A question I always get is when did I get cuckold? It was not when, it was more like we evolved into the lifestyle with small steps at a time. The first time we were in our mid-50s. Our sex life was straight vanilla, without much excitement. We would start with foreplay, then maybe oral finishing up with intercourse. As for me, I was bored with it all for quite a while. I did have an affair which she found out about. After that cooled down our sex life went back to the way it was, boring.
To spice things up we started to watch prone flicks together, reenacting some of the situations; it added to the excitement. One night we watched a cuckold flick, about an older couple whose wife invited a friend to share their bed. Their age was close to ours which caught her interested. That started the pillow talk, she asked if I would mind being cuckolded. As time passed, she talked more and watched a few more cuckold flicks including a few femdom ones. Again, she asked if I would mind if she cuckolded me on an upcoming 10-day cruise we booked. I said, "Let's see what happens". As it approached, again she started, she led into it as what is good for the goose is good for the gander referring to my affair. As I agreed, as it would be payback for the affair. As the cruise approached, she set rules: I couldn't be with other women, she was in charge, I had to obey her, and I had to stay until she felt comfortable with him. There were other rules including preparing her for her dates.
As the cruise came, in the cabin she again asked if I would mind. I reply again with "Let's see what happens." The first couple of days were at sea, sailing from Miami to Columbia. On the second day, she met a man about our same age on the pool deck. He was a widower from the UK sailing alone. After their afternoon chat, we went back to our cabin to get ready for dinner. In the cabin, she expressed her interest in him and hinted he might be the one. After she took a shower, she lay on the bed telling me to shave her pussy; she wanted to make sure it was smooth and soft just in case. She wore a matching lace underwear set with a semi see-through sundress. As we were leaving, I told her I put a few condoms I put in her purse. She reminded me that we never used condoms and questioned why I thought she would start now, adding that at her age she could no longer get pregnant.
After dinner, she wanted to go to the oldies nightclub which knew I would enjoy. As sat there and did a few dances, her friend (aka Al) came over to say hello. What I didn't know she arranged for us to be there so they could meet. She invited him to join us, and he ordered drinks. After a while, they did a few dances including a few slow dances; at this point I was a bystander. After they returned, he excused himself to use the head; then she told me she liked him, and he would be the one. She said that during the slow dances, she felt him pressed against her. She said she thinks he is as big as me; I am almost 7" and thick. When he returned, I went. On my return, she then excused herself and went to the lady's room. He sat there looking at me with a smile as if he knew something, which I found out later he did.
As we walked back to our cabins, with her holding my hand, while he placed his arm around her waist with his hand sliding down to her ass. From time to time, he would give her a quick kiss and then continue. As we approached the elevators he offered us a nightcap back in his cabin, which she accepted as I went along with it. Once in his cabin, which was like ours, he pulled in a chair from the balcony as they sat on the love seat chatting. He offered some white wine, she had already had too much to drink but accepted the wine, gaining courage. As we sipped the wine the talk went from general to a more explicit nature, with me looking from across the cabin. Soon his hand was rubbing her thigh slowly moving under her dress closer each time to her pussy. As he did, she encourage him by opening her legs just a little to let his hand roam further up. As his fingers reached her panties, he leaned over started to kiss her. She then got up to go to the bathroom, when she returned, I could tell that her bra was off. Instead of sitting down she stood by the bed and said, "Let's do this!" She then flipped up her sundress over her head revealing she also took off her panties as well, showing Alan her smooth shaved pussy and C+ breast. She instructed me to stay in the chair with my shorts down to pleasure myself.
