Awake with Jake Pt. 02

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I continue telling my dad about my first time with a guy...
8.8k words
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Part 2 of the 4 part series

Updated 09/22/2022
Created 05/09/2014
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"You shouldn't have poured me that much," my dad said the way he always did after I'd already brought him a nightcap.

"There's a funnel in the cupboard," I reminded him. "I could pour half of it back into the bottle."

"Ooh no!" he winced. "You can't mix poured whiskey with unpoured. I've told you that before."

You certainly have, I thought. On many, many occasions.

I sat back down and poured the top half of a bottle of beer into my glass. It made the sort of head that would get me sacked if I worked in the union bar, but I had plenty of time to let it settle.

"So did he get to try rimming you?" dad asked, swilling his whiskey and ice cubes around in the tumbler.

"Whether he liked it or not," I replied with a smirk.

At first he was reluctant. He kept trying to pull back and coughing and spluttering. I'm not saying I forced him, but I had to push my butt-crack into his face quite insistently and hold his head steady with one hand before he would lie still for long enough to see what it was really like.

When he did, though, he quickly found that he enjoyed it far more than he expected to. His muffled objections turned to surprised mutterings and eventually, as his nose started sniffing and his tongue started licking, grew more emphatically into eager grunts.

I gasped in appreciation: so this was what it felt like. This was what my dad had found so incredible that he'd taken his profile off the dating websites he used to try to meet women on.

Marcus didn't feel ready to penetrate me with his tongue, but he enjoyed getting his face stuck into my backside with very much the same enthusiasm as I had with his.

"And how did that feel?" my dad asked.

"How did it feel the first time someone did it to you?"

Dad peered up towards the top of the curtains above me, looking like he was studying the way they were hanging but really trying to remember the occasion that had happened. "I think that was when I was being fitted up for a pair of trousers," he muttered with a small, almost nostalgic, smile. "It was certainly very pleasant, I remember that much."

"Well, it felt pretty good to me, too. I think, though, that I enjoyed rimming more than I enjoyed being rimmed."

"Me too," dad said. "I've always taught you that it's better to give than receive."

Most of the pleasure for me, squatting over Marcus as he lay on my bed, was how unutterably naughty it was for us to be doing this together. It was a nice sensation - don't get me wrong - to have another guy's tongue lapping into my butt-crack and exploring up and down it, but it was more the act of what we were doing together that made me feel excited enough to want to jerk off.

Marcus was pumping his dick fast and hard like a piston. As his tongue swept up and down the full length of my cleft, tasting my different flavours from what Craig had called my taint right up to where the wiry hair in my crack petered out to become a softer fuzz, his hand was whacking his cock off as fast as he could. He liked to beat off really quickly - I knew that from when he'd stayed over before.

We'd ended up wanking off together one night after staggering back from town, not exactly rat-arsed but definitely a little worse for wear. As we'd pulled our clothes off, the fronts of our underwear had made it blatantly clear that we were both horny and, as we'd lain side-by-side in my bed with two obvious mounds lifting the duvet, one of us had suggested - him, I think - that we jerk off before sleeping.

I'd quickly agreed and we'd yanked down the fronts of our underwear and soon the quiet of the room had been replaced by the double drum beat of our fists against the duvet. Marcus' rhythm had quickly sped up from a quiet stroking to a loud hammering so fast and so strong that the cheap bedframe had started shaking and creaking.

"What the fuck are you doing, mate?" I'd asked him, pumping my bigger dick at more leisurely pace.

"I've always wanked off like this," he'd said, frantically slamming his hand up and down his shaft.

"But you can't enjoy it if you're just beating it up and down like you're shaking a fucking bottle of sauce!"

"I'm not doing it to enjoy it, Jake!" he'd laughed. "I'm doing it because Annabelle's had her tits in my face all night and now I'm hard as fuck and I need to spunk up before I can sleep - that's why I'm doing it!"

The bed had been making a noise like a lumberjack sawing logs. My flatmates would joke next morning that they'd heard us ending our night by boning each other's arses on my bed. It had seemed kind of funny at the time and it was even funnier in retrospect, since by the end of that term, the two of us were ending a lot of our nights by doing precisely that.

