Babysitter Humiliated

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Babysitter Humiliated

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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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by PhilMarlowe » Mon Mar 02, 2020 2:58 am

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Posted by
redcat

on 2004-11-26 20:59:03
Posted by
JackP

on 2005-07-04 04:01:58
Posted by
rk0237

on 2006-05-29 19:09:57
Posted by
redbehind

on 2006-06-20 18:05:09
Posted by
sergent sunshine

on 2008-11-07 02:12:32
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i was bathed by four different babysitters as i was growing up. i was an only child and my mom bathed me, so i realy didn't think much of it when the babysitters did it. i was bathed until i was almost 12, then supervised for a couple of years after that. a couple of the babysitters brought a friend sometimes.
I remember when I was a young boy; when I was bathed by the young sister of babysitter, I was embarrassed, because she was 13/14, just like me. I felt very humiliated when she washed between my legs; I started my puberty and I was ashamed!Sometimes, she commented about my first pubic hairs; and I had to be civil and smiling; it was horrible!
Yeah, I had the same thing. I was maybe 12, one of my last baths by a babysitter who was maybe older highschool and she brought her younger sister, same age as me. She had the younger sister give me a bath while she talked on the phone with a friend and watched and described it to her friend--omygosh was i embarrassed at first but it got to be a game. the sister washed my willie 2 or 3 times, under the forskin and all. then my butt, poking the washrag up inside a little. her older sister kept saying its not clean enough. the friend on the phone lived up the street and ended up coming over and all three girls gave me a bath all over. i got hard at the end and they thout that was pretty funny. the other one left befoe my parents came home and i was in my underwear so they never new.
Wen I was 16, I broke both my wrists and was in a cast so I could not do much for myself. It was summer & my mom worked so my neighbor who was 15 would look in on me and get me what I needed. One day mom told her she should bathe me until she got home. She got her friend who was also 15 to help. This was very embarrassing.
If you want to hear more, let me know.
I don't know what you boys are complaining about I am 13 and I would love an older girl or woman to bath me It might lead to other things.
are you kidding me! I would love to have a girl my age playing with my nuts! you got to be hard put to get a girl to do that normally! there is no way i would be embarrassed, I would die to have that happen, and i am 13, 14 in 2 months

