30th April 2001: A short story which was experimental and told of Sebastian’s schooldays. The line, “your arse is tight tonight,” was originally written as, “your arse stinks tonight”, but I toned it down just before I submitted it because I thought it sounded too vulgar.
My first experience of gay sex (other than mutual wanking and other non-serious stuff) came at school when I was 13 or 14. We had a couple of residential assistants staying in our boarding house and they lived on the top floor of the house, with the housemaster having a flat of his own on the ground floor. There were about 40 boys in the house, and I was in the third form. One night I couldn’t sleep because I had stomach ache and I went to find the housemaster. It must have been about 1 in the morning and his lobby light was off, meaning he’d gone to bed. It wasn’t so serious that I wanted to wake him up, so I went back to bed. Just then I thought that maybe Stuart or Toby would have a paracetamol and so went up to find them.
I was really quiet going up the stairs to their shared flat because I didn’t want to wake them if they were sleeping. As I went round a bend on the stairs I could see a light under their door, but I was still a bit worried I’d wake them. The assistants were essentially employed to do sports and duties in the house, being gap-year students – 19 or 20 years old usually. I couldn’t hear the TV or any talking as I approached the door, so I was thinking they’d gone to bed and left the light on, when I noticed that the curtain covering window in the door to their flat was a bit skew so that you could look into the room through a gap. I looked in and it took me a few seconds to work out what I was looking at.
I could see that Toby, who was the shorter of the two (probably about 5’10”) and had blond curly hair, was naked and was kind of squatting on their sofa, which faced the door. He was in a position like he was taking a crap and the look on his face made me think this might actually be what he was doing! Then I got confused because I could see more legs underneath him. These were darker than Toby’s white skin and had black hair on them – Toby was so fair that he looked almost hairless. I figured this must be Stuart who was a dark haired Northern guy, but I couldn’t work out where his upper body was. I was going to leave them to it and remembering thinking I’d take the piss out of them next day, but I was curious to find out what was going on.
I was convinced that Toby was taking a dump because he was in that position, but I couldn’t work out how Stu fitted into this. I saw Stu’s legs moving, kind of up and down like he was doing sit-ups, but even then I didn’t click. They didn’t say anything – they just were in this weird position with Toby looking really uncomfortable.
I saw that Stuart’s hands were on Toby’s waste keeping it steady. Toby’s cock, which I hadn’t really looked at before, was dangling between his legs limply and was much shorter than his balls. I was kind of curious about this because, although I’d seen my mates’ cocks before and my dad’s cock, I’d never seen one on a guy this age (at least not one I could stare at). I was thinking it looked smaller than I’d thought it would and supposed guys cocks must keep growing while they were in their 20s, because my dad’s prick was much thicker than Toby’s. While I was looking (feeling a bit guilty) between Toby’s legs, I realised that I could see something moving up and down behind his dangling balls. This was much bigger than Toby’s cock and looked slippery and wet. Even then, it took me a few seconds to realise it was Stu’s dick.
I wondered what Stuart was doing – why his cock was doing this. I felt really weird when it finally hit me that they were doing the thing me and my mates had joked about other boys doing; that they were buttfucking. As I watched them, Stu’s prick sprang forward between Toby’s legs – it must have slipped out of his arse I guess. From the glance I got it looked huge – much bigger and thicker than anything I’d seen (not that I’d seen many hard-ons back then). It looked a weird dirty cream colour – I later realised he was wearing a condom. He quickly put it back inside Toby’s bum and then resumed his rhythm, again in silence.
By now I was hard in my briefs and, though it felt quite wrong to do so, I started rubbing my dick through the material of my briefs. I didn’t want to take my cock out in case another boy from the house came up the stairs and found me.
The thing I couldn’t understand was why they were doing this. Neither of them acted “gay” at all and Stuart was known to have brought girls from the town back to sleep with him when he could do it without the housemaster finding out. Toby hadn’t had a girlfriend that we knew about, but he was a really good footballer and had played rugby for his university. In fact, I think the sheer surprise of seeing them fuck added to my excitement and has made this an experience I regularly return to when I’m wanking.
Stuart kept pushing his cock in and out of Toby’s butt in a constant rhythm. He didn’t seem to speed up – his thighs seemed to go up and down mechanically. The only significant movement was when Stu pushed Toby’s back further down so that Toby was really bending forwards. Now he looked like he was really straining to take a shit, his face still straining in apparent pain. He held onto Stu’s hairy shins for support. I could now see less of Stu’s cock but more of his face. He was leaning back against the couch with his eyes shut, looking as if he was really relaxed, like he was taking a bath. Apart from the rhythm which his upper body moved to, you wouldn’t have known he was fucking Toby – he just looked dreamy. I’ve thought since that he might have been stoned.
I kept watching, wondering what would happen next, rubbing away at my own cock in my underpants. It seemed to go on quite a while, neither of them saying anything. In fact, only one thing was said and that was just before Stuart came. He said to Toby, quite loudly, “Jesus your arse is fucking tight tonight.” Then his face changed into one which looked like pain but which I recognised to be orgasm. He held onto Toby’s waste, as he slowly pushed his cock in and out of his ass, milking the last dregs out of his orgasm, and then said, in a matter-of-fact way, “That’s me done!”
Toby kind of fell off him, and I became worried that I’d be caught as they might head downstairs to the bathroom to clean up, so I crept away. Afterwards, I lay in bed wanking quietly (so I wouldn’t wake my roommate up) thinking of what I’d seen. Even then, just a couple of minutes after I’d seen it, I couldn’t really believe it had happened – I kept thinking I must have misinterpreted something innocent! Stuart’s final line stuck in memory because it proved that they’d fucked before, and because I found the idea of Toby having his tight arse penetrated really arousing. I felt weird thinking of two guys as I tossed off, as up until then I’d always thought of girls, but it felt good so I didn’t analyse it too much – I just enjoyed it.
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