The following story is fiction about a teen and boy.  The story contains scenes of spanking and jo sex.  If these subjects are offensive, uninteresting or if you are a minor (i.e., child) please leave now.

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Click to have ​Metric units​ (​American/English units​) used in the story.

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Summer Setback
Vacation Disaster

By

YLeeCoyote@juno.com

It was not the best planned vacation but the alternative was to stay with my aunt, uncle and their three evil monsters who masquerade as my cousins in the middle of nowhere.  Even though I'll be fifteen in just eight months, I opted for going with the 'rents to this resort.  It is a fancy hotel with a pool and near a beach good for swimming, fishing and boating.  Dad promised that we would have some quality time together although I'm not sure that I really wanted that.  Whatever.

After just two days it was clear that there really was not much to do except the ocean.  There weren't any other boys who were my age with whom I could play as it was the off-season.  The older guys didn't even want to acknowledge my existence and I wasn't interested in the babies under twelve.  Things changed at our second dinner here.  Instead of eating alone (just the three of us) we ate with a couple that my folks had gotten friendly with and their son, Mike.  Mike was only eleven although, I will admit, did not act like a baby.  Our respective parents decided – without any consultation with us – that I was to watch over Mike the next day while they went and did adult stuff like golf.  What it boiled down to was that I was to be an unpaid babysitter.  I objected, how shall I put this, strenuously and, now in retrospect, less than politely.

Dad was not happy with me.  Well, there are other options he explained.  Sure there were.  Confined to the hotel room.  Have a babysitter (shared with Mike).  Be a caddy (unpaid!).  "How come I can be a babysitter but can't be alone?" I demanded. "It's very simple, Samuel," explained Dad, "if you're watching Mike then you won't go wild like you might if you were on your own.  So either you watch Mike or one of the other options I mentioned."

Mike managed to voice his opinion that he would be quite happy to stay alone in the hotel and read.  "I've got several books on my e-reader.  Also there is the garden to read in and the pool to swim in." he insisted.

"It's not fair." I shouted so everyone in the dinning room turned and looked at me.  "I'll watch Mike but he has to listen to me.  And I want to go to the beach."© YLeeCoyote

Mike's dad chimed in.  "Mike, it would be good for you to get out.  You can read on the plane, at night and back home."

Mike gave a resigned "Yes, Sir." like an obedient little sissy boy.

Our fates were set and now interlocked.  I had no idea of how interlocked that would turn out to be.

* * * * * * * * * *

The next morning at breakfast we were all together again and then the 'rents realized that they were late and dashed off leaving me with Mike.  We finished breakfast and I told him I would collect him from his room in fifteen minutes and added: "You better be ready or you'll get spanked."  My folks had stopped spanking me years ago but I thought that Mike was young enough to spank.  Besides I was sure that it would be fun – unlike being spanked.

Well, he was not ready when I got there.  He was getting into a kid's outfit of a tacky T-shirt and short shorts over his Batman tightie-whites.  I, like a proper, self-respecting, grown up teen, had a cool name-brand shirt and neat board shorts.  The usual extras were in my pack.

We got into an argument right away.  I reminded him that I was THE ONE IN CHARGE since I was the babysitter and he was the baby.  And that this babysitter believed in spanking naughty, troublesome, difficult babies.  This led to hot, loud words.  "You're just a little boy under those fancy clothes.  Dressed up to look like a grown up teenage guy and you're just a bully.  I'll bet that you're flatter than a girl between your legs and still searching for your first pubic hair." he declared.

"How the fuck do you know?" I snapped back at him angrily.  That was a big mistake for I was proving him right.

"It is simple, Sam.  Your shorts are flat there.  (He pointed at my crotch.)  Yesterday, your tight jeans were just as flat without a hint of package."  He laughed.  "And you just admitted it.  You don't even have pubes yet."

"OF COURSE I DO!" I lied defensively, shouting.