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I'm 20 years old and I don't babysit as much as I used to but still on occasion do. I have straight, light brunette hair that hangs just past my shoulders, brown eyes and a curvy build. I first started babysitting when I had just turned sixteen, I used to do it regularly, at least once a week, for one family who had three kids, an eight year old, a ten year old and a twelve year old. The ten year old was a girl and the other two were boys, I'll call them Matthew (8), Katie (10) and David (12) rather than telling you their real names. The first few weeks with them went seamlessly, no problems at all, they always did what they were told and mostly wanted to watch a film then go to bed as I was usually just sitting for them in the evenings. About two months after I started sitting for them, I was asked to sit for a whole day, I think it was a Saturday. Anyway, I agreed and turned up early in the morning wearing a plaid shirt with the sleeves rolled up and a pair of denim hotpants. I was barefoot because it was nice out and I decided to wear sandals. When I got there the kids were still asleep so their parents went upstairs and told them they were leaving and then left me in charge, they also told me that the kids had homework to do and requested I try and make them do it before bedtime. Katie was the first to get dressed and come down to see me, soon followed by Matthew who wanted to watch cartoons so they settled down in front of the TV. Finally David joined us and I fixed them a snack. Once the cartoons finished I asked them nicely to do their homework which they never minded much before. Katie and Matthew went and sat at the kitchen table and started but David remained on the couch. I asked him again if he could go get his homework out of the way, that way we could play a game later. "Can't I show you what I learnt at scouts?" In hindsight I should've said no and persisted until he got his homework done but I said something like "Okay, sure!". So, he ran to his room and came back with a bag. He held out one of his mother's silk scarves and requested I tie it over my eyes and hold out my hands so I wouldn't ruin the surprise. I took the scarf and tied on a blindfold, he told me to tie it tighter because I was cheating and was going to peek so I tightened it up so I couldn't see, then held out my hands. Next thing I knew, I felt something pulled around my wrists, I asked him what he was doing and tried to reach up to pull off my blindfold but he tugged my hands away from my face and told me to hold still or I'd ruin the surprise. I was understandably uneasy at this point as I felt the material wind around my wrists a few more times before being cinched tight. He slid down my blindfold so it hung around my neck when he was done and said "Tada! I learnt some new knots!" David had bound my wrists with white rope and pulled down my blindfold so I could see his handiwork and the secure knot holding tight. I said something like "Wow, that's great, now you can untie it and go do your homework!" Of course he didn't, he told me to hold still while he shows me how the knot is tied this time, grabbing my ankles and pulling rope around them, I tried to pull away but he just pulled the rope tighter and told me to watch not struggle. It wasn't long before he'd knotted that rope too. "Okay, I'm very impressed, now untie me." I tried to regain control. Next thing I knew he was covering my mouth with his hand and looking behind me, I assumed that Katie and Matthew had finished their homework. My suspicions were confirmed when I hear Katie say "What are you doing David?" and Matthew added with a tone of excitement "Are you playing a game?" I saw a grin appear on David's face but moved my head out of his grip. "No we're not playing a game, now could you untie me please?" Matthew looked disappointed until David said "She's lying! we're Indians and she's a mean old cowgirl trying to invade our land!" Katie and Matthew gasped then Katie asked "What do we do?!" "We have to tie her up and make sure she can't get away!" David encouraged them. They ran off to the garage and returned minutes later with climbing and skipping ropes. "I'm not trying to invade your land! I promise!" I pleaded as they approached me with the ropes, they gave David the ropes and he tied just above my knees, then pulled a rope around my middle and tied it so that it held my arms down. "Okay! You win, this was a lot of fun but game over, untie me now!" "She's calling for back-up!" Matthew exclaimed. "What? No I'm n-" before I could finish my sentence a balled up silk scarf was stuffed in my mouth and my former blindfold pulled up to cover my mouth and hold it in. My former blindfold had become an over the mouth gag but David decided for it to actually work he'd need to tighten it up so he undid the knot, pulled it as tight as he could, making it more like a cleave and re-knotted it. There was one more length of rope that was added to me, tying my ankles to the coffee table so I couldn't "hop away". And that's when the tickling began! I have very ticklish feet and with them being bare that wasn't a good sign as they dived in tickling all over my soles until I was crying with laughter, powerless to stop them. Then they got bored and just left me "Cmmmmmffff bgggggg!" I called for around an hour but they weren't coming back so I tried to get free without any success. I was left tied up until their parents came home that evening and found me. They untied me and I even got a little bonus, they practically begged me to babysit again and not be put off by the experience. Truth was, this was my first babysitting tie up and I actually didn't mind it too much and so agreed to babysit for the kids again.

Jewell was visiting Sophia. They had been friends for years but Jewell had a tendency to get bored easily, even when with Sophia who was one of her closest friends. On this one particular occasion Sophia was tired and couldn't deal with Jewell's constant moaning about being bored.

"If you're so bored why don't we do something?! Anything you want!" Sophia gave in.

"Yay! How about we dress up? I bagsy your ultra sexy maid uniform!" Jewell grinned.

"Fine… and what should I dress up as?"

"Do you still have that cat burglar outfit?"

"You mean the black leather catsuit?"

"Yeah!"

"Yeah… I've still got it…"

"You wear that and I
My birthday passed a few weeks back and the only thing I wanted was to tie up a damsel. Not for any nasty business. I was always into tying up the opposite sex. Some may say it is too domineering or tying myself a damsel is degrading to the feminine gender. Maybe it is. If you think deep about it. To me though, I never thought tying up a girl was degrading I only thought it was something fun to do when I was little. Now that I am going through puberty, I try not to think about it. I only know what I like, and I am a man lead by my desires. So, when my younger sister started maturing as she entered high school I took note. Mind you, I never took note in the wrong way. I just thought my sister is growing to become a fine young lady. It started one day when we sat in her room reminiscing about our past. She brought up the past tie-up games. When we were children playing with the neighborhood kids. She reminded me of how I would always tie up the girls in all sorts of ways. "We always got
Brooke held her phone to her ear, nodding and agreeing with the person on the other line.

"Alright Mrs. Miles, 3 o'clock 'till 8 on Saturday? Okay. I'll see you then!"

Brooke hung up on Martha Miles, as she sat down on her bed. She'd just gotten a call from Martha, asking her to babysit her three children, Thomas, at the age of seven, Kate, who was ten, and Tilly, who was twelve. The seventeen-year-old girl thought she'd struck a goldmine, as Mrs. Miles was paying twenty-five dollars an hour, and she was babysitting for five hours, giving her a total of one-hundred and twenty-five dollars by the end of the day. Brooke grinned, as she texted
This is a true story about my first time getting tied up whilst babysitting. Hope you enjoy!
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I admit it, that was a cool story!

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