milagros317 : 02 - The Greatest Babysitter (f/m, ff/m)

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milagros317 : 02 - The Greatest Babysitter (f/m, ff/m)

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02 - The Greatest Babysitter
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By @milagros317

Sat Sep 25, 2010 9:26 am
The following is a fictional story.

The Greatest Babysitter

Karen never wanted to babysit for Jay again. She told his mother exactly that.

“No, I don’t want to,” she said on the phone. “One time babysitting him was enough, more than enough, actually. Do you want to hear the whole story?”

“Go ahead,” said Betty, a widow aged 35, and the mother of Jay, who was 12. “All I know is that when I came home two weeks ago, you looked unhappy, Jay looked unhappy, and both of you just said ‘Fine,’ when I asked how things went.”

“Five minutes after you left, Jay asked me to play a game, and I told him I would. He left the room and came back with lots of clothesline and told me he was a robber and I was a store clerk that he was going to tie me up. I had to grab his hands to stop him from starting to tie me to the chair I was sitting in. I told him no way I was letting him play any game that involves me getting tied up.”

“I see,” said Betty.

“He looked unhappy but put the rope away,” said Karen. “Then I started to do my homework. He snuck up on me, crawling on the floor, and tickled my feet.”

“Oh, he does that to all the babysitters, if they take their shoes off,” said Betty.

“Once I wouldn’t have minded. But after I told him not to, he did it again. And then a third time. That’s when I put my shoes back on.”

“That was really naughty of him,” Betty admitted.

“You had told me not to spank him, so I didn’t, but I wanted to. After I put my shoes back on he just sulked and then disappeared into his room. I did get to do some homework undisturbed for an hour, but then I heard him coming back out of his room and saw that he had the rope again, and some duct tape, too. He admitted that he was hoping to sneak up and tie my hands before I could stop him.”

“Very unlikely,” said Betty, “that you wouldn’t be able to stop him. You must be 5 feet 10 inches tall already and he’s close to average for a 12-year-old boy, 5 feet even and 95 pounds.”

“I’m 5’11”, actually,” said Karen. “When my mother was 16, my age, she was just about my height but she wound up at 6’3”, so I guess I’ve still got some growing to do. You’re right in that I wasn’t worried about him overpowering me, but I just found it extremely annoying to have to push him away, over and over again, from tickling me or trying to tie me up. I don’t want to babysit him again and I think you can understand why not.”

“I do understand,” said Betty. “Listen, I’m desperate. I have a deal to offer you. I have a way of guaranteeing that he won’t bother at all, that he won’t be any trouble. I truly, desperately need a babysitter for all of Columbus Day weekend. You could earn about 75 hours’ pay, from Friday evening until late Monday night.”

“I could sure use the money,” said Karen. “But how could you guarantee that he won’t give me any trouble?”

“In part because I’ll give you permission to spank him,” said Betty. “And the rest you’ll see for yourself. Listen, here’s the deal. Just come over here on Friday, be here by 6p.m. sharp. If you aren’t satisfied that the situation is to your liking, then I’ll pay you for one hour and you can go home.”

“In that case I have nothing to lose,” said Karen, “it’s only a five minute bike ride to your house from ours. Why are you so desperate for a babysitter, if I may ask?”

“My husband died just over five years ago,” said Betty. “I began dating again about three years ago. This is the first time that I’ve met a guy that I really like and it’s getting serious. He’s asked me to go to the mountains with him for the holiday weekend. I’ve called over a dozen babysitters and nobody wants the job.”

“Have they babysat him before, too?” asked Karen.

“Some have and others have heard about him from them. Apparently he’s succeeded in tying up two different babysitters before, pretending it was a game, and then he tickled them insane. I never knew. I guess they were too embarrassed to complain about it at the time. They told me all about it today when I begged them to babysit Nobody wants to risk sleeping in the same house alone with him. I can’t send him to relatives, either. I don’t have any relatives living near here any more, none closer than 3,000 miles away, in California. Please, please, just come over on Friday and see for yourself what I’ve got planned.”

“I’ll do that,” said Karen, “I’ll be there at six o’clock.”

