How Not To Babysit - Part 9 free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)
PART NINE: TAGGED And here I am... sitting in Vice-Principal Hennell's office, in mid- sentence, as my mother spots me through the glass separating the reception from the the school's-equivalent-to-warden's office. It's bad enough that I have had my body smacked around by a guy I considered a friend less than two hours ago, and that I have been forced into a girl's uniform by my pranking friends, but I've also been assumed to have a gender-identity concern despite my admittedly weak-ass attempts to dissuade everyone and anyone about my so-called interests in dressing or flat-out being a girl. So here's my mother, come to pick me up. And after all the panic induced effort I put towards keeping her from seeing me in diapers and a nightie just last night, I am presented to her in a skirt and blouse, with bra and panties underneath. "Fuck!" I mouth and feel one more piece of the problem on my face... I am made up. I forgot. With Jenny in tow, Mom rounds past the receptionist and her protests; and opens the the door to Mr Hennell's office. She doesn't look angry at least. "What in the world is going on?" she asks but, characteristally, doesn't wait for an answer. "Did you do this to yourself?" she asks. Fine choice of assumptions. No mom, no one did this to me. Of course, I chose everything that happened to me today. I *want* to be like this. C'mon lady! "Mom..." I start to answer but of course I get cut off. "Uh, I believe we need to speak, Mrs. Feller." Hennell motions for her to sit. "Would you leave us for a moment?" he asks me. "Please take your sister and have a seat by the receptionist." "But," I stammer but he holds his hand in the universal stop gesture. "We will speak with you in a moment," he interrupts. "Please?" he points again. I got a fucking gesture for you, you pompous ass! I turn around quickly and flip the back of my skirt up at him. Kiss that!. I stride out of the office with Jenny behind me. We each take a seat and my depression washes over me again. "You're dressed like a girl," Jenny informs me. "Yeah, thanks," I sigh. Jenny always does a good job of soothing me. Except at least one occasion that you may be familiar with... "You're pretty," she adds. I blush. Pretty? I don't want to be pretty. She's not the first to say so. I'm pretty? Really? That's messed up. Do I like it? I slump forward to rest my bra-clad chest on my knees and hang my head. "You can dress like a girl at school?" she asks as she alternates her dangling feet. "Not really," I whisper, "I got in trouble." Just a little trouble. No biggie, really! Ha! "Can I dress like a boy at school?" she asks as she stops kicking her feet. I pull myself up. She's concerned. "Sometimes the girls here wear pants," I advise her. "Is that what you mean?" "I don't want to get into trouble but I don't want to wear your clothes," she reminds me of my outfit. Thanks. "I don't want to wear these clothes either," I mope. "Mommy makes me wear girlie clothes sometimes but I hate it." She looks at me. "Is somebody making you wear girl clothes?" "Yeah," I answer. Just like you did last night... remember that? "Did you sleep in the nightie last night?" she booms. Godammit little girl, you're loud. "Shh..." I don't answer and go to hush her. "You did! You did!" she cries out. "Did you sleep in the diaper too?" Ms. Annerson suddenly stopped typing and coughed a bit. She recovered a moment later and went back to Solitaire or Facebook or whatever she does all day behind that computer. "I didn't want to," I whisper. Maybe she'll get the hint and calm down. Instead she just got louder. Dammit can little girls screech. She was really excited. "Mommy was asking about the nightie and the panties and I told her that you wore them... and a diaper," she raves oblivious to how I feel. "But Mommy said that you didn't wear it to bed. You only did it to make me feel better." She barely paused for breath. "But Mommy was wrong, you did wear it to bed. All of it!" Suddenly her voice drops and she her tone is a bit more conspiratorial, "Did you wet your diaper like I do sometimes?" I just groan. I take a second to compose myself. I will tell her no such thing happened. I open my mouth but I can see her face light up immediately. She knows! "You did! You did! I can tell," she screams out. Ms Annerson tries to stifle a guffaw. Go ahead, you cow, yuk it up. "Shh..." I slience her and she goes to rocking back and forth on her chair. I curl into a ball and try to disappear into nothingness. A moment later, the door opens and the adults spot me laying across the chairs in a fetal position. "Baby?" Mom asks. "Yes, mommy?" Jenny pipes up. "Oh, I mean Jason..." She touches my shoulder. "Are you okay?" I get into a tighter ball. This is the worst thing ever. "Come on," she says, "let's go home." Somehow I end up in the front seat of the car. I've got the stupid handbag again. Jenny's behind behind singing some childish song. I kind of remember leaving the school but it's a blur. Now, I am in the real world. I'm officially running around in girl's clothes in the real world. I'm one of the freaks that get pointed out by my friends. Those who get laughed at by everyone behind their backs. I slump down in my seat, hopefully out of sight. "Are you all right, Jason?" she asks. "No Mom," I spit out, "I'm not all right. Not at all." I choke back some tears. I grab a tissue and attack my eyes. I cough loudly and sob. We ride home in silence. Every so often, Mom looks over at me. I close my eyes and lean forward to lay my head and arms on the dashboard. After a few minutes, I hear her click the garage door opener. We coast out of the public eye and into the garage. The garage doors rattles downwards into place and I'm blissfully hidden from prying eyes again. I move quickly into the house but Mom breaks my stride with my name. "Jason," she breathes out heavily, "we have to talk about all of this. I'll see you in the kitchen." I enter the house and move towards the stairs. Just gotta get this fucking outfit off. At least I'm not locked into it. Just make it to my room. Lose the bra and panties. Slip on some respectable clothes. Then you can ground me. Then you can berate me. Then you can be disappointed in me. Then! "Jason!" she yells out. "Kitchen! Now!" It's rare that my mother commands anything that I actually stumble at the first step of the staircase. I grab the bannister to stable myself and turn to face her. "But I just wanna..." I start. "Kitchen!" she says again. "I storm off to the kitchen and take a seat on one of our breakfast stools. It's bright in here and I'm certain that all our neighbours can see me clearly if they just look. I shrink into my seat and lay my head on the counter. Mom's saying something to Jenny and the television bursts into life. Some TV show on Treehouse or whatever. Suddenly Mom's in front of me. "Jason," she says, "Mr. Hennell spoke to me about what happened today." "Yeah?" I look up at her. "What did he say?" She looks me in the face for a moment and then brushes my hair behind my ear with her hand. "You are pretty as a girl, you know?" she states. "Can I change clothes?" I ask. "Hold on," she says, "I know you were wearing your sister's nightie, rumba panties, and diapers last night." She doesn't pause. "I know is was a game to get your sister ready for bed. That's Ok." She looks at me again and sighs. "I don't know why you slept in those clothes... was it a thrill? Or do you like it?" "I don't like it," I say. "You know, I spoke with Emma about last night after you went to school." She pauses again. "Why did you soil yourself? Did you like that?" Oh, that's just fucking gross, Mom. Are you seriously thinking I *like*shitting all over myself? "No!" I bark at her. "I hated every moment of it." "Then why?" she looks at me curiously. "Why didn't you take them off." "I couldn't figure out the locks on the damn clothes!" I yell at her. All my frustration from last night comes rushing back. "I was stuck in them and I spent hours trying to get them off." It was all too much, I opened up completely. "And Emma and Dave teased the hell out of me and she undid the nightie but put it back on and she wouldn't show me how to take it off. She