Adventures In Babysitting 20 min read

A fantasy about the first time being trampled by a babysitter

written by underwife
original source of the story was Mistress Destiny's Femdom Forums

Julie walked up to the door and rang the bell. Mrs. Clark came to the door and greeted Julie in her usual fashion.

“Hi, Julie. Thanks for coming over on such short notice,” she said with a relieved look in her eyes.

“Oh, it’s OK Mrs. Clark. Billy had to cancel a date tonight cause he had a test he wanted to study for. I had nothing better to do,” Julie shrugged her shoulders as she spoke.

“You’re dressed up dear, do you want to go home and change?” Mrs. Clark asked.

“No, no. I don’t want you to be any later than you already are. Just go and have a good time OK?” Julie said.

Julie was planning to go on a date with her boyfriend Billy. They had been dating for two years now. Billy was a freshman at the local community college and Julie was a senior in high school. She was wearing a simple pleated black skirt that ended just above her knees. She was wearing a white blouse that was neatly tucked into her skirt and a jacket that matched her skirt. She was wearing tan colored pantyhose and simple low-heeled black shoes. Her medium length soft brown hair was pulled back with a headband that made her hair fall loosely down the back of her neck.

“Well, come on in. I’ll be gone for about three or four hours. Here’s some money so that you can get a pizza. Matt is upstairs playing video games. I’ll see you when I get back,” Mrs. Clark said as she walked out the door.

Julie had been babysitting for the Clarks for about 3 years. Their son Matt was a good kid and was never a problem to take care of. Matt was a little older now but not quite old enough for his parents to feel completely comfortable leaving him alone to go to bed on his own. They would leave him for an hour or two during the day but not at night like this.

Julie walked inside and put her purse on the table. She slipped off her jacket and laid it across the chair and then bounced upstairs to see Matt.

“Hey Punk,” she said playfully to him as he lay on the floor playing video games. “Whatcha playin’?” she asked.

Matt didn’t even look up as he tried to blast the bad guy. “Alien Attack 2,” he said hurriedly.

“Your Mom left money for pizza. Are you hungry?” she asked.

“Yeah,” he answered.

“What kind of pizza do you want, you video head?” she asked.

“I don’t care,” he answered again without looking up.

“OK, sardine, anchovy, mushroom, and onion it is!” she said laughing as she turned to walk away.

“No!!!” Matt yelled as he scurried to his feet. He ran out of the room and chased Julie down the stairs. When he caught up to her he leaped into the air and tackled her from behind. Julie laughed as she fell to the floor and acted like Matt was crushing her.

“Please let me up Mr. Alien! I can’t breathe! You’re crushing me!” she said laughing.

“Now I’m going to suck out your brains!” Matt said in an alien voice.

“No, no, please don’t suck out my brains!” Julie laughed.

Just as Matt leaned in and pretended to start sucking out Julie’s brain she flipped Matt off her back and straddled his stomach, pinning each hand under her knees. He started to flail wildly as he tried to dismount her but she just laughed as she started to tickle him. She was to heavy for him to move.

“Give up?” she asked.

“Yes! Please stop!” Matt pleaded through his laughter.

Julie stopped tickling Matt and sat on his stomach for a second. “Now, what kind of pizza do you want?” she asked.

“Pepperoni,” Matt answered. “But you’re not allowed to eat any,” he said.

“What? Why?” Julie asked.

Matt turned his head to the side and stuck out his tongue as if he was choking. “Cause you weigh a ton!” he gasped.

“Augh! You brat! I don’t!” Julie yelled at him.

Matt pretended to gasp, choke, and gag as he said, “Please! You’re killing me! Get off!” Then he went limp, as he played dead.

Julie gave him a disgusted look. “I’ll show you!” she said as she started to bounce up and down on his stomach. “How’s this feel, you little punk?” she asked as she bounced on him.

Matt smiled as she bounced harder and harder. He was secretly enjoying having Julie on top of him.

“Is that all you got?” he taunted.

“Oh no. That’s definitely not all. But I don’t want to hurt you,” Julie said with a grin.

