Matt picks up the story....
I've always liked looking at guy's bodies ever since I was at school, and I sorta drifted into gay activity in my last years at college. I'm not bad looking - even if I do say so myself - blond hair and a good physique , but I was always very shy, and now here I am at 21, still as shy, but boy, do I love cock!
I lost my folks when I was quite young, and was brought up by Alice - an old friend of mum's - who loved me dearly, and did everything humanly possible to make my passage into manhood as smooth as possible. But she wouldn't have understood what I was talking about if I'd told her I was gay; she'd think it was something I'd grow out of, like spots, or a fad of some sorts. She had no idea how, every night, I'd lie there in my bed, furiously masturbating over the memory of some boy I'd seen on the beach, or on the block.
For sure she wouldn't have understood my attraction to Jack.
Jack was an old family friend who'd been very good to us when I was left alone, and he sort of took me under his wing. He was dark-haired, real muscular, with black chest hair that used to pile out around his open-necked shirt. He was just great to be around, and we'd fool about like two very close friends, like go exploring in the woods after a picnic, or mock-wrestling on the beach and I found I always got a hard-on when I was close to him.
I had no idea how old he was, though I knew he was a lot older than me.
I'd never dared talk to him about my feelings for guys - I'd just assumed that as an adult he wouldn't understand. I was real fond of him and of being in his company, so much so that I used to think about him sometimes when I was in bed, and then I'd find myself getting hard - so hard that I just had to jerk off to relieve the feelings. You know those erections that you realise aren't going to go away on their own?
I never got just a piss-boner when I was thinking of Jack - I'd have dirty, horny dreams where he and I would be together, on some desert island and naked, and we'd wrestle for hours - like I used to see in some of the old Colt magazines that I'd started collecting.
We'd play grab-ass and he'd touch me in all those places where I love to be touched, and he'd run his fingers up the crack of my ass. And then we'd stretch out on the white sand, letting the cool breezes blow over our hard cocks.
He'd kiss me full on the lips, and I'd run my hands over his tanned, muscular body as the surf rolled in over us, then I'd tried to imagine him fucking me, but the frustration almost drove me mad. When I dreamed those dreams, I'd shove the duvet way down the bed and open my legs wide, spread lube on my cock and slowly masturbate, gripping myself tighter as I jerked, while I ran my hands up and down my chest and stomach, revelling in the feel of my hot flesh. Then I'd cum, and I'd aim my cock-head towards my face, and sometimes, if the dream was a real horny one, I could get a splash or two on my chin.
Anyway, after college I went to work for an insurance company, which bored the fuck out of me, but it was a steady job and occasionally, when I had to go meet a client - it was usually a guy - he'd sometimes hit on me, and despite my shyness we'd end up fucking and rolling around on the marital bed while his wife was out.
All in all, it wasn't so bad but I rarely made the first move.
I taught myself to take cock up the ass when I was in my late teens, simply by buying a large dildo on a trip out of town - it had to be done because of the embarrassment if I'd got into a situation where I was supposed to take it in the ass, and I didn't know what to do, or worse still, couldn't take it because my ass would stay clamped shut through sheer terror.
So after bought the thing I locked myself in my room, and laid out the dildo and lube on the bed while I stripped off. There's something almost sinful about what I was about to do in the middle of the afternoon, naked in my room. I placed some towels over the duvet to avoid any mess, then I lay back with my legs in the air, while spread some lube around and inside my sphincter ring.
Then I lubed the dildo.
I closed my eyes, as if pretending it wasn't my hand holding the dildo - in fact, pretending that it wasn't a dildo at all, but some stud's cock resting against my ring. I pushed and it entered me, so I pushed a little more, then a little more, and then a sudden pressure built up in me that made me gasp out loud, and my mouth opened wide almost of its own volition. But I didn't remove the cock. I left it where it was for a second or two to catch my breath, until my ass became accustomed to the invader, and then I pushed again. My body filled - there's no other way to describe it, and I pressed myself further back into the bed, my legs spread as wide as possible as I relentlessly slid the rubber cock deeper and deeper into me.
It was then I felt my body actually start to suck it in, so I grabbed the shaft quickly, as I didn't want to risk losing it inside of me, so I determined to keep a few inches free of my body.
At last it was there, as far in as I dared push it, and I lowered my legs. The cock had a tendency to try to slide out, so laying flat on the bed kept it in place, then I rolled over onto my side, and held my hand behind me tightly over the exposed end.
I let Jack's face drift into my mind's eye and started to masturbate. I'd never before felt this sort of invasion of my body and it gave me a real charge. There was quite a bit of pain initially, though not all of it unpleasant, and I became to determined to master the art of fucking my ass, for my own pleasure as well as for the benefit of future potential lovers.
