When I had just turned 13 years old and was about to begin grade 8, there was a big teachers' strike in Ontario [Canada]. My parents were both teachers and supported the strike. But my mom, being a mom, was concerned that the strike would cost me my school year, and she forced my father to put me in an all-boys private school.
I was a smart student and I had skipped a grade so I was age 12 going into grade 7 and, my birthday being late May, I was 13 when I was ready to start grade 8. Fortunately I hit puberty early so where boys my age still couldn't cum and had small cocks and balls in grade 7, mine had already dropped and so I was not noticeably different from the 13 year olds that were most of my class in grade 7.
Admittedly I hadn't seen a lot of cocks in grade 7 (some in boyscouts where we camped together). I was going to public school and in public school you only have gym class three times a week and boys, being shy, change quickly and no one ever showers at school. But that didn't stop me from checking out the boys in gym class and I jacked off at night picturing each of the 'hot ones' in their underwear.
With hindsight I was lucky to be a teenager in the 1970s when it came to the locker-room. Briefs were not only the norm, I don't think I ever saw a pair of boxers in the high school locker-room before I graduated in grade 13. Cut cocks was also the norm because Canada had bought into the US myth it was healthier and it was provided for free by universal health care (you now have to pay something like $500 for a circumcision so uncut cock is the norm in Canada leaving the US as the outlier).
The amazing thing about changing in the locker-room at this time is that every style of brief was unique and each boy, probably for 13 and 14 year olds because their mom picked a particular brand and colour she liked and would make it easy differentiate from their brother(s) when she did laundry, almost every boy in my school had their own underwear signature. I would lie in bed at night and jack off picturing Ian in his y-front white briefs (what he always wore in the locker-room) or Wally who also wore white y-fronts but his had blue piping around the fly or Greg who wore baby blue with the classic vertical fly opening but no second colour.
My underwear fetish, which I now realize I have, began there. But at age 13 it was jacking off thinking of hot boys and they were all in their underwear.
I rarely got to see their cocks at school at the time, even in private school, but I could make out a lot of detail from the outline their cock and balls made in their briefs, so when I jacked off at night I could picture not just the briefs but the shape of their cock and what it must be like compared to mine.
I didn't want to go to a private school, having seen the movie Tom Brown's School days right before my 13th birthday and there is a scene where he got the strap so I was terrified on my first day of being in an Edwardian penal institution, but once I started grade 8, I loved it.
The school uniform of grey flannel pants, green blazer (in the junior school, blue in the senior) and green or white shirt (white being required for certain school days like the end of year prize ceremony) also quickly entered my fetish world as I would jack off at night picturing my classmates in their clothes (the ones I couldn't picture in their underwear). Besides, having a uniform took the pressure off of trying to dress 'cool' (which being one of the poorer students as my parents were teachers would have been impossible). And the all-boys environment meant we had no pressure to impress girls and could be goofy roughhousing hyper-sexualized boys among our own kind.
Our interest in sex was heightened at ages 13 and 14, was openly shared; I don't think a recess went by when we didn't talk about sex. Some of the talk was about sex with girls, even though no one had any experience, or about penthouse and playboy which some of the cooler kids had seen, but mostly we talked about our own cocks and other boys cocks and about jacking off and frankly anything that was forbidden and intimate so we could bond when the teachers (or 'masters' as they were called) couldn't hear.
Even though I had skipped a year, I was still a good student and my placement test to get into Roxbury put me in the advanced grade 8 class (there were two classes at every grade, advanced and general, in the junior school).
The advanced class of junior school in grade 8 was taught by the junior school headmaster himself, and we felt special. Our classroom was at the top of the stairs outside of his office; and every day the students from every grade assembled on those stairs. Outside of his office there was the board with every student's name, for all of the junior school, with stars for achievement. And if you got in trouble you would be found sitting outside of his office waiting, yes it turns out to get the strap if it was for something serious (I never misbehaved - well at least not on school grounds - so I never got the strap).
We were literally the kings of the hill as the students in the advanced class of grade 8, the last year of junior school, and we had achieved that just as we had achieved puberty.