"Bet you don't.  Winner is in charge for the day." he challenged me.

"DEAL!  And I'm in charge." I said angrily forgetting that I did not have even a single pube.

"Prove your right to be in charge.  I say you're just a little, hairless boy with just a little pricklet."

"Do as I say or I'll spank you, Mike." I threatened.

"I won't let you, boy." he said putting his face to mine, "Unless you prove your right to be in charge."  He was three years younger but just ​a couple of inches​ (​five cm​) shorter and now was in my face.  What happed to the timid, bookish boy who meekly said 'Yes, Sir' to his dad?  "You're just a hairless, little boy who needs a magnifying glass to find his tiny pee-pee, Sammy." he taunted me again.

We glared at each other and he said: "SHOW ME or agree I'm in charge."

I did not believe he had anything.  He wasn't even twelve and I was almost fifteen.  He did not wait any longer but acted like lightning by grabbing my shorts.  In a flash he yanked them down to the floor.  He looked and laughed and then dropped his shorts.  I was shocked.  He already had a few hairs and his penis was at least as big as mine when soft.  He was not satisfied.  "No hair that I can see, Little Baby Sammy.  Where do you hide those pubes that you said you had?"  I was blushing.  "Does your thing even get hard?" he asked grabbing my dick.  I could not help getting hard and he also was pulling on his own.  He pulled us together and it was clear that he had ​three-quarters of an inch​ (​two cm​) longer thing when hard.  I was red all over.

"Well, then it is settled.  I'M IN CHARGE, Sammy.  I got pubes and you don't and my cock is bigger than your little boy's pee-pee."

"NO!" I retorted.  I was not going to let a kid take over even if he had a few hairs and slightly longer prick.

We were just a foot from his bed.  He yanked up his shorts and stepped back.  He gave a mighty yank and I fell over his left thigh.  Before I could recover, he put a hand on my back and his right leg over my legs.  I tried to get up but he had me trapped.  "First you lied and now you're trying to welsh on the bet.  You are a very NAUGHTY LITTLE BOY and you are getting spanked."  He managed to grab a wrist and pushed it up my back making it impossible to get up.  Then he started to spank me with his hand.  I howled and yelled but he kept at it.  It hurt.  Dad never spanked me this hard and it fucken hurt.  Over and over his hand hit my increasingly tender butt and soon I lost control and started to sob.  He continued to spank me until I was really crying.  Damn, he was strong and I had though that he was just a soft bookworm.

"Who's in charge, Samuel?" he demanded between spanks.  I did not answer until the third time when I surrendered hoping to stop the pain.

"You're in charge." I blurted out between sobs.  He made me repeat it several times.

He let me up and took me into the bathroom.  He helped me blow my nose after which he washed my face.  I couldn't believe that all this was happening to me.  Although I was almost fifteen and I was feeling like nine and my ass was ablaze.  Back in the bedroom Mike made me dress in his clothes – that nondescript T-shirt, tightie-whites with Batman on the seat and Robin on the crotch and his short shorts which were very tight on me.  He put on my cool outfit and we headed for the lake.  He also had the money that we were given for lunch and snacks.

I wished I could have stayed in the room and then I lagged behind as we walked to the beach.  He reminded me that I wanted to go to the beach and grabbed my wrist.  I tried to pull free but couldn't for he had a grip like an iron claw.  I saw one bright light – I don't have tell anyone that I'm the older one since nobody knows either of us.  Maybe I'll be safe in anonymity.

* * * * * * * * * *

Things started to go wrong even before we got to the beach.  A kid, eleven or twelve, came up from behind us and spoke to Mike.  "Hi,  I'm Ben.  Babysitting your naughty kid brother?"  Then without waiting for an answer, continued: "Your kid brother looks like a heap of trouble."

"Hi, I'm Mike.  Sammy is NOT my kid brother but I'm babysitting him and he is loads of trouble.  Had to spank him even before we left the hotel."  I'm sure that I was resembling a beet and wanted to run away but Mike had a death grip on my wrist.  Where the hell did he get all these muscles?  My ass still hurt enough that I did not want to try anything.