locked me out of the house like that! Did you know that? Did she say that? I had to sneak back in." I'm panting but the words keep falling out of my mouth, my trembling mouth. "Mr Owens saw me and..." I blubbered. I don't know how much I cough out or how much mom understands but I feel her arms around me. She lifts me lightly to my feet and escorts me away from the counter. Soon we are on the sofa. I'm in her arms and bawling like a baby. "It's Ok," she soothes. "It's Ok now." I look up at her and see she's got a weak smile. Over her shoulder, I see Jenny pop her head into the room. "Jason peed his pants last night," she sing-songs. "He should wear a diaper to bed all the time... if I hafta." Fine timing you little bitch. No diaper for me. I don't piss myself in bed. Then a memory hits me. Katie... Something stirs a bit. "Mom," I ask tentatively, "I don't want to wear diapers or girl's clothes." "You don't?" she piques. "Were you just curious?" She prattles on nervously. "You know it's OK to be curious." She hugs me tightly. "You know it's OK no matter what I'll love you so much," she sobs into my shoulder. We hold eachother. Katie... The diapers, the dress, the bra... my dick throbs in my panties. What the fuck!? Mom rests her hand on my leg and composes herself. No sooner is the hand there than she retracts it as if she was bit. My hands fly to the skirt that is rising like a tent. I pull it down and flatten it. And that's when Larry called out to the house that he was home. Shit! Larry! He's the last one I want to see like this. Tough guy Larry! Curshing cans with his forehead and bending nails with his fingers. I need to move again. "Mom! Larry! I have to hide!" I blurt out all kinds of things. I panic and push off her. She falls into the sofa as I scramble out of the room and... to where? The kitchen? The dining room? He's in the hallway now. "Daddy!" Jenny scurries to him and giggles loudly as he cries out, "Baby!" They laugh loudly together and make airplane noises. He's probably flipping her in the air as he does so often. The basement? I need him to look the other way for a moment. I need to get behind him. I need to be invisible. I need to melt into the ground. I go to the kitchen and slide open the glass door. I shut it behind me and glue myself to the house. Shuffling along the bricks, I work my way to the side door. If I can get there and back into the house, Larry might not see me. Then it's a sprint to my room and a quick change of clothes. I can do this. The fence rises up in front of me again. My old diaper is here on the ground. The sun has not been kind to its aroma. Goddamn! It stinks. I kick at it. It hobbles over to the corner where the fence meets the house. I'll have to get it later. I leave it as I examine the fence and the gate. It's only latched. It pops easily and the gate glides smoothly open. Soon I'm at the door. I peek into the glass and see no one in the laundry room. I try the door but it won't budge. It's locked! Owens, you dirty bastard. You took the key last night and locked me out! Fucketty Fuck! I sit heavily on the concrete block that serves as a step. "Hey!" I hear from somewhere. It's Mr. Owens. I shrink. No, you fucker. Not now. No one can see me... especially not you! "Katie!" he yells loudly and closes in. He's on the other side of the fence when he speaks again. Something is poking through the wooden slats of the fence. It glints in the sun. "Get over here girl!" he hollers. "You want this?" he slides the key up and down between the slats. I move to the fence. Luckily he can't really see me here. I grab the key between thumb and forefinger but I can't pull it out of his grasp. "Hold up," he says. "I have a secret and you have a secret. I think we should keep both secrets to ourselves." "You're a pervert!" I scold him. "You're a pedophile and you were going to molest me." "Not at all," he says quietly. "I'd not touch you at all. Not there. I just wanted some fun." "Sick bastard!" I cough at him. "It *was* fun for you, wasn't it?" he says. "Exciting?" "Fuck off!" I say through gritted teeth. "And give me the key." "Strong language for a proper young lady such as yourself," he mocks me. "How'd you come about dressed as such?" "Give me the key!" I demanded. "First a deal," he offers. "I keep your secret, Katie-Baby." He rolls the words off his tongue. "And you keep mine." "Fine!" I growl. "Just stay the hell away from me and my family." "No, no, no, that won't suffice," he chuckles. "I want to play again some time." "No way." I'm just gonna tell every one that you're a sick pedophile creep and let the cops deal with you. "See, now that won't please me either," he says. He pushes a piece of paper through the sam slat, just below the key. It falls to the ground but I can make out what it is. It's me. In diapers. In the driveway. Watching my sister leave with Dave. Sucking on a binky. The picture is surprisingly clear for a night shot. "You can even tell the diaper is already soiled," he points out. "Blackmail!" I yell. "You're blackmailing me?" "I'll give you the key. You'll keep my secret. I'll keep yours, and you *will* come by to play again tomorrow." He pauses to let the words sink in. He lets the key fall between the slats. It lands on the photo. I squat down and collect both. I fold the photo and go to put it in my pocket. Pocket? What pocket? My hands run all over my skirt and vest looking for a pocket. I trace the cups and underwire of the bra under my clothes. I cup the missing breasts in my palms. I run my hands down my sides, feeling the vest, the bra straps and the blouse. My penis jumps in my panties. I run my hands down to my hem and caress it with my fingertips. My hands run the length og the skirt and tickle my exposed thighs. I'm so fucking turned on now. Outside! In drag! Make-up! Oh my god, the make-up too. My penis pushes forcefully against the panties. Ok, snap out of it. You shouldn't enjoy this. This is wrong! You have to get into the house and out of these clothes. I moved quickly to the side door. In my eagerness, I slip on the concrete block again and slam into the door. Via the window in the door, I peer into the room. It's clear. I slam the key home and turn the lock. The door opens and I step into the laundry room. In one smooth turn, I catch the door, close it quietly and return to face the hallway that leads to the stairs, and ultimately, my bedroom and boy's clothes. I dart for it. "Who's there?" Larry calls out from the kitchen. "It's me Larry!" Be down in a sec. Hopefully he just thinks I got home from school. I rush the stairs and almost slide into my room. I tear off the vest and blouse. I undo the skirt and let it fall. I kick off the shoes and pull down the socks. The bra! I reach around to get the clasp. It's hard to get to. I can't reach it. The room spins as I turn and turn trying to will my fingers to touch the bra clasp. I sit on my bed and reach over my shoulders to get to the clasp. It's not within my grasp. How did I get this thing on in the first place? Fuck! I pull off the panties and toss them into the growing pile of girl's clothes. Now I'm naked except a black push-up bra. I quickly grab a t-shirt, some boxers, and a pair of shorts from my fresh laundry. I look at myself. The bra is clearly visible through the white tee. Dammit! I paw off the t-shirt and get back to work on the bra straps. I pull them off my shoulders and slide my arms through. Now the bra is simply around my chest like a band. I pull it down and step out of it. Yes! My chest has red marks where the bra sat for the last few hours. Shirt! Shirt NOW! And no swimming tonight! Finallyl I'm wearing the tee and I look like a guy again. I push open the door and head downstairs. All is ok. If I can get Jenny to shut up I'll be ok. If I can get Emma and Dave to shut up, I'll be ok. I think mom believes me and she will shut up, I'll be ok. I get to the kitchen and head to the fridge. "Hi Larry," I call out as I grab a Dr. Pepper. "Hey Jason," he says without looking up. He's coloring with Jenny. Jenny looks up at me and giggles a bit. Larry laughs with her for a sec before he follows her stare. His face gets very serious very quickly. "Karen!" he yells to the dining room. "Why is your son wearing make-up?" END OF PART NINE

