But What If...

But What If... Older and Bolder

By His story, buff

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This story is intended for ADULTS ONLY. It contains explicit depictions of sexual activity involving minors. If you are not of a legal age in your locality to view such material or if such material does not appeal to you, do not read further, and do not save this story.
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BUT WHAT IF... OLDER AND BOLDER

His story, buff

PROLOGUE

As readers of my story ' But What If...' will know, my real-life situation in 1955, at age nine did not, in fact, leave me embarrassed and naked in front of a bunch of girls. But one of my recurring fantasy dreams posed in that story, did leave me in that state of humiliation.

But what if, one might also suppose, I had rejected the pledge challenge when I was nine going-on-ten BUT had reconsidered my ill-advised choice a couple of years later, say when I was nearly 12 and still keen on hanging out with my older brother Fred and his friends? What if the onset of early puberty made the whole idea of a stripping initiation a lot more interesting and, perhaps, even exciting?

What might have gone down had I been bolder when I was older?

ANOTHER SCENARIO OF WHAT MIGHT HAVE BEEN

It didn't happen right away, but within a year and a half I regretted my cowardly reaction when told to strip as part of an initiation for membership in my older brother's big-boys club. I had been nine years old back then, but now, in the summer of 1957, I was almost as old as they had been then. I'd be 12 years old in a few months and could see that manning up as I reached teenage status might demand some embarrassing acts of bravado and daring-do. What's the big deal about being naked in front of a bunch of guys? I'd be in high school soon anyway and would be nude in the showers and the locker room at gym time. So it's the same thing with only one difference; I'd be the only one not wearing clothes.

Well, I guess there would be one other difference too. Not being naked to wash up and then get changed... but being made to take off all my clothes so they could laugh at me and maybe strap my bare butt. But I've heard that happens to freshmen in high school locker rooms too and even to girls in their gym classes. I was talking myself in reapplying for membership in the big-boys club. And I'd man-up this time!

I figured my brother George still hung out with most of the same crowd as a few years ago. Tom's family had moved away, but Fred was still his best buddy and I had seen Kevin with them along with some older boys I didn't know. George never said anything to me about 'club business' or what his friends were up to, not since I had turned chicken and refused to strip in Fred's garage back when I was too young to know better. I wasn't even sure there was a big-boys-club still. But I was going to find out.

George was a bit surprised when I brought the subject up that night. But he seemed impressed when I told him I was more secure in my feelings and more self-assured. He nodded understandingly when I told him I'd heard from classmates with older siblings and knew some kind of informal hazing of ninth graders was common and that even the school board turned a blind eye to the occasional pants dropping in the school hallways ( I had made that last part up to impress George and make him think I was okay with being stripped naked in front of boys. )

He said he'd talk it over with the guys and let me know by the weekend. It turned out they no longer had a formal club, but they were still a tight group and even more so now that they socialized with upper grade fellows who were 16 and 17 years old. George got back to me on Friday afternoon and said I could put my case forward the next morning.

"But you have to prep yourself early tomorrow morning, Vic." said George later that night.

"What do you mean?" I asked "Like a big breakfast or maybe having nothing to eat?"

"Nothing like that. Vic." replied with a chuckle. " It's about your manhood and the way you present your body. See, you are asking to hang around with teens who are more mature in a physical and, well, personal way. Manhood is around the corner for most of us and you say it sort of is for you too."

"Well, not as close as you guys, George," I sheepishly said, " But I'm getting there and, if I do say so myself, I'm coming along nicely .. you know, in the man-hair department." I was referring to the pale fuzz in my crotch and balls.

"Ah, but that's just the point, Vic," said George impatiently. " That hair isn't as important to older guys, but getting hard down there and knowing what to do with it, is important and a sure sign of manhood. So tonight you have to shave off any hair or fuzz under your arms and anywhere around your crotch.. especially your balls, they have to be completely smooth."

"I don't get it," I said sincerely confused, " Wouldn't pubic hair mean I'm almost a full-grown man?"

"Yes, it might. But fuzz means you're still a little kid and you don't want to bring the proof of that to the pledge ceremony, not if you really want in. So I convinced the guys today that you want to show you can start fresh and, even though you do have manly hair, you are going to shave it all off tonight and prove your manhood in a much more important way."

