I did laundry on Sunday. The laundrymat was down the hill in the poorer area of town, so usually a group of us would go to laundry together. The group I usually went with included Robert and some of my younger friends as most of the friends I had made as a boarder were younger than me. I actually looked forward to doing laundry with them as I could check out their dirty briefs in their laundry pile when they weren't looking. Hell, I had even on a few occasions stolen a pair to sniff as I jacked off at night thinking about my friends' cocks and balls that filled them out as I inhaled the smell. I had even lucked out once and stolen a pair of dirty briefs from my friend Stephane that he must have jacked off into recently and I got to relive my night in the library with him in my mind (see Roxbury College story line).
But now that I had to wash my small dirty jockstrap I opted to sneak off and do laundry by myself. Besides, I had an additional task today and that was to purchase an enema. After doing laundry I returned my clean clothes to my room and set out for downtown. I chose a drugstore that was out of the way and after much searching I found where they kept the enemas. I grabbed that but also grabbed bandages, a package of tampons and a straight porn magazine. I guess I figured the salesperson would believe I was buying things for my parents or would be so distracted by an underage boy trying to buy a porn mag he wouldn't think twice about the enema, and it being straight porn he wouldn't possibly think the enema was for me. In the end the salesclerk didn't seem to even care what I was buying, so I wasted a lot of money for no reason.
My next mission was to talk to Brian about Robert.
I tried all week to get a moment with Brian alone but it was like he intentionally was avoiding me. Finally on Thursday I got to sit next to him in English class and, when no one was looking, I wrote in his notebook "David and his younger brother saw my ass last weekend and figured it out."
"Figured out what," wrote Brian who now seemed to relish my writing out the obvious.
"They I had been fucked," I wrote.
"Lots of people get fucked," Brian wrote being intentionally obtuse.
"Fucked in the ass," I wrote. "They saw the belt and zipper marks."
"Did they out you," he wrote.
"They seem to want me to service Robert," I wrote and then quickly added "but I told them I needed to check with you."
"So what do I tell Robert," I wrote.
"Just show-up Saturday," wrote Brian. "Did you get the enema."
"Yes," I wrote.
"Be clean and be on time," he wrote and then he closed his notebook so I couldn't write anything else.
Throughout the week I had done as I was instructed and I had the tight jockstrap on every day and night and as I was increasingly horny both because of Brian having fucked and dominated me and the prospect of maybe doing something with Rob I jacked off in the jock every night. I wanted to do it more but I was worried the wet stain on the jock would show through my pants so I just did it when my roommate went to sleep and during the day suffered with periodic hard-ons (which I discovered the tight jock would hide under my grey flannel dress trousers, or at least I thought it did and no one pointed out my frequent hard-ons).
On Saturday morning I went to the bathroom in the locker-room. As it was a Saturday no one goes into the locker-room unless there is a sports game against another school that is visiting, or at least I hoped, and I opened the enema box (which had been hidden in my underwear drawer all week) and read the instructions.
Filling it with warm water, I went into the last stall and locked the door. I stripped off all my clothes but the jockstrap (I felt obligated to wear that while I did this) and I put the hose in my ass. Filling myself with the warm water I then sat on the toilet and released.
I actually found it exhilarating and, without putting my clothes on, I left the stall in my jock and refilled the enema bag with more warm water and then returned and washed myself out again.
I realized as I was doing it how much of a bottom I had become at only 17 but I didn't care, I found just preparing to meet Brian by cleaning myself was very sexual. And I hoped like hell he was going to be willing to fuck me after all this work when I went to his place at 2pm.
Once I was sure I was clean, I put my clothes back on (thankful no one had come into the locker-room and caught me) and went upstairs. I stowed the enema bag in my bottom dresser drawer where I kept my underwear and left for downtown to kill time while I waited until 2pm.
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.
I don't know how much time passed. Unlike the previous times, I was not filled with panic at being caught by Brian's mom or brother. It hadn't happed to date and while I knew it was a possibility, I was where I was supposed to be and I just waited dutifully.
Eventually Brian came upstairs.
He walked over to me and knelt down and opened my ass cheeks to inspect my hole.
"Did you get an enema," he asked.
"Yes sir," I responded.
He shoved a finger into my hole and moved it around and pulled it out and inspected it.
"Good boy," he said.
Like the week before I could hear him undoing his pants and, instead of sending my for lotion I heard him spit. I realized I was going to only have his spit for lube.
