A little preface to this tale. Aside from vague references to age and height, I won't be describing the male character at all, because I want fellow male fans of F/M to picture themselves in the story. Both characters are over 18. If this offends you, stop reading at any time. Feedback appreciated. Thank you.
-----------------
He came to her apartment after answering an ad on a site, meant to find intimate encounters. He was single and completely unattached, but unlucky in the dating world. So he decided to pay for a night of fun. He found a lovely older woman who made him feel at ease during their phone conversations, and her head-and-shoulder shot got him excited to meet her. So there he was. He arrived to find the only the storm door shut. He called out a greeting, as he peered through the screen at the tastefully decorated condo.
"OH HEY!" she answered out from another room. Yep, definitely her youthful-sounding voice. She came to the door quickly, wearing a robe. Yep, definitely her face. "Forgive me," she said as she let him in. "I'm not quite ready. You can help yourself to a drink over there," nodding towards the bar, "and I'll be right out!" She hurried back to finish getting ready.
He indeed fixed himself to a drink to help him relax. As he was sipping, she came out into the living area. As soon as they made eye contact, she removed her Teri-cloth robe and dropped it where she stood. He was stunned, so she came over and gave him a warm hug. "Hi, I'm Ruby. Finally we meet! Oh good, you got yourself a drink."
Ruby was in her early 50s, and had at least a decade on him, if not more. Shorter than him, she stood a half-inch under five feet tall. Her facial features were vaguely Hispanic, yet she had pale Irish skin, with a light dusting of freckles on her cheeks and nose. Her shoulder-length hair was dyed the color of red velvet cake, matching the color of her tiny string bikini. She read in his gaze what looked to be disappointment.
"What's the matter?" she asked. Since she was unusually short, her body fat settled at one place. She had a prominent Buddha belly, that lapped over her little red bottoms. "Are you disappointed?" she wanted to know.
He was embarrassed by what he wanted to say, but he stammered it out. "Oh, no, no..." He blushed.
She sat on the couch and patted the seat next to her. "Its okay, come and sit. You can tell me." Ruby gave him a bright, friendly smile. He sat down.
"It's just, I'm embarrassed to admit that big tummies turn me on. I know it's unusual, but..."
"Oh!" Ruby giggled with relief. "That's actually the best compliment anyone has ever given me. Usually, once a customer sees my full body, they make an excuse and leave. I suppose it's partly my fault for only showing a head shot, but it helps me weed out the superficial...or just the desperate." She laughed. "Okay. Now, before we get to bedroom business, I have some rules, as a professional."
"Oh, of course."
"I'd like you to be satisfied. So, I accept payment after the deed is done, to your liking. The longer we go, the more I charge. Are you prepared for that?"
"Sure, no problem."
"I know you said you're clean, but did you bring the blood work results I asked for?"
He handed her a printed sheet, which she looked over.
"Good, good!" said Ruby. "Just one more thing. I have this condo wired with hidden cameras, for my own protection. If anything were to go wrong, I've got a record. If this makes you uncomfortable, you may leave if you wish. No offense from me. I would then erase all footage featuring you. Pinky swear. But if you go forth, you agree to be on my security footage."
"No, I'm good!"
"Excellent!" Ruby beamed. "Let's get underway...as I get out of these undergarments!" she giggled. Ruby untied the strings of her top. Her slightly droopy, yet rounded B-cup bosoms appeared, as she carelessly flung her top aside. Again, he was mesmerized. "Well," started Ruby. "After yo...OUCH! What the HELL was THAT for?"
In his excitement and eagerness, he reached out and pinched her nipple, while she had her head turned away. Her warm demeanor and character drasticly changed. She stared icy daggers into him.
He was caught off guard. "Uh...um... Don't you like when guys do that?"
"That's not the point!" cried Ruby. "I hugged you, but I NEVER ONCE gave YOU permission to touch ME! And to do it without the respect of looking in my EYES. Perhaps it was a mistake for not including that in my rules up front, yet everything was going so smooth, I figure I could've waited for the bedroom. Lesson learned, Ruby." She scoffed at herself. "Still, you DID touch me without consent, and for that..." Ruby grabbed him by the shirt down to face her. "You MUST be PUNISHED!"
He stood frozen, wholly intimidated by this tiny woman who was older than he was. Ruby retrieved and tied her top back on, as she paced and thought.
"For starters, you've lost any privilege to see any of my private parts. A two piece bikini is as good as you'll get from me. That way, even if you're in your boxers, I'm more clothed than you are, technically. She got an idea. "Hold still", she told him. "Or else you'll be a lot worse off, later!"
