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: 01 Mar 2018
Timeshare Tails: Angel Fire, Part the First, A Tooth of Time Tail
Hi again. It’s Tommy here. I’ll be your narrator for this story, which happened just a while back.
I was on a road trip with my wife, Annie. We were on our way to spend a week in a timeshare in Angel Fire Ski Area in New Mexico, when we went past a sign pointing the way to Philmont Scout Ranch.
Note: As for why we’re in this area, see Part the Second
I couldn’t help but remark:
Boy, does that bring back a lot of memories!
What memories sweetie? Annie replied:
I don’t remember you talking about that place. Is
it like a dude ranch?
It’s not supposed to be. I laugh at the thought.
When I was first there, the ranch was
an executive training center for a boy’s organization. My dad was a professional with them for a while –
when I was in grade school. We stayed at the camp during his training for two weeks almost every summer.
Later on, as a teenager, this boy’s group I was with went there on a sort of wilderness campout for 10
days every summer or so. It was a great place really.
I begin to reminisce...
When I was younger and went with my family, the executives (all men) had their training meetings in the former ranch house. Originally a real ranch house for a working ranch, it was now a big lodge with conference rooms, auditoriums, a dance floor and a long wrap-around front porch that looks out on a range of blue mountains across a vast plain, originally with herds of cattle and wild mustang horses – now just fenced off. The head honcho’s of the organization all stayed in the lodge; the trainee’s and their family stayed in Tent City – a set of permanent tents. There was row after row with maybe twenty-five tents in each row, all with a wooden platform between them to avoid the ground turning into a sea of mud. It had a formal name after some big wig in the organization, but everyone called it Tent City. The place was full of kids of all ages, running around eagerly to see everything all at once, at least I was.
The place had activities for the whole family: hobbies, crafts, classes, small race cars you had to carve yourself out of a block of wood; hikes in the daytime and square dances or movies every night. I had a lot of fun there and looked forward to it every year. We met kids from all over, who all seemed to talk funny, not like me.
Sounds like lots of fun. Was it like that when you went back on the wilderness camp-outs?
Oh, no! That was a whole different thing.
I was between 12 and 16 then. For us teenage scouts, we were supposedly in training to be men, which at the time seemed to require military style indoctrination. But there was no Tent City on the trails. Each group of kids, each troop, we had to carry our tents on our backs along with our sleeping bags, all the food and cooking pans and utensils for the trip. We were allowed a change of clothes and a very few personal items. All these were crammed into a pack set up high on our backs, on a frame designed to distribute the weight so as to allow up to one-hundred ten or twenty pounds on a 90 pound kid, like me at the time.
We had to take everything we needed up and down the trails, set up the camp each night and take it down every morning. We had to pack out our own food for the trip and carry it the whole time; lighting the fire, cooking the meals and cleaning up everything every night and morning. We were mostly pretty tired every day. On the good side, no matter how bad the food really was, it tasted great after a long day on the trails. You had to learn to eat quickly when you’re with a group of hungry teenagers!
This one year, I must have been just barely twelve, maybe thirteen; I remember our troop was on a trail that suddenly emerged into a clearing with a pond in the middle. Several trails met there so the pond was already full of guys, maybe 50 or so, all skinny dipping, you know, swimming naked, in the pond. At first it was pretty funny to see all those naked guys jumping or diving from the cliff. But it looked like great fun though so we all raced to get in the water.
Three trails curved in from the trees, so you could not see the pond at all until the last turn, except for this one trail that came down from a ridge above the meadow and ran along an edge about 20 feet above the pond, curving around and down to meet the meadow. It was perfect for picking your own height for diving or jumping into the water. The pond had its depth marked at regular intervals, so it was safe for diving and swimming. No life guards, of course, but I’m sure most of the older boys had their life guard badge – like several in our troop did!
It was my first time skinny dipping; I was pretty modest back then and normally I would have been embarrassed almost to tears to be all naked with my cock and balls and butt in full view of everyone there, even guys I didn’t know, but everyone else was stripping off so I couldn’t hold back without looking like a pussy.
Uh, you know what I mean. As Annie digs me in the side with her elbow.