Before I could think long about it, his cockhead was against my hole and he was shoving in. Lotion makes a big difference I discovered. With only spit it felt like his cock was tearing my hole as he forced his big tool into my hole unlubed.
I did not cry out or flinch, I just stood there as he kept pushing (and he had to push hard to get it into my without lube) until he was all the way inside. Again I could feel his belt and zipper against my ass and upper thigh.
It seems this was my new lot in life. Brian would bother to even push his pants down or get lotion. When I was there stripped to my jock willing to take his cock he would just undo his pants and shove into me.
Realizing how hard my cock was in my jock I had to admit I liked my new lot in life. This is where I deserved to be, where I wanted to be. I was Brian's bitch with my clean ass being filled by his mammoth cock, which deserved to be worshiped the way I wanted to and did in my mind every night I jacked off in my jock.
The first dozen strokes were excruciating without any lube beyond his spit, but before long it got better. I don't know if my ass was sweating or I was getting used to it but from feeling like he was tearing my anus apart it quickly transformed to my being able to feel far more intently the details of his cock as he slid in and out of me. I actually found myself preferring that he had only used spit because I could feel his cock so much better.
The digging in of his belt buckle and zipper still hurt when he thrust into me, and I missed feeling his balls against my ass, but I was his bitch boy and I was just lucky he was willing to put his cock in my ass.
Brian seemed even more than the previous week to just get this over with and he was quickly pounding my ass like there was no tomorrow. I knew it wouldn't take him long.
I knew it wouldn't take me long either, as I found myself loving him using me to just get off quick.
As Brian's breathing got quicker, mine did too. As his thrusts got more intense I could feel my orgasm approaching.
As Brian began to tense and shove in deep to shoot his first strands of cum I felt myself do the same into my jock.
Every thrust after that first spurt of cum, made me cum in my jock as he did the same deep in my ass.
I guess this is what in the porn mags they talked about the pleasure of cumming together but it was amazing. Each spurt he unloaded deep in my ass triggered my cock to explode. It was like his cum was forcing my cum out of me.
I also discovered that day I cum longer than Brian. When he pulled out of me, I was still cumming in my jock, and I stood there with my hands on my head experiencing my cock continuing to spasm inside my already soaked jockstrap.
While I was sad my ass was suddenly empty, I was still in the throes of my orgasm.
I was so consumed by my own feelings I didn't notice that Brian had gone into his bedroom and returned with something in his hand.
Once I returned to my own body and could focus my eyes, I looked at what Brian had in his hand and a quizzical expression must have appeared on my face. It was a small rubber object, too small to be a dildo.
"It's a butt plug," said Brian.
I am sure my eyes must have looked like saucers when he said that.
"Don't worry, you won't have to wear it all the time," Brian said as he moved in behind me and began to put it into my hole. It slid in easily, which is not surprising given the fact that he just had fucked me with something probably six times bigger.
Just then the doorbell went.
"That will be Robert," Brian said.
Brian, who had done up his pants, went down the stairs and I stood there with my hands on my head and this plug in my ass wondering what he and Robert could have possible discussed.
When Brian returned with Robert in tow, I braced myself for Robert to burst out laughing at the sight of me in a jock that I had so clearly cum in, the marks again on my ass he had seen the week before and now a plastic plug clearly visible between my ass cheeks.
But the look I got from Robert exuded sympathy. It was like he felt bad for me. Then again, he was here in Brian's house on a Saturday which is when I was now getting fucked so he had obviously agreed to participate in some fashion.
Before Brian could say anything Robert ventured "the only way Brian would let you do anything with me is if he could watch."
Brian clearly didn't appreciate the apologetic tone and snapped "your ass is my property which is why you have a plug in it" at which it turned bright red. I knew Robert knew what I had been up to and the way I looked left nothing to the imagination but for Brian to say it in front of him was humiliating.
Robert didn't seem fazed and turned to Brian and said "you just get to watch, you can't talk."
Brian seemed actually chastened.
I knew Brian had a thing for younger guys. He had always tried to strike up conversations with my friends, but they all gave him the cold shoulder. I never understood why none of them liked him. Maybe it was because he was not actually interested in them (what they were up to, how they were, what they were going through? actual friendship) and simply interested in being around them (cause I guess he found them hot).
So this must have been the deal Brian struck with Robert. Robert would have never fooled around with Brian but he would let Brian watch us. Plus Robert and I were boarders so fooling around at the boarding school was difficult (though not impossible) to do.
Robert took me by the hand and led me into Brian's bedroom.
