Milwaukee Cuckold and the Cleaning Lady - Sex Stories

Milwaukee Cuckold and the Cleaning Lady

I still say I am one of the luckiest guys in the world. We have been married over 30 years and Judy my wife still has sex 3-4 times a week, with others. I am a cuckold and live vicariously through what my wife does. Judy has a few regulars that she meets with while I am at work. One of these “friends” is actually an old friend of the f****y. Judy meets with him two times a week. He knows about our situation and the fact Judy fills me in on what they do. Often times Judy will call while she is entertaining and leave me a message on my phone at the office. Once in a while I am lucky enough to take it live. Well one Wednesday morning I had a light day at the office and I was sitting in my private office talking to one of my assistants when my private line rang. I answered it and Judy was on the line begging for more and moaning with whomever she was with. I kept saying things as though as I was talking since my assistant was still there. Judy then said, “check your email later.” I said I would and hung up. Stacey looked at me and said, “are you ok? You look kind of flushed.” I smiled and we went back to work. I checked my email every chance I got and thought maybe Judy was k**ding. Finally I got an email and Judy said she was going to surprise me with a video but this one took a turn and I should spend the time watching it but not until everyone was gone. She told me to pay close attention to the 75-minute mark. I waited until everyone was gone and turned my computer on and ...

... turned the sound up. Just as I started to watch Judy called and asked if I was watching? I said I was just turning it on and she told me to get naked and enjoy. I got undressed and closed the blinds to my private office and sat down to enjoy. Judy and her friend Tom were in bed and going at. Judy started out giving Tom a blowjob, I never realized how well endowed he was. He was thick and over 8 inches. When he came in Judy’s mouth I wasn’t sure he was going to stop. She couldn’t even keep it all in. They wound up in a ton of different positions and each came several times. It was even fun to hear them complain of my small manhood. I was trying to pay close attention to the time and sure enough about the 75-minute mark, the bedroom door opened and I could see someone standing there and watching for about 7-8 minutes before the door quietly closed again. Tom and Judy never seemed to notice. Tom and Judy finished about 10 minutes after that and Tom got up to get dressed while Judy lay there covered with cum. They kissed goodbye and Tom left. Judy just lay there and finally started to play with her moist pussy. After about 3 or 4 minutes there was a knock at the door. Judy said, “come in Tom.” Much to her surprise in walked our cleaning lady, Samantha. Judy finally stopped playing and said, “I am sorry you saw me doing that.” Samantha said, “oh don’t worry, I found it very sexy, but about 30 minutes ago I knocked and no one answered and I heard you moaning and opened the door.” Judy ...