Karen rang the doorbell two minutes before six o’clock and Betty let her in. She was glad to see that Karen was carrying a duffel bag.

“That’s just in case I do stay,” said Karen, noting her glance.

“He’s been fed dinner already,” said Betty, “and all the meals you’ll need are in the big freezer in the basement. I’m already packed and ready to drive to meet Samuel at his house.”

“Just a moment,” said Karen. “I need to see whatever you claim is a guarantee that Jay won’t be trying to tie me up, sneaking up on me and tickling me, or coming into my room at night while I’m asleep with rope and duct tape.”

“Come with me,” said Betty.

Karen followed her upstairs to Jay’s bedroom. Once they were in the room, Karen couldn’t help but laugh and laugh at the sight of him. Betty laughed as well.
Jay was tied up on the floor, on a big puppy pad that had been placed on the rug. He was lying on his belly. Half a dozen coils of rope, cinched, held his right wrist to his left elbow, behind his back. His left wrist was similarly attached to his right elbow. His forearms were tied together as well, and that rope went around his chest, holding his arms close to his back.

His legs were tied together at the upper thighs, above the knees, below the knees, at the calves, and at the ankles. His ankles were bent back and a separate rope attached them to the ropes around his forearms. It was quite a strict hogtie. He was wearing a green t-shirt and blue jeans and his feet were bare. His big toes were tied together with a shoelace.

An ace bandage was wrapped around his head, keeping something out of sight firmly in his mouth. He was blindfolded with a black wool muffler.

Jay, hearing the laughter, grunted through his gag.

“After talking to the two babysitters that he tied up and tickled,” said Betty, “I’ve decided to let his punishment fit his crime. He tickled both of them until they wet themselves. The puppy pad is so he won’t stain the rug and there are more of them in a big gray box in the garage. You should know that he’s extremely ticklish, dreadfully ticklish, especially on the bottoms of his feet.”

Jay grunted loudly through his gag.

“You shut up, young man,” said Betty. “Let me tell Karen how this is going to work, and you listen so that you’re reminded, too, of what I told you earlier. He stays tied up all weekend, Karen. Even when you let him go to the bathroom, his legs stay hobbled. There are padded wrist and ankle cuffs, comfortable enough for sleeping, to tie him to the four bedposts overnight. They have padlocks. During the day, he’s only to be ungagged when you feed him. If he gives you any trouble at all, if he disobeys you or even talks back to you while obeying, then give him a spanking, a long and hard spanking. He’s to submit to being tied up again in any position you dictate, at any time, at your orders. Nod your head if you understand me, Jay William.”

Jay, knowing that his mother used his middle name only when she was deadly serious, nodded his head.

“I do believe that the situation is to my liking,” said Karen with a grin. “So I think that I will take the job and stay for the weekend.”

“Excellent,” said Betty, “I’ll be driving off now then. Don’t forget how dreadfully ticklish he is, Karen, and how he needs to be taught a lesson.”

“I’ll do my best,” said Karen. “Enjoy your weekend.”

Hearing the car drive away, Karen kicked off her loafers, leaving her lovely size 11 feet bare. She walked over to Jay and poked his nose with her toes.

“You’re in quite a pickle, Jay,” she said. “That rhymes with tickle and you’d probably like to tickle that bare foot of mine that’s poking you in the nose right now. But you won’t get to do that. I’m going barefoot all weekend, but all that you will ever do is sometimes be able to look at my feet, never touch them. How sad for you. On the other hand, your own bare feet seem to be sticking up in the air, helpless. And your rib cage is quite exposed, too, except for a few ropes here and there. How amusing.”

Sitting on the floor near him, Karen bent back his toes with one hand. The fact that his big toes were tied together made that easier. She began with just one finger of the other hand, stroking from his heel to the base of his toes, over and over again.

Jay began to giggle and then to laugh audibly through his gag. Karen began to use two fingers and then three. Jay laughed louder and squirmed. He could barely wriggle in his ropes. Karen progressed to all five fingers and began to tickle faster. She glanced at her watch for a moment to note the time when she began the all-out tickling. Jay howled through his gag.