Same as How Not to Babysit - part 9 Videos

4 years ago
  • 0
  • 19
  • 0

Wendy52 asked to babysit 2

I had just put the phone down to my husband and was now covered in cum, it was all over my breasts and face, plus there was a large amount running out of my pussy.These two young studs had given me a much needed good fucking, and it was only day one of our 5 day weekend.I reached my hands down to their now rock hard shiny black cocks and said we better go and clean up. They just said the pool is right here.I said no we need a shower, so I grabbed their cocks and pulled them into the house....

2 years ago
  • 0
  • 21
  • 0

How Not To Babysit part 22

PART TWENTY-TWO: From the hall I hear Jenny talking excitedly to Stewart. "Katie wears a diaper all the time!" she tells him. "And Katie needs to sleep in a diaper 'cause she might wet the bed. That's the rule." "That true?" Stewart asks skeptically. "Are you getting the diaper on?" he asks through the door. "Yeah!" Jenny pipes up. "You promised to be the baby!" The pink tank-top and green skirt crash my fantasy. This isn't fun anymore. I was excited by the diaper for some...

1 year ago
  • 0
  • 48
  • 0

Babysitting Adventures

CHAPTER 1 I loved babysitting. Not so much with actual babies, but for kids that you can joke with, tease, play games with, or just have fun with. I was so good with kids that my parents’ friends were always asking for me to sit for them. My parents were very strict and would not allow me to date or even hang out with boys my age. But, babysitting was acceptable. It was both social interaction and my only way to make money. I loved to hang out and babysit for family friends. They...

3 years ago
  • 0
  • 48
  • 0

Laura aka The Little Nympho Chapter 11 Babysitting Katie Resubmitted and cut into 3 parts

Introduction: This is such a long chapter that I have cut it into 3 Parts. And I do apologize for the length.. However it is a critical part of this story and is necessary to maintain the stories continuity.. In this episode, Laura begins her new job babysitting for the Bells.. She meets Mr.Bs beautiful wife Lana and their very precocious daughter Katie.. She then makes a few mildly disturbing discoveries about her new employers.. And when her job gets unexpectedly extended for another day, it...