My hand jerked faster and faster on my distended cock, and then I realised that sweat was flying from my face and body after all my exertions as I worked on my meat, and I found that I couldn't seem to stop my lips pulling back as I bared my teeth in a silent snarl of lust. I snapped my head back as the desire to cum rose within me, and soon all I was aware of was a high sexual presence in my ass - all pain had gone.
I came, bucking and shuddering, cum splashing in an arc onto the strategically placed towels, in an almost endless stream, and then I was acutely aware of my ass clenching, rhythmically, on the dildo, in time with the pulsing cum.
Then I rolled onto my back once more, raising my hips to let the dildo slide lazily out and into my waiting hand, and I placed it on the towels.
I felt my ring.
It had been well and truly stretched, but I knew it would soon regain its elasticity, and be puckered up for the next time I practiced. And regular practice was what I fully intended to take care of. I repeated this procedure every evening for a month or so, and the sexual pleasure enjoyable grew more intense the more I fucked myself, and soon I was longing for the time when I'd have a real man's cock there instead.
Now that I felt more confident, I started to go to a gym just outside town, to build up my pecs and abs. It was one of those all-glass places you see nowadays, which looked completely out of place in the countryside round where I lived, but they had some neat equipment, and I guessed I might strike it lucky at some stage, judging by the looks I got from some of the guys.
The first session I went to was real quiet, and I ended up wandering idly around the place for company, to discover that there were only two other guys there that day. They were in the rest room giving each other 69, so I figured it best not to interfere or join them, but it was on my third visit that I really struck gold.
I was in the showers after my workout and a couple of well-hung guys came in - they were both a lot older than me, but real lookers, with those body-builder muscles. The one nearest where I was showering winked at me as I soaped up. I smiled back.
'Hi, I'm Max', he said, holding out his hand.
I shook it.
'Matt' I said.
'Pleased to meet you, Matt,' he waved to his companion. 'This is Dave.'
I nodded to Dave.
'Would you be interested....'
He paused as he spoke and looked round the room, but there were only a few people outside by the pool area.
'...in a little fun?' he went on.
'Depends on what you have in mind.'
I couldn't believe how that came out.
Obviously I was losing some of my shyness.
'I know a quiet corner where guys can have a real cosy time,' Max continued, winking at Dave. 'Get my drift?'
'Lead on,' was all I heard myself say.
We turned off our faucets and Max grabbed his towel, then led the way while Dave and I followed on. Dave rested his big hand on my naked butt as we walked, his erection bouncing heavily before him as we negotiated a few bends and stairs. Then we started to descend to a darker area, which eventually became, virtually pitch black. Every nerve in my body was screaming at me to leave, but my cock led on, as always.
I could sense that there were other people around, and then realised that I was standing on a cushioned floor.
This was obviously the 'rumble room' that I'd overheard one or two guys mention. A hand pulled me to the floor and I felt a cock against my lips. I eagerly opened my mouth and licked one huge head, already leaking and oozing. It tasted sweet, and then the ooze was followed by a slightly faster stream of pre-cum. A hand gripped the back of my head, and the cock entered my mouth slowly, an inch at a time.
I felt other hands on my butt, and slippery fingers running up and down my ass crack. Others had obviously now joined us because there were too many hands for it to be just the three of us, and then a cock poked at each side of my head, so I turned to lick and suck them in turn, still very conscious of things happening around my ass area.
A cock was nudging at my sphincter ring, and a feeling of sweet relief swept over me as I realised that I was at last going to be fucked by flesh and blood, and I pushed my butt back against the cock, which slipped in, deeper and deeper, and once again I experienced that 'full' feeling like when I'd first used my dildo. I relaxed and took a deep breath - well as much of a deep breath as I could with a large cock in my mouth - trying to picture Jack's face in my mind. Then the cock seemed to flow all the way in and I felt the guy's warm belly against my ass.
We were all moving together now and I sucked on each cock as it was presented to me, listening, fascinated, to the appreciative voices around me.
'Oh, baby...suck that cock...yeah!!'
'This boy was born to SUCK!'
One of them came in my mouth quite quickly, and I munched on his cum while another one pushed forward and took its place.
I was real excited now.
This was a dream come true, and the guy fucking me was now slamming at me, his balls slapping against my ass. Then he gave a mighty heave, slapped my ass cheek, as he shook against me, then I felt the hot sting as his semen filled my ass. I couldn't believe the heat of it, filling my guts, but I was almost delirious at the fact that I'd been initiated into being a cumulus!
He kept the rhythm going for a while as he emptied his cock then gently withdrew and patted my butt, leaving a cool place where'd he'd nestled his meat. Now someone replaced him, and this was a biggie - I had to flex my ring around that love-muscle so he could ease into me, but he made it and was soon riding me like a champion.