"Okay, I can sort of see that" I admitted. " But what kind of proof are they looking for then?"

"That leads me to the second prep instructions for tonight. I know you've been getting your bed sheets messy the last couple of months.. and that's a good sign of early manhood, Vic. " smirked George as he saw my face turn red. " It's okay, all boys your age do. And besides, " he added just to freak me out some more, " Mom knows, of course. She washes the sheets, so how could she not know?"

Still blushing and now stammering in shock I asked, " Uhhh, so you mean to prep I have to play with myself down there? And like come all the way?"

"No, stupid. Just the opposite." George was delighting in my embarrassment. " For tonight and in the morning, you are NOT to touch yourself. You're going to prove your manhood by jerking off at the pledge ceremony and you don't want empty dry balls for that."

I was actually relieved George was helping me with my prep. Happy for two reasons: one, my body hair was only fuzz. And two, I wasn't sure I could shoot even a half-load jerking off. So storing some up was a really good idea."

The next morning George woke me up early and told me that they didn't have a clubhouse as such and Fred's dad had turned half his garage into a woodwork space, so that was not available. But the town's recreation center wasn't open until 10 a.m. on Saturdays and the guys were planning on shooting some hoops there mid-morning. So if he and I dropped by right after breakfast, say 8:30, I could apologize to Fred for what happened last time and tell them that I had learned not to be a big-baby and that I was ready to prove I could man-up this time.

So I arrived ten minutes early and was surprised to see ten guys on the basketball court. My brother along with Kevin and Fred were among the group. George told me he had already explained things to everyone. But he made formal introductions and a guy called Pete, who seemed the oldest one there, suggested we seek the privacy of the space behind the dumpster in the rear of the building.

"Some intimate business involving privates," Pete said, " Needs privacy for everyone's protection. "

I wasn't quite sure what that meant but I nodded my head in agreement. It was a real mess in back of the dumpster. Lots of cigarette butts and half a dozen crushed beer cans plus really tiny thin plastic bags with some dried-up goo in them. ( I later learned they were spent condoms ) I started to explain why I wanted to be in their gang and began with a total apology to Fred who was really nice about it, saying everyone deserves a second chance.

"I'm really grateful for that, Sir." I replied, trying to sound deferential and cooperative. " And I'm willing to take up where we left off a few years ago, my stripping and giving you all my clothes. But before I do that, I have to have your assurances, your sacred promise of privacy and secrecy."

"We want that too," smiled Pete.

"Just to be certain," I went on, " Swear that what goes on here, behind this dumpster stays a secret. No telling anyone else. And two: I'll give you all my clothes for this pledge ceremony, but at the end of the initiation I get to go home wearing all my clothes. Deal?"

"Victor!" laughed Pete. " we wouldn't have it any other way. We won't say a word. But you have to swear to secrecy too, no blabbing even to your mommy. And we insist you wear all your clothes home. They may be a bit soiled, but you have to swear you'll wear them anyway. Okay?"

I nodded my head vigorously and swore to all my pledge terms. And, just like years before, Fred began by saying to me, " First of all, Vic, take off all your clothes." This time I just said, " Yes, Sir" and proceeded to untie my shoelaces, shuck off my sneakers and remove my white sweat socks which I rolled up and tucked into the sneakers and placed them on the far edge of the dumpster.

Now barefoot, I decided to show them how cooperative I could be, so I asked Pete what he'd like me to take off next. He sort of smiled and looked pleased at my submissive demeanor as he told me to ditch my t-shirt and put it rolled up on top of my shoes and socks. This I did and before I could undo my belt to remove my short pants, George told me to hold my arms up in the air for pit inspection. I passed the no hair requirement, of course.

My belt I handed to Pete instead of putting on the pile. I figured I'd be getting a spanking, paddling or strapping soon, so that was no surprise. My khaki shorts dropped to the pavement and I stepped out of them and put them with the rest of my clothes. I was about to peel off my tight white underpants when Pete told me leave them on for a minute and grab my balls with one hand and my cock with the other and start playing with myself and try to make a tent inside my undies.