“I can hear that you mother hasn’t packed enough into your mouth before putting that Ace bandage around it,” she said. “I’ll have to remedy that after your first round of tickling, but don’t worry, that won’t be for quite a while.”

Jay was not reassured by the mention of a ‘first round’ nor by the estimate of its length. He was in tickle hell, unable to defend himself or move away. All he could do was lie there and laugh, hoping that Karen would eventually show mercy.

Instead of showing mercy, she explored every part of his sole, noting which areas were most ticklish. His very worst spot turned out to be the center of the ball of his foot. Digging her fingernails in there drove him crazy.

After twenty minutes by her watch, Karen paused and let him catch his breath. She waited about a minute before shifting her position seated near him to better get at his ribs. She dug into his rib cage on both sides, with all ten fingers.

“Now that I’ve seen that your mother was right about your feet, I’m testing your ribs,” she told him.

Jay began to buck and squirm again, but could hardly move at all. Karen kneaded her thumbs into his ribs for a while, noting that he howled when she did that. She found that his collarbones and neck were ticklish as well. She returned to his ribs, kneading each one separately to find his most ticklish spot. She smiled as she noted that the fourth rib from the bottom on each side was a golden tickle spot, one that he could hardly bear. He did bear it, however, as she put her thumbs on those spots on both sides and dug in, over and over and over again. She could see that his blindfold was wet with tears when she paused again to let him breathe freely.

“Catch your breath, Jay, while you can. I’ve hardly begun to tickle you, you know. I wasn’t sure I’d be staying here so I ate an early dinner at home. I don’t need to eat and you’ve been fed, so I don’t see any need to change your position any time soon. You’ve had enough of a break, think.”

With that statement she dug into the golden spots on the fourth ribs and smiled as he began to howl all over again. She tickled without a pause and began to taunt him.

“Poor little baby Jay! So ticklish, so very ticklish and so very helpless. All tied up and not about to escape, hogtied and barefoot, utterly helpless. Poor little ticklish baby! Did you know you were very cute like this? Yes, you’re just a cute little helpless ticklish baby boy, all mine. All mine to tickle and tickle and tickle, just as long as I want to. How sweet! Your mother didn’t tell me the names of the two babysitters that you tricked into letting you tie them up, but I’ll bet they wish they could be here now. That gives me an idea for tomorrow, actually. Poor ticklish baby! I’m going to drive you insane with tickling.”

When Karen could hear that he was having trouble breathing, she stopped. She waited patiently until his breath seemed normal.

“Time to gag you better,” she remarked, getting up and removing the Ace bandage from his mouth. She pulled out a thin handkerchief that had been rolled up inside of it. She also removed his blindfold.

“No wonder you were making so much noise through your gag,” she said. “You definitely need a more substantial gag. I’ll be right back.”

Jay didn’t answer; he was still panting but had stopped crying.

Karen got a pair of thick gym socks from her duffel bag. She also got two regular toothbrushes, two electric toothbrushes, and two hairbrushes with plastic bristles from the upstairs bathroom.

“I need water before you gag me again,” said Jay.

“That’s not a polite way to ask,” said Karen. She stuck her right foot under his chin. “Kiss all of my toes and ask politely, then you may get some water.”

With some difficulty Jay was able to move his head enough to kiss each of her toes. “Please may I have some water?” he asked. “I’m very thirsty.”

“Of course,” she said. “All you had to do is ask politely. I’m here to take care of you, after all.”

Karen left the room and returned with a bottle of water and a straw. She knelt down and carefully turned him over on his side. Then she propped up his head and fed him the whole bottle of water.

She stood up and placed the bare sole of her left foot against his mouth.

“Kiss ten times and then thank me,” she said.

Jay kissed her sole ten times with closed lips and then said, “Thank you so much for the water.”

“You’re very welcome,” said Karen.

She stuffed an entire thick gym sock into his mouth. Then she re-wrapped the Ace bandage around his head, firmly holding the sock in his mouth. She replaced his blindfold.

“That will be a much better gag than the little handkerchief your mother used,” she noted. “And you’re lucky it’s clean. Tomorrow I’ll have soiled gym socks to use after my jogging.”