When Robert had approached me the previous Saturday I had figured he just wanted to use my mouth and ass to get off the way he used his 'bitches' and the way Brian used me. But Robert clearly had something more in mind.
Robert quickly stripped and his hard cock made it clear that he was looking forward to what was about to transpire. He was about 6 1/2" cut, but the head of his cock was like a big mushroom. His blond pubes made that red cock head seem even more menacing. The rest of his compact body was entirely smooth.
Rob took off my jock, revealing my hard cock which was equally anticipating what was going to unfold. When he went to take out the butt plug Brain, who had taken a seat in a chair across from the bed, said "that stays in."
Taking my hand again, Robert lay down on the bed and pulled me so I was next to him. To my surprise he leaned into me and kissed me.
This was definitely not what I had expected from Robert. In my wildest dreams I had thought I would end up in a bathroom stall at school on my knees sucking his cock with him barely talking to me ever again once our relationship had changed to include sex.
As Robert gently kissed me and then opened his mouth, with me reciprocating, to French kiss me as his hands explored my body and I did the same with his. Before long our explorations with our hands had honed in on each other's cock and balls and, without having to say a word, we both moved so we were in a position so we could 69.
Taking the mushroom head in my mouth I actually moaned from pleasure. I couldn't believe I had this grade 9's cock in my mouth, a cock I had surreptitiously checked out when given a chance since I first met him when he was in grade 8.
I could feel Robert's mouth tentatively exploring my cock, which I knew must have tasted like cum. If he was deterred by the taste of cum or by the idea of sucking a cock it didn't show and he was soon going to town on my cock, taking it all down his throat and his little blond head bobbing up and down eagerly.
I didn't need any more encouragement at my end I was soon doing the same, taking his entire cock down my throat (which was challenging due to the large cockhead), bobbing my head up and down and trying every trick I could think of to bring him the pleasure he was giving me between my legs.
My hands played with his body while I continued to suck on his hard cock which was now oozing precum that tasted so sweet and made me long for his load which I knew couldn't be far behind.
Rob began to move his hips and I responded to his rhythm so soon he was half-fucking my mouth and half being sucked by me. I could feel his balls tighten up close to his body and knew he was close. And knowing he was close brought me to the edge.
Suddenly he tensed and as he did I could feel his cock expand in my mouth. I quickly moved my mouth up it so I could catch most of his load in my mouth. Just as I did I felt Rob take his hand and slide it between my butt cheeks and push on the butt plug, triggering my orgasm in his mouth. Clever Robert, he had figured a way to break Brian's rule about my ass being his. This made my orgasm so much more intense. In fact, I had to force myself to stop thinking about my own orgasm and remember to swallow.
Rob and I lay like that, with his cock in my mouth and mine in his, his fingers pressing against my butt plug until both our cocks went soft. Then Rob scooted around and lay on top of me and kissed me deeply.
Looking in my eyes he said "that was everything I hoped for" then looking over at Brian added "present company excluded."
Rob then jumped off me and put on his clothes. Saying to me "see you at school" and to Brian "thanks for the use of your place" he was out the bedroom door and down the stairs.
I don't know if Brian found the experience a turn on. He got to see a grade 9 naked and hard - a boy he had tried to make friends with and who had no interest in spending a minute with him. And he got to watch two people having sex. Though on the other hand he had to watch his property - me - making love to someone else and that someone else even, almost tauntingly, touched the ass he had declared was his property and used the butt plug he had put in my to protect his property to sort of fuck me.
Whether it was horniness from the former or anger from the latter, Brian was over at the bed before Rob was probably out the front door and had moved me around so I was knees on the floor bent over the bed. He removed the butt plug with one hand and undid his pants with the other, a quick spit on his cock and was entering me hard.
Brian then proceeded to fuck my ass hard. Holding on to my hips he pounded his big cock mercilessly into my ass. I don't know if it was anger or he was simply turned on, but all I could think about was having made love to Robert, the taste of his sweet cum on my tongue and his sweet kisses.
Even Brian's big cock pounding into my ass reminded me of Robert's little hand pressing on that butt plug in my ass.
It must have been at least partially Brian was turned on watching Rob and me because in what was for him the shortest time ever he was tensing up and shooting another load into my ass.
Realizing I was rock hard and about to cum again I reached for my jock that was next to the bed where Rob had dropped it and I put it under the head of my cock.
Focussing not on Rob, but on Brian cumming in my ass, it only took the last couple thrusts of his cock as he finished unloading into my ass that triggered my orgasm and I was soon shooting into the jock in my hand.
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