2 years ago
  • 0
  • 18
  • 0

How Not To Babysit part 13

PART THIRTEEN: REINTRODUCED In a moment, the bad is over-turned and the card falls out. I flick at it with my fingertips until it's open and I can see Mom's neat script. "Baby," it reads. Dammit woman! Stop calling me that. I don't want to be a baby. I don't want to be a girl. I find my hand fondling the lace of the nightie. I drop it again. "I know you wore your sister's nightie last night. I can understand why it appealed to you because they are so soft and pretty. I want you...

1 year ago
  • 0
  • 23
  • 0

Charity At Work 1 Adventures in Babysitting

Charity Jones here again returning to entertain you with more adventures of my misspent youth. My lat recounting detailed certain highpoints in my life as it transpired through the11th grade in my 16th year of life. I introduced you to the complete trinity of my closest friends, Faith and Hope. I also landed myself a highschool sweetheart by the name of Chet, who in turned out to be my personal cuckold. And of course the trials and tribulations of jut being a high school teen. The...

1 year ago
  • 0
  • 22
  • 0

Gina Loses Her Virginity While Babysitting

I've been babysitting for the longest time. Every weekend, I have a job and have made enough money to buy a car. I've been babysitting for the Jackson's for about two years now. They hired me overnight and will be paying me three hundred dollars. I'm so excited to go over there tonight. The best part of babysitting over there, is their gorgeous son named Jack. I wasn't sure if he'd be home, but I was hoping he might be. I've had a crush on him for the longest time. He's so incredibly...

1 year ago
  • 0
  • 25
  • 0

My Sister And I Babysitting

My Sister And I Babysitting My sister and I have always been close. I had been looking for a way to earn some extra money when my sister suggested that I help her baby-sit. She promised that I would not have to change any diapers as long as I helped out by getting bottles ready and playing with the children. She had tried babysitting once and it was more than she could handle. Mom had suggested that she find a girlfriend to help but none of her friends wanted to spend their Friday and...

2 years ago
  • 0
  • 21
  • 0

Adventures in Babysitting 2

Adventures in Babysitting, 2 I lay in bed fantasizing about Laura's daddy. now that I'd gotten some real experience I felt I had a better chance at seducing him. I finally fell asleep and woke up cranky the next morning as I started to get ready for school. "T, Tammy are you alright?" asked Momma over breakfast. She pressed the backs of her fingers to my forehead. "Well no fever, so you still have to go to school," she announced. It was nice being able to leave the house as...

3 years ago
  • 0
  • 55
  • 0

Babysitting with unique benefits part 1

A few year ago, (I was not yet able to drive, to give you an age), I had been babysitting around my neighborhood to make some extra cash. It's not something that most guys do, but it's a service that most parents need and it seemed like an easy way to earn money and not many of my peers want to work at all.I had been babysitting for two couples on a fairly steady basis when I got a call from a third couple. They wanted me only on Sunday nights and that worked perfectly. I added then to my...

4 years ago
  • 0
  • 28
  • 0

Babysitting

My parents were helping me with my first year college tuition and board but made it clear that I was on my own as far as paying for fun. There was no money for a car so I made do as best I could. Without a car, I was very limited as far as part time employment was concerned so I fell back on the familiar job of babysitting. My parents did help me get a credit card with a low limit but I had to make the payments myself. I enjoyed the use of the card a little too much and soon had the limit...

2 years ago
  • 0
  • 17
  • 0

When i used to babysit

The houses were all quiet, bathed in the moonlight. I shut the curtain and paced back across the living room. It was already past two o'clock. I was bored, there was nothing on televisions, all the stations had signed off over an hour ago. My eyes were to tired to continue reading. This was going to be a longer night than I had bargained for. I laid back down on the sofa, just to rest for a little bit.I knew I would be out late when I agreed to baby-sit for Holly. She had recently divorced her...

3 years ago
  • 0
  • 18
  • 0

How Not To Babysit part 16

PART SIXTEEN: PUNISHED "What are you doing?!" Emma demands. I'm prancing around the house in your clothes. What does it look like? This is terrible. "I, uh," I stammer. "I just took that dress off five minutes ago and you're already wearing it!" she scolds. "Take it off!" she demands. "Take it off, right now!" she repeats. "Babe..." Dave calls from the doorway. "You okay?" he says but his words hang there. Dave smiles broadly. "You don't want to wear girl's clothes,...

2 years ago
  • 0
  • 20
  • 0

How Not To Babysit part 20

PART TWENTY: RESCUED Before I get home, Dev sidles up next to me on his bicycle. He easily keeps time with my rapid stride. Jenny, unfortunately, cannot and is half-dragged, half-carried. "Hey sexy," he smiles at me. "Go away!" I tell him. "You asshole!" He smiles at me and maintains speed. Two more guys join him, Will and Stewart. "Go away!" I repeat. "All of you!" "But you look so hot in that outfit," Dev says. "Katie." I stop abruptly. We're no longer on First. There...

2 years ago
  • 0
  • 18
  • 0

How Not To Babysit part 15

PART FIFTEEN: FOXHOLED Dave? Now? How am I supposed to hide from him this time? It's bad enough that he caught me last time. Once can be a game gone wrong. A trap. But twice? Twice is a pattern. Twice is a choice to wear girl clothes. Twice means I'm a tranny. Fuck me! Go away Dave. "Come in Dave!" she calls to him. "We're in the laundry room." "Why are you calling him over?" I panic. My instincts kick in. I want to run. If I go into the hall, Dave will be waiting for me. I turn...