Pretty soon I realized how fun skinny dipping really is. I just loved swimming without the tight band around my waist from the suit or the tight elastic waist band of my swimmers jock strap and I loved the feeling of the water swaying my dick back and forth as I swam. It was totally new to me. I was pretty worried about diving naked the first few times, I mean, would it hurt my balls with a direct hit, if I hit the surface wrong? Answer was YES it could hurt, WOW; but I watched the other guys dive and learned how to protect my balls for the next times.
And it was just fascinating watching all the naked guys. I mean I’d never seen so many genitals, all different sizes and shapes and shades, of dicks, balls and body hair; we were mostly adolescents then, in all manner of physical development but there were a number of older teens, and most of the young adult advisors were naked too, with fully formed and adult sized cocks and large low hanging balls. I could gaze at any of them curiously. Even when a few of them caught me looking, they just grinned at me. So it was OK.
I had always wondered whether I was cut or ’uncut’ but was too embarrassed to ask what that meant. But here I overheard some talk and saw the guys’ dicks they were talking about, so I quickly looked at mine again and figured it out. Gee I was really stupid back then!
You could have just asked me. Annie says, batting her eyes.
But that was before we were dating. I replied, innocently.
I knew anyway. All the girls learned everything about the boys as quickly as possible. Didn’t
you know that? And circumcision status was a hot topic, for sure. She spills the beans, after all
Gee. All this time I thought I had some privacy growing up. Guess not!
There was more than one guy that started to get a hard dick; I hadn’t seen that before, except for mine, of course. But they just jumped, or were pushed, into the chilly water of the pond, which took care of that issue. So I did the same when I started to get hard – it worked like a charm.
When we had swam a bit, enough to cool off from the trail and to play around, but weren’t ready to leave yet; so we all just sat or lay in the sun to dry, all stark naked but it seemed very natural by then and very normal. – It was cool.
There was one scout, about my age I guess, who when I noticed when he came into the clearing because he was reluctant to strip – His buddies jumped him and pulled all his clothes off in about 10 seconds. Turned out he had a very cherry red butt, seemed to be from a recent spanking, based on the kidding he endured.
I was curious about other spankings, even back then, so after we were both drying off, I plopped down next to him when he was on his tummy on the grass and I had to find out.
That’s pretty red. I pointed out.
Yeah, I got spanked by my dad about an hour ago
We were hiking, and I pulled out my knife and started throwing it at trees and stuff
as we went along. Then the trail did this switchback thing and my knife landed point first in the ground
right by my dad’s boot. Bad move!
He grabbed my ear and marched me to a tree stump; then pulled my shorts and underwear down and
spanked me over his knees. I was really crying right away; but then he picked up this flat wood piece
off the ground and just paddled me with it! Man that really hurt bad! When he finally finished he made
me get up right away and march here. Dad never lets me rub – he wants the sting to last a while.
I was bawling most of the way and just wanted to lie down and cry when I got here, but the guys stripped
me off and threw me in the pond. I’m glad they did now; that cold water really felt good. My rear still
hurts but it’s a lot better now.
This time Dad even spanked my butt crack – see.
He reached back and spread his butt cheeks apart, showing me how red the inside of his butt cheeks were and gave me a bird’s eye view of his asshole, along with a direct view of his balls and cock laying between his legs. It’s quite a sight, for me, my first of an anus.
I’m sorry; – I bet that still really hurts! I sympathize, as one boy to another.
It sure does; but that’s all right. I guess we all get it from time to time. You get spanked don’t
I have to tell the truth:
Yeah my dad spanks me with a hairbrush on my bare butt. I just hate
That’s rough too. Well, keep this pond in mind when you get spanked again. It really saved my
I agreed, not knowing that only tomorrow I would be longing for the cool waters of that pond for my own burning butt.
Our campground for the next two nights was nearby and we set up there ready to take the trail in the morning to their famous Tooth Of Time You saw it on the sign back there. It’s this granite crag sticking out of the hills across the creek. It did look like a tooth in the jaw of the mountains; just like the postcard we could buy in the base store to send back home.
The next morning our troop of boys got a late start, not sure why now. But we missed the guided escort to the Tooth of Time and we decided it would be easy to find the trail on our own; after all, we were seasoned trail hands now. We voted on a likely ravine to go up, one just to the right side of the tooth. There were spruce and small fir trees everywhere, with chipmunks pestering us for food all the way. Apparently they think scouts are pushovers for snacks.
