I am a very horny guy and even when I am having regular sex I like to masturbate frequently. This is the story of one of my favourite memories-
I had been friend with Sheila for some time and we were very close. Before we actually met I had noticed her on campus and lusted after her. When we met in second year I was already dating so we became friends instead. I still thought she was incredibly sexy but never got up the nerve to make a move on her as I knew deep down she didn't feel the same way. Regardless we hung out, partied, went to films. She was one of my best friends.
As my best friend we often shared information about the people we were dating at any given time. We also shared fantasies. One time I revealed that I really wanted to masturbate for a woman and just have her watch. With my heart pounding I asked if she could do that for me- To my shock she agreed. She found the idea really hot.
So we moved from the living room up to her bedroom. She left me alone to go and get some candles (candle light is always sexy) and while she was gone I stripped naked and got under the covers of her futon. When she returned she didn't say much but she had put on a trench coat. She said that it made her feel like a dirty old man to wear it- She lit and placed the candles around the room.
By this time I was a bit nervous but had a raging hard on under the covers. Here was a good friend and I was about to be naked in front of her. She was fully clothed and I, except for the sheet, was very naked. I felt kind of vulnerable and it turned me on.
The futon was very low so she sat on the floor next to the bed and leaned against the wall. It was now or never. I pulled the covers down to reveal myself. I reached down with my left hand and began to stroke myself with long slow strokes. She murmured, 'You have a very beautiful cock'. I felt kind of cheap but really turned on.
With my other hand I alternated between playing with my balls, stroking my stomach and playing with my nipples- She found it fascinating that I like to touch other parts of my body. She asked if I like to have my cock slapped. I said no but I did like to have my ass touched.
She leaned in to get a better look at my hand stroking my cock. My hand was moving faster and my head was reeling. It was then that she reached forward and began to play with my ass. She slowly inched her finger into my anus sending waves of pleasure through my body. My body was twitching with each thrust of her digit. I wanted more and whispered for her to put in another finger. She quickly slipped another digit into my ass- it wasn't enough. Put in three I whispered.
She tried to insert a third but couldn't. To my amazement, she pulled her fingers out and popped them into her mouth, now lubed she had little difficulty sliding in three fingers. I felt good and full as she began to thrust her fingers deep into me. Occasionally she would pause to wiggle them around and then proceed again to thrust in and out of my ass.
My hands were a blur, my left hand rapidly stroking and the right tugging at my balls. I knew I was going to cum soon. The intensity of pleasure was mounting. I clamped my legs and ass check down on her hand as she madly pulsed on my prostate. When I came I cried out and shot a load of cum onto my chest and face (normally I just cum on my stomach). I lay there panting and reeling as waves of pleasure rippled around my body.
I realized my legs were still holding her between my cheeks and I let her hand loose. She slowly slid her fingers out and wandered off to the bathroom to clean up.
We spoke about this session once or twice later but never repeated the experience. I have recreated the scenario with my wife from time to time, as she like to watch me jerk off, but it just isn't the same when you are with someone who already knows you intimately. I often fantasize about asking a co-worker to watch me or meeting a stranger that would like to watch me- Maybe some day.
Sinister (the left hand)