Jay winced at that statement as she rolled him back onto his belly. She checked all the ropes and took the time to tighten some of the knots.

“Ready for round two of your tickling?” she asked brightly.

She experimented on his bare soles with the regular toothbrushes, the electric toothbrushes, and the hairbrushes. She found that the toothbrushes of either type were devastating between his toes, it drove him mad to have them rubbed there. But even better was scrubbing a hairbrush on that perfect spot in the center of the ball of his foot. He practically levitated off the floor when she did that‘”clearly it tickled him out of his mind.

Karen grinned and used the hairbrush on first one foot, then the other, then back to the first, always using her other hand to hold back his toes. His sobbing was harder than before as he was laughing so hard that he couldn’t hold back the tears.

“Poor little baby boy,” she taunted him. “So very ticklish on your soles and so very helpless. I wonder where your mother learned such good bondage techniques. No matter, I’m quite good at tying people up, too, I have four younger sisters. Tickle, tickle, tickle, little baby Jay! I’m going to tickle you until you pee in your pants.”

Lost in the joy of tickling him insane, tickling his defenseless soles relentlessly, she never even noticed when he did wet his pants. She only noticed the smell a few minutes later.

“Wise of your mother to use the puppy pad,” she said, without pausing in her relentless tickling of his soles. “I’ll get a new one from the garage later to put under you on your bed tonight.”

With just a few more pauses for Jay to catch his breath, Karen tickled him without mercy, remembering that he needed to be taught a lesson, remembering what he had done to two previous babysitters and been plotting to do to her the first time she babysat for him. Finally, seeing it was 9:30pm, she stopped.

Karen got up and removed Jay’s gag and blindfold. Leaving him hogtied, she went to use the bathroom herself.

“Listen, Jay, that was a lot of fun for me, tickling you for hours, watching you squirm and laugh and even wet yourself,” she said upon returning to his room. “Not so much fun for you, I bet.”

Jay, now back to normal breath and face color, just said, “Right.”

“I’ll make you a deal,” said Karen. “No need to do what your mother said, leave you partially tied to use the bathroom, if you promise me to behave yourself. I’ll put your pajamas in the bathroom, untie you, and walk with you there. I’ll close the window first. I’ll be listening right outside the bathroom door, which will be open one inch, I’m not a fool. If I hear you open the window or see you close the door, then I’m coming right in. But behave and you can have privacy to shower and use the toilet. Otherwise you’ll be partially tied up and have no privacy. What do you say?”

“Yes, thank you, I promise to behave.”

Jay kept his word and behaved himself, showering and brushing his teeth and then putting on his pajamas in the bathroom with Karen just outside. She kept her word and didn’t peek.

When he emerged she told him to go to his room and lie on his back on his bed with all four limbs outstretched. She followed him in there.

She locked the two padded leather wrist cuffs around his wrists with padlocks. She tied them, via their D-rings, to the bedposts at the head of his bed, securely but with a few inches of slack so that his arms weren’t strained.

“Keep still while I get a new puppy pad,” she said.

She got one from the garage and brought it upstairs. She put it under him on the bed. She locked both padded leather ankle cuffs on his ankles with padlocks. She tied them, via their D-rings, to the bedposts at the foot of his bed, also with a few inches of slack so his legs wouldn’t cramp during the night. She put a top sheet and a blanket over him, leaving his head and arms sticking out at one end and his ankles and feet at the other.

Karen pulled a chair over to the side of his bed. She kissed him on the forehead, very tenderly, and sat down. She spoke softly to him.

“You know why you’re being punished, Jay, because you can’t resist tying girls up and tickling them. That would be fine if they liked it or gave you permission, but it’s not right if you force them or trick them. Your mother has decided your punishment is to fit the crime. That is, you’re going to be tied up and tickled yourself, all weekend. I won’t pretend it’s not fun for me, it is. But I will always be careful to keep track of your breathing, and give you breaks to catch your breath. I’ll tie you so as not to cut off circulation, and let you have water and food when you need it. In return, I expect you to be very well behaved and, above all, obedient. I’m a very strong young woman and I don’t want to have to spank you hard, the way your mother said I should if you even think of disobeying me. Do you understand?”