We got up to the lower part of the Tooth but never seemed to find a trail; and finally one group of boys just wanted to climb straight up the side of the crag. I didn’t want to and I was supposed to be in charge, but those four guys didn’t want to listen to me and just started up. So I and most of the group continued up the ravine to try to approach the crag from the top, which sounded to me like a better place for a trail.
All of a sudden we heard a scream as one of the guys, named John, slipped down the side of the rocks he was clinging to. He caught himself, but nobody in that group could move, they had each gotten to a place where they couldn’t go up, down or sideways. We came back as near as we could and tried to guide the guys to better spots, from what we could see. We got a couple of them to safe enough places that they could scramble on down to meet us. But John – who was about my age, he lived down the street from me – the shrub he was holding on to slipped out of his hands and he fell down the side for about 20 or 30 feet. He became caught up in a tree before he hit anything hard and we were able to make our way over to his position and help him down.
Meanwhile another troop of boys, on their way from the real trail on the top of the Tooth of Time, came down the ravine and helped us with first aid stuff and getting John down the ravine safely. John had sprained his ankle, had plenty of bruises and lost some skin, but nothing terrible happened, to him anyway.
When I got back to the camp with everyone else, they had already evacuated John to the camp infirmary. I thought I had handled that adventure pretty good, but my dad was furious that I went up without a guide and then I let that group of four guys get away from me. For some reason it was all my fault that they refused to listen.
As I tried to explain he just pulled me to the middle of the campground, folded his hands over his
chest and ordered in a loud voice:
STRIP NAKED NOW
From experience I knew that at this point any argument on my part he would call backtalk and would just make things worse for me. So I quickly stripped off my clothes and stood there naked in front of maybe 50 boys. Now I was the center of their attention.
I had been naked the day before when we were all skinny dipping, so I wasn’t embarrassed to be in my birthday suit – but I and everyone there knew I was about to get spanked and I was sure embarrassed about that. I didn’t want to be crying like a baby in front of them all; but was pretty certain it would happen anyway. Still, I was determined to try to take it without giving anyone the amusement of watching me making all those noises.
Dad pulled me towards one of those portable cloth camp stools, the kind that fold up, sat on it and pulled me over his lap. The stool was low enough to the ground that my face was in the dirt so I tried to put my hands under my face to protect it. Then he started in spanking me like crazy. Fast and hard! Over and over! Again and again! All I could hear was this relentless:
SPANK. SPANK. SPANK. SPANK.
Interspersed with my
I/M SORRY PLEASE.
My best resolve to show how tough I was – was soon completely destroyed when suddenly I was crying into the dirt in front of everyone. It happened before I could do anything to stop from crying. Oh Well. Not the first time or the last.
After this long hard spanking, I heard him order
Bring me the hairbrush from my pack and I
just knew it was going to get a lot worse.
Sure enough, when he stated walloping my poor butt with that brush I arched up and just yelled at the top of my lungs, looking directly into the face of these 4 scouts from my city. I didn’t really know them but their scout group had traveled with ours to camp. They all had big grins on their faces as they watched my misery.
I have to say now, even though I wasn’t in a position to appreciate the natural beauty of that campsite just then, that beyond their face I could see this amazing view of the Tooth of Time above their head. At the time I just hated having this front row view of the direct cause of my burning pain, which was getting worse every few seconds.
It was like my own tail was being roasted by the Tooth of Time, which seemed to be leering at me with this evil toothless grin!
Even so, all I could do was yell and cry and bawl my eyes out with all these guys watching as dad turned my ass from lily white to red to a shiny cherry red mixed with the inevitable black and blue bruising with which I was all too familiar.
He never stopped spanking me until he decided it was done, no matter how much I begged and cried. So I learned, once again, that I had to take whatever he dished out, not matter what. Eventually I just lay there, exhausted, totally worn out from my struggle and my yelling and my bawling, not knowing anything but the fire and pain shooting from my butt and seeming to consume all my body and brain.