3 years ago
  • 0
  • 26
  • 0

Babysitting Steven Part 1

Introduction: Babysitting Steven This story starts off slow to reflect character as well as to set the scene. As most weekend I was asked to babysit for my neighbors, they lived not so far down the street and was extremely nice, they seamed to prefer me to babysit instead of any of the other teenagers in the neighborhood. I was always paid a little extra as they think there only son is a brat. I know different. A bit later than usual my mum came into my room and told me that I was...

2 years ago
  • 0
  • 22
  • 0

Jens first babysitting job

Introduction: First story ever hope you enjoy plot: Jen was going to spend the whole week watching porn but now she is stuck babysitting-horny boys Jens first babysitting job part 1 Jen was surprised when she answered her cell and was offered a baby sitting job from the martins,her neighbours across the street asking her if she would baby sit there two sons Brady and Braden she seemed very desperate so Jen said yes she moaned she was really looking forward to spend a night looking at porn and...

4 years ago
  • 0
  • 15
  • 0

How Not to Babysit part 6

PART SIX: GARBED What is this supposed to mean? I stare at the laundry basket and the piece of clothing I was stuck in for several hours yesterday. That stupid, bright-ass pink, ruffled, girly-girl set of plastic panties. I hate them. A minute went by, and I finally pull the basket in to my room and push it out of the way. I have to move, the bus was coming. I run down the stairs and into the kitchen. Jenny is here, playing with her food, as usual. Mom hands me my lunch, a...

3 years ago
  • 0
  • 18
  • 0

How Not to Babysit part 5

PART FIVE: ACQUIRED It took a moment but I finally came back to my senses. Was it shock? I don't know. I just stood in the driveway like this for god knows how much time while sucking on that binky. I spat out the binky, ran to the garage and tried to lift the huge double-door. It wouldn't budge. Of course it wouldn't budge... that would have saved me. I slipped alongside the house to the backyard gate. It was usually locked from the inside. We only ever used this gate to let...

2 years ago
  • 0
  • 19
  • 0

How Not To Babysit part 25

PART 25: CONVICTED I remember Owens saying something about not much in the bag being of interest to Jenny. She ogles the opening Mr Owens duffle bag anyhow. "For you, miss?" Owens studies her face. "Mister..." she corrects him distractedly. Somehow she's still in character. "That's right!" he agrees. "Miss... ter..." he draws out. "Mister Johnson!" Her focus returns to his eyes. I'm still looking into the bag. He's got a cloth diaper in there for me. For pathetic me. For...

4 years ago
  • 0
  • 20
  • 0

How Not To Babysit part 18

PART EIGHTEEN: PADDED "Baby Katie! Baby Katie!" naked Jenny is running around the room chanting. "Jenny, go get dressed," Emma orders. Jenny hurdles up the stairs. Her chanting goes on. I hear her singing those two words as she digs through her closet. "Emma..." I speak without knowing exactly what I want to say. I want this diaper off. I don't want to go around in a wet diaper. Do I? I want if off but do I want a fresh one on me? I wore a fresh one last night. It was......

4 years ago
  • 0
  • 17
  • 0

Adventures in Babysitting

Adventures in Babysitting By: Malissa and Gang Tommy Moore, was a bit of a loner all his life, no close friends other than the girls he went to school with. But he never dated any of them. Now as a senior in High School he was on the honor roll list. His mother was a bit concerned though, he seemed to not have any life outside of school. Of course she had her hopes, as he would often go to Laura's house for the girls study group, three or four girls he went to school with who needed...

4 years ago
  • 0
  • 18
  • 0

How Not To Babysit part 19

PART NINETEEN: SWITCHED "We have to go swimming now!" Jenny announces. I've been day-dreaming about the times I've left the house in drag. She's been watching TV but I've been trying to figure out some explanation for all my friends. I walked around school in drag on Friday. I was caught wearing a satiny girl's nightie under my clothes. I let Lisa make-up my face. I paraded around the school like some sissy and Jared beat the hell out of me. They all saw me willing go to class in...

4 years ago
  • 0
  • 19
  • 0

How Not to Babysit part 8

PART EIGHT: DETAINED I almost immediately run into Mr. Hennell, the Vice-Prinicipal and head bastard in charge of detentions. I've crossed his path a few times before but suddenly, I have no idea what I'm going to tell him. The plan is that I'm pranking him. This is a joke. He gets upset an the rumour goes around the school that I dressed up like a girl to piss him off. I think about it. What kind of dumb plan is this? Oh well, I'm in. I should play it up. Flash him my underwear and...

4 years ago
  • 0
  • 19
  • 0

How Not To Babysit part 14

PART FOURTEEN: LED "That's not mine!" I blurt out. "Of course, it's not yours, it's mine!" she says. "Why is *my* uniform in *your* closet?" she repeats. "It's not yours, either," I say. Please just go away. I'm tired of talking about how I've been wearing girl's clothes. I don't have the will to lie to you. Just leave. "Not mine?" she ponders. "Can you explain why you have any girl's uniform in your closet?" "Oh god, please?" I beg her. She steps to my closet. I stand...

3 years ago
  • 0
  • 16
  • 0

How Not To Babysit part 10

PART TEN: TESTED "Make-up?" I mutter. Oh shit! I forgot to take off the make-up! I leave the can of Dr. Pepper on the counter and dash out of the kitchen. I clear the hall and stumble into the powder room. I check the counter top for anything that takes off make-up. Mom or Emma should have some of that shit around here someplace. I'm still searching when there's a knock at the door. "Come out, Jason," Mom says. "I'll help." I open the door to see both Mom and Larry clogging the...

