My wife Jan and I were high school sweethearts and had gotten married fairly young. Our 30th wedding anniversary was approaching so we decided to do something very special to celebrate. We decided to celebrate our 30th anniversary by taking a 10 day cruise in the Caribbean. Our 4 children were raised and the last one had just graduated from college.
Jan and I talked a lot about where we were going and what we expected from the cruise. One thing that was near the top of my list was for Jan to wear some sexy clothes that she normally could not wear at home. She told me she had a goal to loose 20 pounds before we left. She said if she was successful she would wear anything I wanted her to wear as long as it was not illegal. My mind went into overdrive after hearing a bold statement like that. As it turned out she did put some more limitations on what she would wear but I was still very satisfied. She was thrilled to lose 20 pounds and I was thrilled at how good she looked.
At last the day came and we anxiously headed for the airport. Jan looked fabulous with her slimmer figure in a short skirt and low cut top. She had promised to wear panties as little as possible. It was such fun watching the other men in the airport and on the plane check out Jan's cleavage. We had discussed how much I enjoyed that sort of thing. My wife does not pretend to understand it but she promised to do her best to attract attention on this trip.
I was elated to hear her say that but knew better than to get my hopes too high. Still, on one occasion as we waited for the plane, I could not help but notice how sexy she looked sitting there with her skirt about mid thigh. That was not lost on the men sitting around her either. I sat down across for her, pretending not to know her. She smiled, looked around to make sure it was safe, and quickly opened her legs. I observed that my 50 something wife and grandma was not wearing panties and was smoothly shaved down there. I really had high hopes now.
The plane trip was uneventful. There was a guy sitting beside Jan who did his best to look at her boobs and legs without either of us knowing. I got amused watching him and so did my wife. Once when he went to the rest room I suggested Jan might pull her skirt up a bit more and show some more of her thighs. I knew she would ignore me like she always does but this time she didn't. She pulled her skirt up and asked if that was enough. I told her to pull it up a little more. She reminded me that if it goes much more this guy will also know she isn't wearing panties. I didn't care if he knew but I decided to keep my mouth shut. When the old boy came back he was pleasantly surprised. My wife's legs were on display for all to see and I think I can safely say we enjoyed the view. I still get hard just thinking about it.
Once the plane landed we began the hassle of getting on the ship and finding our room. The ship set sail as we walked around trying to get our bearings on board. It was incredible how big the thing was. The crew put us through our lifeboat drill and we were ready to have a good time.
That evening Jan and I were talking about what we should do and I made a suggestion. Over the years we have talked about role playing to enhance our sex life. We have never actually done it so I thought we might give it a try. I expected a miserable failure because my wife isn't normally into things like this.
After some discussion we agreed Jan would wear a short halter dress and go to this lounge we had located. She would enter alone, sit at the bar, and see if she attracted any attention. She was to pull her dress up so everyone could see those pretty legs of hers. Much to my surprise she agreed to do it. I was surprised even more when I saw just how much of her legs she exposed in the bar.
It went exactly as I expected. Several men walked by and checked her out. She ordered a drink and sat there as if waiting on someone. After about 30 minutes I went in and introduced myself to her. It went better than I expected. It was hard to keep from laughing but we managed to do it for the most part. After we talked a while I put my hand on her bare thigh and leaned over and kissed her. A guy who was sitting 3 stools down was watching intently. Jan could not see him. I whispered in her ear we should go and we walked out of the lounge. I had an erection that wouldn't quit!
Jan and I walked around the deck and enjoyed the beautiful night at sea. We found a fairly dark place and I pulled Jan's straps down freeing her breasts. They felt wonderful and her nipples tasted even better. The night air was cool enough to make them quite hard. Jan and I kissed like teenagers. We discovered an exercise mat in a secluded place, so Jan ended up on her back with her dress around her waist. She briefly sucked my cock before I put it in her. We had not fucked with that sense of urgency in a very long time. It felt so good to cum in her. As I got off Jan a couple walked by and pretended not to notice her fixing her dress. We headed to our cabin to get some rest. It had been a busy day for grandma and grandpa.
