Babysitter Spanking Story
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Babysitter Spanking Story
Stories from days past, you can find masterposts for series here about older stories, you can also post your favorite older stories here as well, be sure to credit the author.
More Stories wrote:
Jacked Off by the Babysitter by More Stories
When I was a teen my little brother and I had a babysitter watch after us when my parents went out. I personally felt like I was too old to have a babysitter, but since I was known for being a troublemaker, and I was stuck with a younger brother (11) too I was condemned to being babysat even at my age. Fortunately, we had a hot looking babysitter named Nancy, who was 18 with big firm boobies, green eyes and beautiful auburn hair. In front of my parents she always acted all calm and proper, but when my parents weren’t home she was a very different person. She would let us do a lot of things that my parents would never approve of like stay up and watching grown up programs on cable that had bad words and nudity, eat junk food, and even teach us dirty words. She knew I was a horny little devil and liked to tease me in different ways.
One night when babysitting us we were playing cops and robbers with my little brother to entertain him. We would take turns, one person being the policeman, and the other being the robber wearing a ski mask. We used the whole house, and with the lights off the robber would have to sneak into rooms and steal stuff putting it in a pillowcase without being caught. The police person would go through the house one room at a time looking for the robber. If you didn’t listen, and hide really good the policeman could find you and arrest you. We had these cheap handcuffs that were actually made from metal, but had a little hidden safety latch on them. Funny thing is it was really hard to reach the release latch if you were the one handcuffed.
One of the times when I was playing the policeman, and she was the robber, I caught her in the den hiding behind the couch. I got to arrest her and “play” search her for anything hidden on her or in her pockets. She let me reach under her shirt and feel her breast through her bra, and reach into her jeans pockets. I even tried to unbutton her pants and got as far as unbuttoning and unzipping them before she stopped me saying that was far enough. Seeing the top of her little white panties with a red elastic waistband and little colored dots on them made me really horny. Her smooth skin and flat tummy drove me wild. I wanted to do more but she would not let me.
We had been playing for a while so around 9:30 she told my brother it was bedtime. He didn’t want to go to bed and was being a brat about it. She ordered him to get into his pajamas, but said I could stay up longer. She put my brother to bed, and I went to change. She was sitting on the couch watching TV when I came out a while later in my lose-fitting pj’s with stripes on them. As soon as she saw me she started laughing poking fun at my pajamas. Feeling belittled I threw a fit and jumped on her trying to overpower her. I was trying to pin her down to the couch but she was stronger. In all the struggling and wriggling around together I got excited. I wasn’t wearing any underwear and with all the close contact I got a raging hard-on in my pants. Then she rolled me over on my stomach and managed to handcuff my arms behind my back! With my hands behind me I could not reach the little release catch. I was stuck handcuffed with a hard-on grinding against the ground now! I mean it got rock hard. She said she was going to spank me like a little baby if I kept misbehaving. I didn’t care. Then things got even worse (or better depending on how you look at it). When she rolled me over again to talk to me the head of my erect penis popped out of my pajama fly! I was so embarrassed that my face became hot. She stared wide-eyed at my helpless twitching penis as I lay there powerless to do anything and reached down and grabbed it by the shaft. I guess I have a pretty big dick for my age and she seemed to be very impressed with it. “Oh my!” she said with a sly tone in her voice. “Well we are a very bad boy aren’t we?” I was really embarrassed but really turned on too at the same time and just stood there speechless. Forcefully she pulled me over her lap on the couch with my shoulders propped up on the end of the couch. She pulled my pj pants all the way down and reaching underneath she started stroking my super hard dick with one hand, while spanking my naked butt with the other. “Bad boy!” she kept playfully saying while she lightly spanked my butt and stroked my dick. My dickhead now got wet with precum that she used as lube to stroke me ever further. She spanked and stroked me as I moaned in ecstasy till I arched my back and jutted my hips forward spurting all over the couch pillow! I was really embarrassed after, lying there handcuffed and bottomless with spooge all over me & the couch. She made me promise to not ever say anything about it or she would never baby sit for me again. I eagerly agreed. The she cleaned the couch off and flipped the cushion and told me I needed to go to bed.