When he finally slowed down, stopped and pulled me to my feet, I was the usual crying mess, tears
and snot running down and mixing with the dirt my face had been pushed into. Dad marched me over to the
flagpole; put my nose against it and ordered
Put your hands on your head and stay in place until I
say you can move. If I find you out of position you get another spanking worse than that one! Understand?
I nodded – Unable to say anything in between my sobs.
I didn’t hear you!
Yes sir. I eventually managed, totally miserable, and now longing for that cool water pond
we were at yesterday.
While I was kissing the flagpole, Eskimo style, most of the guys in camp came over for a good look
at my butt. Who could blame them? They were generally sympathetic with a bunch of
Sorry, Man. mixed
Boy, You got it bad.
The kid with the red butt from the pond yesterday came over and said:
You got it worse than me,
It was my turn I guess. I replied. We looked at each other knowingly. Then he told me the
Well your gonna have another turn tomorrow. I heard your dad say he’s going to spank you every
day that kid is in the infirmary. He said that since that kid is having a bad time at this camp, you will
be too. That’s rough man.
I start to cry again, feeling very sorry for myself.
I’m such a crybaby. It’s so embarrassing!
He comes up and puts his hand on my shoulder.
It’s OK. Don’t be ashamed! We’re all crybabies when we get a spanking. All the guys I know talk
tough, but when their own butt is being walloped they all cry. It’s just the way things are.
As he leaves those four boy’s from my town that were grinning at my face come over.
You must like getting spanked.
No I don’t. Who would?
Then why is your dick getting hard?
I didn’t really know what he was talking about, since I hadn’t learned to jack off yet, not much anyway. Or seen anyone jack off. Well, that was about to change too.
The next couple of days started for me with a sunrise spanking by my dad. I’m pretty sure he wanted my butt to be the same color as the sunrise. At least that’s what they guys told me it looked like. All I remember is crying and bawling with that evil hairbrush making a mess of my ass for at least half an hour before each breakfast.
Finally it was time to head back to my home city. John had been released from the infirmary. Apparently he had a great time there, with no backpack to carry around, someone else to cook the food and able to sleep in a real bed every night. So those last few days: John had a carefree camp life while I got spanked every day! Life was so unfair to me. Somebody up there was out to get me for sure!
On the last day I helped pack our stuff in the cars, it was pretty tight fit. There were three cars and an old van with a set of double doors in the side. We could stuff most of the camping apparel in the middle of the van, it left free just a seat by the driver and a fold down bench seat in the very rear, facing out the rear window with enough space for a few boys to sit.
Those four scouts from my town that had made fun of me came over.
Hi, I’m Randy, this is Jack, Zack and Ted. We figure you’re still sore, so why don’t you ride
with us back here in the van. That way there won’t be anyone else to bother you. We can shoot the bull
or even sleep without anyone else around.
Seemed good enough to me and it was nice of them to think of that. So I talked to my dad and he agreed, glad I was making friends.
There was just barely enough room for the four of them and me to squeeze in, it was tight quarters.
Unfortunately, as soon as the van started down that dirt road from the campground parking lot, I knew I was in trouble. Every time the tires hit a bump – it rocked that van up and down, the shocks must have been completely worn out. At every bounce, when the van hit bottom, my butt bounced against that seat and it hurt bad. On the upward swing it bounced me off the bench seat only to hit against my rear harder the next time down.
And I had 800 miles of this to go. This trip was going be pure Hell and it would last forever.
The first road out from the camp was more just no more than a rough dirt road with a lot of bumps and potholes. After several bad bumps I started to cry again, my butt hurt so bad.
I was afraid it might hurt like that. Listen why don’t you lay on your tummy so your
butt won’t get hurt so bad.
How could I do that, there’s not enough room for all of us sitting down; there’s no room
to lay down!
You could like, lay over our laps, you’re pretty light. It’s be OK won’t it guys?
There is a chorus of
Sure. Be glad to. Anything to help man.
So I agree; anything to reduce the pain in my butt.
When I lay down over their laps, Randy was in place next to the window, which put my face in his lap; then Jack was under my torso; then Zack with my crotch over his lap and finally Ted. Ted had me bend my legs up toward the van roof; I rest them on the side window so I could fit comfortably, sort of, on the narrow bench. Even so it was just like heaven to not have that burning pain in my rear at every bounce of the road; However, my hands were in an awkward position, with one dragging on the floor of the van next to the back door, the other stretched back down my side while I was trying to avoid touching any of the guys.