“Yes, Karen,” said Jay. “Please don’t be too hard on me, I’m dreadfully ticklish.”

“So I noticed,” said Karen. “Well, I might be disposed to be kind to you if you show me how much you appreciate it. I was disappointed the way you kissed my sole when I told you to kiss it to thank me earlier tonight.”

“But I kissed it ten times just like you said,” replied Jay.

“You did, but with closed lips,” said Karen. “To show me that you appreciate my kindness and that you like me, I want to feel your tongue. In fact, it would be better if you kissed my feet the way a nice, friendly puppy would, by licking them.”

Still sitting in the chair, she extended her left foot to his head, the sole at his lips. He began to lick her foot, along the whole length of the sole, from her heel to her toes.

“That’s a good boy,” she said, “such a good boy! Now start counting to yourself, not out loud, and give me a hundred licks beginning now.”

When he stopped, she extended right leg, putting her sole to his lips. She was pleased that he began licking without being prompted to do so, and licked a bit more than the full hundred times on that sole, too.

Karen stood up and checked the four padlocks and the ropes. She once more kissed him on the forehead, very tenderly.

“Good night, my sweet little ticklish baby boy. We’ll have such fun tomorrow!”

Note: This story will be continued if there is interest.

Sun Sep 26, 2010 10:44 am

On Saturday morning, Jay woke up abruptly when Karen sat on his legs and began to tickle the soles of his feet. She did it lightly, playfully, not at all like the extreme tickling he had gotten the day before.

“Wake up, sleepyhead,” she said, still tickling his feet. “It’s past 8 o’clock and time for you to get out of bed.”

She got up from the bed and sat down in a chair near it.

“I’ll make you a deal. I’ll unlock these cuffs and let you go the bathroom yourself, shower, and get dressed, put on clean underpants, blue jeans, and a t-shirt, all by yourself. I’ll trust you, in other words. But you have to promise to be the most obedient, well-behaved boy I’ve ever seen, all day, while I tie you up any way that I want to. Agreed?”

“Yes, Karen,” said Jay. “May I please lick your feet again to seal our agreement?”

Karen laughed. “I thought you were enjoying that,” she said. “Sure, go right ahead.”

She raised her left leg and put her sole on his lips. He licked and licked, one hundred times. She changed legs and he did the same to her right sole.

Karen got up and unlocked all four cuffs, freeing his wrists and ankles. She left the cuffs tied to the four bedposts by their D-rings, which Jay correctly took to mean that he would be bound to his bed again when night came.

When Jay came downstairs he went right into the kitchen. One of sturdy wooden dining room chairs was at the kitchen table, with a large supply of rope nearby on the counter. There was a puppy pad on the seat of the chair. Without a word, he sat down in that chair and put his arms on its wooden arms.

“Very good,” said Karen. “That’s exactly where you’re going to be tied for breakfast. I’ve already eaten, so I’m going to tie you to that chair, very securely, and then feed you. Also, I’m glad to see that you’re barefoot. Those very sensitive feet of yours are going to get quite a work-out today.”

Karen began by tying his wrists to the arms of the chair and then also his elbows. Checking that those knots were secure and out of the reach of his fingers, she nevertheless wrapped duct tape around his fingers, rendering them useless. She tied a longer rope intricately around his upper arms, his chest, and the back of the chair, pressing his back firmly into it. She then tied his waist to the back of chair, quite securely.

Karen tied his legs together at the thighs, just above his knees. She then tied his now joined thighs to the seat of the chair. She wrapped duct tape around his thighs and the seat of the chair, hiding these ropes and making his bondage more secure.
She tied his legs together below the knees and at the ankles. A final rope around his ankles was used to pull them back well under the chair. She secured this rope to one of the back legs of the chair and then tied his ankles to the other back leg as well.

“I’ll allow you to see while I’m feeding you,” she said. “And I notice that you’re looking down to sneak peeks at my bare feet. Do you think that they’re pretty?”

Jay blushed as he answered, “Yes, very pretty.”

