Jack

Matt's picks up the story.

I've always liked looking at guys' bodies ever since I was at school, and I sort of drifted into gay activity in my last years at college. I'm not bad looking, if I 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, and prone to blushing.

As always.

I lost my folks when I was quite young, and was brought up by an old friend of Mom's - Alice - who loved me dearly, and did everything she could 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, 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 and he was just great to be near, and we'd fool around like two very close friends, or we'd go exploring in the woods after a picnic, and I found I'd always get a hard-on when I was close to him. I had no idea how old he was, though I knew he was some years older than me.

I'd never dared talk to him about my feelings for guys - I just assumed that as an adult he wouldn't understand. I was real fond of him and 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 at the thought of him. You know those erections that you know ain't gonna go away on their own. I never got a piss-boner when I was thinking of Jack - and 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 I collected. We'd play grab-ass, and he'd touch me in all those places where I loved to be touched, and he'd run his fingers up and down the crack of my ass, and then we'd stretch out on the white sand, feeling the cool breezes blow across our hard cocks. He'd kiss me full on my lips, and I'd run my hands over his tanned, muscled body as the surf rolled in over us, then I 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 own flesh. Then I'd come, 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 onto my chin.

Anyway, after college I'd got a job in an insurance company, which bored the fuck out of me, but it was a steady job, and occasionally, when I had to go out to meet a client - it was usually a guy - he'd hit on me, and despite my shyness we'd end up in bed together, rolling around on the marital bed while his wife was out.

All in all, it wasn't so bad but - as I said - I rarely made the first move.

The best place of all for me was the local movie theater because in the dark everything was anonymous. It was the place of horny dreams that really could come true

It was always quiet at the movies on a Monday evening, and I knew the manager, who always gave me a friendly wink as he let me in - I'd given him a blowjob when he'd called me into his office one day, but he wanted me to be his fuck-boy and I wasn't into that - and no matter how empty the place was, sooner or later a guy's hand would steal over my knee and down into my crotch and I'd get that, cockrising tingle as my erection stretched inside my slacks. Sometime I'd have a guy each side of me, and their hands would fumble over each other in order to get my cock out, and then I'd entertain them by jacking off both their cocks together.

I always took my time in situations like that because I was totally relaxed, and I'd slowly stroke them until they were clawing the air for me to bring them to a climax. Then, when I decided it was time, I'd give a little shiver and let myself cum, pumping my jizz onto the movie house carpet. Then I'd really work on them, enjoying hearing their gasps as their wads joined mine, and then we'd part; our transaction complete.

Sometimes I'd sit all through the performance on a seat in the theatre john, where the glory hole was, and wait until some guy stuck his piece through the wall. I sucked big black ones, slim, young ones and veined ones where the hair poked through the hole as well, and one afternoon I managed to suck off five guys, one after the other, before my mouth got to tasting cacky and stale.

I left a few guys waiting that day as I hurried out and headed for the door.

I'd 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 - I guess I'd have died of embarrassment if I'd got into a situation where I was supposed to take it 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 I'd bought the thing, I locked myself in my room, and laid out the dildo and lube on the bed, while I stripped off. There was something almost sinful about what I was doing 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 I spread the 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, as though it wasn't a dildo at all, but a real guy's cock - and I shivered slightly as the cold tip of the cock rested against my ring. I pushed, and it entered me, so I pushed a little more, and a little more, and then a sudden pressure built up in me that made me gasp out loud and my mouth opened wide of its own volition, but I didn't remove the cock. I left it for a second or two, where it was, until my ass became used to the invader, and then pushed again. My body filled - that was the only way to describe it, and I pressed myself further back into the bed, my legs wider still as I relentlessly slid the plastic head deeper and deeper into my ass. My hands were greasy now so I didn't want to lose it inside me, and I determined to keep a few inches of the cock outside my body.

At last, it was there, as far as I dared push it, and I lowered my legs flat onto the bed. The cock had a tendency to try to slide out of my asshole, but I rolled over onto my side, and kept it in me by holding my hand tightly over the end.

I pushed myself up into a sitting position with it rammed deep inside me, and I had a job at first to get my dick hard, but with some lube on it and my vivid imagination, I conjured up Jack, and this time it was his cock that was plowing me.

I gasped as I started to masturbate. I'd never felt this sort of invasion of my body, and it gave me a real charge. There was quite a lot of pain, though not all of it unpleasant, and I was determined to master the art of fucking my ass for future potential lovers.

My hand was now jerking much faster and then I realised that sweat was flying from my face and body after all my exertions, as I worked on my cock. My lips were pulled back as I bared my teeth in a snarl of lust and I snapped back my head 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 towels, in an almost endless stream, and I was then aware of my ass clenching, rhythmically on the dildo, in time to the pulsing of my cum.

Then I flopped back onto the bed and rolled over onto my side once more letting the cock slide slowly and lazily out into my hand, and I gently placed it on one of the towels.

I felt my ring.

It had been well stretched, but I knew it would regain its tight elasticity, and pucker up until next time I practiced.

I repeated this procedure for a week or so, enjoying the sensation more and more each time I fucked myself, and I longed for the time when I'd have a real man's cock in there instead.

Now I felt more confident, and 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 knew I'd strike it lucky at some stage, with the looks I got from some of the guys. The first session I went to was real quiet, and I ended up wandering around the place, and found there were only two other guys in there. They were in the rest room and were giving each other 69, so I figured it best not to interfere or join them, but it was on the fifth visit that I really struck gold.

