Stripping the Babysitter by SDS
Re: Stripping the Babysitter by SDS
SDS
Stripping the Babysitter - 1 - A Bad Deal
Thu Apr 26, 2012 6:36pm
At the age of 15 I was very mature and sensible. Because of this when our neighbour had to go away for the weekend I was asked to stay over a couple of nights and babysit Kerry. I had not really seen Kerry for a couple of years and I remembered her being an annoying little brat. She had always been small when we were growing up so I hadn’t realised she was only two years younger than me. However since then she had grown up and looked nearer my age then a 13 year old. As I went around she was whining to her mum telling her she was too old for a baby sister, her mum still treated her like a kid and told her to listen to me as I was the adult here. She glared at me with evil eyes and stormed off to her room. Her mum gave me £100 half for my pay and the other to get food and things for the weekend and left.
This was easy and good money, the girl obviously didn’t need proper looking after as long as I made sure she was fed. I plonked myself on the couch and turned on the sci-fi channel. After about half an hour Kerry came down the stairs and instantly walked over to me. “My friends are coming around to watch Twilight with me so I want the telly now” I looked up at her, grinned and said. “Nope I’m in charge this weekend, and we’re defiantly not watching that rubbish, destroyed the vampire genre that did” she glared “This isn’t fair it’s my house” I laughed and said “So I’m the baby sitter your mum told me you’d be in big trouble if you’ve been a naughty little girl.” This made her even more mad. “I want to watch Twilight with my friends!” I looked over at her “So team Edward or team Jacob?” she looked shocked for a moment but before she could answer I said. “Personally I’m for team: the guy who nearly hit Bella with his van” and laughed turning back to the TV.
She went back to her room until the door bell rang. Suddenly my peace was invaded by five girls. For a while they kept asking me to let them watch TV and were being purposefully loud. Then Kerry came up to me and proposed a deal. “Ok how about a wager, If I win you let my friends stay over and we can watch Twilight. If you win we’ll leave you alone and I’ll do what you want all weekend” I looked at her intrigued. “What like my little servant brining me drinks while I chill out?” “Yep”
It sounded brilliant to me even if I lost it wouldn’t be the end of the world. “Ok what’s the bet?” Kerry seemed to think for a moment. “Ok let us tie your hands behind your back, if you can untie yourself in 10 min you win if not your lose.” I agreed thinking foolishly that girls would have no chance. They came down with a bathrobe belt and began tying it behind my back. Little did I know that Jane the smallest of the girls was a girl scout, and very good at knots. So there I was trying my hardest to untie the knot, with the five younger girls laughing their head off at me. “Ok you win now untie me.” Kerry just laughed in my face. “Why? You’re at our mercy now” I started to pani...ie me now or I’ll tell your mum.” This just made her laugh more, every time I tried to stand up one of the girls pushed me back onto the couch without my hands it was very hard to resist. “Aww his going to tattle to mummy” she pulled the girls together and started whispering. After a few moments and a few quick games of rock, paper scissors.
A blond girl stepped forwards, her cheeks were already blushing and I wasn’t sure what was happening. She was tall for a thirteen year old, and skinny. She wore a dark pair of leggings and a white vest top. “Go on then Emily” shouted Kerry. I noticed Kerry had gotten a camera ready. Emily suddenly pulled her top over head revealing a pink push up bra. I stared wide eyed, I couldn’t keep my eyes off her, although her cleavage was fairly small even boosted by the bra but it was the first time I had ever seen a real girl like this. She jumped onto my knee and kissed me for a second. I was confused in one quick surreal moment nothing made sense. Kerry took the picture and Emily turned to her to ask if it was a good one? She was now covering her boobs. I couldn’t help it despite her being only thirteen her state of undress exited me and her being on my knee noticed it. “Oh my god he’s got a boner.” Emily suddenly shouted jumping off me. I tried to cover it but it was no good I had my hands tied behind my back. The girls burst into hysterics; I managed to put my knees up so I was curled up on the couch to cover my excitement. I was even more red faced than Emily now as she put her vest top back on.
SDS
Stripping the Babysitter - 2 - Tied up and Stripped
Thu Apr 26, 2012 6:40pm
“Untie me or you’re in big trouble I threatened.”
“I’m in trouble, I have photographic proof of you having a girl over and doing naughty things, while you were supposed to be looking after me”
My mouth went dry, they had blackmail over me and I was in a very venerable position. “Awww what’s wrong did looking at Emily’s bra exited you, you big perv?” said Kerry and the girls burst into waves of laughter again. A couple of them tried to pry my legs away from my body but I was trying my hardest to keep covered.
“You’re no fun, ok how about a deal if you stand up straight for us for thirty seconds we’ll untie you ok?”
I was terrified but could see no other choice. I stood up in front of the laughing teenagers as they ridiculed the noticeable budge under my jogging bottoms. I started counting but from nowhere, although I really should have seen it coming I was pantsed. My Jogging bottoms fell straight to my knees, in a rush to try and cover up I fell backwards flat on my underwear clad bum. Before I knew what happened I was trying my hardest by crossing my legs to stop the girls taking them all the way off. It was no good soon I was flat on the carpet in only my underwear and longish T-shirt. Curled up again trying to pull my T-shirt down to and only just succeeding with my hands behind my back.
Emily held up my gray joggers like a trophy, “I’m sure I saw little kiddy undies!” shouted Jane with a massive smirk on her face. Kerry’s eyes went wide and down towards my crotch. “Oh my god aren’t you in boxers? Wow this really will be embarrassing for you then.”
“Give me back my clothes and untie me now!” I shouted my voice half shaking from embarrassment and fear.