In the few minutes it took to get to the beach, Ben told us, er, Mike a lot.  He was a regular here and knew which part of the beach to go to.  Of course, it was dangerous to go to the 'older teens' section for they would clubber us.  Additionally, we wanted to avoid the 'adult only', the main 'family' section and go to the 'kids' section.  There were a few parents there but it was pretty empty.  None of the sections were crowded and in the kids' section there were some boys who were naked and some in just underwear.  The little girls had bathing suits for apparently it was only the boys who were naked or almost naked.

We spread out our blanket not very far from where Ben's mom's friend was.  Ben said that his mom was very cool and kept an eye on his kid brother, Petey, and came well-equipped with food, drinks and other stuff.  They were to come a little later and until then we just talked.  Mike remembered to put sunscreen on me.  It did feel nice when he rubbed it on but I did not like it when he pushed down my (his!) shorts and rubbed some on my butt.  That also gave Ben to opportunity to see that my butt was red from the spanking and he commented that it was a nice shade of red.  Fortunately, Mike prevented me from slugging him.  It got worse when I turned over and he got below my waistband when he did my chest this time affording Ben a chance to see that I was bald.

Mike then told me to put the lotion on him.  I immediately decided to get under his (mine) board shorts but he did not care that Ben saw him.  He already had some hairs and nobody expected him to have a lot and his tail was not red.

After a bit, Ben's brother, Pete, and his friend, James, (both ten) showed up and were introduced to us.  Pete was just wearing tightie-whites with Spiderman (having left his shorts with his mom) and James shorts without undies.  It was not long before they wanted to go swimming which is when the trouble started.  The two quickly shucked off the little they were wearing so that they were naked.  Mike told me to lose the shorts and briefs – like the other little boys – to go swimming.

I objected and he said that the shorts would be uncomfortable when they got wet and when dry they would be salty which would be irritating.  I continued to object but they said that all the little boys went naked.  I almost blurted out that I was fourteen but that would have been even worse.  I tried to bargain to just wear the briefs but I was told that was even worse than naked because they become transparent when wet.

"That's enough, Samuel!  Take them off – NOW!" ordered Mike tired of my arguing.  I refused and that got me into big trouble.  Mike pulled me across his out stretched legs and Ben immediately helped hold me in place without being asked.  Mike undid the fly of the shorts and asked the two ten-year-olds to pull them off me.  They did so most enthusiastically and then held my legs.  Need I tell you what happened then?  Right, I got spanked hard by Mike for the second time this day now with the others enjoying the show up close.  Mike even invited them each to give me a few spanks.  Ben just used his hand but Pete grabbed a flip-flop and really made me feel it.  James was not to be out done and did the same.  By the time they finished I was naked and also crying like a baby. Mike made sure I was well covered with sunscreen both fore and aft so they all got a good look at my small stuff.  I was glad to get into the water which both cooled and hid my red bottom and even hid my little pee-pee.  Playing around in the water made me forget that I was naked and it actually was fun especially since the water cooled my hot tail.

When it was time for lunch, Ben, Pete and James went to their supply depot and Mike led me to the kiosk on the boardwalk.  I wanted to put on my pants but he would not let me do so even though I begged.  "Nobody cares except you and you don't have to." he insisted.  Reluctantly, I went not wanting to be spanked again.  Actually, the young lady in the kiosk never looked at me below the neck when I placed my order.  We got our food and returned to the blanket to eat.

Soon after, the guys came over and said that they were going for ice cream and would we like to go.  That sounded good so we started.  What I did not know was that it was at the far end of the boardwalk and I was still naked like Pete and James.  I think Mike sensed I might be trouble and clamped his hand about my wrist once again as a warning to be good.