I was not prepared for this. But I did my best, stoking like mad. Much to my surprise, I not only got hard quickly, I even made a tiny wet spot on the inside of my underpants. I tented like a real man! They noticed and even applauded. Maybe I got a stiffy because it was the first time in front of anyone. Whatever, I was proud of myself and gladly dropped my underpants to my feet when Pete told me to. He had me continue to stoke my cock slowly just to keep me hard. I had already walked out of my fallen underpants and Fred picked them up for me, seeing my hands were otherwise occupied, he said.

My shaven balls meant I was body hair free and, with my still stiff cock in my hand, it looked like my manhood proof was well assured. In fact, Pete confirmed that my application to pledge was accepted now and I was ready for the initiation that, if successful, would lead to gang membership. A spanking, to be followed later by a strapping with my own belt, was the next pledge task and I told them I'd try my best not to embarrass my brother and Fred by crying.

"Good,' said Pete as he drew up a wooden milk crate, sat down and told me to get my bare butt over his knees for the first of ten spankings. They intended to hand spank me until my buttocks was very red, and I better not weep, sob like a crybaby. Because if I did, they'd just hit harder and for a longer time. I was beginning to feel my manhood shrink ( both figuratively and literally.)

Now I had had my fair share of parental and grand-parent spankings before. And always on the bare, although only once before, when I was four years old, was I spanked buck naked. But what boy in the 1950's didn't get OTK spankings on the bare?

But this spanking had a tanning target of fire-engine red butt cheeks. And it was administered by ten older boys who really seemed to enjoy giving color to my butt. Ten guys spanking me with ten hard swats each did the trick and I was told to stand and look over my shoulder to see what a good job they'd done.

"Nice and evenly spread out, wouldn't you say?" remarked Fred. " And so rosy. Your butt cheeks are even redder than the cheeks on your face, Vic." They all laughed at that. And while I did have tears welling in my eyes, I didn't blubber like a little kid. For that I felt proud and suffered the soreness of my buttocks with pride. George had told me the initiation would take under an hour, so I felt like I was almost home free.

I was glad when Pete told me the strapping would come at the end of the pledge session to give my already sore buttocks a rest. He also assured me the three swats from each of the guys would not be done too hard... that is, unless I started to cry, because then they'd really go at it and blister my sorry butt. So I was determined more than ever to take it like a man.

The next part of the initiation was both instructive and enjoyable. George picked up one of my socks and shoved it under my nose telling me to sniff. They were clean socks and we'd only walked a couple of miles to the rec center that morning, so not much sweat stink in it. Then he told me this was a ‘before part’ of a ‘before-and-after’ sniff test. That's when Pete, Fred, George and the other seven guys surrounded me and each guy pulled down their pants zippers, adjusted their undies ( those who wore underpants, that is, ) and pulled out their stiffening hairy teen-junk. I was getting very anxious.

But no need to worry. This was to be my masturbation lesson, prior to my demonstrating my own ability to jerk-off and shoot a proper load. Pete jokingly called this 'the sock-it-to-me cum-rag' test. He went first taking my sock and inserting his hard cock inside. Then with one hand on his balls, his other hand rapidly stroked his cock for three minutes or so until he grunted and, breathing hard, shot a full load of cum into my sock.

All the other guys were stroking themselves too as Pete had been stroking away and cumming into my sock. That sock then was passed from one gang member to the next as they quickly made their smelly and sticky deposits. George was last to have a go ( or a come, I should say ) and when he was done he carefully handed the sock over to me.

"Now it's time to prove your manhood, Victor." declared Pete. " Like we just did, hold your balls in one hand and stroke your cock with the other until you add your essence to 'the sock-it-to-me cum-rag'."

It was so soggy and white slimy cum was seeping through the cotton material as I tried hard to get hard. After about two minutes of stroking I felt a stirring below like I'd never felt before. It must have been the great amount of lubrication that made this jerking-off so easy. At last, I went over the edge and had a really good cum. That's when things started to turn funny. Funny weird, not funny ha-ha.