“Oh no you don’t give the orders tonight. Quick girls get his legs tied together as well” I tried to get up and make a run for it but this was hard to do without your arms for balance and soon I was tackled to the floor face down. They piled on me holding in position while Jane again tied my legs together this time with my jogging bottoms. “Done!” shout Jane jumping off me. “Quick lift up his top and see what kind of undies he’s in.” the rest of the girls got off my back but I could feel someone grab my T-shirt. “No please!”
“Aww what’s wrong? You got to see Emily’s underwear so fairs is fairs.” With that Kerry pulled my Tshirt slowly up my back until it was over my head and stuck around my tied arms. I was so exposed practically naked in only a small pair of white briefs that I should have thrown away a long time ago but was all I had in my draw that morning. They girls burst into hysterics making comments of them looking like white panties, and how silly I looked.
Kerry got her camera out again and started taking pictures as I shouted for her to stop. “Quick turn him onto his back let’s see if he’s still got a boner” I tried to resist but it was useless, luckily the embarrassment of what had happened and the girls all being fully dressed again had made my excitement calm down.
“Aww your no fun.” Said Kerry getting a photo with my face in to add to her blackmail list. “Emily flash him again”
“No way it’s someone else’s turn” said Emily she gave a big grin and flashed eyes towards Jane who was stood over me wearing a flowery summer dress. Before she knew what hit her, the dress was pulled up to her stomach exposing her pale skinny legs and her Hannah Montana white panties to me. I felt even more guilty and weird for being turned on by Jane as she was the youngest looking of them but I couldn’t help it, the two girls tried to pull the dress all the way off the screaming Jane they managed to get it briefly to her training bra being exposed before they let her go almost in tears red faced.
Kerry laughed her head off “Nice knickers Jane now I see why you’re was always so shy when getting dress with us.”
“What did you do that for” sobbed Jane almost crying but managing to hold off.
“That’s why!” she said pointing down at me. “Look the pervs back up.” All the girls crowded around me again laughing their head off at my boner covered only with a small pair of white undies. Even Jane cheered up joining in my ridicule.
“While it’s up maybe we should pull them down too and see what his little boy undies are really hiding” said Kerry with a massive grin on her face.
“No please not that please stop!!!” I said almost in tears myself it was bad enough girls looking at my underwear and having a boner but to be totally naked was a shame worse than anything I could think of.
“Ok but you will be our slaves, anything we want you’ll do or else these pictures will be all over Facebook and everyone will see you. Is that a deal? ”
“Yes” I said relief washing over me. Little did I know the night was about to get a lot worse.
SDS
Stripping the Babysitter - 3 - Blackmail
Thu Apr 26, 2012 6:42pm
Chapter 3 – Blackmail
“Ok these are the ground rules. You cannot cover your underwear or you’ll be punished. If you are a naughty perv and get a boner again you will be punished worse and worse each time until you learn your lesson, and finally if you get to exited and spunk in your little undies you will have to get totally naked, washed off and then really punished so you better not be a perv again tonight or else. If you do all we say we’ll delete the pictures and promise not to tell anyone”
I nodded solemnly trying to keep the pure fear from my face. I know I had no choice, the girls untied me, instinctively I tired to cover but a warning look moved my hands away, it was even worse now, before I felt like I had no choice but now I had to stop myself and keep exposing my undies to the girls. The girls made me get them drinks and snacks laughing at me as each time they wanted it with ice or with the crusts cut off.
After a while the girls started making me do things just to embarrass me, Kerry told me to go outside and make sure the gate was locked. “Please let me put on some more clothes I begged”
Kerry’s smile never disappeared “Ok then” she threw me my trainers. All the other girls burst out laughing. I swallowed my shame and made a run down the garden path covering my undies the best I could. The gate was locked and when I got back to the door they had locked me out.
“Please let me in” I begged fear welling in me.
“Nope you’ve been naughty and covered up this is you punishment to stand out there for five” said Kerry leaning out the window to laugh at me exposed to anyone walking past.
“Please its freezing” also it had started to rain lightly but I didn’t want to give the girls any more ammunition.
“Ok instead you can come in the back and use the dog door, and remember no covering.” laughed Kerry
I knew what the problem with this was, to get to the back I had to leave from the front gate and go down the street at the side of the house. I ran forcing myself not to cover, a car went past but before I knew it I was at the back door. I crouched down and was about to crawl through the dog door when I was interrupted.
“You’ve got to come in feet first” shouted someone from the other side followed by loads of laughter. I obeyed squeezing through the dog door legs first which isn’t an easy feat. Just as I get half my body through on of the girl’s jumps on my legs getting me stuck with my little undies on display on the inside.
“Maybe we should just strip you naked after all what do you think?”
“No please don’t we had a deal!” I begged panic rising in me again.
“I suppose” I felt a finger on the waistband of my underwear I was terrified but the close to imitate contact felt good which made me even more nervous.
“So perv did you enjoy seeing the girls in their bra and knickers?”
I didn’t reply. “answer me! Or else”
“Yes ok I did” I confessed knowing that if I tried to deny it they would only make it worse for me.
“Did you like Emily kissing you, showing her little boobs in that pink bra?”
I realised what Kerry was doing but I couldn’t help myself being turned on again by her words and the images from earlier.
“Oh maybe we should all get undressed for you, hmmm, right now I’ve just taken off my top would you like to see…” Kerry burst out laughing “oh dear you’ve been a bad boy again!”
“Here is your punishment” I felt the waistband of my undies lift up, I was terrified they was going to expose my boner but instead I felt an ice cube slide in. I screamed the freezing coldness against my penis was awful, soon my boner was killed and the ice melted giving me damp undies. The girls let me come all the way in laughing their heads off at me.