Janienudiepants wrote:
Babysitter by Janienudiepants
Very nice story. I babysat a lot for my mom's divorced friends as a teen. Mainly single moms, occasionally everyone else. I dreaded some kids, and others I lived to die for, they were so cute. One pair of boys were four and seven, a bit like you, and cute as h*ll. At bedtime one thing you knew for sure who had a "hard-on." Their little flagpoles stood out of their pj tents once they found the hole. Of course, little boys button pjs have a huge hole in front -- they never button them, and their little d*cks found it all the time in tickle fights, wrestling playing around with them before bed or just sitting with me snuggled up watching TV. I grew up with the impression boys always had a hard-on.
I always enjoyed the cute little kids and what I saw. I imagine their mom played with them like I did. They weren't shy pulling each others pj bottoms down at all -- it was all great fun. They had such cute bottoms! And of course, they shouted with glee whenever they could pull something down from me!
lol
still enjoy remembering...
Janie
A board for stories about girls pantsing and stripping others or getting pantsed and stripped
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Subject: Babysitters who have spanked the boys they watch/watched
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Date Posted: 13:37:40 07/23/16 Sat
Is there anyone else here who babysits/has babysat kids who they had permission to spank?
Right after I started going to UCF a few years ago I used to babysit every day in the afternoon for a mother (a close friend of my mom who used to babysit me when I was little) who lived in the same neighborhood as the rental house I was staying in every day while she was at work, for a little less than a year.
There were two kids, a Amanda (11) and Joshua (10). For about the first two months, when their mother got home she would ask if they had been good for me, and if I gave her a bad report she would spank the one who misbehaved right in front of me, always over her knee and on the bare.
I saw her do this maybe 3 or 4 times, and then eventually she told me I might as well just give the spankings myself, but to please call her first and let her know if I thought they needed one.
So after that I babysat them for about 8-9 more months, and gave maybe 2 spankings a month. Usually it was Amanda I had to do it to, because she was just soooo bratty and disrespectful. I always did it the same way their mom did, bare bottom over the knee with my hand, and then corner time in the living room with their pants down after.
I never spanked unless I thought their mom would have in my place, and I always called her first and made sure she was ok with it, but the truth is I really did enjoy doing it. I would never admit it to anyone, but I always secretly hoped I would get to spank them when I went over. It was a total power trip, having that much authority over someone else and being able to make them take their pants down in front of me and see them naked, lol
I really enjoyed undressing them and having them over my lap, and seeing and touching their bare bottoms. I really liked Joshua, he was a really nice and sweet kid and I hardly ever had to spank him, but he had such a cute plump little butt, lol! It would bounce when I smacked it and turn really red, it was adorable! After I was done spanking I would always keep him over my lap and rub his bottom and lecture him, and really that part was just because I liked it. I hardly ever had to/got to spank him though, because he was always pretty good. When he was getting spanked he was obedient and didn't fight with me or make a fuss, but he did cry by the end usually.
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The most embarrassing corporal punishment I ever got was when I was 11. My mother was just starting to prepare me for my spanking, which had been coming both for sassing her and for playing ball in the house which resulted in a broken window.
When it came to administering the spanking, Mom always took my pants down herself. She said naughty boys were not allowed to do it. Anyway, just as her fingers were starting to unzip my short pants, the door bell rang.
My mother looked up. “That must be the babysitter – don’t you dare move!” I was so embarrassed when she returned with Sarah, my babysitter. Sarah was only four years older then me and I had a huge crush on her. She was wearing a pencil skirt, stockings and high heel pumps. She looked at me and smiled.
To my utter shame, my mother told her: “Bobby has been a very naughty boy and I was just about to administer his spanking when you arrived. I didn’t realise how late it was, and I won’t have time to whip him. Would you do me a favour and administer it for me?” Sarah looked at me and smiled, then said: “I would be happy to.” Mom told her to pull my pants and underwear down and spank me over her lap, then she left.
When my mother had gone, Sarah looked at me and said knowingly: “I think this spanking will do you a lot more good with me giving it to you. I know you have a crush on me!”
She sat down on the straight-backed chair previously occupied by my mother and called me over, then her fingers slowly finished unzipping my pants. Sarah took down my underpants and looked down – she smiled as she gazed at my growing erection. My embarrassment was complete. Then it was over her lap for my spanking. I felt her stocking-clad thighs under me and rubbed myself against them.
Sarah raised her hand and began to spank me slowly, pausing between spanks to let each one sink in. The fire built up steadily in my bare bottom but at the same time, I also felt something else as my penis rubbed up and down against her stockings as I wriggled. With hindsight, I was on the point of coming. However, just before I did, Sarah stood me up, told me to pull up my pants and go to my room until I could be a good boy.