4 years ago
  • 0
  • 19
  • 0

How Not To Babysit part 23

PART TWENTY-THREE: BABY-SAT My body slowly becomes my own. Sweat pours down my back. I lean over and peer down the hallway to watch Owens pay for my pizza dinner as Stewart holds the pizza. Kevin the pizza guy winks at me and turns to leave with a wave to the group. Ass! Owens steps into the house! Oh no! Get out! I can't speak. He looks right at me and smiles. "Are we playing dress-up tonight?" he asks loudly. I know he's really asking me but Jenny answers. "Yes!" she...

2 years ago
  • 0
  • 18
  • 0

How Not to Babysit part 3

PART THREE: CAPTURED I tossed aside my bedsheets and jumped to my feet. The diaper sloshed and I cursed quietly. Fucking diaper! What the hell is wrong with me to have put this on in the first place? I waited in the dark a little longer. I so much wanted this diaper off but I didn't want to ruin my chance by waking anyone who wasn't quite asleep yet. Opening my door, I checked my Mom's room. The door was open and the lights were out. Larry was snoring softly. I padded into the...

2 years ago
  • 0
  • 22
  • 0

Babysitting leads me to a new friend

The fourth time I was asked to sit I agreed and knew I would be watching the DVD’s again. As I had done before I waited for a while to make sure the kids were asleep I went and got the DVD’s. I went to the cabinet and there were two more there and like the others were just marked with a date. I looked at the date and one was the date of my last babysit job and another the week earlier. When I put the first one on it was a home made one that had the people I was babysitting for and two...

2 years ago
  • 0
  • 25
  • 0

Amy the Babysitting Slut Dream Job Lost

Introduction: First Story in a Long Series Adapted from Cyber Chat This story is fictional. It started out as a cyber chat play that just grew, producing long stories and a long series, six in total so far. Most writing is mine but the thoughts, the direction and even what is happening sexually comes with approval. We told of our fantasy, me wanting a babysitting cheerleader, her wanting to have forceful sex and be paid. What came is this series about Amy. I know the themes in here are not...

4 years ago
  • 0
  • 21
  • 0

How Not to Babysit part 2

PART TWO: CAGED "Jason? Hello? You in there?" It was Mom. "Mom! Don't come in! I'm..." I stumbled to the door and let my weight fall on it. I paused. "... not decent." "Just wanted to let you know that we're home and I checked on Jenny. She's asleep. Everything went well tonight?" she said through the door as she stopped pushing. I laid against the door and sat on the floor, hearing my diaper crumple and my ruffles crinkle. They were the loudest noises ever, I was certain Mom...

3 years ago
  • 0
  • 20
  • 0

How Not To Babysit part 17

PART SEVENTEEN: PADDED The front door is just closing as I present myself to Mom and Larry. It looks like they had a great time. Larry makes eye-contact. "Hi Jason," he says tersely. "Hi Larry," I respond. "How was the evening?" "The movie was better than I thought," Mom bursts in. "I was expecting mindless violence but they actually had a plot." She licks her lips. "The lava cake for dinner was so decadent!" "That's great!" I stay upbeat. "I wanna see that one too." I keep...

Humor
3 years ago
  • 0
  • 19
  • 0

How Not To Babysit part 21

PART TWENTY-ONE: PLAYED "No Jenny," I say to her, but my eyes are on Stewart. I don't like guys. I'm pretty sure of that. I *love* the way he's looking at me. I don't get that. "You promised to play house!" Jenny complains. Stewart raises an eyebrow. "In a bit," I placate her. "And you promised to be the baby girl!" she reminds me. Stewart's eyebrow moves towards the ceiling. "Baby?" he asks. "Yeah," Jenny answers as she joins us. I'm dumbfounded. "Katie wears...

3 years ago
  • 0
  • 23
  • 0

How Not to Babysit part 7

PART SEVEN: PARADED "No, guys," I plead some more. "Stop." Will opens the shoulderbag and digs around. He finds a pair of white cotton panties with pink trim. He tosses them to me. "Cover up your junk," he says. "I don't want to wear girl's clothes," I protest. "News for you: you are wearing girl's clothes and you're almost naked," he points out. "And you aren't getting anything else to wear from us." "This is weird," Lisa pipes up. "Yeah," Emily adds, "we're going to...

3 years ago
  • 0
  • 18
  • 0

How Not to Babysit part 4

PART FOUR: DISPLAYED "No way!" I said, "I'm not leaving the house in this." "Dave, quit messing around. This is embarrassing and he really reeks," Emma tred to reason. "C'mon Em, we're just gonna go to Stacey's for an hour and then we'll come back. It'll be just the five of us and him," Dave persisted. "He deserves to be made fun of... look at him!" "It's not my fault!" I must have whined. "I can't get them off," I repeated. "I put them on to calm Jenny down and get her to bed...

2 years ago
  • 0
  • 16
  • 0

How Not To Babysit part 12

PART TWELVE: PRESENTED "Jason, eh?" the delivery guy snickers. My legs falter and I need to grab the banister. Oh fuck me! Jenny! You little brat. Why do you just blurt out everything? I walk to the entrance and take the pizza from him. I turn to put it on the chair in the foyer. I feel his eyes on me. Checking out my legs and watching my skirt flit around. "So, are you one of those transsexuals?" he asks me. "What!?" I blurt. "No! Never! God! Just go!" I turn to face him....

4 years ago
  • 0
  • 35
  • 0

Babysitting pays Part three

"Ya'll didn't even wake me up? Bah!" My cock had grown erect with this in sight and was ready for something to happen. "Oh I'm sorry Mike! I told Brooke she should!" Brittany said, glaring at Brooke, "I'll make it up to you, somehow, what can I do?" Smiling, I told them all to follow me out to the living room. "Brittany go lay down on your back there while I put my hard prick into your pussy" Just the though of that made Brittany nearly gasp and drip with sticky wetness....

