Becoming Cuckold The First Time

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.

She pulled Al over the bed; while kissing him as her hand slides down, she started undoing his belt and pants. As I sat there watching my wife undress this man, she pulled down his shorts taking his cock into her small hand. He was a little larger than me and as thick. She examined his cock while slowly licking the shaft; at first, she took the head in her mouth then the shaft. There I sat watching my wife of 25 years with another man's cock in her mouth as I pleasured myself. As my stomach started to rumble with anxiety becoming more intense, I was also getting excited with my hard cock in my hand. After what seems like forever, Alan grabs her head pushing his whole cock deep into her mouth. As he holds her head with him deep inside, she gages a little; he stiffens up, I can tell he dumped his load deep in her mouth. As he let goes, she takes his cock out and opens her mouth to show him his load. Motions me to come over and kisses me spilling some of his load into my mouth; I became her cum dump! She swallows what was left.

Looking at me saying that it was my turn. That now that I saw her sucking his cock, she wanted to see me getting him hard again. As I obeyed, she laid flat on the bed watching me with his cock in my mouth waiting for him. In a couple of minutes, I got him hard again, tasting some of their left-over cum. Lying beside her, he began to kiss her while his hands roamed over her now naked body. Then playing with her now hard nipples, e slowly went down on her to suck on her freshly shaved pussy until she climaxes. Then moving up with his now hard cock push into her shaved soaking wet pussy but not all the way, just enough to give her the feeling of his large head passing into her. In and out he went with what felt like eternity. There I saw my wife with another man, almost like she was a star in one of the porn flicks we would watch. As he pushed deep into her, I saw her back arching as she climaxed several times. Finally, after a few long minutes of him gently and sometimes hard pushes deep, he moans releasing his full load in her as she does a final climax, and both lay on the bed exhausted. With my cum in my hand.

As we walked back to our cabin, we talked about what she felt about the experience, she expressed she would like to try a few more times with only Al during the cruise. She wanted to know if it was ok with me, I agreed. When we got back to the cabin, we started as I was extremely excited. Although it was sloppy seconds, I shot my load quickly. As she didn't climax, she pushed my head down to finish up her cream pie which was now her, me, and Al all mixed. As I did, she then climaxed like never before as her flower bloomed.

One day we were in port, she told me to go ashore alone that she was staying on board. I returned late in the afternoon; I didn't see her on deck, so I went to our cabin where she was just resting. I asked how was your day, her answer it was exhausting going into detail what happen. That she spent most of the afternoon with Al in our cabin on our bed being fucked. I looked at the bed knowing I was going to sleep on a bed where my wife just had intercourse with another man. Then she told me she had to get ready for dinner as Al was taking her to one of the specialty restaurants. She took a shower, came out laying on the bed to have me shave her again as I prepared her for a long night of pleasure. She told me not to expect her back until morning. In the morning, laying on her stomach next to me offering her cream pie. As I went down, she stayed on her stomach as I saw the cream pie was her ass. I asked what happen and she told me she wanted to offer him her virgin ass, as she never let me do her anally. I cleaned her up and we went to breakfast.

She dated Al five out of the 10 nights on our cruise, except for the first night I was not with her. On two occasions, she stayed out all night only returning in the morning. Each time she came back, she shared details of their activities. What happens on the cruise stays on the cruise, until next time.