In grade 10, having turned 15 three and half months before school started, I had my first painful experience with sex. It would forever change me.
Up to this point all my experiences had been so painless and fun, and increasingly romantic, that I didn't know sex could be any other way.
I have since learned that for most boys who experiment with gay sex it is usually the other way around. Their first experiences are at best awkward and at worst painful, and it is only later in life that they have pleasurable experiences (assuming they continue to experiment with boys).
Not only was I different in that I went from painless to painful. It turns out I actually liked it and fell in love with the boy who used me. I would come back again and again for more.
My painful experience was with Brian, who had been in my class since grade 8 (that is the year I started at the school, though he had been at the school since grade 5, which is the first year you can go). His parents are rich which is why he could afford to be a 'lifer' (someone who went to the school for every year you could, from grade 5 through to 13).
By grade 10 most of the boys had stopped talking about their own cocks and how many times they were jacking off and each other's cock and thy definitely stopped grabbing each other's cock when they were horsing around. Now the talk was all about girls and a few even had girlfriends (though I don't know if having a girlfriend at that age meant anything more than holding hands, kissing and light petting above the clothes for most of the boys who claimed to be 'going steady').
Being an all-boys school I don't even know if any of these boys who claimed to have girlfriends actually did. When the school had dances we had them with the all-girls school a few blocks away (they were the only girls allowed on the school property and, even for these girls, it was only for organized functions with permission such as for a school dance). Nobody in my grade had a girlfriend from the girls' school.
A couple of my friends had girlfriends from public school who were brazen enough to illegally sneak onto school grounds at the end of sports and go off with them so my guess is these ones were getting sex. For my part, while I joined in conversations about girls, I had no interest in girls and had no girlfriend (real or imagined).
Brian was the youngest in my class, starting this grade 10 year at only 14 years of age. This is because like me he had skipped but his birthday was later than mine. Most boys in our class were 16 though a few were 15 and all were older than me.
At 14 Brian was still at that age where he wanted to grab cocks and play show and tell, and as most boys who were his friends outside of school and virtually everyone in our class had outgrown that juvenile behaviour he had now confined this playfulness to me as I was the one person who was still interested in talk about male sex organs (not cause I was still juvenile but because I was obsessed with my friends' cocks).
Brian would, when no one was looking and we were changing in the locker-room, pull down the front of his briefs to flash me some of the shaft of his cock. He always wore brown low rise briefs so it wasn't much to expose his cock and he had a big cock so he was both proud of it and there was much to show.
My locker was in one corner of the senior school locker-room right next to a big window. All the boys from grades 9 to 13 shared the senior school locker-room. This was a large L-shaped locker-room and grades 9-11 was in one arm of the L and grade 12 & 13 was in the other. The showers and washrooms were in the half where the older boys had their lockers.
Within our half of the locker-room, students were grouped by grade and class so all the grade 10s in my 'enriched' class (there was also a 'general' and 'advanced' class) were together in a series arranged alphabetically. Brian's locker was a little ways away from mine since his last name began with a B and mine began with an H, but not far because we were both in the enriched class. So I could have checked him out every day when we changed for sports or gym on my own, but he took the initiate to make it easy for me, in part because I was still willing to talk about cocks with him and in part because I embarrassed easily (knowing that none of our classmates still did that).
There were windows along the top of the walls, but there was also a big almost floor length corner window that was right next to my locker that looked out onto the back 'quad'. It looked inwards towards the back of the kitchen, but this quad which was for deliveries was where older students were allowed to smoke with permission from their parents and where parents who drove their students to and from school (like mine did) would park at the entrance and wait to pick up their kid.
The window was facing into the quad towards the school, so you couldn't see anything from the street and the smokers were supposed to stay on the other side of the quad near the emergency exit, so it wasn't like people were standing at the window smoking or sitting in their cars watch boys change. But the point is they could if they wanted to so every day I changed I was aware that people could see in if they walked by the window and that kitchen staff and delivery people who were at the kitchen entrance could see me changing. Not that anyone cared. It was all male (staff and students) but I was conscious I had no privacy beyond that of being in a locker-room changing with my fellow students.
