As had become my practice I was in front of Brian's house before 2, but waited until my watch hit 2 before letting myself in and climbing the two flights of stairs to the attic. Brian was not there but I knew what was expected of me so I stripped down to the jockstrap and stood in the middle of the TV room with my hands on my head. This time I had the butt plug in my ass.
Eventually Brian came upstairs.
When he came over to me he reached out and touched the pouch of my jock. Then he pulled out the front and looked inside. I didn't have to glance down to know it was still soaking wet and filled with fresh cum from that morning.
"Why is your jock filled with cum," Brian asked angrily, the mistrust noticeable in his voice. So upset was he that he didn't comment about my puny cock (which was probably smaller than usually as nervous as I was at having displeased him), something he never missed an opportunity to do.
Quickly I explained that I hadn't been able to jack off all week because of the butt plug in my ass (which made him noticeably relax and even start to smirk which I took as a good sign). I went on to tell him that Robert had taken me into the last bathroom stall in the senior school locker-room that morning to fuck my mouth, which I described in detail (probably too much detail as I was sad that Robert had treated me that way and the fact that Robert and I no longer having romantic touching but had evolved into rather rough sex like Rob bragged about having with his female "sluts").
I don't know if I expected sympathy for the fact that Robert was no longer being romantic and not only fucked my mouth but had further degraded me by shooting his load on my face. Whatever I expected I didn't expect Brian to burst out laughing when I told him I had cum without touching myself when Rob shot his load not down my throat but all over my face.
"Guess your boyfriend has finally realized that you are only good for one thing and that is being a cum dump," he said. "Guess he is growing up."
I turned bright red and felt a pang of anger that the idea of romantic sex was juvenile. That quickly dissipated when I realized that he was probably right on two levels: that romance is the idea of children's fairytales and that for me I was far more turned on by being used (as evidenced by the amount of cum I had shot into my jock that morning in response to being face fucked and cum on).
I didn't have a lot of time to reflect as Brian moved behind me and knelt down and opened my ass cheeks to inspect my hole.
"You are keeping the butt plug in, good boy," he said. "Was it in while he fucked your face?"
"Yes sir," I answered.
I hoped he didn't ask if I took it out after I came as my stretching the rules by douching myself afterwards as justification for removing it would probably not meet with his approval. But he didn't.
Brian removed the butt plug and began to explore my hole. While I was nervous how clean I was, having douched in the morning and not right before I came over, that subsided when I glanced back at the butt plug lying on the floor and saw it was clean and when Brian didn't comment but simply continued with his examination of my ass.
Brian began to test my hole's tightness with one finger of his right hand and then two.
'Well you haven't let anyone fuck you," Brian said.
"I haven't sir," I responded eagerly, hoping that he would take that as a good sign.
"What is that lilt in your voice, fag," he snapped.
"I was just hoping? errrr?. that maybe?," my voice stammered and began to quiver as I realized I had shot any chance of him fucking me today (if there had been any chance in the first place).
"I am nowhere close to forgiving you boy," he said with contempt. "It will be a long time before you get my cock in this ass?
It was as if he could read my mind which I guess wasn't hard to do me standing there in a cum soaked jock with two of his fingers in my ass.
"If you ever will again!" he sneered.
What? It was still possible I would never get it inside me again?
I stole a glance back at his lap as he knelt behind me and thought I could make out his big cock which, while soft, seemed to be noticeable snaking down the inside of his jeans along his thigh for a good six inches.
Just looking at the front of his pants (something I knew I was not allowed to do when standing in my jock with my hands on his head waiting to be used) combined with trying to make out the outline of his cock made my cock harden in my jock.
God I was a horny slut.
I wanted Brian so badly I would do anything for that cock.
"Go get the lube," he said as he withdrew his fingers from my ass.
What did he need the lube for if he wasn't going to fuck me I wondered?
But mine was not to question, especially if I wanted to earn his trust and be rewarded with that cock in my ass ever again. So I ran to the bedroom and got the lube and returned.
Brian was still kneeling on the floor fully dressed and it looked like his cock, which ran down his inseam had lengthened which made my already hard cock twitch in my too tight jock.
I handed the lube to him and then resumed the position of my hands on my head, legs spread in front of him.
Brian began lubing his fingers.
I began to panic. He had shoved three fingers in my ass last Saturday and beaten my ass and that had been without lube. This time he felt he needed lube!
Strangely my cock did not soften in my jock as panic ran through my mind.
Brian began fingering my ass again, this time more roughly.
First he shoved the same finger of his right hand that had been in me before back inside me and moved it around.
