're ready, darlin' Cupcake. Oh, I need you to do me one last little favor. Take off my robe, and put it with yours in the laundry room. Laundry is part your service, of course."
He needed no persuasion. "I understand Miss Susan." He disrobed his housemistress, to reveal an emerald colored string bikini.
"Feel free to change into your suit in the laundry room, Ruby."
She did, with the door open, to tease Cupcake. Ruby rejoined them in the foyer, fully revealing a new royal blue string bikini, complimenting her red velvet hair, and the style matching Susan's own two-piece. To compare their torsos, Ruby and Susan were opposites. Where Ruby had B-cups, Susan had C's. Also, while Ruby was resigned to her Buddha belly, Susan had her own little tummy, but it wasn't as noticeable.
"Okay, darlin'... Everything you need is in the laundry room. I'll give you time to gather everything to start. But at the stroke of 3:30 am, anytime you dilly dally, you get tickled. I'd advise you to stay on task to avoid it. Quicker you start... Quicker you're done. When you are... We'll have a private pool party, the three of us. How's that sound?"
She leaned into him, teasing a kiss on the lips, but just before they made contact, she gave him a soft pinch on the butt. Both women laughed. "NOW GET TO WORK 'N GIT'R DONE!" Susan bellowed. To Ruby: "Let's relax on the patio. How do you take your coffee?"
-----------
Ruby and Susan sat outside on the patio, in their suits, happily chatting away, sipping coffee. Ruby would've gone topless, but she and Sue weren't fully beyond student-teacher yet, so Ruby kept modest, for her that is. It was still dark. Susan kept an eye on the camera feed from her phone.
"He's in the kitchen, with all the supplies." Susan stated.
Ruby checked her phone. "And 3:30 am on the button."
On her tablet, Susan activated the call button for her intercom inside the house.
"OKAY CUPCAKE!" Miss Susan's disembodied voice bellowed. Time to stay on task. You have ALL DAY. So get started! To show we're serious about your work ethic, your uniform will activate at a low setting, and remain until we see your diligence. From there...ANY significant work stoppage will result in HIGHER levels of stimulation." She turned on the vibrating app at a low setting, then shouted: "AM I CLEAR?"
"Teeheeheeheehee....YES MISS SUSAN! Heeheeheehee..."
"START!"
Cupcake did, but not before Ruby accidently on purpose raised the setting to 5. Enough to work through big belly laughs, but still do the job. Once he made some headway with the dishes, they turned it off.
Dawn came and left. Afternoon was approaching, and the women had switched from coffee to margaritas. They were getting familiar quickly, as they bonded over Cupcake's predicament. He had finished the kitchen, including cleaning the fridge and waxing the floor. He had Miss Susan's laundry under control and nearly done. He was almost finished with the entire first level, windows included, with only the downstairs half bath still to go.
"I'll admit, I'm impressed." Ruby told Susan. "We only had to zap him between rooms. With the proper motivation, I should have him do chores around our house. Oh... but I can't just dump our housekeeper."
"Would you mind if I take your darlin's services for myself, every month?"
Ruby loved that idea. "Of course you can. And free of charge, I insist!"
They saw he was scrubbing the toilet, and just for fun, they put the app at full strength and gave him a zap. He doubled over in hysterics with a toilet brush in his hand, as the women laughed.
"You must email me footage of today." Ruby said. "If he's ever disobedient, I can threaten to put it on a cam site!" Ruby laughed, half-jokingly. Susan laughed with her. They turned off the app. Cupcake composed himself and finished the bathroom.
At the second floor, Cupcake was such a Mr. Super-Cleaner, that they decided not to use the vibration anymore...only if he really needed it. As he was working in Miss Susan's master suite, turning down the bed, the intercom came to life.
"Good work, darlin! Maybe someday we can share that bed?" Susan teased. They saw him blush from outside, and giggled.
Time passed, and his last upstairs task was Susan's Master Bath. It was similar to Ruby's at home, so he knew what needed to be done. The task was straightforward, and approaching the end of his servitude. Just as he leaned over to scrub the hot tub, outside Ruby exclaimed: "Oh, I can't resist!" She put the vibration to full strength, and he fell forward inside. He wasn't hurt, just trapped inside in a paralytic fit of laughter. Ruby asked Susan a question, and accidentally forgot about Cupcake for a few minutes. Luckily, Susan rescued him by turning the app off after she answered. Cupcake composed himself and continued on task.
Alas, finally, as Cupcake finished sorting his housemistress' finished laundry. His sentence was complete. Ruby and Susan were happily buzzed and already in the pool. Susan leaned over and used her intercom app.