SDS
Stripping the Babysitter - 4 - Awful punishments
Thu Apr 26, 2012 6:45pm
Chapter 4 - Awful punishments
After about half an hour the girls started dancing to the music channel, they made me watch them. I know they did it on purpose pulling off provocative dance moves, especially Kerry bending over right in front of me and flashing me her cleavage. Someone tripped up Jane, making her flash me her panties briefly again as she stood back up. The girls noticed my excitement and made me stand up again.
“You have been very bad! You need to cool off and stop perving on us !!!” said Emily with a massive grin on her face.
“Ok now it’s chucking it down your punishment is to go stand in the rain until your boner goes down” said Kerry leading me to the front door again. It was humiliating but luckily didn’t take long for it to go down. Just as I was coming back to the door it opened I was hit by a full bucket of water to the undies. I had managed to keep them dry enough to not be see threw but now the white had turned practically transparent.
I covered up, I couldn’t stop myself, if I hadn’t they would have seen through my undies. They let me come in I was freezing and shivering. They had rooted through my bag and had binned a couple of pairs of boxers, all I had left was one pair of grey briefs.
“Ok now before you catch your death of cold take off them undies.”
I started at them in dread, unable to move or speak.
“Here” Kerry said throwing me a towel to cover up. “but you have to do it in here” reluctantly I removed my undies and dried myself. The girls grinned like chesser cats not taking their eyes away from me. Finally dried and naked they gave me my other pair of undies to wear. They made me turn around so I wasn’t facing them and then Kerry grabbed my towel and pulled it away from me leaving me naked saying it was punishment for covering earlier but don’t worry they’ll only see my bum. Totally humiliated I pulled my undies up my totally naked body as quick as I could. The girls where taunting and humiliating me saying nice bum, it was truly horrible.
“Well then so now you’ve been totally naked how do you feel”
“humiliated” I said turning back to them in my undies.
“Oh by the way I’ve got a nice shot of your bum here” the girls gathered around the camera to laugh.
“Oh that’s priceless” said one of the other girls with ginger hair.
“I know what we can do now” said the last girl who was quite chubby with short dark hair. “We can tell embarrassing stories to see if anyone’s been embarrassed worse then this”
“Like can you remember the time when poor little Emily was getting dressed and my brother walked in, all she was in was a pair of panties and her PJ top”
“Oh I get it” said Kerry grinning wildly at me. The girls had a quick hushed convocation. I knew it wasn’t going to be good what ever they were whispering about.
“Ye but that’s not as embarrassing as when we stole Kerry’s bikini top while she was sun bathing at the beach. Remember Kerry you had to chase us all the way up the beach covering you naked boobs. ” said Lisa the ginger girl.
Kerry laughed it off, I tried to not picture these stories in my head but I couldn’t help it.
“Remember the first time you wore a thong Lisa? You were showing us in the living room and my dad walked in when you had it lifted up showing you bum”
I was starting to blush again the girls were doing it on purpose I tried to ignore it but soon my excitement was showing again.
“Right that’s it you bad boy, you need to stop being such a perv or there is going to be trouble.” Kerry said while walking over to me. “So you like to here about Lisa’s thong well let me show you what it’s like.” I daren’t resist as she grabbed the back of my undies and gave me a painful wedgie.
“Don’t be so shy, we’ve all seen your bare bum anyway. No here’s your punishment, hands on head, stand up straight and we’re going to give you a good spanking until your boner goes down” Humiliated I tried to refuse
“Please this has gone too far” I pleaded
“Do it or we’ll all gang up on you strip you butt naked, tie you up and put you on webcam to everyone at school” said Kerry with a massive grin on her face. I had no doubt she would go through with it.
I accepted my fate putting my hands on my head as the girls took turns swatting my exposed bum from the wedgie. It hurt like mad I hoped it would be enough to quickly get rid of my boner but as it started to go down, Kerry and Lisa did paper, scissors, rock and suddenly Lisa swore. Lisa turned to face me and to my surprise slowly pulled her shorts down to the floor revealing her yellow cotton panties. I tried to stop it but before I knew it what was happening it was up again. The girls didn’t stop laughing, Lisa pulled her shorts up laughing off the embarrassment herself.
The smacking intensified, Kerry pulled my undies high up my red checks, I was almost in tears from the pain, I was so humiliated I would have done anything to stop it. “aww its going down again. Someone flash him a bra” said Kerry laughing, after a few more paper, scissors, rock games Emily lifted her top up exposing her pink push up bra again, I knew what was coming but couldn’t stop myself enjoying the image. They continued again, tears dripped down my eyes and I winced with every smack. The worst thing was Emily didn’t get redressed and so I couldn’t lose my boner. Finally though she did and after some hard smacks with a wooden spoon I was in real pain.
“aww don’t cry little perv I know what will cheer you “UP” ” laughed Kerry. After a few more games it landed on Lisa again, if only my boner had fully gone down I would have been spared this humiliation. Again Lisa pulled off her shorts but this time didn’t stop there, she then lifted her top revealing a matching yellow bra. Unlike Emily she hadn’t padded it but her natural cleavage was enough, the sight of her only in her panties and bra, red faced and embarrassed turned me on so much I couldn’t stop getting hard, however really unluckily for me the excitement was too much and the front of my undies had been clearly stained with Pre-cum.
