My wife (who was my girlfriend at the time) provided me with the best jack off session I've ever had. Read on if you want to hear more!
The best masturbation experience I ever had did not come from my hands, but by the hands of my wife (who was actually my girlfriend at the time). By the way, this experience is NOT the reason she became my wife, but it was an added bonus that she was able to masturbate me to huge orgasms!
The best masturbation experience I had occurred one morning when we were taking a shower together. We were just into the 'heavy' dating period. You know the 'heavy dating' period, it's the time when you make moon eyes at each other, become excited to just talk to one another on the phone, and enjoy incredible, hot sexual encounters. As we were I in the shower I was soaping her down, and she was soaping me. I loved to caress her long thin legs, her tight waist, her heart-shaped ass and her big, beautiful breasts. She was unfamiliar with shaving her cunt, something I had already introduced her to, so rubbing my hands and fingers up and down her hot, slick slit in the warm shower was a stimulating experience for both of us.
After playing with her body in the steamy shower for a while, she said, 'OK stud, get ready for the hand job of your life.' Shocked, and pleasantly surprised, I leaned back against the shower as she reached for my stiff cock and tight balls. She cupped my balls with her right hand, and while facing me and staring me in the eyes began stroking my quickly hardening shaft with her left hand.. The warm water splashing on my body, her hands stroking my cock and balls, and her wicked grin and sexy eyes staring at me made me feel both relaxed, and at the same time, extremely horny. I closed my eyes as she brought her mouth to my nipples and kissed first one, then the other, than back again. No woman had ever licked and nibbled my nipples before, and although it was a strange feeling at first, I soon discovered that it provided me a whole new sense of stimulation that I began enjoying. Her right hand, which had been massaging my balls, snuck lower down and I felt her finger begin caressing my sphincter. Again, very few other girlfriends had ever played with me down there before, and once again I was awash in a strange mixture of new feelings that I soon began to enjoy. Her left hand all the while continued to jack me, slowly rising up to my hard purple head, then back down to the base of my shaft. Up, then down, back up, then down, her hand was just the right tightness, hard enough to pull the skin on my cock head but not so tight as to cause me discomfort. Her hand made a slapping noise each time she brought it quickly down to the root of my cock. Other than the water running and my heavy breathing, the only sound in the shower was the soft 'slap, slap, slap' of her hand hitting my shaft base.
'Lie down,' she said softly, yet firmly. I was a bit surprised by her control, but didn't need to be told twice, and I laid my back down in the shower, my legs spread up in the air between her body. The water hit my stomach as she grabbed a bottle of baby oil and throughly rubbed it into my cock. Then, she oiled her right and said, 'lift your ass up more.' I did as she commanded, and lifted my ass up in the air, using the back wall of the shower to balance my now fully spread legs. Seldom had a girlfriend taken such soft, yet strong control of me, and I found myself relaxing and enjoying her manipulations of me even more. She sat so she was facing my cock and balls, and leaned forward for a moment to rub her big tits against my cock. She buried my shaft between her tits, while slowly dripping oil down in between her cleavage. My cock slid easily up and down the tit-tunnel she made for us, and the feelings this caused both of us were of great pleasure. At this point my breathing was very heavy, and noticing that I was getting ready to cum she stopped for a minute. 'Relax,' she said, with a smile. I closed my eyes and felt the hot water spraying my stomach. Her hands began working my ass, rubbing more oil all over my exposed cheeks and onto my anus and balls and cock. She started again with her hand on my rod, again tightly holding it while pulling up, then pushing down. I was lost in a haze of hot, sexy stimulation when I felt her fingers again playing with my ass-hole. I opened my eyes quickly when her finger pushed against my hole, no woman had ever stuck a finger up my ass before (although I had done this from time to time when masturbating alone). 'Enjoy it,' she said as she circled my sphincter with her slipper finger. I could feel the oil enter my ass as she gently squeezed the tube against my hole, squirting oil into my anus and lubing me for what was to come. Then her finger went back to circling my hole and slightly parting it. 'Open yourself to me,' she said, and I found myself relaxing my hole and gently pushing my sphincter toward her now insistent finger. Meanwhile her other hand continued to stroke my now raging boner. As her finger slid into my hole I suddenly felt the overwhelming satisfaction of having my ass filled, and was about to cum again. Sensing this she withdrew her finger quickly and stopped her pumping of my now twitching cock. We both breathed in the steam, and enjoyed the sexual excitement she was providing us. She played with her nipples, and stroked her cunt lips and clit for a minute, then said 'let's get it on baby!' and once again circled my cock with her hand. Her finger quickly and easily penetrated my ass this time, and her pumping hand and finger in my anus once again brought me near to climax.
