My Sex with Jake

(Part 1 from 1. Fiction.)

In high school I was a rower and if you’ve never tried it, all you gay boys out there, I encourage you to give it a shot. It’s bloody hard, but working together as a team is an awesome experience. However the best thing about rowing is the outfits…zoot suits, they’re called; tight full body suits that show off that bulge nicely. In high school, every young man was arrogant and loved to pull down their zootie and show off their big buff torso, to show off to the girl rowers. I didn’t do this, naturally – one, I didn’t want to show off to the girlies…and two, I didn’t exactly have the biggest chest around either. I had what you called a “swimmer’s build” – tall, muscular, but lanky and lean. Yet it was very pleasurable to see all the lads prancing around topless, wearing nothing but a tight suit pulled down around to the waist, with the top of underwear visible.

Rowing, as I mentioned, was quite hard work and before we went back to school in my second last year we had an intense pre-season training camp. We drove two and a half hours to some godforsaken lake and unpacked our stuff in one of the few hotels around. We roomed with some of our crew members; I was with Nick, a fairly studly guy in my year, and Jake, who was a year above me. Jake let it all hang out – he flirted with girls everywhere – it seemed like he thought of nothing else but picking up chicks and he certainly didn’t talk about much else either. He was a pretty horny young man and he recounted to us, after we arrived, how the previous week had been the best of his life, as he’d been with a different girl every night. None of us doubted him – Jake could pick up anyone. His chest wasn’t as gorgeous as some (he didn’t have great nipples) but he had a nice muscular upper body – and from that zoot suit bulge, he was fairly well endowed and I imagined him to be a heavy masturbator.

Bedtime (which was strictly adhered to as we had to wake up at 5:30am) was always fun as you got to see the lads down in nothing but their jocks – something I was used to from the zoot suits anyway, but seeing boys in just underwear gave me a better idea of their endowments. Nick slept in loose striped boxers and from looking at him I couldn’t really tell how hung he was. But Jake – well, that was a different story. On this particular night he wore an extremely tight black pair of Playboy boxer briefs, and his cock, hanging flaccid, was bulging out gorgeously. They were skin tight on his ass and he looked absolutely stunning. It was no wonder the chicks went for him!

Anyway, gradually we all went to bed and before long, fell asleep. However at some ungodly hour I was woken up by a noise of some sort. I turned over and saw Jake sitting up in bed, stroking the bulge in his trunks. He was looking at his iPod, for which he had his own portable speaker, and judging from some of the sounds it was making he was watching some straight porn. His eyes were intensely gazing at the picture; they had this pleasurable sort of look to them. Oblivious to my staring, he continued to wank and I could hear him, from across the room, moaning softly. “Hmmm…hmmm…oh yeah,” he whispered, and then did something I had been wishing to happen.

I’d never seen real cock before – not other than my own or my father’s after he’d had a shower. At school lads were very protective of their dicks – it was seen as extremely queer to prance around naked in front of other boys. Thus it was extremely exciting to see Jake pull off his trunks and, after turning off his iPod, start humping his bed, and every now and again stopping to caress his prick. It was decently sized, to say the least – much bigger than my own endowment. My hands soon reached for my own cock, which was already semi-hard – it was fascinating to watch another young man wank like this.

Jake continued stroking and humping, and occasionally had bursts of great energy, where he would pound the bed ferociously. It was a wonder Nick hadn’t woken up, all the groaning and other noise he was making. I didn’t dare make a sound, though – I wanted to see this guy blow. After half an hour, at least, Jake decided to stop, and put the trunks back on. He needed the iPod to finish himself off, I figured. I was right – after a few minutes of intense stroking, and some loud female moaning from the iPod speaker, Jake let out a long, deep groan and I saw fluids appear out from his trunks. His orgasm seemed to last a lot longer than my wanks – wave after wave of his spunk came pouring out. He seemed very satisfied – he massaged his chest in pleasure and I could see him smiling in contentment. Although I was rock hard – I decided not to follow Jake’s lead and take a wank – he would notice me and I wasn’t like Jake – I can’t say I was one who would let it all hang out.

The following morning we rowed hard and then had to run back from the lake to the hotel, which took a good fifteen minutes if you were going quickly. I had noticed after the training session, when Jake pulled down his zootie, that he was wearing the same underwear as last night. The notion that the sweat from this sexy young male was now mixed in with his cum was extremely arousing, and I had to make sure I didn’t get a boner as it would have been highly visible in my zoot suit. Anyhow, once we had run back the coaches announced we had a long break, and wouldn’t be training again until late afternoon. Most of us were pretty knackered and just wanted some sleep. We decided this was the best idea and after taking quick showers and changing we lay down on our beds and dozed off for a while.

I woke up again at about 3 o’clock, and my roommates were still asleep. I had had a nice dream about some guy in tights and was feeling pretty sexy – my cock was semi-hard in my briefs. I hadn’t had a wank the entire training camp – and this was certainly a good time, whilst everyone was knackered and asleep. I decided to nick off to the toilets, when I spied those black Playboy trunks sitting on the floor next to Jake’s bag. The thought of wearing his underwear, which he had wanked in last night, turned me on so bad; making sure no-one would see, I suavely picked the shorts off the floor and headed into the toilet, where I locked the door.