Karen laughed. “If you’re a very, very good boy, the best behaved boy in the world, then I might allow you to kiss them and lick them again later. But only if I want to.”

She sat down in a kitchen chair next to him and fed him the scrambled eggs and toast that she had made, along with some orange juice. She wiped his mouth carefully afterward.

She picked up the sturdy chair, with him still tied in it, and carried it into the living room.

“Wow, you’re really strong,” said Jay as she put him down right under a hanging plant whose pot hung down from a large metal wall bracket near the ceiling.

“I play basketball in the fall and winter, tennis in the spring, and go canoeing in the summer,” said Karen. “That keeps me fit, along with my jogging. I jog all year round. Which reminds me, I need to put on my athletic socks and jogging shoes.”

Leaving him tied there, Karen left the room and went upstairs to the guest room where she was staying. She returned wearing white socks and size 11 Nike running shoes. She had put her long blonde hair back into a ponytail, too, he saw. She was also carrying the same white sock and Ace bandage she had used to gag him the day before.

“My clean sock dried out overnight after being in your mouth so long,” she remarked.

Jay opened his mouth without even being ordered to do so and Karen smiled at that, stuffing the sock in and securing it with the Ace bandage wrapped around his head.

He was quite surprised when she untied his wrists, elbows, and arms. He used the relative freedom to rub his own wrists. She made no comment but left the room and returned with a kitchen chair that she placed beside him.

Standing on the kitchen chair, she removed the potted plant from where it hung. She climbed down and put it on the coffee table. He began to understand what was going on when she tied his wrists together securely, stood up on the chair again, and ordered him to raise his hands high above his head.

When he complied, she tied them to the metal bracket that had held the hanging plant. She left only about an inch of slack so that his arms were stretched up severely. She tied his elbows towards each other; he wasn’t flexible enough to get them to touch.

“That hogtie you were in yesterday,” said Karen, grinning like a cat contemplating a trapped mouse, “was a fine position for tickling your soles, but it didn’t afford much chance to get at your armpits.”

Jay’s eyes went wide even as she blindfolded him with the black wool muffler. He tensed and waited for the assault to begin under his arms. He didn’t have to wait long; soon Karen was wiggling just one strong finger in each armpit. Then two fingers in each, then all five, wiggling furiously.

Jay howled with laughter through his gag. He wriggled and struggled but couldn’t move at all in the chair tie. He howled and laughed, and laughed even more. He was again in tickle hell, unable to move or defend himself in any way, totally at her mercy.

Twenty minutes into the tickle torture, when she could see tears soaking the blindfold, when she could hear him breathing with difficulty, Karen showed mercy. She stopped the tickling and listened to him pant and regain his breath.

The doorbell rang and Jay tensed up.

“Don’t worry,” said Karen, stroking his cheek affectionately. “That’s just two of my sisters. They know all about this, I talked to them on the phone last night after I put you to sleep.”

Jay could hear Karen walking to the door and opening it. He heard laughter from other young women as well as from Karen. He heard footsteps approaching him. He felt Karen stroking his cheek again, just above the Ace bandage.

“It’s just my sisters, Kerry and Kelly. I can’t leave you alone all tied up like this, can I? I’m your babysitter and I must be sure to keep you safe, always.”

She paused to stroke his cheek yet again and then kiss his forehead just above the blindfold.

“I will always keep you safe, my dear little bondage toy, my dear little ticklish captive,” she said. “Kerry and Kelly will look after you while I do my jogging. I’ll be doing ten miles today so they will likely amuse themselves by tickling you.”

“We’ll tickle you insane!” said Kelly.

“That we will!” said Kerry.

“You must give him a five minute break after every 20 minutes of tickling,” said Karen. “I don’t want to come back here and see him blue in the face, understand?”

“Sure, Karen,” said Kerry. “I’m the older one so I’ll be in charge and I’ll keep the time.”

“By all of ten minutes,” muttered Kelly, used to this treatment.

“The twins are 14,” said Karen to Jay, “in case you were wondering. By promising to let them tickle you, I don’t even have to give them any of the babysitting money I’ll be getting. I may go home after I’ve jogged and shower there, and take care of some things. But I’ll be back to feed you lunch, my little bondage baby.”