“I’ll bet you could stand on me and jump up and down without hurting me!” Matt said confidently.

“Well, I doubt that,” Julie said as she started to get up off of Matt. As she stood up Matt grabbed her ankle and placed her foot on his chest.

“Try it!” Matt said almost pleadingly.

“No. Now let go so I can order the pizza.”

Matt begrudgingly let her go and got up himself. He went to sit on the couch and turned on the TV. Julie ordered the pizza and sat on the other end of the couch. There was a tension between the two and they didn’t speak as they watched TV.

The doorbell rang and Julie went to answer it.

“Pizza’s here,” she sang out to Matt as she put it on the table. Matt came over and they each ate several slices in relative silence. Matt went back to the couch and Julie followed after putting the pizza away.

“Are you mad at me, Matt?¨ she asked him.

“No. I just don’t like that you think of me as a kid,¨ he said. Julie just kept watching TV. After about 10 minutes she looked over at Matt.

“Do you really think you can handle being stepped on?¨ she asked.

Matt’s eyes lit up. “Of course,” he said confidently.

“Seriously?” Julie asked again.

“Yep,” Matt said as he puffed up his chest.

Julie stood up and pushed the coffee table away from the couch. She sat back down again and pointed to the floor at her feet as she looked at Matt. Matt was on the floor in an instant.

“Better take off your shirt so I can see where I’m stepping,¨ Julie said.

Matt peeled his T-shirt off and threw it to the side. Julie kicked off her shoes and put her perfectly shaped feet on his chest and rubbed a little.

“Your feet are so soft and warm,” Matt said with a little tremble in his voice as he reached for her feet.

Julie kicked his hands away and said, “I didn’t say you could touch. Rugs don’t move,” she said. “Are you nervous?¨ she asked as she saw Matt trembling a little.

“Yes,” he said matter-of-factly.

“Well, at least your honest,” she said. “Have you ever kissed a girl’s feet before?” she asked him.

Matt shook his head no. Julie slid one foot up Matt’s chest and placed the ball of her foot on his mouth. Matt immediately began to kiss her foot passionately.

“Stick out your tongue,” Julie said.

Matt opened his mouth slightly and stuck out his tongue as he was told. Julie put one foot across Matt’s eyes so that he couldn’t see and then started rubbing the other foot all over his tongue. “Do you like that?” she asked.

“Uh, huh,” he responded as she pinched his tongue with her pantyhose covered toes. “Now open really wide for a nice surprise,” she sang out.

Matt opened his mouth and Julie slipped her toes into his mouth. “Wider,” she said. “I want all five toes in your mouth at once.”

Matt opened as wide as he could as Julie forced her toes deep inside his mouth. “If you want me to step on you, you have to earn it,” she said as she started to mouth fuck him with her foot.

Matt lay there thoroughly enjoying his torment. Julie pulled her foot from his mouth and placed it on top of his obvious hard-on. “You like my feet?¨ she asked as she rubbed her foot on his bulge.

“Yes,¨ he said.

“Why?” she asked.

“Because they’re so soft and smooth,” he said meekly.

“Do you want me to step on you?” she asked.

“Yes,” he whispered.

“Are you sure?” she asked again.

“Yes,” he whispered.

“If you tell anybody about this I’ll kill you! I’m serious!” Julie said sternly.

“OK,” Matt said.

Julie squeezed Matt’s head between her feet and turned his head so that she looked into his eyes. “I’ll never come over here again if you tell a sole. Get it?” she asked.

“Yes,” Matt said.

Julie stood up and straddled Mat’s chest so that she had a foot on each side. Matt gave her a reassuring smile. Julie placed one of her feet on Matt’s chest and started to slowly press down as she applied her weight.

“Tell me if I hurt you,” she said. She applied more pressure until she was standing full weight on her foot. She quickly brought the other foot to rest next to her first so that she was standing full weight on Matt’s chest. Matt held his breath as Julie stood there for a few seconds before stepping back down.

“You OK?” she asked. Matt nodded.

“More?” he asked.