The next morning we throughly enjoyed the day exploring the ship and the amazing weather. That night there was live entertainment so Jan put on a sexy dress and decided to attend. She was doing a much better job of dressing sexy than I ever expected. The dress she wore that night exposed most of her tits and they jiggled so nicely when she walked in her 3 inch heels. It was another wonderful evening. When we got back to the cabin she sucked my cock and I came in her mouth.
The next evening we decided to role play again. This time we picked a different lounge. Jan wore a skirt that was 4 inches above the knee with a slit up the front. I asked her if she was going to wear panties and she shook her head no. When she sat down it would be interesting because the slit was pretty high. Her top fit tight and, again, showed plenty of her tits. My wife looked awesome! I was so proud of her.
We got to the lounge and Jan went inside. Our plan was pretty much the same as last time. She sat down and ordered a drink while I watched to see if anyone checked her out. It was all couples in there but I saw several of the men watch her as she walked past. Her legs looked amazing as she sat there on that stool. She did not look like anyone's grandma.
My 30 minute waiting period was about to expire when some man stopped and said something to my wife. There was a brief exchange and then he sat down on the stool beside her. This was a surprise. Its almost all couples on a cruise so where did he come from? I wondered if she needed to be rescued? We didn't have a plan for this. I decided to wait. They were talking and it looked like she was enjoying the conversation.
As I waited it suddenly hit me how erotic this was. My wife, dressed in her sexy clothes, was talking to a stranger and that was turning me on. I couldn't explain why but I liked it. I tried to imagine what they were talking about. I'm sure it was nothing sexual. After 20 minutes or so my wife got up and headed for the rest room. I went behind her so we could talk. I asked her if everything was alright and she said it was. They were just talking. His name was Roland and he worked on the ship.
"So did you notice him checking you out?" I asked.
"His eyes went straight to my boobs as soon as he sat down."
"So what do you want to do?"
"If you're in a hurry say so, otherwise I can talk to him some more. You seem to be enjoying this." she said.
I was enjoying it so I told her to go ahead and chat with him some more. As soon as Jan got back they began dancing. She was so sexy out there dancing with this stranger. My cock began to get hard just watching. I knew he had to be trying to figure out how to get my wife into bed. After watching her dance with this guy I was ready to fuck her. She looked incredible in that skirt. An hour or so and several dances later Jan headed outside alone.
I caught up to her and she filled me in on Roland. He works as some sort of officer on the ship, he's divorced, and he's from Argentina.. and he loves to dance. She also said he is a very good dancer and nice looking. He was apparently very complimentary of my wife's looks too, although I had trouble finding out exactly what he said. Once again Jan and I ended up in our room fucking like teenagers. I told her that seeing her with him was a big turn on for me but I couldn't explain why.
The next day Jan told me she wouldn't mind seeing Roland again if it effected me like it had the previous night. I told her he would be trying to get her in bed and she assured me that would never happen. Eventually she admitted that he had asked if he could contact her and she told him it would be alright. He wondered where I was and she told him that, at times, we did different things. As we went about our day she bumped into him on one of the decks. After chatting briefly she came back to me and said she had a "date" to go dancing with Roland at 10:00 that evening. We were going to the live entertainment and it would be over by then. The thought of seeing her dancing with him again was very exciting.
That evening we hurried back to our cabin so she could put on just the right dress for her date. After changing clothes and touching up her makeup she was off to the dance. I waited about 30 minutes and headed that way myself.
Once in there I located them. I figured by now he knew what I looked like so I better not look like some sort of stalker. I saw them sitting at a table talking. They danced a few times and, maybe it was my imagination, but I thought he was holding her a little closer. I knew he had to be doing his best to fuck her. At one point they went for a walk. I didn't follow but I did get s glimpse of them at one point but nothing was happening. I went back to our cabin and waited. about 1:30 Am I heard voices in the hallway. I peeked through the peep hole in the door and saw both of them standing there. I couldn't hear the conversation but it looked like he said good night and walked off.
I was pretty much ready to fuck as soon as she walked in the room. I was interested in details of her evening so she finally agreed to tell me about it. Frankly there wasn't much to tell. They danced. He tried to convince her to go to his cabin but she refused. They walked on deck and did a lot of talking. Did he touch her or try to? She said he did not. He did tell her how beautiful she is. Did she enjoy being with him? She told me she had a great time and they plan to do it again.
