How my cherry got popped

I’ve had a fetish about white jockey briefs since I was 16. I like the way the double layer of cotton feels so smooth when I rub my balls and right round to my bum hole. One day I got caught doing this by my mother. She told me to stop doing it because I might end up all queer. I knew what she meant but in those days didn’t exactly know what people who were “all queer” got up to, just that it was forbidden.
Every Tuesday at high school we went swimming at the school pool straight after lunch. The English teacher used to take the lessons and generally keep control of the idiots who preferred to spend their time running round, dive bombing and causing a nuisance to other boys. He also had our last class for Tuesday afternoon teaching English.
After swimming the boys had to take turns staying behind to help tidy up, pick up litter etc. The day that it was my turn my two friends were also asked to help. I knew they hated the idea and, seeing as I hated maths, I told them to go and I’d do it. So they left straight after getting changed.
It took me about 30 minutes to clean up and then I started to get changed in to my normal school clothes. I had just put my knickers on. They were my white jockey briefs. I only had one pair and it just so happened I was wearing them that day. I looked around the changing rooms to make sure no one was there and then started to rub my balls, then between my legs and right round to my bum hole. As usual the soft double cotton felt really nice and smooth. I kind of felt dirty because this was the first time I had done this in public.
I had finished getting dressed and turned to leave the changing rooms when I saw the English teacher watching me. I think I started blushing because I didn’t know if he had seen anything, only that he wasn’t there when I had checked.
I quickly turned away and went to the rest of the maths lesson.
Throughout the maths lesson I kept wondering if he had seen me rubbing myself through my knickers. I knew that I had to go to English but wasn’t looking forward to it. When I got there I decided to sit down the back in a corner where I could kind of hide. All through the lesson I didn’t look at him, and he didn’t ask me any questions to answer, which is unusual because I was one of the top English students.
When the bell sounded for the end of the lesson he yelled out over the top of the noise and asked me to stay behind to discuss the last test score. I was kind of surprised because I had got 98, and the nearest mark was 85.
After everyone had left he came over and sat on the desk in front of me.
He said that he didn’t want to discuss the test score and that he had said that so the others wouldn’t think anything of me being asked to stay behind.
He told me that he had seen what I was doing in the changing rooms. I started to blush and looked away. My mouth went really dry because if he told my parents I would be in a lot of trouble.
He said that I didn’t need to feel ashamed and that he wasn’t going to tell anyone. He told me that I looked good in those knickers, as good as I looked in my speedo briefs. He said that it was perfectly normal for boys to explore their bodies and their sexuality and, that if was gay, there is no shame in that either.
I told him that that I’d never had sex with anyone so there was no way I was gay. I just liked the way they felt when I touched my body in them.
He smiled, took my hands, and asked me to stand up.
He said that when he was my age that he went through the same thing and it wasn’t until years afterwards that he admitted to himself that he liked men.
He asked me if I ever had any thoughts about being with a man and that if I said yes he wouldn’t tell anyone and I did not need to feel ashamed.
I said yes, I had thought about kissing a man on the lips and touching him the same way I touched myself.
Admitting this made my penis suddenly get a bit thicker. My stomach got a huge adrenalin rush and my chest tightened so it was a little difficult to breath.
He asked me to close my eyes, which I did. I then felt his lips touch mine, a light simple kiss. My penis got even thicker and the adrenalin went through my stomach again. He hovered close to my face and, when I didn’t move away or react negatively, he kissed me a bit harder.
He held that kiss for a while, let my hands go and put his arms around me, with his hands in the small of my back.
He gently pulled me towards him so our bodies were touching. I’d never done anything like this before, only in my fantasies in my bed. It was like an electric charge going through my body. His tongue pushed in to my mouth and probed my own tongue and around inside my mouth.
His hands moved on to my bottom and started gently caressing and squeezing it.
After a while he broke the kiss and asked me if I would like to find out what it was really like to touch another man through his knickers.
I croakily said yes.
He undid his belt and fly and pushed his trousers down to his knees. I looked down and saw that he was wearing dark blue speedo type briefs and that his penis was absolutely huge through them.
He took my hand and placed it on his balls and started to move it around. It felt nice, nearly as nice as my own felt. Soon he asked me if I would like him to do this to me. I said Ok and pushed my school pants down to my knees.
He cupped by balls in his right hand and started gently massaging and twisting them while at same time his other hand was gently raking his finger nails up and down my penis. His right hand moved from by balls to between my legs and finally to my bum hole. He placed his mouth over mine and kissed me again. When his tongue entered my mouth he pushed his fingers inside my knickers and started massaging my bum hole.
I moved my hand from his balls to his penis and stated squeezing and rubbing it. His left hand pushed his knickers down just enough to free himself. His large penis sprang out and stood upright. I had seen other boys in the changing rooms but nobody had anything this size.