With a final kiss on his forehead, Karen left him in the care of the twins.

Kerry tickled under his arms, taking the standing position where Karen had been. Kelly got down on the rug and attacked his bare soles, digging her fingernails in with enthusiasm. Jay howled and screeched with laughed, making considerable but unintelligible noise even through the thick sock gag.

Soon they could hear him crying again, laughing so hard that he was sobbing.

It was during his third break, after he had wet himself and soiled the puppy pad, that Kerry imitated her older sister and stroked his cheeks.

“Don’t feel bad,” she said, “of course you couldn’t hold it in forever. Karen has tickled us until we peed more than once, too. You’re really kind of cute all tied up like this. I think I like you. I wonder if you know our younger sisters, Katherine and Kristine. They’re also twins, your age, 12, so you might be in their class at St. Bart’s.”

“No, stupid,” said Kelly. “He goes to public school, not St. Bart’s. Let’s change places. I want to get his armpits and you can get his feet.”

“OK,” said Kerry. “But I want to find that hairbrush. Karen said that’s better than fingernails for tickling his feet.”

Kelly stood up and dug into his armpits with gusto. Kerry, after returning with the hairbrush with the plastic bristles, attacked his bare soles vigorously. Soon he was laughing so hard that he was sobbing, again.

Karen arrived back at the house at noon, having changed into blue jeans and a different t-shirt in her own house after jogging. She removed her shoes and socks at the door and luxuriated in rubbing her bare feet into the rug.

Kelly and Kerry stopped tickling Jay and greeted her.

“I see we did need the puppy pad,” said Karen.

“Yeah, he wet himself at least twice,” said Kerry. “But don’t worry, we always gave him a break, after every 20 minutes of tickling. He’s really cute, especially all tied up and helpless like that.”

“Yes,” said Karen, “I thought that he’d be a good first boyfriend for Kristine. She likes the cute boys she can boss around, not the macho boys.”

“Maybe we should take him home as a gift for her,” said Kelly.

“No, I don’t think his mother would approve,” said Karen. “You two run along home now, but be back tomorrow morning at the same time, and Monday morning, too. I need you here every day when I do my jogging.”

Kelly and Kerry both hugged Jay and they kissed his cheeks above his gag.

“We had so much fun playing with you, Jay,” said Kerry.

“Yes, it was the best tie-up game ever,” said Kelly.

“We’ll be back for more tomorrow and Monday,” said Kerry.

Jay heard their footsteps and then heard the front door close as they left.

“They really like you,” said Karen, “and why not, you’re the best little ticklish bondage toy that any girl could want.”

Karen brought over a kitchen chair again to untie his hands and restore the hanging plant to its rightful place. She carried his chair back to the kitchen.

“There’s microwave pizza that your mother left for lunch today,” she told him. “I’m going to take off your blindfold and gag now and even leave your arms untied so you can eat the pizza yourself.”

“Thank you, Karen,” said Jay.

After lunch, Karen began to untie Jay from the wooden chair he’d been in all day.

“Listen,” she said. “You’ve proved that I can trust you. So here’s what you’re going to do once I’ve untied you. Put the soiled puppy pad in the trash can in the garage. Get three new ones from the box there and put one on the floor in your bedroom, I’m going to hogtie tonight after dinner and tickle you there. Put one on your bed for overnight. Put the third one on the living room floor, we’ll be using that one soon. Put your clothes in the laundry hamper in the bathroom, take a shower, and put on clean clothes. Then come back downstairs and lie on your belly on the puppy pad on the living room rug.”

Now untied, Jay followed all of her instructions to the letter. She eventually saw him lying on his belly as instructed, wearing new jeans and a new t-shirt.

Karen hogtied him there, very securely, exactly as his mother had on Friday. Then she turned him on his side, belly and face towards the easy chair in the living room. She moved the chair near him and sat down.