Three times she brought me right to the edge, and three times she had me cool down while she played with herself. Finally, she asked with a wicked little grin, 'Are you ready to explode?' I gasped 'Yes!' and her hand again went to my now fully swollen cock . More oil was deposited on my cock and ass, and again she rubbed my ass cheeks with her hand, bringing me a heightened sensitivity to my butt and anus. I positioned my feet higher on the wall, spreading my ass cheeks farther apart and granting her full access to my now willing anus. She surprised me by slapping my ass cheek with her hand, and I opened my eyes to see her broad smile as she slapped my willing cheeks. 'Do you like being spanked?' she asked with a gleam in her eye. 'Oh Yess,' I hissed between clenched teeth. She spanked me, sometimes with soft, gentle caressing strokes, sometimes with quick, hard slaps. The sharp 'Slap! Slap! Slap!' echoed off the walls as she spanked my quickly reddening ass cheeks. The pain/pleasure when right to my cock, and once again I had to be calmed down, almost going over the peak and into orgasm.
After another calming, her hand again began stroking my now fully engorged and sensitive cock. Her finger easily penetrated my now willing anus, and she began finger-fucking my well used ass. Her hand began piston-ing faster and faster on my cock. 'Tell me when you're almost ready to shoot' she commanded. I was lost in a red haze of incredible sexual stimulation, my body enveloped in my horniness like a blanket, her hand on my cock giving me pleasure I had never felt before, and her finger fucking my ass with a passion I had not enjoyed before. My balls tightened and the old familiar feeling of my red hot sperm collecting in the tightening base of my cock told me it was time to shoot. 'I'm going to CUM!' I gasped. 'Yes baby, cum on me now, cum for me baby!' she said, and as she began tickling the inside upper part of my anus. I found out later this was my prostate that she was tickling, but all I knew then was the feeling she gave me stroking me up there with her finger was an incredibly stimulating feeling I had never had before. While still pumping my super hard cock, I was bowled over with the most intense feeling of pre-orgasm I had ever had. 'Ohhh, YESS, I'm CUMMING' I shouted as my orgasm literally exploded out from my now pumping ass. My orgasm started strongly in m now tightened balls, and then traveled up my engorged cock and spread to envelope my entire body, from my hair down to my tightly curled toes I was a ball of pure orgasmic energy. 'NNNGGGH, NGGHHHH, NGGHHH! UNNNHHHHHHGGG' I grunted as my body was gripped with each thrust of my powerful orgasm. My hips thrust uncontrollably as my body was washed in waves of red hot passion such as I had never felt before. I shot huge loads of sperm high into the shower, and as my energy drained I opend my eyes and saw stars and felt very much like I was going to pass out. She continued to stroke my still twitching cock, and the pain this brought made me cringe. She stopped stroking, and gently pulled her finger out of my butt. I dropped my legs to the floor and breathed in and out deeply and slowly, feeling a warmth and satisfaction enveloping my body like no orgasm had ever done before. She knelt over me and kissed me long and deeply, and I felt a closeness to her like I had never felt before. Our bodies, slipper from oil, hot water, and sexual sweat became one in the shower, and she laid on top of me for what seemed like an eternity, as I held her close to me. It was the most incredible jack off experience of my life, and to this day still is!