SDS
Stripping the Babysitter - 5 - Naked Spanking
Thu Apr 26, 2012 6:47pm
Chapter 5 Naked Spanking
“Oh my god Look he’s cummed his undies.” Shouted Kerry excitedly pointing at my undies. “you know the rules, time to get naked”
“No please no” I said tears of humiliation and pain dripping down my face. “It’s only precum I haven’t done it properly please no!”
“Take them off now” Kerry replied with a hungry look in her eye.
I don’t know what I was thinking but I tried to make a break for it, I ended up tackled to the floor. They grabbed me turning me over so I was face up,
“Resist and the whole school and not just us will see you naked”
I froze, Kerry reached down and grabbed my undies. Without mercy she pulled them straight down my legs. The girls screamed laughing at my small penis as it came on display. It was down again but this somehow made it worse, they laughed and all I could do was cry. Lisa still wasn’t dressed and suddenly she came over to me her cleavage inches from my face. I couldn’t keep my eyes off her boobs clad only in a yellow bra, I’m sure she did it on purpose.
My boner shot straight back up to the girl’s great amusement. Lisa got dressed and Kerry made me stand up with my hands on my head and boner standing up in front. It was so humiliating; they threatened to spank me again if I tried to cover up so all I could do was stand there totally humiliated in front of them with my boner sticking up in the air in front of the five girls. Kerry ran upstairs and I could here the shower running after a few seconds, the remaining four girls got stared with wide grins at my naked humiliation. Jane stared the hardest and blushed almost as much as me, I was obviously the first boy she had seen naked and my boner furthered my humiliation.
Kerry returned and quickly snapped a picture before I could cover, for trying I got another large smack across the naked bum. I had managed to stop crying and before I knew what was happening I was led upstairs to the bathroom. “Ok girls are you ready to see a disappearing act!” said Kerry laughing. “I’ve herd that when it’s really cold boy’s willies shrivel up and get really small.”
I suddenly realised that the shower was running cold water. “No please don’t d…”
“Shut up slave, unless you want your butt naked boner picture on Facebook?”
I shut up quickly my face was red. Kerry pointed at my lack of boner and frowned, “That won’t do I want to see what happens if you start big and then we freeze it”
Kerry whispered something to Jane the youngest looking girl and eventually she nodded grinning. “It’s your lucky day perv, Jane’s going to strip for you.” I couldn’t believe it Jane pulled her arms out of her dresses strap and slowly lowed it exposing just the top of her bra. Then in one swift motion taking Jane totally by surprise Emily and the ginger girl had grabbed the dress pulling to straight down in one swift motion.
Jane had only been pretending to undress but had actually been tricked and in one swift motion her summer dress was pulled down her body to her feet. Her face went from a grin to one of shock and finally to white faced horror as she stood in front of me in her little Hanna Montana panties and white bra showing her small breasts and lack of cleavage. She screamed trying to fight them but they held her between them laughing, Jane was short and skinny with very pale skin and her innocent look made her humiliation all the more real. When they let her go she got dressed quickly tears running down her face, they then made me get in the freezing shower. My new excitement was met with laughter as the freezing water hit me.
“Oh my god his willy has gone from standing up to small to tiny !!!” shouted Kerry pointing at my nakedness.
SDS
Stripping the Babysitter - 6 - Dressed Like a Girl
Thu Apr 26, 2012 6:48pm
Chapter 6: dressed like a girl
They let me get out of the shower after my penis was small and shrunk from the cold. They quickly dried me and then took the towel leaving me butt naked. The girls found my predicament hilarious ordering me around again butt naked. When I came back into the living room with some drinks they had taken all the clothes out of my bag and they where no where to be seen.
The night was starting to get cold and I physically shivered from my nakedness. The girls were whispering which wasn’t a good sign. “Ok do you want to be naked all night?”
“No I said” a ray of hope breaking my bleakness.
Kerry came down stairs with some of her clothes. Suddenly I realised what she wanted me to do.
“I can’t wea…”
“Slave are you really going to say no?”
The girls burst into hysterics as they looked through different underwear for me to wear. In the end they settled for an old pair of pink Disney Princess panties with Cinderella on the front. Unlucky for me I was skinny and so they easily fitted on even though they had been Kerry’s when she was twelve although back then she had been chubby. I quickly put them on glad to have something to cover up. However my nightmare had only just begun the girls found me a matching bra and stuffed it to make it look like I had small tits. My hair had always been kind of long and curly but when the girls straightened it suddenly it looked like short girl hair. They put some make up on my laughing at me at every stage sat there in only a bra and knickers.
My body being skinny and my height fairly short all added up to me looking like a girl, it was horrible; they girls teased me saying I looked like a pretty girl. When they showed me the mirror I barely recognised myself, I really seemed to fit in with the 13 year olds around me. For the next hour the girls ordered me around loving every moment of my humiliation. As I walked back into the room the girls were staring at me with huge grins on their faces.
“we can’t decide what to do with you next, we was thinking of maybe making you model different kinds of underwear, maybe a thong? What do you think of that?”
I stood petrified, it was humiliating enough being in Disney knickers. The girls burst into hysterics. “Nah maybe we should just make you get naked again, I’m sure you bare bum wants another spanking” said Emily.
“Don’t be silly Ems he makes a lovely thirteen year old girl”
To my relief they left it at that but after about half an hour they declared it was time to get changed for bed and the girls disappeared upstairs. After a while they came back down in Pj’s varying from little shorts to a night dress.
The doorbell rang and I froze with fear.
“Oh that will be Clair, we’ve invited her to stay over with us”
Somehow a fresh new face to be totally humiliated to made me feel awful. I was terrified they was going to make me go to the door like this but instead they gave me a long T-shirt to use as a night gown and Kerrie told me to pretend I was her little cousin or else if I was found out I would be butt naked again.
