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Timeshare Tails
Angel Fire, Part the First

by Spankmeokc

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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 these years.

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

Wha’ja do?

He replied: 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 you?

I have to tell the truth: Yeah my dad spanks me with a hairbrush on my bare butt. I just hate it.

That’s rough too. Well, keep this pond in mind when you get spanked again. It really saved my ass today

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:


Interspersed with my


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 no