I was fourteen and off to my first babysitting gig with Jake.  I was quite excited.  Jake was almost twelve.  We had known each other for several years because his four-year older brother Oscar had babysat me a lot and occasionally Jake had tagged along because he needed to be watched also.© Y Lee Coyote

As I walked over to his house I could not help thinking if I would have reason to spank him like when Oscar had sat me.  That really wasn’t what I should have been thinking about but I was too young to be professional about it.

Jake was happy to see me and his parents went off to do their thing.  We managed to play some video games and have dinner without any problems and I was sure that he would get to bed as he was supposed to.

I was not happy about his favorite topic of conversation as the principal subject was my butt.  Apparently high among his most wonderful times were when Oscar spanked me and he got a few swats in of his own on my unprotected butt.  Yes, that really happened a few times and spanking an older boy is most exciting.  Of course, he was not doing it on his own but while I was being held over his brother’s lap.  He had used his hand, of course, every time but he loved it even more when he swung the flip-flop with all his might.  He made a big point that he loved hearing me yell from that.

I tried to shrug it off as it made me uncomfortable but he was very persistent happily recalling his mean whacks.

He surprised me when it was almost his bedtime by telling me he was going to shower and get ready for bed and that it was time for me to get to my homework.  “I’ll decide that, Jake.” I rebuked him.  “I‘m the baby sitter – not you – and I’m in charge.”

“That’s what I always tell Oscar and he does it because that what he needs to do.” he countered very smoothly.

“Get ready for bed before I spank you, Jake.” I snapped at him.  He just laughed and ran off.  Of course, he was right about it being what I needed to do so I dug out my work and sprawled over the table.

Now I should have kept to the straight and narrow and worked on my assignments but I was weak and both the email and message icons were yelling for attention.  That I could not ignore them would turn out to be my undoing.

As I tended to these most pressing (non-school) items, Jake had finished and had snuck up behind me with his phone on record.  Some of the stuff was not for babies like him.  After a while he announced his presence.

“You are a very naughty boy, Teddy.  You’re just wasting time with all that junk rather than doing your school work.  I’ll bet your ‘rents will tan your hide really proper when they find out.”  He finished up with a hardy laugh.

When I turned I saw he was recording it all and just wearing a snazzy pair of designer boxer briefs sporting an ample bulge and a great big grin.  It was obvious he had a plan and he was certain that it was working.

“I agree that a spanking is in order like you said earlier but it is you who have been the deserving naughty boy not me.”  Even though his voice was still high pitched, there was a very menacing tone to it.  This became even more evident as he continued.  “Well, I’ll give you the choice.  I’ll send this video (already safe in the cloud) to your dad and you’ll get spanked by him or get spanked here and now by me?”

It was positively chilling for he was terribly right.

“That’s not very nice of you, Jake.” I sighed.

“True but those are the options.  Get it from your big strong dad or little me.  And who know what else your angry dad might do?” he taunted.  He surely knew he had the upper hand and that I was trapped.  Dad would be furious and, well, use the strap long and hard.  I took the cowards way and caved.  “OK, Jake, that video stays secret and you spank me.”

“I’m delighted you saw the light, Teddy.”  He led me into the family room.  Once there came the order: “Strip to your birthday suit like when Oscar spanked you.”

He was sitting on the couch and watching intently.  He looked me over and his grin got bigger if that was possible.  “I see that you still the little bald boy with a teeny little peepee.  Over my lap, please.”  That although true hurt and I quickly lay over his lap.  At least my little thingy was not on show any more.

He adjusted my position so my torso was supported by the couch and put a leg over mine.  Jake then commenced spanking me with his hand.  “You’re still the naughty little boy that you were when Oscar sat you.” he said as he spanked.  “I loved spanking you then and it is even better now.”  He spanked hard but nowhere as hard as dad did. “You’re turning a nice pink, boy.”  Happily I was able to resist crying.

“That was the warm up, boy.  Now we get serious.”  The next and subsequent spanks were a lot more painful.  I quickly learnt what changed when he explained “I see that the flip-flop makes a far more proper impression on you.”

Actually he heard that for I started to howl with the first spank from the flip-flop.  In short order I was bawling like the baby he said I was.  I must shamefully admit he broke me easily.  I stood in the corner with my hands on my head sobbing until he told, er, ordered me to dress and get to my homework and he went to bed.

I did as he ordered.  This did not bode well for my babysitting career.

When I left I decided that I would not sit for him again but an email in the morning from Jake said that he told his parents that I was his favorite sitter and he was looking forward to the next time.  It came with a picture of me in the corner with a bright red butt.  I was trapped.