My fixation with anal and cock play could be traced to when I lived in South America. At the tender age of 9 my dad decided to place me in a boarding school so I could get a better education having the advantage of being totally focused on academic matters without distractions.
On the weekends, the students were allowed to leave the school grounds during Saturday afternoon, back to school for dinner and sleep and again out to the streets on Sundays until 5pm when all the students had to be officially inside the school. If one did not have spending cash on Saturday, leaving the school was impossible since it was in a remote area and one had to take public transportation to go anywhere…no money no bus that simple.
One of those cashless Saturday afternoon I was hanging around the dorm section upstairs and noticed that one of the teachers was there cleaning up and such. When he saw me he inquired as to my reason for being there.
We talked for awhile but it was mostly he asking questions and me answering. Once he finished his clean up, he asked me the favor to take the bag of garbage to the dumpster. I did and when I came back he had a coke which I readily drank. He then laid on his bed to rest and while speaking with me asked me if I would mind lying next to him.
Well there was nothing else to do and thought it was kind of nice striking a friendship with this teacher so I agreed. He placed his back against the wall and had me lay with my back towards him. While there we continued talking and then he took one of my hands behind my back and placed my fingers on this round, warm and soft thing for several minutes.
As the time went on, I was feeling this tingling sensation in my stomach and was kind of excited. Since I liked these new sensations I just laid there. He then took my hand and began sliding it lengthwise on this round thing. Mind you at this time in my life I have never seen a hard cock nor did I suspected that any thing was out of the ordinary. As the minutes passed and my hand was going back and forth, I felt this round thing getting harder and some slight bumps appeared to pop up from nowhere.
He then asked me if this was bothering me and I said no, because it wasn't really. He then asked me if I would like to try something new. I said sure. He then took me and had me stand up, my back to him and undid my belt; unzip my jeans allowing gravity to take them to the floor.
After this he took my underwear and slid it down my legs. He then stood up, dropped his pants and told me to bend over and touch my ankles which I did. Once in that position, I felt this cold and slippery substance being applied to my crack around my anus. At this time I began to think: 'he is going to stick it me' but being naïve I did not even comprehend what this expression meant so it never crossed my mind to stop him.
I felt such excitement that really wanted to see where all of this led to. He sat on the edge of the bed, grabbed my hips and pulled me over to him.
Once I was between his thighs, he slowly had me seat on him. I felt something hard sliding between my cheeks. He then stopped me and once he aligned his head with my anus, he had me slide down its shaft.
I caught a glimpse of this hard thing pushing against me and it was totally covered with skin. I had a cut dick but this one did not look at all like mine.
Anyway, the pain I felt as the head separated my asshole and began penetrating was incredible. However so was this feeling I had on my stomach and by now my dick felt like it would explode. I have never felt it hard. He asked me if the pain was going to make me cry and I said that perhaps.
He paused, slid his cock out of me and placed me facing down on the bed with my hips on the edge. My legs were bent at the hips and they kind of hung there. He knelt on the floor and had me place my hands one on each cheek. He then asked me to pull them apart which I did.
He slowly began inserting one of his fingers inside me. I felt him pushing it in until I felt the rest of this hand against my body.
He let the finger in there for a few seconds and then began moving it in and out and from side to side. He then pull it out and took two fingers and did the same as with the one. He repeated this until he could insert four of his fingers. I guess he was trying to stretch my very virgin asshole so it could accommodate his hardened tool.
Once he completed with his four fingers, I felt his head again pushing against my ass. He finally inserted his head inside me and it was not as painful as before. Once he saw that my pain was not as intense, he began to thrust his tool deeper inside me. Once he was inside me as much as he wanted, his thrusting action became more intense (read harder) and quicker.
There I was on this bed, my hands spreading my cheeks and the teacher had this thing inside me and it appeared that he liked so much, he will never stop. I don't know how long we were there but by the end of this session I had this strong feeling to go to the bathroom. So we got dress quickly and I told him that I had to go. He said fine and that no word of this to no one.
I agreed since I did not want this to get around. I went to the bathrooms downstairs and sat on the toilet thinking about what just had happened. I did not feel raped but rather turned on. Although I felt like taking a dump, nothing was coming out.
Then suddenly this white liquid came out of me. Again, mind you that I was totally ignorant and innocent of these things.
I was a 9 year old boy who just had been seduced by an older man. I sat there looking at the stool and this whitish stuff floating on the water got me really excited. Don't know why but it did. Well this was on a Saturday afternoon. Next day shortly after lunch I was walking on the school yard and the teacher came and called me.
He wanted to know how I was doing. I was just fine I told him. He asked me what did I think and I said that it was different and that I liked it.