She proceeded to strip him down to his boxers, being careful not to damage his clothes. He was too frightened, not too cooperate. "There, that's better!" Ruby smiled. "You know, its a shame. I was actually starting to like you. You know...'Like-Like'." she grinned. "From the moment you complimented my tummy, the one body part I'm self-conscious about, I was starting to have feelings for you. If things went great in the bedroom, I would've confessed them and comped your session. But now..."
Thinking of her self-loathing, and a way to make him suffer, she got an idea.
Ruby went to her utility closet to fetch nylon rope.
"Give me your wrists!" she commanded. No objection. She tied each wrist individually and then together down the middle. She then led him, like a dog on a leash, over to the door frame of the closet. Fetching a bracket, and a step stool, she got his bound hands over his head, and attached them firmly to the top of the door frame. He was stuck as long as Ruby wanted him there, standing in his boxers.
"There, perfect." said Ruby. "Now then," as she continued her angry demeanor. "From this point on, when you address me, you are to end each sentence with 'Miss Ruby ', is that understood?"
Still scared, he said nothing. "I SAID..." Ruby started, as her matching red painted nails accidentally grazed his stomach. At this, he jumped back into the closet as far as his binding would allow.
"WOW!" exclaimed Ruby. "I wasn't planning on starting yet, but that seems to be the perfect icebreaker! But DON'T interrupt me again. Do you understand what I said earlier?"
Giving in, he replied, "Yes, I do, Miss Ruby."
"Glorious! You're learning fast." Now just excuse me. She ducked around him into the closet, found what she wanted, and proceeded to tie his feet to the floor. "In case you were wondering, I have this bondage solely in case a customer puts me in danger, I can subdue him. But you've given me a whole new use for it. Thank you."
"You're welcome, Miss Ruby."
"Well, aren't we well trained already. Very good. But back to the task at hand...to stomach." She laughed. "Aren't I funny? Well, even if you don't think I am, I'm going to make you laugh anyway." She grazed his stomach with her nails in earnest, and kept a slow steady pace. With his feet bound, he couldn't really jump far. He was hers. The tittering and giggles were immediate.
"HEHEHEHEHEHEHEHE!!..."
Ruby ignored them, and proceeded to engage in conversation as she put her talons on auto pilot against his stomach. "I've decided, since I'm 'Miss Ruby', I should give you a name, too. Hmmm..." As she pretended to think , she stuck her finger in his navel and swirled it around.
"HAR HAR HAR HAR HARRR! STOPPP MISS-ISS RU-OO-OOBY! OH MY GAWD!"
"Okay, since you used my name. The light talon tummy tickles resumed. As did the steady giggling. Ruby wanted something simple, yet still sissy enough to embarrass him.
"I've got it!" she exclaimed, as if a cartoon light bulb had gone off. "You will be addressed as, and answer to...'Cupcake'!"
"HEHEHEHEHEHE! I AM HEHEHE MISS RU-OO-BY'S HEHEHEHE CUPCAKE!"
"Good, yes, Cupcake. You are mine here as long as I want you for." As she said this, gears of thought turned in Ruby's mind. She would address them later.
She kept up the light nails on his belly for around a half hour straight. Ruby decided she loved how he sounded when she was in his navel, so she switched to that tactic without warning.
"HARHARHARHARHARHARHAR...NOMISSRU-OO-BYSTAWP!...HARHARHAHAR..." but she continued on.
Since she didn't want Cupcake to pass out, she stopped probing his navel, to reestablish conversation, only resuming to see him struggle with his answers. It seemed worth a try.
"Take a breath, Cupcake." said Ruby. Let's talk. I will ask you a few questions, and play with that navel as you give the answers. Okay?" She sounded friendly again, but he knew better than to displease her.
"Yes, Miss Ruby."
"Great. I will NOT tolerate lying. Here goes. Are you a virgin?" In went Ruby's nail.
"HARHARHARHAR...YES! MISS RU-OO-BY! I AM! HARHARHAR!"
"Okay. And did you seek out an older, not to mention shorter woman - on purpose - to lose your V-card? I'm a dinosaur compared to you." Insert nail.
"HARHARHARHAR IT'S JUST BEEN HARHAR A FANTASY, MISS RU-OO-BY! HARHAR AND I THOUGHT HARHARHAR YOU'RE BEAUTIFUL! HARHARHAR!"
Ruby was taken aback, but she didn't show it. She had to stay angry to keep Cupcake guessing. Perhaps he was just a normal guy, who made a split second's worth of bad judgment. She said no more, yet kept her finger in and out of Cupcake's navel until the top of the hour, and enjoyed his music.
