I arrived at Brian's before 2pm, having douched myself in the senior school locker-room bathroom as expected. I let myself in and climbed the two flights, stripped to my jockstrap and stood in the TV room, legs spread, with my hands on my head.
I was nervous because I knew I had betrayed Brian and worse, I had no idea how to stop Christopher blackmailing me again, and part of me even liked Chris fucking me!
The guilt built every second I stood there wearing only a jock waiting for Brian's big cock which I had to have regularly inside me to feel complete.
I had thought I had experienced stress when I first starting wearing a cum soaked jockstrap (that was way too tight) day and night in my boarding school.
I was now a nervous wreck. Between the sneaking out of school on Wednesday night to let Chris fuck me, avoiding and then being confronted and then used by Robert, and now waiting for the hammer to fall with Brian I was sure I was going to develop an ulcer.
I loved Brian's big cock and I worshiped his body. His slim tall smooth body and that cock that was bigger than any I had ever seen!
Brian knew he was hot and knew from the locker-room, as I did, that he was better endowed than any boy younger or older than him in our school and that, excuse the pun, cockiness, made him even hotter in my eyes. I couldn't wait for him to arrive and fuck me; and I couldn't imagine that not being part of my week.
While I lusted after Brian 24/7, part of me felt I was in love with Robert. While I was not happy that Robert had used me like one of his female sluts that morning, I desperately wanted to have a relationship with Robert even though he was only in grade 9.
I missed the Robert who had kissed me and held my hand in the park and been romantic and reciprocal in showing his affection. I missed the little things like him being in his briefs in his room as he got ready for bed and having his little hand down my pants and sliding my hand down his when we were alone.
I had fantasized about Robert fucking me the way Chris had at the outset, with my legs on his shoulders looking up at him, and I desperately wanted to try that with him, though I also didn't want to jeopardize things with Brian to get that - which only drove home the fact that I had already put everything with Brian at risk, and for what? To prevent Chris from outing me to his parents or mine or the school.
If I had to admit it, I had been excited to let Chris fuck me and had cum on his sheets while he finished himself off using my ass with me face down on his bed. While that was a far cry from the romantic lovemaking I thought I desired with Robert I did cum without touching my cock when I was turned face down on that bed.
Maybe I needed to be humiliated and used and not loved.
In fact, the more I thought about Chris fucking my ass on Wednesday night my cock hardened. How wrong was that? I didn't even like him as a person and, while I guess I know appreciated how his body was filling out and becoming toned, he was no Robert and definitely not a Brian.
And what about this morning? Rob had been angry with me and he didn't even know the extent of my betrayal. He probably thought I was with Brian on Wednesday night when I used him for an alibi, which I knew he tolerated because it was a 'relationship' (if you can call it that) that pre-dated him. If he ever found out I had let his classmate fuck me, someone new, and in defiance of the rules that prevented him from fuck me, he would probably never talk to me again.
Again to be honest, this morning when he was fucking my mouth in anger and I was crying all the way through it, I liked it and I even liked his shooting some of his load in my face.
But what would happen if Brian figured out I had let Chris fuck me? I couldn't imagine being cut off from Brian's cock. I felt empty when he wasn't inside me. Even when Chris fucked me I was aware of how small Chris' cock was in comparison with Brian's when it slid so easily in and when every thrust stopped short of connecting with my prostate. I liked Chris fucking me and feeling his boy cock slide in and out of my hole but I NEEDED Brian's cock to fill me completely and connect with my prostate. When I sat in class, reminded of Brian constantly by the tight jockstrap, I longed for Brian's cock being deep in my ass, filling me.
While everything felt like it was going wrong emotionally for me, with no one who cared about me - they all were just using me to get them off - and I never felt lonelier, I had to admit that I was never as sexually fulfilled as I was now that was getting cock in my mouth and in my ass regularly, even if I was living every day with the danger of being expelled by the school, or found out by my family and classmates as the bottom boy I so clearly had become.