He told me to wait and to come to his room in about 30 minutes. I did and this time he said that he was going to teach me something else.
He then again took my pants off and put more of that slippery cold stuff on my crack and anus. But this time we were facing each other. He took his pants off and this was the first time that I had a complete frontal view of his hardened tool. Comparing it to mine, it was huge. I asked him why it looked so much different than mine and he said that there were not really that different. He took my hand and had me close it over his head.
He then pulled my hand towards him while it still on his head and that was the first time I saw his head.
It looked like a gigantic mushroom. He then said: 'see, they are the same excepting size'. Well he sat on the bed and had me stand on the bed with my feet on each side of his hips.
He asked to sit down on his cock like the day before and again I stopped while he guided this gigantic head inside my ass. It hurt like hell but I enjoyed this activity even in pain.
Slowly I sat on his shaft until my cheeks rested on his stomach, There I was seating on top of this man, his manhood inside me and I liken it a lot. He then took his arms and placed the back of my knees on top of his elbows and I felt being lifted by him. I also was feeling the thrust of his cock inside me.
He did this for a few minutes and once he got tired, he stood up with me hanging on from his arms and turned around placing my back on the bed. By this time my knees were against my chest and he was just driving this huge mushroom in and out of me with a lot of intensity. Faster and faster until he began to moan and told me how delighted he was of penetrating me like this. Once he came, he slowed down his thrusting and the he just lay there, breathing heavily, cock inside me and just catching his breath.
He took his cock out of me and with a towel he dried my asshole and cleaned my crack as much as it was possible without water. When he went to clean himself, I asked him to give the towel and I would do it. He allowed me to do it. He said that it was time to leave and I did.
From this weekend on we did this in a regular basis. Sometimes I would sneak into his room at night on Saturdays and we would sleep together; well sleep would be an overstatement. He would fuck me long and hard and at times I would go to sleep having him hard inside me only to wake up with him still hard inside me. Towards the end of the school year, I found out that other older men in the school knew of our activities.
One afternoon I had to clean up my bed area in the dorm. I was there and this other teacher came and began speaking with me. The one that I engaged in sex with had left for the weekend and was not at the school. This new teacher suddenly began to tell me that he had heard that I was doing some things on the week ends that were kind of odd. I looked puzzled and played the fool that did not understand what he was saying and continued with my work.
Once I completed my chores, he called me to his office. The teachers had an office in their bedrooms. He was beating around the bush many a times and I finally asked him point want if he was referring Mr. X (the other teacher). He said that yes. When I asked him to what was he referring, he still was mumbling and could not come out and say it.
I told this teacher that whatever I did with Mr. x, I would not mind do it with him because I like him a lot (which I did). He looked surprised at my response and did not believe it. He was doing some work on his desk and I was by his side with my hands flat on the desktop kind of leaning over a little bit.
He took one of his hands and placed on my back and began to rub it. His hand made its way to my ass and his middle finger began to slide over my jeans in the middle of my crack. I could see his crotch and it had begun to bulge.
Since his bedroom had the door open, I went and closed it (with lock). I came back to him and this time he had backed his chair off the desk and was seating with his legs spread open. I sat on him and began to rub my cheeks against his hardened tool. By this time, my mentor Mr. x had taught me how to get him hard which worked fine in this occasion.
This guy was different because I felt a strong attraction to him. I stood up and turned around before kneeling. Once my knees touched the floor, my hands began to unbuckle his belt and zip down his pants. He had boxer shorts which made really easy for me to get a hold of his cock. He too was uncut and although this cock was not as long, it was a little thicker.
I don't know why but I felt like taken this into my mouth. I did. My lips surrounded the moist head of this cock and began to lick it. i don't know how long I licked but the poor guy on his chair was panting and shaking.
But what I wanted was to have him inside me and to fill me with his juices. So I stood up, took my pants down and then sat on his cock. Because I was licking it, it was full of saliva y moisten. He then stood up, took me and placed me face down on his desk. He separated my cheeks and rammed his cock inside me without mercy. This guy had no concern for me just for the release of his animal instinct. He fucked me like I was just a piece of meat. Did not even bother to clean me afterwards.
When I went to the bathroom, I saw blood mixed with the cum. I got scared at this sight because it never happened before.
Next day on Sunday I found out he was looking for me but I wanted nothing to do with him. When I saw Mr. x again, I complained to him that how come other dudes knew of our stuff. He denied saying anything but could not explain why this other guy knew it.
later on that week, a senior guy took me aside and told me that he wanted to top me but I told him that I didn't do that. Because of the violent encounter and later loose talk, I stopped my actions with the teachers completely. But that does not mean I stopped my sexual adventures with men before I was 18, but that is for another entry.