Stripping My Babysitter Naked – Part Four

Embarrassing Story Series about stripping a babysitter.

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Stripping My Babysitter Naked Story Series

Part 1:

Part 2:

Part 3:

Part 4:

Part 5:

Part 6:


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.

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