Stripping the Babysitter - 1 - A Bad Deal
Thu Apr 26, 2012 6:36pm
At the age of 15 I was very mature and sensible. Because of this when our neighbour had to go away for the weekend I was asked to stay over a couple of nights and babysit Kerry. I had not really seen Kerry for a couple of years and I remembered her being an annoying little brat. She had always been small when we were growing up so I hadn’t realised she was only two years younger than me. However since then she had grown up and looked nearer my age then a 13 year old. As I went around she was whining to her mum telling her she was too old for a baby sister, her mum still treated her like a kid and told her to listen to me as I was the adult here. She glared at me with evil eyes and stormed off to her room. Her mum gave me £100 half for my pay and the other to get food and things for the weekend and left.
This was easy and good money, the girl obviously didn’t need proper looking after as long as I made sure she was fed. I plonked myself on the couch and turned on the sci-fi channel. After about half an hour Kerry came down the stairs and instantly walked over to me. “My friends are coming around to watch Twilight with me so I want the telly now” I looked up at her, grinned and said. “Nope I’m in charge this weekend, and we’re defiantly not watching that rubbish, destroyed the vampire genre that did” she glared “This isn’t fair it’s my house” I laughed and said “So I’m the baby sitter your mum told me you’d be in big trouble if you’ve been a naughty little girl.” This made her even more mad. “I want to watch Twilight with my friends!” I looked over at her “So team Edward or team Jacob?” she looked shocked for a moment but before she could answer I said. “Personally I’m for team: the guy who nearly hit Bella with his van” and laughed turning back to the TV.
She went back to her room until the door bell rang. Suddenly my peace was invaded by five girls. For a while they kept asking me to let them watch TV and were being purposefully loud. Then Kerry came up to me and proposed a deal. “Ok how about a wager, If I win you let my friends stay over and we can watch Twilight. If you win we’ll leave you alone and I’ll do what you want all weekend” I looked at her intrigued. “What like my little servant brining me drinks while I chill out?” “Yep”
It sounded brilliant to me even if I lost it wouldn’t be the end of the world. “Ok what’s the bet?” Kerry seemed to think for a moment. “Ok let us tie your hands behind your back, if you can untie yourself in 10 min you win if not your lose.” I agreed thinking foolishly that girls would have no chance. They came down with a bathrobe belt and began tying it behind my back. Little did I know that Jane the smallest of the girls was a girl scout, and very good at knots. So there I was trying my hardest to untie the knot, with the five younger girls laughing their head off at me. “Ok you win now untie me.” Kerry just laughed in my face. “Why? You’re at our mercy now” I started to pani...ie me now or I’ll tell your mum.” This just made her laugh more, every time I tried to stand up one of the girls pushed me back onto the couch without my hands it was very hard to resist. “Aww his going to tattle to mummy” she pulled the girls together and started whispering. After a few moments and a few quick games of rock, paper scissors.
A blond girl stepped forwards, her cheeks were already blushing and I wasn’t sure what was happening. She was tall for a thirteen year old, and skinny. She wore a dark pair of leggings and a white vest top. “Go on then Emily” shouted Kerry. I noticed Kerry had gotten a camera ready. Emily suddenly pulled her top over head revealing a pink push up bra. I stared wide eyed, I couldn’t keep my eyes off her, although her cleavage was fairly small even boosted by the bra but it was the first time I had ever seen a real girl like this. She jumped onto my knee and kissed me for a second. I was confused in one quick surreal moment nothing made sense. Kerry took the picture and Emily turned to her to ask if it was a good one? She was now covering her boobs. I couldn’t help it despite her being only thirteen her state of undress exited me and her being on my knee noticed it. “Oh my god he’s got a boner.” Emily suddenly shouted jumping off me. I tried to cover it but it was no good I had my hands tied behind my back. The girls burst into hysterics; I managed to put my knees up so I was curled up on the couch to cover my excitement. I was even more red faced than Emily now as she put her vest top back on.
SDS
Stripping the Babysitter - 2 - Tied up and Stripped
Thu Apr 26, 2012 6:40pm
“Untie me or you’re in big trouble I threatened.”
“I’m in trouble, I have photographic proof of you having a girl over and doing naughty things, while you were supposed to be looking after me”
My mouth went dry, they had blackmail over me and I was in a very venerable position. “Awww what’s wrong did looking at Emily’s bra exited you, you big perv?” said Kerry and the girls burst into waves of laughter again. A couple of them tried to pry my legs away from my body but I was trying my hardest to keep covered.
“You’re no fun, ok how about a deal if you stand up straight for us for thirty seconds we’ll untie you ok?”
I was terrified but could see no other choice. I stood up in front of the laughing teenagers as they ridiculed the noticeable budge under my jogging bottoms. I started counting but from nowhere, although I really should have seen it coming I was pantsed. My Jogging bottoms fell straight to my knees, in a rush to try and cover up I fell backwards flat on my underwear clad bum. Before I knew what happened I was trying my hardest by crossing my legs to stop the girls taking them all the way off. It was no good soon I was flat on the carpet in only my underwear and longish T-shirt. Curled up again trying to pull my T-shirt down to and only just succeeding with my hands behind my back.
Emily held up my gray joggers like a trophy, “I’m sure I saw little kiddy undies!” shouted Jane with a massive smirk on her face. Kerry’s eyes went wide and down towards my crotch. “Oh my god aren’t you in boxers? Wow this really will be embarrassing for you then.”
“Give me back my clothes and untie me now!” I shouted my voice half shaking from embarrassment and fear.