There were a lot of people in the ice cream shoppe and there were several other naked boys.  There were some teens dressed cool like Mike was in my clothes as I had started the day.  There was one girl my (real) age who was complaining about all the little kids in the place while the rest ignored us.  Mike, told her that she was a little kid not so long ago and that we all went through such a phase.  Unfortunately, her boy friend looked at me and I turned away because Mike pulled me.  I heard that guy say: "That brat has a long way to go.  And he was even SPANKED today."  Mike now had our order and quickly dragged me outside before I could get into trouble as the two laughed.

"Ignore the idiots, Sam.  Enjoy your ice cream."  He pulled me down the boardwalk a bit and said: "Hey, this is good stuff."  Soon the five of us were returning to our blanket.  I thought about how Mike kept me out of a fight.  When the others were finished they went to their Mom and Mike took advantage of our privacy to talk to me.

"How are you really feeling Sam?"

I confessed that I was ashamed of things.  Mike gives me time to say what I need to confess – how I yelled at my folks and even how I treated him.

"You almost got into a fight in the shoppe." he said.

"I'm not used to be being this way." I say as an excuse – "Nude."

"Whose fault is that, Samuel?"

Hell, he forcing me into deciding who's to blame.  Unfortunately, all this is my fault.  "Mine.  I was an asshole this morning and you showed me that you're more mature and I that need to grow up."  Mike smiles but does not say a word.  He left it all to me.  "I guess I owe Dad an apology for last night."

"I think that you do.  You seem to be agreeing with him also."  I question what he means.  "He said you need to grow up and now you just said the same thing."

Shit, Mike made look in the mirror and there a batch I didn't like.  Unlike the 'rents lecturing me, he gotten me where they haven't in years of trying for I was not happy with what I saw.  "Mike, what else should I tell him?  That you were my babysitter today?  That I know that I need to grow up a lot more?"

"I'm not sure, Sam.  I think that you have to decide for yourself – it's part of growing up.  Oh have you noticed that your being naked really is not of interest to people around here.  I haven't seen anyone staring.  Have you?"

I had to admit that Mike was right about that.  Even those stupid two in the ice cream shoppe did not stare at my little thing and they were the worst.

Just then the others came back and we had to stop talking which was probably just as well.  Petey and James invite me to join them in the dunes telling me that it is fun.  Ben says he'll stay with Mike and talk.

* * * * * * * * * *

I let myself relax and go off with the two ten-year-olds deciding that I'll just play being their age since we are all naked it shouldn't matter.  They want to know more about my spankings.  "Today was a different day.  Mike is very strict and I pushed to hard.  My butt paid the price." I told them trying to sound like it did not matter to me.  They both admitted that they got spanked by their parents and babysitters but not as much as when they were younger.  "Spanking you was a lot more fun than getting spanked, Sammy." they add as if I did not know.  I forgive them knowing that I would have done the same thing had I the opportunity and they really did not do much.

"The dunes are fun because it's girls' territory.  Just do what they tell you to and you'll have fun.  If you don't they get mean."  I don't get a chance to find out about this before we are surrounded by several girls.  They are all in bathing suits.  Pete and James both said "Good afternoon." so I did also.

"You're ready for us, Petey." said one of the girls.

"Yes." he replied as she grabbed his stiffy while another one did the same to James.  The pair let the girls jerk them off until they each had a dry cum and then they said thanks.

Then I became the center of attention.  I had my hands in front of my crotch to protect it and I would have run if I could.  "Put your hands down, boy." one of them ordered.  I refused and told them to leave me alone.  Pete told me to do as I'm told and enjoy it.  I should have listened for several of them grabbed me and pushed me down.  They sat on me and I couldn't move.  James reminded me that I should have been an obedient boy and enjoyed being pleasured.  Instead, they started to spank me.

