I have just come across this site and thought I would share a story. Based on the truth but enhanced.
The door bell rang. I opened it and my friend Sam entered.
We were both 11 years old and had know each other for four years. We spent alot of time together at school, over the weekends and during holiday time. We played computer games, watched videos, played football, wrestled, gave each other wedgies and grabbed each others nuts.
Our favourite past time however was dares.
Sam was around and we had one more week of school left before the Christmas holidays and the weather had turned cold with snow and a biting easterly wind.
As we played on the computer I said to Sam, 'I dare you to wear shorts to school all next week.'
Sam replied, 'What in this weather and what for?'
'Yes, if you wear shorts all next week you can get me to do whatever to want next Saturday.'
'You want me to do the usual dare for anything I like.' We had done this dare before of wearing shorts to school, but never this cold. The usual dare being you had to wear the shortest school shorts you had and to keep your socks down by your ankles - so exposing the as much leg as possible.
Sam agreed to do the dare.
Monday morning came around, the wind was really cold and the frost covered the ground thickly. I wqs well wrapped up as I walked to Sam's house. I knocked on the door, Sam answered it, dressed in his shorts. He was going to do the dare.
'You sure you want to do this, it is freezing?'
'The dare was shorts for a week for anything I wanted?'
'Yes, that's right.'
'Ok, I'll do it.'
For the rest of the week Sam wore short shorts to school. The weather was very cold, he was the only boy in shorts in the school and was stared at as we to and back from school each day.
Finaly the week finished and as we got back to Sam's house he said,'See you tomorrow for payment. Come over at 10 and wear your school uniform with your school shorts.'
'OK.' I replied wondering what he had in mind. Saturday, the holidays and wearing school uniform, winter and wearing shorts perhaps we were going to town ad I was going to be humiliated. But I was wrong.
Saturday arrived, I went to Sam's house dressed as instructed. Sam opened the door and led me to the back lounge in his house. There their were about a dozen boys from our school, casually dressed. A large well padded armchair was in the middle of the room. Sam told me sit in it.
'The agreement for wearing shorts all last week was that I could do or get you to do anything I wanted.'
'Hmm, yes.' I replied, wondering what on earth he had planned. I was etting worried as here I was amongst a dozen boys dressed in school uniform wearing shorts.
'The payment for the dare is you take three stokes fromeach person here with his.' he held up a cane with curved handle.
'That's 36 stokes, no way, you're joking.'
'I am do, that's the deal.'
'You trying to get out of the bet.' Jack, one of the boys in the room, which started off a chorus of chicken and you can't but the penalty.
I did not want to loose any of the street cred I had. Whatever was about to happen was not quite as bad as loosing face amongst this lot.
'Ok, where do you want me.' I stammered.
'One more thing.' said Sam. 'The first half will be over your shorts, the second half over your bare butt.'
I had little choice by now.
'Lie over the arm of the chair and grab the other arm with your hand, place your feet on the floor. I did as I was told. Some of the boys got some rope and tied my wrists took the rope under the chair and the tied my ankles. I was firmly held in place, my backside felt very exposed.
'Go you ready.' I nodded 'Let's begin.'
The first boy took the cane found his position and in a wide arc brought it down on to my backside. I had been spanked before with various implements but even though the cane was being wield by an eleven year old nothing had prepared me for the pain. It seem to shoot throughout my body. I arched my back but was held tightly by the rope. As the pain reached a climax the second stoke descended.
I was starting to cry as the third stoke came down and I still had over thirty to go.
The pain was intense as the three welds on my back side throbbed. There was a few seconds pause as the cane was past on to the next boy and the process started again.
I had not exprienced such pain before. Finally the fist eighteen were soundely delivered. Tears were streaming down my face, I had almost lost my voice from the screams - why did not anyone come and stop this.
'OK, take his shorts and pants off.' I heard Sam say, this was only half way and now my only slight protection was going. I felt some ones hands reach under me and fiddle with the fly and button. Once the had released them they eased them over my aching backside and down over my thighs to my knees.
'WEDGIE TIME.' Some one shouted. Three or four hands grabbed the waistband of my boxers and hiked them up my crack. I shouted for them to stop, a wedgie was not part of the deal - as if another eighteen stokes of the cane was.
Soon the fabric was popping as the seams finally gave up. They got the ripped boxers up my back, taking my shirt with it. I felt very exposed, my flaming red buttocks against my white thighs and back.
'Wow, that must have hurt alot.' Some one said as the boys inspected the damage.
'Ok, your next eighteen.' The next boy took the cane, lightly tapped my leftcheek then the right, the pain started again even from these light taps.
He took a step back and brought the cane down on my exposed, bruised flesh.
'AWWWWWWWWWWWWWWWWWWWWWW.' I cried out as the intense fire started again.
Again and again and again the cane came down after the first twenty five stokes the wind was knocked out of me, I could bearly get a whimper out, the intense pain had changed to a dull ache that was not really registering.
'OK, last one.' Sam took a step back and brought the cane down right across my thighs below where my shorts would be.
The intense pain started again as unbruised flesh was hit. I did not care it was all over.
The ropes were released, I was helped up and my hands went round to my damaged backside.
'Have a cold shower.' Sam offered, I accepted.
The coldness took some of the pain away but my backside was on fire. I got dressed minus my ripped boxers from the wedgie I had received.
I walked home trying not to let the material of my shorts touch to much of my aching cheeks. The chill wind whistled up my leg holes and did some good in soothing my aching buttocks.
Me and Sam continued to do dares but I always made sure what the payment would be.