My sock was slipped off my now shrinking penis by Fred who carefully rolled it up into a ball. As he was doing that, Pete and another guy grabbed my arms and pulled them behind my back. George had apparently already taken my shoelaces and tied them together and he now handed them to Pete who proceeded to use them to tie my wrists together. I was stark naked and bound with my hands behind my back.

And this was when 'the sock-it-to-me cum-rag' was turned into 'the sock-it-to-me cum-gag' as the rolled up cum-sopping wet drenched sock was shoved into my mouth. It was a tight fit and filled so much and was jammed so far in that I couldn't close my mouth. My balled up undies showed between my stretched lips and took up half my face. I breathed through my nose and with every trembling breath, swallowed a taste of cum as my jaw pinched the manhood juice out of my cum-gag.

The one thought that kept my hopes up was the fact that these guys had sworn to not tell anyone about what they were doing to me (I sure as hell wasn't going to talk) and that they had promised to give me back all my clothes and I'd be allowed to wear them on my walk back home. I was being humiliated now, but my initiation was almost over and no one else would know about it. Then I remembered the strapping that I was to get. "No tears, NO TEARS!" I screamed in my head.

Two lads held me in front with me bent at the waist as they braced my shoulders. Pete had me arch my back to better offer my bare butt as strapping target. They took turns, three swats each and they were good to their word as to harshness of their swings and I kept my word by stifling my sobs, aided by a mouth full of cum-soaked sock.

"Almost time for you to dressed, Vic." grinned Fred, who nodded to his mates who, once again, unzipped and pulled out their hairy man-packages. " But first we have to mark our gang territory on them before you can wear them. Sort of like having an official uniform dis-STINK-ly from us to you."

They all laughed at that. But I was confused. Could these guys actually cum again after just doing it only a few minutes ago? But it wasn't jerking off they doing; it was pissing. Ten guys stood around my pile of clothes and pissed on it making sure every bit of clothing was drenched and stinking.

"Now," smiled Pete, " it's time we dress you for your journey home. We're keeping our word here, Vic. All your clothes go on you, but not exactly as you normally wear them. "

My hands were tied behind my back so, they explained, they would have to dress me. My underpants were yanked up, followed by my shorts. They stank. My sneakers were put on my feet and felt damp and loose without the laces. My t-shirt did not go over my shoulders and cover my chest; instead, by feet were placed in the armholes and the rest of the shirt was rolled into a thin cylinder which was then tightly tied by some wrapping cord. The effect of this shirt binding was to restrict my foot movement to a stride only as big as half my shoulder length. I could only inch my way forward, at most, ten inches at a time. I was clothed but only partly covered and my two-mile walk home would be slow, stinky and would take a very long time!

That was when they pulled my pants down. As my brother, George was given the honor of stripping me. My khaki shorts and underpants were pulled down to my ankles and stopped there as the bondage t-shirt blocked the way. So now each step would be essentially in the nude, less than a foot stride per step and now, with my shorts and undies down, my lower calves and ankles would be chaffing. But the really embarrassing part of my attire was how I was made to wear my leather belt.

Not around my waist, of course. Instead my butt cheeks were parted and the belt was doubled up, greased up with drops of baby oil they'd brought and then slowly shoved up my ass hole until half was in and half was out. My other sock, the one not cum-soaked and gagging my mouth, was then wrapped around the end of the belt sticking out of my buttocks. It looked like a skunk tail which was appropriate seeing I smelled like a punked-skunk.

They each gave me a parting swat and pushed me out into the parking lot to send me on my way. But I was not going to be walking home alone. My brother and a few of the other guys had arranged to have lots of girls from my class and several upper grade high school girls on hand waiting for my appearance. To add injury to insult and humiliation, those girls were each armed with belts, jumping ropes and rolled up comic books and they used them on my already sore butt as they giggled and swatted me all the way home.

But I had to admit, the gang had kept their word: I got to wear all my clothes home and they didn't tell anyone what had happened that morning behind the dumpster in the back of the recreation center. But those girls had not sworn to any such secrecy and, while they didn't see what had gone on before they arrived, my piss smell, cum-breath, shining red butt cheeks and naked and bound condition gave them plenty of information to make up some really juicy gossip.

Oh, well.

(End of File)