***

I quickly undressed and slipped the boxer briefs over my throbbing cock. They were just as tight as they were on Jake, and they made my hard-on look especially big. I had never had the pleasure of wearing such a gorgeous pair of underwear, and the fact that Jake had worn them wanking made it all the more arousing. I took them off and sniffed them, taking in the manly scent of his juices and sweat. It was better than any fragrance I had ever smelt – knowing that Jake’s monstrous cock had exploded inside these little trunks was so pleasurable, and I decided that more than one type of cum would reside in these briefs. Already incredibly close to orgasm, I slipped the briefs on, stroked my little boy hard and fast, and thought of Jake last night, massaging his pectorals as he came. It was all too much and I reached the point of no return. My eyes rolled into the back of my head and my schlong burst out with cum, wetting the jocks just as much as Jake did last night. I made sure I had let out every last drop and then opened the door, still wearing Jake’s undies – only to meet Jake standing right in front of me.

He was wearing a different brand of underwear this time but it was just as tight fitting and his cock looked as gorgeous as ever. What wasn’t quite so sexy was his facial expression – he looked as if he was about to kill me. He grabbed me by the shoulders and pushed me against the bathroom wall, after locking the door.

“You wanking in my jocks, fuckhead? Queer bastard? Always thought you were, lanky queerie.” He gripped me hard – I could barely move.

“I can explain, I can explain this,” I said, panicking.

“There’s nothing to explain, I know what you were doing. You just jacked off in my undies, you gay little bastard.” Then he did something totally unexpected – he kissed me on the mouth. And it wasn’t just a kiss, either, it was a full-on pash, something I’d never had from a girl, let alone a guy. Our tongues wrapped around each other and we kissed passionately; it was like something out of a movie, our lips on fire. I had only just wanked but already I was becoming very aroused again and interestingly, so was Jake. I could see his cock sitting quite hard in those small boxer briefs he was wearing. He broke off the kiss suddenly and brought my hand down to his crotch. “Want this up your ass?” he said enthusiastically, in that typical Jake style. I had absolutely no idea what to say – of course I did, but what if this was some kind of a set up, to expose me as gay? I figured that nobody would go to such lengths to do such a thing – thus I told Jake I was totally up for it.

He grabbed some soap from the shower and, after pulling his own underwear off me, lubricated my ass, talking to me casually as he did so. “I think I’ll practice on you, Willy, so then I can do it doggy style with a chick.” He laughed as he said this; I wasn’t really paying attention – I was already in heaven, about to lose my virginity to a gorgeous, horny young hunk. I felt a sudden jolt when I realised he was probing my ass with his fingers. It felt pleasurable but slightly painful simultaneously. He added more fingers – two or three, and the pain grew greater; I moaned slightly but Jake stopped me – he put his hand over my mouth and massaged my ass with his other hand. The caressing calmed me down a bit and the pain soon passed.

“Okay, Will boy, I’m going in now.” And I first experienced the pleasure of a guy fucking me. He slowly pushed his cock up my tight fuck hole – I was bending over and facing the mirror and I could see Jake, in heaven, moving back and forth, in and out of my ass. The pain had gone and the pleasure was indescribable. I wanted to feel his flesh – get hot and sweaty and release a monstrous load together. I motioned for him to lie more on my back – he did so and his rhythm and motion intensified. The way he was pumping me was faster than I had seen on any porno – it was so quick in and out that I couldn’t feel anything other than a constant stream of pure, passionate pleasure. I whispered to him that I was climaxing and he told me to go for it. I pumped my dick as hard as I could, and the thought of Jake riding me as well as the wank I had had just before culminated in a monstrous orgasm – my cock spurted out torrents of juice – yet the pleasure continued as Jake was unrelenting in fucking me. He increased his rate even quicker and I recognised at once that he was about to blow. “Moan for me Will, moan for me…” he whispered. I let out deep, erotic groans and soon I felt the sensation of a man orgasming on my back – his seed planted inside me, his sweaty, sexy body sprawled over mine. My cock was already stiff again. I motioned to Jake that I wanted one last blow – he obliged by kneeling down and massaging my cock with his tongue. For a straight guy, he seemed to have experience in this kind of area. I touched his head and motioned for him to quicken up – and soon I released my third lot of cum for the afternoon, right down Jake’s throat. I had just had the most heavenly experience of my life.

We stood up and I got a better look at his cock – it was flaccid yet still big and wet with juice. We didn’t really say much – I gave him back his briefs, we both gave our cocks a wipe with an old towel, and pretty much went straight back to lying down. As far as I know, Jake never told anyone about that horny afternoon – it was probably pretty insignificant to him in comparison to his other sexual experiences – the only difference was it was a guy, not a girl that he was fucking. But I certainly never forgot it – and at the end of rowing camp, he gave me, quite discreetly, that pair of Playboy boxer briefs that I had so admired on him, still with his and my cum stains inside – to this day, I wank in them quite often. They’ve been washed, since, naturally, otherwise they’d disintegrate – however I still reckon I can get the scent of Jake’s blissful cock and his hot wet spunk whenever I give them a sniff.

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