The window was on both sides of the corner and ran from the ceiling to a few feet above the ground. Tthe locker-room was in the basement and the school's first floor was above ground level so the entrance to the school could have a dramatic walk up at the front entrance. This resulted in there being a ledge about 2 ? feet off the ground under the window at ground level below a high 6 foot window on the two sides of the corner where my locker was.
Brian would come over and sit on this window sill to talk to me, wearing only his brown briefs, not every day but frequently. As our class changed together for gym three times a week and the entire school changed for sports daily, we were used to being in our underwear. The boys tended to walk around in just briefs (guess they had either just done it so often they didn't care or were proud of their packages). So by grade 10 boys were taking their time changing and we all spent a lot of time talking to each other in various states of undress in the locker-room, trying to be like the older kids who were even less self-conscious.
So no one thought twice about Brian coming over to talk to me in his briefs, or seeing him sitting in his briefs on the sill of the window. What they didn't see, and wouldn't understand, was Brian, when no one was looking, would pull down the front of his briefs and expose half of the shaft of his big cock to me. I would look around in a panic to see if anyone could see and look out the window to see if anyone was in the quad before taking a look and then turning red and shaking my head NO as if to say "quick put that away, someone might see".
The more embarrassed I became the more he would do it. That was not a calculated design on my part. I was truly embarrassed. No one wanted a reputation for being gay in the school and I had already sucked three boy's cocks, one on a regular basis, and been fucked by the time I reached grade 10 [see the Roxbury College thread in this section]. What for him seemed to be a desire to show off his cock (which had to be the biggest in our class based on what he flashed me and how he filled out his briefs), for me it was a threat because it could out me and, once labeled gay, ruin me.
The irony of an all-boys school is that it turns out there is a lot of sex going on, but everyone is terrified of being called gay or a fag.
Brian was very forward. While in my previous encounters I had been somewhat aggressive (though I guess the other boy took the first initiative in all those cases too, I was just brazen enough to take it to the next level), with Brian the more forward he became the more timid I became.
Once, when we were under the stage dismantling a set after the school play (which he had starred in) he had put his hand on my crotch and left it there while I worked on undoing the bolts that held the set in place (my job in the production was building sets). I could hear the students next to the stage playing 'sockey' (a game like hockey but you kicked a bean bag with your foot into the nets) so I didn't respond (I didn't even get hard) terrified we were not completely hidden from view.
I whispered "do you know where you hand is" and he whispered back "on your knee" and I just kept working at undoing the bolts terrified someone would be able to see under the stage and I would be labeled a fag.
Eventually he took his hand off the front of my shorts (we were in gym kit because it dirty under the stage). I assumed he took his hand away because I didn't respond either by getting hard or by reacting extremely embarrassed as I usually do. I was beyond embarrassed, I was terrified someone would look under the stage either through the cracks between the plywood front or through the opening where we had removed a piece of plywood to crawl in at the back.
Brian lived near the school, in a huge mansion, and I lived in the south end of the city so we didn't have the opportunity to hang out when not in school. You weren't supposed to leave school except on organized trips, and on weekends it was too far to travel for either of us to visit the other. Besides, while we had always been friendly since grade 8, we weren't in each other's circle of best friends, as those were defined by where you lived or what sports you did. I did soccer in the summer and swimming in the winter whereas Brian was on the football team in the summer (he was the centre) and played hockey in winter (forward and assistant captain of the junior team).
Brian was blond and slim and obviously athletic, and as I said he came from a rich family. I came from a middle class family. He was already taller than me. I had brown hair and was about 5' 7" at this age, and he was probably 5' 8 1/2". By now my cock was around 5 or 5 1/2" (could never figure out where to measure it from), which based on checking out everyone else when we changed was pretty average for our grade. I knew Brian's was much bigger than mine, from his flashing at me when no one was looking and how he filled out those hip briefs. His was probably as long and thick soft as mine was hard.
