Jacking Ray

This was my fourth visit to Ray's apartment off-campus. I was determined to ask him to masturbate with me. Every week a few of us guys would get together for pizza at a local place. Ray was the alpha-male macho of our group—he lived off campus and, according to him, had a line of girlfriends outside his door just waiting to enjoy his oversized cock. It was mostly true, and he was the envy of all of us who were struggling just to get a date.

I went over to his place twice, just hanging out and talking, kind of nervously, about sex. I hadn't admitted it to myself, but the reason I was there was that I really wanted was to jack off with him. I was kind of dumb until finally he told me so, "Hey, you really want to jack off with me, don't you?" I just laughed and tried to be cool, but when I went back to the dorm that night, it hit me hard that I really, really wanted to do just that!

Lying in bed that night I remembered that a couple of weeks before, at the pizza place, he'd let drop that he had jacked off with guys in high school. Our eyes met for a moment, in recognition and desire, and the next night I "just happened" to drop over to his place. A few days later I went over again, nervously talking and steering the conversation toward sex. That's when he said that, and now, while my roommate snored in his bed, I jacked off thinking stroking with Ray.

The next afternoon I was over to his place again, ready to admit to him he was right, and ask him to jack with me. When I got there, who should also be there but a girl from my history class that I had a crush on! They were flirting pretty heavily, making lots of sexual jokes and my mind went racing out of control—were they fucking? Were they going to that afternoon? Had they done it before? How much? I left after half an hour, and since my roommate was home, I went to the toilet and jacked off.

I was obsessed. The next day, I and asked Ray if I could come over and he laughed and said, "Sure. Sharon's got class this afternoon." And so there I was, sitting on his couch, and he was telling me about sucking on Sharon's gigantic nipples the day before, and about how, though she seemed shy and bookish, she'd been fucking guys pretty regularly since she was fourteen. He told how she sucked his cock before taking it doggy-style. I felt my cock get hard in my pants, and was sure the Ray saw it, and I was hot and blushing and just blurted out, "Hey, do you wanna jack off together."

"Sure," he said, "why not? Take off your pants and let me see your cock." I stood up and unbuckled my pants and slid them off, and, not looking at Ray, folded them and put them on the sofa. I felt my cock totally stiff and bouncing, and my cheeks hot.

"Come over here, let me see it." That stunned me. I'd imagined, in my mind, that I would sit on the couch and Ray would be in his chair, and we would stroke our cocks watching each other. I never thought of standing naked for him to see me, much less touch me, but now I was walking the three steps to his chair to present my cock. His hand reached out and cupped my balls, while the other hand slid around my shaft and stroked gently. "Very nice," he said.

After playing with me for a little while, he stood up and stripped and asked if I wanted to stroke him. His body was pale and firm and muscled, and his cock was as big as he'd bragged, a thick eight inches, very straight and getting hard as he gave it a few strokes. I stood in front of him, my heart beating wildly. He grabbed my hand and put it on his cock. "Feel it," he said. I held it, and a jolt of excitement almost knocked me off my feet. It felt SO GOOD to hold it.

"Man, that feels good—keep going!" he said, and I began to stroke him, first with one hand, and then with both. He was hard now, his hands on my shoulders as we stood there, looking down at his cock in my hands. I loved the touch, and desparately wanted to please him and make him cum. "Dude, that's awesome!" he said, and shifted his weight onto both feet. I stroked him harder and faster, clenching his balls, his large, hairy balls, in my hand. I had never held a guy like that before, but I knew just what to do, and I felt Ray coming closer and closer to cumming. I felt him clench my shoulders hard and his whole body tense. I stroked furiously and finally his cock spurt gobs of cum all over my arms and hands and belly. He was grunting, loudly. I held onto his cock tightly. For a moment, his cock belonged to me alone.

Ray collapsed on the sofa, smiling. "Awesome! You can stroke me any time, dude." He looked at my hard cock. His hand was gently playing with his own, now limp but still swollen. "Stroke it for me," he told me. "Come over so I can watch up close." I stood in front of him, my cock level with his eyes, and stroked. Damn it felt so good! In a few seconds, I was ready to cum and began to moan. Just as I began to squirt, he held up his hand to catch my cum and keep it from landing on him. I shot into his palm. Oh, god it was a great cum!

After I stopped twitching, Ray held up his hand. Cum was dripping out of it. "Hey, you wanna eat this?" I leaned over and licked up my cum from his hand. Wow. I never ate my cum, but man, that was awesome!

Then Ray said he had studying to do, and I was out the door.

The next night was our pizza night, and Ray was especially macho and bragging about his girlfriends. We stayed late, and others left, until it was just me and Ray and another friend of Ray, Larry, at the table. I was in the middle of saying something when Ray suddenly broke in, "Hey, Larry, this dude gives an awesome hand-job!" I was totally, totally embarassed! And then deleriously HOT.

All night I'd been thinking of holding Ray's cock again, and then he invited me—and Larry—back to his place., telling Larry what a good cum I was going to give him. Well, I don't mind telling you that I did! We were all naked, and my hand caressed Larry's thighs and butt. He had a handsome, compact cock with tight balls and a big helmet. He exploded in my hand. Ray was watching and stroking himself and was almost ready to cum, too. He told me to come over, and I smeared Larry's cum on his shaft before he, too, exploded.

Larry stroked me a little while I was jacking Ray, but I was too intent on making Ray cum to get off myself. Ray told me to jack off in front of them, and this time to collect my cum in my own hand and eat it. They both watched my legs buckle as I came. It was SO HOT!!!

Needless to say, I jacked off Ray, and Larry, many times after that, whenever Ray called, really. But there was one more thing. Ray told Sharon that I had jacked him off, and that I loved masturbating. How did I find out? Because Sharon told me one day after class! I was embarassed, but she mostly just wanted to talk about Ray's cock and what a good fuck he was. Over coffee, I confessed that Ray had told me about her awesome nipples, and that since then I had a fantasy of sucking them while she masturbated. She said she was getting REALLY hot, and invited me back to her place.

We rushed passed her roommate in the living room directly to her bed, where she pulled off her sweater and bra and then slid off her panties. "You can suck them!" she said, and we lay on the bed, both stroking ourselves, while I sucked on her nipples. She had a short, hard cum, and a moment later I came too. Without being told, I licked my cum from my hand.... Well, every Tuesday and Thursday after class, Sharon and I went to her place. She was fucking Ray regularly, and we never fucked, but we loved masturbating while she told me about Ray's cock, which I knew so well, banging hard into her pussy.....