"You wanna take it easy, Marcus," I'd advised him as my own fist worked at myself at about half the speed of his. "A good wank is something to be appreciated... like a fine wine..."

Realising how much like my dad I sounded, I quickly added, "or some such shit!"

"Oh God yeah!" he called out, and I thought for a second that what I'd said had come as a welcome revelation. But then the smell of our cocks being jerked was joined by a more acrid odour and he said, unceremoniously, "Pass me something to clean this up with, mate."

After wiping himself down with one or other of our discarded socks, he'd turned over to face the wall and asked that I hurry up to finish off 'enjoying' myself.

With him lying underneath me, licking up and down my arse-crack and whacking himself off with that same, relentless rhythm, I felt compelled to reach over and steady his wrist and to tell him that I would show him a better way.

This was like Craig teaching me: now I was going to teach Marcus about how to pleasure himself.

He took his hand from his cock and I replaced with my own. I caressed it as sensually as I could, stroking my fingers up and down the shaft and enjoying how hard it felt throbbing against my skin.

I wet my thumb with his precum and worked it across his helmet-shaped head, making it slick and shiny and then adding a gob of my own spit to help lubricate his shaft. I worked my fingers right around his organ, making it as silky and slippery as I could, and he groaned to show his enjoyment as he kept flicking his tongue against my arsehole, egging me on as I took up a slow and deliberate rhythm on him.

I was actually surprised how much I liked it: there was a lot more to a dick than there was to a pussy and the sharp smell from its head was strangely appealing. I stroked it steadily up and down, kneading his balls with my other hand. The skin of his scrotum was soft and yielding and the paired mounds of his testicles inside it were larger than Craig's had been.

I'd always treated masturbation as a sort of art form, always keen to try out different approaches on myself and fascinated to find out how better to arouse my cock. Now I applied the same approach to Marcus' dick, stroking him in varying ways to find out what worked for him and trying to refine any techniques that he enjoyed. Once I'd figured out what he liked, I smiled as his organ swelled up to its full, impressive hardness and marvelled at the way the head of it started gently pulsating against the swirling patterns I was making with my thumb.

The best part was that it was making my own cock throb just as hard against my stomach. Who could ever have believed that wanking another lad's knob off could be so much fun?

But then, I suppose it was kind of obvious that it would be actually. After all, I'd always greatly enjoyed playing with myself - right from that very first time after my dad had explained to me how some weird-sounding activity he called "masturbating" was supposed to work.

He seemed to find it all very embarrassing, as he usually did when he talked our "private parts", and I hadn't really been able to work out what the hell he was on about the way he'd couched things in convoluted language and dressed things up so much.

I could figure out that there was some connection between a recent spate of wet pyjama bottoms I'd had to dump in the laundry basket each morning and whatever it was he was saying I had to do with my willy. Something about "manipulating" it each night before I slept - the way he was moving his fingers up and down in the air between us and talking about my foreskin made me snigger a whole lot more than I understood what he meant.

Finding it difficult to get to sleep that night as I was being hassled by a hard-on that just wouldn't give up, I heard my dad come up the stairs to bed and had an idea. Perhaps this "masturbating" thing he'd been talking about might be something he sometimes did to his own 'private parts' before sleeping. It was possible that if I snuck a look at him, I might find out exactly what he meant by that weird up and down hand motion that had so embarrassed him.

I crept along the corridor between our rooms after I'd heard him lie down on his bed so I could take a sly peek at what he was doing. I figured that the noises I sometimes I heard at night when my boner was stopping me from getting to sleep - a sort of gentle thumping sound which was usually followed by the same smell as the stuff that had soaked my pyjamas - must be him doing to his own dick whatever it was that he'd been saying I should do to mine.

That same noise was going on tonight. It had started up just after I'd heard him lie down on his bed. A low, gentle rhythm which was getting steadily faster.

I've often wondered if he knew I was spying on him as he masturbated that night. I've never felt able to ask him, but I've sometimes thought that maybe he felt more at ease to show me how to jerk myself off than he had trying to explain it to me in his half-cocked way.