“Oh no you don’t give the orders tonight. Quick girls get his legs tied together as well” I tried to get up and make a run for it but this was hard to do without your arms for balance and soon I was tackled to the floor face down. They piled on me holding in position while Jane again tied my legs together this time with my jogging bottoms. “Done!” shout Jane jumping off me. “Quick lift up his top and see what kind of undies he’s in.” the rest of the girls got off my back but I could feel someone grab my T-shirt. “No please!”
“Aww what’s wrong? You got to see Emily’s underwear so fairs is fairs.” With that Kerry pulled my Tshirt slowly up my back until it was over my head and stuck around my tied arms. I was so exposed practically naked in only a small pair of white briefs that I should have thrown away a long time ago but was all I had in my draw that morning. They girls burst into hysterics making comments of them looking like white panties, and how silly I looked.
Kerry got her camera out again and started taking pictures as I shouted for her to stop. “Quick turn him onto his back let’s see if he’s still got a boner” I tried to resist but it was useless, luckily the embarrassment of what had happened and the girls all being fully dressed again had made my excitement calm down.
“Aww your no fun.” Said Kerry getting a photo with my face in to add to her blackmail list. “Emily flash him again”
“No way it’s someone else’s turn” said Emily she gave a big grin and flashed eyes towards Jane who was stood over me wearing a flowery summer dress. Before she knew what hit her, the dress was pulled up to her stomach exposing her pale skinny legs and her Hannah Montana white panties to me. I felt even more guilty and weird for being turned on by Jane as she was the youngest looking of them but I couldn’t help it, the two girls tried to pull the dress all the way off the screaming Jane they managed to get it briefly to her training bra being exposed before they let her go almost in tears red faced.
Kerry laughed her head off “Nice knickers Jane now I see why you’re was always so shy when getting dress with us.”
“What did you do that for” sobbed Jane almost crying but managing to hold off.
“That’s why!” she said pointing down at me. “Look the pervs back up.” All the girls crowded around me again laughing their head off at my boner covered only with a small pair of white undies. Even Jane cheered up joining in my ridicule.
“While it’s up maybe we should pull them down too and see what his little boy undies are really hiding” said Kerry with a massive grin on her face.
“No please not that please stop!!!” I said almost in tears myself it was bad enough girls looking at my underwear and having a boner but to be totally naked was a shame worse than anything I could think of.
“Ok but you will be our slaves, anything we want you’ll do or else these pictures will be all over Facebook and everyone will see you. Is that a deal? ”
“Yes” I said relief washing over me. Little did I know the night was about to get a lot worse.
SDS
Stripping the Babysitter - 3 - Blackmail
Thu Apr 26, 2012 6:42pm
Chapter 3 – Blackmail
“Ok these are the ground rules. You cannot cover your underwear or you’ll be punished. If you are a naughty perv and get a boner again you will be punished worse and worse each time until you learn your lesson, and finally if you get to exited and spunk in your little undies you will have to get totally naked, washed off and then really punished so you better not be a perv again tonight or else. If you do all we say we’ll delete the pictures and promise not to tell anyone”
I nodded solemnly trying to keep the pure fear from my face. I know I had no choice, the girls untied me, instinctively I tired to cover but a warning look moved my hands away, it was even worse now, before I felt like I had no choice but now I had to stop myself and keep exposing my undies to the girls. The girls made me get them drinks and snacks laughing at me as each time they wanted it with ice or with the crusts cut off.
After a while the girls started making me do things just to embarrass me, Kerry told me to go outside and make sure the gate was locked. “Please let me put on some more clothes I begged”
Kerry’s smile never disappeared “Ok then” she threw me my trainers. All the other girls burst out laughing. I swallowed my shame and made a run down the garden path covering my undies the best I could. The gate was locked and when I got back to the door they had locked me out.
“Please let me in” I begged fear welling in me.
“Nope you’ve been naughty and covered up this is you punishment to stand out there for five” said Kerry leaning out the window to laugh at me exposed to anyone walking past.
“Please its freezing” also it had started to rain lightly but I didn’t want to give the girls any more ammunition.
“Ok instead you can come in the back and use the dog door, and remember no covering.” laughed Kerry
I knew what the problem with this was, to get to the back I had to leave from the front gate and go down the street at the side of the house. I ran forcing myself not to cover, a car went past but before I knew it I was at the back door. I crouched down and was about to crawl through the dog door when I was interrupted.
“You’ve got to come in feet first” shouted someone from the other side followed by loads of laughter. I obeyed squeezing through the dog door legs first which isn’t an easy feat. Just as I get half my body through on of the girl’s jumps on my legs getting me stuck with my little undies on display on the inside.
“Maybe we should just strip you naked after all what do you think?”
“No please don’t we had a deal!” I begged panic rising in me again.
“I suppose” I felt a finger on the waistband of my underwear I was terrified but the close to imitate contact felt good which made me even more nervous.
“So perv did you enjoy seeing the girls in their bra and knickers?”
I didn’t reply. “answer me! Or else”
“Yes ok I did” I confessed knowing that if I tried to deny it they would only make it worse for me.
“Did you like Emily kissing you, showing her little boobs in that pink bra?”
I realised what Kerry was doing but I couldn’t help myself being turned on again by her words and the images from earlier.
“Oh maybe we should all get undressed for you, hmmm, right now I’ve just taken off my top would you like to see…” Kerry burst out laughing “oh dear you’ve been a bad boy again!”
“Here is your punishment” I felt the waistband of my undies lift up, I was terrified they was going to expose my boner but instead I felt an ice cube slide in. I screamed the freezing coldness against my penis was awful, soon my boner was killed and the ice melted giving me damp undies. The girls let me come all the way in laughing their heads off at me.
