Speech Day
The next experience I had was a day I will always remember it was on School Speech Day, this was when all the awards for the year are given out. It was just a few days from the end of the Summer term. I was surprised to win the award for best behaved pupil as voted for by all the teachers. When I went up on stage to shake hands with the Head Master he said he had been impressed with how I had helped the teachers when asked and hoped I could maintain this good behaviour during the rest of the time at the school and how I was a good example to the other students. I was cringing a bit as he said it knowing the other students would think I was a bit of a creep to win this award and thinking they would not want to associate with me.
My class mates were all joking with me when I sat back down calling me "teacher's pet" and "ass licker". After all the academic and sports prizes had been handed out the last prize was for the most popular student as voted for by all the other students. My class all said it would won be either Blake the Head Boy or Scott the School Rugby team captain. I thought it would be Blake as I had voted for him, we were all making bets on which one of them would win.
We were all shocked when Scott came third in the vote and Blake came second and everyone in the hall started talking about who could have beaten them. The Head Master asked for quite then announced I had won the prize I couldn't believe it, my class mates all looked at me strangely and told me to get up to collect the prize. When I got on stage the Head Master told me to speak into the microphone. All I could say was
"Thank you for voting for me this is a great honour and I am not sure what I have done to deserve your vote, but I will try my best to keep doing it. Thank you all"
I found out later I was only the second pupil in the school history to win both these awards in their first year in the school. Little did I know that the words I had spoken in my acceptance speech would come back to haunt me at the start of the next term.
When the ceremony was over, and we were all leaving the hall Blake and Scott came up to me to congratulate me on winning the Student vote and asked if I could go with them to Blakes' study room as they had something for me.
When we got his study, Henry the deputy head boy was waiting for us with a bottle of Vodka. Pouring us all a glass he said
"Well this is a surprise what will we do about the bet now"
"What bet" I asked
"Blake and Scott made a bet that whoever came first could fuck the one who came second in the student vote, and now you have come first"
"Yes" said Scott "and I only came third and the bet was about who was first and second so Tim should get to fuck Blake"
I was too shocked to say anything my head spinning thinking did I really hear him say I should fuck Blake the Head boy he was like 18 and I was just 14 (almost 15).
Blake didn't say anything and just looked at Henry who had been asked when the bet was made to make sure it was carried out. Henry thought for a bit and said
"Scott does have a point the bet was about first and second place and even though you both thought it would be the two of you, the fact that Tim has come first does not change the bet. I agree with Scott that Tim as winner gets to Fuck Blake who came second"
I had never fucked anyone before and now here were these three senior boys agreeing that I should fuck one of them. I could feel my cock getting hard at the thought of it. Blake dropped his head as Scott's face lit up with a big smile, these two 18-year-old boys had been rivals for the senior pupil in the school for the last year and now instead of Scott getting fucked by Blake I was going to Fuck Blake. I think Henry who was 17, and would become the Head Boy in the next School Year had been asked to act as the bet judge as he was one of the nicest guys in the school.
The next thing Henry said really surprised me
"As my role is to make sure the bet is carried out we better get on with it, you can go if you want Scott"
"No way I was going to be the one receiving the fucking, so I want to watch Blake getting what he was going to give me"
"Ok Blake you better get stripped" Henry said looking at Blake
I watched open mouthed as Blake slowly undressed revealing his strong chest and rippling abs which had been developed through the years on the school's physical development program. He dropped his trousers and then slowly pushed his white y front underwear down revealing a bush of pubic hair above his cock which hung down above his big balls. Watching this had, got me so hard I could feel my cock pushing against my school trousers.
Henry looked at me and said
"Tim now you have seen you fuck buddy naked it's your turn to undress, is this your first time"
"Yes" I said as I quickly throw off my clothes
Henry got some clear gel from his bag and slowly coated my hard cock with it
"You've got a big cock Tim, Black is really going to feel this going in, so you better take it slow to start with" He then guided me holding my cock to stand behind Blake who was bent over the desk with Scott holding his arms which were stretched out in front of him across the desk.
Slowly Henry pulled my cock up against Blakes ass hole and told me to push it in slowly. It was tight, and I struggled a bit to get it in but suddenly the head of my cock popped inside, and Black let out a moan.
"Ok Tim take your time pushing it in, as like you, Blake has never been fucked before so give him have time to get used to the size of your cock"
I slowly pushed it in inch by inch stopping while Blake groaned and moved a bit. Eventually it was all in and I could feel my body tight up against his bum.
"Now you can slowly start pulling it out but not right out then pushing back in" Henry seemed like an expert about fucking and I was glad to have him as my teacher. Soon I was really getting into it pulling almost all the way out then all the way back in.
Scott started shouting to me to fuck him harder saying things like breed the bugger. I had leaned over a bit and put my hands around Blakes hard body to get a better grip and I could feel my excitement rising, here I was hands around the naked head boy with my cock inside him. He was starting to grunt a bit as I was rubbing against something inside him then he let out a load moan as his ass started clamping and releasing against my cock I didn't know it then, but I had been hitting his prostrate and had made him cum. At the same time, I started shooting inside him still moving in and out and feeling my jets of cum shoot out with each forward thrust into him.
I collapsed on top him exhausted and elated my chest lying against his now sweaty back and I could smell his body it was the best feeling I had ever had in my life.
Scott was the first to talk letting go of Blakes arms "That was fucking awesome I am glad that was you Blake not me" all Blake could say was "ohhh fuck" as he slowly raised himself up from the desk.
He turned to face me the two of us standing naked with these two other clothed boys looking. I could see cum still dripping from his cock which was now half hard and sticking straight out. He went to shake my hand but then changed to putting his arms around me and hugging me. I could feel our cocks touch and mine start to get hard again.
When he pulled away he said "That was an experience and I don't think I will ever make a bet again"
I was looking at him thinking he was the most gorgeous guy in the world, as I watched him start to dress. When I got dressed I shook his hand and told him I was going to miss him and thanked him for helping me in my first year in the school. He said he thought I was a great guy and would miss me too, that gave me such a wonderful feeling. Henry then said we had better leave as Blake and Scott had a meeting with the Head Master soon.
Let me know if you have any questions about his experiences and I will ask my Uncle. I will post his next experience soon.
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