In our grade there were a small group of students who were made 'monitors'. This title meant they wore a special silver pin (it was actually rather elaborate with the title monitor that linked by chain to an second enameled school crest). In a school that forbid all jewelry, and definitely would have expelled a student for the more modern piercings; a school that required uniformity in a school uniform: it screamed uniqueness and being special.
Monitors had responsibilities the teachers, or masters, gave them over all the students in the junior school (like organizing the students, sitting at the head of each table in the dining room to ensure order at that table during lunch, or dinner and breakfast too if you were a boarder).
All the monitors in my class, which had most of them, had a particular look, though I didn't realize it at the time. They were all blond, slim and very good looking. Years later there were allegations that the junior school headmaster had molested a few of the student at a party he threw for the monitors one year and I don't know if that was true but looking back with hindsight all the monitors were definitely hot -- or at least they were hot based on what I now think is hotness.
I suppose it is possible that what I find attractive was defined at that moment in time and there is no inherent hotness. By each of these monitors being of a particular look and me looking up to them that may have set my taste in boys and young men. Then again, the look these boys have is what Hollywood also chooses for its movie stars (these boys could have substituted for a young Leonardo di Caprio, Max Thieriot or Alex Pettifer) so this idea of what constitutes hotness may not be unique to me (though I suppose Hollywood could be doing to the world what the headmaster's taste in boys did to me).
For me these boys who were blond and slim were gorgeous and as monitors the were special and should be looked up to, worshiped and treated as gods.
I am not blond and slim so that may also be another factor in wanted them (if not wanting to be them). I have brown hair. I am also not 'hot' but rather could be described as 'cute'. When I was pre-teen I was the type parents and total strangers pinched my cheeks. As I have gotten older I have concluded that it is better to be cute than hot, cause most hot boys only have specific years during which they are hot (and then they lose their looks), whereas I have been cute my entire life, but at age 13 that was not something I appreciated and admittedly it may also be crap.
The point is that I worshiped these boy monitors and their period of hotness (and if I am right that quality is fleeting) was at its peak in grade 8.
The power they had as a monitor and their good looks combined to give them a sense of self-confidence that only made them ten times hotter. For example, one of the monitors was a Danish boy (being a private school we had students from abroad who were boarders) and he sat in the back corner of our class next to the window and being cool he would lean back so only the back two legs of his chair touched the ground.
He was able to get away with that I assumed because he was cool. It suited him. With hindsight perhaps the headmaster was having the same thoughts as I was, and that was he looked hot in that position and with his chair tilted back that meant his legs were stretched out and the front of his grey flannels (and his package under them) was fully visible all class long. Shortly after stating grade 8 I lay in bed many nights jacking off thinking of the front of those pants and what might be under them in terms of cock and even underwear.
As Jay was a boarder that meant before and after sports he could go up to the flats (or dorms or residences as other people call them) to shower and change, so I never got to see him even in his briefs - and I envied the other boarders who got to see him in the showers and changing.
The junior school residence had a single communal shower, a big room which I understand had like a central tower with multiple nozzles that boys stood under facing each other - soap and water running over their bodies with the each occasionally checking each other out. I had no interest in most of the pre-pubescent boys in junior school, but that picture stuck in my mind and I contemplated where it would be worth leaving my home and becoming a boarder (if that had been an option).
In grade 8 I had started to sleep naked because during our many recess conversations about sex [and other personal things that I lump into sex but you might think is just teen banter] other boys had said they either slept in their briefs or naked since pyjamas (or PJs) were for 'kids'. Once this settled in I was going to sleep in my briefs, but I was already jacking off every night before I went to sleep, so instead of using a rag that mom could find I decided to use my underwear from that day to catch of clean-up my cum. So in grade 8 I began to sleep naked.
I imagined Jay slept naked too, but I also imagined he him in very skimpy briefs when he wasn't naked (at 13yo I didn't know European briefs tend to be low rise so he was probably in them, I just pictured him in very skimpy briefs based on is look, and those in my mind made his package look even bigger and I knew it was bigger than mine from the front of his flannels). Needless to say when I started grade 8, I jacked off most night thinking of him.