2 years ago
  • 0
  • 26
  • 0

Adventures in Babysitting

When I was 14, me and my BFF, Ashley, started our very own babysitting service. She made an announcement during church and we immediately started getting phone calls. One day, Ashley said, "Come here...U gotta check this out." And she pulled out a handful of 20's. "Damn, where'd you get that?" I asked. "Babysitting," she said with a smile. I counted it...just a little over $200. "How'd you get $200 babysitting," I asked. Now, Ashley was the neighborhood nymphette and I was the...

2 years ago
  • 0
  • 16
  • 0

How Not To Babysit part 24

PART 24: BERIBBONED I'm not sure what's going on at this point. I hate Mr. Owens. I'm afraid of him. He's not allowed here. There's no way Mom and Larry *asked* him to come by. So he paid for the pizza - that doesn't entitle him to use us to play his perverted game. I could leave. L could call the police. I could change and tell him to go. I *can* take control. Stewart can take control. Why are doing exactly what Mr. Owens says. I want this diaper off. I want these embarrassing...

4 years ago
  • 0
  • 30
  • 0

Tinas Babysitting Adventure

Tina, glaring at her mother, stamped her foot on the checkered linoleum floor in the kitchen. "Ya gotta be kidding!" "Honey, just this one time." "I'm too old to babysit. Jeez, Mom, I'm nineteen." "You're almost-- That doesn't matter. What matters is your kid sister promised and the Webbs have plans. It's too late to get anyone else. It's not Sammi's fault she got sick. Do it for her." "But, Mom, babysitting? What if my friends find out?" "So what would be the big deal?...

4 years ago
  • 0
  • 44
  • 0

Wendy52 asked to babysit 6

I just handed my phone to Rosemary and watched in shock as she called the whole of the local mothers cooking club.As each one answered she told them to hold whilst she added others to the call. Soon she had Julie, Alison, Claire, Margaret and Lisa on the phone, she switched it to speakerphone then told them all she was with Wendy who was babysitting for Charles. The girls all giggled and past rude comments about how they bet I had my hands full over there and probably much more if I played my...

3 years ago
  • 0
  • 25
  • 0

Wendy52 asked to babysit 4

By the time my mind had cleared and my body had stopped rolling from orgasm to orgasm the boys had led me back out to the car. My pussy was leaking cum all down my legs, and my face and tits were covered in hot sticky cum. They allowed me to sit in the car and recover as they loaded the groceries into the boot of the car.On the journey home, they allowed me to concentrate on my driving and didn't touch my body or play with me once. I was allowed to go into the house while they unloaded the car....

4 years ago
  • 0
  • 27
  • 0

Amy the Babysitting Slut Job Offer

I know the themes in here are not going to be for everyone, taboo and morally wrong. I am not saying that they are mine or hers but this is what came from our chats. I was highly encouraged to edit our talks together and post them in story form here on XNXX. Each story will have set up but you can scroll to the good parts quite easily. But since these chats were not meant to be stories, there will be gaps, especially in the beginning where transitions should occur. All people involved are...

4 years ago
  • 0
  • 29
  • 0

Amy the Babysitting Slut 1 Job Offer

I know the themes in this story are not going to be for everyone, taboo, and morally wrong. I am not saying that they are mine or hers but this is what came from our chats. I was highly encouraged to edit our talks together and post them in story form here on XNXX. Each story will have set up but you can scroll to the good parts quite easily. But since these chats were not meant to be stories, there will be gaps, especially in the beginning where transitions should occur. All people involved...

2 years ago
  • 0
  • 24
  • 0

Amy the Babysitting Slut Chapter 01 Job Offer

I know the themes in this story are not going to be for everyone, taboo, and morally wrong. I am not saying that they are mine or hers but this is what came from our chats. I was highly encouraged to edit our talks together and post them in story form here on XNXX. Each story will have set up but you can scroll to the good parts quite easily. But since these chats were not meant to be stories, there will be gaps, especially in the beginning where transitions should occur. All people involved...

1 year ago
  • 0
  • 21
  • 0

Maddie the Babysitting Slut Chapter 1 Dream Job Lost

I know the themes in this story are not going to be for everyone, taboo, and morally wrong. I am not saying that they are mine or hers but this is what came from our chats. I was highly encouraged to edit our talks together and post them in story form here on XNXX. Each story will have set up but you can scroll to the good parts quite easily. But since these chats were not meant to be stories, there will be gaps, especially in the beginning where transitions should occur. All people involved...

3 years ago
  • 0
  • 21
  • 0

Hypnotizing the Babysitter Ch 01

This is a chronicle of the most important two weeks of my life. First things first, though. I should warn you about this story. For, while the title is certainly accurate… and while this tale really IS about me hypnotizing the babysitter… and while it really IS about how this girl’s head was filled with all sorts of enticing and passionate suggestions… and while it IS about how these suggestions led her to engage in extremely arousing and exotic sexual relations with me… I feel obligated to...

2 years ago
  • 0
  • 43
  • 0

Babysitting the Twins Again Part 3 Jennys Halloween Sleepover

This is part 3 of the Story of Debbie, Jenny, and the twins. This story introduces Jenny's friends. Please read "Babysitting the Twins Again" and "Babysitting the Twins Again - Part 2 - Sweet Sixteen" for the precursory stories. Cast of Characters: Billy and Bobby -- 15 year old identical twins. Smart, handsome, tall, athletic, horny. Willing to break a few rules… well actually, all the rules. Debbie - 22 year old "star" of part 1, Tall norse goddess... Had a little trouble...