As I mentioned, Brian and I were in the same enriched class. Our civics teacher signed the class up to compete against other schools in a model-international conference. Each school was assigned a country in the British Commonwealth of Nations. Ours was given Trinidad and Tobago. The task of our 'delegation' to the mock Commonwealth Conference was to research the country and then, for two days at the conference, pretend to defend the country's interests on a variety of international issues that we would only learn of at the conference.
The two boys least interested in this project (because we were the least academic and the youngest of our enriched program) were myself and Brian. His lack of interest was probably immaturity, because he only wanted to goof around and my lack of interest was Brian because I liked exchanging notes with him about sexual stuff instead of doing our school work.
Our class was a bunch of brainiacs, so the better (and older) students didn't care we weren't pulling out weight and naturally took over our 'delegation', which was fine by Brian and me. That left us to goof off and during the prep period. We just joked around with each other, so before long the other students in our 'delegation' were ignoring us and for our part we just wrote notes in each other's notebooks.
Most of these notes included the sort of comments that a grade 8 or 9 boy might make, like asking 'when did you last jack off' (for both of us it was always at lunch since the civic class was in the afternoon), 'ever jack off at school' (yes for me, no for Brian who could go home at lunch and jack off there), 'where is the strangest placed you jacked off' (me was behind the boathouse at McKay Lake, though I didn't tell him it was after I sucked off one of our grade 8 classmates, Anthony, and for him it was in a department changing room so he could look at himself in three way mirror) and so on.
Our notes were always sexual. This wasn't the only class we wrote notes in each other's notebooks. We did it in most classes when the teacher wasn't looking and we happened to be sitting together, which wasn't often because you usually sat next to the first friend you saw when you arrived at class and we were all pretty good friends it being a small class of about 10 people. But during the week leading to the conference people broke off into groups so Brian and I would pick two desks in the back and huddle together pretending to read material about Trinidad and Tobaggo and our intensity of writing sexual references increased and it was having a decided effect on me. I found myself lying in bed at night thinking about Brian and I would have to stroke one out with the final thought before I came that part of his shaft I could see when he pulled the front of his brown briefs down slightly sitting on the window sill next to me locker.
The conference was to run for a full weekend. It turned out that both my parents and Brian's were going to be away during that weekend (by coincidence, not together). So my mother had contacted the other moms because I would need a drive to and from the conference. The father of my classmate Wayne (Wayne lived fairly close to me in the south end of the city) offered to drive me; and Brian's mother proposed that Brian stay with me to get in on the transportation since the conference was not near school which is the area of Ottawa where he lived.
So it was decided Brian would stay with me starting Friday night and Wayne's father would pick us up Friday night after school sports and return Brian to his parents' house on Sunday night when the conference ended before dropping me off and returning to their home.
Brian was in another school play at this time and so Wayne and his father agreed to attend the play Friday night (there was never a question about parents and students attending school plays, it was what just a question of what night you would). They would wait on Brian to be finished Friday night with the play and then drive me and him to my place and pick us up again in the morning and take us to the conference.
I didn't have anything to do during the play as I worked on sets, but as part of the production team I could stay 'backstage' (which simply was a classroom near the big room where students played sockey during recess and after lunch). So after the play I hung out there, rather than waiting with Wayne and his dad. Brian took forever to change, spent a fair bit of time in his briefs as he removed his make-up. He also seemed to have an edge, picking on one of his co-stars first over what he called a poor performance (I thought the kid was as good as any of the others) and then, when the kid removed his costume, accusing him of not having reached puberty yet (the boy was only in grade 9 and short and while it was true he didn't fill out his red regular briefs very well standing right next to Brian who by now was reclined along the window sill putting on his socks with his package which I knew to be huge for his age and looked even bigger with him wearing those low rise briefs, I also thought that was unfair).