I pictured him in the hallway, in his briefs, having come out of his room when the younger kids were making noise, and shouting "lights out". And then going to the communal shower and stripping them off and showering with a couple other boys at showerheads across from him and they would look over at him cause he had a bigger cock and more pubes than him. His slim tapered body, the water running down his torso, I pictured his cock and balls beneath his pubes, his otherwise hairless body [by then I would be seriously stroking]. I didn't know that Europeans are mostly uncut or I would have pictured that, but mostly my mind would go back to him in the hallway and picture him in skimpy off-white briefs standing there being commanding [at which point I would cum on my dirty underwear that was spread over my stomach to catch the mess].
While I couldn't help but jack off over Jay from the first day of class [because he was clearly the hottest boy in the school and he knew it], he was not the object of my affection in grade 8; and the subject of most of my jack off sessions. That quickly became Tony.
I don't know who was more gorgeous, Jay or Tony. They were both blond. At 14 years old you can't really define bodies but Tony was beginning to develop a swimmer's build so his shoulders were starting to be bigger than his narrow hips whereas Jay was more European in that he was tall and lanky. Both were incredibly slim. Did I mention they were both blond.
I don't know if we can rely on the rumours about the headmaster or even his judgement about what is hot if he was as people claim, but Tony was made a monitor on day one (the idea behind monitor is these were respected and trusted students who could be given authority over other students, something that can only be determined over time). I joined the school when he did, but he was a monitor day one.
For my part, I thought both were gorgeous. Jay intimidated me due to his high fonzie-level of coolness (a thing in the 70s), but I had the most visuals to jack off with Tony. Our lockers were arranged alphabetically. So my locker was right next to Tony (my last name began with an H and his a G). I don't know what lead to my obsession as both were gorgeous and I had for the first half of the year jacked off thinking about each one but the time spring hit I was in love with Tony and jacked off thinking about him wearing only his blue (with white trim) briefs ever single night.
In addition to his unprecedented appointment in his first year as a monitor, Tony got a lot of attention from the headmaster. For some reason the headmaster called him 'Fred', which he explained at the time but it I didn't really because to us, his grade 8 classmates, he was a monitor and the headmaster had made him special by giving him a nickname.
The headmaster had given me a nickname too. He called me Max (my dad's name), even though my name was Bruce. I don't know why I got singled out (maybe because I was cute given what was alleged years later) but it made me feel special. And it also made me feel closer to Tony since we had been singled out for this attention.
Tony (or Anthony as I always called him at the time because I couldn't imagine this blond 14 year old Adonis being just a Tony) became the subject of most of my jack off sessions. I worshiped him.
We had sports every day after school and gym class during school time three times a week, so 16 times a week I was at my locker next to Anthony changing for or after sports.
Anthony was a 'day boy', which meant we lived in Ottawa and only came to the school during the day. Boarders called all day boys 'gay boys' because at this age everything involves sexual innuendo but I never heard anyone suggest anyone was actually gay. And, as I learned as went through senior school, the issue is not about sex but being effeminate which none of us were [or became, as all of the boys in this story went on to be straight fathers and husbands].
Anthony always wore dark navy blue briefs with a horizontal fly with white piping around the fly and, at night, I would go home and picture him in his briefs and jack off.
We were supposed to shower after gym, but most day boys, including myself, were too shy, so we never did (I am pretty sure the boarders did regularly when they went up to change).
My jacking off before the first snowfall of winter when I was in grade 8 had become Anthony that day changing, and my memories from the locker-room that day when I got to see him change in and out of kit and in and out of school uniform next to (twice on days we had gym),
While I was picturing his cock and balls in his briefs, I wasn't jacking off over his naked cock. It was about the way he filled in those briefs which was the only brand and colour I saw in the locker-room at the time so it came to define him. Navy blue briefs with a horizontal fly defined by white piping means Tony.
Then came a fateful day that would change my life!
On this day, after gym, I had changed into my school uniform and was standing at the urinal peeing. Anthony came up beside me to pee. I stared straight ahead as you were supposed to do, but out of my peripheral vision I saw him turn his head in my direction so I looked over and caught him glancing down at my cock.
As I mentioned, while I was only 13, I had gone through puberty early so I wasn't embarrassed at him looking so, after glancing behind to see that no one in the locker-room could see (the bathroom and the locker-room has no door, it's an all-boys school so nothing is designed for privacy), I moved my hand away from my side to let him see.
Once it became clear I was willing to let him see my cock, he did the same and moved his hand away from his cock so I could see his package. It was similar to mine, about 2 1/2" cut when soft, though he had more pubes than I did, which made sense since he was 14. I wondered if he would be that same as me hard, about 4 1/2".
I glanced back again to see if anyone was looking and when I determined no one was, I tried to reach over and touch it but he pushed my hand away. But he didn't do up his pants and walk away, he stayed at the urinal with his hand at his side so I could see his cock.
As he stood there his cock started to harden before my eyes, something that caused the same reaction with mine. Before long we were both hard and his looked bigger than mine, maybe an inch bigger and definitely thicker.
I tried reaching for it again, and again he pushed my hand away.
"Not here," he said. "McKay Lake."
At this point he shoved his boner into his grey flannel pants and did them up and walked away. I did likewise with a lump in my throat as big as the lump in my pants. My school books that I got from my locker were able to hide my erection which wouldn't seem to go away for the rest of the afternoon.
After school I made my way to McKay Lake, which was about a 15/20 minute walk from the school, so I had many doubts he would be there, but low and behold Anthony was sitting on a bench. When he saw me he got up and began to walk and I followed him until we were behind a structure that was built for Queen Elizabeth's silver jubilee which had trees behind it so it was isolated.
"No one comes here", he said as he leaned against one of the trees.
He was right, the building was shielded from view at the back by trees, and while the building was used for events occasionally, no one hung out there. Though to be honest, I didn't care at the time. I only reached out for is cock, and this time he did not push my hand away. He just leaned back against the small building.
I placed my hand on the front of his grey flannel trousers and found he was as hard as I was in mine. I undid his belt, opened his trousers and there was his hard cock pointing upwards in those navy blue briefs, framed on either side by the white piping. Instinctively I dropped to my knees, not caring that I was going to get the knees of my grey flannel trousers dirty.
I rubbed my face against the soft cotton of his underwear, feeling the heat of his erection against my cheek as I used my hands to pull his pants down his legs. I began to nibble, using my lips to feel up and down the shaft of his hard cock and then using my tongue to trace its outline.
My hands ran all over his underwear, feeling his ass, his balls, his hips and his hard cocks and I continued to work my mouth on it. He reached down to his briefs to peel them down and this time it was my turn to push his hands away. I had jacked off so often thinking of these briefs that now that I had him in them I wanted to savour the moment.
I knelt there licking and nibbling on his hard cock threw that soft blue cotton for so long the material was even a darker blue in the front when I was done. He was soaked from my drool.
Eventually he reached down, and this time I let him peel down his briefs, and as he did my mouth closed over his hard cock.
I had never touched, let alone sucked, another cock before and while I was more than familiar with my own, I was surprised at how it was simultaneously silky smooth and burning hot in my mouth.
While he was thicker and longer than me, I was able to get most of his 5 ?" cock into my 13 year old mouth. I held it my mouth for a few minutes, feeling so connected - like I was an extension of him. Before I let go I tried to burry my nose in his pubes but the extra length of hit cock made me gag so I went back to using my mouth.
My mouth loved having his cock it in it and I bobbed my head up and down as my tongue and my brain tried to map every inch of his cock.
Then I began to lick up and down his cock, stopping at the head and taking it into my mouth and running my tongue around it, then licking back down to the base.
Taking his cock in my hand and stroking it, I licked around his balls, taking each into my mouth.
"Suck me," he said, in a way that sounded half pleading and half commanding.
I immediately took his cock back into my mouth and began to suck, moving my head up and down so I would go from having only the head of his cock in my mouth to almost the entire shaft (as much as I could take without gagging).
Steadily I sucked him, my head bobbing up and down at a steady pace, one hand on his balls, the other up under his shirt feeling his smooth stomach and chest.
I could feel his stomach muscles and legs tighten as the excitement in him built and this made me go faster. So fast that it was a blur inside my head.
I knew he was close and the idea of not taking his cum in my mouth never entered my head. I wanted his cum. I wanted every load of cum he would be willing to give me.
I loved this boy. I had jacked off so many times thinking of him and now my hands were on his body and his hard dick was in my mouth.
He must have gone up on his toes because his cock seemed to go deeper in my mouth and then it happened, he began to shoot! My tongue against his shaft could feel it pulse as it sent shot after shot of hot cum into my mouth.
I swallowed as quick as I could, not wanting any to escape my mouth, and more kept cumming, most went down my throat and some dribbled out. Feeling his body relax as his cock stopped pulsing I knew he had finished unloading, but I didn't want to stop sucking on his cock.
Eventually he pushed me away from his cock.
I leaned forward again and licked up the cum I had lost.
He then pulled up his underwear and did up his trousers while I continued to kneel there staring at his softening cock, his blue under wear and his grey flannel crotch (the three things I had spent most of the year fixated on).
He mumbled "thanks"; and then left.
Staying kneeling I undid my own pants. My own white briefs were wet from precum. I took my cock out and stroked my cock. I relived what had just happened, including the taste of his sweet cum, in my head. It only took a couple strokes and I shot my load all over the dirt.
Putting my cock away I kicked dirt over what was a massive amount of cum I had produced. I then tried to clean my knees as best I could, but I knew I would get hell from mom for dirtying my trousers. I didn't care, I had just given head to the boy I worshiped. My only concern was whether he would let me do it again.
Then it struck me. My birthday was next week. Even if we never did it again, I had gotten the best 14yo birthday present ever!
Sure enough I got yelled at by my mom when my parents picked me up from school.
School ends with sports, which usually ends by 5 but occasionally it had been known to run late and end at 6 pm so they pick me up always at 6. Living in the south end of the city they had to drive me to and from the school and being teachers at different schools they also had to coordinate their own schedules (we only had one car being not particularly rich). So I was stuck at school until 6 each day.
Tony, on the other hand, lived near the school so he walked home and I learned from him the next day (in the one and only conversation we ever had about what we had done and what we were about to do). He was expected to come right home every day and usually that got him home at 5:15 and is family always ate dinner at 6. But his parents had signed up for bridge courses on Tuesdays so they wouldn't get home till around 6 on that night they would eat eat dinner at 6:30.
I was surprised to learn that this boy who I worshiped and knew was so 'cool' had any rules, but we were both 13/14, we went to a private school which is all about rules and I was terrified of upsetting my parents, so I got it. We had one window it was Tuesdays post sports before he had to get home before his parents.
We agreed that we would meet at McKay Lake right after sports every Tuesday. To solve the problem of my grey flannel pants, I proposed we go in our gym kit, which was green shorts and a white t-shirt and white socks with green stripes. The park, which is about 15 minutes from the school, was on his way home, so Tony didn't like the idea of going in kit, since that would mean going back to school and changing and then then trying to beat his parents home. The second he said that I was totally on board because more time sucking his cock was time well spent.
From that Tuesday, for the next six weeks (my birthday is mid-May and the school year ended in June), I would literally 'run' over to the McKay Lake in my gym kit: green shorts, white briefs underneath, white socks with green stripes, white t-shirt and running shoes. I would go to the spot behind the jubilee structure which is the partially wooded area of the park where we had done it the first time. Anthony would come sauntering in some time later in his green blazer (with his silver monitor's pin on the lapel) and grey flannel trousers.
When Tony arrived the first Tuesday he did the same as our first time and leaned against the building. I knelt before him and undid his belt and flannel pants and pushed them down to his ankles went to work on the front of his blue briefs, licking and nibbling the front, tracing the outline of his hard cock with my mouth. Licking the white piping. Licking around the balls.
We went through the same silent communication as the first time. He would go to push his briefs down and I would move his hands away and he would let me continue to play until it became unbearable as he wanted to cum at which point I would let him push them down and I would take and suck his cock.
But the following week, as I realized I would always be there before Tony I began, on my own with no suggestion from him, waiting for him next to the tree on my knees. When Anthony arrived he simply walked up and stood infont of me. I undid his pants and pushed them down and began to lick and sniff him with his briefs still on. My hands ran all over the parts of his body covered by his briefs, his ass, his balls, his hips and his cock, though mostly I worked his cock through his briefs with my mouth.
He let me do this for a very long time. Longer than ever before. And then, and I realized that for him he had decided it was time he had to cum, Anthony quietly reached down and put his thumbs in his brief waistband, pushed them down, and as he did I turned my head and lowered it onto his cock as he released it from his briefs.
I became so adept at it I don't think his cock was ever exposed to the outside air. As it emerged from his briefs it entered my mouth and from that moment on my head bobbed up and down on it until he shot his load into my mouth. He would then do up his pants and walk home. And I would take my cock out of my sports kit and jack myself off on the dirt in front of me, still kneeling.
At the beginning of June, realizing we wouldn't see each other over the summer, I began to keep his cum in my mouth. My head would be bobbing up and down on his cock, me kneeling in front of him in my kit and him standing there in his uniform with his monitor's pin (no longer leaning against the tree) in his school uniform with his pants and underwear around his ankles. When I sensed he was about to cum I sped up my bobbing on his cock but shortened my head movement so my mouth was closest to the head of his cock at all times and I was able to catch all of his cum in my mouth.
We never spoke so when Tony pulled up his pants he probably never knew I still has his entire load in my mouth. I stayed kneeling there in my kit, my cock tenting my green gym shorts, his entire load of cum in my mouth - and it was a big thick load (there was a reason the first time I felt the desperate need to swallow). I would jack off and as I came on the dirt in front of me I would swallow his load.
In the last Tuesday we were together, Anthony did something unexpected. I was on my knees in my kit as usual and he was standing in his school uniform, half uniform anyway cause his pants and briefs were at this ankles, and just as I began to notice the signs that he was going to cum he took hold of my head in both his hands and held it with the head of his cock just in my mouth.
He held me there tight and said "suck hard". We never spoke during these meetings and, while that surprised me, I was also his servant and he was my 'monitor' and I sucked on that cock head like it was a lollypop that we so close to the tootsie roll I needed to have it. Ever so gently he moved his hips and the head moved ever so slightly in my mouth.
I don't know why but as he did this I reach down with my left hand and began to touch his blue briefs that were down around his ankles. He held my head firmly and just moves his hips and thus his cock in and out of my mouth ever so slightly, and at the same time it stroked moved my fingers over the crotch of his briefs gently in rhythm. Suddenly he cock started to spurt and with only the head in my mouth I could feel every ejaculation and feel my mouth filling with his cum. Even after he had stopped cumming, he kept holding my head with his cock head.
There I knelt with a mouth full of cum, and this time ever single drop (none accidentally down my throat or over my lips) but, more importantly, his cock head. And he kept holding my head as his cock began to soft, moving ever so slightly towards me as it did so the head stayed in my mouth. Only when he was fully soft, which took several minutes, did he let go of my head.
As he moved to reach down for his underwear and pants his cock slipped out of my mouth and, bent over, he whispered in my ear the same word from the first time but this time not mumbled but firmly and, for me, dripping with emotion. |Thanks|
I stayed kneeling like that forever. I felt like his grapping my head had been a hug. Even though we had never spoken during sex (and rarely during school) he knew I had been keeping his cum in my mouth and wanted to give me an entire load. And he had done it in a way not trying to get him off (even though him being a monitor and me being on my knees in my gym kit I was clearly his bitch [a word I would later learn]) but so as to be generous to me.
I didn't jack off into the dirt as usual, I got up and walked back to school with his full load in my mouth and I kept it there as I changed out of my gym kit and into my school uniform and waited for my parents. It was only when I saw their car coming up the road to the school that I begrudgingly swallowed it.
It turns out that Anthony had convinced his parents to take him out of private school and put him in public school. On prize day, when I went to clean out my locker ,I found Anthony had stuffed in my locker a pair of his navy blue briefs and there was a very visible cum stain (cum really stands out on blue) where he had clearly jacked off at least once but based on the size I suspected multiple times as a present to remember him by.
Many nights I jacked off sniffing and licking those briefs.
He was my first love and without speaking he had come to know me (or maybe he had made me).
To this day, when I walk through a department store underwear section and see similar navy blue briefs with white piping I will start to get a hard on.