He'd left his door open - which wasn't so strange - and his light on - which was - and he was lying on his bed with his pyjama bottoms around one foot, and I'd figured when I'd seen him splayed out like that, that maybe he was making a show of what this 'masturbation' thing should look like and hoping that I'd learn from what he was doing.

I couldn't see his face from where I was standing, so I don't know if he saw me there. All I could see was his knees, bent and spread open, his whacking great dick poking upwards between them with his hand sliding quickly up and down it, his bollocks thumping around and looking grotesquely swollen and, beneath those, the hairy crack of his arse between his open thighs.

Not the most flattering angle I'd ever seen him from.

The first thing that struck me was what a massive cock my dad had. For a modest, quiet bloke who always got so embarrassed about nudity, he was lying there stroking a piece of meat that looked big enough to have its own postcode. I mean, I'd known it was bigger than my friends' dads dicks - I'd got to glance it a couple of times - but now standing here and being able to look at it properly, the thing which had helped to produce me way-back-when seemed ludicrously huge - almost impossibly proportioned. It wasn't just long but it was so damn thick - the sheer girth of it meant he could hardly get his hand around it.

I immediately wanted my own dick to grow as big as his, which in time, thankfully, it did. I knew it'd be a struggle to fit something that big inside my underwear, yeah, but just think of how awesome it would be to lob something like that out in the locker rooms after PE and how other guys would be so jellied when they saw what a humungous fuck-off monster cock I had swinging between my legs.

It was the head of the thing that most fascinated me. Apart from how huge and bloated it looked - right then it looked to me bigger than the whole of my own cock and balls put together - its surface was wet and shiny and its colour a deep, dark purple. It was almost scary, the way it looked, like something weirdly alien, throbbing and glistening and weeping a steady trickle of clear, thick liquid every time my dad's foreskin swept back and forth across it.

Anyway, I just stood there watching him slamming his fist up and down his enormous shlong, wondering if he was maybe showing me - without actually stating that he was showing me, of course! - how a guy masturbates. It looked pretty gross, with all the wiry hair and his saggy bollocks and that deep sweaty crack between his arse-cheeks. But I figured that if he was trying to teach me something, I should do my best to watch him and learn from whatever it was he was doing to himself.

You sort of grabbed your foreskin and slid it up and down the shaft of your cock, doing it faster and faster until your balls were bobbing around.

It suddenly occurred to me, from the shape and movement of his hand, that this was what some of my mates had joked about and called 'wanking off'. It sounds stupid but I hadn't realised until then that the thing my dad had talked about as masturbation, and said we should be open and honest about even though he was barely even able to say the word without blushing, was the same as what everyone else called wanking.

Wow! So this was wanking, was it? And here was my dad wanking his dick off right in front of me!

So my dad was a wanker, was he? I smiled at the realisation.

Okay, so to wank yourself off - or masturbate, as my dad would say - you kept jerking at your foreskin, pulling really quickly across your bell-end and then sliding it back upwards, all the time speeding your breathing up until you were panting like a dog.

I wasn't sure what the point of it was - it seemed way too much effort for me to want to do it to myself.

I felt for my own dick and found that the boner that had been keeping me awake was still going strong and was sticking upwards through the fly of my pyjamas. I was surprised that having to look at my dad's saggy nuts and sweaty butt-crack hadn't softened it, but there you go.

I wrapped my fingers around my hard-on - it seemed so small compared to my dad's - and yanked the foreskin up and down it a few times like he was doing. I was blown away by how good it felt - especially when I held it really tight and jerked the shaft of it quickly.

So that's why guys wanked their dicks off, or masturbated as my dad would say. Because it felt nice.

And obviously my dad thought it felt nice too, otherwise I wouldn't have heard him doing it so often.

I wondered if he actually did this every night; if he would lie like this wanking off while I was in bed in the next room. I thought he probably did. Every time I'd been awake this late I'd heard this same dull thumping sound coming from his room.

My dad wanked his knob off like this every single night! He came up to bed and lay like this, pounding his hand up and down his colossal beef-pole!

Wow... just, like... wow!

I had another thought: maybe that's why the thing had grown so huge...