When we left the classroom/backstage I asked Brian about what was going on he dismissed it saying "he has been badmouthing me all week". He then instantly turned on a dime and put his arm around my shoulder and said "this is going to be fun, it's like going camping. I can't wait to see your place."
On the drive home Brian was pretty giddy. I figured it was the adrenaline from the show combined with his idea that we were going on an adventure like a camping trip. But a lot of his giddiness came out in the form of sexual references, which embarrassed me in front of Wayne's father, but Wayne's father just laughed. I guess he realized that Brian was, being 14, a bit immature or maybe he thought that this is still what boys our age say in an all-male environment.
To deflect any idea of gayness away from me, I feigned being nervous about staying with Brian (though secretly I was looking forward to it, hoping to see and hoping to even touch his cock given his touching mine under the stage following the fall play). I begged Wayne and his father to let me stay with them instead of Brian and they laughed and Wayne's father jokingly asked if Wayne wanted to stay with us and he emphatically said no. Ironically, years later Wayne came out as gay whereas Brian is happily married with two kids.
I lived in a townhouse which wasn't particularly big. It had two bedrooms, mine and my parents on the second floor, with a hall and bathroom between them. On the ground floor was one big room, which was L-shaped so was a living room and dining room, and a small kitchen. For Brian to sleep over mom had put two sleeping bags in the living room; I guess she figured we would want to stay up and talk (or maybe she didn't want Brian sleeping in her bed and didn't like the idea of us sharing my bed, even though it was a Queen-size).
When Brian walked in he commented on how small it was, but then quickly added "this will be fun, it's like being at a cottage."
It was already late when we got home because of the play and the long drive home, and while we had no desire to sleep, we undressed to get in our sleeping bags. I had been sleeping naked since I was 13 and the thought of wearing anything to bed didn't appeal to me (which I explained to Brian defensively). I quickly stripped off my school uniform - black patenleather shoes and black socks, blue blazer, grey flannels, white shirt and tie, and, for me, classic white briefs (mom said they were easier for her to wash because she could use bleach) - and jumped into my sleeping bag
Brian looked hot when as he stripped off his uniform down to low rise brown briefs, which I had already been busy surreptitiously checking out when he changed before and after the play, but now I made no effort to hide my watching him undress and for his part he didn't seem to care. In fact, it was almost like he liked me watching him given how he took his time undressing and then didn't get into his sleeping bag right away, sitting in one of the chairs in his briefs, making small talk with my about my parents and how long we had lived there.
Neither of us wanted to sleep and we talked into the night, with Brian eventually coming over to where I was and climbing into his sleeping bag next to me. Once in his sleeping bag our talk became like the notes we had written in each other's notebooks. In response to his questioning I admitted to having put a finger in my ass once or twice when I jacked off, but lied and said I had never done anything with another boy. Brian claimed to not only never have touched a guy, he had never fingered himself and he told me each night he took a Glad bag, put some Vaseline in it, placed it in a dent he made in a pillow and fucked it every night before he went to sleep.
The image of Brian on his bed naked, a pillow under his hips as he fucked it, that tight athletic ass and slim hips moving up and down, was so vivid I couldn't help myself, I not only sprung a boner. At this point Brian moved his hand into my sleeping bag and was rested it on top of my cock and balls like he had done under the stage that time. But this time I had a boner and he had to know it was because I was picturing him fucking his pillow.
Pretending not to be flustered, I said, trying to keep any emotion out of my voice, just like I that day under the stage, "do you know where your hand is?" "On your knee" he replied like before. I said nothing.
While I was embarrassed to be hard, I couldn't help myself and my boner continued with his hand resting on it. He didn't move to stroke it or explore it, he just had it resting on my package and we both pretended his hand was not there for a while as we talked. Interestingly, given his hand was on my cock, he began to talk about girls (e.g. who was the hottest in our grade in the girls school, what movie actresses we liked). I guess if we did our usual banter about each other's cocks and what we had done to ourselves that would have seemed gay while he had his hand on my cock.