The spanks rained down like water drops in storm except that they hurt.  I yelled for them to stop but they just laughed.  I gave up struggling and just took it.  I begged them to stop and promised to be good and eventually they stopped spanking me.  They rolled me over and grabbed my Weiner.  I got hard and it felt good.  Soon I came having a dry cum like the other two had.  They jerked me again and again until I came five times.  They left.

I was exhausted.  James and Pete both wanted to know why I resisted getting a hand job.  "I don't know," I said honestly, "but I surely won't the next time."  They both had several cums while I was preoccupied.  We went swimming so I could cool off my hot butt once again.  Later I saw Mike and Ben coming out of the dunes only wearing big smiles.  They took their time about putting their swim suits back on.

* * * * * * * * * *

At dinner I managed to apologize to Dad as I promised Mike when we were on the beach.  Our parents all wanted to know how the day had gone for Mike and me.  I thought that they were satisfied when I said that it was a learning experience.  It was only after dinner when it was just the four of us guys, that the discussion got into the nitty-gritty.

Dad pressed me about things and since I had said that it was a learning experience, he smiled and commented that being in charge made one grow up.  The timing was bad for we had gone into the garden and I answered just as we were sitting down on the hard wooden benches and I winced as my bottom hit the bench.  Dad noticed that and was concerned.  I had to own up everything – that I had been an asshole in the morning so that I had lost out to Mike which led to him being in charge.

There was a minute of silence and Mike's dad asked him and he confirmed it.  After a little while, our dads knew the entire story that we had swapped positions so that I became an under ten-years-old kid for the day while Mike acted as if he were a teenager.  I had to also admit that Mike had spanked me as I deserved.  Overall, I agreed that he had been fair and reasonable all day.  We mentioned that we had played with a few local boys but not that I had been naked most of the day.  Needless to say, Mike gained a lot of status, especially in his father's eyes, while I lost a lot.  (I had scary thoughts about what the 'rents would say about my staying alone the next time they stay out overnight and it was depressing.)

At the end of the discussion, I was given a choice to be made at breakfast time.  The next day I could go with the 'rents sightseeing old junk or to the beach – but only with Mike and with him in charge.  That was the easy part for I could accept that Mike would be in charge again having faith he would remain reasonable.  Then, the 'rents left us and Mike told me that I must go as a pre-ten year old again.  That was a dilemma but Mike had an answer.  If I went as a teen, then if we met Ben or the others, they would know how old I really was and then they surely would hassle me about having been a little kid.  I agreed to Mike's rules even through he said I would have to be naked at the beach again.

* * * * * * * * * *

In the morning after the 'rents left, I went to Mike room and we swapped clothes again before headed for the beach.  Mike had said as long as I listened to him that we would have fun and he wouldn't have to spank me.  He was annoyed as I was by the idiots in the ice cream shoppe so he said he would let me wear my shorts when we went there – if I was good.

Mike then surprised me and told me it was time for my 'maintenance spanking'.  He explained that was a spanking whose primary purpose make sure that the spankee remembered what misbehavior would bring.  "I read about it on the web last night.  It will help you avoid getting spanked on the beach in public."

I was very hesitant but he explained that should I slip he would be very severe with me should I decide to skip it."  I then saw the wisdom of his words and got over his lap with any further discussion.  Mike lowered the shorts I was wearing and proceeded to spank me with his hand.  I think he was a bit more gentle than yesterday but it did hurt although he did not make me cry.

On the way to the beach, I felt good even thought my bottom was rosy and warm.  I was not fighting the reality that Mike was the big teenager and I the little boy in his charge.  I told myself that I would do as Mike said and avoid any additional spankings.

We staked out claim to a bit of beach with the blanket and I immediately stripped to my birthday suit without being told.  I had gotten over a lot of my shyness since I had decided that I was a nine-year-old boy and it was nice to be naked.  We swam and played in the surf being joined by Ben and the others after an hour.  It was fun.  Ben noted my bottom was rosy and Mike explained about the maintenance spanking.