"CONGRATULATIONS CUPCAKE!" Miss Susan happily offered. "It's after 4 pm! You finished in just over 12 hours. It all looks great from what I can see. Now get your cute little behind out here and join us in this pool!" Susan giggled. Cupcake was on his way. Without thinking, Susan motioned taking her top off. She glanced at Ruby.
"Oh, do go ahead! I go topless in the privacy of my own home all the time!" Susan removed her top without worry. Ruby followed suit, and soon, Cupcake was greeted by the sight of two topless mistresses. A pair of brown nips, along with perky pink ones. He stood mesmerized at the pool deck till Ruby tripped the vibrator at full speed. He collapsed and struggled to get his uniform off. Still mindful not to get it wet. Once it was safely tossed next to a lounge chair, Ruby shut them off. Seizing the moment, Susan grabbed him, and yanked him into the pool. The two older women surrounded him, Susan facing him. Ruby was behind him, as he was riding her thigh like a pommelhorse. They gave him no room to really struggle as they tickled him in the water, keeping him upright.
When he was well lost in laughter, but still mindful, Miss Susan spoke up.
"Well, darlin'! You did such a stellar job on the house, that Miss Ruby and I decided you're comin' to my house EVERY MONTH to do it again! Besides that, y'all be seein' a lot more of me. 'Specially you, Cupcake. How's that sound?"
Cupcake could only laugh and nod his head.
"Oh, he's positively TICKLED by the idea." laughed Ruby.
Cupcake's world soon went dark as they tickled him to unconciousness.
------------
He awoke the next morning over the scent of smelling salts. He was back in his and Ruby's own bedroom, hanging from his restraints, in nothing but his vibrating uniform. Miss Susan was in front of him, taking charge, in a pretty purple string bikini bottom.
"MORNIN' CUPCAKE!" came her soon-to-be-familiar booming greeting. Your Miss Ruby had to take a phone call. Meanwhile, I'm just startin' test-drivin' ya for my tickle day! You know, Ruby's a swell teacher. She even taught me this..."
* PHPHTHTHTHBTBTBT *
Cupcake went hysterical as a familiar-but-new sensation hit his belly.
"Hehe! I can see why Ruby likes this!"
Just then, Ruby rejoined them. Fresh off the phone and topless as well. As Miss Susan dug into his ribs, Ruby addressed him.
"Cupcake, this is Miss Susan's day to tickle you, so don't you DARE resist whatever she tries to do. But before she totally steals your mind, I have to tell you this: Due to my shaky relationship with Violetta, and the fact that Susan lives in the general area, and is a whole decade younger than me, I have changed my power of attorney. If ever something were to happen to me, Miss Susan becomes your guardian. DO YOU UNDERSTAND?"
Susan let up so he could answer.
"Yes, Miss Ruby. Yes, Miss Susan." Cupcake replied.
"OOH-WEE... I LOVE my new BOYFRIEND! I can't WAIT to get my homestead SPARKLIN' a-gain!"
Ruby activated his vibrating panties, as they both tickled at will.
THE END
----------------
It was almost 2 am. Ruby and her ticklish boy toy Cupcake were in bed together, wearing nothing but the silk sheets when Ruby's phone alarm woke them. Cupcake had passed out from an intense belly tickling session hours before, so he was well rested; but before Ruby could get ready herself, she had to brief Cupcake as to what was going on. Why he hadn't seen Janine and Violetta around lately, and what was being planned for him in just a short while.
"Cupcake, wake up." Ruby coaxed. "We have plans today, and before we go, I owe you an explanation. Just listen, and please hear me out."
Without a word, Cupcake obediently sat up in bed and listened attentively.
"You have probably realized that Janine and Violetta are no longer around. I have kept us so busy with time together these days, that I have avoided the issue with you. That wasn't fair of me. The thing is..." Ruby heaved a deep sigh, and continued.
"Janine slipped up." she began. "She was supposed to use another identity in public, but she slipped, and someone called the authorities. She was arrested and charged on multiple counts for her past crimes at the strip club. I only knew of the wrongful imprisonment, but apparently there were many others. She is in prison under a couple life sentences, and we won't be seeing her anymore."
Cupcake's eyes went wide. As she paused, he asked: "Miss Ruby... What happened to Miss Violetta?"
"I was just getting to that. That's the toughest part. I may have ruined a decades-long friendship, simply because I refused to admit my part in it. That I took over and tore down the crime scene. If I had gotten any time, I would've left you abandoned, and I couldn't leave my Cupcake. We started out as a team!"