Eventually he said "we should get some sleep, it is almost 5am and Wayne's dad is picking us up at 7". He took his hand off my cock and rolled over in his sleeping bag. I lay there with a hard-on thinking should I jack off right there (I decided 'no' cause he would hear me and that would confirm what he probably suspected, I was gay for him) or can I get up and go to the bathroom and jack off (but that would involve standing up naked and while he had already touched my hard cock, I didn't really want him to see me naked with a hard-on since my cock was so small compared to his and it would have equally been obvious I was going off to jack off and that meant it was over him and I was gay). So I simply went to sleep.
The next night we got home earlier because we came home after the conference and a dinner with Wayne and his dad, but it was still fairly late and we had only had two hours sleep the night before. We watched a little TV and did some horsing around, including wrestling where we grabbed each other's cock through our grey flannel pants. Eventually Brian suggested we should go to sleep.
We got undressed and into our sleeping bags and turned off the lights. After a while in the dark silence Brian said "you seemed to like my story about fucking my pillow last night?"
"I don't know what you mean," I said, knowing exactly what he meant.
Brian then shoved his hand in my sleeping bag and, sure enough, I had a boner which he squeezed.
I pushed Brian's hand away and began to wrestle again and during that pushing and pulling back and forth I put my hand into his sleeping bag and grabbed his cock and it was rock hard too. It was huge, must have been almost 8 inches and thick. He was only 14, and his cock was so big half of it was sticking above the waistband as his briefs were too low rise to confine it.
Brian stopped struggling and I still had my hand wrapped around his cock.
Brian said "you don't seem to be trying to hurt me", calling me out on the fact that I had grabbed his cock during wrestling him but not as a move to win the fight but simply to wrap my hand around his cock. Embarrassed I let go of his cock and took my hand out of his sleeping bag and jumped up and ran out of the living room bare-assed, running down into the basement.
Brian followed me and grabbed me and we wrestled to the ground in the basement, both of us having hard cocks, me totally naked and thus totally exposed and his mammoth cock sticking up above his briefs.
Brian pinned me so his legs were on my shoulders on either side of my head and his underwear and his big cock towering above my face, now looking even bigger close-up sticking out of the waistband. I looked up at him and he looked down at me.
"Take a sniff fag," Brian said, pulling my head up so my nose was buried in his balls. Instinctively I inhaled.
While he began to laugh I shouted "no" and pushed him off of me. Getting free, I ran two flights of stairs up to the bathroom where I ran inside and locked the door.
Brian seemed intent to make me admit I was a fag and this wasn't the sort of fun grabbing cocks and balls I had done when I was younger. He seemed intent on dominating and humiliating me.
Brian had followed my upstairs. But after trying the door knob he left me in the bathroom. I could hear him walking around and eventually I heard him should "why didn't you tell me there were big beds up here. I am sleeping up here."
After a while I came out of the bathroom. My hard-on had gone down and I held my hand shyly in front of my crotch. I found Brian nestled in my parents' bed.
"Where am I going to sleep," I asked. Standing next to the bed with my hand trying to cover my average-size (puny compared to him) cock.
I had liked being in a sleeping bag next to him in the living room as we talked about sexual things. I wanted things to go back to the way there were and hoped we would go back downstairs. Well, part of me hoped he would throwback the covers and say "with me".
"You can sleep in your own bed," he answered.
"I don't want to," I said in what was a very pouty voice. My feelings were hurt and I grabbed a blanket out of the hall closet and lay down on the floor in the hall between the two bedrooms.
After I lay awake on the hard floor for what must have been an hour, Brian said "ok, you can sleep in this bed with me".
I climbed in and lay facing away from him. I was naked, and I assumed he was still wearing his briefs.
When he slid up behind me it became apparent he had taken off his briefs as I could feel his hard cock, balls and boney hips next to my boyish round ass, He put one hand around my chest, holding me, cuddling me, and I didn't feel rejected anymore.