I was in the showers after my workout, and a coupla guys came in - they were both a lot older than me, but real lookers, with those body-builder muscles, and heavily veined. The one nearest me winked at me as I soaped up, and I smiled back. "Hi, I'm Max," he said, holding out his hand. I shook it. "Matt." "Pleased to meet you, Matt," he waved to his companion. "This is Dave." I nodded to Dave. "Would you be..."he paused and looked around the shower room, then continued, "...interested in a little foolin' around?" "Depends 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 three guys could have a real cosy time," Max went on. "Get my drift?" "Lead on," I heard myself say.

We turned off our faucets, and Dave grabbed his towel and 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'd negotiated a few bends and stairs, then we descended into a dark room. I could hear that there were other people in the area, and realised that I was standing on a soft cushioning floor.

This was obviously the rumble room. A hand pulled me to the floor, and I felt a cock against my lips. I opened my mouth, and licked one huge head, already leaking and drooling. It tasted sweet, and it was followed by a slightly faster stream of pre-cum, then 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 now joined Max and Dave because a cock appeared either side of my head, and gently poked at my cheeks. I licked and sucked them all in turn, still very conscious of the activity occurring at my ass.

A cock was pushing at my sphincter ring, and a feeling of sweet relief swept over me as I realised I was at last going to be fucked by flesh and blood! I pushed my butt back and the cock slid in, deeper and deeper and I experienced once again that full feeling like when I'd first used my dildo. I relaxed, and took a deep breath - well, as much of one as I could with a mouth full of cock - and then let the cock flow all the way in 'til I felt the guy's bush at my ass. We were all moving now, and I sucked on each cock as it was presented to me, listening, fascinated, to the appreciative voices above me. "Oh baby, suck that cock...lick those balls, boy...oh yeah, man, this boy was born to suck...ahhhhh!"

One of them came quite quickly, and I munched on his cum, while the other one slid smoothly in to take his place.

I was real excited now.

This was a dream come true, and the guy fucking me was slamming at me, his balls slapping against my bum, then he heaved, and slapped my ass cheek, juddered, and shook against me, almost immediately I felt the hot sting as his cum shot into me. He kept the rhythm for as long as he could then withdrew, patting my butt, and leaving a cool place where he'd nestled his cock. Now someone replaced him new. This was a biggie, and I had to flex my ring real carefully around that love-muscle so he could ease into me, but he made it and he was soon riding me like a champion.

The air was thick with the smell of cum and sex and man-sweat, as more and more hands were stroking me. I lost count of the number of blowjobs I'd performed, and I'd given up wiping my chin, just letting the loads drool down onto the cushions.

Cleaning up wasn't my problem.

Again my ass was pumped full, and again he 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 leave.

Finally, the last load pumped into my mouth and the cock departed, and...nothing. I rolled over and lay down in a large lake of cum, my cock still hard, as no-one had bothered to take care of my needs. I slid my hands down and grasped myself, feeling the needful throb under my touch, and I thought back over the session. My mouth still had strands of cum sloshing around between my teeth, and my ass was leaking copiously onto the floor like a valve had been opened. I gritted my teeth and jerked my cock. The shiver grew, and took over my being, as I whacked faster, until I felt, rather than saw, my cum shoot from me, and spatter somewhere over there in the darkness.

This was definitely a session to remember!

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 once again.

Alice was out when I got back, 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 the envelope by the phone. It simply said 'Matt', so I tore it open and read the note.

'Dear Matt - I hope you had a good 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 on a picnic tomorrow if the weather is OK, Love, Alice. PS If you want to talk to him his phone number is....'

I re-read the note 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 fucking it had received today, and my cock rose at the thought of seeing Jack again. I picked up the phone and dialled the number Alice had left me.

Ring-ring-fucking-ring.

Come on Jack. Come on...

"Hello?"

That deep brown voice sent my cock stretching up the inside of my slacks.

"Hello?" the voice said again.

I gasped into the phone. "Jack?" I could hardly speak. This was the same sort of breathless pleasure I 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.

"Wh...what are doing back here?"

"I had a hankering after a home visit," Jack said. "Alice told me I could come and stay with you both while I'm here, and she's even invited me on one of her picnics. What d'you 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.

"Come on, Jack. What are you - 30 something?"

"35"

"So?"

"I bet you're a looker."

I blushed as he said it.

"Hey, I joined a 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 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. Gotta go, Matt. Look forward to seeing you."

Click.

I stared at the phone as if expecting him to say more, even though the line was now dead, so I replaced the phone in its cradle and went upstairs to my room.

Locking the door behind me, I undressed, and got out the dildo. I licked it and kissed it as though it was a real cock, and sucked it, then I lubed myself, and knelt on all fours on the floor with a bunch of tissues under me.

Reaching behind me, I pushed the head against my ring, and then 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, and I leant my ass back against the bed to keep the cock inside me.

I closed my eyes, and drifted into a favorite 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. Whoa - yeah that's so good...!"

I pumped the dildo in and out of my ass, while my other hand gripped and stroked my meat. I rocked 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 onto the tissues, turning them into a sodden mass of milky mulch, as I let go the dildo, which slowly slewed its way out of my ass and onto the floor with a dull thud behind 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.