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The Chaperone

by Phantom81

Copyright on this story text belongs at all times to the original author only, whether stated explicitly in the text or not. The original date of posting to the MMSA was: 02 Jun 2018


I was a mature 14 year old chaperone to 4 boys on a very big trip to a huge amusement park a few years ago. We were part of a large tour group, and the four boys I was in charge of were Evan, age 8, Matthew age 9, Bobby age 10, and Chris age 11. There were 6 groups, each consisting of 4 boys in various other age groups, and we all got to stay at a very nice hotel. We got a great package deal: 6 separate suites that had 2 bedrooms and two bathrooms. The suites had a small kitchen as well, and a very large living area with a 6 person Jacuzzi bath tub over to one side, with a view. Bus fare, hotel and amusement park tickets were all included. We got to spend 10 days there! It was fun, but trouble and 4 mischievous little boys were about to mix! It’s a good that 3 of the chaperones were Dads of some of the boys, and all the kids’ parents gave permission to use corporal punishment if and when deemed necessary. And we had the authority to spank on the bare bottom as well (is there really any other way to spank a naughty little boy?) The four in my group openly admitted to me in general conversation on the bus about the trip and permission slips, and that they get a spanking sometimes from their Dads, especially when they break the rules.


Oh, really? I said. That’s interesting! And it was. So next I asked them, How do your dads spank you when you break the rules? I was fishing for answers in a fun way. The answers were fun to hear!

My Dad spanks me on my naked bottom said Evan

Same here! replied Matthew. Both Bobby and Chris said they get spanked the same way as well.

Wow! That must hurt getting spanked on your naked butt! They all giggled a bit when I referred to their bottoms, as butt

Yeah, my dad makes me pull my pants and underpants all the way down to the floor when I get a spanking! Noted Bobby

And my Dad pulls mine down all the way and sometimes makes me step out of them! commented Chris.

If I don’t pull my pants and underpants down when he tells me to, he does it for me, and I get a swat on my butt even before the spanking starts! added Evan.


Well sometimes I get spanked naked! Remarked Matthew proudly.

Really? No way, dude! I never got spanked naked when I was your age! That must be really embarrassing Matthew! Why did he spank you naked? (The boys giggled at the word ’naked’!)

Because I was caught playing with matches in the backyard and nearly set a patch of grass on fire. And I was just wearing my shorts that day and NO UNDERPANTS! He said with a smile.
Well l can understand why he spanked you butt-naked then! I said jokingly. The boys also giggled at the word butt-naked. Did you have to do naked corner time too?


For how long?

About an hour

No way! The others remarked in disbelief

Yeah, I got to see him naked when I came over to play! said Bobby with a big grin on his face

And he touched my butt too when I was still naked in the corner! It was fun!

And it was warm!

I’m sure it was, Bobby. Was it fun to touch his butt?

Yes! It was soft too! He laughed at his own remark.


I just rolled my eyes and said. You two are goofballs! The other boys admitted that they’ve had to do naked corner time after a spanking as well, but for only about 15 minutes. Chris even admitted to getting a boner once before a spanking, and he thought that was kind of fun. And of course the others giggled at boner too. Matthew commented: Yeah, but mine is bigger! They apparently had compared erection sizes, but I didn’t inquire when or where.

Have you guys ever gotten a spanking when taking a bath? I asked.

Bobby and me have before when I was at his house for a sleepover remarked Evan.

Yeah, my Dad spanked us both for getting water on the floor; he spanked our wet butts with a paddle, and then washed us up from head to toe!

It really stung, too! remarked Evan

I bet your naked little fannies were sore for a while, huh?

What are fannies? they all asked

A Fanny is just another word for butt’ That got a big laugh! And they started teasing each other by playfully smacking each their friends rear ends, and repeating the word Fanny for about 10 minutes. I even gave them each a few playful smacks on their clothed bottoms, and they seem to enjoy it. All done in jest and just part of some horseplay.