I could feel his big cock against my butt cheeks, as he moved around so it slid up and down the crack. I didn't move or resist. I was in heaven being held with his arm around me. And, besides, I knew I liked being fucked from my one experience in grade 9.
He moved away and I felt deserted but within seconds one of his hands was on my ass and I could feel his wet fingers against my hole (I guess he had moved away to lick them). Then I could hear him spitting in his other hand and feel his spit being applied to my ass crack. I guess he was also doing it his cock because only every second spit went to my hole. I knew what was coming but I didn't move. Part of me liked him being in control and me just being about to be used.
I knew that Brian's cock was about an inch longer than the boy who had fucked me in grade 9 and much thicker, but he was 14 years old and I wasn't a virgin (in spite of what I had told him) so I wasn't nervous, just horny.
He just kept spitting and wetting the hole. I felt his fingers shoving the spit into my hole and loosening me up. Some of the intrusion into my butthole hurt but overall I loved his touching my ass. He seemed to know what he was doing so I wasn't sure if he had lied and had actually done things with boys before or was just going from what he had read in Penthouse Forum which in grade 10 we all passed around the locker-room. I smiled to myself when I also thought "and he had lots of experience with his pillow".
When he was ready he placed the head of his cock against my hole and began to push.
He had to push hard, it being almost a year since I had my cherry popped and him being so big, but eventually the head slid inside.
I gasped. It hurt so much. It hadn't been like this the first time, but then that boy not only had his cock been slimmer we had used the foreskin to pry my hole apart and funnel it into my ass. We were trying to do this with a mammoth 8" cock and only spit on my tight semi-virgin 15 year old ass.
Whispering in my ear he said "roll onto your stomach" and before I could move he took hold of my shoulders and rolled me onto my stomach himself, his cock going deeper into my ass as we switched positions. It hurt so much and I wanted him take it out and I told him so but he didn't seem to be listening. I knew that Brian had to only be about a third of the way inside me and he was already splitting me open like a trout.
He put a pillow in front of my face and said "bite on this". I guess someone with half a brain would have continued to beg him to stop or pushed him off and jumped out of bed and run away but I did as I was told and bit on the pillow,
He used his knees to push my legs apart and push further into me at the same time.
Pushing at a steady rate with no pause for me to get used to it, it hurt like hell. I felt it slowly go in and could picture every inch. I could feel every vein and curve as it entered me since the only thing between his cock and my anus was a little spit.
Part of me wanted to cry out from the pain of my ass being stretched but the bigger part of me was so fixated on this cock I have had quick glimpses of in the locker-room and touched downstairs a little while earlier.
He kept shoving and I kept biting on the pillow. Eventually I felt his hips against my ass and his balls against the back of my balls and I realized he was entirely inside me and I was his.
I wanted him out of me, he was just too big. But I felt I didn't have the right to ask as he had now conquered me and I certainly had asked for it, hadn't I?
He then whispered in my ear "I will give you a minute to get used to my cock being inside you and then I am going to fuck you". I don't know if that was supposed to relax me but it had the opposite effect. I suddenly knew the pain was not going to stop and my heart panicked.
Then he reached between my hips and the bed and grabbed my cock. It was not affectionate it was rough, though my cock stayed hard at his touch.
We stayed like that for more than a minute, with his hand under my hips roughly stroking my cock as his own cock was buried all the way to the hilt in my ass. As more time passed I began to relax, the one minute warning had come and gone and I was getting used to my hole being stretched around this big phallus.
Suddenly, Brian then let go of my cock and pulled his hand out from under my hips, wrapping each hand up under each of my two shoulders and lowering his full weight onto my back and ass. I tensed. His cock still felt too big for my ass and I bit down hard on the pillow expecting searing pain.
He started just by moving his hips which wasn't too bad and I relaxed a bit, but it still hurt like hell and kept biting down on the pillow so I wouldn't cry out. Before long he was gripping my shoulders tight, pulling down on them as he thrust up and tried to shove his cock deeper into my ass, if that had been humanly possible.