SDS
Stripping the Babysitter - 4 - Awful punishments
Thu Apr 26, 2012 6:45pm
Chapter 4 - Awful punishments
After about half an hour the girls started dancing to the music channel, they made me watch them. I know they did it on purpose pulling off provocative dance moves, especially Kerry bending over right in front of me and flashing me her cleavage. Someone tripped up Jane, making her flash me her panties briefly again as she stood back up. The girls noticed my excitement and made me stand up again.
“You have been very bad! You need to cool off and stop perving on us !!!” said Emily with a massive grin on her face.
“Ok now it’s chucking it down your punishment is to go stand in the rain until your boner goes down” said Kerry leading me to the front door again. It was humiliating but luckily didn’t take long for it to go down. Just as I was coming back to the door it opened I was hit by a full bucket of water to the undies. I had managed to keep them dry enough to not be see threw but now the white had turned practically transparent.
I covered up, I couldn’t stop myself, if I hadn’t they would have seen through my undies. They let me come in I was freezing and shivering. They had rooted through my bag and had binned a couple of pairs of boxers, all I had left was one pair of grey briefs.
“Ok now before you catch your death of cold take off them undies.”
I started at them in dread, unable to move or speak.
“Here” Kerry said throwing me a towel to cover up. “but you have to do it in here” reluctantly I removed my undies and dried myself. The girls grinned like chesser cats not taking their eyes away from me. Finally dried and naked they gave me my other pair of undies to wear. They made me turn around so I wasn’t facing them and then Kerry grabbed my towel and pulled it away from me leaving me naked saying it was punishment for covering earlier but don’t worry they’ll only see my bum. Totally humiliated I pulled my undies up my totally naked body as quick as I could. The girls where taunting and humiliating me saying nice bum, it was truly horrible.
“Well then so now you’ve been totally naked how do you feel”
“humiliated” I said turning back to them in my undies.
“Oh by the way I’ve got a nice shot of your bum here” the girls gathered around the camera to laugh.
“Oh that’s priceless” said one of the other girls with ginger hair.
“I know what we can do now” said the last girl who was quite chubby with short dark hair. “We can tell embarrassing stories to see if anyone’s been embarrassed worse then this”
“Like can you remember the time when poor little Emily was getting dressed and my brother walked in, all she was in was a pair of panties and her PJ top”
“Oh I get it” said Kerry grinning wildly at me. The girls had a quick hushed convocation. I knew it wasn’t going to be good what ever they were whispering about.
“Ye but that’s not as embarrassing as when we stole Kerry’s bikini top while she was sun bathing at the beach. Remember Kerry you had to chase us all the way up the beach covering you naked boobs. ” said Lisa the ginger girl.
Kerry laughed it off, I tried to not picture these stories in my head but I couldn’t help it.
“Remember the first time you wore a thong Lisa? You were showing us in the living room and my dad walked in when you had it lifted up showing you bum”
I was starting to blush again the girls were doing it on purpose I tried to ignore it but soon my excitement was showing again.
“Right that’s it you bad boy, you need to stop being such a perv or there is going to be trouble.” Kerry said while walking over to me. “So you like to here about Lisa’s thong well let me show you what it’s like.” I daren’t resist as she grabbed the back of my undies and gave me a painful wedgie.
“Don’t be so shy, we’ve all seen your bare bum anyway. No here’s your punishment, hands on head, stand up straight and we’re going to give you a good spanking until your boner goes down” Humiliated I tried to refuse
“Please this has gone too far” I pleaded
“Do it or we’ll all gang up on you strip you butt naked, tie you up and put you on webcam to everyone at school” said Kerry with a massive grin on her face. I had no doubt she would go through with it.
I accepted my fate putting my hands on my head as the girls took turns swatting my exposed bum from the wedgie. It hurt like mad I hoped it would be enough to quickly get rid of my boner but as it started to go down, Kerry and Lisa did paper, scissors, rock and suddenly Lisa swore. Lisa turned to face me and to my surprise slowly pulled her shorts down to the floor revealing her yellow cotton panties. I tried to stop it but before I knew it what was happening it was up again. The girls didn’t stop laughing, Lisa pulled her shorts up laughing off the embarrassment herself.
The smacking intensified, Kerry pulled my undies high up my red checks, I was almost in tears from the pain, I was so humiliated I would have done anything to stop it. “aww its going down again. Someone flash him a bra” said Kerry laughing, after a few more paper, scissors, rock games Emily lifted her top up exposing her pink push up bra again, I knew what was coming but couldn’t stop myself enjoying the image. They continued again, tears dripped down my eyes and I winced with every smack. The worst thing was Emily didn’t get redressed and so I couldn’t lose my boner. Finally though she did and after some hard smacks with a wooden spoon I was in real pain.
“aww don’t cry little perv I know what will cheer you “UP” ” laughed Kerry. After a few more games it landed on Lisa again, if only my boner had fully gone down I would have been spared this humiliation. Again Lisa pulled off her shorts but this time didn’t stop there, she then lifted her top revealing a matching yellow bra. Unlike Emily she hadn’t padded it but her natural cleavage was enough, the sight of her only in her panties and bra, red faced and embarrassed turned me on so much I couldn’t stop getting hard, however really unluckily for me the excitement was too much and the front of my undies had been clearly stained with Pre-cum.
SDS
Stripping the Babysitter - 5 - Naked Spanking
Thu Apr 26, 2012 6:47pm
Chapter 5 Naked Spanking
“Oh my god Look he’s cummed his undies.” Shouted Kerry excitedly pointing at my undies. “you know the rules, time to get naked”
“No please no” I said tears of humiliation and pain dripping down my face. “It’s only precum I haven’t done it properly please no!”