2 years ago
  • 0
  • 35
  • 0

Babysitting Lucy

It was Bradley's very first job - babysitting Mrs. Braun's seven-year-old daughter, Lucy. Mrs. Braun had told Bradley's mom that she would need a babysitter on Saturday's for the rest of the summer as she took a teaching certificate class. I was going to be pretty easy money for the thirteen-year-old Bradley, taking care of a seven-year-old during the day and on a weekend too. He figured they could play most of the time. What a great way to make money, and Mrs. Braun was going to pay him...

3 years ago
  • 0
  • 42
  • 0

Babysitter Gets Fucked by the Boy Shes Babysitting

“You know…” She began. “We still have some time left…” Rachel purred. Jake chuckled. Rachel moved her right hand down to his crotch and held it there. Rachel felt the boy’s face twist into a grin. Rachel grinned as well and began grasping at the kid’s growing erection. Jake’s cock slowly grew, thickening and lengthening. It pointed upwards and reached passed the kid’s belly button under his shirt and pants. Rachel grabbed the meat through the fabric and started lightly stroking it causing Jake...

4 years ago
  • 0
  • 35
  • 0

Babysitting the Twins Again

I’ve known the twins, William and Robert, for a long time. Of course, everyone calls them Billy and Bobby. They call me Debbie. When I was 14 and they were 7, I first started to babysit for them. I’d bring over some games and crafts, and we’d have the most fun. When they started with cub scouts, I’d help them with their scouting activities. As they got a little older, I’d help them with their homework. I would also wrestle the two of them at the same time, but they were never a match...

2 years ago
  • 0
  • 20
  • 0

Babysitting for Mr Johnston

I'm Lorraine. I'm 19 and I have brown hair and eyes. And good B-cup boobs. I'm saving up to go to college, so I babysit when I can. So a lot of weekends I'm at someone's house not partying. It was Saturday night and I was looking after Mr. Johnston's baby. He had a baby girl named Jennifer, 4 months old and she was beautiful. So I found myself over there just watching some TV as he was gone and Jennifer just slept mostly. “Shit, there is like not one damn thing on TV,” I said. I looked all...

Straight Sex
2 years ago
  • 0
  • 22
  • 0

Abby Jeff Babysitting Abby and Charlotte

The Chronicles of Abby: Jeff Babysitting Abby and Charlotte(Abby’s Perspective)Synopsis: This part of the story is a sequel to the episode “Abby’s Birthday Part 2”. Abby’s dad needed to work on a project and he won’t be around to care for Abby. So, he placed Abby under his neighbor’s teenage son, Jeff’s care. Jeff got to babysit his little step sister, Charlotte and his neighbor little Abby.[SEXY COMMENTS APPRECIATED!!!] Jim had just fetched Jeff and Charlotte home from school. Before heading...

2 years ago
  • 0
  • 62
  • 0

The Knight and the Acolyte Book 8 Chapter 8 Impaled by the Minotaur

Book Eight: Labyrinth of Love Chapter Eight: Impaled by the Minotaur By mypenname3000 Copyright 2016 Note: Thanks to B0b for beta reading this. Acolyte Sophia – The Labyrinth, the Island of Yalut The words of the Minotaur echoed down the hallway out of the darkness of the large room before us. The source of the foul stench pervading the Labyrinth flowed with it. In the glow of my pink, ethereal light bobbing beside me, I spotted a skeletal arm stretched out of the large room,...

1 year ago
  • 0
  • 20
  • 0

Mysterious Hypnotic Spiral Hypnotizes Mom

Susanne Butler was settling in for the night in her house, she was Caucasian, she was 62-years-old, she was 5'8, shoulder length long blonde hair, blue eyes, she was wearing underwear, a long satin silk nightgown, she was also a loving divorcee mother to her 18-year-old teenage Daughter named Katherine, she's also Caucasian, she's 5'7, brunette hair, hazel eyes, her 16-year-old son named Peter, he was also Caucasian, he was 5'9, brown hair, brown eyes, her 3-year-old Toddler son named Mark, and...

Mind Control
2 years ago
  • 0
  • 35
  • 0

The Knight and the Acolyte Book 8 Labyrinth of LoveChapter 8 Impaled by the Minotaur

Note: Thanks to b0b for beta reading this! Acolyte Sophia – The Labyrinth, the Island of Yalut The words of the Minotaur echoed down the hallway out of the darkness of the large room before us. The source of the foul stench pervading the Labyrinth flowed with it. In the glow of my pink, ethereal light bobbing beside me, I spotted a skeletal arm stretched out of the large room, fingers twisted in agony, one of the beast’s victims. My heart hammered fast. We were at the heart of the...

4 years ago
  • 0
  • 22
  • 0

Babysitting Fun

Introduction: Julie missed the party to babysit, but didnt miss the fun… Graduation was just around the corner. I couldnt wait. Id spent the last two years planning on where I was going to college and couldnt wait to get away from under my parents thumb. It was Friday and I was planning on meeting up with some friends at a party. It was a come in uniform party and I was just putting on my little catholic school girl uniform when my mother came into my room. I forgot to tell you. I told Mrs....

4 years ago
  • 0
  • 37
  • 0

Howie Returns to PennsylvaniaChapter 3

Howie was up at dawn. He ran and worked out. Then he drew in his garage studio for an hour. At ten he was at the FIJI house helping the other pledges as they cleaned the house. "Chief, what have you got that Dorothy sees in you?" a pledge asks. "A dynamic personality, I guess," he said. One pledge said, "I hear that Dave is pissed." Another pledge asked, "What is the Dunger pissed about now?" Another one said, "Cause he is getting any, not less any that looks like her." They...

Porn Trends