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The following story is fiction about spanking bets.  The story contains scenes of spanking, strapping, paddling and tawsing.  If these subjects are offensive, uninteresting or if you are a minor (i.e., child) please leave now.  This is the seventh in the series and you can find the first at The Spanko and the Author They are best read in order as addition background is developed in each.

This work is copyright by the author and commercial use is prohibited without permission.  Personal/private copies are permitted only if complete including the copyright notice.

The author would appreciate your comments – pro and con, including constructive criticism, and suggestions.  Please take a moment to email.

You may change the following names in the story to enhance your reading pleasure. 

The young top spanko
Golf player #1
Golf player #2
Golf player #3
Golf player #4
(Names must be alphabetical characters without spaces.)  

The Spanko and the Foursome


They were remarkably similar and they played together every week weather permitting.  Each was the CEO in his own small company and extremely competitive.  At teeoff they would each put a C-note into an envelope which I, one of their caddies, would hold for the winner of the round.  The risk was actually much smaller than it seems for I tracked the results and they each won just about 25 per cent of the time.  They also tipped generously.  Greg and I were their favorite caddies.

It was after the twentieth game of the season and we thanked them for the generous tips and handled the prize envelope to the winner.  “I wonder why you bother with this?  You are so evenly matched that the worst anyone has done was four and the best six games and you don’t really care about the money.”

They were dumb struck.  I had thrown a novel question at them that stock answers wouldn’t help.  Then I threw the kicker at them.  “Why not make it a novel prize for the high scorer – a spanking.  A spanking watched by the rest of you.”

That caught their attention for none of them rejected the idea immediately.  Then Mr. Adkins asked “Who would give the spanking?”

“I would so no one gets to dislike another.  I’m experienced spanking men so I would be consistent and thus fair.”© YLeeCoyote

“What kind of spanking?” asked Mr. Birckhead.

“Perhaps OTK with hand, brush or paddle.  Perhaps bent over a table with a strap or paddle.  Other possibilities exist.  Certainly bare bottom.  Could be a fixed way or drawn from a hat.  You can think and talk about and decide next week.”

I did not lack for jerk off fantasies that next week.  I thought about spanking each of the four men in many possible ways.

“Don’t get hyped up that they will agree, Edger.” cautioned Greg as he tried to prepare me for a continuation of the status quo as he was concerned and he did not want me to crash.  He had a good point and I tried to remember that every night.

On Wednesday, I sent each of the four a link to a survey I set up to get an idea what they wanted to do and what implements I might need to bring.  The responses seem to be pro but I would not know for sure until we met for the next round on the links.

I was absolutely elated when teeoff time came and they told me they were going for my spanking idea.  This time rather than cash they each put in a spanking scenario into the envelope and the ‘winner’ would draw one out.  I could hardly concentrate on the game rather than looking at the four manly butts as we went around the course wondering which would be my target.

Then after some four long hours the round was over and Mr. Lamson was the ‘winner’ by at least three strokes.  He obviously had a very bad day.  We retired to the far side of the maintenance yard where things would be a bit private for the grounds staff worked mostly at night.

I folded each of the four proposals (without reading them) and put them in the hat Greg was holding.  Mr. Lamson selected one and I read it aloud.  “Five cuts on the bare with the belt for a one stroke loss.  Ten cuts for more.”  I was glad that I wore my heavy Garrison Belt this day as it was perfect for strapping a deserving tail.

I must give Mr. Lamson full points for his no nonsense behavior.  He quickly moved to the pile of supplies, dropped his pants and undies and leaned over.  It was a beautiful sight.  I have to confess my jeans were tenting.

I pulled my belt out, folded it and started to deliver the ‘prize’.  I swung the belt and it was a most delightful sound it made on contact.  Immediately a stripe formed.  I repeated the action four times for the first stroke prize.  Mr. Lamson’s bottom turned a lovely red.  Impressively, he had taken them well and in complete silence.

“Halfway.” I announced although all knew.

Then it was time for the second set of five.  All as before except now Mr. Lamson’s butt was bright red like a clown’s nose.  I had great fun.  As I put my belt back on, Mr. Lamson redressed.  I noticed that the other three gentlemen had bulging crotches.  I was sure that was a good sign for more action next week.