She let him catch his breath, then started a new tactic.
"Sorry, Cupcake. I was having so much fun, I forgot my other questions. Just stay still, and do not move. I'm STILL pissed at you, remember. I'll be right back."
She left to another room, and returned with a big children's book of simple knock-knock jokes. "Okay, Cupcake. This time, I'm going to give you something to laugh about. Just follow along, and I'll give you your big cues. Ahem... 'knock-knock'."
"Who's there, Miss Ruby?"
"A broken pencil."
"A broken pencil who, Miss Ruby?"
"Never mind, it's pointless!"
* PHFHFHFHFTFHTHT~! *
Ruby's lips connected with Cupcake's tummy, and unleashed a devastating raspberry that caught him off guard. He immediately burst out laughing like it was the funniest thing he'd ever heard.
"HAHAHAHAHA!!"
On it went. Stupid knock-knock joke, followed by tummy fart noise followed by near breathless laughter
After another hour had passed, Ruby decided Cupcake had had enough. She put on the ratty Teri-cloth robe she greeted him in, resumed her angry facade, and let him loose.
"Thank you, Miss Ruby."
"THAT'S RIGHT! You're ACTUALLY thanking me that I didn't inflict BODILY HARM as your punishment!" Then: "GET DRESSED!" snapped Ruby.
Cupcake did as he was told.
"Now then," Ruby said calmly but firmly when he finished. "Give me your phone!"
He handed it over. She produced a SIM card from her robe pocket, inserted it, hit the screen a few times, then ejected the card, and handed the phone back.
"There," said Ruby. I now own a copy of your entire contact list, as well as your number, of course. Here's what's going to happen. You will come here three nights a week, INDEFINITELY, for tummy tickling sessions that last no less than THREE hours. Think of it as your second job, and I, Cupcake, your more important Boss. Failure to meet just ONCE, will result in the camera footage sent to everyone on this SIM Card. IS THAT CLEAR?!"
Frightened, he stammered, "Y-yes, Miss Ruby. Anything you say, b-boss!"
"Good, go on. See you here Monday night after your day job, Cupcake!"
"Yes, Miss Ruby!" He left, regretting getting her upset in the first place.
Alone in her condo, Ruby looked forward to their next session. It was a shame he had to touch when he did. But now he's paying the price. She really did still like him. But her affection was something he needed to earn back. He would...eventually.
-----------------
He came to her apartment after answering an ad on a site, meant to find intimate encounters. He was single and completely unattached, but unlucky in the dating world. So he decided to pay for a night of fun. He found a lovely older woman who made him feel at ease during their phone conversations, and her head-and-shoulder shot got him excited to meet her. So there he was. He arrived to find the only the storm door shut. He called out a greeting, as he peered through the screen at the tastefully decorated condo.
"OH HEY!" she answered out from another room. Yep, definitely her youthful-sounding voice. She came to the door quickly, wearing a robe. Yep, definitely her face. "Forgive me," she said as she let him in. "I'm not quite ready. You can help yourself to a drink over there," nodding towards the bar, "and I'll be right out!" She hurried back to finish getting ready.
He indeed fixed himself to a drink to help him relax. As he was sipping, she came out into the living area. As soon as they made eye contact, she removed her Teri-cloth robe and dropped it where she stood. He was stunned, so she came over and gave him a warm hug. "Hi, I'm Ruby. Finally we meet! Oh good, you got yourself a drink."
Ruby was in her early 50s, and had at least a decade on him, if not more. Shorter than him, she stood a half-inch under five feet tall. Her facial features were vaguely Hispanic, yet she had pale Irish skin, with a light dusting of freckles on her cheeks and nose. Her shoulder-length hair was dyed the color of red velvet cake, matching the color of her tiny string bikini. She read in his gaze what looked to be disappointment.
"What's the matter?" she asked. Since she was unusually short, her body fat settled at one place. She had a prominent Buddha belly, that lapped over her little red bottoms. "Are you disappointed?" she wanted to know.
He was embarrassed by what he wanted to say, but he stammered it out. "Oh, no, no..." He blushed.
She sat on the couch and patted the seat next to her. "Its okay, come and sit. You can tell me." Ruby gave him a bright, friendly smile. He sat down.
"It's just, I'm embarrassed to admit that big tummies turn me on. I know it's unusual, but..."
"Oh!" Ruby giggled with relief. "That's actually the best compliment anyone has ever given me. Usually, once a customer sees my full body, they make an excuse and leave. I suppose it's partly my fault for only showing a head shot, but it helps me weed out the superficial...or just the desperate." She laughed. "Okay. Now, before we get to bedroom business, I have some rules, as a professional."