Eventually, Brian came upstairs and by then my stomach was in knots and my legs were shaky, though my cock was leaking copious amounts of pre-cum.
Brian came to stand behind me and began to undo his pants.
While I had been a mess of contradictory emotions while I waited for this blond Adonis to arrive, the stress and worry began to fade as the excitement built in anticipation of Brian's big cock being shoved in my ass. It seemed he wasn't going to bend me over the couch but rather fuck me standing and that excited me further because it wouldn't be so rough and I could relish every inch of that mammoth penis as it filled me and lifted me off my feet with every thrust.
The head of Brian's cock connected with my hole and I steeled myself for his entry but no sooner did the head of his cock enter my hole then he pulled out.
Brian dropped to his knees behind me and spread my ass cheeks and was inspecting my hole.
I glanced behind me, as much as I dared as I was not to turn my head, and I could see him kneeling there with his hands on both my ass cheeks, his pants pushed down his thighs and his huge cock sticking straight up between them - that cock I had longed for all week and I desperately wanted inside me no matter how rough he wanted to fuck me.
While that cock looked so delicious, it was losing tumescence.
Why would Brian's hard cock be deflating as he inspected my ass? I had done a good job of douching, so I knew I was clean.
My heart began to sink.
He knew!
I don't know how he knew.
"Is there anything you want to tell me," Brian asked as his finger probed my hole.
He had to know. But how could he have?
What if I told him and he didn't know?
If I told him I wouldn't have to carry the burden of Chris' blackmail alone (and I knew I couldn't go through another evening like Wednesday of sneaking out of and then back into school). And I definitely couldn't deal with this guilt.
But the more likely scenario was that he would react angrily and at best I would be punished or worse I would never get his cock inside me.
I kept glancing behind me and his cock was now soft resting between his thighs, on his lowered pants and briefs. Even soft his cock was a sight to behold. But being soft and not hard just made me so sad and the depth of my betrayal to him and his cock seeped into my bones.
I blurted out "Chris made me let him fuck me, he said he would tell everyone, including my parents, that I was your bitch, that you were fucking me and making me wear this jockstrap." By now I was sobbing having given in to the guilt and thrown myself on his mercy - a mercy I knew he didn't have for me no matter how much pleasure he took from my ass.
Brian's hands had gone from gently inspecting my asshole to roughly manhandling me. He shoved his fingers in my hole, first one, then two and finally three, and probed and moved them around.
"Why do you think I only fuck you once a week," Brian demanded, his anger clearly rising.
"Because I can only get away from school once a week," I queried through my sobs.
"No," he said, as he unceremoniously shoved three fingers in and out of my ass a dozen times before leaving them firmly planted in my ass, "so you are tight for my cock!"
"I can get three fingers in easily barely stretching you," he spat out as he tried to spread those three fingers while inside my hole "why would I want this on my cock?"
"You aren't upset Chris fucked me," I asked through my sobs and the pain that he was inflicting on my ass, "its sob just that I am loose?"
With his three fingers still shoved inside me Brian used his other hand to slap my ass cheeks repeatedly, increasing my pain. This was the most rough he had been with me and while I knew I deserved it, I was not sure how much more I could take.
"Of course I am pissed that you broke my rules," Brian said. "For that you will be punished. And I will take care of Chris too. But I am more pissed that your hole is too loose to be of any use to me today."
"I am sorry," I sobbed again and again, as Brian kept slapping my ass cheeks with an intensity that was beyond the spanking he had given me over his knees. I would never forget how upset I had made him and I knew I would never do it again, even if that meant my parents and the entire school would learn I was his bitch, that I was wearing a cum soaked jock everyday to school as I dreamt and jacked off in memory and anticipation of his huge cock inside me (something that I equally knew may never happen again).
I stood there with Brian kneeling behind me slapping my ass, three fingers shoved deep in my hole for what must have been 30 minutes. My ass went from stinging to raw sore as he took out his anger on my cheeks.
