My first real jackoff was when I was 11 or 12 (now 55). It was with a friend my age who had moved away for a couple of years and then moved back to just a few blocks from our house. His name was Craig also.
His mom called my mom and set it up for me to spend the weekend at their house and for Craig and I to renew our friendship.
Man, was it ever different from the last time we had seen each other and were still playing with army men!
Not long after my mom dropped me off I sat down for dinner with his family. As soon as it was over Craig got up and motioned me upstairs to his room. His room was up a short stair from the second floor where the other bedrooms were. It had been a narrow, high pitched attic that had been converted very neatly. It was small even for two sixth graders, but cozy and apart from the other bedrooms. It only had one bed, a small twin size.
Once inside he closed the door and instantly said. 'Let's beat off'. I naturally followed his lead and said, 'OK', even though I wasn't sure what he meant. I did know it had to do with playing with our penises, though.
He actually pulled my pants down and made me lie on the bed so he could pull my shoes, socks, jeans and even my underwear off. He was very urgent about it all and I didn't feel alarmed or shy...it was actually very exciting. My penis was rigid as it could be by the time he stripped my briefs down and off.
He then stripped completely nude in seconds. I was shocked at the whole tableau of his groin. He was well ahead of me in puberty. He had a small soft brush of hair (I was hairless) on his pubic bone just above the base of his very large penis...actually, it was a long and thick cock that a grown man would be proud of. It's hard for me to gauge its measurements...when you're a young boy of 11 or 12 lots of things look bigger than they do when you're older. But, I think it must have been 6 to 7 inches at full erection and, as I soon found out, my hand couldn't close around it. It was very thick and the same thickness for it's full length including the head. It was beautiful to me and I had a serious case of butterflies in my stomach.
He jumped into bed and my eyes didn't leave his cock. When it was fully erect and he was standing up it would jut out and down at an angle from him because of the heaviness of it. Mine, in contrast, would point up and out at angle. His balls were much larger than mine, like two eggs. Mine were smaller and left a lot of room in my scrotum.
He got to it right away. I turned on my side to face him and he lay on his back. He closed his eyes and wrapped his fist around his cock and started pumping it rapidly. I reached down to mine and began to do the same thing and it felt okay, but apparently wasn't making me feel the way he was feeling. His hand was a blur and it made a slapping noise and his balls would bob up and down.
After two or three minutes he abruptly (that word describes a lot about Craig) stopped and turned to me, leaning on an elbow. He reached over and with his right hand (same hand he was jacking with) cupped my balls and cock. It was an utterly delicious sensation that makes me hard right now typing about the memory. His hand was so warm and padded with flesh and he knew precisely how to press it gently but firmly against my cock and balls and move it in short strokes that awakened feelings and desires in me that made the room spin.
With my right hand (closest to him) I reached over and touched his thick cock. He had this characteristic sound he'd make, an ooooooo followed by a slurping inhale between his teeth and pursed lips. Abruptly, he let go of me and layed on his back. Now I leaned on my right elbow and side and actually pressed my penis and legs and tummy against the side of his muscular body. I put my left hand on his cock and gripped it firmly but softly around the middle of the shaft. Now there must have been two inches in between my thumb and fingertips and I was concerned that my hand was too small. I asked him since he was so thick if he wanted me to use both of my hands but he hissed, 'no your hand feels great, just move it up closer to the head' and he put his hand over mine and moved it to where he wanted it.
His hand over mine on his big cock sent a thrill through me that started underneath my testicles and made me shudder violently. He asked me, 'what's wrong?' I said, 'nothing! I just had the most wonderful feeling and it gave me a big shiver!' He said, 'that means you're ready for this...tonight's your night...I'll do you after you do me.'
I was happier than I'd ever been in my life. Thrilled, with butterflies and my throat was dry and my voice was husky and hoarse. My diamond hard penis was actually beginning to hurt, I thin it was about 4 inches long erect and maybe 3' or around. It's funny, I didn't feel inferior at all. I just enjoyed getting into his cock and he certainly seemed into mine. He reached his left hand down and cupped my genitals again and pressed down with pulses at the place between my anus and the root of my penis. When he'd press my cock would involuntarily respond with a flex and intense pressure in the blood engorged head which had swollen bigger than ever before...it was almost purple and very shiny.