"Oh, of course."
"I'd like you to be satisfied. So, I accept payment after the deed is done, to your liking. The longer we go, the more I charge. Are you prepared for that?"
"Sure, no problem."
"I know you said you're clean, but did you bring the blood work results I asked for?"
He handed her a printed sheet, which she looked over.
"Good, good!" said Ruby. "Just one more thing. I have this condo wired with hidden cameras, for my own protection. If anything were to go wrong, I've got a record. If this makes you uncomfortable, you may leave if you wish. No offense from me. I would then erase all footage featuring you. Pinky swear. But if you go forth, you agree to be on my security footage."
"No, I'm good!"
"Excellent!" Ruby beamed. "Let's get underway...as I get out of these undergarments!" she giggled. Ruby untied the strings of her top. Her slightly droopy, yet rounded B-cup bosoms appeared, as she carelessly flung her top aside. Again, he was mesmerized. "Well," started Ruby. "After yo...OUCH! What the HELL was THAT for?"
In his excitement and eagerness, he reached out and pinched her nipple, while she had her head turned away. Her warm demeanor and character drasticly changed. She stared icy daggers into him.
He was caught off guard. "Uh...um... Don't you like when guys do that?"
"That's not the point!" cried Ruby. "I hugged you, but I NEVER ONCE gave YOU permission to touch ME! And to do it without the respect of looking in my EYES. Perhaps it was a mistake for not including that in my rules up front, yet everything was going so smooth, I figure I could've waited for the bedroom. Lesson learned, Ruby." She scoffed at herself. "Still, you DID touch me without consent, and for that..." Ruby grabbed him by the shirt down to face her. "You MUST be PUNISHED!"
He stood frozen, wholly intimidated by this tiny woman who was older than he was. Ruby retrieved and tied her top back on, as she paced and thought.
"For starters, you've lost any privilege to see any of my private parts. A two piece bikini is as good as you'll get from me. That way, even if you're in your boxers, I'm more clothed than you are, technically. She got an idea. "Hold still", she told him. "Or else you'll be a lot worse off, later!"
She proceeded to strip him down to his boxers, being careful not to damage his clothes. He was too frightened, not too cooperate. "There, that's better!" Ruby smiled. "You know, its a shame. I was actually starting to like you. You know...'Like-Like'." she grinned. "From the moment you complimented my tummy, the one body part I'm self-conscious about, I was starting to have feelings for you. If things went great in the bedroom, I would've confessed them and comped your session. But now..."
Thinking of her self-loathing, and a way to make him suffer, she got an idea.
Ruby went to her utility closet to fetch nylon rope.
"Give me your wrists!" she commanded. No objection. She tied each wrist individually and then together down the middle. She then led him, like a dog on a leash, over to the door frame of the closet. Fetching a bracket, and a step stool, she got his bound hands over his head, and attached them firmly to the top of the door frame. He was stuck as long as Ruby wanted him there, standing in his boxers.
"There, perfect." said Ruby. "Now then," as she continued her angry demeanor. "From this point on, when you address me, you are to end each sentence with 'Miss Ruby ', is that understood?"
Still scared, he said nothing. "I SAID..." Ruby started, as her matching red painted nails accidentally grazed his stomach. At this, he jumped back into the closet as far as his binding would allow.
"WOW!" exclaimed Ruby. "I wasn't planning on starting yet, but that seems to be the perfect icebreaker! But DON'T interrupt me again. Do you understand what I said earlier?"
Giving in, he replied, "Yes, I do, Miss Ruby."
"Glorious! You're learning fast." Now just excuse me. She ducked around him into the closet, found what she wanted, and proceeded to tie his feet to the floor. "In case you were wondering, I have this bondage solely in case a customer puts me in danger, I can subdue him. But you've given me a whole new use for it. Thank you."
"You're welcome, Miss Ruby."
"Well, aren't we well trained already. Very good. But back to the task at hand...to stomach." She laughed. "Aren't I funny? Well, even if you don't think I am, I'm going to make you laugh anyway." She grazed his stomach with her nails in earnest, and kept a slow steady pace. With his feet bound, he couldn't really jump far. He was hers. The tittering and giggles were immediate.
"HEHEHEHEHEHEHEHE!!..."
Ruby ignored them, and proceeded to engage in conversation as she put her talons on auto pilot against his stomach. "I've decided, since I'm 'Miss Ruby', I should give you a name, too. Hmmm..." As she pretended to think , she stuck her finger in his navel and swirled it around.