Then he used two fingers and twisted them in a circle. While he had had two fingers in my ass just a few second earlier, the twisting motion came without warning, so it hurt, and I involuntarily let out a gasp. This earned me a slap on my left ass cheek with his left hand which had been holding my cheeks apart, causing my ass to clamp down on his two fingers.
Taking the two fingers out he shoved three fingers in without bothering to spread my cheeks and while this time I didn't gasp I still made an intake of air in surprise and this earned me ten slaps on each cheek with had left hand as the three fingers of his right hand were kept immobile deep inside my ass.
Removing his fingers he applied lube to four of the same hand and began to force them into my hole without spreading my cheeks.
I had taken Brian's cock up my ass now a number of times and it had to be about the same width as the four fingers he was shoving into me now but this was much more painful.
The slut that I am, a cock felt natural in my ass, but these fingers were in stark contrast to the pliable flesh of a penis - of his penis (because, let's be honest, that is the only penis I wanted; and needed in my ass constantly if he would put it in and keep it in there).
His fingers were boney. While he had given my ass a pounding with his cock repeatedly his fingers had the full force of his considerably arm muscle behind them and this hurt way more.
Once he had the four fingers inside me as far as they would go, he did like the previous week with three and began to stretch them apart, pushing against my anus on the inside.
This hurt even more, but I bit my tongue and made no noise.
I tried to think of his penis. I wanted his cock inside me and I was willing to do anything.
I stole a backward glance at his jeans and I was sure his trouser snake was now longer running down his thigh.
Trying to not be obvious with my backward glances I focused on his penis. I tried to picture it inside me and kept saying to myself these four fingers were the same thickness as that cock I could see through the denim.
But they weren't the same. He wasn't hitting my prostate with the head of his cock (which brought me so much pleasure) and they were opening and closing inside my ass (while he could stretch them apart only a few millimetres each time it was not anything like his cock pulsing inside my ass as it unloaded its cum deep inside me).
Brian then began to spank my ass, repeatedly on each cheek with his left hand as he held the four fingers of his right in my hole.
After a while (what seemed like an eternity) he stopped spanking my ass.
I could feel how red it was.
Brian then began to move his four fingers in and out of my ass.
In spite of myself I found myself getting hard again in my jock (I had not gone entirely soft but I had lost some of my erection from the pain).
The more he shoved his fingers into me the harder I got and before long I was panting as he fucked me with his right hand.
At first I was rising up on my toes as he shoved his fingers up into me? but before long I was staying put? and then before long I was even pushing back against his fingers as he shoved them into me.
To my surprise, I found myself so turned on by this assault on my ass from his hand.
Damn, the bottom I was, I felt myself coming close to orgasm simply by him finger fucking me.
I guess he realized I was close because then he stopped and removed his fingers from my ass.
I was disappointed?
No that is an understatement, I was crestfallen.
While I desperately wanted him to fuck me and his fingers were a pale substitute for that mammoth cock that I could make out in his jeans and which had worked my ass and my mind so fabulously before I was enjoying him finger fucking me and I was so damn close.
"Get dressed and get out," Brain said as he rose to his feet, and then left the room.
I was so close! Damnit!!
I thought about reaching into my jock and giving my cock the probably two strokes I needed to make myself cum but I daren't? plus it wouldn't have been as satisfying as cumming from him working my ass with his fingers (and nothing was as satisfying as his working my ass with his cock and I wasn't going to put that in jeopardy).
I looked down at the butt plug.
He hadn't said if he wanted me to wear that again.
He hadn't said not to, so I put it in my hole.
Part of me hoped that shoving it in might make me cum, so I shoved it in as hard as I could, but it was nowhere close to the size of four fingers (and I guess that moment where I could be pushed over the top into an orgasm from something in my ass had passed).
Putting on my clothes I left his house and walked back to school.
I could feel my hole was stretched and I kept squeezing and relaxing my ass muscles on the butt plug as I walked.
I wanted his fingers in me.
I wanted his cock in me.
Squeezing my ass tight around the butt plug, not even seeming to care that both my ass cheeks were sore from the slaps they had endured, I desperately wanted Brian to do more to my hole.
How would I last until next Saturday?
What if he never made me cum again?
I needed Brian to work my ass somehow to make me cum. Please, if there is a God, convince Brian to make me cum next week!
Who am I kidding, Brian is my God. Please Brian make me cum next week I prayed in my mind as I walked into the school, a butt plug in my ass, my ass sore from being slapped and a tight damp jockstrap constraining what was still had hard-on I had from bring finger fucked with FOUR fingers.
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