He giggled and thrashed happily as Ruby blew a loving raspberry on his navel and played his ribs like piano keys. Once he calmed down, Ruby continued.
"So, sad as it was, I wanted to do the right thing. Holding no grudges, I bought her a ticket home to Portugal with an open-ended return. She can come back whenever she'd like. We may even visit her over there one day. For now, I wouldn't blame her if she never speaks to me again."
Ruby looked sad momentarily, but composed herself to continue onto new business.
"Now then," continued Ruby. "You know I teach a Female Business Empowerment class, right? Well, through video clips from the cameras in here, you have been quite a class favorite." Ruby beamed and pinched his cheek.
"For the longest time, I haven't wanted to share you with random women. However... The ladies have been dying to meet you. So, with class finished for the summer, I felt it only fair to share you with the top student in the class. As a reward for a job well done."
Cupcake looked concerned.
Ruby stroked his face. "Oh, don't worry. I briefed her on the ground rules. She knows she can't use violence: hitting, striking or intense spanking. No tattoos or other permanent marks. Also, I'm coming with to enjoy whatever she has planned. I'd never leave you two alone on the first meet. If you're wondering about sexual activity, I told her not right away. I'll always protect you. One more thing... I told her today she can use you however she wants. Tomorrow, she comes home with us as I give her a personal tickling tutorial. So...if she has picked tickling you today, it's an automatic double session!" Ruby laughed maniacally.
"So, come on. It's about an hour's drive to her place and she wants us there ASAP. I have to prepare. All you need, little one, is this robe." She throws him her ratty red one. "She requested you come naked, so put that on after our shower."
Cupcake and Ruby soaked in the shower together. Her short, plump Latina body keeping him still as she washed him. She let him release inside her, as to not appear too horny in front of Ruby's pupil. Once finished, they dried off, Cupcake donned the robe, and Ruby did her makeup. She. dressed, then packed a carry-on bag full of a couple different outfits; including a brand new string bikini she found the other day. After a quick bite, they took off in her Lexus Ruby phoned ahead, as she drove them towards her student's house.
--------------
At about 3 am, their car arrived at a large, handsome two-story McMansion with high outer walls for privacy, and a front gate. Ruby buzzed the intercom, and an excited voice answered.
"Oh you're here!" a southern accent proclaimed. Maybe Georgia, perhaps Louisiana. Difficult to tell through the speaker. "I can see him on my camera! I'm sure he's even cuter in the flesh. Come in, come in!"
As they drive down the access road, Ruby explains that this woman can be boisterous and in-your-face, but she was ultimately harmless. In fact, she took Ruby's class because she wanted to act more bossy and cold-hearted. Otherwise, she was a smart, savvy businesswoman. Hence, her top student.
"However, you are to do WHATEVER she says. No matter WHAT she tells you, you are to cooperate enthusiastically with a smile! AM I UNDERSTOOD?"
"Yes, Miss Ruby." He added the 'Miss' for good measure, though unnecessary inside a vehicle.
"Good, because she earned you today." They parked in the driveway and got out. Cupcake rang the doorbell in nothing but his robe.
The door opened, and out came an enthusiastic, bubbly natural redhead, about six inches taller - and over a decade younger - than Ruby. She was pale, freckled, and was wearing a green silk robe. She invited them in.
"HI CUTIE!" She grabbed him up in a huge, friendly hug. "I hear your sexy self is all mine today. I'm Susan!" She offered her hand, and he shook it.
Ruby piped up: "You are to address her as 'Miss Susan' whenever you are in or on her property!"
"Yes, Miss Ruby!"
Ruby chuckled. "See how well I have him trained, Sue? Subtle, gradual humiliation eventually breaks anyone. Now then... I believe he is at your service!"
"Thank you very much." Susan turned to him. "Now, 'Cupcake' is it?" She cupped her hand on his shoulder. "You won't be needing that, today." She disrobed him, and put it in the adjacent laundry room for safekeeping.
Susan eyed him up and down, obviously pleased. She thought he was even better 'live', than on video. Cupcake blushed and restrained an erection with whatever unsexy thoughts he could conjure up.
"Aw, how cute. I made him blush. Now then," she said, turning serious. "You are to clean this ENTIRE house, TOP to BOTTOM. It should be simple and straightforward. Vacuum any carpets. Oil any wood floors... But leave NOTHING unclean, and I want extra elbow grease put into each and every bathroom! If you're unsure about an area, clean it anyway. This place had better SPARKLE by the time you're finished."