I watched him grab his bollocks and gently fondle them while his hand whacked faster and faster up and down his huge shaft.

Was that part of it too?

I tried it on myself - yeah, that felt pretty good. One hand rubbing your dick, the other playing with your knackers.

My dad was teaching me how to masturbate and he obviously knew his subject really well! After all the years he'd been lying here like this, jerking himself off every single night, I supposed it was little wonder.

He suddenly grunted like a tennis player - it seemed strangely out of character - and then long white strings of liquid started shooting from his cock. At first I was a bit freaked out - what the hell was that stuff? - but soon I realised, mainly from the smell, that it was the same liquid that had been soaking my pyjamas each morning for the past few weeks.

I mentally joined the dots with what we'd done in Biology and figured out that this was my dad's sperm. I was actually looking at the stuff that had, at least in part, produced me! So many millions of tiny little sperm cells just like the one that I'd come from and there they all were, squirting out of his cock!

How cool was that?

Again it occurred to me that my mates had a word for this. I knew that when a guy wanks off for long enough, he eventually spunks up. So I figured I was watching my dad spunking up. Part of showing me how to wank had been to show me what it looks like when a guy spunks up.

I felt pretty flattered that he would let me see this. It was obviously extremely personal - secret, even - and yet here he was doing it in front of me so that I could learn from watching him. I would never have thought someone as uptight as my dad would let me see him releasing sperm - let me watch his actual white jizz as it shot out from his cock - but here he was releasing a pretty massive load all over himself while I looked on.

Once his spunk had stopped shooting and the last few spurts were just kind of oozing out of his slit, his hand slowed down and eventually stopped its pumping.

So that's how it worked, was it? You got all your sperm out from your balls and then you stopped jerking your dick. In that order. This was all good to know.

I could see how making yourself spunk up like this was better than it happening in your sleep. It was just as messy but at least it could be controlled and more easily wiped up. I noticed my dad had tissues on his bedside table at the ready for this specific purpose - and there was me all these years thinking his nose must really run in the night!

Assuming the lesson was over, I crept back to bed and tried out what I'd learned for myself. I left my bedside lamp on in case my dad wanted to take a look in on me. He might want to check out that I was following his lead correctly and doing to my own smaller dick the same stuff that he'd just done to himself.

I lay on my bed with the covers pulled back and enjoyed my very first hand-job. I thought my dad would probably be proud of me if he were to see me like this: masturbating myself in the way he'd just shown me. It was like I was becoming a man, starting to wank my dick off just like my dad obviously did each night.

Girls at school around that time would get together to have 'period parties' as a sort of celebration that they'd reached womanhood. I liked the idea of me and my dad having the male equivalent; getting a few mates around to have... I dunno what you'd call it... a 'jerk-off jamboree' maybe?

I have no idea if my dad looked in on me: he went to the loo which is just along from my bedroom door so he might have done. If he had, I hope he liked the sight of his little Jakey with his back arched upwards tugging away at his pud for the very first time. He would probably have seen the look of pure enjoyment on my face as I realised, just as he once had in his own bed at my age, how utterly fantastic the simple act of pumping your own hand up and down your cock was. I hope he stuck around for long enough to see my surprise and excitement when my own gloopy strings shot out from my bright red bell-end and covered my chest; to smile at how my outpouring was less copious but just as odorous as his own.

Getting back to the story - and I'm sorry I keep drifting off like this but I hadn't realised how difficult it would be to write about this kind of stuff - my dad took a drink of his whiskey and winced at the strength of it.

"More ice?" I suggested.

He smiled. "It'll be okay."

As I took a drink from my beer, he asked, "So what did you do while he was rimming you?"

I put my glass back down and replied, "To be honest with you, and I don't really know what possessed me, but I ended up bending forwards and sucking his dick."

He grinned broadly. I could see in his eyes that it really was pride he was feeling that I'd been able to just let loose with Marcus and do stuff with him that my dad wouldn't have been able to at my age.

It seemed strange that he'd be proud that his son was a cocksucker, but that was what he was like these days. He could be such a weirdo but he'd do really inappropriate stuff in such a polite and well-mannered way that he could kind of get away with it.