Alright,
So in the middle if high school (a boarding school) me and this friend of mine who from now on we’ll call Jack used to watch porn together and talk about girls etc. Jack is around 6’5 but skinny. Dark brown hair, slightly tan. Handsome in a kinda boyish way? I don’t know exactly how but somehow we broached the topic of trying stuff with guys and nervously but excitedly managed to suggest trying it with each other. I don’t know why, but basically ever since puberty I’ve had a fascination with penis size and the masculinity it entails. So I very early into our conversation (this was over text) asked him how big he was. He told me he was very big which turned me on so much. When we got back to our dorm, I snuck over to his room in the night. He was waiting for me in just his briefs and I could already see how huge his bulge was. My mouth watering, i knelt down in front of him and pulled them down. It literally did the thing like in the stories where it sprung out and hit me on the face. It was fucking huge. Slightly curved, enormous balls, long, thick and smelt delicious. I can also say he cums like a fire hydrant. At a later date we put mine on top of his for a comparison and you could literally fit 3 of mine into his in terms of volume, and I’m a very standard size. I won’t go into much more detail on that side of things because that’s now what this website is about, but I will say firstly that it turned me on so much I came just from sucking him without being touched myself, and secondly that I’ve never been interested in sexual stuff with any male other than him, which leads me to believe it must purely have been some kind of psychological thing about the size of him.
I’d panick and get ashamed afterwards, but that went away after a while, and I told him about my cuck fantasy. I still have a few messages on the topic from more recently, but I deleted the bulk of them a while back in a fit of embarrassment and shame. He’s talked to me about fucking my girlfriend’s big tits, fucking her in front of me while I have to sit in the corner. We also talked about a teacher that we both thought was hot. We imagined her keeping us after class and making advances on us, but when she saw how much bigger his cock was than mine, she pushed me away and told me to just watch. That kind of thing.
But the main thing is my mother. When I told him about that he was more than happy to talk about it. He said he’d always thought she was a milf, and she is. She used to model a bit in her early 20s. He used to talk about coming over to stay at my house and using my mum’s bathroom so she’d see his monster cock and be unable to look away. That he’d go into her room after I’d gone to sleep, and I would be able to listen at the door to my mum giggling and moaning his name. He also talked about me having a party, wondering where he is and then hearing moans from my mums room. I’d open the door to them fucking doggy and my mum would yell at me to fuck off because she was busy. A highlight for me was seeing him purposefully flirt with her at an event when we were near graduation, stealing glances at her ass and tits, standing so tall over her. When I was leaving school some time for a term break I remember him saying ‘say hi to your mum for me’ and getting slightly hard just from him saying that. To make it even better when my mum was looking at my year book she said ‘Jack is a very nice looking boy isn’t he?’ I jacked myself silly that night.
Let me know if you have any questions or want to speculate as to what they might have got up to. I’m also gonna post some messages with names blurred out, including messages with a girl who he slept with telling me how amazing he is in bed and how big his cock is. Sorry if this wasn’t very substantiative but it was some of the hottest stuff that’s happened in my life.
