Sorry this is so long. I actually edited it down some.
This is a true story that happened about 22 years ago, but I remember the details like it happened last week.
I was working for an agency and one day I was taking a briefing report to the Director's office. There was a cute petite blond who had been there only for a few weeks as a management analyst and who I had only become casually acquainted with. Her name was Mary and I had been told by the Directors secretary that Mary thought I was a good looking dude. I hadn't thought too much about it, but on this day when I was waiting to see the Director Mary saw me and said, 'hey can I show you something'? I said sure and she opened a desk drawer and picked out a small pamphlet, one of those that was printed on one sheet and then folded over into thirds. She came over to me and opened it up and it was showing instructions on how to put a condom onto an erect penis. The illustrations were drawings with coloring and were very graphic. It pointed out a number of things including how you need to be sure to leave the reservoir tip space for the ejaculate. She held it for me to look at for a moment then folded it back up and then used it to fan her flushed face. She said, 'this is very exciting', and just stood looking up at me. So I said, 'OK so are we talking about an unfulfilled fantasy here'? She just kept exchanging glances between me and the pamphlet. When she didn't say anything I jokingly said 'cause if you are I guess I could be your go to guy'. At the time I didn't think I was real serious and I didn't think she took me serious. She acted like she was at a loss for words so as I walked away I just said 'well that will give you something to think about anyway'.
So after lunch it was still on my mind about what if.... Well Mary came into my office to return the report to me and after some small talk she said 'well I have been thinking about what you said, and I want to know if you were serious or just funnin'. So now that gets the gears in my brain turning and after thinking for a minute I said, 'well, I guess I could be as serious as you would want to be'. So she thinks for a minute and said, 'where and when do you think that it could happen'? I said, 'well I have been working late and by 6:00 pm the whole building is pretty much empty. How about right here tomorrow after work and I have a condom at home I can bring'.
At this point this became one of those 'I can't believe this is really happening' conversations. Next she said 'well I happen to have a condom in my purse so how about today after work'. After some clumsy discussion I told her there could be no actual sex as I was married and I knew she was also. She agreed and as she left she smiled and said she was looking forward to it. I was asking myself 'what have I done'?
A couple of minutes after 6:00 o'clock my phone rings and she said that if I hadn't changed my mind she was on her way. Within one minute we were standing in front of my desk. She was visibly excited and nervous and so was I. 'well, should we do it', I said. She said, 'let's do it'. She is holding the condom packet in her hand. I told her to sit in the chair in front of my desk and I leaned my butt against the front of my desk, which put her less than two feet in front of me. Without hesitating I unbuckled my pants and my shirt and let my pants slide to the floor. That left a bulging pair of briefs directly in front of her, which definitely captured her stare. I told her the next move was hers, and without much hesitation she reached for the top sides of my shorts and began to slowly pull them down. As she pulled them down to the 'launch point' my rock hard erection sprang up in full glory and flexed up and down a couple of times. She said 'holy cow, this is gorgeous, you are amazing'. I said 'aw shucks ma'am', and she let out a nervous laugh which eased the tension a little. My heart was beating like crazy. She asked if she could touch it and I said please touch. I said 'you can't hurt it, honest'. She laughed again and the situation was becoming more comfortable. She began to very lightly trace her fingertips up and down the shaft and make little circles around the tip. She continues this play as if it was the first time she had been able to so intimately fondle a large erection. Maybe it was. What I knew was that about 30 seconds more of this and it was going to be all over. I unwrapped the condom and told her that she better do the plan or in a minute it was going to be too late. She said, 'are you that aroused', and I said yes. I took the condom out of the package and gave it to her. She carefully positioned it on the tip and slowly rolled it down perfectly, and then she just continued to admire it. Then I told that it couldn't end there and for the finale she should see it work to the end. She said, 'good, lets do it'. I told her to wrap her hand around the shaft and slowly work it up and down. She didn't need much coaching for this part. I wanted her to go slow in order to not let it end too soon. Then she asked me if I would do it for a minute so she could watch, which I did. At this point I thought about asking her to pull up her knee length black dress and show me her panties and/or some pussy pink, but I didn't. I later regretted not asking, but at the time I was thinking there might be another time. As she watched me jerking my cock not 10 inches away she said, 'this is just so exciting'. Again she took over, holding it just a few inches from her pretty face. I thought for a minute she was going to take it in her mouth, but she didn't. She was fascinated with the hair on my balls, and after gently fingering them for a few moments I reached the point of no return. I told her 'OK, squeeze a little tighter and jerk it a little faster and don't stop until I tell you to'. She did and we both watched the tip of my cock disappear in a slurry of pulsing cum. I was concentrating on continuing to stand without passing out. She just kept saying 'wow' over and over. She commented on how warm the cum felt. She looked up at me and said, 'this is the first time I have ever done anything even remotely like this and I can't tell you how exciting it was. And yes it definitely was an unfulfilled fantasy'. I told her the same for me and that I could honestly say it was the most exciting sexual experience of my life, which it was and maybe still is today.
In less than 30 minutes it was over. She offered to help me clean up and she did. I said by the way, how is it that you had a condom in your purse today? She told me that she usually carried one because it just helped her feel extra sexy. I walked her to her car and after a sweet kiss we went in different directions.
PS. There was one more similar event and I may write it down in the future.