Cupcake looked perplexed. Surely he hadn't heard her correctly.
Ruby, impressed with Susan's moxie, chimed in: "You'd better get moving, Cupcake. I'm sure thats why she wanted us here so early."
"Yes, it was... But I'm not quite through with my instruction."
Ruby offered a nonverbal apology, as Susan pulled something out of her robe pocket.
"This is your - ahem - maid uniform." She showed him a pair of boy-short panties made of a Spandex material. It had a green paisley floral print with the words "Miss Susan's Maid" embroidered on the rear end. "Put it on, please. Time is running short." Susan was firm, but not nasty. Something Cupcake could get used to, but a skill Ruby would argue she needs improvement on. Cupcake slipped on his uniform.
"Okay! Now, this is a very special uniform. If you take any breaks today, or idle in between rooms, this uniform will keep you on task. Ruby and I will be outside watching, my house has cameras too. If we see you are going too slow, I just get my handy app over here..."
Susan fiddled with a tablet and built in vibrators inside the panties came to life.
"HAHAHAHAHAHAHA!" Cupcake roared and fell to the ground without a warning.
"Like it? Thanks to Ruby, I market a remote app for vibrating panties. If you dawdle too long, my friend here will torment your pretty privates!" She laughed as she buzzed him again. Cupcake still on the floor, in hysterics.
Susan helped him up. "I hope you're ready, darlin' Cupcake. Oh, I need you to do me one last little favor. Take off my robe, and put it with yours in the laundry room. Laundry is part your service, of course."
He needed no persuasion. "I understand Miss Susan." He disrobed his housemistress, to reveal an emerald colored string bikini.
"Feel free to change into your suit in the laundry room, Ruby."
She did, with the door open, to tease Cupcake. Ruby rejoined them in the foyer, fully revealing a new royal blue string bikini, complimenting her red velvet hair, and the style matching Susan's own two-piece. To compare their torsos, Ruby and Susan were opposites. Where Ruby had B-cups, Susan had C's. Also, while Ruby was resigned to her Buddha belly, Susan had her own little tummy, but it wasn't as noticeable.
"Okay, darlin'... Everything you need is in the laundry room. I'll give you time to gather everything to start. But at the stroke of 3:30 am, anytime you dilly dally, you get tickled. I'd advise you to stay on task to avoid it. Quicker you start... Quicker you're done. When you are... We'll have a private pool party, the three of us. How's that sound?"
She leaned into him, teasing a kiss on the lips, but just before they made contact, she gave him a soft pinch on the butt. Both women laughed. "NOW GET TO WORK 'N GIT'R DONE!" Susan bellowed. To Ruby: "Let's relax on the patio. How do you take your coffee?"
-----------
Ruby and Susan sat outside on the patio, in their suits, happily chatting away, sipping coffee. Ruby would've gone topless, but she and Sue weren't fully beyond student-teacher yet, so Ruby kept modest, for her that is. It was still dark. Susan kept an eye on the camera feed from her phone.
"He's in the kitchen, with all the supplies." Susan stated.
Ruby checked her phone. "And 3:30 am on the button."
On her tablet, Susan activated the call button for her intercom inside the house.
"OKAY CUPCAKE!" Miss Susan's disembodied voice bellowed. Time to stay on task. You have ALL DAY. So get started! To show we're serious about your work ethic, your uniform will activate at a low setting, and remain until we see your diligence. From there...ANY significant work stoppage will result in HIGHER levels of stimulation." She turned on the vibrating app at a low setting, then shouted: "AM I CLEAR?"
"Teeheeheeheehee....YES MISS SUSAN! Heeheeheehee..."
"START!"
Cupcake did, but not before Ruby accidently on purpose raised the setting to 5. Enough to work through big belly laughs, but still do the job. Once he made some headway with the dishes, they turned it off.
Dawn came and left. Afternoon was approaching, and the women had switched from coffee to margaritas. They were getting familiar quickly, as they bonded over Cupcake's predicament. He had finished the kitchen, including cleaning the fridge and waxing the floor. He had Miss Susan's laundry under control and nearly done. He was almost finished with the entire first level, windows included, with only the downstairs half bath still to go.
"I'll admit, I'm impressed." Ruby told Susan. "We only had to zap him between rooms. With the proper motivation, I should have him do chores around our house. Oh... but I can't just dump our housekeeper."
"Would you mind if I take your darlin's services for myself, every month?"
Ruby loved that idea. "Of course you can. And free of charge, I insist!"