After lunch Mike and I went to the dunes.  Of course, I was already naked but Mike removed his suit just before we went in.  In only a few minutes, several girls appeared.  Here in the dunes we were very close buddies since we both were looking forward to being pleasured by them.  It did not go as we expected.  Neither Ben nor Petey had told us something very important – the password.  We were strangers and the password was required.  Mike said we would leave but they would not allow that.  "You must pay the penalty." we were told.

"And what is the penalty?" asked Mike.

"A spanking." they replied.  Then they went on to explain only one bottom needed to be spanked provided the other one does it.  Mike volunteered as he was in charge.  He got down on his hands and knees, presenting his butt.  I was given a beach sandal and told to give him ten good whacks.

When I hesitated, Mike ordered: "Do it, Sam."  So I did thus having the pleasure of getting back at him for several spankings he had given to me.  This was the first spanking I administered and it was fascinating to watch how his bottom changed colors first turning pink, then rose and finally red as I whacked him hard.  We had been warned that light spanks would not count.  Mike proved to a man by keeping quiet as I spanked him.  I'm ashamed to say I would have been yelling and then crying.

When the spanking was over, the girls were nice and jerked us off like the previous day.  We thanked them and left.  Mike put on his suit and we played in ocean a while.  We were hanging out of the blanket when our dads found us.  They explained that the sightseeing was not good and they left and came looking for us here.

Of course, they noticed that, first, I was buck naked and, second, that my tail was red.  Explanations were required.  It was quite awkward and fortunately Mike was able to explain things casting them in a good light.  It started yesterday when we met Ben and the others.  They assumed I was only nine or ten because of the way we were dressed.  As you can see, little boys don't wear much here.  In order not to embarrass me further, I pretended that I was that young.  To prevent discovery today, we continued the charade.

"Yesterday morning, after our, er, discussion I had to spank Samuel which also encouraged good behavior all day.  This morning Samuel agreed to a maintenance spanking to make sure he wasn't spanked during the day."  Our dads were nodding not sure of this and then Mike continued.  "Yesterday, when we met Ben and the others they assumed that Samuel was only nine or ten because of the way we were dressed.  As you can see, little boys don't wear much so to prevent further embarrassment, Samuel went along with their assumption and was naked like Pete and James.  We had to continue the act today so as not to give away yesterday."

When Dad questioned me about stuff, I had to answer.  "Well, it's not the greatest but it sortta fun for a couple of days.  Surely better than the sightseeing which must have really been terrible it you could not take it."

The next day we watched the locals play soccer.  I was very careful to behave well so that Dad would not spank me nor have an excuse for a maintenance spanking.

Mike and I were allowed time together and we became good friends and we both knew that he was in charge.  Once I got back home, the 'rents decided that I needed new rules.  They actually discussed them with me so that I had a say.  For many things, they were more restrictive with the objective of helping me grow up faster.  That was something I agreed that I needed to do.  I was also allowed to decide how I was to be punished in each case – spanking, grounding or extra chores.

* * * * * * * * * *

It was just a couple of weeks after I got home that things radically changed.  My folks were going out and they had, as always, arranged for a sitter.  (They had stopped saying babysitter a couple of years earlier.)  They said that in keeping with my wishes, they had found Gilbert, a male, as I had been objecting to the teen girls they had previously hired.  They had carefully checked his other clients and had gotten glowing reports how he was good with older boys such as me.  Because of that, they agreed that he would have the right to discipline me with spanking should I be naughty, disobedient or disrespectful.

I immediately figured that I would have someone that I could relate to and who would tell me about being an older guy.  I was all excited.  When he was due, I even rushed to answer the door when the bell rang.  I was disappointed that it was just a kid – definitely not even thirteen; maybe not even twelve – there.  "What do you want?" I asked.

"Hi.  You must be Sammy.  I'm Gilbert, your new babysitter."

Mother told me to let him in.  I groaned.

Go to: My New Sitter Is a Boy

© Copyright A.I.L. February 25, 2011

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