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Today started off as a pretty normal Saturday. I was up in my room playing video games and Jenny, my babysitter, was downstairs doing something on her computer tablet; probably on Facebook or something. I was playing Mario Kart when she came upstairs in a huff and plopped herself down on my bed. I bounced slightly from the shockwave.
"Oh hey, video games." she said. "Can I join in?"
"Uhh, sure." I answered hesitantly. I had a sense that she was upset about something, but I wasn't dumb enough to ask her what was wrong. If she wanted to tell me what the problem was, she'd get around to it without my prodding. Jenny picked up the second controller and we played the game in silent for a few circuits. As it turned out, she was actually pretty good at the game. I don't know why I was surprised; Mario Kart's been a series for a long time, older than both of us combined.
"Ooohh, this takes me back." she whispered under her breath after we finished a race. "Thanks for letting me blow off some steam with you."
"You're too young to think about this, but if and when you ever get a girlfriend in the future, treat her right."
"What do you mean?" I ask, sitting up to stretch my limbs.
"Us girls, well... we like attention. We like getting treated like princesses and getting hugs and kisses and... other stuff."
"Grown up stuff." Guh, the grown up wall. Every time anyone wants to hide something, they just say it's a grown up thing.
"Come on, just tell me." I demanded. I wasn't going to argue I was grown up enough; no way was I going to get away with that.
"If you MUST know, my boyfriend, or soon to be ex-boyfriend, insists that we wait before we have s..." her voice drifted off, like she was struggling to continue. "Sex."
"It's something grown ups do to show how much they love each other. It's like kissing, but a lot more... intimate. And fun."
"It just is, now please drop it. It's bad enough that I mentioned it to you, and please don't tell anyone else that we talked about it." Jenny picked up her controller again Now are we gonna do another race or not?"
"Okay." I picked up my controller and started cycling through the maps. As I selected one map, I couldn't help myself; I was just too curious about this sex. "So why does he not want to have sex with you if it's so fun? Does he not love you?"
"It's some stupid pact he made at his college. He'll prove his faith to God and remain celibate until he gets married and until then, we're not going to have sex or kiss or hug; hell, we can't even hold hands, according to his stupid pact!"
"Oh, that sucks." I said with sincerity. "I'd have sex with you."
"W-WHAT!?" she exclaimed in a high pitched voice. "You don't say that to just anyone!"
"Yeah, but I'd still do it. I kinda like you, Jenny."
Jenny let out an exasperated giggle and buried her face in her hands.
"Nothing, I'm just... taking stock of my lot in life." she sighed through her fits of giggles. "My boyfriend becomes a monk and a little boy all but declares his love for me."
"Oh, you have no idea!" she laughed. "I'm almost inclined to take you up on that offer, just to stick it to my soon-to-be ex!"
I continued to stare at her with curiosity. I still didn't know what sex was, or why she was upset because her boyfriend wouldn't have sex with her and why he wasn't in the first place.
"Alright, here's my deal." Jenny said, sitting upright and grabbing her controller. "If you can win the next race, I'll have sex with you and show you what my ex has been missing!"
"Okay!" With an objective to shoot for, I was fired up. I selected the next map, specifically one that I was a real pro at. I didn't tell her that; I wanted to win. What I didn't know was this was apparently her best course, too.
"Hah! I'm not gonna lose to you on THIS course!" she said as she left me in her dust in the first two laps. Right as we began the final lap, I lucked out and got a pile of bananas and threw them down on the curve just before the finish line. My trap worked, and though she had a good lead ahead of me, she lost all of it as she tried to make the turn, slid into one of them and fell right off the course.
"Oh no!" she exclaimed as Lakitu placed her back on the course, but it was too late. I was able to dash right past her with a shield of green shells to stop me from getting wiped out by my own trap, and I stole the race right out from under her.
"Oh, you sneaky boy." she chuckled. "Alright, I didn't actually expect you to win, but a deal's a deal, I guess."
Jenny sat up to face me. She gave me a very serious dead-eyed stare.
"Now... before we do this, are you absolutely sure you want to do this?" she asked. I nodded my head. "Okay, then... turn off the console. You won't be interested in it once we begin."
After I put away the Wii U, I rejoined Jenny on the bed. She pulled me into her lap, and I felt a strong sense of elation. Maybe
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