They went for their usual libations and probably stood at the bar rather than sitting at a table.  Greg and I got bigger than usual tips.  It’s great having such extra fun and being paid for it.

Again, on Wednesday I did another survey.  I went into a bit more detail in case I might need to bring an implement.  First, of course, I checked if they wanted to continue with spanking and, second, I asked about implements.  Happily the former was a GO and I packed both a frat type paddle and flip-flop to use as a small rubber paddle.

This time it was Mr. Kimley who won the spanking.  The chit he drew was great from my POV although he did not like it.  Of course, he could not back down because of peer pressure.  In the maintenance area we found a bench which was perfect for the task at hand.

I sat at the end of the bench and Mr. Kimley found his place.  It was a great pleasure opening his pants and yanking them down immediately followed by his boxers.  He lay on my lap with his top supported by the bench.  It was a lovely sight to behold.

The chit had been brief with just the three letters – OTK – so it was up to me for the details.  I got a grip on his waist and began the spanking with my hand.  That is not really effective with a man but nice to start with.  Then I got serious and signaled Greg to give me the flip-flop.  It was old and flexible and without the strap and made an excellent paddle

I tightened my grip and started the real spanking.  Mr. Kimley reacted immediately to the greatly increased force and corresponding increased pain level.  I would have loved to have made him cry but that could have easily spoiled the setup so I restrained myself to about a score of spanks.  His well-roasted bottom glowed like a couple of beacons and I’m sure he felt the heat and pain for a long time.  It was a most exhilarating experience for me.

By the time I got home this spanking was a fond memory that I would treasure.  I had plenty of stuff to jerk off too now.  I was hoping that I would get to spank the other two gentlemen.  If that was to be I would only learn in the fullness of time.

Spanking round three got me an all new combination of Mr. Adkins and the fraternity paddle.  The chit specified four pops per stroke with a limit of ten.  When I read it aloud, Mr. Adkins turned ghostly white and I think he wanted to run far and fast.  Of course, he couldn’t do that without losing much face (as the Japanese say).

Fortunately he lost only by one stroke so I was limited to four pops which, I hoped, was less scary for him.  We went to the maintenance area but I couldn’t say anything to try to relieve his anxiety.  Once there it was pants and undies down then bending over and grabbing shins like a frat pledge.

I swung the frat paddle as easy as I dared hoping that the other would not realize I was going easy on Mr. Adkins.  The paddle connected with a THUD.  It was instantly followed by a loud yelp of pain.  Fortunately he did not completely embarrass himself as he retained his position.

After almost a minute I said “Time for the second pop.” and placed the paddle on his butt briefly before swinging it.  The response was the same and his tail was turning red.  Pops three and four were not any different but when I said get up he immediately started to rub.

Greg and I collected our money and left the men to make sure Mr. Adkins was OK as they visited the bar.

My regular Wednesday check got an OK again and I was hoping that Mr. Birckhead would be my target.  As it turned out that he was the winner.  I couldn’t be absolutely certain about it but I think he missed his last putt intentionally.  That would make sense if he wanted to bond closer with his friends.

When I read the chit he selected I noticed that it was an off-white unlike the others.  It was different calling for ‘six-of-the-best’ with a tawse.  I don’t have one of those but Mr. Birckhead had his grandfather’s and said that his father often talked of feeling it.  I’m sure that he wondered about it.  Well, now he’ll find out.

Mr. Birckhead got into position faster than I did after taking a few practice shots the tawse to get the feel of the thing.  I gave him a shot and it was clear that he felt it but stayed in position.  It left a nice stripe which was turning red very quickly.  It did not take long to get to six which left his rump bright red.

When he got up he did some rubbing and said “That sure stings.”  Greg and I got our cash and headed home while the foursome went off to the nineteenth hole.

“Edgar that was really a great idea but, alas, the season is over.  You think you see any of their butts before spring?”

“I sure hope so while making them red.” I replied “They all know my email…”

Read about "The Spanko and the CEO"

© Copyright A.I.L. June 11, 2022

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Last updated:  September 15, 2023