The air was thick with the smell of cum and sex and maleness, as more and more hands stroked me. I lost count of the number of blowjobs I'd given and I'd stopped bothering to wipe my chin, just letting the loads drool down onto the floor,
Cleaning up wasn't my problem.
Again my ass was pumped full, and again the cock was replaced, and the afternoon wore on. I'd lost track of time, and my name, and where I was. I was a fucking machine, kneeling and having cocks fill me and then leave.
Finally, the last load pumped into my mouth and the cock departed, and...nothing. I rolled over and lay in the large lake of semen, my cock still hard and straining. No-one had bothered to take care of my lust, so I slid my hand down and grasped my flesh, feeling the needful throb beneath my touch and thought back over the session. My mouth and face were bathed in cum, and it sloshed around between my teeth, and my ass was leaking copiously onto the floor as though a valve had been opened.
I gritted my teeth and masturbated.
A shiver within me grew, then took over my whole being as I whacked faster, until I felt - rather than saw - my cum shoot from me, and spatter somewhere over there in the dark.
This was definitely a session to remember and to jack-off to!
I drove home, after a final shower, feeling every nerve-ending tingling, and my senses alive at last. There was a dull throb in my ass, and a longing for fulfilment again.
Alice was out when I got back home, which was just as well - I'd sucked so many cocks that I figured I must have a speech impediment by now. She'd left some supper on the stove, and then I saw an envelope by the phone.
It simply said 'Matt', so I tore it open and read the note.
'Dear Matt - I hope you had a god time today. I have a surprise for you. Jack phoned. He's in the country for a couple of weeks and wants to catch up with you. I've invited him for a picnic tomorrow if the weather is OK. Love, Alice. PS If you what to talk to him, his phone number is....'
I re-read the mote just to make sure I'd not got it wrong. He was here. Jack was here!
I sat down on the stairs and winced slightly, My ass was still recovering from the pounding it had received earlier, and my cock rose at the thought of seeing Jack again. I picked up the phone and dialled the number Alice had left me.
Come on, Jack. Come on...
That deep brown voice sent my cock stretching down the inside of my slacks.
'Hello?' the voice said again.
I gasped into the phone.
I could hardly speak. This was the same sort of breathless pleasure I'd got from that dildo inside my ass. My head pounded and all cogent thoughts scattered themselves to the four winds.
'Is that you Matt?'
I gripped the phone and wondered if Jack was doing the same.
'It's great to hear your voice again, Matt,' his voice oozed cum-honey as his tongue slid down the line to lick in my ear.
'Who...what are you doing back here?'
'I had a hankering after a home visit, 'Jack said. 'Alice told me that I could come and stay with you both while I'm here, and she's even invited me on one of her picnics. What dye say to that?'
'It'll be like old times,' I answered.
'Not quite. You're all grown up now,' he went on. 'You got time for an old guy like me?'
If you only knew, Jack. If you only knew.
'C'mon, Jack. What are you? 30 something?'
'I bet you're a lookers.'
I blushed as he said it.
'Hey, I joined the local gym,' I said suddenly. 'You should give it the once-over while you're here. I can take in a guest.'
'I've had some fun in gyms,' Jack laughed that warm laugh. 'Stay away from the dark areas!'
I laughed too as I thought I should.
I was tempted to get my cock out and whack off, but Alice might some back any minute.
'I don't know what you mean,' I said coyly.
'I think we'll have a lot to talk about on the picnic tomorrow. Got to go, Matt. Looking forward to seeing you.'
I stared at the phone as if expecting him to say more, even though the line was now dead.
I replaced the receiver and went upstairs to my room.
Locking the door behind me, I undressed and got out the dildo, and licked it and kissed it as though it was a real cock, then I sucked it.
Lobbing myself up, I knelt down on all fours on the floor, then reaching behind me I pushed the head against my ring. It slid it right up inside me in one movement. The sudden shock of entry - even though I'd been expecting it - almost made my eyes pop, but I took a deep breath and leaned my ass back against the bed to keep it inside me.
I closed my eyes and drifted into my favourite land.
'Fuck me, Jack! Oh yeah, man...shove that cock right up me...YEAH! That's the way! Split my ass! You big cockplayer. Give me that cock! Whoaah! That's so GOOD!'
I pumped the dildo in and out while my other hand gripped and stroked my meat, rocking back and forth, fucking myself faster with the dildo and matching my speed as I jacked off.
With a choking gasp I splashed my seed wherever it wanted to go, darkening the bedroom carpet with my spunk, as I let go the dildo which slowly slewed its way out and onto the floor with a dull thud beneath me.
That night I slept a deep, satisfying sleep, after a full afternoon of sucking and fucking at the gym, and the prospect of more of the same with Jack.