Just after I finished college, I was living in a ground level studio 
apartment. The sofabed was about 6 feet from the sliding glass door 
with a draw blind that was your only seperation from the outside 
world. If the curtain was open, anyone walking by could see right in 
and see the bed. I had only been there about 3 weeks, when I had to 
go to the rental office for some reason (don't remember exactly what 
it was). 

It was summer in New Jersey, and I was wearing a pair of loose 
fitting shorts that were not very long in the leg, but long enough 
(just barely) to hide my cock. It was swinging around inside the 
shorts as I walked to the office, and the rubbing of the light 
material against it was starting to get me excited. By the time I 
reached the office, I had a semi-hardon. When I entered the office, 
I saw a very sexy woman behind the desk. She looked up when I walked 
in and her eyes went directly to my crotch. I knew she was looking 
at my cock, which made me get even bigger and longer. I told her 
what I was there for, and as she listened, she leaned back in her 
chair and crossed her legs. When she did, I could see her stocking 
tops and garter straps. This got me even MORE excited until my cock 
was sticking out of the bottom of my shorts. She was staring at it 
and then looked up at me and licked her lips. 

I moved so that more of my cock was sticking out (about 5 inches) and there was more still in my shorts. I though I was going to shoot all over the desk, because here was this sexy, older woman, flashing her stocking tops at me and staring at my cock. She said something about finding out for me whatever it was that I had asked about, and she would let me know. I told her which apartment I was in and left, my cock making a huge tent in my shorts. 

I went back to my apartment and immediately started jacking off, thinking about her. I was just getting into it, when I saw her walking toward my place. I slowed down the pace as she came to the door and that is when she saw what I was doing. She came right in and told me that I shouldn't have to be doing that, and I told her that most of the women my age were afraid of it once they saw how big it was. She said those girls were fools, and she would show me how an older woman would "handle" the situation. She sat on the edge of the bed and took my cock in both hands and slowly started stroking and squeezing it. She slowly moved her hands from the base all the way to the head using a twisting motion, and then back down again. 

She sat so I could see her stockings and said that she had seen me staring at them in the office. She said she was pleasently surprised when she saw my big cock start coming out of my shorts. AS she stroked me, she promised that she would come back again soon and show me how well it fit in a "woman's" pussy ( I didn't tell her that I knew very well how well it fit, but that story about girls my age worked everytime)! She was telling me what a big cock I had and how she had never seen one that big, and going on and on. I was getting ready to shoot, and when I did, it ran down all over her hands. She got up and went into the bathroom and washed her hands, then walked out. I DID see her again, two days later, and she kept her promise.