Jake’s Report© Y Lee Coyote

I’ve had good and bad, nice and nasty babysitters over the years but Teddy is absolutely the best as far as I am concerned although he is totally incompetent.  Oscar used to babysit him when he was younger and sometimes I went along.  That happened with others also but Teddy was different for he was an immature spoiled brat and Oscar spanked him frequently.

Those were the best of times because I would ‘help’ my big brother discipline the ‘baby’.  Yeah, I was younger but I loved to do it and Teddy could not do anything about it expect howl when I hit him with all my might using a flip-flop or his mother’s heavy wide backed hairbrush as Oscar held him in position.  I had to search on the web to find this appropriate expression to convey my feelings – it warmed the cockles of my heart.

Well, we all grow up or actually we get older and Teddy started to babysit.  I had been asking for a male sitter for the girls always want to take my pants off and Mom (bless her) spotted his ad in the supermarket.  So, I was his first client.

Along with Oscar I wondered if he had grown up but it really did not matter because I could mange quite well alone for several hours but The Law required I have a sitter.  Teddy hardly looked to be fourteen and I couldn’t help to wonder if he had matured down below.  When I saw him naked getting off Oscar’s lap years ago he was very tiny.  Now his snug jeans did not indicate anymore.

We got along fine for diner and video games.  What I found was that I was leading and he was following the same way that he did when Oscar was sitting him.  That certainly made him a great baby sitter for he did not give orders.

When I went to get ready for bed I told him, jokingly, to do his homework and that bent him out of shape. I regularly say that to Oscar and he does it because he was going to anyway.  When I got back, he was surfing and I just recorded him for a while and then pounced for he was looking at naughty stuff.

It was easy and quick to convince him that he was better off if I spanked him rather than his dad.  I was overjoyed!  It was like leading a lamb to slaughter when I took him into the family room and told him to strip.  I felt like I was Oscar and babysitting him.  He even looked like he did back them with a teeny thingy.  I gave him a good hard spanking starting with my hand and then breaking him using a flip-flop.

To drive the point home, I made him do corner time.  I sent him an email in the morning showing him in the corner with an apple butt and telling him that he was the best babysitter ever and I hoped to see him again very soon.  I’m sure he does not want anyone to see the corner pics and won’t try to avoid me when my mom calls him to sit next week.

Teddy showed up on time for his second gig but he did not look very happy.  I, of course, was delighted and had high hopes of getting him naked and over my lap again.  I guess it could be argued that he was old enough to strap but that would not be as much fun for me as giving him a traditional OTK spanking.  Oscar had explained to me that treating him as a little boy would make him even more docile.

Teddy complained that I did not delete the video as promised but threaten him with it.  I carefully explained that the corner images were taken after the promise and thus not included.  Using the earlier video would have been dishonest.

I waited until after we had eaten and played video games before telling Teddy that he had insulted me by calling me dishonest.  He was surprised and made stupid retorts.  That was just fine because I said the penalty for such disrespect was a proper spanking.

I came down on him hard so that his submissiveness took over and he was willing to accept his punishment.  I stripped him as he stood there fearful of me.  When he was in his birthday suit I reminded him how he was just a naughty little boy with a bald little thingy.

Then came the best part.  Rather then sit on the couch I sat on a plain study kitchen chair and got him over my lap.  I kept a good grip on his waist and initially spanked him hard with my hand.  I then switched to my folded and shortened belt which quickly reduced him to a blubbering mess.

I, on the other hand, was simply elated.  I parked him in the bathroom corner while I got ready for bed.  I made sure that he could drool over my small but definitely present bush and larger cock.  I got into my designer boxer-briefs and helped him back into his generic TW’s.  Then it was bed for me and homework time for him.

Of course, I told my parents that he was a great sitter and to keep hiring him.

Oscar’s Report

I was delighted when my kid brother, Jake, told me of his experiences with Teddy as his babysitter.  It really made me proud of him.  Also, it appears that although Teddy has gotten older he is still just an immature naughty brat.  Personally, I think that he needs to have a roasted bottom all the time.

Let me tell you about last Saturday.  Our ‘rents wanted to go play while I had a birthday party to go to so they hired Teddy again at the urging of Jake.  It was an interesting evening as Jake explained to me when we got to talk.  The details don’t really matter except for one.  Jake had gone to pee leaving Teddy alone and when he returned saw that Teddy had moved a game piece on the board.  The precise word for that is CHEATING.

Jake immediately called Teddy on that and the perp quickly confessed.  Need I say that cheating is a spankable offence and that is what Teddy got.  Jake thought that some variety was called for so he got the hairbrush Mom liked (well, actually she still likes) to use on us.

He stripped the naughty brat and took him over his lap.  He had learnt that he did not need the couch for support so just sat on a kitchen chair and was careful to leg lock Teddy in place along with holding a wrist behind his back.  “I first had the pleasure of turning his tail red with my hand.” he told me with a big grin and continued “Then I switched to using the hairbrush hard and fast and Teddy quickly showed what a bawling baby he was.”

Jake watched some TV while Teddy did some corner time.  As Jake was scheduled to go hiking with his pack in the morning, he sacked out early.  It just another indication of his maturity.

My evening did not go exactly as planned at Tyler’s seventeenth birthday party.  A couple of the older guys present had brought some weed and beer.  It quickly got loud and a neighbor came and complained.  Tyler could not get it under control.  I figured that the fuzz would soon show up, so I bailed and went home.  That’s not how I want to meet those nice policemen.

Jake was sound asleep but Teddy was in my room reading my exotic literature.  Well, I immediately put a stop to that and dragged the miserable rat downstairs.  I did not even let him pull his pants up to cover his tiny peepee.

When I sat down and dragged him over my lap I saw that he had been spanked by Jake again.  What an ass he was.  I gave him a few hard spanks and he yelled.  Since I did not want to have him wake Jake I stuffed his TWs into his mouth to muffle his howls.

That also indicated that stronger measures were called for and I draped him over the end of the couch.  I pulled my nice heavy garrison belt from my jeans and gave him what he deserved.  He was bawling after five cuts but he got a dozen in the vain hope that he would mend his ways.

When he stopped crying, I told him to wash his face, paid him and sent him home.  I left a note for the folks and went to bed.