“I have a treat for you this afternoon,” she said. “I have lots of reading to do for my history course, I’ve neglected it and there’s a test on Wednesday. I’m going to leave you with no gag and no blindfold. While I read, I’m going to use you as my footstool. Sometimes your belly, sometimes your side, and sometimes, when you’re really lucky, your face. You may stare at my lovely bare feet. When I put one on your lips, you may lick it. I hope you realize how kind I’m being to you.”

“Yes, Karen,” said Jay, with genuine enthusiasm.

“And not a peep out of you, I need quiet for my reading,” she added.

It was the greatest afternoon of Jay’s life, he decided, being used as a stool for the loveliest pair of bare feet he’d ever seen, with occasional chances to lick them.

After dinner, with Jay in the same strict hogtie on the floor of his bedroom, Karen grinned down at him.

“This evening’s surprise may not be as welcome as this afternoon’s,” she said. “Open wide.”

He did so and winced at the acid taste of the used, sweaty sock that was thrust into his mouth. Karen laughed.

“That’s one of the socks I wore jogging today,” she said. “I even turned it inside out so that the part that was pressed against my sweating feet is now against your tongue.”

She secured the sock firmly in his mouth with the Ace bandage and then blindfolded him.

“You had the whole afternoon off from being tickled so I have no guilt in tickling the crap out of you now, over and over again, until your bedtime. And I have one more surprise for you. Remember that hairbrush that really drives you crazy on the ball of your foot? I used it last night and Kerry used it on you this morning. Well, I bought another one, just like it, in the pharmacy today. So I can do it to both of your soles at the same time.”

As good as her word, Karen indeed tickled the crap out of him, over and over again, but with the mercy of a break after each 20 minutes of tickle torture. She was exhilarated by the time it was 9pm and she decided to get him ready for bed. He was exhausted, tickled out of his mind, once again having wet himself.

When he was in the four padded cuffs and tied down to the bed again, Karen sat in a chair near the bed and spoke with him.

“Did you have fun today?” she asked.

“Yes, Karen,” he answered.

“Even when my sisters tickled you out of your mind? Even when I did the same?”

“Yes, Karen. It does drive me crazy to be tickled so much, but I still like it somehow. I still would be disappointed if you didn’t do it. It’s punishment in a way, but I want it, too. Please do it again tomorrow and Monday. Please tie me up and tickle me insane, over and over again.”

“I will certainly do so, and my sisters will be back, too, don’t you worry. I’m going to let you lick my soles now, just because I like you, you’re the sweetest little bondage toy that I could want, and so very ticklish, too.”

After the ritual of allowing him to lick each sole one hundred times, Karen kissed him tenderly on the forehead and left his room.

Two days later, on Monday, Columbus Day, at the same time, with Jay in the same position in the four leather cuffs, tied to his bed, Karen asked him a different question.

“Now that the long weekend is over, now that your mother will be home in about an hour to untie you, what do you think of me as a babysitter? There’s nothing I can threaten you with now, you have no reason to lie to me.”

“I think you’re the greatest babysitter in the whole world!” said Jay with enthusiasm.

Karen laughed, pleased at his obvious sincerity.

“You may have double the usual number of licks, then,” she said, putting her left sole against his lips. “Two hundred on each sole.”

“No trouble at all? None? Really?” asked Betty, two hours later, having gotten home a bit later than planned.

“Absolutely no trouble,” said Karen. “I didn’t need to spank him, not at all. He’s become quite the obedient little boy.”

“That sounds like a miracle,” said Betty. “How would you like to be my regular babysitter from now on? Samuel and I had a fabulous weekend. We’ll be going out together very often now, and I’ll staying overnight at his place most of the time when we do.”

“It will be my pleasure,” said Karen, with genuine sincerity, thinking of all the fun she would have with her very cute, very obedient, and (most importantly) very ticklish little bondage toy.

The End

milagros317's stories
Index of all stories in the "Archive for Everyone" section
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Post by milagros317 »

Thank you for re-posting this story from the old site. :D
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Post by Nathaniel1998 »

Love this story 😍
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Post by IvyCoveredWalls »

I was the youngest of 13 children. Never needed a baby sitter. Poor Me.
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Post by jone123 »

Thanks for posting the story.

I really loved the forehead kissing thing while tied up. It always a nice gesture from the dominant person.
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