...my hand couldn't stop, couldn't let go, wouldn't stop until again I'd felt his strong fat cock twitching in my hand, drenching my arm in cum again.....
My first year out of college I moved to the city and had my first job. I hardly knew anyone, and for the first time had my own apartment without roommates. So, naturally, I mostly went to work, came home and masturbated all evening.
The guy upstairs was a big, burly retired Navy man who worked in the city, and sometimes we'd meet at the bus stop and talk a little, and one night when we were both late coming home, he asked if I wanted to get a pizza. I said sure, and after changing clothes, I found myself eating pizza in his living room. I wondered a bit if he suspected that I jacked off all time. I'm pretty quiet when I jack off, so I didn't think much about whether he had heard me, but I forgot that sometimes I watched porn with the sound, well, unmistakable.
Chuck, about half-way through the pizza, said, 'So you like to watch porn, I've heard you at night!'
I must have turned very, very red. Gulped and said, 'Yeah.'
'So do I, want to watch some after we eat?'
I hadn't jacked with anyone since I was much younger. My pre-teen buddy had shown me how to masturbate, and we explored and discovered it together over many sleep-overs and after-school adventures until he moved away. I hadn't jacked with anyone since (almost). Now that I was masturbating a lot, I have to admit, I was thinking it would be hot to have a bud again.
Chuck was not my idea of a jacking bud...in fact the thought had never occurred to me. He was older, big and hairy. Not like my little friend at all. Not my fantasy of a bud, no way.
Jack asked again, 'So, do you want to watch porn and jack off?'
'Yes.' Right away my heart started pounding.
For a minute, I couldn't speak, then Chuck started asking me more questions, and my answers came out, straight and full...
Before we left the kitchen, Chuck knew that I jacked almost every night (he did too), that I liked female masturbation videos, that I'd jacked with my friend, a lot, when I was young, that I sometimes wear a bra and panties when I play with myself (I'd never told ANYONE), that I liked to jo in the bushes at the beach, that I like to jack off slowly, that I let a guy I met in Europe suck me once, and that I masturbated with my friend's wife when he wasn't home, jacked off looking at our neighbor when I was in junior high, and came in my pants in English class in high school about ten times, and that I'd never touched another guys cock since grammar school, and that I'd shared a studio bedroom with my dad when I masturbated every night under the covers, and heard him do the same sometimes...
We went into the living room. Chuck left me and went to his bedroom, and came back naked. Seeing him shocked me. I hadn't seen a real man's cock up close and hard like that. He was very hairy, with thick black curly hair, but his balls and cock were so big they stood out from his hair, and were reddish brown. He was muscular, with big thick thighs and meaty hands. His cock wasn't that long, seven inches, but it was thicker than I'd ever imagined a cock before. He was already hard. He knew I was looking. I was hard too.
As soon as we pushed away from the table and walked to the living room, I felt swelling in my pants, but hadn't stripped. A little embarrassed, or scared, I waited to see what he would do. He went to the TV and started a vid, and while his back was turned I stripped totally naked, my cock stiff and bouncing.
Chuck gave me the couch which was VERY comfortable, and he told me to take my time stroking and be comfortable. The video was awesome, of one woman's orgasm after another. I was soooo stiff and hard, and pretty soon I was ready to cum, holding back, my legs writhing a little. Chuck stood up and stood in front of me, starting at my cock in my hands, his fat, hairy pudgy slug of a penis right at eye level....
...I got nervous, and for a minute began to go limp.
'Watch my cock,' Jack said.
My eyes became riveted on his cock. It was wet with precum. Hard and veiny. I could smell him. A huge swell passed through me, and my ass clenched, my cock got twice as hard as ever before in my hand.
I was pounding hard now, hard and fast and tense, and so was Chuck, his fat cock was red and swollen, pounding next to my face. My face was burning. I wanted to jack and jack until Chuck's cock started spurting....
....and suddenly an uncontrollable, hard, hard orgasm crept over me and my cock spurted ropes of cum into the air, and in a moment gobs of cum from Chuck's fat balls shot from between his large, pink slit and splattered on my naked skin, my face and in my hair, I was so into watching him cum it was minutes later I felt the cum sliding and dripping around my body.
Chuck brought a soft towel for me to clean up, and we sat and relaxed and made some jokes, and talked some more. Soon I was admitting to him my fantasies about cocks, imagining them cumming, and telling him the thrill I felt being watched by my friend's ex while I stroked myself. And I was telling him his big fat cock made me really hot. It all just kind of blurted out, the truth like that......I wanted to do more, but fear and embarrassment overcame me, and quickly I left....
The next night, I was at his door, and he answered naked and hard. He'd been jacking since he got home. His fleshy cock stood out from his black hairy loins, and I rubbed it once. I came in and stripped off my clothes, but I was a little nervous and we sat and talked for a long time, stroking a little, but not intense, and I knew I wanted something but I didn't know what, so we kept talking and my gaze was fixed on his hand rubbing his cock, his fleshy fingers slipping up and down that fat ugly thing, so different from my little buddies hairless, thin stiff little dick, so huge and masculine and hard, fleshy fingers rubbing, caressing, squeezing....
'Do you want to stroke it?'
I don't know if I even spoke a reply, I only remember the next thing his cock was in my hand, and I was jacking him off, slowly with long strokes, feeling it in my hand, letting it swell in my palm, trying to do a good job, then faster and harder, as he told me 'yes, yes, like that' whenever my stroke sent shivers through his body. It felt so awesome, so good, and without touching myself I was stiff and bouncing in the air and every jerk of my arm made me harder still between my legs.
Chuck began to moan and I realized for the first time I was going to make him cum, make him cum hard, and my hand took over, stroking him perfectly, and his hips began thrusting with my hand, my hand squeezing his cock with every thrust, wet and dripping now my other hand wrapped under his thigh and around his balls feeling him grind his butt against my wrist....and then he tensed hard and long, exploding cum, wetting me again with cum, releasing, relaxing, going limp, and in a moment he pushed me to the floor with his foot, knelt down next to me, and stroked me until I relaxed in his hand and then jerked and writhed and waves of release poured over me.
I lay there tired and spent, but my hand slipped between his legs and found his cock and squeezed it and rubbed it and slid over his balls and around his thighs and pressed his swelling against his belly and felt it rise again and twitch when my thumb tweaked his slit, and my hand couldn't stop, couldn't let go, wouldn't stop until again I'd felt his strong fat cock twitching in my hand, drenching my arm in cum again.....
Well, that was the first two nights of many spent masturbating with Chuck, cumming in each other's hands, watching porn, hot and stiff and stroking until one of us couldn't keep from spreading legs wide to finish our self pleasure, and I learned the pleasures of stroking cock all over again.