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.