It went on forever, my lying face down on the bed with his weight on my back and my ass being pounded hard. And I was panting and, while my mind was screaming stop, my cock was hard so I must have been enjoying it at some level, mustn't I have?
I felt trapped under him, and the pain tore through my body beginning at my asshole and radiating out to the top of my head and to the tip of my toes with every stroke he took. I was sure whatever spit had separated his cock from the sensitive skin around my hole had long since dried out as his cock felt like it was grating along my hole as his thick shaft moved in and out of me. I could feel tears streaming down my face (though I was damned if I was going to let him hear me sob or cry). I gripped and bit into the pillow, as hard as his hands gripped around each of my shoulders.
At the micro, through the rawness of my anus my brain imagined every tiny curve and muscle in his cock, and I had a picture of his hard penis so firm in my mind as if I had studied it like a painter or a sculptor for days before capturing it on canvas or in marble. Marble was how this rock hard cock felt in my ass which had, in my mind, now been reformed to fit this extension of Brian like a glove, making me an extension of Brian myself.
At the macro our entire bodies were in contact and I realized that in spite of the intense pain I was feeling on the inside, I enjoyed on the outside of my body both being pinned under his weight and the total body contact we had. I could feel every inch of his body, his sweating chest against my back and the front of his legs moving against the back of mine, his boney hips pressing against my round firm ass cheeks, even his feet against mine as they tensed and relaxed, forcing his body up into mine; and his hot breath against my neck as he panted with each thrust into my ass, which felt like it had to be on fire and triggered a similar breathing pattern in me.
I could feel every inch of his big thick cock sliding in and out of my ass, his balls hitting the back of mine on the down stroke.
His breathing got faster in my ear and has balls slapped less and less against the back of mine, and I knew he was getting close. Plus, if such a thing was possible he was getting rougher on my ass. He was about to blow.
Just I realized that he grunted "I am cumming" in my ear and gave four deep sustained thrusts, hard into me pausing there and relaxing and then again, each one depositing a load deep into my ass, before collapsing on top of me.
He lay like that for a while and I could feel his breathing getting slower. At first I thought he was just calming down after his strenuous workout, but soon I realized he had fallen asleep on my back, his cock still inside me. I could feel him softening in my ass.
I lay there wide awake for a while thinking about his big cock which was now soft but stilled filled my ass. His cock was big and gorgeous and I never felt so complete, even though I was incredibly sore and sensitive his having just massacred my ass.
I hadn't cum but I was exhausted from the workout he had just given my ass and from only had two hours sleep the night before. I was also happy being under him and with his big cock still filling my ass, so I turned my head on the pillow and folded my arms under it, and fell asleep under him with him still inside me.
I am not sure how long we slept like that but I awoke as I felt him roll off of me or, more to the fact, felt his cock leave my ass. He rolled over facing away from my and went quickly back to sleep. While I continued to lay there face down, head and my folded arms and pillow. My ass felt so sore, but it also felt so empty. I longed for him to be back inside me even though I could barely move I was so sore.
Somewhere during the night we must have moved around because when I woke up in the morning I found Brian next to me on the bed lying on his back and me cuddling under his shoulder. He has his arm around my shoulder and I had my arm across his chest. I lifted my head from the nook of his shoulder and looked up at him and realized he was awake and watching me sleep.
"Morning he said," showing no sign he acknowledged he had basically raped me the night before or any concern for how I was doing. But he also made no move to push me off him and move away. "Wondered when you would wake up,"
When my head emerged fully from my sleepy haze I realized I had a morning wood pressing against his hip as my leg rested over his thigh.
Like he could read my mind he said "you seem to need to get yourself off." I noted he hadn't offered to get me off, in repayment for having so mercilessly fucked my ass the night before. But again, I was thankful he was not pushing me off him and calling me a fag or running away.
He threw back the sheets and blankets so our naked bodies were exposed.
