My own personal, best sexual experience occurred some ten years ago and quite by accident. I was visiting my step-mother's house to gather some whitewater boating gear for a trip I was taking the next day. I am married at this time, but my wife was unable to be there due to her work. Suddenly, an unfamiliar female voice greets me in a friendly manner and the person speaking comes up to greet me with a hug. It turns out that this fairly forward woman, named Sarah, is my step-mothers' new room-mate.
As we discussed my up-coming canoe trip, Sarah announces that she is an experienced boater and since she was off work for a few days, would I take her with me on this trip? I jokingly said 'sure', as long as my wife did not mind,(thinking, once Sarah knew I was married, she would change her mind).
Anyway, Sarah persisted, and my wife approved, so we are off that night for a seven hour drive to the river that I was to float. Sarah was about my age, maybe even a little older...a redhead with pale complexion and very obvious breasts on what was otherwise a 'normal' physique for a woman of her height(5'6').
As we drove through the night, our conversations often turned to sex. It turns out our Sarah was a therapist of some sort and from time to time had to be with male patients when they were nude(such as giving them whirpool baths).
Sarah said she really enjoyed that part of her work, as almost every male patient would get a hard-on, because of being nude in the presence of a woman therapist. She said the best part was to 'relieve ' them of their 'problem' by jerking them off.
Her conversation was really turning me on, especially when she remarked that she almost came herself when she saw a man ejaculate. She quite openly talked about sex with her boyfriend, who was under strict orders to 'pull out', not for birth control, but for Sarah to witness his cum-shot. I was becoming desperate to show her my own cum-shot, as I was now rock-hard and straining against my sweatpants.
Unlike many of the well-hung contributors to these pages, I am fairly normal in size, except that my cock gains a great deal in diameter when fully hard. Also, the head really swells and even pulses with my heartbeat. As its resting size is considerably smaller, when I get hard in sweatpants, it really shows!
By now, I was determined that something had to give, when I see a large rest area ahead, one that I had stopped at before. This was a rustic, stream-side rest area, with picnic tables, grills, and many separate spaces with trees between. I suggested that we get out and stretch, due to the long drive.
Sarah then leans over a picnic table and asks me to rub her back. As I began to deeply massage her back, she pushes back with her butt against my already swollen and sensitive cock. I deliberately allowed my cock to slide between the cheeks of her butt (she also was wearing thin sweatpants) so that she would have no doubt about the effect she was having on me. We continued like this for a short while (I really believe I could have cum in a few more seconds ), when she suddenly stopped grinding against me. She reminded me that I was married and that I should be a 'good' boy.
With that she laid down, belly-first, on the picnic table to rest. I decided to stand in front of her and continue the massage by rubbing her shoulders. Sarah then opens her eyes and is staring straight at my swollen crotch. Without saying a word she reached out and started squeezing my cock with a skill and passion that I had never felt before. She then pulled down my pants and just stared at my erection. My cock was leaking pre-cum, pointing towards her face and the sky, as she began to deftly stroke it.
'You need to cum right now !!!', she declared. She stood up and began furiously beating me off. I could feel the cum building up to shoot, when she abruptly stopped and said, 'Now you have to finish just for me'. She knelt down in front of my cock, while I masturbated desperately. I knew now that no matter what, I was going to cum.
The first spurt was a long, white rope that hit Sarah's face and pretty red hair. Again and again, my nuts contracted as I pumped spurt after spurt of cum on Sarah's face. I felt like a porn star who just gave his best ever money-shot. When the cum-shooting spectacle finally ended, Sarah reached into her pants and fingered herself until she also had an explosive(and very wet)orgasm.
Afterwards, she told me that I had given her the thrill of her life, that my intense ejaculation was the best she had ever seen. We never had intercourse during this 3 day canoe trip, but masturbated ourselves and each other constantly .
Later, when I would visit my step-mothers' house, Sarah would find an excuse to be alone with me so she could jack me off. I am quite sure that she made me cum a few hundred times while she was my step-mothers room-mate. To this day I fondly appreciate her skill and her love of the visual aspect of ejaculation.