Julie stepped back up onto his chest surer of herself this time. Matt smiled as Julie started to walk in place a bit as she crushed Matt beneath her perfect feet. Julie started to walk in place with a steadier pace and stepped down harder and harder with each passing moment. Matt grunted slightly from the pressure and constant pounding of Julie’s feet. Julie stopped walking in place and looked down at Matt.

“I like having you under my feet. I like crushing your helpless body beneath me,” she said with a smile.

“I like it too,” Matt gasped.

“Having trouble breathing?” she cooed.

“A little,” he responded.

“Well, you asked for this. So I think it’s not really my problem. Is it?” she asked. Matt shook his head no.

Julie stomped on his chest as she screamed, “Answer me!”

“No,” Matt gasped.

“That’s better,” she said as she started to march in place on his chest again.

After several minutes of marching in place, Julie stopped again and looked back down at Matt. She put the toes of one foot on his mouth and lifted her skirt with her hands.

“Do you like my legs, Matt?” she cooed as she flexed her calf and thigh muscles. Matt nodded. “Wanna see me arch my soft feet and flex my calves for you?” she teased. Again, Matt nodded.

Julie stood back on his chest, turned around so that she was facing his bulging penis, and stood on her tiptoes. The sudden increase in pressure caught Matt off guard and he moaned out in pain. “MMMM”

“Yessss, that feels good doesn’t it?” Julie moaned out as she marched on her tiptoes atop Matt’s helpless body.

Julie tiptoed down Matt’s body and started driving her soft pantyhose covered toes into his soft gut. Matt moaned out in pain as he grabbed Julie’s ankles. Julie ignored his moans and grasping hands as she continued to kneed her toes deeper and deeper into his gut.

“Am I mashing your poor guts? Can’t you handle it? I thought this is what you wanted,” Julie said as she continued to pulverize Matt’s guts under her toes. “I should’ve worn my high heeled pumps tonight,” Julie said. “I’ll bet you would love them. They’re shiny and black and have a thin pointed heel that would go right through you,¨ she said. “Maybe I can find something in your Mom’s closet. What do you think?” she asked. Matt only moaned.

“Maybe I could just jump on you. What about that?” Julie asked. Julie tiptoed back up Matt’s body to his chest where she stood on her tiptoes right on his nipples. She wiggled her toes and started to bounce up and down a little. Matt yelled out in pain. “Oh, please, shut up!” Julie said as she put one foot on Matt’s mouth. “Maybe I should stand on your face,¨ she said as she pressed down on his mouth with her foot. “Can you handle it if I stand on your face?” she asked mockingly. Matt knew he couldn’t stop her if she wanted to do it, and secretly, he wanted it too.

Julie lifted her foot from his mouth and placed it on his face so that the ball of her foot was on his eye and her heel on his mouth. “I hope you’re ready for this!” she said as she lifted her other foot and brought it to bear next to the first.

Matt lay motionless for only a second before his hands shot up to Julie’s soft ankles. He grabbed tight and tried to lift her from his face. She giggled at his attempts to move her. Matt began to moan and flail about as he tried to dismount Julie from his face. He had always wanted to know what it felt like to be trampled, but now that his fantasy was a reality; he was having serious second thoughts. His ears began to ring and he started to see stars from the pressure of Julie’s feet on his eye sockets. He started to moan with every breath. Julie finally stepped down off of Matt’s racked body.

“How was that my little trample boy?” she asked. Matt just lay there rubbing his aching face. “Get up!” Julie said, “We have work to do upstairs.”

Julie walked over to the stairs and yelled at Matt to hurry up. Julie looked down at Matt’s reddened chest, stomach, and face and smiled. She was enjoying trampling him and wanted to do it more. “On your hands and knees,” she said.

“I don’t want my sexy little feet to touch these stairs at all. When I take a step up I want you to put your hand under my feet so that I walk on your hands all the way up the stairs understand?” she asked.

Matt dropped to his knees and crawled behind Julie as she slowly walked up the stairs stepping on his hands the whole way. She would twist and grind and stand on her tiptoes as she went to increase the pain. Matt’s hands were terribly sore by the time they got to the top of the stairs.