I continued to cry out of shame over having betrayed him, more so than at the pain of having my ass beaten. I also continued to steal a glance backwards every so often to look at the object of my desire, his huge cock which was lying exposed between his thighs over his pants and briefs which he hadn't stopped to pull up being so intent on punishing that ass that had been used by another boy.
It was as if the cock was taunting me as it lay there, almost shouting at me 'you could have me inside you right now but instead you let that puny grade 9 inside you and I am left lying here unsatisfied and disgusted'.
The slaps began to slow, though I wasn't sure if that was because he had released his anger or his hand was getting tired or sore (my ass was beyond sore so his hand had to be hurting).
When the slaps stopped, Brian removed his three fingers from my ass, rose to his feet and pulled up his pants.
Seeing that cock be put away out of the corner of my eyes was so sad. I would not get fucked today by it, maybe ever again.
Brian headed to his bedroom, returning with the butt plug which he shoved into my ass.
"You will wear this 24/7, taking it out only to crap and during athletics," Brian said. "Clearly you cant be trusted".
I had no idea how I would pull that off without being caught or what it would be like having a plug in my ass outside of sex (the only times Brian had put it in my ass was when I was with Robert and I was so boned in those moments I enjoyed everything done to my body and a foreign object in my hole was not an intrusion but a pleasure). Now that I was soft this butt plug felt anything but pleasurable. It made me feel like I needed to run to the washroom and shit it out, but I nodded dutifully at my new orders.
I put on my clothes over my jockstrap and butt plug and left Brian's house. The sadness at having so noticeably upset Brian, at not having his cock inside me this week was pronounced and I continued to cry all the walk back to school.
My ass was so sore that it was Monday before the pain and redness had subsided. I made a point of showering when no one was in the bathroom. I didn't want anyone to see how red my ass was and as Brian had only said I could take it out for sports and to take a crap, I felt I had to leave the plug in while I showered.
Maybe it was a good thing my ass had been beaten so mercilessly because when the pain finally subsided I had gotten used to having the plug inside me all day and night.
Having the butt plug in my ass outside of sex was a new experience. While at first it felt like I need to take a dump constantly when I walked around, and when I sat it pushed into me, this feeling waned and before long it just felt sort of (but not completely) natural inside me.
I knew it was probably cheating, but from Monday on, once my ass was no longer red, I made a point of taking a dump before my shower so the plug would be out of my ass in the shower, and also showering after sports, rationalizing that I had taken the plug out for those two activities which were approved and not because I was naked in front of my school mates and could bear the humiliation of them seeing me with a plug in my ass.
When I wasn't in the shower or playing sports, having the plug in definitely changed the way I moved and I sat. I sat virtually motionless and I walked in much shorter steps to minimize its movement inside me. At first this was to lessen the discomfort of having a foreign object in my ass but once it became natural it served also to ensure I didn't get a hard-on.
There would have been no way I could have done sports with it inside me. I wondered how Brian had known that. Had he tried one? Surely not, he definitely was a top if he was gay at all (I suspected he was just a horny sadist who would end up getting married with three kids and all he and I did would be forgotten by him).
I don't know what Brian had said to Chris, if he had said anything. But Chris didn't not try to talk to me or even make eye contact that week.
I tried jacking off with the butt plug in my ass Monday night but as soon as I came I desperately wanted it out of my ass. I fought that feeling, as Brian hadn't given me permission. And it took me several hours to get comfortable with it being in my ass and to fall asleep that night. So I stopped jacking off altogether which, for me, was a hard thing to do.
I had no idea if Brian would ever fuck me again but I would do everything I could to return to being his Saturday fuck. Not jacking off and wearing a jockstrap and butt plug were small sacrifices to earn back that cock.
NOTE: Nifty needs donations to provide these stories. http://donate.nifty.org/donate.html