Randy goes helpfully:
Here let me try this with your hands. and he gathered both my hands
up as someone held them in place behind my back.
That’s a lot better. Isn’t it? Better than bouncing
up and down on the bench seat anyway!
I wasn’t really sure about that, for some reason, but my butt felt so much better not being assaulted
by the world I had to agree.
That so much better. You guys are the greatest. Just say the word and
I’ll do something nice for you too. Anything you want!
I relaxed and let my face rest on Randy’s lap. I was just starting to relax enough when I felt a bulge start to grow in his shorts under my cheek. He must be getting a hard on. I didn’t want to embarrass Randy so I started to move my head the other direction.
But Randy grabbed the back of my neck and held it still – first grinding my cheek into his bulge; then he straightened my face up and Jack, the guy next to him, pulled my head up while Randy used his hands to unsnap and unzip his cutoff jeans.
I tried to move my hands up to protect me, but the guy holding my hands wouldn’t let them out of his grip and I realized I had been pinned in place and was now completely immobilized, over their laps!
As I looked at Randy’s lap in growing horror, Randy pulled his dick out of his underwear, all big now, bigger than any I had ever seen before and now it was up close. He and Zack both held my head still while Randy pushed his huge hard cock against my lips, then he forced my mouth open and slid it into my mouth, all the way in it would go. They moved my head back and forth along his cock.
Randy leans down and says in my ear.
Suck on it now. Suck on it good! And no teeth. If I feel
any of your teeth, I’ll knock all of them out and throw ’em out the window.
I started making a muffled noise in protest.
But immediately feel an explosion of fire on my butt as I hear:
We all heard you promise to do anything we wanted. This is what I want now, and you’re in no position
to complain, are you. We can spank you very hard for the next 800 miles. Is that what you would rather?
Show him, Zack! Spank him.
I feel my shorts taken down and Zack spanks me on my now bare butt. I can’t believe how hard he is spanking me in that small space of that van and how much it hurts on top of my last three days of spankings. It’s my second spanking of that day and it really, really, hurts bad!
NO NO NO, is my muffled response. Not much noise came out with his dick in my mouth, but he
pulls out for a bit.
Are you going to do what we want now?
NO NO. I don’t wanna’.
Spank him again Zack until he begs us to stop.
Zack spanks me more, with enthusiasm this time. After not very long I realize there are four of them and they can keep this up forever. And my butt is already heating up really fast, on fire now!
OK STOP, I’ll do what you want.
Then you’re going to suck my cock good. Right?
Yes, OK. I go, defeated
In fact you’re going to suck all of our cocks. All we want you to. Right?
Yes OK Totally humiliated now.
Just please don’t spank me again in the car like that. I add.
Randy quickly agrees.
All right, we won’t spank you in the car. We promise.
Thank you for that. Relieved that I wouldn’t get spanked again.
And they all laughed at me.
Randy took over moving my face up and down his cock until he suddenly pushes my head down against
his pubes and his cock all the way into and down my throat. I’m starting to gag and the other Jack says:
You have to relax your throat muscles unless you want to choke on his chicken!
I manage that a little, to relax my throat, as I feel him spasm and something liquid hits at the back of my throat to slide down my gullet. It must have come out of his cock. What the hell was that? It didn’t taste like piss.
Oh man! That was great! Guys, you’ve really got to try this. I heard how much fun
a blow job is, but it’s amazing.
I go to myself:
So that’s what’s happening! I’m giving them a blow job. I though just girls did
One by one they switch places in the car and force me to give each of them one of these blow jobs. I overheard them calling the stuff they were shoot out of their cocks their cum.So it was this cum I was swallowing. That must be what came out of my dick sometimes.
They were insatiable, as only horny teenage boys can be. I have to give each of them several blow jobs, in a never ending circle.
I did learn how to suppress my gagging and they taught me to lick and suck the head of their cock and the underside that seemed to be so delicate. I had hours of constant practice before we stopped for lunch.
The guys put their arms around my shoulders as they marched me to a separate booth in the diner.