Julie led Matt into his mother’s room and she sat on the end of the very large bed. “Go to the closet and pick out a pair of heels for me to walk on you with. And you better hope I like them too or you’ll be very sorry,” she said.

Matt went into the closet and looked at his mother’s huge shoe collection. There were boots, sneakers, sandals, pumps, and heels of every shape color and fashion. Matt reached up on the shelf and pulled down a shoebox that looked new. As he started to open it Julie appeared.

“What did you find?” she asked as she grabbed the box from his hands. She opened the box to reveal a new pair of strappy black sandals with a very high heel that ended in a sharp point. “Good choice,” she said as she pointed to the heel. “This should feel great.”

Julie sat back down on the bed and crossed her legs. “Come over here and put my new sandals on me,” she said.

Matt did as he was told. Julie stood up and admired the sandals. “Your mom has great taste in heels,” she said with a devilish grin. “I’ll bet your Mom never intended for these to be used for this though, do you?” she asked with a laugh. “Lie down!” she commanded.

Matt looked at the heels. “Please Julie, not with the shoes,” he pleaded. Julie made a pouty face.

“This isn’t about you. I don’t care what you want. This is about me now. I’m in charge, remember?” she said. Matt looked at the heels again and reluctantly lay down at Julie’s feet.

Julie stood up and looked down at Matt. She lifted a sandaled foot and said, “Open your mouth.”

Matt opened and Julie slid the heel of her sandal into Matt’s mouth. “Suck,” she said. Matt started to suck as Julie slid her heel in and out of his mouth.

After several minutes of Julie switched feet and repeated the process with the other heel. She finally stopped violating his mouth and stood so that she was straddling his body. “Are you ready for some real fun?” she asked.

Julie lifted a foot and put it on Matt’s chest. She pressed down on her toes so that most of her weight was not on the heel and then stood up on Matt with both feet. Matt grunted and then said, “This isn’t so bad.”

Julie smiled evilly and said, “Really. Well, you’ll love this!” and she put her weight down on her heels. Matt screamed out and grabbed Julie’s ankles again. “Let go of my feet or I’ll stomp on you with my heel!” Julie said through clenched teeth.

Matt let go as Julie started to march in place atop Matt’s chest. With each step, she would press down on her spiked heel driving into Matt’s tender skin. Matt screamed out in pain as Julie continued her onslaught with an evil grin. Finally, Julie stood back up on her toes taking the weight off her heels. Julie spun around and stepped down onto Matt’s sore stomach. She drove her heels deep into his soft abdomen making him scream out in a high-pitched wail. She marched in place as Matt again grabbed her ankles in a desperate attempt to stop the pain.

Julie ignored Matt’s grasping hands and continued to march on his gut. Julie finally stopped marching on Matt’s gut and walked back up to his chest. “Turn your head. You don’t deserve to look at me,” she said. “I can’t believe how weak you are. You’re the one who said you could handle this.”

Matt turned his head as Julie stepped down on his temple with one foot and pressed hard. She then brought the other foot to rest on his cheek. Matt grunted and moaned beneath her as he flailed his legs wildly.

Julie sat down on the bed while keeping her feet on Matt’s head. “Take off your pants,” she said. Matt slid his pants down and tossed them to the side. “Underwear,” she said.

Matt hesitated and Julie pressed on his head. “Now,” she said. Matt pulled down his briefs and cast them to the side as well. Julie frowned. “I thought you liked my feet and legs. It doesn’t look like you like them so much right now,” she said as she looked at his flaccid penis.

“Don’t you like my feet?” she asked.

Matt answered with a shaky voice, “You hurt me.”

Julie smiled. “Oh, no. You have no idea what hurt is, yet,” she said. Then she used her spiked heel to poke and prod at Matt’s limp dick. Julie rubbed her foot all over Matt’s dick making it hard.

“That’s it. I knew I could get that little thing up again.” Julie took off her sandal and started rubbing her soft, nylon-covered arch and toes on Matt’s dick.

“How’s this feel?” she asked.

“Good,” Matt said.

“How about this?” she asked as she slammed her foot into his nuts. Matt yelled out and grabbed his sore balls.