His hand over my hand on his cock moved exactly how he wanted it and I could feel it throb and expand...he was cut as well as I and the head of his cock was gorgeous to me. It was also plum colored and shiny and a bubble of crystal clear fluid was now visible on the urethra opening. He removed his hand from mine and gripped the bedcovers at his side, his left released me and did the same. His breathing was rapid, shallow and ragged. His hips started to tilt and thrust a little upward and I could see his stomach trembling. I kept jacking him like he showed me and increased the speed gradually up to the speed I thought he wanted and he made those 'ooooooo' and slight slurping sounds.
His coming was abrupt and without warning. His head and shoulders bowed upwards and he stared at my cock on his hand and made a long grunting sound and came. It was amazing, I could feel the semen shoot up his urethra under my palm and he shot streams of milky white semen and sperm up about a foot in the air that then landed on his face and chest. I think he had 4 or 5 spasms of orgasm and reached for my hand to slow it down real slow. Cum had steamed out of his cock and down over my fingers and onto his abdomen. After a few seconds of slowly and lovingly stroking his cock I let go.
I held my hand up to my face and looked closely at his cum and marveled at it. I stuck my tongue out and tasted it and it tasted like nothing I'd ever tasted. It sort of reminded me of fresh laundry. At least that's the impression that remains with me. He reached over and wiped it off my hand with a towel, he hadn't seen me taste it and I didn't mention that I had.
His body was flushed and he was sweating. He reached over to the window sill and turned on a little oscillating fan which felt great to me as well. At that point I sat up and peeled off my tshirt so I can be nude just like my friend who was the greatest guy in the world to me.
I asked him if I did it the way he wanted and he laughed and leaned over me with his eyes about 4 inches from mine and said I was the best ever and flopped back on his back enjoying the afterglow. I was filled with a thrill of confidence and so proud that I was his 'best ever.' It meant so much to me, even now as an middle aged man I don't know why, but it still makes me proud and turns me on.
We didn't talk for several minutes which was just fine with me. I stared at the ceiling and squeezed my swollen penis and waited as my stomach had waves of ripples of desire.
Abruptly, Craig rolled over almost on top of me, his heavy and still massive though flaccid cock flopped heavily onto my thigh right at the top and just an inch from my cock. His stomach and chest were pressing against me and his head was inches from my face, turned to gaze at my body. His right hand was very gently stroking my chest, stomach and circled around my genitals and down to the tops of my thighs and then back up to my chest again. When his fingers and palm brushed my lower abdomen and inner things my pelvis bucked uncontrollably. I sucked in breaths and held them and when I let them out I was kind of embarrassed by my moans which sounded so childish compared to his sounds.
He leaned his face in close to mine and looked in my eyes and whispered, 'I'm going to make you a man, just like I was made a man.' Of course I craved this more than anything else in the world and waited.
It surprised me when he put his mouth on my nipple and kissed and licked it. But it was wonderful! I felt an electric like jolt that seemed like it went straight down through the middle of my body to the base of my penis. He then abruptly moved straight to my penis and moved my hand away. He gripped it in his fist and it felt so much better than my hand. It was so warm, thickly padded with flesh and strong but incredibly gentle and delicate. I long husky moan came out of me then... more like how he sounded.
He then slid his fist up over my head and began to stroke me just like I had stroked him. He abruptly began to stroke me rapidly and began grinding his once again fully erect cock against that soft and sensitive area on the top of my thigh just an inch or two from my his pumping fist.
I came almost instantly. I was out of control completely and my pelvis bucked in spasmodic thrusts and what I would call sobs seemed to come out of my throat. Wave after wave of a real orgasm wafted over me and then I slumped back into the mattress as his hand slowed to a stop. He moved his hand down so that it wouldn't irritate my overly sensitive corona and glans and he would just gently squeeze it from time to time.
He held his hand up for me to see the dribble of milky semen and sperm that I had ejaculated. He licked it and held it over to me and asked if I wanted to see what cum tasted like (heh heh) I said yes and licked it all off of his thumb and the backs of his fingers....it tasted just like his.