Look you’re going to tell your dad that you want to ride with us and you want to stay in our motel
room tonight. Right?
Ok I go, totally submissive now.
You’re learning pretty quick, but you need to practice more this afternoon, don’t you. We’ll help
you with your practice. Won’t you like that?
All afternoon it was the same. I figured they had to get tired of it or sore or something. But whenever one guy had to stop, there was always another randy teenager with a hard on ready to put it in my mouth.
I sometimes wonder how much cum I swallowed on that car trip. Seemed like a lot.
We stopped for the night at one of those cheap motels that used to be along every major highway. You remember, the ones with the obligatory cheesy souvenir shop and alongside some amazing and impossible sight to see for only twenty-five cents.
The Mystery Room,
The Room of Horrors,
Amazing New World,
They used to be all over the place but are now run out of business by the decent motel chains.
Anyway, Randy had me stay in motel room with the four of them, a room with two double beds. So I was beginning to worry what he had in mind for me.
But I was just ready to relax when Randy showed me the paddle he had brought in that cheapo souvenir
shop next door. It had few holes in the business end along with a painted image of a crying boy with a
shiny red butt which had stars shooting away from it and a painted label
TEEN-AGE ATTITUDE ADJUSTER
They all laughed when he pulled it out of his bag; but I was scared when I saw it.
You said you
wouldn’t spank me, you promised!
That’s almost right. We promised to not spank you in the car. And we’re not in the
car now, we’re in this motel room. You’re the newest teenager here so you’re getting your attitude adjusted!
You butt is going to look just like this picture here in a couple of minutes. But I will give you a choice,
if you want.
We’ve decided we want to fuck you now.
What? Fuck – what do you mean, that’s something you do with girls.
Randy explained carefully that it meant they were going to put their cock in my butt, whether I wanted it or not. And my choice was to be spanked by each of them and then Randy only would fuck me, or I could get fucked by each of them and then only Randy would spank me. They all laughed while they watched me work it out.
I didn’t know what fucking was, but it didn’t sound fun for me. But I knew I didn’t want to be spanked at all, let alone four more times. So I chose the four fuckings with only the one spanking from Randy.
Looking back on that night, I’m know that none of them had every fucked anyone before, boy or girl, although the way they talked at first they were giving lessons to Hugh Hefner. As If.
Then didn’t know about foreplay or lotion, or anything. Each of them tried to push their dick in my ass, but I held my anus firm and they didn’t know what to do.
They finally decide that fucking must mean they put their cock between my butt checks, as I held my cheeks tight together and they rubbed back and forth, or in and out of what they called my tunnel of love until they shot more cum.
Whatever, at least it didn’t hurt as much as a spanking. It’s funny now, But Randy spanking me wasn’t funny at all.
He used that paddle all over my poor rear. I started yelling right away and they couldn’t shut me up and had to stuff a wash towel in my mouth to keep the noise down. When he finally stopped I was a crying snotty mess again.
They put me to bed between Randy and Zack. I didn’t care as long as no one was spanking me.
But in middle of night, when it was pitch black, I felt a hard cock slip between my lips and pump into me. His moans woke up the other guys so I had to give a blowjob to all four cocks again.
Next morning Randy paddled me again to make sure I was too sore to sit in the car.
So I spent the last 5 hours of the trip sucking their cocks over and over. At least I didn’t have to get fucked again – that trip.
When we finally stopped at their scout post and let them off, I was never so glad to see anyone go away.
See you around was Randy’s parting remark.
I was pretty sure that wasn’t going to happen, but I just nodded and waved.
I dropped out of scouts eventually, but once I learned to jack off, I started to use my memory of
that trip as well as my memories of getting spanked as my inspiration. Go figure.
I finish my tail and my attention comes back to the road as Annie leans against me:
told me that one before. Do you think it has something to do with your spanking fetish now?
I don’t know. I’ve read up on it, but nobody gives good reasons why some guys disregard spankings
and for some it becomes a way of life, or sometimes an obsession.
Personally I like to think I balance my need to be spanked with my great sex life with you!
Well that’s something I can help with sweetie. Are we there yet?
Yeah, we should be about at the turn-off to Angel Fire for our next fun-filled timeshare adventure!
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