“Take them off now” Kerry replied with a hungry look in her eye.
I don’t know what I was thinking but I tried to make a break for it, I ended up tackled to the floor. They grabbed me turning me over so I was face up,
“Resist and the whole school and not just us will see you naked”
I froze, Kerry reached down and grabbed my undies. Without mercy she pulled them straight down my legs. The girls screamed laughing at my small penis as it came on display. It was down again but this somehow made it worse, they laughed and all I could do was cry. Lisa still wasn’t dressed and suddenly she came over to me her cleavage inches from my face. I couldn’t keep my eyes off her boobs clad only in a yellow bra, I’m sure she did it on purpose.
My boner shot straight back up to the girl’s great amusement. Lisa got dressed and Kerry made me stand up with my hands on my head and boner standing up in front. It was so humiliating; they threatened to spank me again if I tried to cover up so all I could do was stand there totally humiliated in front of them with my boner sticking up in the air in front of the five girls. Kerry ran upstairs and I could here the shower running after a few seconds, the remaining four girls got stared with wide grins at my naked humiliation. Jane stared the hardest and blushed almost as much as me, I was obviously the first boy she had seen naked and my boner furthered my humiliation.
Kerry returned and quickly snapped a picture before I could cover, for trying I got another large smack across the naked bum. I had managed to stop crying and before I knew what was happening I was led upstairs to the bathroom. “Ok girls are you ready to see a disappearing act!” said Kerry laughing. “I’ve herd that when it’s really cold boy’s willies shrivel up and get really small.”
I suddenly realised that the shower was running cold water. “No please don’t d…”
“Shut up slave, unless you want your butt naked boner picture on Facebook?”
I shut up quickly my face was red. Kerry pointed at my lack of boner and frowned, “That won’t do I want to see what happens if you start big and then we freeze it”
Kerry whispered something to Jane the youngest looking girl and eventually she nodded grinning. “It’s your lucky day perv, Jane’s going to strip for you.” I couldn’t believe it Jane pulled her arms out of her dresses strap and slowly lowed it exposing just the top of her bra. Then in one swift motion taking Jane totally by surprise Emily and the ginger girl had grabbed the dress pulling to straight down in one swift motion.
Jane had only been pretending to undress but had actually been tricked and in one swift motion her summer dress was pulled down her body to her feet. Her face went from a grin to one of shock and finally to white faced horror as she stood in front of me in her little Hanna Montana panties and white bra showing her small breasts and lack of cleavage. She screamed trying to fight them but they held her between them laughing, Jane was short and skinny with very pale skin and her innocent look made her humiliation all the more real. When they let her go she got dressed quickly tears running down her face, they then made me get in the freezing shower. My new excitement was met with laughter as the freezing water hit me.
“Oh my god his willy has gone from standing up to small to tiny !!!” shouted Kerry pointing at my nakedness.
SDS
Stripping the Babysitter - 6 - Dressed Like a Girl
Thu Apr 26, 2012 6:48pm
Chapter 6: dressed like a girl
They let me get out of the shower after my penis was small and shrunk from the cold. They quickly dried me and then took the towel leaving me butt naked. The girls found my predicament hilarious ordering me around again butt naked. When I came back into the living room with some drinks they had taken all the clothes out of my bag and they where no where to be seen.
The night was starting to get cold and I physically shivered from my nakedness. The girls were whispering which wasn’t a good sign. “Ok do you want to be naked all night?”
“No I said” a ray of hope breaking my bleakness.
Kerry came down stairs with some of her clothes. Suddenly I realised what she wanted me to do.
“I can’t wea…”
“Slave are you really going to say no?”
The girls burst into hysterics as they looked through different underwear for me to wear. In the end they settled for an old pair of pink Disney Princess panties with Cinderella on the front. Unlucky for me I was skinny and so they easily fitted on even though they had been Kerry’s when she was twelve although back then she had been chubby. I quickly put them on glad to have something to cover up. However my nightmare had only just begun the girls found me a matching bra and stuffed it to make it look like I had small tits. My hair had always been kind of long and curly but when the girls straightened it suddenly it looked like short girl hair. They put some make up on my laughing at me at every stage sat there in only a bra and knickers.
My body being skinny and my height fairly short all added up to me looking like a girl, it was horrible; they girls teased me saying I looked like a pretty girl. When they showed me the mirror I barely recognised myself, I really seemed to fit in with the 13 year olds around me. For the next hour the girls ordered me around loving every moment of my humiliation. As I walked back into the room the girls were staring at me with huge grins on their faces.
“we can’t decide what to do with you next, we was thinking of maybe making you model different kinds of underwear, maybe a thong? What do you think of that?”
I stood petrified, it was humiliating enough being in Disney knickers. The girls burst into hysterics. “Nah maybe we should just make you get naked again, I’m sure you bare bum wants another spanking” said Emily.
“Don’t be silly Ems he makes a lovely thirteen year old girl”
To my relief they left it at that but after about half an hour they declared it was time to get changed for bed and the girls disappeared upstairs. After a while they came back down in Pj’s varying from little shorts to a night dress.
The doorbell rang and I froze with fear.
“Oh that will be Clair, we’ve invited her to stay over with us”
Somehow a fresh new face to be totally humiliated to made me feel awful. I was terrified they was going to make me go to the door like this but instead they gave me a long T-shirt to use as a night gown and Kerrie told me to pretend I was her little cousin or else if I was found out I would be butt naked again.
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