"HAR HAR HAR HAR HARRR! STOPPP MISS-ISS RU-OO-OOBY! OH MY GAWD!"
"Okay, since you used my name. The light talon tummy tickles resumed. As did the steady giggling. Ruby wanted something simple, yet still sissy enough to embarrass him.
"I've got it!" she exclaimed, as if a cartoon light bulb had gone off. "You will be addressed as, and answer to...'Cupcake'!"
"HEHEHEHEHEHE! I AM HEHEHE MISS RU-OO-BY'S HEHEHEHE CUPCAKE!"
"Good, yes, Cupcake. You are mine here as long as I want you for." As she said this, gears of thought turned in Ruby's mind. She would address them later.
She kept up the light nails on his belly for around a half hour straight. Ruby decided she loved how he sounded when she was in his navel, so she switched to that tactic without warning.
"HARHARHARHARHARHARHAR...NOMISSRU-OO-BYSTAWP!...HARHARHAHAR..." but she continued on.
Since she didn't want Cupcake to pass out, she stopped probing his navel, to reestablish conversation, only resuming to see him struggle with his answers. It seemed worth a try.
"Take a breath, Cupcake." said Ruby. Let's talk. I will ask you a few questions, and play with that navel as you give the answers. Okay?" She sounded friendly again, but he knew better than to displease her.
"Yes, Miss Ruby."
"Great. I will NOT tolerate lying. Here goes. Are you a virgin?" In went Ruby's nail.
"HARHARHARHAR...YES! MISS RU-OO-BY! I AM! HARHARHAR!"
"Okay. And did you seek out an older, not to mention shorter woman - on purpose - to lose your V-card? I'm a dinosaur compared to you." Insert nail.
"HARHARHARHAR IT'S JUST BEEN HARHAR A FANTASY, MISS RU-OO-BY! HARHAR AND I THOUGHT HARHARHAR YOU'RE BEAUTIFUL! HARHARHAR!"
Ruby was taken aback, but she didn't show it. She had to stay angry to keep Cupcake guessing. Perhaps he was just a normal guy, who made a split second's worth of bad judgment. She said no more, yet kept her finger in and out of Cupcake's navel until the top of the hour, and enjoyed his music.
She let him catch his breath, then started a new tactic.
"Sorry, Cupcake. I was having so much fun, I forgot my other questions. Just stay still, and do not move. I'm STILL pissed at you, remember. I'll be right back."
She left to another room, and returned with a big children's book of simple knock-knock jokes. "Okay, Cupcake. This time, I'm going to give you something to laugh about. Just follow along, and I'll give you your big cues. Ahem... 'knock-knock'."
"Who's there, Miss Ruby?"
"A broken pencil."
"A broken pencil who, Miss Ruby?"
"Never mind, it's pointless!"
* PHFHFHFHFTFHTHT~! *
Ruby's lips connected with Cupcake's tummy, and unleashed a devastating raspberry that caught him off guard. He immediately burst out laughing like it was the funniest thing he'd ever heard.
"HAHAHAHAHA!!"
On it went. Stupid knock-knock joke, followed by tummy fart noise followed by near breathless laughter
After another hour had passed, Ruby decided Cupcake had had enough. She put on the ratty Teri-cloth robe she greeted him in, resumed her angry facade, and let him loose.
"Thank you, Miss Ruby."
"THAT'S RIGHT! You're ACTUALLY thanking me that I didn't inflict BODILY HARM as your punishment!" Then: "GET DRESSED!" snapped Ruby.
Cupcake did as he was told.
"Now then," Ruby said calmly but firmly when he finished. "Give me your phone!"
He handed it over. She produced a SIM card from her robe pocket, inserted it, hit the screen a few times, then ejected the card, and handed the phone back.
"There," said Ruby. I now own a copy of your entire contact list, as well as your number, of course. Here's what's going to happen. You will come here three nights a week, INDEFINITELY, for tummy tickling sessions that last no less than THREE hours. Think of it as your second job, and I, Cupcake, your more important Boss. Failure to meet just ONCE, will result in the camera footage sent to everyone on this SIM Card. IS THAT CLEAR?!"
Frightened, he stammered, "Y-yes, Miss Ruby. Anything you say, b-boss!"
"Good, go on. See you here Monday night after your day job, Cupcake!"
"Yes, Miss Ruby!" He left, regretting getting her upset in the first place.
Alone in her condo, Ruby looked forward to their next session. It was a shame he had to touch when he did. But now he's paying the price. She really did still like him. But her affection was something he needed to earn back. He would...eventually.
Last edited:
