Eventually I found Brian sitting by himself when I arrived at IB English and I went and sat beside him. After the class got underway and the teacher and students were adequately busy discussing one of the many books we had to read before the exam, I reached over and wrote in Brian's notebook "when can I come over next?"
"Why would you want to come over," he wrote under my comment.
"For some Jello," I said, using the same euphemism I had used the last time.
He wrote "huh?"
I looked at him but he was ignoring me and feigning interest in the class discussion.
Realizing he was waiting for me to spell it out so as to humiliate myself I gave in and wrote "so you can fuck me."
"You are saying you want me to fuck you?" "Yes" "Why?" "Because I like having your big cock in my ass," I wrote. "Are you a fag?" he wrote.
I didn't know how to respond. I had never given any thought to my orientation. In a boarding school the worst thing to be called was a fag.
Yes, I was pretty much only interested in boys. I jacked off thinking about them. I had sucked them and now found myself liking being fucked. I guess I was a fag.
So, after struggling with it for a few minutes I finally wrote in his notebook "Yes." "Write it in full," he wrote underneath.
"I am a fag."
"You aren't just any fag are you," we wrote.
"No," I wrote. "I am your fag." "Why?" "Because I love your big cock." "And?" "And I love your body and I worship you," I wrote, being truthful but also humiliating myself in the process.
He didn't write anything for the longest while.
Class ended and I figured I had been rejected again and that this was all about humiliating me as payback for my trying to tell boys in our class Brian had grabbed Wayne's crotch one time, trying to deflect my feelings for him.
I hung my head and was shuffling back from the girl's school to our school when he brushed by me, seeming to bump into me.
When I got back at school and was changing for sports, I realized there was a piece of paper in my pocket. I pulled it out and headed to the bathroom to read it in the stall so no one could read over my shoulder.
"Skip sports. Be at my house at 4:45, let yourself in, attic, strip naked, wait for me."
It was already 4:40 so I ran to my locker, ripped off the rest of my clothes and threw on my gym kit and ran all the way to Brian's house, letting myself in, bounding up the stairs to the attic where I stripped off all my clothes.
Brian was not there so, after a while, I sat down on the couch, still naked, and waited.
An hour must have passed, and then I heard someone downstairs. I thought it might be Brian but they didn't come upstairs. That made me nervous. What if it was his brother, or worse, his mother? How would I explain I was in the house, let alone naked.
But I still sat there on the couch naked and waited for Brian. If I was caught I was screwed, but if I put on my clothes I risked offending Brian and that would mean we would never have sex again.
So I sat there quietly and eventually I heard talking downstairs and then Brian came upstairs.
I breathed a sigh of relief but the look on his face was not happy.
"Did my note say you could sit," he said sternly.
"Um, no," I stuttered and got to my feet, my hands in front of my crotch.
"What are you doing," he asked.
"Um, standing as you wanted," I replied nervously.
"Put your hands at your side," he barked which I quickly did.
Brian laughed at me and said "you are a sorry excuse for a fag," then added "and you don't follow orders. Get out."
Chastened I put on my gym kit and went downstairs. I passed Brian's younger brother who was lying on his bed and who looked at me curiously, not having seen me come in. I quickly ran out of the house and back to school.
For the next couple weeks Brian again made a point of sitting between people in our English class so I could only look over at him and, I admit it, from across the classroom I couldn't help but keep staring at the front of his dress slacks and picturing that big cock under them. And I did the same during gym and sports when he was changing, looking over every chance I could to see him in various states of undress to get a glimpse of that large cock. No matter what colour and style of briefs he wore, he filled them out so well and they all added to his long, slim and semi-muscular physique.
Finally on a Tuesday's English class I arrived and he was sitting alone. I sat next to him. When the class was underway I wrote in his notebook "give me another chance."
"This Saturday afternoon at 2pm prompt, let yourself in as you were supposed to," he wrote. "Don't touch yourself in the meantime."
This was a long weekend so there were few people at the school so it would be easy to sneak off to Brian's in an afternoon. On long weekends there are only a handful of boys left in the school (most go home or get invited to a day-boy's house) so they move the handful of us left at the school into the top floor (where the grade 13 boarders are housed). That way one teacher and prefect are all that is required to keep an easy eye on our coming and going. But it meant that younger boys (grade 9-11) who I wasn't used to showering with were suddenly showering with me.
The time until Saturday was excruciating. The anticipation was driving me wild. But worse were the showers and sports.
Every morning, prior to Brian telling me not to touch myself, I would usually jack off my morning wood as my roommate was taking a shower and then I would take my shower without fear of getting a hard-on. Even then I would need to jack off again at night to get to sleep. Four days of not touching myself and I was so wired. I tried not to look at boys in the shower or to think about Brian but the more I tried the more I thought about them and the more I got boners.
Then when Friday came and all the boys who weren't going away for the weekend moved onto the top flat it became worse. Suddenly there were one or two boys from grade 9, 10 and 11 in the shower and I couldn't not look. I literally ran out of the shower when I felt a chubby coming on, whether or not I was dry, had cleaned the soap off or had finished peeing if I was just in the bathroom to pee and one of them was under the shower head (which was open to the bathroom). The same was true for Saturday morning (boys either shower in the morning when they got up or at night before they went to bed, it was a personal choice, so pretty much whenever you used the bathroom to brush your teeth, pee or shower yourself there was someone else taking a shower).
Finally Saturday afternoon came and I let myself into Brian's house and went up in the attic. This time Brian was there sitting on the couch, wearing jeans and a tight white t-shirt (normally we aren't allowed to wear jeans or t-shirts, even on evenings and weekends) and these accentuated his slim hips and wide shoulders. He was watching TV.
He didn't take his eyes off the TV and after I waited for a few minutes and he said nothing I removed my beige corduroy pants (I didn't even own jeans), polo shirt, socks and green briefs (having switch to colour briefs in case they got noticeable stains in the back). I kept my hands at my side and stood at attention but being so nervous, in spite of not having jacked in four days, I was soft.
Brian looked over at me and then said "I don't want to look at your tiny flaccid cock," and got up and went downstairs. He came back carrying a jock strap.
"My jocks would be way too big for you," he said as he flung it at me. "This my 14 year old cousin left, it should fit your small cock fine."
I put it on and while it, sadly, did cover all of my small cock in its soft state, the waistband and leg straps were so tight I was afraid I would lose circulation. Brian didn't seem to care.
"So what are we going to do about the fact that you didn't follow my orders last time," he asked.
"I thought your making me wait until today was my punishment," I said sheepishly.
"Hardly," he snorted. "You have to learn who is in charge."
With that he patted his lap. It took a second but then I realized he wanted me to lie over his lap and he was planning on spanking me. I had never been spanked as a kid, my parents being big on punishments like time outs and loss of privileges. So I had no idea what to expect, but I did as commanded and bent over his knees in the tight jock strap.
Brian ran his hand over my butt cheeks before raising his hand and slapping down hard. I couldn't see but I could feel the red mark where his hand had made contact.
Brian looked at his handiwork and let out a whistle and a "nice!"
He then set to work in all earnestness and slapped my ass repeatedly until I imagine it was a solid red. It certainly stung and I could feel the heat emanating off of it.
"Get up and turn around," he said.
I stood and turned so my back was to him and he ran his hand over my hot red ass cheeks, admiring what he had done and repeatedly muttering things like "nice", "so uniform red" and "work of art".
My ass was red and sore but I realized my cock was rock hard in the small jock. He must have been curious about this too, because he told me to turn around. When I did, I knew he could see what I had just realized, I had liked the spanking and I had a hard-on under the jockstrap (which even more embarrassingly still covered my entire cock and balls even though it belonged to a 14yo and I was 17).
Brian laughed and said "suck me off."
I dropped to my knees between his legs and undid his jeans and took his cock out of his pants and underwear (he was wearing white briefs today).
"Take them off me," he ordered.
I pulled off his jeans, his socks, his t-shirt and then his white briefs, then got back between his legs on my knees and began to work on his cock, first slowly on the head and shaft with my tongue and then began to deep throat him.
He put his arms behind his head (locking fingers at his neck) and just sat on the couch and watched me work his cock for a while.
"Lotion is next to my bed," he finally said and I jumped up and ran into his bedroom, my red ass framed by the white jock no doubt wagging behind me as I ran, and returned with the lotion which I handed to him.
He put some on his cock and then reached behind me and put some on my hole. It felt freezing cold against my red hot ass where his hand brushed against my spanked ass cheeks on the way between the crack where he pushed an ample amount into my hole.
He then moved me around so I was standing in front of him facing away, and pulled me down so I was backing up and lowering myself onto his cock. I sat down on his cock and he put his hands on my shoulders and pushed me down as his big cock slid into me.
It hurt, but not like the last time as I knew what to expect, and soon I was sitting down on his lap.
Brian reached for the remote and before I knew it a straight porno was playing and it was cured up to a scene where a woman was in the exact same position I was in, riding some man. Brian clearly had planned to do me this way before I had ever arrived, and the fact that he did and it turns out he had every right to expect he would, I strangely took as flattering and not insulting.
In fact, I took the cue from the porno and I began to ride up and down on Brian's cock in time to here riding her co-pornstar. As I looked at the size of the cock going into her I realized Brian's had to be bigger and I smiled to myself. Sure Brian was using my ass to get himself off and watching str8 porn to do it, but I had his cock in my ass and it was bigger than what she was taking.
I reached between my legs and began to play with Brian's balls and feel where his cock disappeared into my ass and he slapped me across the back of the head and said "do only what she does."
So I resumed mimicking her movements riding up and down on Brian's cock as she did her co-star.
Eventually Brian's fingers dug into my shoulders and he pushed down hard, and I could feel him explode inside my ass. I kept moving like the woman in the movie but with each upward movement he pulled me down hard and shot another thick load into my ass.
After what must have been six or seven good ejaculations he let go of my shoulders and I lifted off his cock, feeling it exit my ass with what had now become a little feeling of sadness at losing what I now was thinking was a part of me.
I started to move to get my clothes and Brian said "come back here."
I walked back to him and he reached out and touched the pouch of his cousin's jock strap. Sure enough, I had cum in it while I had been riding him which is what he was checking to see. In fact, I had cum so much (I wasn't even sure when I started cumming and when I stopped but I knew I had unloaded a lot into that small pouch) that it was sopping wet. He then turned me around and gave my ass a couple new slaps to bring the red back into its original brightness post-spanking.
"I want you wearing that jock for the next week until you come to my place the same time next Saturday," Brian said.
"And I want you to take a shower tonight before you go to sleep," he added, knowing that someone would see my red ass and maybe guess I had been spanked. "And no jacking off, unless you do it into the jock which you will keep on after you cum even when you go to bed."
I just nodded obediently.
When I got to school I stood against the soft drink vending machine until dinner to make the redness of my ass go down. I kept the jock on until it was time to shower and then took it off under a towel in my bedroom before going to the shower. When I got to the shower there was only Robert under one of the nozzles. Robert was in grade 9 and we were friends because when I became a boarder I ended up having to eat with the junior school because there were no seats left in the dining room and he was the monitor at the head of the table.
I could tell, because he kept looking over at my ass, that he saw the redness (hopefully he couldn't see handprints). Robert was my friend so he would be bold enough to ask what the redness was but he was only in grade 9 so I was hoping he wouldn't guess (what grade 9 thinks of spanking as a normal part of sex). As it was, he didn't say anything at the time and I avoided him and everyone else for the rest of the long weekend.
Not only was I worried that Robert would ask questions, or that maybe I would show signed of having been spanked and fucked (maybe in the way I walked or sat) but that I smelled. I could smell the cum soaked jock myself through my clothes.
By Sunday the redness had gone away and by my Monday morning shower no one was the wiser that I had been spanked and fucked. Though I still wondered what Robert thought.
As the week went on I did as I was told and wore the jock under my clothes and to bed at night. I didn't change for sports and gym in the locker-room. I convinced the gym teacher that I be allowed to change upstairs in the residences so I could take a shower after sports and he agreed. So I would change into my gym kit in my room and after gym change out of it and take off the jock and shower before putting the jock back on and donning my school uniform.
As night I would, as soon as my roommate was out of the room, rip off my clothes and jump into my bed wearing the jock so I was under the covers before he got back to the room. That meant going to bed whenever the opportunity presented itself, so from 9pm on my evening was all about waiting for him to be out of the room for a few minutes.
Between the smell of the jock and its tightness, the only thing I could think of during class all week long was me in that small jockstrap.
I tried not to jack off because as it was the jock strap reeked of cum. But by Wednesday I couldn't last anymore and so I would lie there in bed (having jumped in bed as soon as my roommate was out of the room) and wait for him to fall asleep and then jack off while wearing that jock, filling that pouch with fresh cum every night.
I was convinced by the end of the week that everyone could smell my jock, and I tried where possible to sit by myself in all of my classes. I also realized that given how tight the jock was, that anyone who looked at my ass in my dress pants or gym shorts would have seen the lines where the strap dug into my legs.
I was convinced, as I walked through the school, that everyone knew I was wearing a cum caked jock strap that was too small for me, and that they knew I was the fag I was becoming.
The only thing that kept me going was that I had Saturday to look forward to. I guess part hoped Brian's test would be over and I would be able to take off this jock. But the biggest part of my hoped that I would get to suck on and ride Brian's big cock again.
I knew I would do anything for that boy. Hell, I had gotten a hard-on when he, a boy a year younger than me, had spanked me and ordered me around, and I jacked off every night remembering all of it: from his command of me to his using my ass to get off while watching str8 porn. And all I wanted was more.
I was now completely Brian's bitch.
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