He pushed my knickers down just below my hips, freeing my own, by know, extremely hard penis. He broke the kiss and knelt in front of me so his face was level with my hips. He then took my penis in his right hand and placed it in his mouth. Man that was electrifying! His mouth started to move gently up and down my shaft. It was like nothing I had ever experienced before.
He took me out of his mouth, placed his hands on my hips and motioned me to turn around.
I did and what came next was a real shock.
He told me to bend over a little and then I felt his face pressed between my bum cheeks. His tongue started to run up and down my bum crack and finally settled on my hole. He licked and licked for about a minute while at the same time stroking my penis.
He then stood up and pushed me on to the desk so I was leaning on my elbows. I then felt his slippery fingers get inserted in to my bum hole. It felt really weird. Kind of burnt and I wasn’t sure if I liked it or not. After a while it started to feel quite nice, especially when he started to stroke my left nipple. I’d never done that before because I always thought girls’ nipples were supposed to be played with. He really made the fingers in my bum hole feel good when he played with my nipple.
He said that a lot of guys love anal play and sex and really enjoy it most when they rub or pinch their own nipples while masturbating at the same time. I started to rub my penis and boy it felt good. It felt really good.
He must have known how much I liked it because he took his fingers out and I soon felt something else touch my burning bum hole. It felt much bigger, softer and fleshier than his fingers.
He stopped rubbing my nipple and put both hands on my hips. He said that we would leave my knickers where they were so they could “catch the drips”. I had no idea what he meant by that.
He took a firm hold of my hips and I felt him push. I suddenly knew what the bigger, softer and fleshier thing was. It was his penis! I was about to have my cherry popped by my English teacher!!
At first he couldn’t enter me as I was still pretty tight but he kept re positioning and pushing. Finally I felt my bum hole open and the head of his penis enter. I gasped in pain and he stopped pushing. He said it was all right and that it would hurt at first because I was a virgin and tight and that once he was through it would feel nice again. He reminded me to rub my nipple and masturbate myself.
I did this and while I was doing this he stayed still. Shortly after I was turned on again and felt him start pushing again. I could feel his penis go through my ring and the shaft slide inside my hole.
It was the most incredible stretching and filling sensation.
Once he was all in he stayed there and let me get used to it. I kept rubbing my nipple and masturbating.
I soon started to breathe heavily and that was his key to start moving in and out of me. I felt his entire penis sliding in and out, in and out in a steady rhythm, stretching and filling me. After about three minutes of this he started to breathe heavier and I could hear him moaning. The rhythm started to get a bit quicker, the thrusts faster and shorter and his hips were making a slapping sound on my bum cheeks as he drove his erection in and out of my hole.
Suddenly he thrust all the way in and I felt his penis get even bigger. It then started to throb. I think it throbbed twice before he took it out again and then viciously thrust it back in. He did this four times and at the end of each thrust I felt his penis throb two or three times. All the time he was moaning and saying what a tight little pussy I had and that I needed more of this to loosen it up.
When he stopped he left his penis inside me, reached round, took my penis in his hand and massaged it up and down. The head was caught in the fly of my knickers and his massaging was making it rub against the soft cloth.
All this and the thought of just getting screwed were too much. I felt my balls tighten as my penis erupted in to my knickers making them very wet.
His penis slid out of me and I felt warm liquid ooze from my hole and down my balls. He gently pulled my knickers up to where they had been about ten minutes ago. He made sure that my penis and balls were firmly in place and that the elastic around the legs was also set in the proper place. He patted my bum cheeks and I heard him pull his own knickers and pants up.
I pulled my school shorts up and turned to face him. He smiled at me and said that as soon as he had seen me playing with myself in white jockey briefs he knew that I was gay and that I just needed someone to break me in gently so I would enjoy my first time and not be put off by it.
I said that I did enjoy it and wanted to do it again, maybe next Tuesday.
He told me to make sure that I washed my knickers myself as soon as I got home otherwise others might know what I had been up to.
As I left the building and began to walk home I found out what he meant by “catch the drips”. I felt his cum leaking out, making my knickers warm and wet. By the time I got home they were saturated with both mine and my English teacher’s cum.
For days afterwards I ached where he had been and constantly felt like he was still there, stretching and filling me up.
We only did it another 5 times before he had to leave. Talk round the school was that he got caught with one of the senior boys.
Ever since then I fantasise about getting screwed with my white jockey briefs catching the drips.

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Posted by Shyboy02
1 year ago    Views: 13,568
Comments (9)
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11 months ago
nice story, really good hot read
1 year ago
really hot story I love it
1 year ago
Hot story read my Dicky's first time about getting my ass fucked when I was 12.
1 year ago
Hot story shyboy02, loved it..
1 year ago
you can have your english teacher do me anytime
thabnks for leting me cum too
1 year ago
Thanks. Would love your cock pumping my love hole. Bet your cum would saturate my knickers.
1 year ago
Thanks. Made me wet my pants when I was writing it.
1 year ago
love the story
1 year ago
Wow> Super hot.