I have always been both a voyeur and an exhibitionist. I have also always had a raging sexual appetite than has caused me to masturbate at least twice a day, and sometimes that isn’t good enough. At times there is no substitute for the real physical connection with a member of the opposite sex.

My name is Joe and I live in Chicago. Despite the number of people living in the city it can be difficult to find the right situation, especially if you are a single male looking to join a couple. Back in the late 90s I chatted with a couple through a chat room on AOL. The husband liked sharing his wife and that was all I needed to hear. I described myself honestly as being 21 and good looking, tall at 6’-1”, but on the slim side at 170#. I have two features above all others that I think are an advantage. I have very broad shoulders, no hair on my chest or back, and very little body fat, so my 170# is all well defined muscle, much like an Olympic swimmer. My other strong feature is in my pants. I am circumcised and an honest 8 inches. I am unusually thick and very wide. I always keep my balls shaved and everything else very closely trimmed.

From chatting with this couple I learned that they were in their 40’s and pretty comfortable financially living on the north shore, and that they had booked a hotel room near O’Hare airport for a weekend away from their kids. We agreed to meet that night and I was to call from the lobby where the hubby would meet me. For the life of me I can’t remember his name, but learned that his wife’s name was Brenda.

After arriving and calling, he came down to meet me and explained that she was nervous even though this wasn’t their first time. He wanted me to sit and talk to her until she was comfortable and then he would initiate things. He also gave me a hint that she wanted to cum and suggested I use my fingers to do that before intercourse to really get her in the mood. Brenda turned out to be pretty hot, a true MILF soccer mom, with long bleach blonde hair, pretty face, nice legs, and a decent chest. She was in the room wearing a see-though red teddy-like thing that she insisted she wore to her kids school events with a pair of jeans but I didn’t believe it.

After chit chat that I pretended to be interested in while sitting on the couch, hubby was in a chair, Brenda paraded all around until she invited me to the bed.

There was some light kissing and groping and hubby said that he only wanted to watch. Brenda got bold quite quickly and soon had me naked and lying on the bed. She gave me head to the best of her ability, but because of my width there was a lot of teeth scraping. I have gotten used to this and almost expect it. I love getting head so I deal with it for as long as possible. All the while I was rubbing her pussy and clit. She responded by getting very wet and pushing back into my hand which I took as a hint to insert a few fingers. Within minutes she stopped sucking my dick and pushed her head into the sheets as she came.

I tried to get Brenda’s teddy completely off, but she was a little insecure of her stomach so she pulled her arms free and pushed it down to cover her insecurities. I went to pull out a condom from the pocket on my jeans laying on the floor and they asked if I had to use it. Looking back it was dumb but I agreed to go bareback after they insisted they were clean and didn’t “play” very often. We started slow with her on top so that she could get used to my size. I’ll give credit to her orgasm from earlier that she was very wet and got me all the way in with only a few strokes. Once she was comfortable she asked me to get on top.

With me on top we did variations of missionary where I had her legs spread wide, or over my shoulders. I have some pretty good stamina and varied the pace of my thrusts to not only last myself, but also to adjust to her reactions. When I felt that I was close to cumming I did the polite thing and asked where she wanted it. She surprised me by saying inside her pussy. I increased my pace and right before the first spurt I went in as deep as I could until I bottomed out against her cervix and held it there. She got wide eyed and gasped, maybe in pain, but I filled her with a large load.

After we had calmed down the husband came over and kissed her and asked if she enjoyed it. She claims that she did but was going to be sore later. There was some awkwardness afterwards with chit chat, and luckily for me they said that they wanted to have some fun on their own. I took my queue, got dressed, thanked them both, and gave her a deep kiss. They insisted that they would keep my email and phone number and that we would get together again the next time they had a weekend free from the kids. And they did keep their promise!