My wife and I, Anne and Ken, had been discussing her getting together with another man for about six months. More precisely I brought it up about six months ago and she didn't give an immediate no. There wasn't an enthusiastic yes either.
We talked about it on and off. I really wanted to see her fuck another guy or couple and she worried it would change our relationship. I assured her over and over that I would love her whether we went down this road or not, but I would really love for her to try it because I wanted her to experience as much pleasure as possible. I also thought it would be extremely hot to watch someone else seduce my wife.
We had been together for almost thirty years at this point. While my love for her was greater than ever, I knew I was not able to please her quite the way I could when we were younger. We are both in our early 50s and had put on a few pounds over the years. My wife had extra curves which made her look more appealing whereas my extra pounds just made me look fat and out of shape. She still received lustful looks when we were out together. I can only imagine the looks she got when I wasn't with her.
Occasionally, I would look online just to see what was out there in case she would agree. I would sometimes find someone advertising and bring it to her attention. I would usually get the, "I'm not ready or he doesn't sound nice" answer. I didn't give up and kept telling her how sexy she is and how lucky another man would be getting to be with her.
One day I noticed an ad for a 38-year-old gentleman coming to Chicago for a week for business and was looking to play with the wife half of a couple. There was a body picture of his waist to his neck. It didn't show his cock or his face, but he was definitely well put together and very black. He would be staying at the Hyatt downtown and he preferred to host.
This was about 3 weeks prior to his arrival. Since we live just outside Chicago, I showed it to my wife, and she read it and kept looking at it. Finally, after thinking about it for about 15 minutes she said "maybe". I was happy it wasn't a no like usual.
Three days later as I was on the computer, she asked to see the ad again. I pulled it up and handed her my laptop. She read it and thought for a while and handed me back my laptop and told me to contact him and maybe just maybe we could get together with him. I did that immediately figuring I better strike fast. I sent a pic of the two of us taken at a wedding we recently attended. My wife looked exceptionally hot and was getting looks all night. I hoped he would be pleased.
I told him a little about us and that we were newbies at wife sharing but we were both on board. He responded quickly with a pic of himself in a suit. He looked about 30 and he was well built. He said my wife looked hot in the photo and hoped we had a few more to share but if not, that was okay as she was beautiful. He said his name was Chet and he was 6'3 and 220 lbs. He explained that he would be in Chicago on business and was available after 4 pm every day. He went on to say that he would need to talk to my wife also to make sure she was on board. I sent him back a couple of pics of my wife in her one-piece swimsuit from our last vacation and told him she would be emailing him shortly.
I showed her the email string so far and she blushed a little that he said she was beautiful. I told her Chet was waiting to hear from her. The weekend was coming up and we were busy, so I didn't know whether she contacted Chet or not. I had to travel out of town for business and asked her Monday before I left if she had time to contact Chet. She said she had, and he sounded nice and sincere, and they were talking about us getting together when he was in town.
I headed out and remembered it later while sitting by myself in my hotel room. I signed into the email we created for this and found the emails. There were a few more since the last one I sent. In her first email she said how nervous she was since she hadn't been with another man in a long time and wondered why a young, good looking guy would want to be with an older woman like her. She went on to tell him that this was my idea, but she had come around to it finally and was looking forward to it but was very nervous.
Chet responded back telling her how beautiful she was and that any man would be incredibly lucky to be with her. He also told her that while younger women were great, he preferred older women as they were more experienced and knew what they wanted. After a few more back and forth emails Chet asked to speak to her and gave his phone number.
I called home as I usually do every night when I'm on the road and we talked about how my flight was and other mundane things before I finally asked if she had contacted Chet. She had and said they had a nice conversation and Chet sounded very sexy on the phone. They discussed which night we could come into the city and had settled on Monday night, his first in town. We would meet him for drinks and then dinner and if everyone were agreeable back to his room. She sounded excited. I was thinking more was said than just a time and place but was happy because I was finally going to see my wife with another guy. I told her she should probably get a new outfit and some sexy lingerie for the occasion, and she readily agreed.
On Wednesday I checked the email again and found a few more emails back and forth with some pics. Chet was in his underwear with an impressive package barely concealed and Anne sent a pic she must have taken in our bathroom in just her panties. Her perky tits on full display. It seemed like their talks were progressing.
I texted Chet after seeing these and asked how he and Anne were getting along since I hadn't communicated with him since I turned this over to her. He said she was very sexy and was looking forward to meeting us. He asked if I had any limits for my wife and I told him it was up to the two of them. I did say no permanent marks but on everything else she could make her own decisions.
He asked if we were going to take any pics or video and I told him maybe a few pics but they were for our use only. He said that was fine but to please be discrete and not show his face. I understood. He told me he usually took video of his encounters for his own collection. That was fine with me since I would get to see it live.
Thursday night I checked the email again and found 2 more emails. The first from Chet and he told her how much fun they would have Monday night and how much pleasure they would both take. He told her he loved oral sex and anal as well as vaginal and would please her all night long.
He included two pics. One of him nude laying on a bed with a raging hardon and one which looked the similar but had two white hands holding his cock with a few inches sticking out. Holy crap I didn't know how my wife was going to work with that. It looked twice as big as mine.