Julie took off her other sandal and stood back up on Matt’s chest with her soft feet. “I just don’t think you’re man enough for me,” she said. “It’s no wonder your Mommy still has to have a babysitter for you.”

Matt struggled to answer with Julie standing on him. “I’m man enough.”

“Really? Well, let’s see just how tough you are,” Julie said. She started to bounce on Matt’s chest.

“Can you handle this little boy?” she asked as she bounced higher and higher. Matt started to grunt and pant with each of Julie’s heavy landings. She started to giggle as she watched him struggle to breathe under her pounding feet.

Julie began to jump higher and higher until she was completely airborne as she jumped up and down on Matt’s chest. Matt started to cough and gasp as he tried to catch his breath. Julie finally stopped jumping and stood there looking down at him.

“Tummy time,” she sang out as she stepped down onto his gut. She started to bounce again higher and higher until she was jumping repeatedly on his gut. Matt gasped and fought for breath as Julie jumped on his gut, driving her toes into his soft abdomen. “Is that your spine I feel under my feet?” she laughed out. Julie finally stopped jumping on Matt’s stomach and stepped down off his beaten body.

Matt lay limp on the floor while Julie climbed up onto the bed. She stood on the bed above Matt’s prone body.

“Are you ready?” she asked.

Matt opened his eyes just in time to see her jumping from the bed and come crashing down with both feet on his chest. Every bit of air went rushing from his body as he made a groaning sound. Julie jumped off him and laughed at his moans as she climbed back up onto the bed for a second jump. She leaped into the air again and landed full weight with both feet driving into his gut.

Matt’s body shot up to a sitting position from the force of the blow as he gasped for oxygen. Julie kicked him back down and climbed back onto the bed again. She stood at the edge of the bed and jumped high into the air. This time she landed with one foot on his chest and the other on his groin.

Matt screamed out in horror as she lifted her foot and stomped down on his nuts again before climbing off his body. Julie turned around and looked down at Matt’s racked body.

“Still think you’re a tough guy?” she asked. Matt couldn’t respond.

Julie lifted a foot and placed it on Matt’s throat and started to press. Matt grabbed her ankle as he started to gasp for air. Julie pressed harder and harder until her full weight was on his throat. She lifted the other foot and placed it across Matt’s face. She lifted her foot from his throat and put it next to the first so that she was standing on his face again. She repositioned herself so that her heels were on his mouth and her toes on his eyes like before. Julie started to bounce as Matt kicked furiously trying to get her off his face. Julie bounced for several minutes before she finally stepped down.

Julie was sitting on the couch watching TV when Mrs. Clark came home. “Hi, Julie. Was Matt a good boy?” she asked.

Julie smiled and said, “Oh, yes, Mrs. Clark. I didn’t have any trouble with him. He was just like a carpet.”

Mrs. Clark gave Julie a confused look as she handed her $20.00 for babysitting. Julie turned back around as she started out the door. “Call me anytime Mrs. Clark. I’d love to see Matt again.”


5 thoughts on “Adventures In Babysitting 20 min read

  1. This story was so perfect, wish u wrote a new one about the same topic or something simmilar but include more kissing and less jumping 😀

    1. I am glad you like it, but the story has not been written by me, but by its original author almost two decades ago. Nevertheless, there are a few other similar stories in the archives that have not been republished yet.

  2. This an awesome story that should be written as a weekly event. Excellent imagination, cudos to the author. Please write many, many endlessly more, sequels to this. Please. How old is Julie, Matt? How tall is Julie, how much does she weigh? Does she ever bring her female friends over to “help” babysit? I love it! This is my favorite story i’ve read so far. Please continue with this one. I hope Julie babysits Matt every week for years to cum.

  3. I real tramples some people do stop listening the person on the floor. The feel the body beneath them give and the person enjoys the compression. They forget it is a damageable person like themselves and go and hurt them. Stop means stop for now, back into again in a moment.

  4. This is a true story from my 14 and 15 age youth when my sitter was watching over me and my 8 year old brother who always went to bed by 8 pm She would sink her heels in me to keep me under control and in line

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