"You can jack off looking at me if you want," he said with the smugness that said I know I own you and you want me and I am god's gift to anyone and you may have a small piece of me.
In any other situation I would have said "fuck you, you arrogant prick" but he was gorgeous and we both knew it. And I wanted to cum.
I got up on my hands and knees and kneeling beside him I began to stroke. I reached out to take hold of his soft cock (I guess having shot so much inside me he didn't wake up with a hard-on) and he stopped me by saying "did I say you could touch me." I withdrew my hand.
I kept stroking my cock and looked him up and down. He was gorgeous lying there naked and, as I stroked, the memories of the pain of his hard cock inside me gave way to lust at wanting his cock.
I watched as that thick cock hardened in front of me, going from lying against his thigh to pointing straight up and it climbed toward his belly button along that ever so fine track of hair that ran from his pubes to his navel. Soon he got rock hard and, as he did, his hand moved to my ass and a finger slid in between the cracks.
"I am too sore," I pleaded.
"Then use your mouth," he commanded, though he didn't remove his finger from my ass so I guess he assumed I meant I was too sore to take his cock again. I was also too sore to take his finger, but I wasn't going to correct him.
I was quickly bent over him deep throating his big cock,
"Damn," he exclaimed, "thought you were a virgin, and you sure felt like one last night, but now I know you have done this before,"
Lots of thought went through my mind running from if you believed me when I said I was a virgin and I felt like one then why did you not go slower or stop when it hurt (wasn't that rape) to I did lie to you and I am not a virgin (so I am in the wrong). But that didn't take long because deep throating a big cock like Brian's takes concentration and before long I was in my grove of taking it down my throat and lifting my head back up so it was still in my and then back down again.
Brian kept finger fucking my ass and even though it was raw sore, which meant what he was doing hurt, it also meant it was super sensitive and in spite of the pain it was making my cock throb the way his big cock had the night before. The faster he fingered me the faster I went up and down on his cock. Soon the sensations were too much and I could help myself and I began to cum and I could feel as spray after spray shot out of my cock and onto Brian's legs thighs and chest.
I guess making me cum from finger fucking me combined with my deep throating was enough to push him over the top and Brian started cuming too, which I moved up on his cock to catch in my mouth.
I stayed like that, bent over him with his cock in my mouth until he removed his finger from my ass, which was after he had gone soft. And when he removed his finger I took that as him giving me permission to let go of his cock.
Lifting up from bent over, I sat back on my haunches, in the position I had been when I first started stroking. I looked at this blond Adonis lying there, his cock now softly laying on his thigh, but so big and still glistening with my saliva and some residual cum that I had missed (though I was sure I got pretty much every drop). When I looked to his face, I realized he was watching me admire him and he had a smile that showed he was pleased with himself.
He raised his hand and offered me the finger that he had up my ass and without hesitating I took it into my mouth and began to suck, sacrificing what remained of my dignity and any pretence that I was anything but his bitch now.
"You lied to me," he said sternly, as I sucked on his finger, "you are going to have to come clean and tell me who did you learn to suck cock from - and I bet you weren't even a virgin - but later, now I have to take a shower". And Brian jumped out of bed.
I quickly showered after him and we were barely dressed and down in the parking lot when Wayne's father pulled up in his car. I could still taste Brian's cum in my mouth and my ass felt so stretched that I thought everyone I encountered that day could tell from the way I walked or the way I sat that I had been fucked hard the night before.
I was sad that Brian would not be staying another night and my parents would be coming home. But I also knew it would be days or weeks before I could take anything in my ass, be it his or my finger and definitely not his huge cock,
When my parents returned they informed they were getting a divorce and I was pulled out of Roxbury the next week and went with my mother to her family's in Nova Scotia. It would be a year before I went back to Roxbury, once their divorce was finalized, and this time I would be sent there as a boarder and not as a day boy.
NOTE: Nifty needs donations to provide these stories. http://donate.nifty.org/donate.html