They saw he was scrubbing the toilet, and just for fun, they put the app at full strength and gave him a zap. He doubled over in hysterics with a toilet brush in his hand, as the women laughed.
"You must email me footage of today." Ruby said. "If he's ever disobedient, I can threaten to put it on a cam site!" Ruby laughed, half-jokingly. Susan laughed with her. They turned off the app. Cupcake composed himself and finished the bathroom.
At the second floor, Cupcake was such a Mr. Super-Cleaner, that they decided not to use the vibration anymore...only if he really needed it. As he was working in Miss Susan's master suite, turning down the bed, the intercom came to life.
"Good work, darlin! Maybe someday we can share that bed?" Susan teased. They saw him blush from outside, and giggled.
Time passed, and his last upstairs task was Susan's Master Bath. It was similar to Ruby's at home, so he knew what needed to be done. The task was straightforward, and approaching the end of his servitude. Just as he leaned over to scrub the hot tub, outside Ruby exclaimed: "Oh, I can't resist!" She put the vibration to full strength, and he fell forward inside. He wasn't hurt, just trapped inside in a paralytic fit of laughter. Ruby asked Susan a question, and accidentally forgot about Cupcake for a few minutes. Luckily, Susan rescued him by turning the app off after she answered. Cupcake composed himself and continued on task.
Alas, finally, as Cupcake finished sorting his housemistress' finished laundry. His sentence was complete. Ruby and Susan were happily buzzed and already in the pool. Susan leaned over and used her intercom app.
"CONGRATULATIONS CUPCAKE!" Miss Susan happily offered. "It's after 4 pm! You finished in just over 12 hours. It all looks great from what I can see. Now get your cute little behind out here and join us in this pool!" Susan giggled. Cupcake was on his way. Without thinking, Susan motioned taking her top off. She glanced at Ruby.
"Oh, do go ahead! I go topless in the privacy of my own home all the time!" Susan removed her top without worry. Ruby followed suit, and soon, Cupcake was greeted by the sight of two topless mistresses. A pair of brown nips, along with perky pink ones. He stood mesmerized at the pool deck till Ruby tripped the vibrator at full speed. He collapsed and struggled to get his uniform off. Still mindful not to get it wet. Once it was safely tossed next to a lounge chair, Ruby shut them off. Seizing the moment, Susan grabbed him, and yanked him into the pool. The two older women surrounded him, Susan facing him. Ruby was behind him, as he was riding her thigh like a pommelhorse. They gave him no room to really struggle as they tickled him in the water, keeping him upright.
When he was well lost in laughter, but still mindful, Miss Susan spoke up.
"Well, darlin'! You did such a stellar job on the house, that Miss Ruby and I decided you're comin' to my house EVERY MONTH to do it again! Besides that, y'all be seein' a lot more of me. 'Specially you, Cupcake. How's that sound?"
Cupcake could only laugh and nod his head.
"Oh, he's positively TICKLED by the idea." laughed Ruby.
Cupcake's world soon went dark as they tickled him to unconciousness.
------------
He awoke the next morning over the scent of smelling salts. He was back in his and Ruby's own bedroom, hanging from his restraints, in nothing but his vibrating uniform. Miss Susan was in front of him, taking charge, in a pretty purple string bikini bottom.
"MORNIN' CUPCAKE!" came her soon-to-be-familiar booming greeting. Your Miss Ruby had to take a phone call. Meanwhile, I'm just startin' test-drivin' ya for my tickle day! You know, Ruby's a swell teacher. She even taught me this..."
* PHPHTHTHTHBTBTBT *
Cupcake went hysterical as a familiar-but-new sensation hit his belly.
"Hehe! I can see why Ruby likes this!"
Just then, Ruby rejoined them. Fresh off the phone and topless as well. As Miss Susan dug into his ribs, Ruby addressed him.
"Cupcake, this is Miss Susan's day to tickle you, so don't you DARE resist whatever she tries to do. But before she totally steals your mind, I have to tell you this: Due to my shaky relationship with Violetta, and the fact that Susan lives in the general area, and is a whole decade younger than me, I have changed my power of attorney. If ever something were to happen to me, Miss Susan becomes your guardian. DO YOU UNDERSTAND?"
Susan let up so he could answer.
"Yes, Miss Ruby. Yes, Miss Susan." Cupcake replied.
"OOH-WEE... I LOVE my new BOYFRIEND! I can't WAIT to get my homestead SPARKLIN' a-gain!"
Ruby activated his vibrating panties, as they both tickled at will.
THE END