Matthew spoke up and said, Hey John, you would spank us on our naked butts if we were bad? He was a little concerned, but inquisitive.

Only if you boys were really naughty! I said with a wink and smile

Would you pull our pants and underpants down, too? Bobby asked

I sure would! In a heartbeat!

Then you’d see our willies! Evan replied and immediately covered the front of his pants.

Oh you guys are so silly!

Well, how else would I give you guys a spanking? Spankings for naughty little boys are supposed to be on the bare fanny! Said in ½ jest. I had the biggest smile when I told them that!

What’s bare mean? they inquired


Does it mean naked?

It sure does, you silly goose! I noticed that each one of them was fingering himself through the front of the shorts upon hearing the explanation.


Would you ever spank us naked?

It all depends, guys If you guys did something really naughty and told a bunch of fibs when taking a bath, then yeah, I would spank you guys naked, but you all don’t have to worry about such things.

Would you wash our naked sore bottoms, too?

I don’t see why not!

No way, that would sting! I hope you don’t spank me naked! commented Bobby.

Chris added: I wouldn’t care; I might get a boner again!

Yeah, you just might, Chris, and it would be a normal reaction if you did I could tell Evan and Bobby were a bit puzzled by the word boner, even though they laughed at hearing the word earlier.

Hey, John, what’s a boner? I went on to explain it the best I could and how a boy can get one, and their eyes lit up a bit. The two little boys confided in me that their penises had gotten stiff in the past; they just didn’t know it was called a boner. I mentioned that the proper term, was erection, but if they wanted to call it a boner, that was cool.

Wow, that’s sounds neat!

It is! said Matthew. Look, I got one now! he said as he pulled it out a little bit through the loose edge of his shorts. Me too! Said Chris, while he did the same. The two continued to finger themselves and it was very obvious they both enjoyed playing with their little boy boners. I could even see part of their hairless scrotums.
Guys, stop playing with yourselves! Now’s not place or the time.

Matthew looked at their crotches, and proclaimed, once again that his was bigger.
That’s enough, all of you! I should spank you guys for doing this!

I dare you! said Bobby

Oh, now that’s a dare you shouldn’t make, young man!

Why not?

Because if I spanked you, it would have to be on the bare bottom!

Go ahead then, see if I care! The little boy pushed.

Do you really want me to pull your pants and underpants down, right here on the bus, in front of all these other boys, and spank you?

I don’t care! He was really pushing it now.

It’s gonna really hurt, and you will be crying like a baby!

Bobby paused before he spoke this time, really giving it some thought to his answer. Um, that’s OK; you don’t have to spank me


Too late, buddy; however I will give you a practice spanking, just to let you see what a spanking from me will be like. As a matter of fact, when we pull into the restaurant to eat, I’ll make an excuse to stay on the bus with you guys, and then I will spank your naked bottom. How does that sound? And that’s exactly what took place. I pulled the naughty little 10 year old boy’s pants and underpants down(he had a very cute, round, white, firm little butt!), after making sure everyone was in the eatery and after I locked the bus so no one would interrupt us. I told him not to kick or move around on my lap, not to reach back and try to protect his little fanny, and to only stand back up and pull his pants up, when I told him to. He agreed. We went to the big long seat in the back of the bus, and I yanked his short down to his feet. I then took his briefs down and was 3 inches from an incredible looking and very smooth naked bottom! I then put him over my lap, and gave him 10 good smacks! After I finished, I rested my hand on his cute butt which was somewhat red. Who wants to give Bobby a few smacks on his nude bottom? ME! they all answered in unison. And of course I let each boy give Bobby 2 smacks. Who wants to feel his butt to see if it’s still warm? They all did! I could tell Bobby liked it just as much as his friends did, because each of them had boners! And Bobby’s was throbbing with joy! He even reached under himself, and began to rub it a bit! After about 5 minutes, I had him stand up, pulled his pants up, and we all went to lunch.


To be continued....

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